1-9 A-D E-G H-M N-P Q-S T-Z

ETİL OKTANOL (ETHYL OCTYNOL)

ETHYL OCTYNOL
Cas No: 5877-42-9
METATAGS:ETHYL OCTYNOL; ethyl octynol; ETO; 4-Ethyl-1-octyn-3-ol; 4-ethyloct-1-yn-3-ol;Ethyl octynol;4-Ethyl-3-hydroxy-1-octyne; 4-Ethyl-1-octyn-3-ol; 3-Hydroxy-4-ethyl-1-octyne; 4-ETHYL-1-OCTYN-3-OL; Timtec-bb sbb005885; 4-Ethyl-1-octyn-3-o; 4-Ethyl-1-octyne-3-o; 4-Ethyl-1-octyn-3-ol; (2-Ethyl-1-hydroxyhexyl)acetylene; 1-Octyn-3-ol, 4-ethyl-; 1-Octyne-3-ol, 4-ethyl-; 4-Ethyl-1-octyn-3-0l; 4-Ethyl-1-octyn-3-ol; 4-Ethyloct-1-yn-3-ol; Einecs 227-545-9; Ethyloctynol; Nsc 62119; 2-Imidazolecarboxylic Acid Ethyl Ester;4-Ethyl-1-octyn-3-ol; ETİL OKTİNOL; ETIL OKTİNOL; ETIL OKTINOL; ETİL OKTİNOL; ETIL OKTANOL; ETİL OKTANOL; etil oktinol; etıl oktinol; etıl oktınol; etil oktinol; etıl oktanol; etil oktanol; ETO; 4-ETHYL-1-OCTYN-3-OL; 4-ETHYLOCT-1-YN-3-OL;ETHYL OCTYNOL;4-ETHYL-3-HYDROXY-1-OCTYNE; 4-ETHYL-1-OCTYN-3-OL; 3-HYDROXY-4-ETHYL-1-OCTYNE; 4-ETHYL-1-OCTYN-3-OL; TİMTEC-BB SBB005885; 4-ETHYL-1-OCTYN-3-O; 4-ETHYL-1-OCTYNE-3-O; 4-ETHYL-1-OCTYN-3-OL; (2-ETHYL-1-HYDROXYHEXYL)ACETYLENE; 1-OCTYN-3-OL, 4-ETHYL-; 1-OCTYN; -3-OL, 4-ETHYL-; 4-ETHYL-1-OCTYN-3-0L; 4-ETHYL-1-OCTYN-3-OL; 4-ETHYLOCT-1-YN-3-OL; EİNECS 227-545-9; ETHYLOCTYNOL; NSC 62119; 2-IMİDAZOLECARBOXYLİC ACİD ETHYL ESTER;4-ETHYL-1-OCTYN-3-OL; eto; 4-ethyl-1-octyn-3-ol; 4-ethyloct-1-yn-3-ol;ethyl octynol;4-ethyl-3-hydroxy-1-octyne; 4-ethyl-1-octyn-3-ol; 3-hydroxy-4-ethyl-1-octyne; 4-ethyl-1-octyn-3-ol; timtec-bb sbb005885; 4-ethyl-1-octyn-3-o; 4-ethyl-1-octyne-3-o; 4-ethyl-1-octyn-3-ol; (2-ethyl-1-hydroxyhexyl)acetylene; 1-octyn-3-ol, 4-ethyl-; 1-octyne-3-ol, 4-ethyl-; 4-ethyl-1-octyn-3-0l; 4-ethyl-1-octyn-3-ol; 4-ethyloct-1-yn-3-ol; einecs 227-545-9; ethyloctynol; nsc 62119; 2-ımidazolecarboxylic acid ethyl ester;4-ethyl-1-octyn-3-ol;

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ETHYL OCTYNOL

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CAS #

5877-42-9
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PRODUCT DESCRIPTION
PRODUCT

Ethyl octynol

CAS #

5877-42-9

SYNONYM

4-Ethyl-1-octyn-3-ol; 4-ethyloct-1-yn-3-ol;Ethyl octynol;4-Ethyl-3-hydroxy-1-octyne; 4-Ethyl-1-octyn-3-ol; 3-Hydroxy-4-ethyl-1-octyne

FORMULA

C10H18O

TYPICAL PRODUCT SPECIFICATIONS
MOLECULAR WEIGHT

154.25

INCHI

1S/C10H18O/c1-4-7-8-9(5-2)10(11)6-3/h3,9-11H,4-5,7-8H2,1-2H3

INCHIKEY

CUUQUEAUUPYEKK-UHFFFAOYSA-N

NOTES

Ethyl octynol uses and applications include: Corrosion inhibitor in oil well acidizing, mild steel pickling, mild steel cleaning in acid systems; electroplating bath additive; curative for paints, elastomers, adhesives

CLASS

Specialty Chemicals

FUNCTIONS

Acid, Additive

INDUSTRY

Plating, Adhesives

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ETHYL OCTYNOL

PRODUCT IDENTIFICATION

CAS NO.
5877-42-9

ETHYL OCTYNOL

EINECS NO.

FORMULA C10H18O
MOL WT. 154.25
H.S. CODE
TOXICITY
SYNONYMS 4-Ethyl-1-octyn-3-ol;
RAW MATERIALS

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE
colorless to slightly yellow liquid

MELTING POINT -45 C
BOILING POINT 205 C
SPECIFIC GRAVITY
0.87

SOLUBILITY IN WATER
Immiscible

AUTOIGNITION

pH
VAPOR DENSITY
NFPA RATINGS
FLASH POINT
84 C

STABILITY Stable under ordinary conditions
APPLICATIONS

functional intermediate which has -OH group and alkyne; mainly used in corrosion inhibitor fields

SALES SPECIFICATION
APPEARANCE

colorless to slightly yellow liquid

ASSAY
97.0% min

MOISTURE (K.F)
0.2% max

TRANSPORTATION
PACKING 170kgs in Drum
HAZARD CLASS
UN NO.
GENERAL DESCRIPTION OF ALKYNE
Alkynes are aliphatic hydrocarbons that have one or more carbon-carbon triple bonds. The general structure of the alkyne hydrocarbons with one triple bond is CnH2n-2. They are insoluble in water but easily soluble in common organic solvents of low polarity. The features of alkynes in chemical synthesis is due to the acidity of hydrogen atoms bonded to triply bonded carbons as well as the triple bonds themselves. Addition reactions are typical in alkyne reactions; halogenation, hydrogenation, hydrohalogenation, hydration, oxidative cleavage, nitrile formation and acidity of terminal alkynes. Polymerisation and substitution reactions are also useful in chemical synthesis.
Addition Reactions
Catalytic Hydrogenation by Pt and Pd hydrogenation catalysts to yeild alkanes without isolation of alkene intermediates.
Catalytic Hydrogenation by Lindlar's catalyst to yeild cis- or trans- alkenes without further reduction to alkanes
Addition by Electrophilic Reagents
Addition of halides (chlorine, bromine, iodine) to yield dihalogen substituted alkanes at the solid bond site
Addition of hydrogen halides (HCl, HBr, HI) to yield monohalogen substituted alkenes or dihalogen substituted alkanes
Hydration of alkynes to yield ketone products through enol tautomer intermediate stage, whereas the hydration of solid bonds gives alcohol products (exceptionally acetylene yields acetaldehyde ).
Hydroboration by disiamylborane to yield ketones or aldehydes
Oxidation cleavages of the triple-bond to give carboxylic acid products with oxidizing agents (potassium permanganate and ozone)
Nucleophilile Addition by sp-hybrid carbon atoms of the triple-bond render alkynes (nitrile formation)
Nucleophilile Reduction by solutions of sodium in liquid ammonia to trans-alkenes
The name of all alkynes end in "-yne" adding a prefix to indicate the location of the triple bond in the molecule.

COMPOUND

SYNONYM

FORMULA

CAS RN

M.P (C)

B.P (C)

Ethyne

Acetylene

C2H2 74-86-2
-84.0

-28
Propyne

Methyl acetylene

C3H4 74-99-7 -103 -23
1,3-Butadiyne

Diacetylene

C4H2 460-12-8

10

1-Butyne

Ethyl acetylene

C4H6 107-00-6 -125.7
8

2-Butyne

Crotonylene C4H6 503-17-3 -32.2 27
1,3-Pentadiyne

 

C5H4 4911-55-1

 

3-Penten-1-yne
Propenyl acetylene

C5H6 2206-23-7

 

2-Methyl-1-buten-3-yne
Isopropenyl acetylene

C5H6 78-80-8
-113

32
1-Penten-3-yne

Methyl vinyl acetylene

C5H6 646-05-9

 

1-Penten-4-yne

Allyl acetylene

C5H6 871-28-3

 

2-Pentyne

Ethyl methyl acetylene

C5H8 627-21-4 -109 56
3-Methyl-1-butyne

Isopropyl acetylene

C5H8 598-23-2 -89.7
26

1-Pentyne

Propyl acetylene

C5H8 627-19-0 -106
40

3-Hexyne

Diethyl acetylene

C6H10 928-49-4 -103
81

2-Hexyne

Methyl propyl acetylene

C6H10 764-35-2 -89.1
84

4-Methyl-1-pentyne

Isobutyl acetylene

C6H10 7154-75-8 -105
61

1-Hexyne

Butyl acetylene

C6H10 693-02-7 -131.9
71

3-Methyl-1-pentyne

sec-Butyl acetylene

C6H10 922-59-8

58

4-Methyl-2-pentyne

Isopropyl methyl acetylene

C6H10 21020-27-9
-110

73

3,3-Dimethyl-1-butyne

tert-Butyl acetylene

C6H10 917-92-0 -78.2 38
1,5-Hexadiyne

Dipropargyl

C6H6 628-16-0
-6

86

1,4-Hexadiyne

 

C6H6 10420-91-4

79

1,5-Hexadien-3-yne

Divinyl acetylene

C6H6 821-08-9


1-Hexen-3-yne

Ethyl vinyl acetylene

C6H8 13721-54-5

84

4-Methyl-2-hexyne

sec-Butyl methyl acetylene

C7H12

20198-49-6 -108
100

2-Methyl-3-hexyne

Isopropyl ethyl acetylene

C7H12

-117

95

5-Methyl-2-hexyne

Isobutyl methyl acetylene

C7H12 53566-37-3
-93

102

3-Ethyl-1-pentyne

 

C7H12

 

84
1-Heptyne

n-Pentyl acetylene

C7H12 628-71-7
-81

100

4,4-Dimethyl-2-pentyne

tert-Butyl methyl acetylene

C7H12 999-78-0

83

3-Heptyne

Ethyl propyl acetylene

C7H12 2586-89-2
-131

107

4,4-Dimethyl-1-pentyne

Neopentyl acetylene

C7H12

-75
78

2-Heptyne

n-Butyl methyl acetylene

C7H12 1119-65-9

112

1,6-Heptadiyne

 

C7H8 2396-63-6

108

1,7-Octadiyne

 

C8H10 871-84-1

135

2,6-Octadiyne

 

C8H10 764-73-8

 

Cyclooctyne

 

C8H12 1781-78-8

 

4-Octyne

Dipropyl acetylene

C8H14 1942-45-6 -102.5
132

1-Octyne

n-Hexyl acetylene

C8H14 629-05-0 -79.3 126
3-Octyne

n-Butyl ethyl acetylene

C8H14 15232-76-5 -104
133

2-Octyne

n-Pentyl methyl acetylene

C8H14 2809-67-8 -61.6 138
1,8-Nonadiyne

 

C9H12 2396-65-8 -21

Cyclononyne

 

C9H14 6573-52-0

 

1-Nonyne

n-Heptyl acetylene

C9H16 3452-09-3 -50 151
3-Nonyne

Methyl n-pentyl acetylene

C9H16 20184-89-8

157
2-Nonyne

n-Hexyl methyl acetylene

C9H16 19447-29-1

162

4-Nonyne

n-Butyl propyl acetylene

C9H16 20184-91-2

 

Cyclodecyne

 

C10H16 3022-41-1

 

5-Decyne

Di-n-butyl acetylene

C10H18 1942-46-7
-73

 

3-Decyne

Ethyl n-hexyl acetylene

C10H18 2384-85-2

179

1-Decyne

n-Octyl acetylene

C10H18 764-93-2
-44

174

2,2,5,5-Tetramethyl-3-hexyne

Di-tert-butyl acetylene

C10H18 17530-24-4

 

1-Undecyne

n-Nonyl acetylene

C11H20 2243-98-3 -25
195

6-Dodecyne

Di-n-pentyl acetylene

C12H22 6975-99-1

 

1-Dodecyne

n-Decyl acetylene

C12H22 765-03-7
-19

225

1-Tridecyne

n-Undecyl acetylene

C13H24 26186-02-7 -5
234

1-Tetradecyne

n-Dodecyl acetylene

C14H26 765-10-6

252

1-Pentadecyne

n-Tridecyl acetylene

C15H28 765-13-9
10

269

1-Hexadecyne

n-Tetradecyl acetylene

C16H30 629-74-3
25

285
1-Heptadecyne

n-Pentadecyl acetylene

C17H32 26186-00-5 22
300

1-Heptadecyne

n-Pentadecyl acetylene

C17H32 26186-00-5

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Compound StructureIUPAC Name: 4-ethyloct-1-yn-3-ol | CAS Registry Number: 5877-42-9
Synonyms: Ethyloctynol, 4-Ethyl-1-octyn-3-ol, 1-Octyn-3-ol, 4-ethyl-, 4-Ethyl-1-octyn-3-0l, 4-Ethyloct-1-yn-3-ol, 1-Octyne-3-ol, 4-ethyl-, EINECS 227-545-9, NSC 62119, NSC62119, SBB005885, LS-98168, InChI=1/C10H18O/c1-4-7-8-9(5-2)10(11)6-3/h3,9-11H,4-5,7-8H2,1-2H
Molecular Formula: C10H18O Molecular Weight: 154.249320 [g/mol]
H-Bond Donor: 1 H-Bond Acceptor: 1
InChIKey: CUUQUEAUUPYEKK-UHFFFAOYSA-N

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4-Ethyl-1-octyn-3-ol(ETO, ETHYL OCTYNOL)
Product:
4-Ethyl-1-octyn-3-ol(ETO, ETHYL OCTYNOL)
CAS No.:
5877-42-9
Use:
4-Ethyl-1-octyn-3-ol(ETO, ETHYL OCTYNOL) is
mainly used in corrosion inhibitor fields and also used as intermediate.
Synonym: ETHYL OCTYNOL, ETO

Previous : 14984-68-0

Next : 2439-10-3

Inventors:
KEENEY B
Application Number:
05/153841
Publication Date:
04/09/1974
Filing Date:
06/16/1971
Export Citation:
Click for automatic bibliography generation
Assignee:
HALLIBURTON CO,US
Primary Class:
106/14.13
Other Classes:
106/14.15, 106/14.16, 106/14.18, 252/388, 252/390, 252/395, 510/253, 510/255, 510/264, 510/265, 510/267, 510/269, 510/274
International Classes:
C23F11/04; C23G1/06; (IPC1-7): C09D5/08
Field of Search:
106/14 252
View Patent Images:
Download PDF 3802890 PDF help
US Patent References:
3404094 Corrosion inhibitor composition October 1968 Keeney
3382179 Corrosion inhibitor composition May 1968 Keeney et al.
3319714 Well acidizing method May 1967 Knox

 

 

Primary Examiner:
Wong Jr., Harry
Attorney, Agent or Firm:
Weaver, Thomas Tregoning John R. H.
Parent Case Data:


This is a Continuation of application Ser. No. 783,117, filed Dec. 11, 1968, now abandoned.
Claims:
1. A composition consisting essentially of:

2. The composition of claim 1 further consisting of an alcohol represented by the formula R4 OH wherein R4 is a radical selected from the

3. The composition of claim 2 further consisting of a nitrogen base selected from the group consisting of mono-, di-, and trialkyl amines having from two to six carbon atoms in each alkyl moiety and 6-membered

4. The composition of claim 1 wherein said surface active agent is

5. The composition of claim 4 wherein said acetylenic compound is selected from the group consisting of ethyl octynol, propargyl alcohol, methyl

6. The composition of claim 4 wherein said acetylenic compound is ethyl

7. The composition of claim 7 further consisting of alkyl pyridines and

8. A method for protecting a metal selected from aluminum, aluminum alloys and mixtures thereof against corrosion by an aqueous hydrochloric acid solution in contact therewith, comprising contacting said metal with a composition consisting essentially of:

9. The method of claim 10 wherein said composition further consists of an alcohol represented by the formula R4 OH wherein R4 is a radical

10. The method of claim 11 wherein said composition further consists of a nitrogen base selected from the group consisting of mono-, di-, and trialkyl amines having from two to six carbon atoms in each aklyl moiety

11. The method of claim 10 wherein said surface active agent is represented

12. The method of claim 13 wherein said acetylenic compound is selected from the group consisting of ethyl octynol, propargyl alcohol, methyl

13. The method of claim 13 wherein said acetylenic compound is ethyl

14. The method of claim 14 wherein said composition further consists of

15. The method of claim 16 wherein said composition further consists of

16. The method of claim 16 wherein said composition further consists of alkyl pyridines and normal propanol.

Description:
BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates generally to corrosion inhibitors and methods for inhibiting the corrosion of metals, and more particularly, but not by way of limitation, to an aluminum corrosion inhibitor for use with aqueous acids, and to methods for inhibiting the corrosion of aluminum by aqueous acids.

2. Description of the Prior Art

Prior known compositions for the inhibition of corrosion of aluminum surfaces when contacted with aqueous acids have been employed with varying degrees of success. A failing of these prior art corrosion inhibiting compositions is that they cease to be effective after relatively short periods of time or breakdown under high temperature conditions, that is, temperatures in the range of from 125° to 175°F., or higher. A further failing of these prior art compositions is that they are not effective to a comparable degree for substantially all commonly used aluminum alloys.

SUMMARY OF THE INVENTION

The present invention relates to new and useful compositions which may be employed in acid solutions to decrease or inhibit the corrosion of aluminum in contact with the acid solutions. The present invention provides a corrosion inhibitor for inhibiting the corrosion of aluminum and alloys thereof by aqueous acids, which inhibitor comprises an anionic surface active agent and an acetylenic compound. The invention further provides a method for inhibiting the corrosion of aluminum and alloys thereof.

The present invention is particularly useful in cleaning aluminum with aqueous acids such as in the removal of scale from aluminum heat exchangers, tanks, pipes, etc., with dilute hydrochloric acid and inhibiting corrosion of aluminum tanks, pipes, etc., which must contain dilute acids.

It is therefore an object of the present invention to provide an inhibitor composition and a method of inhibiting corrosion of aluminum surfaces when such surfaces are contacted by aqueous acids.

Another object of the present invention is the provision of an inhibitor composition and a method of inhibiting the corrosion of aluminum surfaces when contacted with aqueous acids, which composition and method are effective at low temperatures as well as high temperatures.

A further object of the present invention is to provide an inhibitor composition and a method of inhibiting the corrosion of aluminum and alloys thereof when contacted with acid solutions, especially hydrochloric acid at high temperatures for relatively long periods of time.

Yet a further object of the present invention is to provide an inhibitor composition and a method of inhibiting aluminum and alloys thereof when contacted with acid solutions whereby a comparable degree of corrosion inhibition may be obtained for most commonly used aluminum alloys.

These and other objects and advantages of the present invention will become readily apparent from the description of the invention and examples which follow.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

It has been discovered that an anionic surface active agent and an acetylenic compound, in particular amounts of each, provides a composition having superior aluminum corrosion inhibiting properties when added in proper order in small quantities to an acid solution constituting the corrodent. In addition, an anionic surface active agent together with a synergistic blend of an acetylenic compound and a non-acetylenic alcohol; or one or more acetylenic compounds, a nitrogen base compound and one or more non-acetylenic alcohols; or one or more acetylenic compounds, a nitrogen base compound and an aldehyde or a solution of aldehyde in alcohol; when added to a corrodent acid solution in particular quantities and in particular order provide compositions having superior aluminum corrosion inhibiting properties. The relative amounts of the acetylenic compound, non-acetylenic alcohol, nitrogen base compound and aldehyde may vary over a wide range. Furthermore, it has been found that one of the preferred compositions described above may be used in preference to another to obtain the best corrosion inhibiting properties, depending on the particular aluminum alloy to be protected, the temperatures to be encountered, and the strength or concentration of the acid corrodent. In general, the anionic surface active agent concentration in the corrosion inhibitor may vary from about 15% to 35%. However, lower and higher concentrations will still be effective.

In the preferred form of the invention the anionic surface active agent is a saturated hydrocarbon sulfonate having the general formula RSO3 X with R being a C8 to C25 saturated hydrocarbon chain and X being an alkali metal or ammonium. The sulfonate is made by treating a saturated hydrocarbon (aliphatic or cycloaliphatic) of some predetermined chain length with sulfur dioxide and chlorine in the presence of actinic light. Gamma radiation and certain catalysts can be substituted for the actinic light. This forms a hydrocarbon sulfonyl chloride which is subsequently neutralized with an alkali metal hydroxide or ammonium hydroxide. The preferred material has the formula C13 H27 SO3 Na and is made by gassing a C-13 straight chain saturated hydrocarbon (aliphatic) to a specific gravity of 0.91 to 0.97 before neutralization. The anionic surface active agent C13 H27 SO3 Na is sometimes referred to herein after as CRA. U.S. Pat. No. 2,999,812 illustrates a method of preparing this preferred surface active agent.

Some examples of other anionic surface active agents which may be employed in the present invention are alkyl taurate, alkyl phosphate, alkyl sulfate, alkyl sulfonate, and alkyl aryl sulfonate.

In the preferred form of the invention, acetylenic alcohols having an ethynyl hydrogen on the acetylenic group are employed as the acetylenic compound component. Some examples of acetylenic alcohols or compounds which may be employed in the present invention are: hexynol, dimethylhexynol, dimethylhexynediol, dimethyloctynediol, methylbutynol, methylpentynol, ethynyl cyclohexanol, 2-ethylhexanol, phenylbutynol, and ditertiary acetylenic glycol. Other acetylenic compounds which can be employed in accordance with the present invention are for example, butynediol, 1-ethynylcyclohexanol, 3-methyl-1-nonyn-3-ol, 2-methyl-3-butyn-2-ol, also 1-propyn-3-ol, 1-butyn-3-ol, 1-pentyn-3-ol, 1-heptyn-3-ol, 1-octyn-3-ol, 1-nonyn-3-ol, 1-decyn-3-ol, 1-(2, 4, 6-trimethyl-3-cyclohexenyl) -3-propyne-1-ol, and in general acetylenic compounds having the general formula ##SPC1##

wherein R is an alkyl, phenyl, substituted phenyl or hydroxyalkyl radical or --H, and the alpha R's may be joined together to form a cyclohexyl ring.

Acetylenic sulfides having the general formula

Hc .tbd. c--r--s--r--c .tbd. ch

can also be employed in the present invention in lieu of the acetylenic alcohols. Examples of these are diproparagyl sulfide, bis (1-methyl-2-propynyl) sulfide and bis (2-ethynyl-2-propyl) sulfide.

The non-acetylenic alcohols suitable for use in the present invention have the general formula ROH, wherein R is either an alkyl group or a ketone group. Some examples of these alcohols are diacetone alcohol, normal propanol, isopropanol, ethanol, methanol, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, and 1-5-pentanediol.

The nitrogen or ammonia base compounds that may be employed in accordance with the present invention are those amines such as mono-, di- and trialkyl amines having from two to six carbon atoms in each alkyl moiety, as well as the six-membered n-heterocyclic amines, for example alkyl pyridines and mixtures thereof. These compounds include such amines as ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, tripropylamine, mono-, di-, and tributylamine, mono-, di-, and tripentylamine, mono-, di-, and trihexylamine, and isomers of these, such as isopropylamine, tertiary butylamine, etc. The suitable nitrogen compounds also include alkyl pyridines having from one to five nuclear alkyl substituents per pyridine moiety, with such alkyl substituents having from one to 12 carbon atoms. The pyridines are preferred which have an average of six carbon atoms per pyridine moiety, e.g., a mixture of high boiling tertiary-nitrogen-heterocyclic compounds such as HAP (high alkyl pyridines), Reilly 10-20 base and alkyl pyridines HB.

The aldehydes which may be used in accordance with the present invention include alkyl aldehydes, aryl aldehydes, alkylaryl aldehydes. The aldehydes may be substituted with non-deleterious substituents, such as hydroxyl group, and may be saturated or unsaturated. Suitable aldehydes include formaldehyde, benzaldehyde, butyraldehyde, B-hydroxybutyraldehyde (aldol) propionaldehyde and glyoxal. The aldehyde may be used alone or in a suitable solvent such as alcohol.

Anionic surface active agents of this invention are generally not compatible with the other compounds employed in the corrosion inhibiting composition. Therefore, the corrosion inhibitor composition should be made up in two parts, the first part composed of the anionic surface active agent, and the second part composed of the acetylenic compound, or a blend of the acetylenic compound and the other compounds disclosed above. The acid solution containing the corrosion inhibitor composition may then be prepared by preparing the desired acid solution, then combining the surface active agent with the acid solution and mixing it thoroughly, and then combining the acetylenic compound or blend of acetylenic compound and other compounds with the acid solution and mixing thoroughly. Another method for preparing an acid solution containing the corrosion inhibitor composition of the present invention is to combine the surface active agent with a proper amount of water stirring it thoroughly, then combining the acetylenic compound or blend of acetylenic compound and other compounds with the water and stirring it thoroughly, and thereafter combining a proper amount of acid to complete the desired acid solution.

On a basis of a volume of 100 per cent, a preferred composition of the present invention is comprised as follows:

Per Cent Anionic Surface Active Agent 15-35 Acetylenic Compound 65-85

Another preferred composition of the present invention is comprised as follows:

Per Cent - Anionic Surface Active Agent 15-35 Acetylenic Compound 30-60 Nitrogen Compound 0-8 Non-acetylenic Alcohol 10-50

Yet another preferred composition of the present invention is comprised as follows:

Per Cent Anionic Surface Active Agent 15-35 Acetylenic Compound 30-60 Nitrogen Compound 0-8 Aldehyde 10-30 Non-acetylenic alcohol 5-15

The non-acetylenic alcohol not only acts as a diluent and/or solubilizer, but also contributes to the corrosion inhibiting effectiveness of the novel composition for some applications. The nitrogen compound also contributes to the corrosion inhibiting effectiveness of the novel composition for some aluminum alloys as does the aldehyde.

On a basis of a volume of 100 per cent, a more specific preferred composition, sometimes referred to herein as composition A, of the present invention is as follows:

Composition A Compound Parts by Per Cent Volume By Volume ______________________________________ CRA 1.0 30.0 Ethyl Octynol 2.33 70.0 ______________________________________

Another preferred specific composition, sometimes referred to herein as composition B is as follows:

Composition B Compound Parts by Per Cent Volume By Volume ______________________________________ CRA 1.0 30.0 Ethyl Octynol 1.6 49.0 Diacetone Alcohol 0.7 21.0 ______________________________________

Yet another preferred composition, sometimes referred to herein as composition C is as follows:

Composition C Compound Parts by Per Cent Volume By Volume ______________________________________ CRA 1.00 25.0 Propargyl Alcohol 1.38 34.4 Ethyl Octynol 0.14 3.4 Alkyl Pyridines HB 0.11 2.8 Diacetone Alcohol 1.38 34.4 ______________________________________

Still another preferred composition, sometimes referred to herein as Composition D is as follows:

Composition D - Compound Parts by Per Cent Volume By Volume ______________________________________ CRA 1.00 25.00 Propargyl Alcohol 1.36 33.94 Ethyl Octynol .51 12.73 Alkyl Pyridines HB .11 2.87 Formaldehyde (55%) in Methanol .60 15.00 Diacetone Alcohol .42 10.46 ______________________________________

A further preferred composition of the present invention, sometimes referred to herein as composition E is as follows:

Composition E - Compound Parts by Per Cent Volume By Volume ______________________________________ CRA 1.00 25.0 Propargyl Alcohol 1.38 34.4 Ethyl Octynol 0.14 3.4 Alkyl Pyridines HB 0.11 2.8 Diacetone Alcohol 0.41 10.3 Normal Propanol 0.96 24.1 ______________________________________

A number of laboratory tests were conducted wherein the preferred blends of this invention, compositions A, B. C, D, and E, were tested at various temperatures, in various amounts with various aluminum alloys, under static conditions and dynamic conditions, in various hydrochloric acid solutions.

PROCEDURE FOR STATIC TESTS

In these tests, the acid solutions were mixed by diluting 20° Be' HCL with water to the desired concentrations. A portion of each acid solution was then titrated with a standard base solution to ascertain the exact acid concentration. The various acid solutions were prepared in advance in sufficient quantities to complete an entire series of tests with the same batch of acid. Corrosion coupons of various types of aluminum were ordered in sufficient quantities to complete a series of tests on the same batch of coupons. The coupons were cleaned as follows: Scrubbed by hand with a fine nylon brush in a detergent containing a pumice, rinsed, dipped in acetone to remove the access water and then dipped in alcohol and allowed to dry. They were then weighed to the nearest milligram and stored in a desiccator until time for use.

Tests were conducted at various temperatures.

The acid solution was poured into glass bottles in sufficient quantity to approximate the specific acid volume to coupon surface area ratio that was desired. The quantity of acid used was dependent upon the surface area of the coupon to be tested. In most of the static tests, a 25 cc./in.2 acid volume to coupon surface area ratio was used. After the desired amount of acid was poured into the bottles, the inhibitor composition was added with a hypodermic syringe, with the anionic surface active agent being added first separately and stirred with a glass rod, and then the other compounds in the particular inhibitor composition tested added and stirred with a glass rod. The inhibited acid solution was then placed in a water bath which had been set at a predetermined temperature and allowed to pre-heat for 20 minutes. After this time, the coupons were placed in the preheated inhibited acid solutions. The coupons were left in the acid solutions for the specified test time, then removed, neutralized, recleaned, rinsed, dipped in acetone and then alcohol, allowed to dry, and then reweighed.

PROCEDURE FOR DYNAMIC TESTS

The acid solutions in these tests were mixed and titrated in the same manner as outlined above for the static tests. In these tests 1 inch OD aluminum alloy tubing was cut into test specimens each measuring 6 inches. The specimens were cleaned by scrubbing by hand with a fine Nylon brush and a detergent containing pumice, rinsed, dipped in acetone to remove the excess water, and then placed in a desiccator and allowed to come to room temperature. The specimens were then weighed to the nearest milligram and stored in a desiccator until time for use.

The scaled specimens which had been pre-weighed to the nearest milligram were prepared by stopping up one end of the specimen and filling the specimen with a scaling solution. The scaling solution was calcium bicarbonate solution prepared by reacting a ten per cent calcium chloride solution with a sixteen per cent ammonium bicarbonate solution. The specimens containing the sealing solutions were then placed in an oven set at a temperature of 200°F. The scaling solution was allowed to evaporate leaving a calcium carbonate scale on the test specimens. The scaled specimens were then re-weighed to the nearest milligram and stored in a desiccator until time for use. All of these tests were conducted in a closed acid circulating system which had been calibrated to a desired velocity of acid flow.

The acid solution was poured into a glass bottle in sufficient quantity to approximate the specific acid volume-to-specimen surface area ratio that was desired. In most of these tests a 123 cc./in.2 volume to specimen surface area ratio was used. After the desired amount of acid was poured into the bottles, the inhibitor was added with a hypodermic syringe, the anionic surface active agent being combined first and stirred with a glass rod, and then the other compounds in the composition tested were combined and stirred.

The flow rate of the system was calibrated by using a flow meter to measure flow and a variable resistor to regulate the speed of a circulating pump. The temperature of the acid solution was maintained at the desired temperature for each test by use of a hot plate which was controlled with a Tele-Thermometer. The specimens were exposed to the circulating acid solution for the specified time, then removed, neutralized, cleaned, rinsed, dipped in acetone, allowed to dry, and then reweighed.

In both the static tests and dynamic tests the loss in weight of the coupons and/or specimens was multiplied times a calculated factor to convert the loss in weight to lbs./ft.2 /24 hrs. The factor was calculated as follows: ##SPC2##

Example: Test time, 6 hours, surface area of coupon 4.0 in.2 then

144/454 × 4.0 × (6/24) = 0.317 lb./ft.2 /day

The results of these tests are set forth below:

TABLE I ______________________________________ COMPARISON OF VARIOUS ANIONIC ______________________________________ SURFACE ACTIVE AGENTS ______________________________________ Type of Test Static Test Temperature 125° F. Test Time 4 hrs. Metal Type Aluminum Alloy-3003 Corrodent 5% HCl Pressure Atmospheric Acid Volume-Surface Area Ratio: 25 cc./in.2 ______________________________________ Inhibitor Volume Per Cent Corrosion Concentration Rate in Lbs./Ft.2 of Inhibitor /day ______________________________________ None None 0.775 CRA 0.1 0.368 Composition D .4 0.004 Alkyl Taurate 0.1 0.097 Alkyl Phosphate 0.1 0.124 Alkyl Sulfate 0.1 0.136 Composition D w/ Alkyl Taurate in lieu of CRA 0.4 0.025 Composition D w/ Alkyl Phosphate in lieu of CRA 0.4 0.072 Composition D w/ Alkyl sulfate in -lieu of CRA 0.4 0.008 ______________________________________

From the above Table it can be seen that best results were obtained with CRA in composition D.

TABLE II __________________________________________________________________________ COMPARISON OF VARIOUS ACETYLENIC ALCOHOLS AND C13 H27 SO3 Na (CRA) MIXTURES WITH COMPOSITION __________________________________________________________________________ Type of Test Dynamic Test Temp. 150°F. Test Time 6 hours Metal Type Aluminum Alloy-3003 H14 Corrodent 5% HCl Velocity 1 ft./sec. Pressure Atmospheric Surface Active Agent CRA Acid Volume - Surface Area Ratio 123cc/in.2 __________________________________________________________________________ Volume Volume Volume Per Cent Per Cent Per Cent Concentration Concentration Concentration Corrosion Acetylenic of CRA Surface of Acetylenic of Total Rate in Active Agent Alcohol Inhibitor Lbs./Ft.2 Composition /Day __________________________________________________________________________ Propargyl Alcohol 0.3 0.7 1.0 0.0087 Methyl Butynol 0.3 0.7 1.0 0.0860 Hexynol 0.3 0.7 1.0 0.0066 Composition A 1.0 0.0016 __________________________________________________________________________

As can be seen from the above data Composition A achieved the best result but relatively good results were also achieved with the other acetylenic alcohols tested.

TABLE III ______________________________________ INHIBITOR COMPOSITION B-CORROSION RATES FOR VARIOUS ACID STRENGTHS AND TEMPERATURE ______________________________________ Type of Test Dynamic Test Time 6 Hours Metal Type Aluminum Alloy-3003 H14 Velocity 1 ft./sec. Pressure Atmosphere Acid Volume-Surface Area Ratio: 123cc./in.2 ______________________________________ Volume Per Cent Corrodent Test Corrosion Concentration (Volume Temp. Rate in Lbs. Composition B Per Cent) (°F.) /ft.2 /day ______________________________________ 1.0 5% HCl 150 0.0014 1.0 71/2% HCl 150 0.0019 1.0 10% HCl 150 0.0076 1.0 5% HCl 175 0.0023 1.0 71/2% HCl 175 0.0056 1.0 10% HCl 175 0.0072 ______________________________________

Two specimens were subjected to the scaling process described above for the purpose of determining the amount of corrosion caused by scaling alone. After the scale was laid down on two specimens it was removed by brushing the specimens with a soft brush in warm water. The specimens were weighed before scaling and after the scale had been removed in order to determine weight loss due to the scale. Table IV shows the results of these tests.

Corrosion tests were conducted with inhibitor composition B in 5 per cent, 71/2 per cent and 10 per cent hydrochloric acid solutions at 150°F. on specimens that contained a calcium carbonate scale layed down on the specimens as described above. These tests were conducted to determine if the inhibitor system would protect the aluminum surface once the scale had been removed by the acid. Table V reflects the results of these tests. The corrosion rates reported in this table have been corrected to reflect only the amount of corrosion that occurred from the acid solutions. The average weight loss from the scaling process reflected in Table IV was deducted from the weight loss obtained with scaled specimens contacted by the acid solutions so that the reported corrosion rates in Table V reflect only the corrosion resulting from the inhibited acid solutions.

TABLE IV ______________________________________ CORROSION OF SPECIMENS DUE TO SCALING ______________________________________ Metal Type Aluminum Alloy-3003H14 Original Final Wt. Average Wt. Specimen Wt. in Wt. in Loss In Loss In Grams Grams Grams Grams ______________________________________ No. 1 51.800 51.791 0.009 No. 2 51.757 51.750 0.007 0.008 ______________________________________

TABLE V __________________________________________________________________________ INHIBITOR COMPOSITION B CORROSION OF SCALED SPECIMENS Type of Test Dynamic Test Temp. 150°F. Test Time 6 hours Metal Type Aluminum Alloy-3003 H14 containing a CaCO3 Scale Acid Velocity 1 ft./sec. Pressure Atmospheric Acid Volume-Surface Area Ratio: 123 cc./in.2 __________________________________________________________________________ Volume Per Cent Concentration Corrodent Weight of Corrosion Rate of (Volume CaCO3 Scale in Lbs./Ft.2 Composition B Per Cent) in Grams /Day __________________________________________________________________________ 1.0 5% HCl 5.896 0.0037 1.0 71/2% HCl 5.695 0.0064 1.0 10% HCl 5.821 0.0095 __________________________________________________________________________

As can be seen by comparing Table III with Table IV very little additional corrosion took place as a result of the calcium carbonate scale, and the inhibitor system was very effective in protecting the aluminum specimen surface once the scale had been removed by the corrodent.

TABLE VI ______________________________________ INHIBITOR COMPOSITION C- CORROSION RATES FOR VARIOUS ALUMINUM ALLOYS Type of Test Static Test Temp. 125°F. Test Time 4 hours Corrodent 5% HCl Pressure Atmospheric Acid Volume-Surface Area Ratio: 25 cc./in.2 ______________________________________ Volume Per Cent Corrosion Aluminum Concentration Rate in Lbs. of Composition C /Ft.2 /Day ______________________________________ AA-179 (Cast) None 0.820 AA-179 (Cast) 0.4 0.006 AA-1100 None 2.135 AA-1100 0.4 0.003 AA-2011 None 1.212 AA-2011 0.4 0.013 AA-2017 None 2.840 AA-2017 0.4 0.004 AA-2024 None 1.145 AA-2024 0.4 0.004 AA-2117 None 3.121 AA-2117 0.4 0.005 AA-3003 None 0.775 AA-3003 0.4 0.001 AA-4043 None 2.870 AA-4043 0.4 0.006 AA-5005 None 0.298 AA-5005 0.4 0.000 AA-5052 None 0.608 AA-5052 0.4 0.001 AA-5056 None 1.300 AA-5056 0.4 0.007 AA-6053 None 0.094 AA-6053 0.4 0.004 AA-6061 None 1.323 AA-6061 0.4 0.000 AA-6063 None 0.626 AA-6063 0.4 0.002 ______________________________________

TABLE VII ______________________________________ INHIBITOR COMPOSITION D-CORROSION RATES FOR VARIOUS ALUMINUM ALLOYS Type of Test Static Test Temp. 125°F. Test Time 4 hours Corrodent 5% HCl Velocity 3.065 ft/sec. Pressure Atmospheric Acid Volume-Surface Area Ratio: 181 cc./in.2 ______________________________________ Volume Type of Per Cent Corrosion Aluminum Concentration Rate in Lbs. of Composition D /Ft.2 /Day ______________________________________ AA-3003 None Completely Dissolved AA-3003 .55 0.015 AA-5005 None 1.07 AA-5005 .55 0.0008 AA-6061 None Completely Dissolved AA-6061 .55 0.013 ______________________________________

TABLE VIII __________________________________________________________________________ INHIBITOR COMPOSITION E-CORROSION RATES FOR VARIOUS ALUMINUM ALLOYS BY VARIOUS ACID SOLUTIONS AT VARIOUS TEMPERATURES Type of Test Static Test Time 4 hours Pressure Atmospheric Acid Volume-Surface Area Ratio: 25 cc./in.2 __________________________________________________________________________ Volume Per Cent Corrodent Concentration Corrosion Type of Test (Volume of Rate in Lbs. Aluminum Temp. Per Cent) Composition E /ft. 2 /Day __________________________________________________________________________ AA-3003 125°F. 5% HCl 0.4 0.001 AA-5005 125°F 5% HCl 0.4 0.001 AA-3003 125°F. 7.5% HCl 0.4 0.002 AA-5005 125°F. 7.5% HCl 0.4 0.002 AA-3003 125.20 F. 10% HCl 0.4 0.002 AA-5005 125°F. 10% HCl 0.4 0.002 AA-3003 150°F. 5% HCl 0.4 0.001 AA-5005 150°F. 5% HCl 0.4 0.001 AA-3003 150°F 7.5% HCl 0.4 0.002 AA-5005 150°F. 7.5% HCl 0.4 0.002 AA-3003 150°F. 10% HCl 0.4 0.002 AA-5005 150°F. 10% HCl 0.4 0.002 ________________________________
TABLE IX COMPARISON OF INHIBITOR COMPOSITIONS A AND B Type of Test Dynamic Test Temp. 150°F. Test Time 6 hours Corrodent 5% HCl Metal Type AA-3003 Pressure Atmospheric Acid Volume-Surface Area Ratio: 123 cc/in.2 ______________________________________ Volume Per Cent Inhibitor Concentration Corrosion Rate Composition of Inhibitor in Lbs/Ft2 /Day Composition ______________________________________ A 1.0 0.0016 B 1.0 0.0014 ______________________________________

As can be seen from the above data the particular composition of the present invention which should be used for a particular application to obtain the best protection depends on the aluminum alloy to be protected, the strength of the acid solution to be employed, and temperatures to be encountered.

TABLE X CORROSION RATES OF VARIOUS ACID SOLUTIONS WITH AND WITHOUT COMPOSITION D Type of Test Static Test Temp. 125°F. Test Time 4 hours Metal Tested AA-3003 Aluminum Pressure Atmospheric Acid Volume-Surface Area Ratio: 25 cc/in.2 ______________________________________ Volume Per Cent Concentration Corrodent Corrosion Rate of (Volume Per Cent) in Lbs/Ft2 /Day Composition D ______________________________________ 0 5% Sulfuric Acid 0.005 0.4 5% Sulfuric Acid 0.004 0 5% Acetic Acid 0.001 0.4 5% Acetic Acid 0.0008 0 5% Formic Acid 0.0008 0.4 5% Formic Acid 0.0008 0 5% Hydrofluoric Acid 1.11 0.4 5% Hydrofluoric Acid 1.06 ______________________________________

As can be seen from the above table Inhibitor Composition D afforded some protection to the aluminum samples tested when combined with the various acid solutions tested, with the exception of Formic Acid which is not very corrosive to aluminum without inhibition.

From the above it may be seen that the inhibitor or inhibitor compositions of the present invention are operable when employed at temperatures as high as 175°F. in various acid concentrations. The corrosion which does occur is substantially uniform regardless of temperatures encountered and alloys protected. The corrosion inhibitor compositions provide long term protection at small concentrations and are particularly effective on aluminum and the various alloys thereof.

Applications in which the inhibitor of the present invention is particularly useful include cleaning of aluminum tanks, heat exchangers, pipe, etc., and preventing corrosion of aluminum tanks or vessels which must contain quantities of dilute acid.

The inhibitor of the present invention is preferably added to the acid in amounts by volume from about 0.05 per cent to 20 per cent. The amount of inhibitor required and the specific inhibitor composition will vary with the temperatures to be encountered, the particular aluminum alloy to be protected, and the strength or concentration of the acid solution used. The first part of the inhibitor, that is, the anionic surface active agent, should be combined first and mixed, and then the acetylenic compound, or mixture of acetylenic compound and non-acetylenic alcohol, or mixture of acetylenic compound, nitrogen compound, and non-acetylenic alcohol or mixture of acetylenic compound, nitrogen compound, and aldehyde, should be combined and mixed. The inhibitor composition may be added either to the water before acid is added or directly to the acid soltuion.

Broadly, the present invention relates to a new and improved corrosion inhibitor or composition for reducing the corrosive effect of aqueous acids on aluminum and the various alloys thereof consisting essentially of an anionic surface active agent and an acetylenic compound, or an anionic surface active agent and a synergistic blend of either an acetylenic compound and non-acetylenic alcohol or an acetylenic compound, a nitrogen or ammonia base compound and a non-acetylenic alcohol or aldehyde, in certain amounts of each.

 


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AQUEOUS SOLUTIONS OF INORGANIC MINERAL ACIDS ARE INHIBITED AGAINST THEIR CORROSIVE TENDENCIES BY THE ADDITION THERETO OF FROM 0.001 TO 2% BY VOLUME OF A COMPOSITION COMPRISING: (A) A MANNICH REACTION CONDENSATION PRODUCT FORMED BY REACTING ONE MOLE OF HYDROABIETYL AMINE WITH TWO MOLES OF FORMALDEHYDE AND TWO MOLES OF AN ALDEHYDE CONTAINING FROM TWO TO SIX CARBON ATOMS AND AT LEAST ONE HYDROGEN ATOM ON THE CARBON ATOM ADJACENT TO THE ALDEHYDIC CARBONYL CARBON ATOM, AND (B) AN ACETYLENIC ALCHOL WHICH CONTAINS THREE TO TWELVE CARBON ATOMS WITH THE RATIO OF A:B BEING WITHIN THE RANGE OF FROM 5:1 TO 1:5.

United States Patent O 3,585,136 CORROSION INHIBITION OF AQUEOUS SOLU- TIONS OF INORGANIC MINERAL ACIDS James R. Stanford, Houston, Tex., assignor to Nalco Chemical Company, Chicago, Ill. N Drawing. Filed Mar. 4, 1968, Ser. No. 709,918 Int. Cl. Clld 7/08 U.S. Cl. 252--8.55 7 Claims ABSTRACT OF THE DISCLOSURE Aqueous solutions of inorganic mineral acids are inhibited against their corrosive tendencies by the addition thereto of from 0.001 to 2% by volume of a composition comprising:

(A) A Mannich reaction condensation product formed by reacting one mole of hydroabietyl amine with two moles of formaldehyde and two moles of an aldehyde containing from two to six carbon atoms and at least one hydrogen atom on the carbon atom adjacent to the aldehydic carbonyl carbon atom, and

(B) An acetylenic alcohol which contains three to twelve carbon atoms with the ratio of A:B being within the range of from 5:1 to 1:5.

INTRODUCTION The present invention is directed to providing inhibited acid solutions whereby their aggressiveness toward ferrous metals is substantially reduced.

Mineral acid solutions are used in numerous industrial applications. They are used in cleaning of metals and in processes wherein they contact a variety of ferrous metals.

A particularly corrosive use of mineral acids is the employment of solutions and, in some instances, even more concentrated solutions of hydrochloric acid in oil well acidizing applications. Due to the excessive temperatures encountered in the lower levels of many oil wells the acid solutions are elevated to excessive temperatures, thereby greatly increasing their corrosiveness to ferrous metals. In such acidizing treatments it is not uncommon for the temperatures of the acid solutions to be raised to between ISO-300 F.

In recent years the art has developed a number of inhibitors in an attempt to reduce the corrosive tendencies of acids such as hydrochloric towards ferrous metals. A common type of inhibitor used either alone or in combination with other chemicals are the acetylenic alcohols such as propargyl alcohol and 4-ethyl-l-octyn-3-ol. The use of this latter alcohol is described in US. 3,249,548.

While the acetylenic alcohols have proven to be of some value in reducing the corrosive tendencies of hydrochloric acid solutions at elevated temperatures, their use is not entirely satisfactory. At effective levels their cost is prohibitive. Also they are not completely effective when the temperature of the acid solutions is in excess of 150 F.

If it were possible to improve the effectiveness of acetylenic alcohols whereby they could be used in small amounts and yet at the same time provide improved corrosion inhibition, a major advance would be afforded to the art.

OBJECTS OF THE INVENTION It therefore becomes an object of the invention to provide improved acetylenic alcohol containing compositions for use in rendering aqueous solutions of inorganic mineral acids noncorrosive.

Another object of the invention is to provide corrosion inhibitors for hydrochloric acid which are effective in ice preventing corrosion of ferrous metals in contact with such solutions whose temperature has been elevated to F. and above.

Other objects will appear hereinafter.

THE INVENTION In accordance with the invention it has been found that aqueous solutions of inorganic mineral acids particularly hydrochloric acid solutions may be inhibited against their corrosive tendencies toward ferrous metals by adding thereto novel compositions of the invention whereby inhibited mineral acid aqueous solutions are pro- Vided.

In its simplest embodiment the invention comprises using in combination the Mannich reaction products of a hydroabietyl amine, formaldehyde, and certain aliphatic aldehydes in combination with an acetylenic alcohol which contains from 3 to 12 carbon atoms.

The Mannich reaction products are combined with the acetylenic alcohols to provide a weight ratio within the range from 5:1 to 1:5. In a preferable embodiment of the invention the weight ratio of Mannich reaction products to acetylenic alcohols is within the range of 3:1 to 1:3 and, most preferably, 1:1 to 1:3.

The compositions of the type described above are added to aqueous solutions of mineral acids to provide on a volume basis from .001 to 2% by volume although, in most instances, dosages between 0.005 to 1% by volume give adequate results. This dosage is based on the volume of the total solution. The invention further contemplates finished corrosion inhibiting compositions utilizing the Mannich reaction products and acetylenic alcohols as described above in combination with oil soluble dispersants having nonionic or anionic characteristics. Such blends are further utilized in combination with an organic solvent-most preferably, a petroleum derived organic solvent such as a highly aromatic petroleum fraction.

When such corrosion inhibiting compositions are employed, they may be combined to provide finished products having the following general compositions as set forth below in General Formula I.

General Formula I Ingredients: Percent by weight Mannich reaction products and acetylenic alcohol (wt. ratio5:l to 1:5) 10-30 Oil soluble dispersant 5-40 Organic solvent Balance MANNICH REACTION PRODUCTS where in the above formula R is a hydroabietyl radical; R and A are radicals from the group consisting of hydrogen and lower aliphatic hydrocarbon groups with the total number of carbon atoms in A+R being not greater than 4.

In order to be capable of entering into the Mannich reaction, the aldehyde must contain at least 1 hydrogen atom on the carbon atom adjacent to the aldehydic carbonyl carbon atom. The Mannish reaction is described in greater detail in Introduction to Organic Chemistry, Condon & Meislich, Holt, Rinehart & Winston, Inc., New York (1961).

ACETYLENIC ALCOHOLS The acetylenic alcohols include those alcohols containing the acetylenic grouping and contain from 3-12 carbon atoms. The preferred alcohols used in the practices of this invention are propargyl alcohol and, most preferably, 4- ethyl-1-octyn-3-ol. Other alcohols suitable for use in preparing the compositions of the invention come within the following structural formula:

n noc czcn wherein R is H, alkyl or phenyl and R is H or lower alkyl.

Alcohols of the above type are set forth in US. 3,049,- 496, the disclosure of which is incorporated herein by reference.

THE OIL SOLUBLE DISPERSANTS The oil soluble dispersants used in preparing finished inhibitor products are most preferably oil soluble or at least oil dispersible. They are either anionic .or non-ionic at use levels. The non-ionic products are prepared by reacting fatty acids, alcohols, alkyl phenols and the like with between 50 moles of either ethylene or propylene oxide.

Preferred chemicals of this type are the alkyl phenols or fatty acids which have been reacted with from between 5-25 moles of ethylene oxide.

Fatty acids per se, e.g. C12-C22 fatty acids, may be used as well as the polymerized diethanoid fatty acids which form dimers and trimers and mixtures thereof upon polymerization. See particularly US. 2,482,761 and 2,763,612. When the fatty acids are used alone it is desirable that they be used as the free acid rather than as their soaps or salts.

The oil soluble dispersants of the types described above when used in preparing corrosion inhibiting compositions tend to improve the operability of the Mannich reaction products in combination with the acetylenic alcohol. They allow the alcohol, particularly the higher alcohols, to be dissolved or dispersed into the mineral acid. They perform a similar function with respect to Mannich reaction products. They are also important in that they provide a better wetting of the inhibitor on the metal surfaces sought to be protected.

THE ORGANIC SOLVENTS Many of the well-known organic solvents can be used to dissolve the above-described ingredients. Preferably these solvents are petroleum base solvents and contain at least by weight of aromatic constituents. Thus, such well-known fractions as aromatic oils, Stoddard solvents, naphthas and the like may be utilized. Generally those aromatic solvents having a boiling point above that of gasoline but below that of lubricating oils are satisfactory.

Other well-known organic solvents that may be used are for instance, benzene, toluene, xylene, dimethylformamide, dimethylsulfoxide and the like.

THE EVALUATION OF THE INVENTION Listed below are typical compositions of the invention; Compositions I through III and IX and X are Mannich reaction products.

EXAMPLE I Composition 1 Gms.

Rosin amine D 1 Muriatic acid (30% HCl) 3O Isopropanol (99%) Formalin (37%) 80 Acetaldehyde 88 1 Hydroabietyl amine.

The above were added to a three necked flask and heated between 60 and 70 C. for 4 hours to yield the finished product.

EXAMPLE II Composition 2 Gms.

Rosin amine D 17 Muriatic acid 6 Isopropanol (99%) 50 Formalin (37%) 8 Acetaldehyde 9 1 Hydroabietyl amine.

The above were added together to a Fisher Pressure bottle in the order listed, sealed and mounted on a revolving wheel at F. for 16 hours.

EXAMPLE III Composition 3 Gms. Rosin amine D 1 9 Muriatic acid 3 Isopropanol 50 Formalin (37%) 8 Acetaldehyde 9 Ilydroabietyl amine.

The above were added together to a Fisher Pressure bottle and mounted on the wheel for 24 hours at 160 F.

Composition 4 Gms. Composition 2 20 Nonyl phenol+l2 moles ethylene oxide 30 Crude tall oil 20 Propargyl alcohol 10 Composition 5 Composition 3 40 Nonyl phenol+l2 moles ethylene oxide 20 Crude tall oil 30 Propargyl alcohol l0 Composition 6 Composition 2 20 Nonyl phenol+l2 moles ethylene oxide 15 Tall oil+15 moles ethylene oxide 15 Crude tall oil 4O Propargyl alcohol 10 Composition 7 Composition 2 30 Nonyl phenol+l2 moles ethylene oxide 15 Tall oil-|-1S moles ethylene oxide 15 Crude tall oil 30 Propargyl alcohol 1O Composition 8 Composition 2 12 Nonyl phenol+l2 moles ethylene oxide 7 Tall oil+15 moles ethylene oxide 8 Crude tall oil 20 Propargyl alcohol 2 EXAMPLE IV Composition 9 Gms. Rosin amine D 1 51 Muriatic acid 18 Isopropanol (99%) 25 Formalin (37%) 24 Acetaldehyde 27 1 Hydroabieltyl amine.

The above was added to a Fisher Pressure bottle and mounted on a revolving wheel at 160 F. for 72 hours.

EXAMPLE V Composition 10 Gms. Rosin amine D 1 34 Muriatic acid 12 Isopropanol (99%) 25 Formalin (37%) 40 Acetaldehyde 40 1 Hydroabietyl amine.

The above were added to a Fisher Pressure bottle and mounted on the wheel for 72 hours.

Composition 11 Gms.

Composition 9 67 Isopropanol (99%) 62 Composition 12 Gms.

Composition 11 30 Aromatic solvent 50 Octynol 2 1O Nonyl phenol-H2 moles ethylene oxide 10 Composition l3 Gms.

Composition 11 20 Tall oil+l5 moles ethylene oxide 15 Nonyl phenol-[-12 moles ethylene oxide 15 Crude tall oil Aromatic solvent 20 Octynol 10' Composition 14 Gms.

Composition 13 80 Polyamine bottoms 20 Composition 1-5 Gms.

Composition 13 80 Dimer and trimer fatty acids-still bottoms 20 Composition 16 Gms.

Composition 13 80 Sulfurized tall oil 20 Composition 17 Gms.

Composition 13 80 Water 16 Composition 18 Gms.

Composition 13 80 Dimer and trimer fatty acids-still bottoms 20 6 Composition 19 Gms. Composition 11 20 Nonyl phenol-H2 moles ethylene oxide 15 Tall oil+15 moles ethylene oxide 15 Aromatic solvent 40 Octynol 5 Aromatic solvent 15 4-ethy1-Loctyn-3-o1.

Composition 20 Gms. Composition 11 30 Aromatic sol-vent 50 Octynol 10 Nonyl phenol+12 moles ethylene oxide 1O 2 4-etliyl-1'octyn-3-o1.

Composition 21 Gms. Composition 9 20 Nonyl phenol+12 moles ethylene oxide 15 Tall oil+15 moles ethylene oxide 15 Crude tall oil 20 Aromatic solvent 20 Octynol 2 10 11 4-ethyl-l-octyn-3-ol.

Composition 22 Gms. Composition 9 10 Tall oil+ 15 moles ethylene oxides 25 Nonyl phenol+ 12 moles ethylene oxide 15 Crude tall oil 20 Aromatic solvent 20 Octynol 2 10 4-ethyl-Loetyn-3-ol.

Composition 23 Gms. Composition 13 KI 5 Water 5 Composition 24 Gms. Composition 13 80 KI 10 Water 10 Composition 27 Gms. Composition 13 45 I-Iydroabietyl amines-i-S moles ethylene oxide+15% hydroabietyl amine CORROSION TESTS In the small scale laboratory tests which follow, three different types of ferrous metal specimens were used:

Specimens (1) High pressure steel tubing-American Petroleum Institute designation N80.

(2) Mild steel coupons SAE 1020 cold rolled steel.

(3) High carbon steel drill rod.

All tests used 15% HCl solutions as the test media.

No blank results are indicated since under the test conditions at temperatures in excess of the test specimens were completely destroyed.

In a series of tests corresponding to those hereinafter described the Mannich reaction products were evaluated and were found to be no better than the blank test results.

4-ethyl-1-octyn-3-ol was evaluated under the test conditions shown and the concentrations used in the test and in all instances gave 50% poorer results than the compositions of the invention.

Results of testing the various compositions of the invention are set forth below in Table I.

TABLE 1 Time, Temp, Specimen (n(-., Wt.

hrs F. ypigal. 1,000 loss, g

6 200 l 4 3. 0062 6 200 1 4 763 6 .300 l 2 1. 5123 6 201] 1 2 .2470 6 200 l 4 0. 5123 5 /2 201] 1 .2 J. 8084 5 200 l 4 U 5458 51/ 00 l .2 1. 4868 5 2 200 l 4 1. .2646 24 201i 1 1 Ill. 7465 .54 1200 l 4 l. 5616 ii 200 3 4 1 48.0 ti .300 3 4 1 -17. ('1 .100 3 4 1 60. 5 t) 200 3 1 1 76. ti 6 .200 3 4 1 6i). 4 6 200 3 1 1 til. 1 ti 200 3 4 1 (i7. 7 8 ZUU 3 4 1 Tti. 4 8 IOU 3 1 1 44. SI 8 200 3 4 1 37. 5 8 200 3 2 1 15. 4 18 200 3 1 1 7 .1. 0 18 200 3 .2 1 13,0 18 .100 3 l 1 612. l .100 3 2 1 11. 5 5 .300 3 1 1 35. 1 '2 2 l 1 U. 2047 2-1 7.! L. J 1 U. 167" 1 In milligrams.

C 0 NC LU SION While the tests have shown the compositions to be effective in inhibiting 15% hydrochloric acid, they are also effective in inhibiting the various strength hydrochloric acid solutions up to its saturation solubility. They are similarly effective in inhibiting solutions of phosphoric, sulfuric and nitric acids.

What is claimed is:

1. An aqueous solution substantially non-corrosive to ferrous metals which consists essentially of a major proportion of an inorganic mineral acid from the group con sisting of hydrochloric, phosphoric, sulfuric, and nitric acid and from 0.001 to 2% by volume of a composition consisting essentially of:

(A) the Mannich reaction condensation product of one mole of a hydroabietyl amine with at least two moles of formaldehyde and at least two moles of an aldehyde containing from 2 to 6 carbon atoms and having at least one hydrogen atom on the carbon atom adjacent to the aldehydic carbonyl carbon atom, and (B) a monohydroxy acetylenic alcohol which contains from 3 to 12 carbon atoms: with the ratio of A to B being within the range of from 5:1 to 1:5.

2. The aqueous solution of an inorganic mineral acid as set forth in claim 1 where the mineral acid is hydrochloric.

3. The aqueous solution of an inorganic mineral acid as set forth in claim 1 wherein R and A are hydrogen and the acetylenic alcohol is 4-ethyl-l-octyn-3ol.

4. The aqueous solution of an inorganic mineral acid as set forth in claim 3 wherein the ratio of A to B is within the range of from 3:1 to 1:3.

5. The aqueous solution of an inorganic mineral acid as set forth in claim 4 wherein the ratio of A to B is within the range of 1:1 to 1:3.

6. A composition useful in inhibiting the corrosive tendencies of aqueous solutions of inorganic mineral acids from the group consisting of hydrochloric, phosphoric, sulfuric, and nitric acid, which consists essentially of from 10% to 30% by weight of a composition consisting essentially of:

(A) the Mannich reaction condensation product of one mole of hydroabietyl amine with at least two moles of formaldehyde and at least two moles of an aldehyde containing from 2 to 6 carbon atoms and having at least one hydrogen atom on the carbon atom adjacent to the aldehydic carbonyl carbon atom, and

(B) a monohydroxy acetylenic alcohol which contains from 3 to 12 carbon atoms;

with the ratio of A to B being within the range of from 5:1 to 1:5, 5-40% by weight of an oil soluble dispersant formed by reacting higher fatty acids and higher alkyl phenols with 5-50 moles of an alkoxide from the group consisting of ethylene oxide and propylene oxide; the balance being a hydrocarbon solvent for the above ingredients having a boiling point above C.

7. The composition of claim 6 wherein R and A are hydrogen and the acetylenic alcohol is 4-ethy1-1-octyn-3- 01; and wherein the oil soluble dispersant is an ethoxylated nonyl substituted phenol which contains from 5-50 moles of reacted ethylene oxide.

References Cited UNITED STATES PATENTS 2,975,125 3/1961 Saukaitis et a1. 2528.55 3,077,454 2/1963 Monroe et a1. 252-8.55 CX 3,107,221 10/1963 Harrison et a1. 252-148 3,113,113 12/1963 Marsh et a1. 252-392 3,230,173 1/1966 Spivack 252148 3,249,548 5/1966 Herman et a1. 252-146X MAYER WEINBLATT, Primary Examiner A. I. RADY, Assistant Examiner US. Cl. X.R.

*zg ggg UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 585 l 36 Dated June 15 1971 Inventor-(s) James R. Stanford et al It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Column 5 Composition 12 should read as follows:

Gms. Composition I1 2O Nonyl phenol+12 moles ethylene oxide 15 Tall oil+l5 moles ethylene oxide l5 Aromatic solvent 40 Octynol 5 Aromatic solvent l5 4-ethyl--1 -octyn-3 -ol.

Column 6 Composition 19 should read as follows:

. Gms. Composition ll 30 Aromatic solvent 50 Octynol 1 0 Nonyl phenol+l2 moles ethylene oxide 10 4-ethyl-l octyn-3 -ol.

Signed and sealed this 11th day of January 1972.

(SEAL) Attest:

EDWARD M.FLETCHER,JR. ROBERT GOTTSCHALK J Attesting Officer Acting Commissioner of Patents

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HAI-OSTM Acid Inhibitor
Provides corrosion protection and meets environmental requirements in both standard
and weighted acid systems
ACIDIZING
HAL32881
Figure 2 - Standard 15% HCl with HAI-OS inhibitor e3ect on N-80.
HII-124B/HII-124F or HII-500M intensi4er was used as needed. Note
that corrosion loss was maintained well below the acceptable limit
of 05 lb/52 .
HAI-OSTM inhibitor is an environmentally friendly acid corrosion
inhibitor applicable to a broad range of temperatures, acid
mixtures, and mixing Euids. It provides exceptional performance
in both standard and weighted acids. Weighted acids are oHen
required in horizontal screened sections during mud Dlter-cake
cleanup or for wellhead pressure control.
HAI-OS inhibitor oFers several important beneDts:
• More environmentally acceptable.
• Ecotested according to OSPARCOM and EPA guidelines.
• Can be intensiDed with Halliburton's patented, environmentally
friendly HII-124B/ HII-124FTM intensiDer combination or
HII-500MTM intensiDer.
• Applicable in certain acid systems up to 180o
C (350o
F)
(see Figures 1, 2, and 3).
• EFective on various alloys including N-80, 13Cr, 316L and
Incoloy* 825.
• Provides excellent solubility in CaCl2, CaBr2, and ZnBr2
brine-acid systems with densities ranging from 10.0 lb/gal to
16.6 lb/gal over a broad temperature range.
Required performance plus environmental friendliness
Halliburton is committed to continuous improvements in chemical
compliance. Reducing the environmental impact of chemicals has
been balanced with tough performance requirements including the
move toward HPHT operations.
For completion and stimulation operations, signiDcant research
eFort has been focused on developing and using environmentally
friendly chemicals. Acidizing operations have presented a diGcult
challenge, especially in the area of acid corrosion inhibitors. It is an
almost impossible requirement that a product function in a harsh
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HAI-OS inhibitor is a signiDcant step toward meeting these
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HAI-OS does not contain environmentally unacceptable substances
such as ethyl octynol, naphtha, and quaternary ammonium
compounds. It has been classed in the UK as an (O)CNS Group C
chemical. For health and safety labeling, HAI-OS inhibitor should
be labeled toxic and Eammable.


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Basic Information
CAS No.: 5877-42-9
Name: 1-Octyn-3-ol, 4-ethyl-
Molecular Structure:
Molecular Structure of 5877-42-9 (1-Octyn-3-ol, 4-ethyl-)
Formula: C10H18O
Molecular Weight: 154.25
Synonyms: 4-Ethyl-1-octyn-3-ol;4-Ethyl-3-hydroxy-1-octyne;Ethyloctynol;NSC 62119;
EINECS: 227-545-9
Density: 0.878 g/cm3
Melting Point:
Boiling Point: 198.2 °C at 760 mmHg
Flash Point: 76 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes: 36/37/38
Safety: 26-36/37/39
Transport Information: UN 3267
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Product Name: 4-ETHYL-1-OCTYN-3-OL Synonyms: 4-Ethyl-1-Octyne-3-Ol;1-Octyn-3-ol, 4-ethyl-;4-ETHYL-3-HYDROXY-1-OCTYNE;4-ETHYL-1-OCTYN-3-OL 97+%;ETHYLOCTINOL;NSC 62119;TIMTEC-BB SBB005885;4-ethyl-1-octyn-3-o CAS: 5877-42-9 MF: C10H18O

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Octyl salicylate, or 2-ethylhexyl salicylate, is an organic compound used as an ingredient in sunscreens and cosmetics to absorb UVB (ultraviolet) rays from the sun.[1] It is an ester formed by the condensation of a salicylic acid with 2-ethylhexanol. It is a colorless oily liquid with a slight floral odor.

The salicylate portion of the molecule absorbs ultraviolet light, protecting skin from the harmful effects of exposure to sunlight. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water resistant) properties.

Notes
Skin cancer foundation: Understanding UVA and UVB
References
"The Skin Cancer Foundation's Guide to Sunscreens". Skin Cancer Foundation. 2011. Retrieved 15 November 2011.

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