composés de benzalkonium;sels de benzalkonium;Composés benzalkonium;BTC-2125; BTC2125; Chlorure d'alkyl-benzyl-diméthyl-ammonium; benzalkonium; chlorure de benzalkonium; Alkyl-benzyl-diméthyl-ammonium; Alkylbenzyldiméthylammonium; Chlorure d'alkylbenzyldiméthylammonium;benzalkonium chlorure;BTC-2125; BTC2125; Chlorure d'alkyl-benzyl-diméthyl-ammonium; benzalkonium; chlorure de benzalkonium; Alkyl-benzyl-diméthyl-ammonium; Alkylbenzyldiméthylammonium; Chlorure d'alkylbenzyldiméthylammonium;BZK; BKC; BAC; ADBAC; Benzalkonium chloride; Benzalkonium (C8-C16) chloride; C8-18-Alkylbenzyldimethylammonium chloride; alkyldimethylbenzylammonium chloride

Propriétés : le Chlorure de Benzalkonium est un agent de surface cationique de la famille des ammoniums quaternaires. 

Il s'agit d'une solution aqueuse facilement soluble dans l'Eau, l'Ethanol et l'Acétone.

Il élimine l’origine du verdissement dû aux mousses, algues et lichens sur la plupart des matériaux de construction. En plus de son action curative, il permet aussi de prévenir l'apparition de mousses, lichens, et algues sur les matériaux mal exposés.

Action préventive et curative.

Utilisable sur la plupart des matériaux.

Solution aqueuse hydrosoluble.

Protection longue durée.

S’utilise avec un pulvérisateur ou un arrosoir.

Produit biocide (TP2/10) : utilisez les biocides avec précaution ; avant toute utilisation, lisez l’étiquette et les informations concernant le produit.

Pureté : 50%

Numéro Cas : 68424-85-1

Numéro CE : 270-325-2

Synonymes (liste non exhaustive) : chlorure d'alkyldiméthylbenzylammonium, ADBAC (acronyme), chlorure de N-alkyle N,N-Diméthyle benzylammonium, chlorure d'alkylebenzyldiméthylammonium

Principaux synonymes

Noms français :

ALKYL DIMETHYL BENZYL AMMONIUM CHLORIDE

Chlorure d'alkyldiméthyl benzylammonium

Chlorure d'alkyldiméthylbenzylammonium

Chlorure d'alkylebenzyldiméthylammonium

Chlorure de benzalkonium

CHLORURE DE N-ALKYL DIMETHYL BENZYL AMMONIUM

Chlorure de N-alkyle (C8-C18) N,N-Diméthyle benzylammonium

CHLORURE DE N-ALKYLE N,N-DIMETHYLE BENZYLAMMONIUM

Noms anglais :

ALKYL (C8H17 TO C18H37)DIMETHYLBENZYL AMMONIUM CHLORIDE

ALKYL BENZYL DIMETHYL AMMONIUM CHLORIDE

ALKYL DIMETHYLBENZYL AMMONIUM CHLORIDE

ALKYLDIMETHYL(PHENYLMETHYL)QUATERNARY AMMONIUM CHLORIDE

ALKYLDIMETHYLBENZYLAMMONIUM CHLORIDE

Benzalkonium chloride

Benzylalkonium chloride

N-ALKYL DIMETHYL BENZYL AMMONIUM CHLORIDE

N-ALKYL(C8-C18) N,N-DIMETHYL BENZYLAMMONIUM CHLORIDE

N-ALKYL-N,N-DIMETHYLBENZYLAMMONIUM CHLORIDE

Utilisation et sources d'émission: Germicide, agent antiseptique

Chlorure de benzyl-décyl-diméthylazanium

Nom du produit chimique ou matériau: Benzalkonium Chloride

N° CAS: 63449-41-2

Formule moléculaire: C19H34ClN

Numéro MDL: MFCD00145757

Synonyme: benzyldimethyldecylammonium chloride, benzenemethanaminium, n-decyl-n,n-dimethyl-, chloride, benzenemethanaminium, n-decyl-n,n-dimethyl-, chloride 1:1, quaternary ammonium compounds, benzyl-c8-18-alkyldimethyl, chlorides, roccal, benzyl decyl dimethylazanium chloride, tret-o-lite xc 511, ccris 4586, benzyl decyl dimethylammonium chloride, c8-18-alkydimethylbenzyl ammonium chlorides

Informations sur la solubilité Miscible with water,acetone,ether and alcohol. Slightly miscible with benzene.

Chlorure de benzalkonium

Chlorure de benzalkonium

Image illustrative de l’article Chlorure de benzalkonium

Identification

No CAS: 8001-54-5

No ECHA 100.058.301 100.132.452, 100.058.301

No CE 269-919-4

Code ATC D08AJ01

D09AA11

Propriétés physiques

Solubilité Très soluble dans l'eau, l'alcool, l'acétone ;Presque insoluble dans l'éther ;1g d'anhydre dans 6ml de benzène, 100ml d'éther1

Masse volumique:0,9884 g·cm-3 (50 %, 20 °C)

Unités du SI et CNTP, sauf indication contraire.

modifier Consultez la documentation du modèle

Le chlorure de benzalkonium, aussi connu sous le nom de chlorure d'alkyldiméthylbenzylammonium et ADBAC, est un mélange de chlorures d'alkylbenzyldiméthylammonium avec des chaînes carbonées de longueur variable2. Ce produit est un agent de surface cationique de la famille des ammoniums quaternaires.

Propriétés physico-chimiques

Le chlorure de benzalkonium est facilement soluble dans l'éthanol et l'acétone. Bien que la dissolution dans l'eau soit lente, les solutions aqueuses sont plus faciles d'emploi et sont plus largement utilisées. Les solutions devraient être neutres à légèrement basiques avec une couleur allant de l'incolore au jaune pâle. Les solutions moussent fortement lorsqu'elles sont secouées1, ont un goût amer et ont une odeur d'amande détectable seulement dans les échantillons concentrés.

Utilisation

Les applications sont très variées, allant de la formulation de désinfectants à l'inhibition de « corrosion microbienne » dans le pétrole ou les huiles minérales3. Il est utilisé dans les produits pharmaceutiques tels que les solutions cutanées antiseptiques ou les lingettes. Il est utilisé comme conservateur dans les cosmétiques tels que les gouttes pour les yeux et le nez. On a reporté des cas de sensibilisations associées à l'utilisation continue et prolongée du produit. Il faut mettre des gants avant toute utilisation.

Avantages / inconvénients

En tant qu'antiseptique, il a l'avantage de ne pas brûler les plaies à l'application, contrairement aux antiseptiques à base d'éthanol ou d'eau oxygénée.

Il peut négativement interagir avec des matériaux notamment utilisés en milieu médical (silicones) ou avec l'hydrogel de certaines lentilles de contact.

Disponibilité

Les concentrés standard sont fabriqués sous forme de solutions à 50 et 80 %. Les solutions à 50 % sont purement aqueuses, tandis que les solutions plus concentrées requièrent l'incorporation d'additifs tels que des alcools, du polyéthylène glycol, etc. pour éviter l'augmentation de la viscosité ou la formation de gels à basse température.

Activité biologique

L'activité biocide la plus importante est associée aux dérivés alkylés en C12 à C14. On pense que le mécanisme bactéricide est dû à la disruption des interactions intermoléculaires. Ceci peut causer la dissociation des lipides dans la membrane cellulaire, ce qui compromet la perméabilité de la cellule et induit une fuite de son contenu. D'autres complexes biomoléculaires à l'intérieur de la cellule bactérienne peuvent aussi se dissocier. Les enzymes, qui contrôlent les activités respiratoires et métaboliques de la cellule, sont particulièrement susceptibles d'être désactivées.

Les solutions de chlorure de benzalkonium sont des agents bactéricides à action rapide et de durée modérément longue. Ils sont actifs contre certains protozoaires, virus, bactéries et fungi. Les spores des bactéries sont considérées comme résistantes. Les bactéries à Gram positif sont généralement plus sensibles que les Gram négatif. L'activité n'est pas grandement influencée par le pH, mais augmente aux températures élevées et avec la durée d'exposition.

De nouvelles formulations utilisant du benzalkonium mélangé à d'autres ammoniums quaternaires peuvent être utilisées pour étendre le spectre biocide et augmenter l'efficacité du désinfectant. Cette technique a été utilisée pour améliorer l'activité virucide.

L'utilisation d'excipients appropriés peut améliorer l'efficacité et les propriétés détergentes, et éviter la désactivation lors de l'utilisation. La formulation requiert beaucoup de soin car les solutions de benzalkonium peuvent être désactivées en présence de contaminants organiques et inorganiques. Les solutions sont incompatibles avec les savons, les nitrates1 et ne doivent pas être mélangées avec des surfactants anioniques. Les sels des eaux dures peuvent aussi réduire l'activité biocide. Comme pour tous les désinfectants, il est recommandé de traiter des surfaces sans saletés visibles.

Bien que des niveaux dangereux ne puissent être atteints dans les conditions d'utilisation normale, le benzalkonium et les autres détergents peuvent être néfastes aux organismes marins. Les désinfectants à base d'ammoniums quaternaires sont actifs à faible concentration, si bien que des doses excessives devraient être évitées.

Le chlorure de benzalkonium a aussi une activité spermicide.

Sécurité

Le chlorure de benzalkonium est extrêmement toxique pour les invertébrés aquatiques (CL50 = 5,9 μg ai/L), hautement toxique pour les poissons (CL50 = 280 μg ai/L), modérément toxique pour les oiseaux (DL50 = 136 mg par kg de poids corporel), et légèrement toxique pour les mammifères (DL50 = 430 mg/kg pc). Les solutions de chlorure de benzalkonium de 10 % ou plus sont toxiques pour les humains, causant l'irritation de la peau et des muqueuses. Elles peuvent provoquer la mort après ingestion6.

Le chlorure de benzalkonium est un allergène et quelques études ont jeté le doute sur sa réputation de composé sans danger. Quelques produits ont été reformulés en tenant compte de ces études mais il est toujours utilisé pour laver les yeux, dans les sprays pour laver le nez, les mains, le visage, dans les bains de bouche, les crèmes spermicides et dans d'autres produits de nettoyage, de désinfection... Certains fabricants de gouttes pour les yeux, concernés par les problèmes d'allergies lors de l'usage à long terme du benzalkonium, l'ont remplacé par de l'EDTA. D'autres ont créé des gouttes pour les yeux dans des emballages individuels à usage unique sans conservateur.

Les solutions des lentilles de contact contiennent typiquement 0,002 % à 0,01 % de chlorure de benzalkonium17. K. C. Swan18 a trouvé que l'usage répété de chlorure de benzalkonium à des concentrations de 1:5000 (0,02 %) ou supérieures peuvent dénaturer la protéine cornéenne et causer des dommages irréversibles aux yeux. Les désavantages de l'utilisation du chlorure de benzalkonium avec les lentilles de contact sont aussi discutés dans la littérature.

D'après une étude menée en 2009, le chlorure de benzalkonium induit une résistance de la bactérie Pseudomonas aeruginosa à l'antibiotique ciprofloxacine.

Fertilité

Le chlorure de benzalkonium, ou chlorure d'alkyldiméthylbenzylammonium (ADBAC), ainsi que le chlorure de didécyldiméthylammonium (DDAC) nuiraient à la reproduction22. Des souris femelles de laboratoire exposées à ces produits mettraient plus de temps à être enceintes et elles mettraient bas moins de petits. De plus, 40 % des femelles exposées à l'un ou l'autre de ces produits, seraient mortes durant leur grossesse ou lorsqu'elles mettaient bas.

Mécanisme d'action

Le chlorure de benzalkonium est un ammonium quaternaire utilisé depuis de nombreuses années en tant que surfactant et antiseptique/désinfectant. Il est connu pour ses propriétés bactéricides à des concentrations faibles (habituellement entre 0,1 et 0,2%) sur un large spectre de bactéries Gram-positives et Gram-négatives.

Le chlorure de benzalkonium élimine (diminution de 5 log) Staphylococcus aureus et les streptocoques bêta-hémolytiques (p.ex. Streptococcus pyogenes) en 1 minute, ainsi que Pseudomonas aeruginosa en 5 minutes.

Le chlorure de benzalkonium possède également une activité spermicide. Le principe actif provoque la rupture de la membrane du spermatozoïde. Sur le plan physiologique, la destruction du spermatozoïde s'effectue en deux temps : d'abord destruction du flagelle, puis éclatement de la tête. Il n'y a pas de modification de la flore saprophyte : le bacille de Döderlein est respecté.

Chlorure de benzalkonium

Additional Details: CAS: 63449-41-2.Transport: UN number : 2923; Chem class : 8; Pack group : III

Benzalkonium chlorure : pharmacodynamie 

Classe pharmacothérapeutique : Antiseptiques et Désinfectants. Ammoniums quaternaires, code ATC : D08 AJ01. Le chlorure de benzalkonium est un ammonium quaternaire utilisé depuis de nombreuses années en tant que surfactant et antiseptique/désinfectant. Il est connu pour ses propriétés bactéricides à des concentrations faibles (habituellement entre 0,1 et 0,2%) sur un large spectre de bactéries Gram-positives et Gram-négatives. Le chlorure de benzalkonium élimine (diminution de 5 log) Staphylococcus aureus et les streptocoques bêta-hémolytiques (p.ex. Streptococcus pyogenes) en 1 minute, ainsi que Pseudomonas aeruginosa en 5 minutes. Tableau. Effets bactéricides in vitro de DETTOLPRO 0,2 %, solution pour pulvérisation cutanée Souche Temps de contact Milieu Résultat Critères atteints Corynebacterium xerosis Staphylococcus epidermidis Proteus vulgaris Streptococcus pyogenes Staphylococcus aureus (MRSA) Enterococcus faecalis (VRE) 5 min Non dilué en milieu propre (0,3) et sale (3 g/l d'albumine de sérum bovin) Diminution > 5 log EN 1276 Staphylococcus aureus Corynebacterium xerosis Staphylococcus epidermidis Proteus vulgaris Streptococcus pyogenes Staphylococcus aureus (MRSA) Enterococcus faecalis (VRE) 1 min Non dilué en milieu propre (0,3) et sale (3 g/l d'albumine de sérum bovin) Diminution > 5 log EN 1276 Note : La norme EN 1276 est destinée à évaluer l'efficacité antimicrobienne de produits désinfectants conçus pour être utilisés dans les secteurs alimentaire, industriel, domestique et institutionnel. Elle peut être utilisée pour évaluer l'efficacité. Une diminution de cinq log de tous les micro-organismes en 5 minutes est exigé pour la norme EN 1276.

composés de benzalkonium;sels de benzalkonium;Composés benzalkonium;BTC-2125; BTC2125; Chlorure d'alkyl-benzyl-diméthyl-ammonium; benzalkonium; chlorure de benzalkonium; Alkyl-benzyl-diméthyl-ammonium; Alkylbenzyldiméthylammonium; Chlorure d'alkylbenzyldiméthylammonium;benzalkonium chlorure;BTC-2125; BTC2125; Chlorure d'alkyl-benzyl-diméthyl-ammonium; benzalkonium; chlorure de benzalkonium; Alkyl-benzyl-diméthyl-ammonium; Alkylbenzyldiméthylammonium; Chlorure d'alkylbenzyldiméthylammonium;BZK; BKC; BAC; ADBAC; Benzalkonium chloride; Benzalkonium (C8-C16) chloride; C8-18-Alkylbenzyldimethylammonium chloride; alkyldimethylbenzylammonium chloride

 

 

 

 

 

 

Benzalkonium chloride (BZK, BKC, BAK, BAC), also known as alkyldimethylbenzylammonium chloride (ADBAC) is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

Solubility and physical properties

Depending on purity, benzalkonium chloride ranges from colourless to a pale yellow (impure). Benzalkonium chloride is readily soluble in ethanol and acetone. Dissolution in water is slow. Aqueous solutions should be neutral to slightly alkaline. Solutions foam when shaken. Concentrated solutions have a bitter taste and a faint almond-like odour.

Standard concentrates are manufactured as 50% and 80% w/w solutions, and sold under trade names such as BAC 50, BKC 50, BC50, BC80, BAC50, BAC80, etc. The 50% solution is purely aqueous, while more concentrated solutions require incorporation of rheology modifiers (alcohols, polyethylene glycols, etc.) to prevent increases in viscosity or gel formation under low temperature conditions.

Cationic surfactant

Benzalkonium chloride also possesses surfactant properties, dissolving the lipid phase of the tear film and increasing drug penetration, making it a useful excipient, but at the risk of causing damage to the surface of the eye.

Laundry detergents and treatments

Softeners for textiles

Phase transfer agent

Main article: Phase transfer catalysis

Benzalkonium chloride is a mainstay of phase-transfer catalysis, an important technology in the synthesis of organic compounds, including drugs.

Bioactive agents

Especially for its antimicrobial activity, benzalkonium chloride is an active ingredient in many consumer products:

Pharmaceutical products such as eye, ear and nasal drops or sprays, as a preservative

Personal care products such as hand sanitizers, wet wipes, shampoos, soaps, deodorants and cosmetics

Skin antiseptics and wound wash sprays, such as Bactine.

Throat lozenges and mouthwashes, as a biocide

Spermicidal creams

Cleaners for floor and hard surfaces as a disinfectant, such as Lysol and Dettol antibacterial spray and wipes.

Algaecides for clearing of algae, moss, lichens from paths, roof tiles, swimming pools, masonry, etc.

Benzalkonium chloride is also used in many non-consumer processes and products, including as an active ingredient in surgical disinfection. A comprehensive list of uses includes industrial applications. An advantage of benzalkonium chloride, not shared by ethanol-based antiseptics or hydrogen peroxide antiseptic, is that it does not cause a burning sensation when applied to broken skin.[citation needed] However, prolonged or repeated skin contact may cause dermatitis.

During the course of the COVID-19 pandemic, from time to time there have been shortages of hand cleaner containing ethanol or isopropanol as active ingredients. The FDA has stated that benzalkonium chloride is eligible as an alternative for use in the formulation of healthcare personnel hand rubs. However, in reference to the FDA rule, the CDC states that it does not have a recommended alternative to ethanol or isopropanol as active ingredients, and adds that "available evidence indicates benzalkonium chloride has less reliable activity against certain bacteria and viruses than either of the alcohols.

Medicine

Benzalkonium chloride is a frequently used preservative in eye drops; typical concentrations range from 0.004% to 0.01%. Stronger concentrations can be caustic and cause irreversible damage to the corneal endothelium.

Avoiding the use of benzalkonium chloride solutions while contact lenses are in place is discussed in the literature.

In Russia and China, benzalkonium chloride is used as a contraceptive. Tablets are inserted vaginally, or a gel is applied, resulting in local spermicidal contraception. It is not a failsafe method, and can cause irritation.

Beekeeping

It is used in beekeeping for the treatment of rotten diseases of the brood.

Adverse effects

Although historically benzalkonium chloride has been ubiquitous as a preservative in ophthalmic preparations, its ocular toxicity and irritant properties,in conjunction with consumer demand, have led pharmaceutical companies to increase production of preservative-free preparations, or to replace benzalkonium chloride with preservatives which are less harmful.

Many mass-marketed inhaler and nasal spray formulations contain benzalkonium chloride as a preservative, despite substantial evidence that it can adversely affect ciliary motion, mucociliary clearance, nasal mucosal histology, human neutrophil function, and leukocyte response to local inflammation. Although some studies have found no correlation between use of benzalkonium chloride in concentrations at or below 0.1% in nasal sprays and drug-induced rhinitis,[20] s have recommended that benzalkonium chloride in nasal sprays be avoided.[21][22] In the United States, nasal steroid preparations that are free of benzalkonium chloride include budesonide, triamcinolone acetonide, dexamethasone, and Beconase and Vancenase aerosol inhalers.

Benzalkonium chloride is irritant to middle ear tissues at typically used concentrations. Inner ear toxicity has been demonstrated.

Occupational exposure to benzalkonium chloride has been linked to the development of asthma.In 2011, a large clinical trial designed to evaluate the efficacy of hand sanitizers based on different active ingredients in preventing virus transmission amongst schoolchildren was re-designed to exclude sanitizers based on benzalkonium chloride due to safety concerns.

Benzalkonium chloride has been in common use as a pharmaceutical preservative and antimicrobial since the 1940s. While early studies confirmed the corrosive and irritant properties of benzalkonium chloride, investigations into the adverse effects of, and disease states linked to, benzalkonium chloride have only surfaced during the past 30 years

Benzalkonium chloride is a human skin and severe eye irritant. It is a suspected respiratory toxicant, immunotoxicant, gastrointestinal toxicant, and neurotoxicant.

Benzalkonium chloride formulations for consumer use are dilute solutions. Concentrated solutions are toxic to humans, causing corrosion/irritation to the skin and mucosa, and death if taken internally in sufficient volumes. 0.1% is the maximum concentration of benzalkonium chloride that does not produce primary irritation on intact skin or act as a sensitizer.

Poisoning by benzalkonium chloride is recognised in the literature. A 2014 case study detailing the fatal ingestion of up to 8.1 oz (240ml) of 10% benzalkonium chloride in a 78-year-old male also includes a summary of the currently published case reports of benzalkonium chloride ingestion. While the majority of cases were caused by confusion about the contents of containers, one case cites incorrect pharmacy dilution of benzalkonium chloride as the cause of poisoning of two infants.[33] In 2018 a Japanese nurse was arrested and admitted to having poisoned approximately 20 patients at a hospital in Yokohama by injecting benzalkonium chloride into their intravenous drip bags.

Benzalkonium chloride poisoning of domestic pets has been recognised as a result of direct contact with surfaces cleaned with disinfectants using benzalkonium chloride as an active ingredient.

Biological activity

The greatest biocidal activity is associated with the C12 dodecyl and C14 myristyl alkyl derivatives. The mechanism of bactericidal/microbicidal action is thought to be due to disruption of intermolecular interactions. This can cause dissociation of cellular membrane lipid bilayers, which compromises cellular permeability controls and induces leakage of cellular contents.  biomolecular complexes within the bacterial cell can also undergo dissociation. Enzymes, which finely control a wide range of respiratory and metabolic cellular activities, are particularly susceptible to deactivation. Critical intermolecular interactions and tertiary structures in such highly specific biochemical systems can be readily disrupted by cationic surfactants.

Benzalkonium chloride solutions are fast-acting biocidal agents with a moderately long duration of action. They are active against bacteria and some viruses, fungi, and protozoa. Bacterial spores are considered to be resistant. Solutions are bacteriostatic or bactericidal according to their concentration. Gram-positive bacteria are generally more susceptible than gram-negative bacteria. Its activity depends on the surfactant concentration and also on the bacterial concentration (inoculum) at the moment of the treatment.Activity is not greatly affected by pH, but increases substantially at higher temperatures and prolonged exposure times.

In a 1998 study using the FDA protocol, a non-alcohol sanitizer with benzalkonium chloride as the active ingredient met the FDA performance standards, while Purell, a popular alcohol-based sanitizer, did not. The study, which was undertaken and reported by a leading US developer, manufacturer and marketer of topical antimicrobial pharmaceuticals based on quaternary ammonium compounds, found that their own benzalkonium chloride-based sanitizer performed better than alcohol-based hand sanitizer after repeated use.

Advancements in the quality and efficacy of benzalkonium chloride in current non-alcohol hand sanitizers has addressed the CDC concerns regarding gram negative bacteria, with the leading products being equal if not more effective against gram negative, particularly New Delhi metallo-beta-lactamase 1 and  antibiotic resistant bacteria.

Newer formulations using benzalkonium blended with various quaternary ammonium derivatives can be used to extend the biocidal spectrum and enhance the efficacy of benzalkonium based disinfection products.[citation needed] Formulation techniques have been used to great effect in enhancing the virucidal activity of quaternary ammonium-based disinfectants such as Virucide 100 to typical healthcare infection hazards such as hepatitis and HIV. The use of appropriate excipients can also greatly enhance the spectrum, performance and detergency, and prevent deactivation under use conditions. Formulation can also help minimise deactivation of benzalkonium solutions in the presence of organic and inorganic contamination.

Degradation

Biodegradation pathways of BAC with Fenton process (H2O2/Fe2+)

Benzalkonium chloride degradation follows consecutive debenzylation, dealkylation, and demethylation steps producing benzyl chloride, alkyl dimethyl amine, dimethyl amine, long chain alkane, and ammonia. The intermediates, major, and minor products can then be broken down into CO2, H2O, NH3, and Cl–. The first step to the biodegradation of BAC is the fission or splitting of the alkyl chain from the quaternary nitrogen as shown in the diagram. This is done by abstracting the hydrogen from the alkyl chain by using a hydroxyl radical leading to a carbon centered radical. This results in benzyl dimethyl amine as the first intermediate and dodecanal as the major product.

From here, benzyl dimethyl amine can be oxidized to benzoic acid using the Fenton process. The trimethyl amine group in dimethylbenzylamine can be cleaved to form a benzyl that can be further oxidized to benzoic acid. Benzoic acid uses hydroxylation (adding a hydroxyl group) to form p-hydroxybenzoic acid. Benzyldimethylamine can then be converted into ammonia by performing demethylation twice, which removes both methyl groups, followed by debenzylation, removing the benzyl group using hydrogenation. The diagram represents suggested pathways of the biodegradation of BAC for both the hydrophobic and the hydrophilic regions of the surfactant. Since stearalkonium chloride is a type of BAC, the biodegradation process should happen in the same manner.

Regulation

Benzalkonium chloride is classed as a Category III antiseptic active ingredient by the United States Food and Drug Administration (FDA). Ingredients are categorized as Category III when "available data are insufficient to classify as safe and effective, and further testing is required”. Benzalkonium chloride was deferred from further rulemaking in the 2019 FDA Final Rule on safety and effectiveness of consumer hand sanitizers, "to allow for the ongoing study and submission of additional safety and effectiveness data necessary to make a determination" on whether it met these criteria for use in OTC hand sanitizers, but the agency indicated it did not intend to take action to remove benzalkonium chloride-based hand sanitizers from the market. There is acknowledgement that more data are required on its safety, efficacy, and effectiveness, especially with relation to:

Human pharmacokinetic studies, including information on its metabolites

Studies on animal absorption, distribution, metabolism, and excretion

Data to help define the effect of formulation on dermal absorption

Studies on developmental and reproductive toxicology

Potential hormonal effects

Assessment of the potential for development of bacterial resistance

Risks of using it as a contraceptive method

In September 2016, the FDA announced a ban on nineteen ingredients in consumer antibacterial soaps citing a lack of evidence for safety and effectiveness. A ban on three additional ingredients, including benzalkonium chloride, was deferred to allow ongoing studies to be completed.

Benzalkonium chloride

Cosmetic Products Regulation, Annex V - Allowed Preservatives

Quaternary ammonium compounds, alkylbenzyldimethyl, chlorides

Pre-Registration process, 

IUPAC names

Alkyldimethylbenzylammonium chloride

ammonium, alkylbenzyldimethyl-,chloride

Benzalkonium Chlorid

Benzalkonium Chloride (4% aqueous solution)

Benzalkonium chloride, alkyl distribution C8-C16

Benzalkónium-klorid

benzyl-dimethyl-tetradecylazanium chloride

benzyl-dodecyl-dimethylazanium chloride

N-alkyl(C8-C16)dimethylbenzylammonium chloride

names

Benzalkonium Chloride C16

Pre-Registration process

identifiers

12741-06-9

CAS number

39434-18-9

CAS number

59890-14-1

CAS number

75635-12-0

CAS number

8001-54-5

CAS number

8011-91-4

CAS number

8036-90-6

CAS number

8039-63-2

CAS number

8045-21-4

CAS number

Quaternary ammonium compounds, benzyl-C12-14-alkyldimethyl, chlorides

IUPAC names

Benzalkonium Chloride

Benzyl-C12-14-alkyldimethylammonium chlorides

 

C12-14 ADBAC

Quaternary ammonium compounds, benzyl-C12-14 (even-numbered)-alkyldimethyl, chlorides

Quaternary ammonium compounds, benzyl-C12-C14 (even-numbered)-alkyldimethyl, chlorides

ROQUAT BL 50

Trade names

BAC70

PR-1107A

PR-4951

PR-9010

 identifiers

1097616-29-9

Deleted CAS number

79177-05-2

Deleted CAS number

85409-22-9

CAS number

(C12-C18) Alkyldimethylbenzyl ammonium chloride

This substance is identified by SDA Substance Name: C12-C18 alkyl benzyl dimethyl ammonium chloride and SDA Reporting Number: 16-052-00.

(C12-C18)Alkylbenzyldimethylammonium chloride

This substance is identified by SDA Substance Name: C12-C18 alkyl benzyl dimethyl ammonium chloride and SDA Reporting Number: 16-052-00.

Alkyl(C12-C18)benzyldimethylammonium chloride

This substance is identified by SDA Substance Name: C12-C18 alkyl benzyl dimethyl ammonium chloride and SDA Reporting Number: 16-052-00.

C12-18-Alkyldimethylbenzyl ammonium chlorides

This substance is identified by SDA Substance Name: C12-C18 alkyl benzyl dimethyl ammonium chloride and SDA Reporting Number: 16-052-00.

N-Alkyl dimethyl benzyl ammonium chloride (C12-C18)

This substance is identified by SDA Substance Name: C12-C18 alkyl benzyl dimethyl ammonium chloride and SDA Reporting Number: 16-052-00.

, Cosmetic Products Regulation, Annex III - Restricted Substances, Cosmetic Products Regulation, Annex V - Allowed Preservatives

Quaternary ammonium compounds, benzyl-C12-18-alkyldimethyl, chlorides

EC Inventory, Pre-Registration process, SDA 16-052-00

This substance is identified by SDA Substance Name: C12-C18 alkyl benzyl dimethyl ammonium chloride and SDA Reporting Number: 16-052-00.

Translated names

Alkil (C12-18) chlorku dimetylobenzyloamonu (ADBAC (C12-18)) (pl)

Alkil (C12-18) dimetilbenzil amonijev klorid (ADBAC (C12-18) (hr)

Alkil (C12-18) dimetilbenzil amonio chloridas (ADBAC (C12-18)) (lt)

Alkil (C12-18) dimetilbenzilamonija hlorīds (ADBAC (C12-18)) (lv)

Alkil (C12–16) dimetil-benzil-ammónium-klorid (ADBAC [C12–18]) (hu)

Alkil (C12–18) dimetilbenzil amonijev klorid (ADBAC (C12–18)) (sl)

Alkyl (C12-18) dimethylbenzyl ammonium chloride (ADBAC (C12-18)) (mt)

alkyl(C12-18)benzyldimetylamónium-chlorid [ADBAC (C12-18)] (sk)

alkyl(C12-18)dimethylbenzylammoniumchlorid (ADBAC (C12-18)) (cs)

Alkyl(C12-18)dimethylbenzylammoniumchloride (ADBAC (C12-18)) (nl)

Alkyl(C12-18)dimetylbensylammoniumklorid (ADBAC (C12-18)) (sv)

Alkyyli-(C12-18)-dimetyylibentsyyliammoniumkloridi (ADBAC(C12-18)) (fi)

C12–18-alküüldimetüülbensüülammooniumkloriid (ADBAC (C12–18)) (et)

Chlorure d'alkyl(C12-C18)diméthylbenzylammonium [ADBAC (C12-18)] (fr)

Cloreto de alquil(C12-18)dimetilbenzilamónio (ADBAC C12-18) (pt)

Cloruro de C12-18-alquildimetilbencilamonio (ADBAC (C12-18)) (es)

Clorură de alchil (C12-18) dimetilbenzil amoniu [ADBAC (C12-18)] (ro)

Composti di ammonio quaternario, benzil- C12-18 -alchildimetil, cloruri (ADBAC (C12-18) (it)

Χλωριούχο αλκυλο(C12-18)διμεθυλοβενζυλαμμώνιο (ADBAC (C12-18)) (el)

Алкил(C12-18)диметилбензиламониев хлорид (ADBAC (C12-18)) (bg)

IUPAC names

ALKYL DIMETHYL BENZYL AMMONIUM CHLORIDE

Alkyldimethylbenzyl ammonium chloride

Benzalkonium Chloride

benzyl-dimethyl-tetradecylazanium chloride

C12-C18 alkyl benzyl dimethyl ammonium chloride

N-benzyl-N,N-dimethyl-C12-18-(evennumbered)-alkyl-1-aminium chloride

N-benzyl-N,N-dimethyltetradecan-1-aminium chloride

identifiers

56939-83-4

CAS number

68391-01-5

CAS number

68424-86-2

CAS number

959428-18-3

Alkylbenzyldimethylammonium chlorides with alkyl chain lengths of C8, C10, C12, C14, C16 and C18

Benzalkonium chlorideC8-18-Alkydimethylbenzyl ammonium chlorides

Cosmetic Products Regulation, Annex III - Restricted Substances, Cosmetic Products Regulation, Annex V - Allowed Preservatives

Quaternary ammonium compounds, benzyl-C8-18-alkyldimethyl, chlorides

EC Inventory, , Pre-Registration process, CAD - Chemical Agents Directive, Art. 2(b)(i) - Hazardous Agents, EU Ecolabels - Restrictions for Hazardous Substances/Mixtures, Workplace Signs - minimum requirements & signs on containers and pipes, Waste Framework Directive, Annex III - Waste - Hazardous Properties, Fertiliser Regulation- Annex I, E.3 (chelating and complexing agents)

Translated names

(C8-18)alkylbenzyldimetylammoniumklorid (no)

(C8-18)alkyylibentsyylidimetyyliammoniumkloridi (fi)

chlorki czwartorzedowych zwiazków amoniowych - chlorki benzylo(C8-18)alkilodimetyloamonium (pl)

composti di ammonio quaternario, benzil-C8-18-alchildimetil, cloruri (it)

compostos de amónio quaternário, benzil-C8-18-alquildimetil, cloretos (pt)

composés d'ammonium quaternaire, benzyl-C8-18-alkyldiméthyle, chlorures (fr)

compuestos de amonio cuaternario, bencil-C8-18-alquildimetil, cloruros (es)

compusi de amoniu cuaternari, benzil-C8-18-alildimetil, cloruri (ro)

ketvirtiniai amonio junginiai, benzil-C8-18-alkildimetil-, chloridai (lt)

kvarterne amonijeve spojine, benzil-C8-18-alkildimetil kloridi (sl)

kvarterni amonijevi spojevi,benzil-C8-18-alkildimetil, kloridi (hr)

kvarterní amoniové sloučeniny, alkyl(C8-C18)(benzyl) dimethylamonium-chlorid (cs)

kvartérne amóniové zlúčeniny, (C8-18-alkyl)(benzyl)di(metyl)amónium-chloridy (sk)

Kvaternaarsete bensüül-C 8-18-alküüldimetüülammooniumiühendite kloriidid (et)

kvaterner ammónium vegyületek, benzil-C8-18-alkildimetilammónium-klorid (hu)

kvaternääriset ammoniumyhdisteet, bentsyyli-C8-18-alkyylidimetyylikloridit (fi)

kvaternære ammoniumforbindelser, benzyl-C8-18-alkyldimethyl-, chlorider (da)

kvaternære ammoniumforbindelser, benzyl-C8-18-alkyldimetyl, klorider (no)

quaternaire ammoniumverbindingen, benzyl-C8-18-alkyldimethyl, chloriden (nl)

Quaternäre Ammoniumverbindungen, Benzyl-C8-18-alkyldimethyl-, Chloride (de)

četraizvietotie amonija savienojumi, benzil-C8-C18-alkildimetil-hlorīdi (lv)

χλωρίδια των βενζυλο-C8-18-αλκυλοδιμεθυλο τεταρτοταγών ενώσεων αμμωνίου (el)

кватернерни амониеви съединения, бензил-C8-18-aлкилдиметил, хлориди (bg)

CAS names

Alkylbenzyldimethylammonium chlorides, benzyl-C8-18-alkyldimethyl

IUPAC names

Alkyldimethylbenzyl ammonium chloride

Benzyl(dodecyl)dimethylammonium chloride, benzyl(tetradecyldimethylammonium chloride

benzyl-C8-18-alkyldimethyl chloride

benzyl-decyl-dimethylazanium chloride

benzyl-decyl-dimethylazanium;chloride

benzyl-dimethyl-tridecyl-azanium chloride

N-benzyl-N,N-dimethyldecan-1-aminium chloride

Quaternary ammonium compounds, benzylcoco alkyldimethyl, chlorides

 identifiers

50957-62-5

CAS number

51004-71-8

CAS number

51668-62-3

CAS number

612-140-00-5

Index Number

63449-41-2

CAS number

69344-71-4

Alkyl (C12-16) dimethylbenzyl ammonium chloride (ADBAC/BKC (C12-16))

Quaternary ammonium compounds, benzyl-C12-16-alkyldimethyl, chlorides

Translated names

Alkil (C12-16) dimetilbenzil amonijev klorid (ADBAC/BKC (C12-16)) (hr)

Alkil (C12-16) dimetilbenzil amonio chloridas (ADBAC (C12-16)) (lt)

Alkil (C12-16) dimetilbenzilamonija hlorīds (ADBAC/BKC (C12-16)) (lv)

Alkil (C12-16)-chlorku dimetylobenzyloamonu (ADBAC/BKC (C12-16)) (pl)

Alkil (C12–16) dimetil-benzil-ammónium-klorid (ADBAC/BKC [C12–16]) (hu)

Alkil (C12–16) dimetilbenzil amonijev klorid (ADBAC/BKC (C12–16)) (sl)

Alkyl (C12-16) dimethylbenzyl ammonium chloride (ADBAC/BKC (C12-C16)) (mt)

alkyl(C12-16)benzyldimetylamónium-chlorid [ADBAC/BKC (C12-C16)] (sk)

alkyl(C12-16)dimethylbenzylammoniumchlorid (ADBAC/BKC (C12-16)) (da)

alkyl(C12-16)dimethylbenzylammoniumchlorid (ADBAC/BKC (C12-C16)) (cs)

Alkyl(C12-16)dimethylbenzylammoniumchloride (ADBAC/BKC (C12-16)) (nl)

Alkyl(C12-16)dimetylbensylammoniumklorid (ADBAC/BKC (C12-C16)) (sv)

Alkyyli-(C12-16)-dimetyylibentsyyliammoniumkloridi (ADBAC/BKC (C12-16)) (fi)

C12–16-alküüldimetüülbensüülammooniumkloriid (ADBAC/BKC (C12–16)) (et)

Chlorure d'alkyl(C12-C16)diméthylbenzylammonium [ADBAC/BKC (C12-C16)] (fr)

Cloreto de alquil(C12-16)dimetilbenzilamónio (ADBAC/KBC C12-16) (pt)

Cloruro de C12-16-alquildimetilbencilamonio (ADBAC/BKC (C12-16)) (es)

Cloruro di alchil (C12-16) dimetilbenzilammonio (ADBAC/BKC (C12-C16)) (it)

Clorură de alchil (C12-16) dimetilbenzil amoniu [ADBAC/BKC (C12-C16)] (ro)

Χλωριούχο αλκυλο(C12-16)διμεθυλοβενζυλαμμώνιο (ADBAC/BKC (C12-C16)) (el)

Алкил(C12-16)диметилбензиламониев хлорид (ADBAC/BKC (C12-C16)) (bg)

IUPAC names

Alkyl dimethyl benzyl ammonium chloride

benzyl-C12-16-alkyldimethyl, chlorides

Benzyl-dimethyl-tetradecyl azanium chloride

benzyl-dimethyl-tetradecylazanium chloride

dimethyl benzyl ammonium chloride

N-ALKYL(C12-16)-N,N-DIMETHYL-N-BENZYLAMMONIUM CHLORIDE

N-Alkyl-N,N-dimethyl-N-benzylammonium Chloride

N-benzyl-N,N-dimethyl-C12-16-(evennumbered)-alkyl-1-aminium chloride

N-Benzyl-N,N-dimethyltetradecan-1-aminium chloride

Not applicable - this material is an on-site isolated intermediate and is not made available commercially.

Quaternary ammoniumcompounds, benzyl-C12-16-alkyldimethyl, chlorides

 identifiers

284043-23-8

CAS number

39403-41-3

CAS number

63449-42-3

CAS number

68424-85-1

CAS number

70294-44-9