122-19-0

Basic information

• Product Name: Stearyldimethylbenzylammonium chloride
• Synonyms: SKC;STEARALKONIUM CHLORIDE;STEARYLDIMETHYLBENZYL AMMONIUM CHLORIDE;OCTADECYLDIMETHYL BENZYL AMMONIUM CHLORIDE;2b;2b(oniumcompound);alkyl*dimethylbenzylammoniumchloride*(100%c18);alkyldimethylbenzylammoniumchloride(100%c18)
• CAS NO: 122-19-0
• Molecular Formula: C₂₇H₅₀N*Cl
• Molecular Weight: 424.15
• EINECS: 204-527-9
• Product Categories: Hair Care;Home Care;Ammonium Chlorides (Quaternary);Aromatic Quaternary Ammonium Salts (Surfactants);Cationic Surfactants;Functional Materials;Quaternary Ammonium Compounds;Surfactants;Aromatics;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;API Intermediate
• Mol File: 122-19-0.mol

Chemical Properties

• Melting Point: 54-56°C
• Boiling Point: 100oC
• Flash Point: 94oC
• Appearance: White solid or thick liquid with a mild odor
• Density: 0.98
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility: 4000 G/L (20 ºC)
• CAS DataBase Reference: Stearyldimethylbenzylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Stearyldimethylbenzylammonium chloride(122-19-0)
• EPA Substance Registry System: Stearyldimethylbenzylammonium chloride(122-19-0)

Safety Data

• Hazard Codes: C,N
• Statements: 22-38-41-50-34-21/22
• Safety Statements: 26-36/37/39-61-45
• RTECS: BO7000000
• Hazardous Substances Data: 122-19-0(Hazardous Substances Data)

Usage

Chemical Properties

Benzyldimethylstearylammonium Chloride is a light yellow sticky paste. It is soluble in water, acid resistant, hard water resistant, inorganic salt resistant, not alkali resistant.

Uses

Different sources of media describe the Uses of 122-19-0 differently. You can refer to the following data:
1. Stearyldimethylbenzylammonium chloride is a compound used in products for promoting skin cleanliness and health. It is used in hair care formulations, as a hair conditioner and cream rinse.
2. Stearyldimethylbenzylammonium chloride is an anti-static that can also be used as a surfactant and/or a preservative depending on formulatory requirements.

Preparation

Synthesis of benzyldimethylstearylammonium chloride: put 450kg of dimethyl octadecylamine into the reaction kettle, heat to 80~85℃, and slowly add 180kg of benzyl chloride under stirring in 1.5~2h. Keep warm at 80～90℃ during the drop addition. After the dosing is completed, increase the temperature to 100~105℃, hold the reaction for several hours and take samples to measure the pH value. When the pH value of 1% aqueous solution reaches 6~6.5, the reaction is completed. Cool down to 60℃ and discharge to get benzyldimethylstearylammonium chloride.

General Description

Stearyldimethylbenzylammonium chloride is White solid or thick liquid with a mild odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Acidic organic salt solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases.

Health Hazard

Ingestion causes gastrointestinal disturbances. Contact with chemical irritates eyes and skin and may damage eyes.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen and hydrochloric acid fumes may form in fires.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A human skin irritant and severe experimental eye irritant. When heated to decomposition it emits very toxic fumes of NOx, NH3, and Cl-.

Purification Methods

Crystallise the salt from acetone, EtOAc or EtOAc/ Et2O. [Sumiki et al. J Agric Chem Soc Jpn 26 325 1952, Chem Abstr 3505 1953, Beilstein 12 III 2212, 12 IV 2168.]

InChI:InChI=1/C27H50N/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22-25-28(2,3)26-27-23-20-19-21-24-27/h19-21,23-24H,4-18,22,25-26H2,1-3H3/q+1

Synthetic route

N,N-dimethyl-n-octadecylamine (124-28-7) + benzyl chloride (100-44-7) → benzalkonium chloride (122-19-0)

1-octadecanol (112-92-5) + alkali alkylate → benzalkonium chloride (122-19-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc chloride, hydrogen chloride / 140 °C 2: H2O / 140 - 150 °C 3: H2O / 60 - 65 °C View Scheme

1-chlorooctadecane (3386-33-2) → benzalkonium chloride (122-19-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 140 - 150 °C 2: H2O / 60 - 65 °C View Scheme

benzalkonium chloride (122-19-0) → N,N-Dimethyl-N-sulfobenzyl-N-octadecylammonium (65180-43-0)

Conditions	Yield
With chlorosulfonic acid at 50 - 60℃; under 1500.15 Torr; Temperature; Large scale;	99.74%

benzalkonium chloride (122-19-0) + rac-Potassium mandelate (84864-61-9) → benzyldimethyloctadecylammonium mandelate

Conditions	Yield
In water at 60℃; for 6h;	98%

C34H64O11 + benzalkonium chloride (122-19-0) → C27H50N(1+)*C34H63O11(1-)

Conditions	Yield
With potassium hydroxide In water pH=7;

Dicyanoargentat(I) (1-) (768296-31-7) + benzalkonium chloride (122-19-0) → N,N-dimethyl N-benzyl N-octadecyl ammonium dicyano argentate (I)

Conditions	Yield
In water slow addition of a solution of a dicyano argentate in H2O under stirring to an equimolar solution of the ammonium chloride in H2O;; precipitation, washing with H2O and crystallization within 2 days on storing; drying in vacuum;;

Upstream product

• 124-28-7 N,N-dimethyl-n-octadecylamine 
• 100-44-7 benzyl chloride 
• 3386-33-2 1-chlorooctadecane 
• 112-92-5 1-octadecanol 

Downstream Products

• 65180-43-0 N,N-Dimethyl-N-sulfobenzyl-N-octadecylammonium 

Relevant articles and documents

Synthetic method of aryl sulphobetaine in solvent-free system

The invention relates to a synthetic method of aryl sulphobetaine in a solvent-free system. The method comprises the steps that alkyl dimethyl tertiary amine and benzyl chloride which are close to the stoichiometric ratio react to synthetize alkyl dimethyl benzyl ammonium chloride at a low temperature, under high-speed stirring of a planetary stirrer and dilution of dry air in the solvent-free system, alkyl dimethyl benzyl ammonium chloride is added into chlorosulfonic acid close to the stoichiometric ratio step by step for a reaction, and alkyl dimethyl benzyl sulphobetaine is obtained. According to the method, no solvent is needed, the production cost is low, a small amount of residual chlorosulfonic acid obtained after a solvent-free reaction can be recycled through high-speed centrifugation, and the yield of alkyl dimethyl benzyl sulphobetaine can reach 98% or above.

ACTIVE DELIVERY SYSTEMS FORMULATIONS

The present invention relates to active delivery system formulations, and methods of making and using the same. Said formulations, when applied to a substrate surface, form a protective coating on the surface and permit constituent active agents to act on the surface and in the surrounding medium.

DENTAL ORAL COMPOSITION

A dental composition for oral use, containing a phosphorylated saccharide (a), a polyphosphoric acid and/or a salt thereof (b), and a cationic bactericidal agent (c), wherein a ratio of a total amount of the phosphorylated saccharide (a) and the polyphosphoric acid and/or a salt thereof (b) contained to an amount of the cationic bactericidal agent (c) contained, i.e. {(a)+(b)}/(c), is from 0.05 to 20 in a weight ratio. The dental composition for oral use of the present invention can be suitably used for an oral cavity cleaning agent, including dentifrice agents such as a paste dentifrice agent, a powder dentifrice agent, and a liquid dentifrice agent, a mouse-wash agent, a troche, a tablet, a cream, an ointment, a bonding agent, a mouth spray, a coating agent to tooth surface or a dental prosthetic, a hypersensitive inhibitor, a therapeutic agent for periodontal diseases, that is applied to a periodontal pocket, wet tissue for oral cavity care, an oral refreshing agent, chewing gum, or a gargling agent, or the like.

Interactions between biocide cationic agents and bacterial biofilms

The resistance of bacterial biofilms to physical and chemical agents is attributed in the literature to various interconnected processes. The limitation of mass transfer alters the growth rate, and physiological changes in the bacteria in the film also appear. The present work describes an approach to determination of the mechanisms involved in the resistance of bacteria to quaternary ammonium compounds (benzalkonium chloride) according to the C-chain lengths of those compounds. For Pseudomonas aeruginosa CIP A 22, the level of resistance of the bacteria in the biofilm relative to that of planktonic bacteria increased with the C-chain length. For cells within the biofilm, the exopolysaccharide induced a characteristic increase in surface hydrophilicity. However, this hydrophilicity was eliminated by simple resuspension and washing. The sensitivity to quaternary ammonium compounds was restored to over 90%. Staphylococcus aureus CIP 53 154 had a very high level of resistance when it was in the biofilm form. A characteristic of bacteria from the biofilm was a reduction in the percent hydrophobicity, but the essential point is that this hydrophobicity was retained after the biofilm bacteria were resuspended and washed. The recovery of sensitivity was thus only partial. These results indicate that the factors involved in biofilm resistance to quaternary ammonium compounds vary according to the bacterial modifications induced by the formation of a biofilm. In the case of P. aeruginosa, we have underlined the involvement of the exopolysaccharide and particularly the three-dimensional structure (water channels). In the case of S. aureus, the role of the three-dimensional structure is limited and drastic physiological changes in the biofilm cells are more highly implicated in resistance.

Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth

The present invention discloses compositions containing lecithin and/or bactericidal compounds, and hydrophobic materials which form, upon application to dental surfaces, adhesive, protective and bacteria-inhibiting barriers.

Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth

The present invention discloses compositions containing a transfer agent and/or bactericidal compounds, and hydrophobic materials which form, upon application to dental surfaces, adhesive, protective and bacteria-inhibiting barriers.

Dentifrice containing a poly(hydroxypropyl ether) non-ionic surfactant and a specified cationic polymer

Dentifrice containing, in combination, (A) a poly(hydroxypropyl ether) nonionic surfactant, and (B) a cationic polymer selected from the group consisting of (i) a vinylpyrrolidone/dialkylaminoalkyl or -hydroxyalkyl acrylate or methacrylate, quaternized or nonquaternized and (ii) a cationic polysaccharide. This dentifrice is characterized by good foamability, pleasant taste and it does not attack the buccal mucosae and the gums.

Hair rinse composition

A hair rinse composition having improved rinsing performance and a process specified to prepare the same. The composition according to the invention comprises (A) 0.05 to 0.5 wt % of cationic surface active agent, and (B) a higher alcohol or a glycerine mono fatty acid ester having a melting point not lower than 45° C. The ingredient (B) should be contained in an amount of 3 to 15 times by weight to ingredient (A). The composition is prepared by diluting a highly concentrated emulsified product containing 0.4 to 34 wt % of ingredient (A) and (B) in total with 1 to 20 times by weight to the emulsified product of water.