683-10-3

Basic information

• Product Name: Lauryl betaine
• Synonyms: (dodecyldimethylammonio)acetate;1-dodecanaminium,n-(carboxymethyl)-n,n-dimethyl-,hydroxide,innersalt;1-dodecanaminium,n-(carboxymethyl)-n,n-dimethyl-,hyroxide,innersalt;1-Dodecanaminium,N-(carboxymethyl)-N,N-dimethyl-,innersalt;ambitericd40;amipol6s;ammonium,(carboxymethyl)dodecyldimethyl-,hydroxide,innersalt;amphitol20bs
• CAS NO: 683-10-3
• Molecular Formula: C₁₆H₃₃NO₂
• Molecular Weight: 271.44
• EINECS: 266-368-1
• Product Categories: Hair Care;Home Care;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 683-10-3.mol

Chemical Properties

• Boiling Point: 414.52°C (rough estimate)
• Appearance: Light yellow clear liquid
• Density: 1.04 g/mL at 20 °C
• Vapor Pressure: 16.796hPa at 21.1℃
• Refractive Index: 1.4545 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 464g/L at 25℃
• BRN: 3670807
• CAS DataBase Reference: Lauryl betaine(CAS DataBase Reference)
• NIST Chemistry Reference: Lauryl betaine(683-10-3)
• EPA Substance Registry System: Lauryl betaine(683-10-3)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25-21
• Safety Statements: 26-36-45-36/37
• RIDADR: 2811
• WGK Germany: 1
• RTECS: JR2115000
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 683-10-3(Hazardous Substances Data)

Usage

Uses

Used in Personal Care Industry:
Lauryl betaine is used as a skin-conditioning agent for its ability to act as an anti-static conditioning agent and a foam booster, enhancing the performance of hair care products.
Used in Shampoos and Personal Hygiene Products:
Lauryl betaine is used as a surfactant for its cleansing and foaming properties, making it an essential component in the formulation of shampoos and personal hygiene products.
Used in Oil Field Chemicals:
Lauryl betaine is used in the oil field industry, where its surfactant properties contribute to the efficiency of various processes, such as enhanced oil recovery and drilling operations.

InChI:InChI=1/C19H39NO2/c1-7-8-9-10-11-12-13-14-15-16-19(2,3)17(18(21)22)20(4,5)6/h17H,7-16H2,1-6H3

Synthetic route

1-dodecyl alcohol (112-53-8) + N,N-dimethylglycine methyl ester (7148-06-3) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
With Novovzym 435 In n-heptane at 65℃; for 5h; Dean-Stark; Green chemistry;	99%

N,N-dimethylaminododecane (112-18-5) + potassium chloroacetate (7748-25-6) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
In acetonitrile at 80℃; for 2h;	96%

dodecyl(2-ethoxy-2-oxoethyl)dimethylazanium p-toluenesulfonate → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
With toluene-4-sulfonic acid In water at 45 - 55℃; for 24h; Time;	90.5%

N,N-dimethylaminododecane (112-18-5) + sodium monochloroacetic acid (3926-62-3) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
In water at 90 - 95℃; for 1h;	35%
With water
With ethanol at 100℃;

N,N-dimethylaminododecane (112-18-5) + chloroacetic acid ethyl ester (105-39-5) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
Erwaermen des Reaktionsprodukts mit aethanol.KOH;

methyl N-dodecyl-N,N-dimethylglycinate chloride (17283-72-6) → methanol (67-56-1) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
With sodium hydroxide; lithium chloride In water at 25℃; Rate constant; other salts, MTACl or CTACl wer used;

methyl N-dodecyl-N,N-dimethylglycinate (77814-51-8) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
With sodium hydroxide; cetyltrimethylammonium hydroxide at 25℃; Rate constant; other cationic micelles or without NaOH;

Dodecyl-dimethyl-[(4-nitro-phenylcarbamoyl)-methyl]-ammonium; bromide → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With water; palmitate ion at 30℃; Rate constant; other catalysts;

Dodecyl-dimethyl-{[methyl-(4-nitro-phenyl)-carbamoyl]-methyl}-ammonium; bromide → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) + N-methyl(p-nitroaniline) (100-15-2)

Conditions	Yield
With water; palmitate ion at 30℃; Rate constant; other catalysts;

N,N-dimethylaminododecane (112-18-5) + XCH2COOH → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
Stage #1: N,N-dimethylaminododecane; XCH2COOH Stage #2: With Amberlit 420 In methanol; water for 2h;

1-dodecylbromide (143-15-7) + copper (I)-benzenethiolate → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: aq. ethanol / Heating View Scheme

N,N-dimethylaminododecane (112-18-5) + 2',3'-O-isopropylidene-5'-O-(chloroacetyl)uridine (95578-02-2) → 2',3'-O-isopropylidene-O2,5'-cyclouridine (3868-21-1) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
In acetonitrile Inert atmosphere; Reflux;

N,N-dimethylaminododecane (112-18-5) + chloroacetic acid (79-11-8) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
With potassium hydroxide In water at 95℃; for 3.58333h; Temperature; Concentration; Time;
Stage #1: chloroacetic acid With sodium hydroxide pH=8; Stage #2: N,N-dimethylaminododecane at 80℃; for 6h; Temperature;

1-dodecylbromide (143-15-7) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; benzene / 20 h / 20 - 25 °C / 760.05 Torr 2: water / 1 h / 90 - 95 °C View Scheme
Multi-step reaction with 2 steps 1: water; benzene / 20 h / 20 - 25 °C 2: water / 1 h / 90 - 95 °C View Scheme

ethylene glycol mono-n-dodecyl ether (4536-30-5) → carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; phosphorus tribromide / 2 h / -10 - 25 °C 2: water; benzene / 20 h / 20 - 25 °C 3: water / 1 h / 90 - 95 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine; phosphorus tribromide / 2 h / -10 - 25 °C 2: sodium hydroxide / water; benzene / 20 h / 20 - 25 °C / 760.05 Torr 3: water / 1 h / 90 - 95 °C View Scheme

3,4,5-trihydroxybenzoic acid (149-91-7) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → dodecyldimethylglycine gallate

Conditions	Yield
In methanol at 25℃; for 1h;	99%

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) + L-Pyroglutamic acid (98-79-3) → C16H34NO2(1+)*C5H6NO3(1-)

Conditions	Yield
In ethanol at 25℃; for 0.5h;	98%

Bis(2-ethylhexyl)phosphoric acid (298-07-7) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → C16H34NO2(1+)*C16H34O4P(1-)

Conditions	Yield
In ethanol at 25℃; for 0.5h;	98%

cholic acid (81-25-4) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → C16H34NO2(1+)*C24H39O5(1-)

Conditions	Yield
In ethanol at 25℃; for 0.5h;	95%

gluconic acid (526-95-4) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → C16H34NO2(1+)*C6H11O7(1-)

Conditions	Yield
In ethanol at 25℃; for 0.5h;	92%

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → N-dodecylbetainium chloride (55142-08-0)

Conditions	Yield
With hydrogenchloride In water; acetone at 60℃; for 1h;	90%

α-ketoglutaric acid (328-50-7) + carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → 2C16H34NO2(1+)*C5H4O5(2-)

Conditions	Yield
In ethanol at 25℃; for 0.5h;	82%

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) + isobutyl chloroformate (543-27-1) → Dodecyl-(2-isobutoxycarbonyloxy-2-oxo-ethyl)-dimethyl-ammonium; chloride

Conditions	Yield
With 4-methyl-morpholine In N,N-dimethyl-formamide at -15℃; for 0.0833333h;

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → Dodecyl-[(2-mercapto-ethylcarbamoyl)-methyl]-dimethyl-ammonium; chloride

Conditions	Yield
Multi-step reaction with 2 steps 1: N-methylmorpholine / dimethylformamide / 0.08 h / -15 °C 2: N-methylmorpholine / dimethylformamide / 1 h / 0 °C View Scheme

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → N,N'-bis(N-dodecyl-N,N'-dimethylglycine)1,4-diaminobutane dihydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: N-methylmorpholine / dimethylformamide / 0.08 h / -15 °C 2: 40 percent / N-methylmorpholine / dimethylformamide / 1 h / 0 °C View Scheme

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → N,N'-bis(N-dodecyl-N,N'-dimethylglycine)cystamine dihydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: N-methylmorpholine / dimethylformamide / 0.08 h / -15 °C 2: N-methylmorpholine / dimethylformamide / 1 h / 0 °C 3: O2 / H2O / Irradiation View Scheme
Multi-step reaction with 2 steps 1: N-methylmorpholine / dimethylformamide / 0.08 h / -15 °C 2: 50 percent / N-methylmorpholine / dimethylformamide; H2O View Scheme

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → dodecylbetainium 2,4-dichlorophenoxyacetate

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / acetone; water / 1 h / 60 °C 2: methanol / 3 h / 60 °C View Scheme

carboxymethyl-dodecyl-dimethyl-ammonium betaine (683-10-3) → dodecylbetainium 4-chloro-2-methylphenoxyacetate

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / acetone; water / 1 h / 60 °C 2: methanol / 3 h / 60 °C View Scheme

Upstream product

• 112-18-5 N,N-dimethylaminododecane 
• 3926-62-3 sodium monochloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 17283-72-6 methyl N-dodecyl-N,N-dimethylglycinate chloride 
• 77814-51-8 methyl N-dodecyl-N,N-dimethylglycinate 
• 143-15-7 1-dodecylbromide 
• 95578-02-2 2',3'-O-isopropylidene-5'-O-(chloroacetyl)uridine 
• 79-11-8 chloroacetic acid 
• 4536-30-5 ethylene glycol mono-n-dodecyl ether 
• 7748-25-6 potassium chloroacetate 
• 112-53-8 1-dodecyl alcohol 
• 7148-06-3 N,N-dimethylglycine methyl ester 

Downstream Products

• 55142-08-0 N-dodecylbetainium chloride 

Relevant articles and documents

Size and Shape of Micelles in the Ternary System n-Dodecylbetaine/Water/1-Pentanol

The phase diagram of the system n-dodecylbetaine/water/1-pentanol is first presented.The use of several experimental techniques, namely (principally) small-angle X-ray scattering and fluorescence probe studies, allows us to obtain the size and the shape of the micelles in the L1 phase.It is shown that the most probable shape corresponds to elongated aggregates, the self-consistency of the results leading to exclude the other shapes.

Synthesis and properties of gallate ionic liquids

An efficient method for the synthesis of novel antioxidants in the form of ionic liquids (ILs) was described in the framework of this study. The ILs were obtained by the reaction of quaternary ammonium hydroxides with gallic acid as well as the protonatio

Lauryl betaine preparation method

The present invention discloses a lauryl betaine preparation method, which comprises: a, adding ethyl 2-(p-toluenesulfonyloxy)acetate andacetone or methanol to a reactor, and completely and uniformly stirring to obtain a mixture; b, adding dodecyl dimethyl dimethylamine to the mixture in a dropwise manner while stirring, and heating and carrying out a complete stirring reaction after completing the adding; c, after completing the substitution reaction, distilling under a conventional atmospheric pressure to remove half of the solvent, adding p-toluenesulfonic acid aqueous solution having a mass concentration of 15-20%, and continuously heating and carrying out the stirring reaction; and d, after completing the hydrolysis reaction, distilling to remove the majority of the solvent, removing impurity ions from the residue by using an ion-type macroporous adsorption resin to obtain a lauryl betaine aqueous solution, and distilling under a conventional atmospheric pressure to remove the water to obtain the viscous liquid lauryl betaine. According to the present invention, with the method, the high quality lauryl betaine can be prepared, and the product equipment corrosion loss can be reduced.

AMPHOTERIC BETAINE COMPOUNDS

Disclosed are a variety of amphoteric compounds containing a quaternary nitrogen group, a covalently bound counterion, and an ester or amide group. These amphoteric compounds can be advantageously prepared via a chemoenzymatic green process, and exhibit good surfactant properties.

Production method of gel emulsifier intermediate N-dodecyl betaine

The invention relates to a production device of gel emulsifier intermediate N-dodecyl betaine. The production device mainly comprises a dodecyl dimethyl tertiary amine storing tank, a feed pump, a neutralization tank, a neutralization pump, a reaction kettle and a finished product pump in such a connection relation that the dodecyl dimethyl tertiary amine storing tank is communicated with the feed pump, the feed pump is communicated with the reaction kettle, the reaction kettle is communicated with the neutralization pump, the neutralization pump is communicated with the neutralization tank, and the reaction kettle is communicated with the finished product pump, wherein the dodecyl dimethyl tertiary amine storing tank is a horizontal storing tank, the total volume of the dodecyl dimethyl tertiary amine storing tank is 6.9-8.11m, the diameter of a cylinder is 1300-1650mm, the length is 2650-4700mm, and the thickness of a seal head is 8.1-8.9mm; the feed pump is a single-level single-suction centrifugal pump, the rotational speed is 2800-2890r/min, the flow is 7.9-11.5m/h, the pumping head is 32.5-34m, and the power is 1.47-2.01KW; the nominal volume of the reaction kettle is 620-900L, the capacity of a jacket is 295-530L, the diameter of an outer pot is 1150-1300mm, and the stirring speed is 63-75r/min.

Gel emulsifier midbody N - dodecyl betaine apparatus for producing

The utility model provides a gel emulsifier midbody N dodecyl betaine apparatus for producing mainly includes: 12 tertiary amine storage tanks, feedstock pump, neutralizing tank are in, and pump, reation kettle, finished product pump, relation of connection between this apparatus for producing component parts does: 12 tertiary amine storage tanks are connected with feedstock pump, and feedstock pump is connected with reation kettle, and reation kettle is connected with the pump in with is connected with the neutralizing tank with the pump in, and reation kettle is connected with finished product pump, wherein, are 12 tertiary amine storage tanks horizontal tank, full volume 6.9 8.11m3, diameter of drum 1300 - 1650mm, 2650 - 4700mm of length, head thickness 8.1 - 8.9mm, is feedstock pump single -stage and single -suction centrifugal pump, rotational speed 2800 2890rmin, flow 7.9 11.5m3h, lift 32.5 34m, power 1.47 2.01KW, reation kettle nominal volume 620 does 900L press from both sides cover capacity 295 530L, the outer pot diameter 1150 1300mm, agitation speed 63 75rmin.

Synthesis of some acyclic quaternary ammonium compounds. Alkylation of secondary and tertiary amines in a two-phase system

A series of acyclic symmetrical and asymmetrical quaternary ammonium chlorides of the general formula R1R2R3N+AR4Cl- (R1 = Me, Bu; R2 = n-C12H25, PhCH2, C n H2n+1(OCH2CH2) m, n = 9 and 12, m = 1 and 2; R3 = n-C12H25, PhCH2, HOCH2CH2,-OOCCH2; R4 = n-C12H25, PhCH2; A = (CH2CH2O)1,2, CH2C(O)O) was synthesized by the alkylation of tertiary amines in a two-phase system containing water. A convenient method for the synthesis of the initial symmetrical and asymmetrical tertiary amines of the general formula MeNR1R2 (R1 = Me, Bu; R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2) m, n = 9 and 12, m = 1 and 2) in an organic phase-aqueous phase heterogeneous system, which allows the use of aqueous solutions of alkali and amines, was developed. The improved method for the preparation of intermediate ethylene glycol and diethylene glycol monoethers is monoalkylation of glycols in dioxane using solid KOH in a two-phase system.

CONTINUOUS METHOD FOR MANUFACTURING BETAINE AQUEOUS SOLUTION

The present invention relates to a method for continuously preparing a betaine aqueous solution, including the reaction of an amine with an ω-halocarboxylic acid, in the presence of water and a base. Said method is characterized in that it is carried out in a device consisting of at least two consecutive reactors (R1) and (R2), the reactor (R2) being a tubular reactor.

AMINO- OR AMMONIUM-CONTAINING SULFONIC ACID, PHOSPHONIC ACID AND CARBOXYLIC ACID DERIVATIVES AND THEIR MEDICAL USE

The present invention relates to amino- or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives, in particular the compounds of formula 1, 2, 3, 4, 5 or 6, and their medical use, including their use in the treatment, prevention or amelioration of an inflammatory, autoimmune and/or allergic disorder.

Synthesis of novel 5'-uridine-head amphiphiles as model for DNA molecular recognition

Here we describe uridine functionalization in the 5' position, which provides new classes of cationic and nonionic amphiphiles specifically designed as DNA transfection agents. The synthetic procedures developed to obtain the cationic uridine-head surfactants prevented intramolecular cyclization that occurs when uridine is functionalized in this position without using protecting groups in the uracil.