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
• Article Data: 14

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

Different sources of media describe the Uses of 683-10-3 differently. You can refer to the following data:
1. Lauryl Betaine is an amphoteric surfactant derived from N-dodecyl-N,N-dialkanol amine with protein denaturing potency. Lauryl Betaine is mainly used in shampoo, personal hygiene products and oil field chemicals.
2. lauryl betaine is a skin-conditioning agent. In hair care, it is used as an anti-static conditioning agent and a foam booster.

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 
• 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 
• 79-11-8 chloroacetic acid 
• 95578-02-2 2',3'-O-isopropylidene-5'-O-(chloroacetyl)uridine 

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.

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.