693-33-4

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(2,3)19-20(22)23/h4-19H2,1-3H3

Synthetic route

N,N-dimethylhexadecylamine (112-69-6) + sodium monochloroacetic acid (3926-62-3) → (N-hexadecyl-N,N-dimethylammonio)acetate (693-33-4)

Conditions	Yield
With ethanol at 100℃;
In ethanol Heating;
In ethanol; acetonitrile for 240h; Heating;

carboxymethyl-hexadecyl-dimethyl-ammonium; bromide (5466-51-3) → (N-hexadecyl-N,N-dimethylammonio)acetate (693-33-4)

Conditions	Yield
With silver carbonate

methyl N-hexadecyl-N,N-dimethylglycinate chloride (74729-09-2) → methanol (67-56-1) + (N-hexadecyl-N,N-dimethylammonio)acetate (693-33-4)

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

hexadecanyl bromide (112-82-3) → (N-hexadecyl-N,N-dimethylammonio)acetate (693-33-4)

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

Upstream product

• 112-69-6 N,N-dimethylhexadecylamine 
• 3926-62-3 sodium monochloroacetic acid 
• 5466-51-3 carboxymethyl-hexadecyl-dimethyl-ammonium; bromide 
• 74729-09-2 methyl N-hexadecyl-N,N-dimethylglycinate chloride 
• 112-82-3 hexadecanyl bromide 

Relevant academic research and scientific papers

The Effects of Zwitterionic Surfactant Systems upon Aromatic Nucleophilic Substitution

Reactions of OH(-) with 4-chloro-3,5-dinitrobenzoic acid (1) and 2-chloro-3,5-dinitrobenzoic acid (2) have been examined in solutions of N,N-dimethyl-N-tetradecylglycine (DTG) and N,N-dimethyl-N-hexadecylglycine (DHG).DTG and DHG ihibit hydroxydehalogenation of (1) and kinetic profiles for this reaction tend towards a plateau which assumes different values depending on the pH; hence the inhibition does not stop the reaction.Reactions of (2) with OH(-) in the presence of DTG and DHG exhibit a 'non-effect'.The important factor underlying this difference of behaviour between (1) and (2) in the presence of zwitterionic surfactants is probably the orientation of the substrates within the microaggregates.

Micellar Effects upon the Reaction of Betaine Esters with Hydroxide Ion

The reaction of hydroxide ion with methyl N,N,N-trimethylglycinate (1a) is inhibited by cationic micelles of C14H29NMe3Cl and C16H33NMe3Cl (MTACl and CTACl) besause the substrate is largely in the aqueous pseudophase which is depleted in OH- by the cationic micelles.Added Cl- displaces OH- from the micelles and decreases micellar inhibition.The corresponding reaction of methyl N-dodecyl-N,N-dimethylglycinate (1b) is catalyzed by both MTACl and CTACl which bind both reactants, but this catalysis is reduced by NaCl.Self-micellization of methyl N-hexadecyl-N,N-dimethylglycinate (1c) speeds reaction with OH-, and the rate constants reach plateau values with increasing substrate concentration and are independent of OH-.But addition of either CTACl or NaCl slows reaction because Cl- displaces OH- from the micelle.These diverse rate effents can be accounted for quantitatively in terms of the pseudophase ion-exchange model, which considers reactions in both the aqueous and micellar pseudophases and the distribution of both reactants between the pseudophases.