Amine sulfate dialkyl

All lation. Alkylating agents such as diaLkyl sulfates and alkyl hahdes react with ahphatic amine oxides to form trialkylalkoxyammonium quaternaries. For example (33), methyl iodide reacts with trimethyl amine oxide to form trimethylmethoxyammonium iodide... 

QuaterniZation. Quaternary ammonium compounds are formed by alkylation of alkyl, alkyl dimethyl, dialkyl, and dialkylmethyl fatty amines with methyl chloride, dimethyl sulfate, or benzyl chloride (1,3,7,12,29). 

The single largest market use for quaternary fatty amines is in fabric softeners. Monoalkyl quaternaries (chloride) have been used in Hquid detergent softener antistat formulations (LDSA), dialkyl dimethyl quaternaries (chloride) in the rinse cycle, and dialkyl dimethyl quaternaries (sulfate) as dryer softeners. 

SuIfona.tlon, Sulfonation is a common reaction with dialkyl sulfates, either by slow decomposition on heating with the release of SO or by attack at the sulfur end of the O—S bond (63). Reaction products are usually the dimethyl ether, methanol, sulfonic acid, and methyl sulfonates, corresponding to both routes. Reactive aromatics are commonly those with higher reactivity to electrophilic substitution at temperatures > 100° C. Tn phenylamine, diphenylmethylamine, anisole, and diphenyl ether exhibit ring sulfonation at 150—160°C, 140°C, 155—160°C, and 180—190°C, respectively, but diphenyl ketone and benzyl methyl ether do not react up to 190°C. Diphenyl amine methylates and then sulfonates. Catalysis of sulfonation of anthraquinone by dimethyl sulfate occurs with thaHium(III) oxide or mercury(II) oxide at 170°C. Alkyl interchange also gives sulfation. 

Sulfonates react with a variety of nucleophiles. Synthesis of M A -bis(trifluoro-methyl)aminotnfluoromethanesulfonate and its reactions with nucleophiles were investigated [33] (equation 31) (Table 13). Nucleophilic attack occurs at either nitrogen or sulfur amines give complex mixtures [33]. Polyfluoroalkyl fluorosul-fates react with amines, alcohols, or alkoxides to yield polyfluoroalkyl sulfamates and dialkyl sulfates, respectively [34] (equation 32) (Table 13). In these reactions. 

The method gives better yields, utilizes more readily available starting materials, and is much less laborious than the hydrolysis of N-methyl-N-alkylarenesulfonamides and -nitroso-N, N-di-alkylanilines, or the lithium aluminum hydride reduction of alkyl isocyanates. Compared to the closely related procedure of Lucier, Harris, and Korosec,12 in which the N-benzylidenealkyl-amine is treated with dialkyl sulfate at atmospheric pressure, the present procedure tends to give higher yields and purer products, but it is less convenient because of the need for a pressure vessel. 

The preparation of diallyl cyanamide by the above method has only recently been described in the literature.1 However, other dialkyl cyanamides have been prepared by the following methods the action of chlorocyanogen or bromocyanogen on dialkyl amines 2 the reaction of dialkylchloroamines with potassium cyanide 3 the action of bromine on a mixture of dialkyl amines and potassium cyanide 4 the action of alkyl halides on disilver cyanamide5 and on disodium cyanamide.6 Dimethyl cyanamide has also been prepared by the action of dimethyl sulfate on lime nitrogen 7 and on cyanamide. 8... 

The variety of substances used as additives in polymers is considerable. For example, the fillers may include china clay, various forms of calcium carbonate, talc, silicas (diatomaceous silica), silicates, carbon black, etc. The impact modifiers typically include other polymers. Plasticizers include certain polymers with low (oligomers), dialkyl phthalates, dialkyl sebacates, chlorinated paraffin waxes, liquid paraffinic fractions, oil extracts, etc. Heat stabilizers include heavy metals salts such as basic lead carbonate, basic lead sulfate, dibasic lead phosphite (also acting as a light stabilizer), dibasic lead phthalate, stearates, ricinoleates, palmitates and octanoates of cadmium and barium, epoxide resins and oils, amines, diphenylurea, 2-phenylindole, aminocrotonates. The antioxidants include tris-nonyl phenyl phosphite, 2,6-di-ferf-butyl-p-cresol (BHT), octadecyl-3,5-di-terf-butyl-4-hydroxyhydrocinnamate, etc. The UV stabilizers include modified benzophenones and benzotriazoles. Processing lubricants include calcium stearate, stearic acid, lead stearate, various wax derivatives, glyceryl esters and long-chain acids. Fire retardants include antimony oxide, some pyrophosphates, etc. 

In many cases amines are alkylated when merely heated with dialkyl sulfates. For instance, AjA-diethyl-p-anisidine was obtained (61% yield) by heating /7-anisidine (1 mole) with diethyl sulfate (2.2 moles) for 4 h at 120-130°, N,N-diethyl-p-toluidine (91%) analogously after 6 hours heating, and A TV-diethyl-m-phenetidine (52%) after 8 hours heating.836... 

Pure primary amines may also be obtained by alkylating urotropine with dialkyl sulfates and cleaving the resulting quaternary salt.839... 

As when dialkyl sulfates are used, the products formed from free amines and sulfonic esters are almost always mixtures of all the possible alkylation stages of the amine. Nevertheless, formation of specific products can be favored by choice of techniques. When a solvent is needed alcohol or acetone is usually chosen. 

Aliphatic Alkylamines. The aliphatic alkylamines are made in a variety of ways. For the lower amines, the action of an alcohol on ammonia or an amine in the vapor phase over aluminum oxide is a common method of preparation (see Chap. 8). For the higher amines, the action of an alkyl halide on ammonia in the liquid phase, often in the presence of the corresponding alcohol, is frequently used. Heat is often needed in the liquid-phase reactions, and autoclaves are then needed. The dialkyl sulfates are of particular importance because of their higher boiling points and ability to act as an alkylating agent on being heated in ordinary nonpressure vessels. 

Nazareth, A. Joppich, M. Pauthani, A. Fisher, D. Giese, R.W. Alkylation with dialkyl sulfate and ethyl-diisopropyl amine. J. Chromatogr. 1985,319, 382-386. 

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