Fatty nitrile

Nitrile Process. Fatty nitriles are readily prepared via batch, Hquid-phase, or continuous gas-phase processes from fatty acids and ammonia. Nitrile formation is carried out at an elevated temperature (usually >250° C) with catalyst. An ammonia soap which initially forms, readily dehydrates at temperatures above 150°C to form an amide. In the presence of catalyst, zinc (ZnO) for batch and bauxite for continuous processes, and temperatures >250° C, dehydration of the amide occurs to produce nitrile. Removal of water drives the reaction to completion. 

Nitrile Intermediates. Most quaternary ammonium compounds are produced from fatty nitriles (qv), which are ia turn made from a natural fat or oil-derived fatty acid and ammonia (qv) (Fig. 2) (see Fats AND FATTY oils) (225). The nitriles are then reduced to the amines. A variety of reduciag agents maybe used (226). Catalytic hydrogenation over a metal catalyst is the method most often used on a commercial scale (227). Formation of secondary and tertiary amine side-products can be hindered by the addition of acetic anhydride (228) or excess ammonia (229). In some cases secondary amines are the desired products. 

Fig. 2. Quaternaries from fatty nitriles where R is a fatty alkyl group.

These compounds and their derivatives can be manufactured using relatively simple equipment compared to that required for the fatty nitrile derivatives. Cyclization of amidoamines to imidazolines requires higher reaction temperatures and reduced pressures. Prices of imidazolines are therefore high. 

Other modifications of the polyamines include limited addition of alkylene oxide to yield the corresponding hydroxyalkyl derivatives (225) and cyanoethylation of DETA or TETA, usuaHy by reaction with acrylonitrile [107-13-1/, to give derivatives providing longer pot Hfe and better wetting of glass (226). Also included are ketimines, made by the reaction of EDA with acetone for example. These derivatives can also be hydrogenated, as in the case of the equimolar adducts of DETA and methyl isobutyl ketone [108-10-1] or methyl isoamyl ketone [110-12-3] (221 or used as is to provide moisture cure performance. Mannich bases prepared from a phenol, formaldehyde and a polyamine are also used, such as the hardener prepared from cresol, DETA, and formaldehyde (228). Other modifications of polyamines for use as epoxy hardeners include reaction with aldehydes (229), epoxidized fatty nitriles (230), aromatic monoisocyanates (231), or propylene sulfide [1072-43-1] (232). 

Figure 57.28. The retention of olefin functionality (% IV) during the hydrogention of fatty nitriles to fatty amines over activated Ni with and without H2CO modification.

Fatty nitriles, preparation, 2 524-525 Fatty odor, 3 228t... 

Fatty nitriles Fatty oils Fauj asite... 

The simplest class of lipids are FAs. This group includes various types of fatty acids, eicosanoids, fatty alcohols, fatty aldehydes, fatty esters, fatty amides, fatty nitriles, fatty ethers, and hydrocarbons. Many FAs, especially the eicosanoids derived from n-6 and n-3 polyunsaturated fatty acids, have... 

A large excess of ammonia suppresses formation of di- and trialkylamines. With a rhodium-on-carbon catalyst in process conditions of 75°C and 50 psig plus continuous removal of ammonia, the reduction of propionitrile with hydrogen proceeds with greater than 85% selectivity for di-n-propylamine, with 2 to 5% mono-n-propylamine coproduct. Several companies produce amines in the C 2 to Ci8 range from fatty nitriles by this route116. 

The manufacturing process for cationic surfactants can be divided into two parts. The first part is the creation of an alkylated amine. Several processes can achieve this endpoint and are briefly reviewed below. The largest volume process which was developed by Armour starts with tallow triglyceride which is split to yield fatty acid and glycerine. The fatty acid is reacted with ammonia and converted to fatty nitrile under high pressure and temperature conditions... 

The main raw material is the fatty nitrile derived from the reaction of fatty acid with ammonia. Catalytic hydrogenation of the nitrile produces the amines. The amines are available as primary, secondary, and tertiary amine, depending on the number of the alkyl groups attached to the nitrogen atom. 

Reduction of several aliphatic and aromatic nitriles to the corresponding amines has also been reported. A palladium-coated nickel cathode, a carbon anode, and dilute hydrochloric acid have been used. A copper cathode, a graphite anode, and a promoter such as Raney nickel have been found satisfactory for the reduction of long-chain fatty nitriles. 

Synonyms Nitriles, tallow Tallow (alkyl nitrile) Classification Fatty nitrile Precaution Hazardous material Uses Detergent wetting agent rust inhibitor chemical intermediate... 

Figure 14.1. Preparation of cationics from fatty nitriles...

Nearly all fatty nitrile plants require considerable technological expertise and capital investment to operate. Presently, the largest volume product types are the di(hydrogenated tallow) alkyldimethylammonium (DHTMAC) quaternaries which are sold as the chloride or methyl sulfate salts. 

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