Patent GB-445148-A (GB)
Title: Process for preparing acid amides and anhydrous or substantially anhydrous alcohols
IPC: C11C3/00
Filed: 1935-05-09
Abstract: Acid amides are prepared by reacting carboxylic acids, or their anhydrides, halides, or esters, having acid radicles containing at least two carbon atoms, with liquid anhydrous ammonia at superatmospheric pressure and room temperature.  With esters, anhydrous alcohols are also obtained.  The reaction is represented <FORM:0445148/IV/1> More than one = CO group may be present as in polybasic acids, e.g. malonic or succinic, or their derivatives, or polybasic alcohols partly or completely esterified with mono- and/or polybasic acids.  R is any organic radical such as methyl, propyl, butyl, amyl, phenyl, benzyl, cinnamyl, naphthyl, pyridine, and quinoline.  It may contain substituents such as hydroxy, as in lactic or malic, amine groups, as in anthranilic, or halogen, in which case the amide may contain an amine group in place of halogen.  R1 may be OH, as in acetic or palmitic acid, halogen, as in acetyl bromide or benzoyl chloride, OR, for example, in melissyl palmitate, or OOCR, as in butyric anhydride. When an acid is the initial material water may be removed by reacting in the presence of anhydrous salts or by evaporation with ammonia.  Crude animal and vegetable oils, fats, waxes or resins may be used as initial materials.  Catalysts for the reaction may be used.  In examples: (1) coconut oil is mixed in an autoclave with excess of liquid ammonia.  After standing for 12 hrs. the amides which separate are filtered off and the filtrate distilled to recover ammonia and pure glycerol.  Sardine, olive, linseed, cotton-seed, soya bean or corn germ oil, or oils obtained by oxidation of paraffin wax may be similarly treated; (2) n butyl acetate and excess of liquid ammonia in a sealed vessel are kept at about 20 DEG  C. by water cooling.  Excess ammonia and then butyl alcohol are distilled off to give a residue of acetamide.  The alcohol may be converted to butyl acetate for re-use; (3) equimolecular quantities of acetic anhydride and liquid ammonia react at 20 DEG  C. for several hours, the acetamide being separated from the acetic acid by distillation, preferably under reduced pressure. No acetic acid is formed if two molecular proportions of ammonia are used; (4) butyryl chloride and excess of liquid ammonia are kept in a sealed tube.  Ammonia is distilled off, ammonium chloride washed out with water, and the residual butyramide recrystallized.  The process is applicable to soap manufacture.  Thus, the amides produced in example (1) may be hydrolyzed to obtain wax stock fatty acids.  The acid amides may be used as plasticizers, fillers, and fixatives in the artificial and natural resin, rubber and varnish industries, as paper sizers, or as lubricants in greases.  Thus, the amide of oleic acid, separated from the product of example (1), is used as a paper size, that of ricinoleic acid, prepared from castor oil, as a plasticizer or lubricator.  A comprehensive list of carboxylic compounds suitable as starting materials is given.  The Specification as open to inspection under Sect. 91 comprises also the use of elevated temperatures.  With solid initial materials, reaction is effected at about their melting points.  In an additional example, stearic acid is treated at about 70 DEG  C. This subject-matter does not appear in the Specification as accepted.ALSO:Acid amides, for example that of ricinoleic acid prepared from castor oil, are used as plasticizers in the varnish and allied industries, or as lubricants in greases.ALSO:Acid amides are used as plasticizers, fillers or fixatives in the resin and rubber industries, and as paper sizers. The amide of oleic acid, obtained for example from coconut oil, is used as a paper size, that of ricinoleic acid, prepared from castor oil, as a plasticizer.