Patent GB-646951-A (GB)
Title: Improvements in the production of amino alcohols
IPC: C07C215/02
Filed: 1947-12-22
Abstract: A tertiary amino alcohol of formula <FORM:0646951/IV (b)/1> where R1 and R2 are hydrocarbon groups which may together form a hydroaromatic ring, and at least one of R3 and R4 is hydrogen and the other may be hydrocarbon, which may contain alkoxy, or the group <FORM:0646951/IV (b)/2> is prepared by the catalytic hydrogenation, e.g. with Raney nickel, of a tertiary keto alcohol of formula <FORM:0646951/IV (b)/3> in the presence of an excess of at least 4 mols. of ammonia or a primary amine at a temperature between about 60-125 DEG  C. and a pressure at least 500lb. p.s.i.  R1 and R2 may be alkyl, e.g. methyl, aryl, e.g. phenyl, or aralkyl, e.g. benzyl. R3 and R4 may be aralkyl, e.g. benzyl, aryl, e.g. phenyl, alkyl, e.g. ethyl, or cycloaliphatic, e.g. cyclohexyl, or they may be both hydrogen.  The excess of ammonia or amine is preferably 6 mols.  The pressure range may be 100-1000lb. p.s.i. Ammonia, if used, may be aqueous or in some other solvent. With lower temperatures and pressures in the reaction, amines of formula <FORM:0646951/IV (b)/4> are formed.  With fatty acids, e.g. stearic, salts of the amino alcohols are formed.  In the examples, 3-methyl-3-butanol-2-one is reduced in presence of (1) aqueous ammonia to give 3 - methyl - 2 - amino - 3 - butanol; (5) aqueous methylamine to give 3-methyl-2-methylamino-3-butanol; and (6) aniline to give 3-methyl-2-anilido-3-butanol; the use of the ketones 3-ethyl-3-butanol-2-one, 1-acetylcyclohexanol, 3-isobutyl-3-butanol-2-one, and 3-phenyl-2-butanol-2-one, and the amines p-methoxyaniline, naphthylamine and toluidines is also exemplified.  Specification 313,617, [Class 2 (iii)], is referred to. Carbamates are formed when the above amino alcohols are exposed to carbon dioxide.  Pyrrole derivatives are formed on heating the amino-alcohols with 1 : 4-diketones, e.g. 3-methyl-2-amino-3-butanol and acetonylacetone, give 1 - (11 : 21 - dimethyl - 21 - hydroxypropyl) - 2 : 5-dimethylpyrrole.  With acylating agents the amino alcohols initially give amides, e.g. stearamides; under more vigorous conditions the free hydroxyl group is also esterified.  The Specification as open to inspection under Sect. 91 comprises also cases in which R3 and R4 are both hydrocarbon at the same time, and reaction conditions which include an excess of ammonia or amine of less than four mols.  Examples are given of the acylation of amino alcohols.  This subject-matter does not appear in the Specification as accepted.ALSO:The fatty acid salts, e.g. stearates, of the following amino-alcohol, and the products (amides, e.g. stearamides), obtained by acylating the amino group of the amino-alcohol, are used as emulsifiers, e.g. to emulsify water and carbon tetrachloride.  The amino-alcohol is of formula <FORM:0646951/III/1> where R1 and R2 are hydrocarbon groups which may together form a ring, R3 is hydrogen, and R4 is hydrogen or hydrocarbon which may be substituted by an alkoxy group.  The hydrocarbon groups may be alkyl, e.g. ethyl, aryl, e.g. phenyl or naphthyl, aralkyl, e.g. benzyl, hydroaromatic, e.g. cyclohexyl.