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US 3,933,873 AGranted
Preparation of omega-aminoalkanoic acids
AssigneeTexaco Inc.
InventorsRichard F. Love, Kablaoui Mahmoud S., Roger G. Duranleau
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Abstract
A method for preparing omega-aminoalkanoic acids by the steps of (1) nitro-oxidizing a cycloalkene to a cyclic alpha-nitroketone, (2) cleaving and esterifying a cyclic alpha-nitroketone with an alcohol to form an alkyl omega-nitroester, (3) catalytically hydrogenating the nitroester to an aminoester and (4) hydrolyzing the aminoester to an aminoalkanoic acid.
Claims27
A method for preparing omega-aminoalkanoic acids which conprises:
- a. simultaneously contacting at a temperature between about 0.degree. to 40.degree.C. a solution containing a C.sub.7 to C.sub.20 cycloalkene, a denitrating agent and an aprotic organic solvent with dinitrogen tetroxide and oxygen, wherein said denitrating agent is selected from the group consisting of 2-pyrrolidinones, ##EQU7## where R.sup.1, R.sup.2, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are alkyl of from 1 to 5 carbons and R.sup.3, R.sup.4 and R.sup.5 are hydrogen or alkyl of from 1 to 5 carbons, where the mole ratio of cycloalkene to denitrating agent is above about 0.5:1 to about 2:1, thereby forming 2-nitrocycloalkanone,
- b. contacting 2-nitrocycloalkanone with an alcohol, wherein said alcohol is a primary or secondary alcohol corresponding to the formula R'OH where R' is an alkyl group of from 1 to 20 carbon atoms, in a non-aqueous environment at a temperature of from about 20.degree. to 200.degree.C. thereby forming an alkyl omega-nitroalkanoate,
- c. contacting said alkyl omega-nitroalkanoate with hydrogen and a Group VIII metal catalyst at a temperature of from 20.degree. to 300.degree.C. under a hydrogen pressure of 500 to 1500 p.s.i.g. thereby forming an alkyl omega-aminoalkanoate, and
- d. contacting said alkyl omega-aminoalkanoate with water at a temperature of from 150.degree. to 300.degree.C.
1 more element
Dependencies are inferred from the claim text.