Document Detail


Preparation of polycarboxylic acids by oxidative cleavage with oxygen / Co-Mn-Br system.
MedLine Citation:
PMID:  19915320     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Adipic acid and glutaric acid were obtained from 1-hydroxy-2- acetoxycyclohexane by oxidation cleavage using molecular oxygen in the presence of cobalt acetate, manganese acetate and hydrobromic acid in acetic acid solution. Applying this method to prepare dicarboxylic acids from unsaturated fatty acids, we proposed an efficient method where reaction mixture of unsaturated fatty acids and hydrogen peroxide - formic acid can be oxidative cleaved to produce dicarboxylic acids and monocarboxylic acids in acetic acid solution with molecular oxygen / Co-Mn-Br system. For example, azelaic acid, suberic acid and other dicarboxylic acid as dicarboxylic acids were obtained from industrial oleic acid, which contained oleic acid, palmitoleic acid, linoleic acid, and linolenic acid. As a result of investigation for reaction condition, increase of partial pressure of molecular oxygen or elevation of temperature accelerated oxidative cleavage, but total yields of azelaic acid and suberic acid were slightly decreased. Besides, effect of hydrohalic acids in liquid phase air oxidation in the presence of cobalt and manganese acetates was investigated to show that HBr was the most effective. Soybean acid and tall acid containing higher amounts of linoleic acid and linolenic acid than industrial oleic acid were also oxidatively cleaved to dicarboxylic acids.
Authors:
Kango Fujitani; Hiroshi Manami; Mikio Nakazawa; Tatsuo Oida; Tokuzo Kawase
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of oleo science     Volume:  58     ISSN:  1347-3352     ISO Abbreviation:  J Oleo Sci     Publication Date:  2009  
Date Detail:
Created Date:  2009-11-16     Completed Date:  2010-01-25     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101175339     Medline TA:  J Oleo Sci     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  629-37     Citation Subset:  IM    
Affiliation:
Environment Safety/Quality Assurance Department, New Japan Chemical Co., Ltd., Yagura-cho, Fushimi-ku, Kyoto 612-8224, JAPAN. fujitani-k@nj-chem.co.jp
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MeSH Terms
Descriptor/Qualifier:
Bromine / chemistry*
Carboxylic Acids / chemistry*
Cobalt / chemistry*
Fatty Acids, Unsaturated / chemistry
Manganese / chemistry*
Oxidation-Reduction
Oxygen / chemistry*
Chemical
Reg. No./Substance:
0/Carboxylic Acids; 0/Fatty Acids, Unsaturated; 7439-96-5/Manganese; 7440-48-4/Cobalt; 7726-95-6/Bromine; 7782-44-7/Oxygen

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