Oxidative carbonylation - A new syngas route to sebacic acid
Conventional technology for sebacic acid manufacture involves caustic soda decomposition of ricinoleic acid at high temperature. Principal co-products include 2-octanol and glycerine. Castor oil, which is the natural source for ricinoleic acid, is subject to price fluctuation due to cyclic crop production and protectionist policies by foreign governments. Castor oil technology is also at disadvantage because the overall product yield is low (<80%) and co-product 2-octanol must compete with cheap 2-ethylhexanol in plasticizer applications. These and other factors have resulted in a significant decline in the sebacic acid market from about 30 MM lbs. per year in the 70's to less that 5 MM lbs. in the 80's. Thus, there is a clear need for a new process to produce sebacic acid from cheap and readily available petrochemicals. In Japan, the need for new technology was answered by the development of an electrolytic route to sebacic acid. The Kolbe type electrolytic process involves dimerization of adipic acid half methyl ester salt to give dimethyl sebacate. The dimerization proceeds in 92% yield with 90% selectivity based on the adipate half ester. The main drawbacks of this process are the cost of energy utilized by the electrolytic process and the cost of adipic acid. A recent Chem Systems report indicates a small advantage for the Asahi electrolytic process with ample room for new technology development.
- Research Organization:
- ARCO Chemical Co., 3801 West Chester Pike, Newtown Square, PA
- OSTI ID:
- 5333927
- Report Number(s):
- CONF-860425-
- Journal Information:
- Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States), Journal Name: Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States) Vol. 31:1; ISSN ACPCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
BUTADIENE
CARBONYLATION
CARBOXYLIC ACIDS
CASTOR OIL
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
COBALT COMPLEXES
COMPLEXES
COST
DECOMPOSITION
DICARBOXYLIC ACIDS
DIENES
DIMERIZATION
ELECTROLYSIS
ELEMENTS
ESTERS
FLUIDS
GASES
HYDROCARBONS
HYDROGENATION
HYDROLYSIS
HYDROXY COMPOUNDS
ISOMERS
LYSIS
METALS
OCTANOLS
OILS
ORGANIC ACIDS
ORGANIC COMPOUNDS
OTHER ORGANIC COMPOUNDS
OXIDATION
PALLADIUM
PLATINUM METALS
POLYENES
POLYMERIZATION
SEBACIC ACID
SOLVOLYSIS
SYNTHESIS
SYNTHESIS GAS
TRANSITION ELEMENT COMPLEXES
TRANSITION ELEMENTS
VEGETABLE OILS
YIELDS