Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1994-06-03
1995-08-29
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
524216, 560 76, 585513, C07C 29141, C07C 31125, C07C 1102, C07C 230
Patent
active
054462134
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a method of dimerizing lower olefins such as ethylene, propylene, and butene using a specific catalyst and to a method of producing alcohols with the dimerized products.
The dimerized products of olefins produced through dimerization method according to the present invention may be hydroformylated by reaction with carbon monoxide and hydrogen in the presence of an VIII metal catalyst such as a rhodium catalyst. The resultant aldehydes may be hydrogenated to alcohols. Reaction of the said alcohols with carboxylic acids such as phthalic acid results in the formation of esters. These esters are of great industrial importance because of their application as plasticizers for synthetic resins.
BACKGROUND ART
Many investigations have been made on catalytic systems that permit uniform dimerization of lower monoolefins such as ethylene, propylene, and butene. As the catalysts, Ziegler-type catalysts having transition metals as central catalyst component are usually superior in dimer selectivity of the lower monoolefins. In particular, satisfactory results have been obtained in dimerization activity and selectivity with a catalyst obtained from a mixture of a nickel compound and organic aluminum halide.
Investigations have also been made on catalytic systems containing organic phosphorus compounds as third additives to the above mentioned catalytic component. It is known that these additives affect on catalytic activity and product selectivity. As these catalytic system containing the organic phosphorus compounds, 1 Japanese Patent Publication No. 46-34007 discloses a catalytic system comprising .pi.-allyl-type nickel complex, an organic aluminum halide and an organic phosphine. 2 Japanese Patent Publication Nos. 48-30241 and 50-30041 disclose catalytic systems comprising organic phosphine complexes of nickel represented by (R.sub.4 P).sup.+ (R.sub.3 PNiX.sub.3).sup.- and NiX'.sub.2 (PR'.sub.3).sub.2, respectively, where R represents hydrocarbyl group or hydrogen, X and X' each represents chlorine, bromine or iodine, and R' represents alkyl group. In addition, 3 Japanese unexamined Patent Publication No. 57-169433 discloses a catalytic system where halogenated phenol and water are added as fourth additives to a nickel compound, alkylaluminum and a trivalent phosphorus compound. It is disclosed to use, as the trivalent phosphorus compound in this case, trivalent organic phosphite compounds such as triethyl phosphite, tri-n-octyl phosphite, and triphenyl phosphite other than the above mentioned organic phosphine.
A large volume of C.sub.4 fraction are obtained during thermal cracking of naphtha or catalytic cracking of heavy oils. n-butenes extracted and separated from the fraction may be dimerized to improve octene yields. 4 Japanese Patent Publication 3-42249 discloses an approach to improve the octene yields with a catalytic system comprising a nickel compound selected from the group consisting of nickel salts of higher mono- or di-carboxylic acid having from 5 to 20 carbon atoms and a coordination complex of organic phosphine and nickel halide, an organic aluminum compound, and hydrogen.
Product olefins such as octenes obtained by the above mentioned dimerization method of lower olefins are hydroformylated and hydrogenated to alcohols having 9 carbon atoms (hereinafter, referred to as "INA") . These alcohols are known to be advantageously used as materials of plasticizers for polyvinyl chloride resin (British Patent No. 789,777and Japanese Patent Publication No. 61-15849, etc.).
As mentioned above, various organic phosphorus compounds have been proposed as ligands used for dimerization reaction. These compounds are, however, not always satisfactory in view of industrial applications. That is, the catalytic systems disclosed in the above 1 Japanese Patent Publication No. 46-34007 have faults that they are extremely unstable to air and thus have difficulty to deal with and that synthesis of the catalysis is complex. In addition the catalytic systems disclosed in the abov
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Higashino Yasuko
Kawaragi Yuuji
Sato Keiichi
Evans Joseph E.
Mitsubishi Kasei Corporation
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