Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1996-01-22
1998-06-23
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540354, 540359, 546261, 549 59, 549472, 549473, 558439, 568 38, 568 55, 568 57, C07B 3100, C07B 3300
Patent
active
057707294
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/JP94/02224 filed on Dec. 26, 1994.
TECHNICAL FIELD
The present invention relates to an ozonide reducing agent which is used for ozonolysis reaction of an organic compound, the reducing agent being useful for wide applications, safe and inexpensive from a commercial viewpoint and easy to treat for disposal.
BACKGROUND ART
Ozonolysis reaction has been widely commonly carried out as a method for preparing carboxylic acids, aldehydes, ketones and epoxides from organic unsaturated compounds or aromatic compounds. The reaction has been commonly resorted to for industrial purposes (Shin Jikken Kagaku Koza, Ozonolysis reaction is usually conducted by executing two steps, i.e., the step of causing ozone to act on an organic unsaturated compound or an aromatic compound to obtain an ozonide (peroxide) as an intermediate and the step of subjecting the ozonide to oxidization, reduction, hydrolysis and the like to obtain a stable object compound. The present invention relates to the latter step. The term "ozonide" used herein means any of the peroxides produced by ozonolysis reaction, such as .alpha.-ozonide, .beta.-ozonide, hydroxyperoxide, diperoxide and the like. Since an ozonide is in constant danger of explosion and the like, the step of treating the ozonide to obtain a safe object compound in a high yield is presumably a key step for ozonolysis reaction. Generally, the mildest method of treating an ozonide scarcely entailing a side reaction is said to be a published on September 20, 1975 by MARUZEN Co., Ltd.). Such method is carried out using various ozonide reducing agents. However, all of these reducing agents have some problems. The problems of respective reducing agents are given below in (1) to (7).
(1) Acetic acid-zinc reduction (J. Org. Chem., 25, 618 (1960)) is not applicable to a compound which is decomposed with an acid nor to a compound which must be decomposed at a low temperature. In addition, the reduction is not preferable since industrial wastes such as zinc oxide and the like are produced and cause environmental problems.
(2) Catalytic hydrogenation in the presence of a metallic catalyst such as Pt, Pd, Ni or the like (J. Am. Oil Chem. Soc., 42, 236 (1965)) always entails danger of explosion, since hydrogen is passed through a solution of a peroxide in the presence of a metal which is active to the solution. Further, when a halogen type solvent is used, the solvent as such is reduced by hydrogenation, and thus the kind of the solvent to be used is limited.
(3) In reduction with a metal such as Raney nickel, sodium boron hydride and the like (Can. J. Chem., 48, 1105 (1962)), the metal remains as industrial wastes after the treatment and poses environmental problems.
(4) In reduction with a trivalent phosphoric compound such as triphenylphosphine, phosphorous ester and the like (J. Org. Chem., 27, 4498 (1962)), phosphine oxide is not necessarily removed with ease from the reaction system after the treatment, while phosphorous ester produces a peculiar odor which presents an environmental problems. Further, the reduction is not advantageous in view of needs to consider environment and equipment, since a closed system may be needed to meet the strict standards for the drainage of phosphoric wastes.
(5) In reduction with dimethylsulfide which is most commonly used in laboratories (Tetrahedron Letters, 1966, 4273), the reducing agent exhibits a very high reducing power. However, this reducing agent is difficult to use for industrial purposes, since it causes an environmental problem of an offensive odor and involves difficulties of handling a compound with a low flash point.
(6) In reduction with dialkylsulfides and thiols (J. Org. Chem., 26, 4912 (1961)), the reducing agent can not find wide applications, since the agents exhibit a lower reducing power than the above-mentioned dimethylsulfide, produce a peculiar offensive odor, involve break of disulfide bond and side reactions such as addition reaction of thiol.
(7) Other sulfur-based ozonide reducing agents disclosed in lit
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Sasaoka Michio
Shiroi Takashi
Suzuki Daisuke
Otsuka Kagaku Kabushiki Kaisha
Rao Deepak R.
Shah Mukund J.
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