Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-12-22
1999-03-23
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568460, C07C 4545
Patent
active
058862340
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. National Stage Application of PCT/JP96/01720 filed Jun. 21, 1996 now WO97/00844 published Jan. 9, 1997.
TECHNICAL FIELD
The present invention relates to a process for producing cyclic unsaturated aldehydes, and more specifically, it relates to a process for efficiently producing cyclic unsaturated aldehydes useful as the raw materials of traction oils and unsaturated polyester resins, modifiers for phenolic resins, and functional chemical products such as monomers for functional resins through the Diels-Alder reaction at a low cost without causing the corrosion of an apparatus and without requiring any treatment after the reaction.
BACKGROUND ART
Cyclic unsaturated aldehydes are compounds which are useful as the raw materials of traction oils and unsaturated polyester resins, modifiers for phenolic resins, and functional chemical products such as monomers for functional resins.
On the other hand, a fluid for traction drive is used in a traction drive device (a friction drive device by rolling contact), for example, a continuously variable transmission for a car or a continuously variable transmission for an industry, and such a fluid requires a high traction coefficient, stability to heat and oxidation, and economy. economy.
Known examples of the fluid for the traction drive include hydrocarbon compounds having a norbornane skeleton such as aldehydes are intermediates for synthesis (Japanese Patent Application Laid-open No. 95295/1991), and hydrocarbon compounds having a aldehydes are intermediates for synthesis (Japanese Patent Application Laid-open No. 9134/1993). reacting cyclopentadiene or methylcyclopentadiene with crotonaldehyde in accordance with the Diels-Alder reaction, and the above-mentioned reacting 1,3-cyclohexadiene or methyl-1,3-cyclohexadiene with crotonaldehyde in accordance with the Diels-Alder reaction. If no catalyst is used in such a Diels-Alder reaction, a high temperature of 100.degree. C. or more is required, because crotonaldehyde is less reactive. As a result, polymers of the cyclic conjugated diene compound and crotonaldehyde which are the starting materials are formed, or heavy compounds are formed by the further addition of the diene compound to the desired product, so that a yield of the desired product deteriorates inconveniently. As the catalysts for the Diels-Alder reaction, for example, Lewis acids such as titanium tetrachloride and ethylaluminum dichloride are heretofore known, but since they are liquid, a post-treatment is necessary after the reaction, and they are liable to corrode an apparatus. Therefore, they are not suitable for industrial production. In consequence, it has been demanded to develop a catalyst which does not require the post-treatment and which has no corrosive properties.
With regard to the Diels-Alder reaction of crotonaldehyde and cyclopentadiene, there has been reported an embodiment in which the reaction is carried out at 100.degree. C. for 4 hours without using any lead to the formation of large amounts of by-products such as a polymer of the cyclopentadiene and crotonaldehyde, and a condensate in which 2 mol of cyclopentadiene is added to crotonaldehyde, with the result that the selectivity of the desired product is low.
On the other hand, as reaction embodiments using the catalyst, there have been reported an embodiment in which the reaction is carried out at -78.degree. C. for 1.5 hours in the presence of a catechol boron bromide catalyst (yield=70%), an embodiment in which the reaction is carried out at -78.degree. C. for 1 hour by the use of a ferrocenium p. 1357 (1989)!, and an embodiment in which the reaction is carried out at -78.degree. C. for 1 hour in the presence of a 2-chloro-1,3,2-dithiaborane these methods, however, the homogeneous reaction is done at a low temperature in the presence of the expensive catalyst by the use of the solvent, and hence they cannot industrially be applied at all.
With regard to the Diels-Alder reaction using a heterogeneous solid catalyst, there are known an embodiment in which cyc
REFERENCES:
patent: 4992416 (1991-02-01), Bruns
Lucchetti et al, Tetrahedron Letters, 25(39), 1984.
Kelly et al, Tetrahedron Letters, vol. 30, pp. 1357-1360, 1989.
Olson et al, Tetrahedron Letters, vol. 32, pp. 5299-5302, 1991.
Catieviela et al, Tetrahedron, vol. 49, pp. 4073-4084,1993.
Ohno Takashi
Tsubouchi Toshiyuki
Geist Gary
Idemitsu Kosan Co. Ltd.
Padmanabhan Sreeni
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