Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1980-10-28
1982-06-01
Raymond, Richard
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549255, C07D30789
Patent
active
043327338
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to a process for liquefying a product of Diels-Alder reaction between maleic anhydride and decatriene, which is in a solid state at normal temperatures.
The resulting liquid acid anhydride is useful as a curing agent for epoxy resin and as a starting material for unsaturated alkyd. Hereinafter, the curing agent is referred to as a "hardener."
BACKGROUND OF THE INVENTION
Diels-Alder reaction products between decatriene and maleic anhydride (hereinafter referred to as "maleinized decatriene") such as a reaction product between maleic anhydride and allo-ocimene (hereinafter referred to as "maleinized allo-ocimeme") and a reaction product between maleic anhydride and myrcene (hereinafter referred to as "maleinized myrcene") can be used as hardeners for epoxy resins and as acid components for preparing unsaturated alkyd resin. However, many of these maleinized decatrienes are in a solid state at room temperatures and, from the point of view of reactivity and workability, it is desirable to liquefy them for the application to the above-described uses. Thus, liquefaction of the solid maleinized decatriene is necessary.
As the conventional process for liquefying maleinized allo-ocimene, B.P No. 906,017, for example, describes to liquefy maleinized allo-ocimene by heat-treating at temperatures of from 190.degree. to 240.degree. C. for a long time to cause thermal isomerization. However, such process of isomerization by heat-treating for a long time involves thermal decomposition even when conducted in a nitrogen stream, and hence it has the defect that liquefied, maleinized allo-ocimene is obtained only in a low yield after purification by distillation. And, the liquefied product obtained by the distillation purification often forms crystals 2 to 3 days after the preparation though it is temporarily liquid upon preparation and, even when it is in a liquid state at normal temperatures, it crystallizes at low temperatures of about 0.degree. to 10.degree. C. This specification describes, in Example 6, that maleinized allo-ocimene heat-treated at 210.degree. to 220.degree. C. for 14 hours crystallizes when allowed to stand, and that additional heat treatment for 5 hours at 210.degree. to 220.degree. C. provides a liquid product which does not crystallize even when allowed to stand at normal temperatures. However, such process capable of liquefying maleinized allo-ocimene only through long-time heat treatment is seriously disadvantageous from the point of industrial practice.
U.S. Pat. No. 3,078,235 describes a liquid epoxy resin hardener prepared by blending maleinized allo-ocimene, maleinized myrcene, and hexahydrophthalic anhydride. However, blending of the normally solid materials to liquefy them requires a melt-mixing step, thus leading to high cost.
The present invention provides a process for liquefying normally solid maleinized decatriene with ease and with industrial advantages.
DISCLOSURE OF THE INVENTION
This invention provides a process of liquefying normally solid maleinized decatriene by heat-treating it in the presence of a compound selected from the following groups (a) to (e):
(a) alkali metal salts;
(b) nitrogen-containing organic compounds;
(c) phosphorus-containing compounds selected from phosphines and quaternary phosphonium salts;
(d) thiocyanates; and
(e) solid basic compounds (except the alkali metal salts belonging to group (a) described above).
Furthermore, the present invention provides a process for liquefying maleinized decatriene which is in a solid state at room temperatures by previously heat-treating it in the presence of a compound selected from the above-described groups (a) to (e), and heat-treating the previously heat-treated product in the presence of an acidic catalyst or a noble metal catalyst.
As is stated above, normally solid maleinized decatriene can easily be liquefied by heat-treating in the presence of a compound selected from the above-described groups (a) to (e).
This liquefaction may be attributed to the formation of s
REFERENCES:
patent: 3873501 (1975-03-01), Saga
patent: 3927038 (1975-12-01), Liakumovich et al.
patent: 4198340 (1980-04-01), Ariga et al.
Craig, JACS, vol. 72, (1950), pp. 1678-1681.
Miura Mareki
Onuma Yoshinobu
Samejima Hiroshi
Mitsubishi Petrochemical Co. Ltd.
Raymond Richard
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