Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2010-04-19
2010-12-14
Witherspoon, Sikarl A (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S827000
Reexamination Certificate
active
07851660
ABSTRACT:
A process for making perillyl alcohol is disclosed. The process comprises isomerizing a starting material comprising trans-isocarveol at a temperature within the range of 100° C. to 220° C. in the presence of a Group 5 metal catalyst to produce perillyl alcohol. We surprisingly found that trans-isocarveol, which can be selectively produced from a commercially available mixture of cis- and trans-LMO, can be isomerized directly to perillyl alcohol. Yields of perillyl alcohol are improved when the isomerization is performed under an inert atmosphere and/or in the presence of a phenolic antioxidant. Performing the isomerization in the presence of a high-boiling alcohol and/or distilling the perillyl alcohol product from the reaction mixture in the presence of a high-boiling alcohol, enhances yields and maximizes catalyst use. The resulting distillation residue, which contains recovered Group 5 metal catalyst, is valuable for catalyzing additional trans-isocarveol isomerizations.
REFERENCES:
patent: 3925485 (1975-12-01), Chabardes et al.
patent: 3956404 (1976-05-01), Walling et al.
patent: 3957856 (1976-05-01), Ansari et al.
patent: 3993604 (1976-11-01), Thomas et al.
patent: 4254291 (1981-03-01), Kane
patent: 4306099 (1981-12-01), Fetizon et al.
patent: 5994598 (1999-11-01), Chastain et al.
patent: 6835686 (2004-12-01), Kolomeyer et al.
U.S. Appl. No. 12/799,119, filed Apr. 19, 2010, Kolomeyer et al.
Bessiere, Y. et al., “Isomerization of Limonene Epoxides, Allylic Rearrangement of p-Metntha-1(7),8-dien-2-ols: Preparation of Perilla Alcohol,”Journal of Chemical Research(S), 1977, 304-305.
Tius, M., et al., “A Convenient Synthesis of (R)-(+)-Perillaldehyde,”Synthetic Communications, 18, (16&17), 1905-1911, (1988).
Ferone Douglas A.
Kolomeyer Gennadiy G.
Millennium Specialty Chemicals, Inc.
Schuchardt Jonathan L.
Witherspoon Sikarl A
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