Aldehyde and alcohol compositions derived from seed oils

Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...

Reexamination Certificate

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C568S909000

Reexamination Certificate

active

07615658

ABSTRACT:
An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates. An alcohol composition derived by hydrogenation of the aforementioned aldehyde composition, containing a mixture of hydroxymethyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoalcohol {mono(hydroxymethyl)}, greater than about 1 to less than about 65 percent diol {di(hydroxymethyl)}, greater than about 0.1 to less than about 10 percent triol, tri(hydroxymethyl)-substituted fatty acids or fatty acid esters; preferably greater than about 3 to less than about 35 percent saturates; and preferably, less than about 10 percent unsaturates. The alcohol composition can be converted into an oligomeric polyol for use in the manufacture of polyurethane slab stock flexible foam.

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Kohlpaintner et al., Ullmann's Encyclopedia of Industrial chemistry, “Aldehydes, Aliphatic and Araliphatic”, 7th edition, John Wiley & Sons, Inc., pp. 6-7.
Khoe T. H. et al., Rigid Urethane Foams from Hydroxymethylated Linseed Oll and Polyol Esters, 1972, Journal of the American Oil chemists' Society, vol. 49, pp. 615-618.
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Co-pending International Patent Application PCT/US07/86222, “Aldehyde and Alcohol Compositions Derived From Seed Oils,” filed Dec. 3, 2007, currently unpublished, filed in the name of Wei-Jun Peng, David A. Babb, Aaron Sanders, Christopher Derstine, Jorge Jimenez, Zenon Lysenko, Kurt Olson, Joe Phillips, Brian Roesch, and Alan Schrock, claming the benefit of U.S. Appl. No. 60/874,213, filed Dec. 11, 2006.
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