National Distillers and Chemical Corporation

Emery Industries, Inc.

Henkel Corporation

Cognis IP Management Gmbh

Richard G Fayter

Allen L Hall

Eugene G Harris

Clarence E Clark, Jr

John F White

Kevin W Anderson

J Douglas Wenzel

Kenneth R McVay

Aliphatic polycarboxylic acids are made by a process comprising the steps of: (1) fermenting a beta-oxidation blocked C. tropicalis cell wherein both copies of the chromosomal POX5 gene and the chromosomal POX4A and POX4B genes are disrupted in a culture medium comprised of a nitrogen source, an organic substrate and a cosubstrate wherein the substrate is an unsaturated aliphatic compound having at least one internal carbon--carbon double bond and at least one terminal methyl group, a terminal carboxyl group and/or a terminal functional group which is oxidizable to a carboxyl group by biooxidation; (2) reacting the product of step (1) with an oxidizing agent to produce one or more polycarboxylic acids.

Process for making polycarboxylic acids

This invention relates to an efficient cis-to-trans isomerization of 1,4-dihalobutene-2 by means of a thiol or hydrogen bromide or hydrogen chloride catalyzed reaction.

Efficient cis-to-trans isomerization of 1,4-dihalobutene-2

This invention relates to the preparation of dialkyl-2-vinylcyclopropane-1,1-dicarboxylates involving the addition of an alcoholic metallic alkoxide to an organic solution of a 1,4-dihalobutene-2 and a malonic ester.

Process for the preparation of dialkyl

This invention relates to a two-step synthesis of high purity dialkyl 2-vinyl-cyclopropane-1,1-dicarboxylate in which a mixture of trans- and cis-1,4-dihalobutene-2 is first isomerized to essentially trans-1,4-dihalobutene-2 followed immediately by cyclocondensing the resultant trans-1,4-dihalobutene-2 with a malonic ester in the presence of an alcoholic solution of a metallic alkoxide.

Synthesis of high-purity dialkyl 2-vinylcyclopropane-1,1-dicarboxylate

Fragranced compositions and fragranced articles containing an aroma-augmenting or aroma-enhancing amount of a 2,3-dihydrofuran corresponding to the formula ##STR1## wherein R' is an alkyl group having from 1 to 4 carbon atoms, R** is an alkyl group having from 1 to 5 carbon atoms, R.sub.1 is an alkyl group having from 1 to 4 carbon atoms, R.sub.2 is hydrogen or an alkyl group having from 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 are hydrogen or a methyl group, and a process for obtaining same are provided.

Alkyl substituted-2,3-dihydrofuran fragrance compositions

2,3-Dihydrofurans having highly desirable odor characteristics closely mimicking that of natural products are provided herein. The 2,3-dihydrofurans correspond to the formula ##STR1## wherein R' is an alkyl group having from 1 to 4 carbon atoms, R** is an alkyl group having from 1 to 5 carbon atoms, R.sub.1 is an alkyl group having from 1 to 4 carbon atoms, R.sub.2 is hydrogen or an alkyl group having from 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 are hydrogen or a methyl group. The 2,3-dihydrofuran compounds are useful in the preparation of fragrance compositions and fragranced articles and can be employed in conjunction with known fragrance materials to augment or enhance the aromas thereof.

4-carbalkoxy-2-ethyl-2,3-dihydrofurans

Novel 2-vinyl(or ethyl)-1-cyanocyclopropane-1-carboxylates and 2-vinyl(or ethyl)-1-arylcyclopropane-1-carboxylates useful as herbicides, pesticides and chemical intermediates are provided. The invention also relates to a method of modifying plant growth by the application of vinyl(or ethyl)cyclopropane derivatives wherein the carboxylate group contains an amine or quaternized amine moiety.

2-Vinyl- and 2-ethylcyclopropane monocarboxylates as plant growth

2,4,5-Trisubstituted-2,3-dihydrofurans useful for fungicidal applications are provided herein. The 2,3-dihydrofuran compounds correspond to the general formula ##STR1## where R is an ethyl or vinyl group, R.sub.1 is a C.sub.1-10 hydrocarbon radical and X is a nitrile, amide or sulfonyl group. The compounds of this invention are effective fungicides for the treatment of seeds and also find use in other agricultural fungicidal applications.

2,3-Dihydrofurans useful as fungicides

Novel 2-vinyl-1-ketocyclopropane-1-carboxylates and 2-ethyl-1-ketocyclopropane-1-carboxylates useful as fragrance chemicals, pesticides, herbicides and chemical intermediates are provided. The invention also relates to a process for augmenting or enhancing the fragrance qualities of a formulation by the addition thereto of certain 2-vinyl-1-ketocyclopropane-1-carboxylates.

Process for augmenting or enhancing the aroma of a fragrance by adding a

2,4,5-Trisubstituted-2,3-dihydrofurans useful as fragrance compounds are provided herein. The compounds of this invention correspond to the general formula ##STR1## wherein R is an ethyl or vinyl group, R.sub.1 is an alkyl group having from 1 to 4 carbon atoms and R.sub.2 is a hydrocarbon radical having from 3 to 10 carbon atoms. The 2,3-dihydrofuran compounds of the present invention are useful components in the preparation and formulation of fragranced cosmetic and toiletry products.

Dihydrofurans

A process is provided wherein cyclopropyl ketones are readily isomerized to 2,3-dihydrofurans. The process involves the thermal rearrangement of 1,1-disubstituted-2-alkylcyclopropanes or 1,1-disubstituted-2-alkenylcyclopropanes, wherein one of the substituents in the 1-position is an acyl group, to 2,4,5-trisubstituted-2,3-dihydrofurans employing an onium compound as the catalyst.

Process for the isomerization of cyclopropyl ketones to 2,3-dihydrofurans

Novel 2-vinyl- and 2-ethyl-cyclopropyl sulfones are provided. In addition to the ethyl or vinyl group at the 2-position of the ring, the compounds of this invention are disubstituted at the 1-position with a sulfonyl group and an acyl, nitrile or nitrile-derived radical. The sulfones of this invention are useful chemical intermediates from which a wide variety of pesticidal, herbicidal or biologically active compounds can be prepared and are useful monomers for anionic or radical polymerizations.

Substituted-cyclopropyl sulfones

2-Vinyl- and 2-ethylcyclopropane monocarboxylates

2-Vinyl- and 2-ethylcyclopropanes having an aryl group and a nitrogen-containing radical substituted at the 1-position on the ring are provided. The novel 1,1-disubstituted 2-vinylcyclopropane and 2-ethylcyclopropane compounds of this invention have utility in herbicidal applications and are useful reactants. The 2-vinylcyclopropane derivatives are useful monomers for anionic and radical polymerizations.

Growing community of inventors

Fairfield, OH, United States of America

Richard G Fayter