The Dow Chemical Company

Dow Global Technolgoies LLC

P J Thomas

R Garth Pews

David A Babb

Paul C Vosejpka

Zenon Lysenko

Jerry E White

John Michael Maher

Clark H Cummins

Aaron W Sanders

George J Frycek

Alan K Schrock

Christopher P Christenson

Jozef Bicerano

Robert A Kirchhoff

Marvin L Dettloff

Kenneth A Burdett

Wei-Jun Peng

Richard Dicran Varjian

Bob R Maughon

Christopher W Derstine

Donald L Morrison

Ray H Jouett

Integrated processes of preparing industrial chemicals starting from seed oil feedstock compositions containing one or more unsaturated fatty acids or unsaturated fatty acid esters, which are essentially free of metathesis catalyst poisons, particularly hydroperoxides; metathesis of the feedstock composition with a lower olefin, such as ethylene, to form a reduced chain olefin, preferably, a reduced chain &#x3b1;-olefin, and a reduced chain unsaturated acid or ester, preferably, a reduced chain &#x3b1;,&#x3c9;-unsaturated acid or ester. The reduced chain unsaturated acid or ester may be (trans)esterified to form a polyester polyolefin, which may be epoxidized to form a polyester polyepoxide. The reduced chain unsaturated acid or ester may be hydroformylated with reduction to produce an &#x3b1;,&#x3c9;-hydroxy acid or &#x3b1;,&#x3c9;-hydroxy ester, which may be (trans)esterified with a polyol to form an &#x3b1;,&#x3c9;-polyester polyol. Alternatively, the reduced chain unsaturated acid or ester may be hydroformylated with reductive amination to produce an &#x3b1;,&#x3c9;-amino acid or &#x3b1;,&#x3c9;-amino ester, which may be (trans)esterified to form an &#x3b1;,&#x3c9;-polyester polyamine.

Integrated chemical processes for industrial utilization of seed oils

A 2,3-dihalopropanol is made by reacting 2,3-dihalopropanal with molecular hydrogen in the presence of a transition metal-containing catalyst, under conditions such that 2,3-dihalopropanol is formed. The reaction is particularly useful, for example, as Step (3) in a process to make epihalohydrin which may be generally prepared by:

Process for making 2,3-dihalopropanols

A 2,3-dihalopropanol is made by reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of a transition metal-containing catalyst, under conditions such that 2,3-dihalopropanol is formed. The reaction is particularly useful as Step (3) in a process to make epihalohydrin by:

Process to make 2,3-dihalopropanols

The invention is a bis-BCB compound of the structure: ##STR1## a method for making same and polymers made therefrom. The novel compounds of this invention are useful in preparing polymers that can form thin film coatings for multichip midules (MCMs) and integrated circuits (ICs). These compounds can be isolated as liquids at room temperature, and can form polymers that are hydrophobic and have low dielectrical and dissipative properties.

Bisbenzocyclobutene compounds with hydrophobic substituents, a method

A process for preparing a substituted or unsubstituted 3- or 4-hydroxyalkylbenzocyclobutene compound comprises reducing a corresponding 3- or 4-formyl or ketobenzocyclobutene compound with a hydride at a temperature below that at which dimerization or oligomerization of the formyl- or ketobenzocycloutene compound or the thus-produced hydroxyalkylbenzocyclobutene compound is a significant side reaction, for a time sufficient to convert the formyl- or ketobenzocyclobutene compound to the hydroxyalkylbenzocyclobutene compound. In a two-step process, formylbenzocyclobutenes are prepared from bromobenzocyclobutenes in 90% yield or from benzocyclobutenes in a 70% yield, and then converted to hydroxymethylbenzocyclobutenes for an overall yield of about 85% from a bromobenzocyclobutene or of about 65% from a benzocyclobutene. In a two-step process, ketobenzocyclobutenes from bromobenzocyclobutene Grignard reagents and an N-alkanoyl- or N-aroyl-2-methylaziridine are converted to hydroxyalkylbenzocyclobutenes in high yields.

Process for preparing hydroxyalkylbenzocyclobutenes

A process for preparing carboxylic acid esters of of the formula

Process for preparing ester of hydroxymethylbenzocyclobutenes

An improved process for the nitration of a substituted or unsubstituted benzocyclobutene compound in a reaction mixture comprising a nitrating agent, an unhalogenated carboxylic acid anhydride, clay and a solvent to produce a corresponding nitrobenzocyclobutene compound, is that wherein:

Process for nitrating benzocyclobutene compounds

Hydroxy arylcyclobutenes are prepared by the Baeyer-Villiger oxidation of arylcyclobutene aldehydes with permonophosphoric acid.

Preparation of hydroxy arylcyclobutenes

3-chloromethylbenzocyclobutene is prepared by reacting benzocyclobutene with chloromethyl methyl ether in the presence of stannic chloride at a temperature of about -120.degree. C. to about -40.degree. C. and neutralizing the resulting reaction mixture comprising 3-chloromethylbenzocyclobutene at a temperature of about -80.degree. C. to about -70.degree. C.

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Midland, MI, United States of America

P J Thomas