The Standard Oil Company

Other

Robert A Dubbert

Mark C Cesa

James D Burrington

John Raymond Budge

Thomas G Attig

Robert K Grasselli

Dev D Suresh

Michael J Seely

Maria Strada Friedrich

Mark R Bruce

Tai C Yang

Maleic acid and/or other hydrogenatable precursors are hydrogenated in the presence of a noble metal catalyst to 1,4-butanediol. The production and yields of 1,4-butanediol are enhanced by the addition of iron to the hydrogenatable precursor feed.

Process for the hydrogenation of maleic acid to 1,4-butanediol

An improved catalyst for the hydrogenation of maleic acid, maleic anhydride or other hydrogenatable precursor to 1,4-butanediol and tetrahydrofuran has been discovered. This hydrogenation catalyst comprises palladium, silver, rhenium and at least one of iron, aluminum, cobalt and mixtures thereof, all on a carbon support.

Catalysts for the hydrogenation of maleic acid to 1,4-butanediol

Disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) separating the diastereomers by conventional physical means and (3) hydrolyzing at least one of said separated diastereomers to make at least the .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid. Also disclosed is a process for making an .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid which comprises (1) hydrocarboxylating an enol acylate, the enol portion of which has a chiral C atom that is essentially all L or all D, with CO and water or an organic hydroxyl compound, thereby producing a reaction mixture containing diastereomeric .alpha.-acyloxy acids or esters having two chiral centers and having essentially no enantiomeric pairs, (2) hydrolyzing the product of (1) to make a diastereomeric mixture containing .alpha.-hydroxy acids, and (3) separating by conventional physical means from the product of (2) at least one .alpha.-hydroxy acid which is essentially all L or all D with respect to the chiral C atom bonded to the carboxy group of said acid.

Making optically active alpha-hydroxy acids or precursors

A process of producing hydrogen cyanide from crude acetonitrile comprising contacting the crude acetonitrile with an ammoxidation catalyst at an elevated temperature in the presence of an oxygen containing gas and ammonia. Preferably, the process is performed in the absence of propylene.

HCN by catalytic ammoxidation of crude acetonitrile

Disclosed is a process for making ethylamines by the hydrogenation in a reaction zone of acetonitrile contained in a basic aqueous solution which also contains HCN, which comprises continuously passing hydrogen gas in contact with a flowing stream containing acetonitrile, water and HCN, which stream is in contact with a solid hydrogenation catalyst, wherein the hydrogen contact time is in the range from 0.5 seconds to 20 minutes and the molar ratio of H.sub.2 to acetonitrile charged to said reaction zone is in the range 2-200:1.

Synthesis of ethylamines

1,3-butadienes are catalytically hydrocarbamylated to make 3-pentenamides.

3-pentenamides from 1,3-butadienes

In the process of hydrocarboxylating an .alpha.-enamide with CO and H.sub.2 O or an organic hydroxyl compound to produce an N-acyl-.alpha.-amino acid or ester, respectively, the improvement comprising using as the .alpha.-enamide reactant, an .alpha.-enamide which has a chiral center that is essentially all L or D, thereby producing a reaction mixture containing diastereomeric N-acyl-.alpha.-amino acids or esters having two chiral centers, said mixture having essentially no enantiomeric pairs.

Process for making an optically active mixture of an N-acyl-amino acid

A process for making a diamide of the formula ##STR1## by reacting a monoamide compound of the formula ##STR2## with CO and an amine or ammonia of the formula R.sub.7 R.sub.8 NH in the liquid phase under essentially anhydrous conditions at a temperature in the range from 120.degree. to 210.degree. C., where each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 is selected independently from H and a C.sub.1 to C.sub.12 hydrocarbyl containing no ethylenic or acetylenic unsaturation.

1,6-hexanediamides from 3-pentenamides

In the process of hydrocarboxylating an enol acylate with CO and an organic hydroxyl compound to produce an .alpha.-acyloxy acid ester, the improvement comprising using as the organic hydroxyl compound reactant, an organic hydroxyl compound which has a chiral center that is essentially all L or D, thereby producing a reaction mixture having essentially no enantiomeric pairs and containing diastereomeric .alpha.-acyloxy acid esters having two chiral centers.

Method of making a diastereomeric mixture containing two diastereomeric

In the process of hydrocarboxylating an .alpha.-enamide with CO and an organic hydroxyl compound to produce a N-acyl-.alpha.-amino acid ester, the improvement comprising using as the organic hydroxyl compound reactant, an organic hydroxyl compound which has a chiral center that is essentially all L or D, thereby producing a reaction mixture having essentially no enantiomeric pairs and containing diastereomeric N-acyl-.alpha.-amino acid esters having two chiral centers.

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Solon, OH, United States of America

Robert A Dubbert