Jeffrey S Robbins

US Patent:

49564870, Sep 11, 1990

Filed:

Dec 12, 1988

Appl. No.:

7/283345

Inventors:

Jeffrey D. Robbins - Berkeley CA
Richard D. Gless - Oakland CA

Assignee:

ICI Americas Inc. - Wilmington DE

International Classification:

C07F 940

US Classification:

558 98

Abstract:

Thiophosphonate compounds having the formula ##STR1## in which R is alkyl, haloalkyl or aryl; X is chloro or SR. sub. 2 ; R. sub. 1 is alkyl or aryl; and when X is SR. sub. 2 then R. sub. 2 is a group identical to R. sub. 1, or R. sub. 1 and R. sub. 2 taken together form an optionally alkyl-substituted polymethylene group, are prepared by reaction of a thiophosphonodichloride with a mercaptan in the presence of a catalytic amount of a quaternary ammonium or phosphonium salt, a tertiary amine or hydrohalide thereof or an alkali metal halide combined with a Crown ether, in the substantial absence of a base.

US Patent:

41170431, Sep 26, 1978

Filed:

Sep 26, 1977

Appl. No.:

5/836322

Inventors:

Llewellyn W. Fancher - Orinda CA
Jeffrey D. Robbins - Berkeley CA

Assignee:

Stauffer Chemical Company - Westport CT

International Classification:

C07F 9165
C07F 932
C07F 940

US Classification:

260938

Abstract:

N-(beta-diorganodithiophosphorylethyl) aryl and alkyl sulfonamides are prepared by a process comprising reacting a compound having the formula R. sup. 1 SO. sub. 2 X with 2-aminoethyl hydrogen sulfate and an aqueous solution of M. sup. 1 OH, and reacting the resulting product with a compound having the formula ##STR1## In the above description, R. sup. 1 is selected from the group consisting of C. sub. 1 -C. sub. 10 alkyl, halo-substituted C. sub. 1 -C. sub. 10 alkyl, phenyl, halo-substituted phenyl, nitro-substituted phenyl, and naphthyl; R. sup. 2 and R. sup. 3 are independently selected from the group consisting of C. sub. 1 -C. sub. 10 alkyl and C. sub. 1 -C. sub. 10 alkoxy; X is selected from the group consisting of chloride, bromide, and iodide; and M. sup. 1 and M. sup. 2 are independently selected from the group consisting of lithium, sodium, potassium, ammonium, and tri-substituted ammonium wherein the substituents are independently C. sub. 1 -C. sub. 10 alkyl.

US Patent:

44288883, Jan 31, 1984

Filed:

Aug 16, 1982

Appl. No.:

6/408322

Inventors:

Jeffrey D. Robbins - Berkeley CA

Assignee:

Stauffer Chemical Company - Westport CT

International Classification:

C07F 938

US Classification:

2605025F

Abstract:

Disclosed is a method for the preparation of N-phosphonomethylglycine which comprises the steps of (1) reacting 1,3,5-tris(alkoxy- or aryloxy-substituted carbonylmethyl) hexahydro-s-triazine, with a substituted phosphorus compound having the formula PXYZ wherein X is a halogen, Y and Z are independently selected from the group consisting of halogen, alkoxy having from 1 to 10 carbon atoms, and aryloxy, in the presence of a protic acid and a low molecular weight carboxylic acid; (2) heating said reactants to a temperature ranging from about 10. degree. to about 25. degree. C. for a sufficient period of time to cause the formation of an N-phosphonomethylglycine ester,; and (3) hydrolyzing said phosphonomethylglycine ester to N-phosphonomethylglycine.

US Patent:

44406959, Apr 3, 1984

Filed:

Aug 12, 1982

Appl. No.:

6/407366

Inventors:

Jeffrey D. Robbins - Berkeley CA

Assignee:

Stauffer Chemical Company - Westport CT

International Classification:

C07F 938

US Classification:

2605025F

Abstract:

A method for the production of N-phosphonomethylglycine which comprises reacting N,N-bis(phosphonomethyl)glycine having the formula ##STR1## with glycine in the presence of a hydrogen ion donor and of water, and at a sufficient temperature and at a sufficient pressure to cause the reaction to go to completion.

US Patent:

44155034, Nov 15, 1983

Filed:

Sep 28, 1982

Appl. No.:

6/424941

Inventors:

Jeffrey D. Robbins - Berkeley CA

Assignee:

Stauffer Chemical Company - Westport CT

International Classification:

C07F 938

US Classification:

2605025F

Abstract:

Disclosed is a method for the preparation of N-phosphonomethylglycine which comprises the steps of (a) reacting 1,3,5-tri-(substituted methyl) hexahydro-s-triazine, a compound of the formula ##STR1## wherein R, R. sub. 1 and R. sub. 2 are the same or different and are selected from the group consisting of cyano, alkoxycarbonyl wherein the alkyl group ranges from 2 to 18 carbon atoms, and aryloxycarbonyl wherein the aryl group ranges from 6 to 12 carbon atoms, with a substituted phosphorus compound having the formula PXYZ wherein X is a halogen, Y and Z are each independently selected from the group consisting of halogen, alkoxy having from 1 to 10 carbon atoms and aryloxy, in the presence of a low molecular weight carboxylic acid solvent and a protic acid; (b) treating the reaction mixture with water; (c) removing said solvent and hydrolyzing the residue with aqueous alkali to generate a salt of N-phosphonomethylglycine; and (d) neutralizing said salt with an acid to produce the end product, N-phosphonomethylglycine.

US Patent:

45782245, Mar 25, 1986

Filed:

Jun 20, 1984

Appl. No.:

6/622427

Inventors:

Arthur C. Bayer - Yorktown Heights NY
Jeffrey D. Robbins - Berkeley CA
Donald J. Bowler - Concord CA

Assignee:

Stauffer Chemical Company - Westport CT

International Classification:

C07F 938

US Classification:

2605025F

Abstract:

Disclosed is a method for the preparation of salts of N-phosphonomethylglycine which comprises the steps of (a) reacting hydantoin or a 3-substituted hydantoin, a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl having from 1 to 10 carbon atoms, aryl having from 6 to 12 carbon atoms, alkylcarbonyl wherein the alkyl group has from 1 to 10 carbon atoms, and arylcarbonyl wherein the aryl group has from 6 to 12 carbon atoms, with paraformaldehyde in the presence of a low molecular weight carboxylic acid at a temperature and for a sufficient period of time to produce a mixture of intermediate products, including the 1-hydroxymethyl derivative of the starting hydantoin; (b) converting said 1-hydroxymethyl derivative to the 1-phosphonomethyl derivative by thereafter adding to the reaction mixture either (i) a substituted phosphorus compound selected from the group consisting of phosphorus trichloride, and phosphorus tribromide; or (ii) adding to the reaction mixture phosphorous acid and a anhydride selected from the group consisting acetic anhydride, propionic anhydride, butyric anhydride, or mixture thereof, and continuing said reaction at a temperature and for a sufficient period of time to cause completion of the reaction to form the 1-phosphonomethyl derivative; and (c) hydrolyzing the 1-phosphonomethylhydantoin product thus formed with a base selected from the group consisting of alkali metal or alkaline earth hydroxide, to produce a salt of N-phosphonomethylglycine.

US Patent:

44182104, Nov 29, 1983

Filed:

Dec 28, 1981

Appl. No.:

6/334705

Inventors:

Jeffrey D. Robbins - Berkeley CA

Assignee:

Stauffer Chemical Company - Westport CT

International Classification:

C07C15705

US Classification:

564 24

Abstract:

A novel process for preparing asymmetrical thioureas having the formula ##STR1## is disclosed, which comprises reacting RNH. sub. 2 with CS. sub. 2 in the presence of a base to produce RNHCS. sub. 2. crclbar. followed by reaction of the RNHCS. sub. 2. crclbar. with R. sub. 1 R. sub. 2 NH in the presence of a catalytic amount of a base to produce the desired product.

US Patent:

55547621, Sep 10, 1996

Filed:

May 15, 1995

Appl. No.:

8/442231

Inventors:

Jeffrey D. Robbins - Berkeley CA

Assignee:

Zeneca Limited - London

International Classification:

C07D23340
C07D23372

US Classification:

5483141

Abstract:

This invention relates to method for the preparation of 1,1'-methane-bis(hydantoin). 1,1'-methane-bis(hydantoin) is an intermediate in the preparation of N-(phosphonomethyl)glycine which is a well known herbicide and plant growth regulator.