Patents by Inventor Pieter A. Verbrugge
Pieter A. Verbrugge has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5189197Abstract: The invention provides a process for the preparation of N-benzoylcarbamates of general formula ##STR1## wherein R.sup.1 represents a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group or a trifluoromethyl group, R.sup.2 represents a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group or a trifluoromethyl group, R.sup.3 represents a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, and R represents a C.sub.1-8 alkyl group optionally substituted by one or more halogen atoms or a phenyl group optionally substituted by one or more substituents selected from halogen atoms and methyl groups, characterized by reacting an alkali metal salt of a benzamide of general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: February 27, 1990Date of Patent: February 23, 1993Assignee: Shell Internationale Research Maatschappij B.V.Inventors: Pieter A. Verbrugge, Jannetje De Waal
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Patent number: 5155135Abstract: This invention provides benzamide compounds of general formula ##STR1## wherein each of A and B independently represents a hydrogen or halogen atom, X represents an oxygen or a sulphur atom, n is 0, 1, 2, 3 or 4, each Z moiety independently represents a halogen atom or a C.sub.1-6 alkyl group, and Y represents a C.sub.1-6 haloalkyl group, a C.sub.1-6 haloalkoxy group, a group of formula ##STR2## wherein P is 0, 1 or 2, each Z' moiety independently represents a halogen atom or a C.sub.1-6 alkyl group, Y' represents a C.sub.1-6 haloalkyl, C.sub.1-6 haloalkoxy, nitro or cyano group and Q represents N or C-H, or, when n is 2 or 3, Y may also be a halogen atom; processes for their preparation; and their use as pesticides.Type: GrantFiled: December 6, 1989Date of Patent: October 13, 1992Assignee: Shell Internationale Research Maatschappij, B.V.Inventors: Martin Anderson, Antony G. Brinnand, Pieter A. Verbrugge
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Patent number: 4855452Abstract: Process for the preparation of a compound of formula or a salt thereof ##STR1## wherein R.sub.1 represents a hydrogen atom or a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)-- wherein R.sub.2 represents a phenyl, tolyl or C.sub.1-4 alkyl group and R.sub.3 represents a hydrogen atom or a phenyl or C.sub.1-4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula ##STR2## wherein R.sub.4 represents a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)-- and R.sub.5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R.sub.5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and, if desired to produce a compound in which R.sub.1 represents a hydrogen atom, by deprotection of the N-atom.Type: GrantFiled: June 9, 1988Date of Patent: August 8, 1989Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Jannetje de Waal, David W. Sopher
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Patent number: 4812581Abstract: Preparation of azetidine-3-carboxylic acid or a salt thereof from N-benzylazetidine-3-carboxylic acid or a salt thereof by catalytically hydrogenating the N-benzylazetidine-3-carboxylic compound in the presence of water, formate ions, and ammonium and/or alkylammonium ions. Novel ammonium and alkylammonium salts are claimed.Type: GrantFiled: October 28, 1987Date of Patent: March 14, 1989Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Jannetje de Waal
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Patent number: 4778577Abstract: Process for the preparation of a compound of formula or a salt thereof ##STR1## wherein R.sub.1 represents a hydrogen atom or a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)--wherein R.sub.2 represents a phenyl, tolyl or C.sub.1-4 alkyl group and R.sub.3 represents a hydrogen atom or a phenyl of C.sub.1-4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula ##STR2## wherein R.sub.4 represents a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)--and R.sub.5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R.sub.5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and, if desired to produce a compound in which R.sub.1 represents a hydrogen atom, by deprotection of the N-atom.Type: GrantFiled: April 16, 1986Date of Patent: October 18, 1988Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Jannetje De Waal, David W. Sopher
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Patent number: 4554109Abstract: Process for the preparation of esters of 1,5-dimethyl bicyclo [3.2.1] octan-8-ol and/or derivatives thereof by reacting 1,5-dimethyl-1,5-cyclooctadiene with an inorganic polybasic acid.Type: GrantFiled: December 15, 1983Date of Patent: November 19, 1985Assignee: Shell Oil CompanyInventor: Pieter A. Verbrugge
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Patent number: 4421935Abstract: Process for the preparation of Diels-Alder type adducts by reacting a compound with formula ##STR1## or the corresponding hydrated derivative, wherein R.sup.1, R.sup.2, and R.sup.4 are H or lower alkyl, R.sup.3 is lower alkyl, X is O,S, (O--CR.sup.5 R.sup.6 R.sup.7).sub.2 or ##STR2## wherein R.sup.5, R.sup.6 and R.sup.7 an H or lower alkyl, n is 2-5 and Y is H, alkyl or alkenyl or Y and R.sup.2 together form an alkylene group which may contain one or more substituents, with a cyclopentadiene and/or an oligomer thereof in the presence of an aqueous solution of a strong proton donor having a conjugate with a low nucleophilicity.Type: GrantFiled: May 3, 1982Date of Patent: December 20, 1983Assignee: Shell Oil CompanyInventor: Pieter A. Verbrugge
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Patent number: 4388247Abstract: When the reaction of aldehydes with alkali metal trihaloacetates is carried out in the presence of a highly polar aprotic solvent (DMF, DMSO), novel organic alkali metal carbonates, which are precursors of pyrethroid insecticides, are formed in high yields and at a high rate. Novel sulfonates and dihalophosphites, derived from these carbonates have also been claimed.Type: GrantFiled: August 25, 1980Date of Patent: June 14, 1983Assignee: Shell Oil CompanyInventors: Petrus A. Kramer, Pieter A. Verbrugge
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Patent number: 4307243Abstract: Conversion of esters (R.sup.1)(R.sup.2)C(C Hal.sub.3)OX, X being-P Hal.sub.2, --C(O)OR.sup.3 or ##STR1## R.sup.1, R.sup.3 and R.sup.4 being optionally substituted hydrocarbyl groups and R.sup.2 methyl or hydrogen, with zinc in acetic acid gives a very high yield of a dihalovinyl compound (R.sup.1)(R.sup.2)C.dbd.C Hal.sub.2, e.g., of the ethyl ester of the parent acid of pyrethroid insecticides.Type: GrantFiled: March 25, 1980Date of Patent: December 22, 1981Assignee: Shell Oil CompanyInventors: Petrus A. Kramer, Pieter A. Verbrugge
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Patent number: 4305890Abstract: When the reaction of aldehydes with alkali metal trihaloacetates is carried out in the presence of a highly polar aprotic solvent (DMF, DMSO), novel organic alkali metal carbonates, which are precursors of pyrethroid insecticides, are formed in high yields and at a high rate. Novel sulfonates and dihalophosphites, derived from these carbonates have also been claimed.Type: GrantFiled: August 25, 1980Date of Patent: December 15, 1981Assignee: Shell Oil CompanyInventors: Petrus A. Kramer, Pieter A. Verbrugge
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Patent number: 4298756Abstract: Preparation of novel alkyl 2,2-dihalovinylcyclopropylacetates (intermediates in the preparation of insecticides) by reaction of a phosphine with a compound generating a dihalocarbene and reaction of the product resulting therefrom with an alkyl formylcyclopropylacetate, both reactions being carried out in a solvent.Type: GrantFiled: September 24, 1979Date of Patent: November 3, 1981Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer
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Patent number: 4294765Abstract: Isolation of cis acids of the formula ##STR1## wherein each of the groups X.sup.1 and X.sup.2 represents a fluorine, chlorine or bromine atom or a hydrocarbyl group, from a mixture of cis and trans acids of this formula, by idolactonization, forming novel cis-lactones of the formula ##STR2## isolation of these cis-lactones and reduction thereof to the said cis acids.The process may be used for the isolation of cis precursors to insecticides from mixtures with their trans isomers.Type: GrantFiled: October 23, 1980Date of Patent: October 13, 1981Assignee: Shell Oil CompanyInventors: Petrus A. Kramer, Pieter A. Verbrugge
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Patent number: 4285882Abstract: When the reaction of aldehydes with alkali metal trihaloacetates is carried out in the presence of a highly polar aprotic solvent (DMF, DMSO), novel organic alkali metal carbonates, which are precursors of pyrethroid insecticides, are formed in high yields and at a high rate. Novel sulfonates and dihalophosphites, derived from these carbonates have also been claimed.Type: GrantFiled: March 25, 1980Date of Patent: August 25, 1981Assignee: Shell Oil CompanyInventors: Petrus A. Kramer, Pieter A. Verbrugge
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Patent number: 4247711Abstract: 2-Formyl-3,3-dimethylcyclopropylacetic acid is prepared by ozonolysis of 3-acetyl-6,6-dimethylbicyclo[3.1.0]-2-hexene followed by reductive cleavage of the ozonolysis product thus formed. The 3-acetyl-6,6-dimethylbicyclo[3.1.0]-2-hexene is prepared by contacting 2-(2-acetyl-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde with a base in the presence of a solvent.Type: GrantFiled: April 24, 1979Date of Patent: January 27, 1981Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer
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Patent number: 4242279Abstract: The invention relates to 2-(2,2-dihalovinyl)-3,3-dimethylcyclopropylacetones which are intermediates for the preparation of pyrethroids which have good insecticidal properties.Type: GrantFiled: September 24, 1979Date of Patent: December 30, 1980Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer
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Patent number: 4239707Abstract: Novel compounds of general formula (I) ##STR1## wherein X represents a F, Cl, Br, I or CN are of interest as heat stable ligands for catalytic systems. They can be prepared in good yields from 1,5-dimethyl-1,5-cyclooctadiene as well as from the corresponding bicyclic alcohol wherein X is OH.Type: GrantFiled: December 21, 1979Date of Patent: December 16, 1980Assignee: Shell Oil CompanyInventors: Albertus J. Mulder, Pieter A. Verbrugge
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Patent number: 4230891Abstract: New 2-(2,2-dihalovinyl)-3,3-dimethylcyclopropane derivatives of the formula ##STR1## wherein each Hal is a halogen atom and R is dimethoxyethyl, 2-acetyl-3-oxobutyl, 2-methoxycarbonylpropyl or 2-acetyl-2-hydroxy-3-oxobutyl, are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.Type: GrantFiled: December 5, 1978Date of Patent: October 28, 1980Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer, Johannes Van Berkel, Hendrik C. Kelderman
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Patent number: 4219504Abstract: A process for the preparation of an aldehyde or a ketone by ozonolysis of an ethylenically unsaturated compound in the presence of an anti-oxidant followed by reductive cleavage of the ozonolysis product.Type: GrantFiled: February 23, 1979Date of Patent: August 26, 1980Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer
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Patent number: 4180520Abstract: .alpha.,.beta.-Unsaturated nitriles are prepared from carbonyl compounds and then reduced by reaction with an alkanol and magnesium in the presence of an ammonium salt.Type: GrantFiled: September 5, 1978Date of Patent: December 25, 1979Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer
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Patent number: 4132728Abstract: .alpha.,.beta.-Unsaturated nitriles are prepared from carbonyl compounds and then reduced by reaction with an alkanol and magnesium in the presence of an ammonium salt.Type: GrantFiled: June 13, 1977Date of Patent: January 2, 1979Assignee: Shell Oil CompanyInventors: Pieter A. Verbrugge, Petrus A. Kramer