Shell Oil Comapny

Shell Development Company

David M Singleton

Brendan Dermot Murray

Louis N Kravetz

Zaida Diaz

Herbert E Fried

Howard L Fong

Paul Benjerman Himelfarb

Raul A Pabon, Jr

Richard Edward Robertson

Brendan Dermont Murray

There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and containing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching at the Cposition relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the [001] view ranging from greater than 4.2 &#x212b; and less than 7 &#x212b;, but allows one to skeletally isomerize the olefin to produce a variety of branches, while retaining ready biodegradability and good cold water detergency.

Highly branched primary alcohol compositions, and biodegradable detergents made therefrom

There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and containing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching at the Cposition relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the [001] view ranging from greater than 4.2 &#x212b; and less than 7 &#x212b;. but allows one to skeletally isomerize the olefin to produce a variety of branches, while retaining ready biodegradability and good cold water detergency.

There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and containing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching at the Cposition relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the [001] view ranging from greater than 4.2 &#x212b; and less than 7 &#x212b; but allows one to skeletally isomerize the olefin to produce a variety of branches, while retaining ready biodegradability and good cold water detergency.

A process for making a selectively branched alcohol composition contacting a lower olefin feed comprising linear olefins having at least 3 carbon atoms and a concentration of phosphorous-containing compounds with a sorbent comprising a metal or metal oxide on a support, thereby substantially reducing the concentration of phosphorous-containing compounds and producing a purified lower olefin feed. The purified lower olefin feed is skeletally isomerized and then treated to selectively hydrogenate dienes before hydroformylation to produce selectively branched alcohols.

Phosphorous removal and diene removal, when using diene sensitive catalyst, during conversion of olefins to branched primary alcohols

The invention pertains to a process of removing phosphorous-containing impurities and preferably also dienes, from an olefin stream using a sorbent selected from the group consisting of an acidic ion exchange resin, an acidic zeolite, an acidic alumina, a neutral alumina, and an activated carbon. The olefin stream preferably comprises primarily olefins having at least 6 carbon atoms.

Removal of phosphorus-containing impurities from an olefin feedstock

The invention pertains to a process of making selectively branched alcohol compositions by oligomerizing a lower olefin feed. The lower olefin feed preferably comprises linear olefins having at least three carbon atoms.

Process for preparation of selectively branched detergent products

There is provided an alcohol composition obtained by dimerizing an olefin feed comprising C,-C,linear olefins to obtain C,-C,olefins, followed by conversion to alcohols, such as by hydroformylation. The composition has an average number of branches ranging from 0.9 to 2.0 per molecule. The linear olefin feed preferably comprises at least 85% of C,-C,-olefins. The primary alcohol compositions are then converted to anionic or nonionic surfactants, preferably sulfated or oxyalkylated or both. The sulfated compositions are biodegradable and possess good cold water detergency. The process for making the dimerized primary alcohol comprises dimerizing, in the presence of a homogeneous dimerization catalyst under dimerization conditions, an olefin feed comprising C,-C,olefins and preferably at least 85 weight % of linear olefins based on the weight of the olefin feed, to obtain a C,-C,; optionally double bond isomerizing said C,-C,olefins; and converting the C,-C,olefins to alcohols, preferably through hydroformylation. The process is preferably a one-step dimerization. The homogenous catalyst comprises a mixture of a nickel carboxylate or a nickel chelate, with an alkyl aluminum halide or an alkyl aluminum alkoxide.

Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency

There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and contianing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching at the C.sub.3 position relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the [001] view ranging from greater than 4.2 .ANG. and less than 7 .ANG.. but allows one to skeletally isomerize the olefin to produce a variety of branches, while retaining ready biodegradability and good cold water detergency.

Highly branched primary alcohol compositions and biodegradable

There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and contianing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching it the C.sub.3 position relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the �001! view ranging from greater than 4.2 .ANG. and less than 7 .ANG., but allows one to skeletally isomerize the olefin to produce a variety of branches, while retaining ready biodegradability and good cold water detergency.

Highly branched primary alcohol compositions, and biodegradable

There is provided an alcohol composition obtained by dimerizing an olefin feed comprising C.sub.6 -C.sub.10 linear olefins to obtain C.sub.12 -C.sub.20 olefins, followed by conversion to alcohols, such as by hydroformylation. The composition has an average number of branches ranging from 0.9 to 2.0 per molecule. The linear olefin feed preferably comprises at least 85% of C.sub.6 -C.sub.8 -olefins. The primary alcohol compositions are then converted to anionic or nonionic surfactants, preferably sulfated or oxyalkylated or both. The sulfated compositions are biodegradable and possess good cold water detergency. The process for making the dimerized primary alcohol comprises dimerizing, in the presence of a homogeneous dimerization catalyst under dimerization conditions, an olefin feed comprising C.sub.6 -C.sub.10 olefins and preferably at least 85 weight % of linear olefins based on the weight of the olefin feed, to obtain a C.sub.12 -C.sub.20 ; optionally double bond isomerizing said C.sub.12 -C.sub.20 olefins; and converting the C.sub.12 -C.sub.20 olefins to alcohols, preferably through hydroformylation. The process is preferably a one-step dimerization. The homogenous catalyst comprises a mixture of a nickel carboxylate or a nickel chelate, with an alkyl aluminum halide or an alkyl aluminum alkoxide.

Dimerized alcohol compositions and biodegradible surfactants made

A process for preparing an alkoxyalkanoic acid by reacting the corresponding alkoxyalkanol with a resin-supported stable free radical nitroxide in the presence of a NO.sub.x -generating compound and, optionally, an oxidant and/or a solvent at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the alkoxyalkanoic acid.

Preparation of alkoxyalkanoic acids

A process for preparing an alkoxyalkanoic acid by reacting the corresponding alkoxyalkanol with a resin-supported stable free radical nitroxide in the presence of a chlorine-containing oxidant and a solvent at a temperature in the range of from about 0.degree. C. to about 35.degree. C. and thereafter separating out the alkoxyalkanoic acid.

This invention relates to a process for the two-stage hydrogenation of methyl esters which comprises: a) contacting and reacting one or more detergent range methyl esters with hydrogen under predominantly liquid phase hydrogenation conditions at a temperature of less than about 230.degree. C., in the presence of a catalyst comprising a copper compound, a zinc compound, and at least one compound selected from the group consisting of aluminum, zirconium, magnesium, a rare earth and mixtures thereof, to produce an alcohol product and a wax ester product, and b) contacting and reacting the wax ester product from step a) with hydrogen under predominantly liquid phase hydrogenation conditions at a temperature greater than about 220.degree. C. in the presence of a catalyst comprising a copper compound, a zinc compound, and at least one compound selected from the group consisting of aluminum, zirconium, magnesium, a rare earth and mixtures thereof, to produce an alcohol product.

Process for the two-stage hydrogenation of methyl esters

This invention relates to a process for the direct hydrogenation of methyl esters which comprises contacting and reacting one or more detergent range methyl esters with hydrogen under predominantly liquid phase hydrogenation conditions in the presence of a catalyst comprising a copper compound, a zinc compound, and at least one compound selected from the group consisting of aluminum, zirconium, magnesium, a rare earth and mixtures thereof.

Process for the direct hydrogenation of methyl esters

This invention relates to a process for the direct hydrogenation of triglycerides which comprises contacting and reacting one or more triglyceride with hydrogen under liquid phase hydrogenation conditions in the presence of a catalyst comprising a copper compound, a zinc compound, at least one rare earth compound, and, optionally, a compound selected from the group consisting of aluminum, zirconium, magnesium, and mixtures thereof.

Growing community of inventors

Houston, TX, United States of America

David M Singleton