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Huntsman Specialty Chemicals Corporation

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Shell Oil Corporation

Huntsman Ici Chemical LLC

Knifton, John F.

Duranleau, Roger G.

Nieh, Edward C.y.

John F Knifton

John R Sanderson

Jiang-Jen Lin

Edward T Marquis

Pei-Shing E Dai

Joseph Broun Powell

Paul Richard Weider

Kevin Dale Allen

Lynn Henry Slaugh

Talmadge Gail James

Neal J Grice

Roger G Duranleau

Timothy Williams

Prakasa R Anantaneni

Wei-Yang Su

Robert J Taylor, Jr

Robert L Zimmerman

John M Larkin

Edward E McEntire

Robert A Grigsby, Jr

William A Smith

Mark A Mueller

David C Alexander

Rei-Yu Judy Hwan

Melvin Ernest Stockton

Melvin Stockton

Rodney L Sung

Michael Cuscurida

Ernest L Yeakey

Juan Pedro Arhancet

Edward C Nieh

Brian L Benac

Yu-Hwa E Sheu

Bobby R Martin

Michael A Caggiano

Milton D Behrens

Susan D Unvert

Daniel John Janitor

Irving Schwager

George P Speranza

George A Smith

Robert M Suggitt

Terry L Renken

Mark E Taylor

Carter G Naylor

Steven H Vanderpool

Kathy B Sellstrom

Glenn Charles Komplin

Kyle Lee Preston

Richard F Love

Philip H Moss

Donald H Champion

Kenneth P Keating

Samir S Ashrawi

Edwin R Kerr

Walter H Brader, Jr

Raeda M Smadi

Laurence D Neff

David L Miller

Timothy L Lambert

Donald R Hollingsworth

Chau-Hwa Yang

Edward Lewis Nielsen

Michael Warren Peters

Roger G Dureanleau

Jonathan Lustri

Peishing E Dai

Pei S Dai

James Douglas Goshinska

Sanderson John R

P Eugene Dai

Edward Cy Nieh

Disclosed is a new catalyst composition comprising a bimetallic Co&#x2014;Fe catalyst, optionally complexed with a ligand selected from a N-heterocycle, phosphine, or porphorine ligand, that provides a lower cost alternative for the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, a catalyst containing cobalt carbonyl: iron carbonyl with no ligand, or a catalyst containing a cobalt carbonyl: octaethylporphine iron acetate provide moderate yields of 1,3-PDO in a one step synthesis under mild conditions.

One-step production of 1,3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst

The present invention is an improvement upon the process for the production of 1,3-propanediol wherein an aqueous solution of 3-hydroxy propanal is formed, catalyst, if any, used in said formation is removed from the solution, sodium hydroxide is added to the solution to neutralize any acid therein such that the pH is at least about 5, the neutralized aqueous solution is subjected to hydrogenation to produce a crude 1,3-propanediol mixture which is distilled to produce 1,3-propanediol, water, and reactive heavy components. The improvement on this process comprises replacing the sodium hydroxide with a hydroxide selected from the group consisting of ammonium hydroxide, alkali metal hydroxides other than sodium hydroxide, and alkaline earth metal hydroxides to reduce the viscosity of the reactive heavy components.

Reduction of the viscosity of reactive heavy byproducts during the production of 1,3-propanediol

This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.

Synthesis of aliphatic 1,3-diols utilizing reduced ligand concentration and water extraction

This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by use of the fluorine-containing mordenite in conjunction with a conventional solid LAB alkylation catalyst. The two catalysts may be used in a mixed catalyst bed or may be packed in series, with the relative proportions being adjusted to provide a desired 2-phenyl isomer content of in the final product.

Alkylbenzene detergents with high 2-isomer content

Disclosed is a new catalyst composition comprising a bimetallic Co&#x2014;Ru catalyst complexed with a N-heterocylcic ligand that is effective, economical, and provides improvements in oxidative stability in the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, cobalt-ruthenium-2,2'-bipyrimidine, 2,2&#x2032;-dipyridyl, or 2,4,6-tripridyl-s-triazine catalyst precursors in cyclic ether solvents, such as 1,3-dioxolane, 1,4-dioxolane, 1,4-dioxane, and 2-ethyl-2-methyl-1,3-dioxolane, provide good yields of 1,3-PDO in a one step synthesis.

One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a N-heterocyclic ligand

Disclosed is a novel class of modified ruthenium catalysts useful in the one step synthesis of 1,3-PDO comprising (a) a cobalt component comprising one or more non-ligated cobalt compounds; and (b) a ruthenium component comprising in major part a ruthenium carbonyl compound ligated with a phospholanoalkane ligand, solubilized in an ether solvent, that provides potential improvements in cost and performance in one step hydroformylation/hydrogenation. For example, cobalt-ruthenium-bidentate, bis(phospholano)alkane catalyst precursors in ether solvents provide good yields of 1,3-PDO in a one step synthesis.

One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand

Disclosed is a new catalyst composition comprising a bimetallic Co&mdash;Fe catalyst, optionally complexed with a ligand selected from a N-heterocycle, phosphine, or porphorine ligand, that provides a lower cost alternative for the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, a catalyst containing cobalt carbonyl: iron carbonyl with no ligand, or a catalyst containing a cobalt carbonyl: octaethylporphine iron acetate provide moderate yields of 1,3-PDO in a one step synthesis under mild conditions.

One-step production of 1, 3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst

One step process for preparing a 1,3-diol

Disclosed is a new catalyst composition comprising a bimetallic Co&mdash;Ru catalyst complexed with a N-heterocylcic ligand that is effective, economical, and provides improvements in oxidative stability in the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, cobalt-ruthenium-2,2&prime;-bipyrimidine, 2,2&prime;-dipyridyl, or 2,4,6-tripridyl-s-triazine catalyst precursors in cyclic ether solvents, such as 1,3-dioxolane, 1,4-dioxolane, 1,4-dioxane, and 2-ethyl-2-methyl-1,3-dioxolane, provide good yields of 1,3-PDO in a one step synthesis.

One-step production of 1, 3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand

Disclosed is a one step hydroformylation process for preparing a 1,3-diol, comprising the reaction of an oxirane with syngas at hydroformylation conditions in an inert solvent in the presence of a hydroformylation catalyst comprising a ruthenium (&plus;1)-phosphine bidentate: cobalt (&minus;1) complex, wherein the ligated metal is ruthenium, under conditions which preferably upon completion of the oxirane/syngas reaction cause a phase separation of the reaction mixture into a solvent phase which is rich in catalyst and a second phase which is rich in the 1,3-diol, recycling the phase rich in catalyst directly to the hydroformylation reaction for further reaction with previously unreacted starting materials, thus permitting valuable hydroformylation catalyst to be recycled without degradation or exposure to downstream processing and recovering the 1,3-diol from the second phase rich in 1,3-diol.

One step process for preparing A 1,3-diol

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Austin, TX, United States of America

John F Knifton