IP Library Granted Patent US 7,655,821
Granted Patent B1
US 7,655,821 · App. 12/313,814 · Granted Feb 2, 2010

Direct hydrocarbonylation process

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Quick Facts
Patent No.
US 7,655,821
App. No.
12/313,814
Granted
Feb 2, 2010
Kind
B1
Abstract

A direct hydrocarbonylation process for the production of 1,4-butanediol is described. The process comprises reacting allyl alcohol with carbon monoxide and hydrogen in an alcohol solvent in the presence of a catalyst system comprising a rhodium complex, a trialkyl phosphine, and a diphosphine. The process gives a high yield of 1,4-butanediol in a one-step reaction.

Claims (10)

1. A process to produce 1,4-butanediol, comprising reacting allyl alcohol with carbon monoxide and hydrogen in an alcohol solvent in the presence of a catalyst system comprising a rhodium complex, a trialkyl phosphine ligand, and a diphosphine ligand, wherein the molar ratio of diphosphine:trialkyl phosphine is about 0.5 to about 2.

2. The process of claim 1 wherein the trialkyl phosphine ligand is selected from the group consisting of trimethyl phosphine, triethyl phosphine, tri-n-propyl phosphine, tri-n-butyl phosphine, and mixtures thereof.

3. The process of claim 1 wherein the diphosphine ligand is a trans-1,2-bis(bis(3,5-di-n-alkylphenyl)phosphinomethyl)cyclobutane.

4. The process of claim 1 wherein the diphosphine ligand is a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,5-di-n-alkylphenyl)phosphino]butane.

5. The process of claim 1 wherein the diphosphine ligand is DIOP.

6. The process of claim 1 wherein the alcohol solvent is a C 1 -C 4 aliphatic alcohol.

7. The process of claim 1 wherein the rhodium complex comprises rhodium and ligands selected from the group consisting of hydride, carbonyl, trialkyl or triaryl phosphines, diphosphines, cyclopentadienyls, 2,4-alkanedionates, and mixtures thereof.

8. The process of claim 1 wherein the reaction is performed at a temperature within the range of about 70° C. to about 140° C. and a pressure within the range of about 50 to about 1000 psig.

9. The process of claim 1 wherein the reaction is performed at a temperature within the range of about 90° C. to about 130° C. and a pressure within the range of about 200 to about 600 psig.

10. The process of claim 1 wherein the molar ratio of hydrogen to carbon monoxide is 2:1 or greater.

Assignments (14)
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032123/0799 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: CITIBANK, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032125/0296 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032137/0156 →
APPOINTMENT OF SUCCESSOR ADMINISTRATIVE AGENT Recorded Jan 23, 2014
From: UBS AG, STAMFORD BRANCH
To: BANK OF AMERICA, N.A.
Reel/Frame 032137/0639 →
RELEASE OF SECURITY INTEREST Recorded Jan 23, 2014
From: BANK OF AMERICA, N.A.
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032138/0134 →
SECURITY AGREEMENT Recorded May 19, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 024402/0681 →
SECURITY AGREEMENT Recorded May 18, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024397/0818 →
SECURITY AGREEMENT Recorded May 7, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 024342/0801 →
SECURITY AGREEMENT Recorded May 6, 2010
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 024342/0421 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0285 →
RELEASE OF SECURITY INTEREST Recorded May 5, 2010
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: LYONDELL CHEMICAL TECHNOLOGY, LP
Reel/Frame 024337/0020 →
SECURITY AGREEMENT Recorded Oct 30, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 023449/0138 →
SECURITY AGREEMENT Recorded Apr 9, 2009
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
Reel/Frame 022708/0830 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2009
From: WHITE, DANIEL F.; COLE-HAMILTON, DAVID JOHN; BOOGAERTS, INE
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 022103/0417 →