US 2007/0100181 A1Published application

Olefin isomerization

OwnerMark Harmer, Christopher Junkinventors

Life of this patent

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Abstract

This invention relates to a process for isomerizing olefins; the reaction is carried out in the presence of at least one ionic liquid.

Claims13

Dependent claims

A process for making internal olefins comprising:

(A) forming a reaction mixture comprising (1) at least one α-olefin having from 4 to 25 carbons, (2) at least one acid catalyst selected from the group consisting of rare earth fluorinated alkyl sulfonates, organic sulfonic acids, fluoroalkyl sulfonic acids, metal sulfonates, metal trifluoroacetates, and combinations thereof, and (3) at least one ionic liquid having the Formula Z+A−, wherein Z+ is a cation selected from the group consisting of:
wherein R1, R2, R3, R4, R5and R6 are independently selected from the group consisting of:
(i) H
(ii) halogen
(iii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(iv) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(v) C6 to C25 unsubstituted aryl or unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and
(vi) C6 to C25 substituted aryl or substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of
(1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
(2) OH,
(3) NH2, and
(4) SH;
R7, R8, R9, and R10 are independently selected from the group consisting of:
(vii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(viii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(ix) C6 to C25 unsubstituted aryl, or C3 to C25 unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and
(x) C6 to C25 substituted aryl, or C3 to C25 substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of
(1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
(2) OH,
(3) NH2, and
(4) SH;
wherein optionally at least two of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 can together form a cyclic or bicyclic alkanyl or alkenyl group;
and
A− is R11—SO3— or (R12—SO2)2N−;
wherein R11 and R12 are independently selected from the group consisting of:
(a) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(b) —CH3, —C2H5, or C3 to C25 straight—chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(c) C6 to C25 unsubstituted aryl or unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and
(d) C6 to C25 substituted aryl or substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of:
(1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
(2) OH,
(3) NH2, and
(4) SH;
thereby forming an isomer phase comprising at least one internal olefin and an ionic liquid phase that comprises the at least one acid catalyst;
and
B) separating the isomer phase from the ionic liquid phase, thereby forming a separated ionic liquid phase.

39 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/583,342Filed 19 Oct 2006
Priority: 27 Oct 2005
Published: 3 May 2007
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07C 5/2531
With inorganic acids; with salts or anhydrides of acids: acids of sulfur; Salts thereof; Sulfur oxides
C07C 5/2562
Catalytic processes: with hydrides or organic compounds
C07C 2527/053
Sulfur, selenium or tellurium; Compounds thereof: sulfates or other compounds comprising the anion 2-
C07C 2531/025
Containing organic compounds or metal hydrides: sulfonic acids

Family

Application60/730,716Us provisional application · filed 27 Oct 2005
US 2007/0100181 A1This patent

From the US filing history. Foreign family members aren’t listed.

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A process for making internal olefins comprising:

(A) forming a reaction mixture comprising (1) at least one α-olefin having from 4 to 25 carbons, (2) at least one acid catalyst selected from the group consisting of rare earth fluorinated alkyl sulfonates, organic sulfonic acids, fluoroalkyl sulfonic acids, metal sulfonates, metal trifluoroacetates, and combinations thereof, and (3) at least one ionic liquid having the Formula Z+A−, wherein Z+ is a cation selected from the group consisting of:
wherein R1, R2, R3, R4, R5and R6 are independently selected from the group consisting of:
(i) H
(ii) halogen
(iii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(iv) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(v) C6 to C25 unsubstituted aryl or unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and
(vi) C6 to C25 substituted aryl or substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of
(1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
(2) OH,
(3) NH2, and
(4) SH;
R7, R8, R9, and R10 are independently selected from the group consisting of:
(vii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(viii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(ix) C6 to C25 unsubstituted aryl, or C3 to C25 unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and
(x) C6 to C25 substituted aryl, or C3 to C25 substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of
(1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
(2) OH,
(3) NH2, and
(4) SH;
wherein optionally at least two of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 can together form a cyclic or bicyclic alkanyl or alkenyl group;
and
A− is R11—SO3— or (R12—SO2)2N−;
wherein R11 and R12 are independently selected from the group consisting of:
(a) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(b) —CH3, —C2H5, or C3 to C25 straight—chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
(c) C6 to C25 unsubstituted aryl or unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and
(d) C6 to C25 substituted aryl or substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N and S;
and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of:
(1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
(2) OH,
(3) NH2, and
(4) SH;
thereby forming an isomer phase comprising at least one internal olefin and an ionic liquid phase that comprises the at least one acid catalyst;
and
B) separating the isomer phase from the ionic liquid phase, thereby forming a separated ionic liquid phase.

39 more elements

Facts

Application

11/583,342Filed 19 Oct 2006

Priority

27 Oct 2005

Published

3 May 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07C 5/2531
With inorganic acids; with salts or anhydrides of acids: acids of sulfur; Salts thereof; Sulfur oxides
C07C 5/2562
Catalytic processes: with hydrides or organic compounds
C07C 2527/053
Sulfur, selenium or tellurium; Compounds thereof: sulfates or other compounds comprising the anion 2-
C07C 2531/025
Containing organic compounds or metal hydrides: sulfonic acids