Back to results
US 5,057,638 AGranted
Process for making 1-hexene from 1-butene
AssigneeChevron Research and Technology Company
InventorWilliam A. Sweeney
Life of this patent
Estimating the term…
Abstract
Disclosed is a process for preparing 1-hexene from 1-butene. The 1-butene is metathesized to produce 3-hexene which is then subjected to, e.g., an hydration/dehydration procedure to produce a mixture of n-hexenes containing 1-hexene.
Claims18
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic compound containing reactive hydrogen under acid catalyzed conditions which permit the electrophilic compound containing reactive hydrogen to add to carbon-carbon double bonds;
- and
- D. cracking the product of step C to produce a mixture of n-hexenes containing 1-hexene.
2 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic compound containing reactive hydrogen under acid catalyzed conditions which permit the electrophilic compound containing reactive hydrogen to add to carbon-carbon double bonds;
- D. separating the 2-isomer produced in step C from the product of step C;
- and
- E. cracking said 2-isomer to produce a mixture of n-hexenes containing 1-hexene.
3 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic compound containing reactive hydrogen under conditions which permit the electrophilic compound to add to carbon-carbon double bonds, said electrophilic compound being hydrolyzable to an alcohol after addition to the carbon-carbon double bond;
- D. hydrolyzing the product of step C to produce of mixture of C.sub.6 alcohols;
- and
- E. cracking the product of step D to produce a mixture of n-hexenes containing 1-hexene
3 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic compound containing reactive hydrogen under conditions which permit the electrophilic compound to add to carbon-carbon double bonds, said electrophilic compound being hydrolyzable to an alcohol after addition to the carbon-carbon double bond;
- D. hydrolyzing the product of step C to produce of mixture of C.sub.6 alcohols;
- E. separating 2-hexanol from the mixture of C.sub.6 alcohols produced in step D;
- and
- F. cracking the 2-hexanol to produce a mixture of n-hexenes containing 1-hexene
4 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic reactant selected from the group consisting of water and a hydrolyzable electrophilic compound containing reactive hydrogen under acid catalyzed conditions which permit the electrophilic reactant to add to carbon-carbon double bonds;
- D. when the electrophilic reactant employed in step C is a hydrolyzable eIectrophilic compound containing reactive hydrogen, hydrolyzing the product of step C to form alcohols;
- E. converting the alcohols to alkyl xanthates;
- and
- F. cracking the product of step E to produce a mixture of n-hexenes containing 1-hexene.
4 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic reactant selected from the group consisting of water and a hydrolyzable electrophilic compound containing reactive hydrogen under acid catalyzed conditions which permit the electrophilic reactant to add to carbon-carbon double bonds;
- D. when the electrophilic reactant employed in step C is a hydrolyzable electrophilic compound containing reactive hydrogen, hydrolyzing the product of step C to form alcohols;
- E. converting the alcohols produced to alkyl xanthates;
- F. separating the 2-xanthate from the product of step E;
- and
- G. cracking the 2-xanthate to produce a mixture of n-hexenes containing 1-hexene.
5 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic compound containing reactive hydrogen under conditions which permit the electrophilic compound containing reactive hydrogen to add to carbon-carbon double bonds;
- D. cracking the product of step C to produce a mixture of 2-hexene and 3-hexene;
- E. reacting the mixture of 2-hexene and 3-hexene produced in step D with an electrophilic compound containing reactive hydrogen under conditions which permit the electrophilic compound containing reactive hydrogen to add to carbon-carbon double bonds;
- and
- F. cracking the product of step E to produce a mixture of n-hexenes containing 1-hexene.
4 more elements
A process for making 1-hexene comprising:
- A. metathesizing 1-butene to a mixture comprising 3-hexene and ethylene;
- B. separating the 3-hexene from the product of step A;
- C. reacting the 3-hexene with an electrophilic compound containing reactive hydrogen under conditions which permit the electrophilic compound containing reactive hydrogen to add to carbon-carbon double bonds;
- D. cracking the product of step C to produce a mixture of 2-hexene and 3-hexene;
- E. reacting the mixture of 2-hexene and 3-hexene produced in step D with an electrophilic compound containing reactive hydrogen under conditions which permit the electrophilic compound containing reactive hydrogen to add to carbon-carbon double bonds;
- F. separating the 2-isomer produced in step E from the product of step E;
- and
- G. cracking said 2-isomer to produce a mixture of n-hexenes containing 1-hexene.
5 more elements
Dependencies are inferred from the claim text.