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US 2017/0320792 A1Published application
Tandem transfer hydrogenation and oligomerization for hydrocarbon production
AssigneeCalifornia Institute of Technology
InventorsDavid Leitch, Jay A. Labinger, John E. Bercaw, Yan Choi Lam
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Abstract
A method for coupling an alkane with an alkene using a hydrogen transfer catalyst and an alkene dimerization catalyst to form one or more higher molecular weight hydrocarbons.
Claims20
A method of coupling a n-alkane reactant with a n-alkene reactant so as to form one or more branched alkene products in a single tandem process, comprising:
- coupling a n-alkane reactant with a n-alkene reactant in the presence of a catalyst comprising:
- (i) a hydrogen transfer catalyst and (ii) an alkene dimerization catalyst so as to generate one or more branched alkene products, wherein the molecular weight of the one or more branched alkene products is greater than the molecular weight of the n-alkane reactant and greater than the molecular weight of the n-alkene reactant;
- wherein the hydrogen transfer catalyst is a pincer complex catalyst, and
- wherein the alkene dimerization catalyst is a tantalum catalyst that is selective for the formation of dimer products comprising a structure of Formula II:
- wherein,
- Z is either 1 or 2;
- n is an integer from 1 to 5;
- each Y is independently selected from the group consisting of D, H, optionally substituted C1-C6 alkyl, silane, and C1-C4 alkylsilane;
- Y1 is selected from the group consisting of H, D, halo, ═S, ═O, PMe3, and ═C(H) (CMe3);
- Y2 is selected from the group consisting of H, D, halo, ═S, ═O, and PMe3, or Y2 is absent;
- R2 is selected from the group consisting of H, aryl, optionally substituted C1-C15 alkyl, and optionally substituted C1-C15 hetero-alkyl;
- and
- R3 is selected from the group consisting of H, aryl, optionally substituted C1-C15 alkyl, and optionally substituted C1-C15 hetero-alkyl,
- wherein the one or more branched alkene products comprise one or more carbon atoms from both the n-alkane reactant and the n-alkene reactant.
11 more elements
A method for coupling a first n-alkane reactant with a second n-alkane reactant to form one or more branched alkene products, comprising:
- coupling the first n-alkane reactant with the second n-alkane reactant using styrene as a sacrificial hydrogen acceptor in the presence of a catalyst comprising:
- (i) a hydrogen transfer catalyst and (ii) an alkene dimerization catalyst so as to generate one or more branched alkene products, wherein the molecular weight of the one or more branched alkene products is greater than the molecular weight of the first n-alkane reactant and greater than the molecular weight of the second n-alkane reactant;
- wherein the hydrogen transfer catalyst is a pincer complex catalyst, and
- wherein the alkene dimerization catalyst is a tantalum catalyst that is selective for the formation of dimer products comprising a structure of Formula II,
- wherein:
- Z is either 1 or 2;
- n is an integer from 1 to 5;
- each Y is independently selected from the group consisting of D, H, optionally substituted C1-C6 alkyl, silane, and C1-C4 alkylsilane;
- Y1 is selected from the group consisting of H, D, halo, ═S, ═O, PMe3, and ═C(H) (CMe3)
- Y2 is selected from the group consisting of H, D, halo, ═S, ═O, PMe3, or Y2 is absent;
- R2 is selected from the group consisting of H, aryl, optionally substituted C1-C15 alkyl, and optionally substituted C1-C15 hetero-alkyl;
- and
- R3 is selected from the group consisting of H, aryl, optionally substituted C1-C15 alkyl, and optionally substituted C1-C15 hetero-alkyl,
- wherein the one or more branched alkene products comprise carbon atoms from both the first n-alkane reactant and the second n-alkane reactant.
11 more elements
A method of coupling a n-alkane reactant with a n-alkene reactant so as to form one or more branched alkene products in a single tandem process, comprising:
- coupling a n-alkane reactant with a n-alkene reactant in the presence of a catalyst comprising:
- (i) a hydrogen transfer catalyst and (ii) an alkene dimerization catalyst so as to generate one or more branched alkene products, wherein the molecular weight of the one or more branched alkene products is greater than the molecular weight of the n-alkane reactant and greater than the molecular weight of the n-alkene reactant;
- wherein the alkene dimerization catalyst is a tantalum catalyst that is selective for the formation of dimer products, and
- wherein the hydrogen transfer catalyst is an iridium pincer complex catalyst comprising the structure of Formula I:
- wherein,
- each R is independently a H or a C1-C30 hydrocarbyl radical;
- each R1 is independently a C1-C30 hydrocarbyl radical;
- and
- each X is independently an O or CH2,
- wherein the one or more branched alkene products comprise one or more carbon atoms from both the n-alkane reactant and the n-alkene reactant.
7 more elements
A method for coupling a first n-alkane reactant with a second n-alkane reactant to form one or more branched alkene products, comprising:
- coupling the first n-alkane reactant with the second n-alkane reactant using styrene as a sacrificial hydrogen acceptor in the presence of a catalyst comprising:
- (i) a hydrogen transfer catalyst and (ii) an alkene dimerization catalyst so as to generate one or more branched alkene products, wherein the molecular weight of the one or more branched alkene products is greater than the molecular weight of the first n-alkane reactant and greater than the molecular weight of the second n-alkane reactant;
- wherein the alkene dimerization catalyst is a tantalum catalyst that is selective for the formation of dimer products, and wherein the hydrogen transfer catalyst is an iridium pincer complex catalyst comprising a structure of Formula I,
- wherein,
- each R is independently a H or a C1-C30 hydrocarbyl radical;
- each R1 is independently a C1-C30 hydrocarbyl radical;
- and
- each X is independently an O or CH2,
- wherein the one or more branched alkene products comprise one or more carbon atoms from both the n-alkane reactant and the n-alkene reactant,
- wherein the one or more branched alkene products comprise carbon atoms from both the first n-alkane reactant and the second n-alkane reactant.
7 more elements
Dependencies are inferred from the claim text.