US 6,583,329 B1Granted

Olefin metathesis in a distillation column reactor

AssigneeCatalytic Distillation Technologies

InventorGary G. Podrebarac

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Abstract

The metathesis process is carried out in a reaction distillation column for: (A) for the production of propylene from the metathesis of 2-butene and ethylene; (B) for the production of detergent range olefins from the metathesis of C15 and heavier olefins with C9 and lighter olefins; (C) for the production of 2-methyl-2-butene and propylene from the metathesis of 2-butene and isobutylene and (D) for the production of tetramethylethylene from the metathesis of isobutylene with itself and/or the reaction of diisobutylene with the ethylene produced to produce neohexene.

Claims31

Dependent claims

A metathesis process for

(A) the production of propylene from the metathesis of 2-butene and ethylene comprising the steps of:
(a) feeding a first stream comprising ethylene to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) feeding a second stream comprising 2-butene to said distillation column reactor,
(c) concurrently in said distillation column reactor
(i) contacting said 2-butene and said ethylene with said fixed bed metathesis catalyst so as to react at least a portion of said ethylene with at least a portion of said 2-butene to produce propylene and create a reaction mixture containing unreacted 2-butene, unreacted ethylene and propylene product;
(ii) separating the unreacted ethylene and propylene product from the unreacted 2-butene by fractional distillation and
(iii) azeotropically removing water present in said first and second streams and
(d) removing the unreacted ethylene and propylene product from said distillation column reactor as overheads product;
(B) the production of detergent range olefins from the metathesis of C15 and heavier olefins comprising the steps of:
(a) feeding a first stream comprising C9 and lighter olefins to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) feeding a second stream comprising C15 and heavier olefins to said distillation column reactor,
(c) concurrently in said distillation column reactor:
(i) contacting said C9 and lighter olefins and said C15 and heavier olefins with said fixed bed metathesis catalyst so as to react at least a portion of said C9 and lighter olefins with at least a portion of said C15 and heavier olefins to produce detergent range olefins and create a reaction mixture containing unreacted C9 and lighter olefins, unreacted C15 and heavier olefins and detergent range olefin product;
(ii) separating the unreacted C15 and heavier olefins and detergent range olefin from the C9 and lighter olefins by fractional distillation and
(iii) azeotropically removing water present in said first and second streams and
(d) removing the unreacted C15 and heavier olefins and detergent range olefin from said distillation column reactor as bottoms product;
(C) the production of 2-methyl-2-butene and propylene from the metathesis of isobutylene and 2-butene comprising the steps of:
(a) feeding a first stream comprising isobutylene to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) feeding a second stream comprising 2-butene to said distillation column reactor,
(c) concurrently in said distillation column reactor
(i) contacting said 2-butene and said isobutylene with said fixed bed metathesis catalyst so as to react at least a portion of said isobutylene with at least a portion of said 2-butene to produce propylene and 2-methyl-2-butene and create a reaction mixture containing unreacted 2-butene, unreacted isobutylene, propylene product and 2-methyl-2-butene product;
(ii) separating the unreacted isobutylene and propylene product from the unreacted 2-butene and 2-methyl-2-butene product by fractional distillation, and
(iii) azeotropically removing water present in said first and second streams
(d) removing the unreacted isobutylene and propylene product from said distillation column reactor as overheads product, and
(e) removing the 2-methyl-2-butene product from said distillation column reactor as bottoms;
or
(D) the production of tetramethylethylene from the metathesis of isobutylene with itself comprising the steps of:
(a) feeding isobutylene to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) concurrently in said distillation column reactor,
(i) contacting said isobutylene with said fixed bed metathesis catalyst so as to react at least a portion of said isobutylene to produce tetramethylethylene and ethylene and create a reaction mixture containing unreacted isobutylene, ethylene and tetramethylethylene product;
(ii) separating the ethylene and unreacted isobutylene from the tetramethylethylene by fractional distillation, and
(iii) azeotropically removing water present in said first and second streams
(c) removing the ethylene and isobutylene from said distillation column reactor as overheads product and
(d) removing the tetramethylethylene product from said distillation column reactor as bottoms.

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Dependencies are inferred from the claim text.

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Abstract

A metathesis process for

(A) the production of propylene from the metathesis of 2-butene and ethylene comprising the steps of:
(a) feeding a first stream comprising ethylene to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) feeding a second stream comprising 2-butene to said distillation column reactor,
(c) concurrently in said distillation column reactor
(i) contacting said 2-butene and said ethylene with said fixed bed metathesis catalyst so as to react at least a portion of said ethylene with at least a portion of said 2-butene to produce propylene and create a reaction mixture containing unreacted 2-butene, unreacted ethylene and propylene product;
(ii) separating the unreacted ethylene and propylene product from the unreacted 2-butene by fractional distillation and
(iii) azeotropically removing water present in said first and second streams and
(d) removing the unreacted ethylene and propylene product from said distillation column reactor as overheads product;
(B) the production of detergent range olefins from the metathesis of C15 and heavier olefins comprising the steps of:
(a) feeding a first stream comprising C9 and lighter olefins to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) feeding a second stream comprising C15 and heavier olefins to said distillation column reactor,
(c) concurrently in said distillation column reactor:
(i) contacting said C9 and lighter olefins and said C15 and heavier olefins with said fixed bed metathesis catalyst so as to react at least a portion of said C9 and lighter olefins with at least a portion of said C15 and heavier olefins to produce detergent range olefins and create a reaction mixture containing unreacted C9 and lighter olefins, unreacted C15 and heavier olefins and detergent range olefin product;
(ii) separating the unreacted C15 and heavier olefins and detergent range olefin from the C9 and lighter olefins by fractional distillation and
(iii) azeotropically removing water present in said first and second streams and
(d) removing the unreacted C15 and heavier olefins and detergent range olefin from said distillation column reactor as bottoms product;
(C) the production of 2-methyl-2-butene and propylene from the metathesis of isobutylene and 2-butene comprising the steps of:
(a) feeding a first stream comprising isobutylene to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) feeding a second stream comprising 2-butene to said distillation column reactor,
(c) concurrently in said distillation column reactor
(i) contacting said 2-butene and said isobutylene with said fixed bed metathesis catalyst so as to react at least a portion of said isobutylene with at least a portion of said 2-butene to produce propylene and 2-methyl-2-butene and create a reaction mixture containing unreacted 2-butene, unreacted isobutylene, propylene product and 2-methyl-2-butene product;
(ii) separating the unreacted isobutylene and propylene product from the unreacted 2-butene and 2-methyl-2-butene product by fractional distillation, and
(iii) azeotropically removing water present in said first and second streams
(d) removing the unreacted isobutylene and propylene product from said distillation column reactor as overheads product, and
(e) removing the 2-methyl-2-butene product from said distillation column reactor as bottoms;
or
(D) the production of tetramethylethylene from the metathesis of isobutylene with itself comprising the steps of:
(a) feeding isobutylene to a distillation column reactor containing a fixed bed of metathesis catalyst,
(b) concurrently in said distillation column reactor,
(i) contacting said isobutylene with said fixed bed metathesis catalyst so as to react at least a portion of said isobutylene to produce tetramethylethylene and ethylene and create a reaction mixture containing unreacted isobutylene, ethylene and tetramethylethylene product;
(ii) separating the ethylene and unreacted isobutylene from the tetramethylethylene by fractional distillation, and
(iii) azeotropically removing water present in said first and second streams
(c) removing the ethylene and isobutylene from said distillation column reactor as overheads product and
(d) removing the tetramethylethylene product from said distillation column reactor as bottoms.

31 more elements