US5004841A — Alkylation of aromatic compounds to alkylates enr…

Claim 1

Independent Claim 109 words

A process of alkylating an aromatic compound to a mixture of substituted aromatic compounds enriched in the linear alkylated isomers comprising contacting an aromatic compound with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that a mixture of substituted aromatic compounds enriched in the linear alkylated isomers is formed, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index sufficient to increase the yield of linear alkylated isomers to at least about 20 mole percent.

Claim 2

Dependent Claim 109 words

A process of alkylating an aromatic compound to a mixture of substituted aromatic compounds enriched in the linear alkylated isomers comprising contacting an aromatic compound with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that a mixture of substituted aromatic compounds enriched in the linear alkylated isomers is formed, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index sufficient to increase the yield of linear alkylated isomers to at least about 20 mole percent.

Claim 3

Dependent Claim 11 words

The process of claim 1 wherein the aromatic compound is monocyclic.

Claim 4

Dependent Claim 39 words

The process of claim 2 wherein the aromatic compound is represented by the formula: ##STR3## wherein Z is hydrogen, sulfhydryl, alkyl of C 1-10 carbon atoms, aliphatic alkoxy or thioalkoxy of C 1-10 carbon atoms, fluoro, chloro, or bromo.

Claim 5

Dependent Claim 19 words

The process of claim 3 wherein the aromatic compound is selected from the group consisting of benzene and cumene.

Claim 6

Dependent Claim 14 words

The process of claim 2 wherein the Symmetry Index is at least about 1.5.

Claim 7

Dependent Claim 21 words

The process of claim 1 wherein the aromatic compound is a C 10 -C 24 fused or non-fused polycyclic aromatic compound.

Claim 8

Dependent Claim 81 words

The process of claim 6 wherein the non-fused polycyclic aromatic compound is represented by the formula: ##STR4## wherein n is a positive number from 1 to 3; Y is hydrogen, hydroxyl, sulfhydryl, alkyl of C 1-10 carbon atoms, aliphatic alkoxy or thioalkoxy of C 1-10 carbon atoms, fluoro, chloro, or bromo: and X is absent or is O, S, SO, SO 2 , CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 or CHCH 3 .

Claim 9

Dependent Claim 16 words

The process of claim 7 wherein the polycyclic aromatic compound is biphenyl, naphthalene, or diphenyl ether.

Claim 10

Dependent Claim 12 words

The process of claim 8 wherein the polycyclic aromatic compound is biphenyl.

Claim 11

Dependent Claim 12 words

The process of claim 8 wherein the polycyclic aromatic compound is diphenylether.

Claim 12

Dependent Claim 14 words

The process of claim 6 wherein the Symmetry Index is at least about 1.0.

Claim 13

Dependent Claim 17 words

The process of claim 1 wherein the alkylating agent is a monoolefin, a diolefin, or an alcohol.

Claim 14

Dependent Claim 15 words

The process of claim 12 wherein the monoolefin is propylene, n-butene, 1-hexene, cyclohexene, or 1-octene.

Claim 15

Dependent Claim 10 words

The process of claim 13 wherein the olefin is propylene.

Claim 16

Dependent Claim 10 words

The process of claim 13 wherein the olefin is n-butene.

Claim 17

Dependent Claim 20 words

The process of claim 1 wherein the temperature is in the range from about 100° C. to about 400° C.

Claim 18

Dependent Claim 25 words

The process of claim 1 wherein the aromatic compound is in the neat, liquid state and the alkylating agent is dissolved in the liquid state.

Claim 19

Dependent Claim 14 words

The process of claim 1 wherein the aromatic compound is dissolved in a solvent.

Claim 20

Dependent Claim 12 words

The process of claim 18 wherein the solvent is 1,3,5-triisopropylbenzene or decalin.

Claim 21

Dependent Claim 20 words

The process of claim 1 wherein the pressure is in the range from about 10 psig to about 500 psig.

Claim 22

Dependent Claim 20 words

The process of claim 1 wherein the yield of total dialkylates ranges from about 25 to about 80 mole percent.

Claim 23

Dependent Claim 72 words

The process of claim 1 wherein the catalyst has a silica/alumina molar ratio of at least 50:1, a Symmetry Index from about 1.0 to about 2.3, and a porosity such that the total pore volume is in the range from about 0.18 cc/g to about 0.45 cc/g and the ratio of the combined meso- and macropore volume to the total pore volume is in the range from about 0.25 to about 0.75.

Claim 24

Dependent Claim 20 words

The process of claim 1 wherein the yield of the linear alkylated isomers is at least about 40 mole percent.

Claim 25

Dependent Claim 20 words

The process of claim 23 wherein the yield of the linear alkylated isomers is at least about 70 mole percent.

Claim 26

Dependent Claim 90 words

A process of alkylating biphenyl to a mixture of products enriched in 4,4'-(dialkylate)-1,1'-biphenyl comprising contacting biphenyl with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that the 4,4'-dialkylated isomer is formed in a yield of at least about 20 mole percent, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least about 1.0.

Claim 27

Dependent Claim 90 words

A process of alkylating biphenyl to a mixture of products enriched in 4,4'-(dialkylate)-1,1'-biphenyl comprising contacting biphenyl with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that the 4,4'-dialkylated isomer is formed in a yield of at least about 20 mole percent, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least about 1.0.

Claim 28

Dependent Claim 91 words

A process of alkylating benzene to a mixture of products enriched in para-dialkylated benzene comprising contacting benzene with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that the para-dialkylated isomer is formed in a yield of at least about 20 mole percent, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least about 1.5.

Claim 29

Dependent Claim 91 words

A process of alkylating benzene to a mixture of products enriched in para-dialkylated benzene comprising contacting benzene with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that the para-dialkylated isomer is formed in a yield of at least about 20 mole percent, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least about 1.5.

Claim 30

Dependent Claim 101 words

A process of alkylating a polycyclic aromatic compound to a mixture of substituted polycyclic aromatic compounds enriched in the linear alkylated isomers comprising contacting a polycyclic aromatic compound with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that a mixture of substituted polycyclic aromatic compounds enriched in the linear alkylated isomers is formed, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least 1.0.

Claim 31

Dependent Claim 101 words

A process of alkylating a polycyclic aromatic compound to a mixture of substituted polycyclic aromatic compounds enriched in the linear alkylated isomers comprising contacting a polycyclic aromatic compound with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that a mixture of substituted polycyclic aromatic compounds enriched in the linear alkylated isomers is formed, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least 1.0.

Claim 32

Dependent Claim 101 words

A process of alkylating a monocyclic aromatic compound to a mixture of substituted monocyclic aromatic compounds enriched in the linear alkylated isomers comprising contacting a monocyclic aromatic compound with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that a mixture of substituted monocyclic aromatic compounds enriched in the linear alkylated isomers is formed, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least 1.5.

Claim 33

Dependent Claim 101 words

A process of alkylating a monocyclic aromatic compound to a mixture of substituted monocyclic aromatic compounds enriched in the linear alkylated isomers comprising contacting a monocyclic aromatic compound with an alkylating agent having from one to eight carbon atoms in the presence of a catalyst under conditions such that a mixture of substituted monocyclic aromatic compounds enriched in the linear alkylated isomers is formed, said catalyst consisting essentially of an acidic mordenite zeolite having a silica/alumina molar ratio of at least 15:1 and a crystalline structure which is determined by X-ray diffraction to possess a Symmetry Index of at least 1.5.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1994-04-01	1994-10-01	1995-04-02	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1998-04-01	1998-10-01	1999-04-02	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2002-04-01	2002-10-01	2003-04-02	$7700.00	Window Closed / Lapsed

Alkylation of aromatic compounds to alkylates enriched in the linear-substituted isomers

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