US4891448A
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US
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Alkylation of polycyclic aromatic compounds to alkylates enriched in the para-substituted isomers
Assignee: Dow Chemical Co
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Filing: 1987-11-23
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Granted: 1990-01-02
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Expires: 2007-11-23
Abstract
Abstract Polycyclic aromatic compounds, such as biphenyl, are alkylated with an alkylating agent, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted polycyclic aromatic compounds enriched in the para alkylated isomers, such as p,p'-di(isopropyl)biphenyl. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of polycyclic aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.
Inventors
- 👤 Juan Garces
- 👤 Joseph J. Maj
- 👤 G. John Lee
- 👤 Stephen C. Rocke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:44
CPC Classifications
B; B01; B01J; B01J20/00; B01J20/02; B01J20/10; B01J20/16; C; C07; C07C; C07C41/00; C07C41/01; C07C41/18; C07C41/30; B01J29/00; B01J29/04; B01J29/06; B01J29/18; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/14; C07C2/16; C07C2/54; C07C2/64; C07C2/66; C07C2/86; C07C2/862; C07C2/864; C07C37/00; C07C37/11; C07C37/14; C07C2529/00; C07C2529/04; C07C2529/06; C07C2529/18; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
97 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 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 comprising 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 be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
Claim 2
Dependent Claim
97 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 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 comprising 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 be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
Claim 3
Dependent Claim
21 words
The process of claim 1 wherein the polycyclic aromatic compound is a C 10 -C 24 fused or non-fused aromatic compound.
Claim 4
Dependent Claim
97 words
The process of claim 2 wherein the non-fused polycyclic aromatic compound is represented by the formula: ##STR2## wherein n is a positive number from 1 to 3; Y is hydrogen, hydroxyl, sulfhydryl, alkyl of C 1-10 carbons atoms, aliphatic alkoxy or thioalkoxy of C 1-10 carbon atoms, fluoro, chloro, or bromo; and X is absent such that the phenyl rings are bonded at the 1,1' positions to each other, or X is O, S, SO, SO 2 , CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , or CHCH 3 .
Claim 5
Dependent Claim
16 words
The process of claim 2 wherein the polycyclic aromatic compound is biphenyl, naphthalene, or diphenyl ether.
Claim 6
Dependent Claim
12 words
The process of claim 4 wherein the polycyclic aromatic compound is biphenyl.
Claim 7
Dependent Claim
12 words
The process of claim 4 wherein the polycyclic aromatic compound is diphenylether.
Claim 8
Dependent Claim
17 words
The process of claim 1 wherein the alkylating agent is a monoolefin, a diolefin, or an alcohol.
Claim 9
Dependent Claim
15 words
The process of claim 7 wherein the monoolefin is propylene, n-butene, 1-hexene, cyclohexene, or 1-octene.
Claim 10
Dependent Claim
10 words
The process of claim 8 wherein the olefin is propylene.
Claim 11
Dependent Claim
10 words
The process of claim 8 wherein the olefin is n-butene.
Claim 12
Dependent Claim
20 words
The process of claim 1 wherein the temperature is in the range from about 150° C. to about 300° C.
Claim 13
Dependent Claim
25 words
The process of claim 1 wherein the polycyclic aromatic compound is in the neat, liquid state and the alkylating agent is in the liquid state.
Claim 14
Dependent Claim
15 words
The process of claim 1 wherein the polycyclic aromatic compound is dissolved in a solvent.
Claim 15
Dependent Claim
12 words
The process of claim 13 wherein the solvent is 1,3,5-triisopropylbenzene or decalin.
Claim 16
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 17
Dependent Claim
15 words
The process of claim 1 wherein the yield of dialkylates is at least 60 percent.
Claim 18
Dependent Claim
70 words
The process of claim 1 wherein the catalyst has a silica/alumina molar ratio of at least 50:1, a Symmetry Index of at least 1.0, 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 19
Dependent Claim
20 words
The process of claim 1 wherein the yield of the para alkylated isomers is at least about 10 mole percent.
Claim 20
Dependent Claim
18 words
The process of claim 18 wherein the yield of alkylated isomers is at least about 40 mole percent.
Claim 21
Dependent Claim
19 words
The process of claim 19 wherein the yield of para alkylated isomers is at least about 70 mole percent.
Claim 22
Dependent Claim
84 words
A process of alkylating biphenyl to a mixture of disubstituted products enriched in 4,4'-(dialkylate)-1,1'-biphenyl comprising contacting biphenyl with an alkylating agent in the presence of a catalyst under conditions such that the 4,4'-dialkylated isomer is formed in a yield of at least 40 percent, said catalyst comprising 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 be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
Claim 23
Dependent Claim
84 words
A process of alkylating biphenyl to a mixture of disubstituted products enriched in 4,4'-(dialkylate)-1,1'-biphenyl comprising contacting biphenyl with an alkylating agent in the presence of a catalyst under conditions such that the 4,4'-dialkylated isomer is formed in a yield of at least 40 percent, said catalyst comprising 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 be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
Claim 24
Dependent Claim
20 words
The process of claim 1 wherein the mixture of substituted polycyclic aromatic compounds is enriched in the para alkylated isomers.
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