US4927979A
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US
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Process for the preparation of p-ethylphenol
Assignee: Maruzen Petrochemical Co Ltd
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Filing: 1988-12-06
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Granted: 1990-05-22
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Expires: 2008-12-06
Abstract
Abstract A very simple process for preparing p-ethylphenol is disclosed. It is only necessary to contact phenol with an ethylating agent in vapor phase in the presence of a specific catalyst. The catalyst can be obtained by incorporating one or more alkoxysilanes to a crystalline aluminosilicte with a constraint index of 1-15 having a silica/alumina molar ratio of 20-400, wherein the amount of said alkoxysilanes to be incorporated is not less than 1.4 wt % calculated as silicon based on the amount of said crystalline aluminosilicate. Because the specific catalyst has the narrowed or restricted entrances of the micro pores of the crystalline aluminosilicate by the alkoxysilane treatment, it is possible to prepare p-ethylphenol in a high selectivity. The product contains only a very small amount of m-ethylphenol. The p-ethylphenol product obtained by the process of the present invention can be employed directly as raw materials for practical uses such as synthetic resins and antioxidants without m-ethylphenol elimination procedure.
Inventors
- 👤 Takanori Yamagishi
- 👤 Tsutomu Idai
- 👤 Eiji Takahashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 00:18
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/16; B; B01; B01J; B01J29/00; B01J29/04; B01J29/06; B01J29/40; C07C37/14; B01J2229/00; B01J2229/10; B01J2229/26; B01J2229/30; B01J2229/36; B01J2229/42; B01J29/65; B01J29/70
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
172 words
In a process for the preparation of a mixture of ethylphenol isomers which comprises reacting phenol with an ethylating agent selected from the group consisting of ethylene and ethanol in the vapor phase in the presence of a catalyst at a temperature of 200°-600° C. under a pressure of not higher than 10 Kg/cm 2 .G, the improvement which comprises that said mixture of ethylphenol isomers has a p-ethylphenol content of higher than about 80 wt. % and said catalyst comprises a crystalline aluminosilicate catalyst obtained by incorporating one or more alkoxysilanes represented by the formula R' n Si(OR) 4-n wherein OR represents an alkoxy group having 1-6 carbon atoms, R' represents an alkyl group having 1-6 carbon atoms or a phenyl group and n represents an integer of 0-3, on a crystalline aluminosilicate having a constraint index of 1-15 and a silica/alumina molar ratio of 20-400, the amount of said incorporated alkoxysilanes being not less than 1.4 wt. % calculated as elemental silicon based on the amount of said crystalline aluminosilicate.
Claim 2
Dependent Claim
172 words
In a process for the preparation of a mixture of ethylphenol isomers which comprises reacting phenol with an ethylating agent selected from the group consisting of ethylene and ethanol in the vapor phase in the presence of a catalyst at a temperature of 200°-600° C. under a pressure of not higher than 10 Kg/cm 2 .G, the improvement which comprises that said mixture of ethylphenol isomers has a p-ethylphenol content of higher than about 80 wt. % and said catalyst comprises a crystalline aluminosilicate catalyst obtained by incorporating one or more alkoxysilanes represented by the formula R' n Si(OR) 4-n wherein OR represents an alkoxy group having 1-6 carbon atoms, R' represents an alkyl group having 1-6 carbon atoms or a phenyl group and n represents an integer of 0-3, on a crystalline aluminosilicate having a constraint index of 1-15 and a silica/alumina molar ratio of 20-400, the amount of said incorporated alkoxysilanes being not less than 1.4 wt. % calculated as elemental silicon based on the amount of said crystalline aluminosilicate.
Claim 3
Dependent Claim
25 words
The process according to claim 1, wherein said crystalline aluminosilicate is a zeolite selected from the group consisting of ZSM-5, ZSM-11, ZSM-12, ZSM-35 and ZSM-38.
Claim 4
Dependent Claim
14 words
The process according to claim 1, wherein said crystalline aluminosilicate is a pentasil-type zeolite.
Claim 5
Dependent Claim
14 words
The process according to claim 3, wherein said pentasil-type zeolite is ZSM-5 or ZSM-11.
Claim 6
Dependent Claim
14 words
The process according to claim 1, wherein said crystalline aluminosilicate is an H-crystalline aluminosilicate.
Claim 7
Dependent Claim
43 words
The process according to claim 5, wherein said H-crystalline aluminosilicate is obtained by treating a crystalline aluminosilicate with an aqueous solution of one or more ammonium salts and then calcining thereby converting exchangeable cations positioned near the aluminum atoms into H + ions.
Claim 8
Dependent Claim
36 words
The process according to claim 1, wherein said alkoxy group of said alkoxysilane is a methoxy group or an ethoxy group and said alkyl group of said alkoxysilane is a methyl group or an ethyl group.
Claim 9
Dependent Claim
29 words
The process according to claim 1, wherein the weight hourly space velocity (WHSV) calculated in the total of said phenol and said ethylating agent is 0.2-160 hr -1 .
Claim 10
Dependent Claim
19 words
The process according to claim 1, wherein said catalyst is prepared by calcining after the incorporation of said alkoxysilanes.
Claim 11
Dependent Claim
19 words
The process according to claim 1, wherein said catalyst is prepared without calcination after the incorporation of said alkoxysilanes.
Claim 12
Dependent Claim
21 words
The process according to claim 1, wherein the molar ratio of said phenol to said ethylating agent (phenol/ethylating agent) is 0.1-20.
Claim 13
Dependent Claim
20 words
The process according to claim 1, wherein said phenol and said ethylating agent are reacted in the presence of steam.
Claim 14
Dependent Claim
19 words
The process according to claim 12, wherein the molar ratio of said steam to said phenol (steam/phenol) is 0.05-50.
Claim 15
Dependent Claim
23 words
The process according to claim 13, wherein the ethylating agent is ethylene and the molar ratio of phenol to ethylene (phenol/ethylene) is 0.1-20.
Claim 16
Dependent Claim
12 words
The process according to claim 11, wherein said ethylating agent is ethanol.
Claim 17
Dependent Claim
43 words
The process according to claim 4, wherein said crystalline aluminosilicate is an H-crystalline alumino-silicate and in the ethylating reaction the weight hourly space velocity is 0.2-160 hr -1 and a molar ratio of said phenol to said ethylating agent (phenol/ethylating agent) is 0.1-20.
Claim 18
Dependent Claim
43 words
The process according to claim 16, wherein said H-crystalline aluminosilicate is obtained by treating a crystalline aluminosilicate with an aqueous solution of one or more ammonium salts and then calcining thereby converting exchangeable cations positioned near the aluminum atoms into H + ions.
Claim 19
Dependent Claim
13 words
The process according to claim 17, wherein said alkoxysilane is tetramethoxysilane or tetraethoxysilane.
Claim 20
Dependent Claim
34 words
The process according to claim 18, wherein said ethylating agent is ethylene and said ethylating reaction is conducted in the presence of steam in an amount of 0.05-50 moles per 1 mole of phenol.
Claim 21
Dependent Claim
21 words
The process according to claim 1, wherein the p-ethylphenol content of said mixture of ethylphenol isomers is in excess of 90%.
References Cited (Backward Citations)
SU352868A1
Cited
US3706807A
Cited
US3728408A
Cited
US3702886A
Cited
US3709979A
Cited
US3832449A
Cited
US4016245A
Cited
US4046859A
Cited
SU692825A1
Cited
US4371714A
Cited
US4391998A
Cited
JPS59155331A
Cited
JPS59155332A
Cited
US4532368A
Cited
JPS60181042A
Cited
JPS6150933A
Cited
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