US4520219A
Expired / Lapsed
US
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Process for the production of pseudocumene or durene
Assignee: Idemitsu Kosan Co Ltd
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Filing: 1983-09-14
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Granted: 1985-05-28
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Expires: 2003-09-14
Abstract
Abstract A process for producing pseudocueme or durene is described, comprising methylating xylene by the use as a catalyst of at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate. The specific crystalline silicate catalyst increases the conversion of xylene and the selectivity of pseudocumene or durene. The process of the invention can be performed either in one step or in two steps. The two-step reaction provides various industrial advantages, such as a high degree of utilization of the methylating agent and a great increase in the selectivity of the product.
Inventors
- 👤 Haruhito Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 05:42
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/86; C07C2/862; C07C2/864; C07C2/865; C07C2521/00; C07C2521/02; C07C2521/06; C07C2521/08; C07C2529/00; C07C2529/86
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
230 words
A process for producing at least one of pseudocumene and durene comprising reacting xylene and a methylating agent in the presence of a catalyst, which is at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate; said fluorine-containing crystalline borosilicate being prepared by contacting crystalline borosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, said fluorine-containing crystalline aluminosilicate being prepared by contacting crystalline aluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, and said fluorine-containing crystalline boroaluminosilicate being prepared by contacting crystalline boroaluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl.
Claim 2
Dependent Claim
230 words
A process for producing at least one of pseudocumene and durene comprising reacting xylene and a methylating agent in the presence of a catalyst, which is at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate; said fluorine-containing crystalline borosilicate being prepared by contacting crystalline borosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, said fluorine-containing crystalline aluminosilicate being prepared by contacting crystalline aluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, and said fluorine-containing crystalline boroaluminosilicate being prepared by contacting crystalline boroaluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl.
Claim 3
Dependent Claim
22 words
The process of claim 1, wherein the methylating agent is selected from the group consisting of methanol, dimethyl ether, methylchloride and methylbromide.
Claim 4
Dependent Claim
14 words
The process of claim 2, wherein the methylating agent is methanol or dimethyl ether.
Claim 5
Dependent Claim
47 words
The process of claim 1, which comprises reacting xylene and a first methylating agent in the presence of said catalyst to thereby obtain a reaction mixture and reacting at least a part of the reaction mixture with a second methylating agent in the presence of said catalyst.
Claim 6
Dependent Claim
19 words
The process of claim 4, wherein said methylating agent is dimethyl ether and said second methylating agent is methanol.
Claim 7
Dependent Claim
17 words
The process of claim 4, further comprising recovering at least a portion of said second methylating agent.
Claim 8
Dependent Claim
17 words
The process of claim 6, further comprising employing said recovered methylating agent as said first methylating agent.
Claim 9
Dependent Claim
19 words
The process of claim 1, wherein the molar ratio of xylene to said methylating agent is 20:1 to 1:20.
Claim 10
Dependent Claim
19 words
The process of claim 8, wherein the molar ratio of xylene to said methylating agent is 5:1 to 1:5.
Claim 11
Dependent Claim
25 words
The process of claim 1, wherein said catalyst is selected from the group consisting of fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate and fluorine-containing crystalline boroaluminosilicate.
Claim 12
Dependent Claim
11 words
The process of claim 1, wherein said catalyst is crystalline borosilicate.
Claim 13
Dependent Claim
30 words
The process of claim 1, wherein the reaction is conducted at a temperature of 200° to 700° C. and a pressure of from atmospheric pressure to 100 kg/cm 2 .G.
Claim 14
Dependent Claim
223 words
A process for producing pseudocumene or durene comprising reacting toluene and a methylating agent in the presence of a catalyst, which is at least one crystalline silicate selected from the group consisting of fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate; said fluorine-containing crystalline borosilicate being prepared by contacting crystalline borosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, said fluorine-containing crystalline aluminosilicate being prepared by contacting crystalline aluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, and said fluorine-containing crystalline boroaluminosilicate being prepared by contacting crystalline boroaluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl.
Claim 15
Dependent Claim
223 words
A process for producing pseudocumene or durene comprising reacting toluene and a methylating agent in the presence of a catalyst, which is at least one crystalline silicate selected from the group consisting of fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate; said fluorine-containing crystalline borosilicate being prepared by contacting crystalline borosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, said fluorine-containing crystalline aluminosilicate being prepared by contacting crystalline aluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, and said fluorine-containing crystalline boroaluminosilicate being prepared by contacting crystalline boroaluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl.
Claim 16
Dependent Claim
222 words
A process for producing durene comprising reacting pseudocumene and a methylating agent in the presence of a catalyst which is at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate; said fluorine-containing crystalline borosilicate being prepared by contacting crystalline borosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, said fluorine-containing crystalline aluminosilicate being prepared by contacting crystalline aluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, and said fluorine-containing crystalline boroaluminosilicate being prepared by contacting crystalline boroaluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl.
Claim 17
Dependent Claim
222 words
A process for producing durene comprising reacting pseudocumene and a methylating agent in the presence of a catalyst which is at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate; said fluorine-containing crystalline borosilicate being prepared by contacting crystalline borosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, said fluorine-containing crystalline aluminosilicate being prepared by contacting crystalline aluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 , CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl, and said fluorine-containing crystalline boroaluminosilicate being prepared by contacting crystalline boroaluminosilicate with at least one fluorine-containing compound selected from the group consisting of HF, NH 4 F, NaF, BF 3 CFCl 3 , CF 2 Cl 2 , CF 3 Cl, CHFCl 2 , CHF 2 Cl, CHF 3 , CF 2 ClCFCl 2 and CF 2 ClCF 2 Cl.
Claim 18
Dependent Claim
46 words
The process of claim 14, which comprises reacting xylene and a first methylating agent in the presence of said catalyst to thereby obtain a reaction mixture and reacting at least part of the reaction mixture with a second methylating agent in the presence of said catalyst.
Claim 19
Dependent Claim
16 words
The process of claim 15, wherein each of said first and second methylating agent is methanol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-05-27 | 1988-11-26 | 1989-05-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-27 | 1992-11-26 | 1993-05-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-27 | 1996-11-26 | 1997-05-28 | $7700.00 | Window Closed / Lapsed |