JPS6253489B2 - - Google Patents
Info
- Publication number
- JPS6253489B2 JPS6253489B2 JP53050141A JP5014178A JPS6253489B2 JP S6253489 B2 JPS6253489 B2 JP S6253489B2 JP 53050141 A JP53050141 A JP 53050141A JP 5014178 A JP5014178 A JP 5014178A JP S6253489 B2 JPS6253489 B2 JP S6253489B2
- Authority
- JP
- Japan
- Prior art keywords
- xylene
- toluene
- whsv
- zeolite catalyst
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 60
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- 239000010457 zeolite Substances 0.000 claims description 21
- 229910021536 Zeolite Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- 239000012022 methylating agents Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 230000011987 methylation Effects 0.000 claims description 7
- 238000007069 methylation reaction Methods 0.000 claims description 7
- 230000001035 methylating effect Effects 0.000 claims description 5
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 1
- -1 C 15 olefin Chemical class 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940077445 dimethyl ether Drugs 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012021 ethylating agents Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5014178A JPS54144324A (en) | 1978-04-28 | 1978-04-28 | Manufacture of ppxylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5014178A JPS54144324A (en) | 1978-04-28 | 1978-04-28 | Manufacture of ppxylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54144324A JPS54144324A (en) | 1979-11-10 |
| JPS6253489B2 true JPS6253489B2 (es) | 1987-11-10 |
Family
ID=12850866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5014178A Granted JPS54144324A (en) | 1978-04-28 | 1978-04-28 | Manufacture of ppxylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54144324A (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288647A (en) * | 1980-03-10 | 1981-09-08 | Mobil Oil Corporation | Shape selective reactions with alkaline earth-modified zeolite catalysts |
| US4278827A (en) * | 1980-04-07 | 1981-07-14 | Mobil Oil Corporation | Shape selective reactions with zeolite catalyst modified with group IVB metal |
| EP0040463B1 (en) * | 1980-05-19 | 1984-09-05 | Mobil Oil Corporation | Shape selective reactions with zeolite catalyst modified with iron and/or cobalt |
| GB0303659D0 (en) | 2003-02-18 | 2003-03-19 | Johnson Matthey Plc | Process |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52139029A (en) * | 1976-05-17 | 1977-11-19 | Mobil Oil | Alkylation alkyl exchange reaction in the presence of crystalline aluminoslicate catalyst |
-
1978
- 1978-04-28 JP JP5014178A patent/JPS54144324A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52139029A (en) * | 1976-05-17 | 1977-11-19 | Mobil Oil | Alkylation alkyl exchange reaction in the presence of crystalline aluminoslicate catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54144324A (en) | 1979-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6217570B2 (es) | ||
| US4100217A (en) | Selective production of para-substituted benzenes | |
| CA2218869C (en) | Process of preparing ethylbenzene or substituted derivatives thereof | |
| US5227558A (en) | Aromatic alkylation process employing steam modified zeolite beta catalyst | |
| JP2656124B2 (ja) | βゼオライトを使用した液相アルキル化及びトランスアルキル化法 | |
| EP0137757A1 (en) | Alkylation of aromatic hydrocarbons | |
| JPS6217569B2 (es) | ||
| US4524055A (en) | Crystalline aluminosilicate zeolite and process for production thereof | |
| US4490570A (en) | Method for para selective alkylation employing silicalite catalysts | |
| US4599473A (en) | Process for para selective alkylation of aromatic hydrocarbons | |
| EP0068755B1 (en) | Treatment of zeolite catalysts to enhance para-selectivity | |
| JPS586244A (ja) | ゼオライト触媒のパラ選択性向上処理法 | |
| US4238630A (en) | Production of aromatic hydrocarbons | |
| JPS6238332B2 (es) | ||
| JPH0324456B2 (es) | ||
| JPS6253489B2 (es) | ||
| JPS607604B2 (ja) | パラ置換されたベンゼンの選択的製造方法 | |
| JPH0366293B2 (es) | ||
| US6204423B1 (en) | Catalytic composition for the preparation of long-chain alkylaromatic compounds | |
| EP0026030B1 (en) | Conversion of toluene over zeolite zsm-48 | |
| US3819736A (en) | Process for conversion of alkyl aromatic hydrocarbons | |
| CA1214449A (en) | Silica-modified catalyst and use for selective production of para-dialkyl substituted benzenes | |
| JPS6245849B2 (es) | ||
| CA1090315A (en) | Process for producing p-dialkyl substituted benzenes and catalyst therefor | |
| JPS5835130A (ja) | Ｐ−キシレンの製造法 |