JPH04288026A - Production of alkyl-substituted aromatic compound - Google Patents
Production of alkyl-substituted aromatic compoundInfo
- Publication number
- JPH04288026A JPH04288026A JP3049711A JP4971191A JPH04288026A JP H04288026 A JPH04288026 A JP H04288026A JP 3049711 A JP3049711 A JP 3049711A JP 4971191 A JP4971191 A JP 4971191A JP H04288026 A JPH04288026 A JP H04288026A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aromatic compound
- substituted aromatic
- naphthalene
- reaction
- 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.)
- Granted
Links
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- 239000002168 alkylating agent Substances 0.000 claims abstract description 16
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 230000000737 periodic effect Effects 0.000 claims abstract description 8
- 230000002152 alkylating effect Effects 0.000 claims abstract description 5
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims description 7
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 6
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- 239000003054 catalyst Substances 0.000 abstract description 15
- 150000002790 naphthalenes Chemical class 0.000 abstract description 5
- 150000001336 alkenes Chemical class 0.000 abstract description 4
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 9
- 238000005804 alkylation reaction Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 4
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 4
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052914 metal silicate Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- UUCHLIAGHZJJER-UHFFFAOYSA-N 1,2-diethylnaphthalene Chemical class C1=CC=CC2=C(CC)C(CC)=CC=C21 UUCHLIAGHZJJER-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical class C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- OHJWSORLJAKJEK-UHFFFAOYSA-N 1,3,6-trimethylnaphthalene Chemical compound CC1=CC(C)=CC2=CC(C)=CC=C21 OHJWSORLJAKJEK-UHFFFAOYSA-N 0.000 description 2
- SDDBCEWUYXVGCQ-UHFFFAOYSA-N 1,5-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1C SDDBCEWUYXVGCQ-UHFFFAOYSA-N 0.000 description 2
- CBMXCNPQDUJNHT-UHFFFAOYSA-N 1,6-dimethylnaphthalene Chemical compound CC1=CC=CC2=CC(C)=CC=C21 CBMXCNPQDUJNHT-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- FEWANSQOXSIFOK-UHFFFAOYSA-N 1,2,3,4-tetraethylbenzene Chemical compound CCC1=CC=C(CC)C(CC)=C1CC FEWANSQOXSIFOK-UHFFFAOYSA-N 0.000 description 1
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 1
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- RQHPYGROUIBUSW-UHFFFAOYSA-N 1,2,3-trimethylnaphthalene Chemical class C1=CC=C2C(C)=C(C)C(C)=CC2=C1 RQHPYGROUIBUSW-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- LMQUSNYESBRWGV-UHFFFAOYSA-N 1,2-diethyl-3,4,5-trimethylnaphthalene Chemical compound CC1=CC=CC2=C(CC)C(CC)=C(C)C(C)=C21 LMQUSNYESBRWGV-UHFFFAOYSA-N 0.000 description 1
- WYGGNKBHGUNXNL-UHFFFAOYSA-N 1,2-diethyl-3,4-di(propan-2-yl)naphthalene Chemical compound C1=CC=C2C(C(C)C)=C(C(C)C)C(CC)=C(CC)C2=C1 WYGGNKBHGUNXNL-UHFFFAOYSA-N 0.000 description 1
- PYZHPQYQJAZUDA-UHFFFAOYSA-N 1,2-diethyl-3,4-dimethylnaphthalene Chemical compound C1=CC=CC2=C(CC)C(CC)=C(C)C(C)=C21 PYZHPQYQJAZUDA-UHFFFAOYSA-N 0.000 description 1
- XAUNXIRTHFROSP-UHFFFAOYSA-N 1,2-diethyl-3-methylnaphthalene Chemical compound C1=CC=CC2=C(CC)C(CC)=C(C)C=C21 XAUNXIRTHFROSP-UHFFFAOYSA-N 0.000 description 1
- LVBVOKHNALCUAC-UHFFFAOYSA-N 1,2-dimethyl-3,4-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=C(C)C(C)=C21 LVBVOKHNALCUAC-UHFFFAOYSA-N 0.000 description 1
- PDUBTFQVAPDGIY-UHFFFAOYSA-N 1-ethyl-2,3,4-trimethylnaphthalene Chemical compound C1=CC=C2C(CC)=C(C)C(C)=C(C)C2=C1 PDUBTFQVAPDGIY-UHFFFAOYSA-N 0.000 description 1
- VXCTVWRTENGZSU-UHFFFAOYSA-N 1-ethyl-2,3-dimethylnaphthalene Chemical compound C1=CC=C2C(CC)=C(C)C(C)=CC2=C1 VXCTVWRTENGZSU-UHFFFAOYSA-N 0.000 description 1
- INUWBHWKAMVTNU-UHFFFAOYSA-N 1-ethyl-2-methylnaphthalene Chemical compound C1=CC=C2C(CC)=C(C)C=CC2=C1 INUWBHWKAMVTNU-UHFFFAOYSA-N 0.000 description 1
- MANLJMLXDBLEMZ-UHFFFAOYSA-N 2,3-diethyl-1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=C(CC)C(CC)=CC2=C1 MANLJMLXDBLEMZ-UHFFFAOYSA-N 0.000 description 1
- SCHHNCZIQBZPMA-UHFFFAOYSA-N 2,3-diethylnaphthalene Chemical compound C1=CC=C2C=C(CC)C(CC)=CC2=C1 SCHHNCZIQBZPMA-UHFFFAOYSA-N 0.000 description 1
- CJJFFBINNGWEBO-UHFFFAOYSA-N 2,6-diethylnaphthalene Chemical compound C1=C(CC)C=CC2=CC(CC)=CC=C21 CJJFFBINNGWEBO-UHFFFAOYSA-N 0.000 description 1
- PEPZWQMTUCWVFP-UHFFFAOYSA-N 2-ethyl-1-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(CC)=CC=C21 PEPZWQMTUCWVFP-UHFFFAOYSA-N 0.000 description 1
- QXGRHDNPJDFJSR-UHFFFAOYSA-N 2-methyl-1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=C(C)C=CC2=C1 QXGRHDNPJDFJSR-UHFFFAOYSA-N 0.000 description 1
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 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
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、アルキル置換芳香族化
合物の製造方法に関し、詳しくは、ナフタレンやアルキ
ル置換ナフタレン類のような原料芳香族化合物をアルキ
ル化剤にてアルキル化する際に、触媒としてケイタング
ステン酸金属塩を用いて、温和な条件下に高選択率にて
アルキル化置換芳香族化合物を得る方法に関する。[Industrial Application Field] The present invention relates to a method for producing an alkyl-substituted aromatic compound, and more specifically, when a raw material aromatic compound such as naphthalene or alkyl-substituted naphthalenes is alkylated with an alkylating agent, a catalyst is used. This invention relates to a method for obtaining alkylated substituted aromatic compounds with high selectivity under mild conditions using a metal tungstate silicate.
【０００２】0002
【従来の技術】アルキル置換芳香族化合物は、重合体や
医薬品を製造するための中間体として有用である。かか
るアルキル置換芳香族化合物の製造方法としては、従来
、無水塩化アルミニウムを触媒として、芳香族化合物を
液相反応にてアルキル化するフリーデル・クラフツ反応
や、固体シリカアルミナ触媒を用いる気相反応等が知ら
れている。BACKGROUND OF THE INVENTION Alkyl-substituted aromatic compounds are useful as intermediates for producing polymers and pharmaceuticals. Conventional methods for producing such alkyl-substituted aromatic compounds include the Friedel-Crafts reaction in which an aromatic compound is alkylated in a liquid phase reaction using anhydrous aluminum chloride as a catalyst, and the gas phase reaction using a solid silica alumina catalyst. It has been known.
【０００３】しかしながら、フリーデル・クラフツ反応
による場合は、一般に、高沸点化合物が副生物として大
量に生成するので、目的とするアルキル置換芳香族化合
物を収率よく得ることができない。他方、固体シリカア
ルミナ触媒を用いる気相反応による場合は、高温を必要
とし、しかも、多様な副反応が生じるので、同様に目的
物の収率が低い。However, in the case of Friedel-Crafts reaction, a large amount of high-boiling compounds are generally produced as by-products, so that the target alkyl-substituted aromatic compound cannot be obtained in good yield. On the other hand, when using a gas phase reaction using a solid silica alumina catalyst, high temperatures are required and various side reactions occur, so the yield of the target product is similarly low.
【０００４】0004
【発明が解決しようとする課題】発明は、従来のアルキ
ル置換芳香族化合物の製造における上記した問題を解決
するためになされたものであつて、特に、温和な反応条
件下に高沸点副生物の生成を抑制しつつ、ナフタレン類
やアルキルナフタレン類のような芳香族化合物を触媒の
存在下にアルキル化剤にてアルキル化して、アルキル置
換芳香族化合物を製造することができる方法を提供する
ことを目的とする。SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems in the conventional production of alkyl-substituted aromatic compounds. To provide a method for producing an alkyl-substituted aromatic compound by alkylating an aromatic compound such as naphthalenes or alkylnaphthalenes with an alkylating agent in the presence of a catalyst while suppressing the formation. purpose.
【０００５】[0005]
【０００６】本発明によるアルキル置換芳香族化合物の
製造方法は、The method for producing an alkyl-substituted aromatic compound according to the present invention includes:
【化１】[Chemical formula 1]
【０００７】（式中、Ｍは周期律表第Ｉａ族金属を示し
、ｘは０．５〜２．８の数を示す。）で表わされるケイ
タングステン酸金属塩の存在下に芳香族化合物をアルキ
ル化剤にてアルキル化することを特徴とする。本発明の
方法は、芳香核にアルキル化の対象となる置換位置を有
するものであれば、単環式、多環式、縮合環式等のいず
れの芳香族化合物でもよく、ベンゼンのような単環式の
もの、ビフェニル、ジフェニルメタンのような多環式の
もの、ナフタレン、アントラセンのような縮合環式のも
の、これらの化合物の芳香環上に一つ又は複数のアルキ
ル基を有するもの、これらの組合わせとしての種々の置
換芳香族化合物に適用することができる。[0007] An aromatic compound is prepared in the presence of a metal silicate tungstate represented by the following formula: It is characterized by alkylation with an alkylating agent. The method of the present invention can be applied to any aromatic compound, such as monocyclic, polycyclic, or condensed ring, as long as the aromatic nucleus has a substitution position to be alkylated. cyclic compounds, polycyclic compounds such as biphenyl and diphenylmethane, fused cyclic compounds such as naphthalene and anthracene, and compounds having one or more alkyl groups on the aromatic ring of these compounds; It can be applied to various substituted aromatic compounds as a combination.
【０００８】しかし、本発明の方法は、温和な反応条件
下でのアルキル化の選択性にすぐれるところから、従来
、知られている方法に比べて、特に、ナフタレン類のア
ルキル化によるアルキルナフタレン類の製造に好ましく
用いることができる。かかるナフタレン類としては、例
えば、ナフタレンのほか、１−メチルナフタレン、２−
メチルナフタレン等のメチルナフタレン類、１，５−ジ
メチルナフタレン、１，６−ジメチルナフタレン等のジ
メチルナフタレン類、１−エチルナフタレン、２−エチ
ルナフタレン等のジエチルナフタレン類、２，６−ジエ
チルナフタレン、２，３−ジエチルナフタレン等のジエ
チルナフタレン類、１，３，６−トリメチルナフタレン
等のトリメチルナフタレン類、１−イソプロピルナフタ
レン、２−イソプロピルナフタレン等のイソプロピルナ
フタレン類、メチルエチルナフタレン、メチルイソプロ
ピルナフタレン、エチルイソプロピルナフタレン、ジメ
チルエチルナフタレン、メチルジエチルナフタレン、ジ
メチルジエチルナフタレン、ジメチルジイソプロピルナ
フタレン、トリメチルエチルナフタレン、トリメチルジ
エチルナフタレン、ジエチルイソプロピルナフタレン、
ジエチルジイソプロピルナフタレン等の混合アルキルナ
フタレン類を挙げることができる。However, the method of the present invention has superior alkylation selectivity under mild reaction conditions, and therefore is more effective than conventionally known methods, particularly in the production of alkylnaphthalenes by alkylating naphthalenes. It can be preferably used in the production of products such as Examples of such naphthalenes include naphthalene, 1-methylnaphthalene, and 2-methylnaphthalene.
Methylnaphthalenes such as methylnaphthalene, dimethylnaphthalenes such as 1,5-dimethylnaphthalene and 1,6-dimethylnaphthalene, diethylnaphthalenes such as 1-ethylnaphthalene and 2-ethylnaphthalene, 2,6-diethylnaphthalene, 2 , 3-diethylnaphthalene and other diethylnaphthalenes, 1,3,6-trimethylnaphthalene and other trimethylnaphthalenes, 1-isopropylnaphthalene and 2-isopropylnaphthalene and other isopropylnaphthalenes, methylethylnaphthalene, methylisopropylnaphthalene, ethylisopropyl Naphthalene, dimethylethylnaphthalene, methyldiethylnaphthalene, dimethyldiethylnaphthalene, dimethyldiisopropylnaphthalene, trimethylethylnaphthalene, trimethyldiethylnaphthalene, diethylisopropylnaphthalene,
Mention may be made of mixed alkylnaphthalenes such as diethyldiisopropylnaphthalene.
【０００９】これらのなかでも、本発明においては、特
に、ナフタレンのほか、メチル基、エチル基及びイソプ
ロピル基から選ばれる一つ又は二つのアルキル基を有す
るモノ又はジアルキルナフタレン類が好ましく用いられ
る。具体的には、例えば、ナフタレンのほか、メチルナ
フタレン類、エチルナフタレン類、ジメチルナフタレン
類、イソプロピルナフタレン類等を挙げることができる
。Among these, mono- or dialkylnaphthalenes having one or two alkyl groups selected from naphthalene, methyl group, ethyl group and isopropyl group are particularly preferably used in the present invention. Specifically, in addition to naphthalene, methylnaphthalenes, ethylnaphthalenes, dimethylnaphthalenes, isopropylnaphthalenes, and the like can be mentioned.
【００１０】本発明の方法においては、アルキル化剤と
しては、例えば、エチレンやプロピレン等のα−オレフ
ィン類、エタノールやイソプロピルアルコール等の脂肪
族低級アルコール類、エチルエーテルやイソプロピルエ
ーテル等の低級アルキルエーテル類、酢酸エチルや酢酸
イソプロピル等の酢酸低級アルキルエステル類、塩化メ
チルや塩化イソプロピル等のハロゲン化アルキル類、特
に、塩化低級アルキル類等、一般にアルキル化反応に用
いらているアルキル化剤や、更には、ジエチルベンゼン
、トリエチルベンゼン、テトラエチルベンゼン、ジイソ
プロピルベンゼン、トリイソプロピルベンゼン、テトラ
イソプロピルベンゼン等のポリアルキルベンゼン、これ
らの混合物等、トランスアルキル化反応に用いられてい
るアルキル化剤等が用いられる。In the method of the present invention, examples of alkylating agents include α-olefins such as ethylene and propylene, aliphatic lower alcohols such as ethanol and isopropyl alcohol, and lower alkyl ethers such as ethyl ether and isopropyl ether. alkylating agents commonly used in alkylation reactions, such as acetic acid lower alkyl esters such as ethyl acetate and isopropyl acetate, alkyl halides such as methyl chloride and isopropyl chloride, and especially lower alkyl chlorides; Examples of alkylating agents used in transalkylation reactions include polyalkylbenzenes such as diethylbenzene, triethylbenzene, tetraethylbenzene, diisopropylbenzene, triisopropylbenzene, and tetraisopropylbenzene, and mixtures thereof.
【００１１】本発明の方法においては、触媒として、[0011] In the method of the present invention, as a catalyst,
【
化１】[
Chemical 1]
【００１２】（式中、Ｍは周期律表第Ｉａ族金属を示し
、ｘは０．５〜２．８の数を示す。）で表わされるケイ
タングステン酸金属塩が用いられる。即ち、かかるケイ
タングステン酸金属塩は、ケイタングステン酸の水素が
周期律表第Ｉａ族金属の少なくとも１種で交換されてな
る金属塩であつて、かかる周期律表第Ｉａ族金属は、好
ましくはカリウム、ルビジウム又はセシウムである。ケ
イタングステン酸の水素は、複数の金属によつて複合的
に交換されていてもよい。特に、上記式において、ｘは
１．０〜２．５の範囲の数であることが好ましい。尚、
上記のようなケイタングステン酸金属塩は、一般に、結
晶水を含むが、本明細書においては、結晶水の記載は省
略されている。A metal silicate tungstate represented by the formula (wherein M represents a metal of Group Ia of the periodic table, and x represents a number from 0.5 to 2.8) is used. That is, the metal salt of tungstate silicate is a metal salt obtained by replacing the hydrogen of tungstic acid with at least one metal of group Ia of the periodic table, and the metal of group Ia of the periodic table is preferably Potassium, rubidium or cesium. Hydrogen in silicotungstic acid may be exchanged in a complex manner by a plurality of metals. In particular, in the above formula, x is preferably a number in the range of 1.0 to 2.5. still,
Although the above metal silicic acid salts generally contain water of crystallization, the description of water of crystallization is omitted in this specification.
【００１３】かかるケイタングステン酸金属塩は、計算
量の周期律表第Ｉａ族金属の炭酸塩をケイタングステン
酸の水溶液に攪拌下に加えた後、５０℃で蒸発乾固させ
ればよい。このようなケイタングステン酸の金属塩は、
（無水物換算で）通常、原料である芳香族化合物に対し
て、重量比で０．０００１〜０．５の範囲で用いられる
。[0013] Such a metal silicate tungstate can be obtained by adding a calculated amount of a carbonate of a Group Ia metal of the periodic table to an aqueous solution of tungstic acid silico with stirring, and then evaporating the mixture to dryness at 50°C. Such metal salts of tungstic acid are
It is usually used in a weight ratio of 0.0001 to 0.5 (in terms of anhydride) relative to the aromatic compound that is the raw material.
【００１４】本発明においては、反応は、流通反応形式
やバッチ反応形式等、どのような形式にても行なうこと
ができる。また、反応条件は、原料として用いる芳香族
化合物やアルキル化剤の種類等によつて適宜に選択され
るが、例えば、アルキル化剤としてオレフィン類が用い
られるときは、反応は、通常、溶媒の存在下又は不存在
下に液相加圧下に行なわれる。反応溶媒を用いるときは
、例えば、デカリン、シクロドデカン、ヘキサン、ヘプ
タン、オクタン、ノナン、デカン、ウンデカン、ドデカ
ン等の飽和炭化水素溶媒が好ましく用いられる。また、
反応温度は、通常、１００〜３００℃、好ましくは１５
０〜２５０℃であり、反応圧力（オレフィン圧力）は、
通常、１〜５００Ｋｇ／平方センチメートルＧ、好まし
くは１〜３００Ｋｇ／平方センチメートルＧである。In the present invention, the reaction can be carried out in any format such as a flow reaction format or a batch reaction format. In addition, reaction conditions are appropriately selected depending on the aromatic compound used as a raw material and the type of alkylating agent. For example, when olefins are used as an alkylating agent, the reaction is usually It is carried out under liquid phase pressure in the presence or absence. When using a reaction solvent, for example, saturated hydrocarbon solvents such as decalin, cyclododecane, hexane, heptane, octane, nonane, decane, undecane, and dodecane are preferably used. Also,
The reaction temperature is usually 100 to 300°C, preferably 15°C.
The temperature is 0 to 250°C, and the reaction pressure (olefin pressure) is
Usually, it is 1 to 500 kg/cm2 G, preferably 1 to 300 kg/cm2 G.
【００１５】本発明において用いる前記ケイタングステ
ン酸の金属塩は水溶性であるので、反応終了後、得られ
た反応混合物から水で抽出することによつて、容易に分
離することができる。従つて、反応終了後、上記のよう
にしてケイタングステン酸の金属塩を水抽出し、蒸発、
乾固させることによつて、再利用することができる。他
方、リンタングステン酸の水素を一部、カリウムのよう
な周期律表Ｉａ金属で交換した金属塩は水に不溶性であ
る。このような触媒は、反応に用いた場合、これにター
ル等が付着したときは、触媒を回収し、再使用すること
が困難である。Since the metal salt of tungstic acid silico used in the present invention is water-soluble, it can be easily separated by extraction with water from the reaction mixture obtained after the reaction is completed. Therefore, after the reaction is completed, the metal salt of silicotungstic acid is extracted with water as described above, and evaporated.
It can be reused by drying. On the other hand, metal salts in which part of the hydrogen of phosphotungstic acid is replaced by a Periodic Table Ia metal such as potassium are insoluble in water. When such a catalyst is used in a reaction and tar etc. adhere to it, it is difficult to recover and reuse the catalyst.
【００１６】また、本発明において、上記のような液相
反応にて反応を行なつた後、得られた反応混合物から触
媒を除去し、溶媒を留去すれば、目的とするアルキル置
換芳香族化合物を得ることができる。このアルキル置換
芳香族化合物は、必要に応じて、蒸留、抽出、再結晶等
の方法によつて、更に処理される。Further, in the present invention, after carrying out the reaction in the liquid phase as described above, by removing the catalyst from the obtained reaction mixture and distilling off the solvent, the desired alkyl-substituted aromatic compound can be obtained. compound can be obtained. This alkyl-substituted aromatic compound is further processed, if necessary, by methods such as distillation, extraction, and recrystallization.
【００１７】[0017]
【発明の効果】以上のように、本発明の方法によれば、
アルキル化剤を用いて芳香族化合物をアルキル化するア
ルキル置換芳香族化合物の製造において、触媒として、
前述したケイタングステン酸金属塩を用いることによつ
て、原料である芳香族化合物や、或いは特にアルキル化
剤であるオレフィン類の副反応を抑制しつつ、温和な反
応条件下に目的とするアルキル化を高選択性にて行なつ
て、高収率にて目的とするアルキル置換芳香族化合物を
得ることができる。[Effects of the Invention] As described above, according to the method of the present invention,
In the production of alkyl-substituted aromatic compounds by alkylating aromatic compounds using an alkylating agent, as a catalyst,
By using the aforementioned tungstate metal salt, the desired alkylation can be carried out under mild reaction conditions while suppressing side reactions of aromatic compounds as raw materials or olefins as alkylating agents. By performing this with high selectivity, the desired alkyl-substituted aromatic compound can be obtained in high yield.
【００１８】[0018]
【実施例】以下に実施例を挙げて本発明を説明するが、
本発明はこれら実施例により何ら限定されるものではな
い。表において、アルキル化反応選択率は、原料がモノ
、ジ、トリ及びテトラアルキル化された生成物の選択率
の合計を意味し、また、触媒は、結晶水を省略して記載
されている。
実施例１
内容積５０ｍｌのオートクレーブにナフタレン（川崎製
鉄製精製ナフタレン）１０ｇとデカン１０ｍｌとを表１
に示す組成のケイタングステン酸カリウム塩８５０ｍｇ
と共に仕込み、オートクレーブを密閉した後、エチレン
ガスで置換し、エチレン圧力３０Ｋｇ／平方センチメー
トルＧ、温度２００℃の条件下に攪拌下、２時間反応さ
せた。反応終了後、触媒を濾別し、得られた反応混合物
について、その組成をガスクロマトグラフィーにて分析
した。
結果を表１に示す。
実施例２
表１に示す組成のケイタングステン酸カリウム塩を用い
た以外は、実施例１と同様に処理した。結果を表１に示
す。
実施例３
表１に示す組成のケイタングステン酸カリウム塩１０ｍ
ｇを用い、更に、反応温度を２６０℃とした以外は、実
施例１と同様に処理した。結果を表１に示す。
実施例４
原料として２−エチルナフタレン１０ｇと表１に示す組
成のケイタングステン酸カリウム塩１００ｍｇを用いる
と共に、反応温度を２００℃とした以外は、実施例１と
同様に処理した。結果を表１に示す。
実施例５
表１に示す組成のケイタングステン酸セシウム塩２００
ｍｇを用いた以外は、実施例１と同様に処理した。結果
を表１に示す。
実施例６
アルキル化剤としてプロピレンを用い、触媒として表１
に示す組成のケイタングステン酸カリウム塩２００ｍｇ
を用いると共に、反応温度を１７０℃とした以外は、実
施例と同様に処理した。結果を表１に示す。
比較例１〜５
表１に示す触媒を用いて、表１に示す反応条件下に反応
を行なつた以外は、実施例と同様に処理した。結果を表
１に示す。[Examples] The present invention will be explained below with reference to Examples.
The present invention is not limited in any way by these Examples. In the table, the alkylation reaction selectivity means the sum of the selectivities of products obtained by mono-, di-, tri-, and tetra-alkylation of the raw materials, and the catalyst is described without water of crystallization. Example 1 In an autoclave with an internal volume of 50 ml, 10 g of naphthalene (purified naphthalene manufactured by Kawasaki Steel Corporation) and 10 ml of decane were placed in Table 1.
850 mg of potassium tungstate silicate with the composition shown in
After the autoclave was sealed, the autoclave was replaced with ethylene gas, and the reaction was carried out for 2 hours under stirring at an ethylene pressure of 30 kg/cm2G and a temperature of 200°C. After the reaction was completed, the catalyst was filtered off, and the composition of the resulting reaction mixture was analyzed by gas chromatography. The results are shown in Table 1. Example 2 The same treatment as in Example 1 was carried out except that potassium silicotungstate having the composition shown in Table 1 was used. The results are shown in Table 1. Example 3 10 m of potassium tungstate silicate having the composition shown in Table 1
The process was carried out in the same manner as in Example 1, except that g was used and the reaction temperature was changed to 260°C. The results are shown in Table 1. Example 4 The same process as in Example 1 was carried out, except that 10 g of 2-ethylnaphthalene and 100 mg of potassium tungstate silicolate having the composition shown in Table 1 were used as raw materials, and the reaction temperature was 200°C. The results are shown in Table 1. Example 5 Cesium silicotungstate 200 having the composition shown in Table 1
The treatment was carried out in the same manner as in Example 1, except that mg was used. The results are shown in Table 1. Example 6 Propylene was used as the alkylating agent and Table 1 was used as the catalyst.
200 mg of potassium tungstate silicate with the composition shown in
The process was carried out in the same manner as in the example except that the reaction temperature was 170°C. The results are shown in Table 1. Comparative Examples 1 to 5 The same procedures as in Examples were carried out, except that the catalysts shown in Table 1 were used and the reactions were carried out under the reaction conditions shown in Table 1. The results are shown in Table 1.
【００１９】[0019]
【表１】[Table 1]
【００２０】以上のように、本発明の方法によれば、原
料の転化率が高く、しかも、アルキル化反応の選択率が
高い。As described above, according to the method of the present invention, the conversion rate of the raw material is high and the selectivity of the alkylation reaction is high.
Claims (5)
〜２．８の数を示す。）で表わされるケイタングステン
酸金属塩の存在下に芳香族化合物をアルキル化剤にてア
ルキル化することを特徴とするアルキル置換芳香族化合
物の製造方法。[Claim 1] [Chemical formula 1] (wherein M represents a Group Ia metal of the periodic table, x is 0.5
~2.8. ) A method for producing an alkyl-substituted aromatic compound, which comprises alkylating an aromatic compound with an alkylating agent in the presence of a metal salt of tungstate silicate.
ウム又はセシウムであることを特徴とする請求項１記載
のアルキル置換芳香族化合物の製造方法。2. The method for producing an alkyl-substituted aromatic compound according to claim 1, wherein the Group Ia metal of the periodic table is potassium, rubidium or cesium.
あることを特徴とする請求項１記載のアルキル置換芳香
族化合物の製造方法。3. The method for producing an alkyl-substituted aromatic compound according to claim 1, wherein the alkylating agent is ethylene or propylene.
フタレン類であることを特徴とする請求項１記載のアル
キル置換芳香族化合物の製造方法。4. The method for producing an alkyl-substituted aromatic compound according to claim 1, wherein the aromatic compound is naphthalene or alkylnaphthalenes.
チルナフタレンであることを特徴とする請求項４記載の
アルキル置換芳香族化合物の製造方法。5. The method for producing an alkyl-substituted aromatic compound according to claim 4, wherein the alkylnaphthalene is naphthalene or ethylnaphthalene.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3049711A JP2975702B2 (en) | 1991-03-14 | 1991-03-14 | Method for producing alkyl-substituted aromatic compound |
| US07/773,264 US5254766A (en) | 1990-10-16 | 1991-10-09 | Process for producing alkyl-substituted aromatic hydrocarbon using heteropolyacid salts |
| AT91117298T ATE147715T1 (en) | 1990-10-16 | 1991-10-10 | METHOD FOR PRODUCING AN ALKYL-SUBSTITUTED HYDROCARBON |
| EP91117298A EP0481360B1 (en) | 1990-10-16 | 1991-10-10 | Process for producing alkyl-substituted aromatic hydrocarbon |
| DE69124182T DE69124182T2 (en) | 1990-10-16 | 1991-10-10 | Process for the preparation of an alkyl substituted hydrocarbon |
| KR1019910017919A KR950001674B1 (en) | 1990-10-16 | 1991-10-11 | Process for producing alkyl-substituted aromatic hydrocarbon |
| CA002053469A CA2053469C (en) | 1990-10-16 | 1991-10-15 | Process for producing alkyl-substituted aromatic hydrocarbon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3049711A JP2975702B2 (en) | 1991-03-14 | 1991-03-14 | Method for producing alkyl-substituted aromatic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04288026A true JPH04288026A (en) | 1992-10-13 |
| JP2975702B2 JP2975702B2 (en) | 1999-11-10 |
Family
ID=12838775
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| JP3049711A Expired - Fee Related JP2975702B2 (en) | 1990-10-16 | 1991-03-14 | Method for producing alkyl-substituted aromatic compound |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008290036A (en) * | 2006-05-29 | 2008-12-04 | Sumitomo Chemical Co Ltd | Heteropoly acid salt catalyst, method for producing heteropoly acid salt catalyst, and method for producing alkylaromatic compound |
| JP2009029800A (en) * | 2007-07-04 | 2009-02-12 | Sumitomo Chemical Co Ltd | Method for producing alkyl aromatic compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61280439A (en) * | 1985-05-13 | 1986-12-11 | Idemitsu Kosan Co Ltd | Production of alkenyl aromatic hydrocarbon derivative |
| JPS62255440A (en) * | 1986-04-25 | 1987-11-07 | Res Assoc Util Of Light Oil | Production of ethylbenzene |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008290036A (en) * | 2006-05-29 | 2008-12-04 | Sumitomo Chemical Co Ltd | Heteropoly acid salt catalyst, method for producing heteropoly acid salt catalyst, and method for producing alkylaromatic compound |
| JP2009029800A (en) * | 2007-07-04 | 2009-02-12 | Sumitomo Chemical Co Ltd | Method for producing alkyl aromatic compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2975702B2 (en) | 1999-11-10 |
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