CA1055964A - Process for the preparation of alkyltetralins - Google Patents
Process for the preparation of alkyltetralinsInfo
- Publication number
- CA1055964A CA1055964A CA230,704A CA230704A CA1055964A CA 1055964 A CA1055964 A CA 1055964A CA 230704 A CA230704 A CA 230704A CA 1055964 A CA1055964 A CA 1055964A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- reaction zone
- catalyst
- alkenylbenzene
- temperature
- 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
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 188
- 239000003054 catalyst Substances 0.000 claims abstract description 65
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 45
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 33
- 239000007791 liquid phase Substances 0.000 claims abstract description 21
- 230000002378 acidificating effect Effects 0.000 claims abstract description 15
- 238000004064 recycling Methods 0.000 claims abstract description 12
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 42
- 235000011007 phosphoric acid Nutrition 0.000 description 21
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 20
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- NKEQCTWCOZGWSY-ONEGZZNKSA-N 1-methyl-2-[(e)-pent-3-enyl]benzene Chemical compound C\C=C\CCC1=CC=CC=C1C NKEQCTWCOZGWSY-ONEGZZNKSA-N 0.000 description 13
- 238000006317 isomerization reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical class C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 11
- 229910052680 mordenite Inorganic materials 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 8
- 229910000149 boron phosphate Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- BMADLDGHUBLVMQ-UHFFFAOYSA-N 1,5-dimethyltetralin Chemical compound C1=CC=C2C(C)CCCC2=C1C BMADLDGHUBLVMQ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 7
- KWSOSNULPSERHY-UHFFFAOYSA-N 1,6-dimethyl-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC=C2C(C)CCCC2=C1 KWSOSNULPSERHY-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- LRQYSMQNJLZKPS-UHFFFAOYSA-N 2,7-dimethylnaphthalene Chemical class C1=CC(C)=CC2=CC(C)=CC=C21 LRQYSMQNJLZKPS-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011949 solid catalyst Substances 0.000 description 4
- -1 tri- Chemical class 0.000 description 4
- SOWYMNHXSCXNGN-UHFFFAOYSA-N 1,7-dimethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1=C(C)C=C2C(C)CCCC2=C1 SOWYMNHXSCXNGN-UHFFFAOYSA-N 0.000 description 3
- ABIPNDAVRBMCHV-UHFFFAOYSA-N 4,4-dimethyl-2,3-dihydro-1h-naphthalene Chemical compound C1=CC=C2C(C)(C)CCCC2=C1 ABIPNDAVRBMCHV-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 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
- KVNZVXVZQFTXNA-UHFFFAOYSA-N 1,8-dimethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC(C)=C2C(C)CCCC2=C1 KVNZVXVZQFTXNA-UHFFFAOYSA-N 0.000 description 2
- VRFKBBOWFOYOEY-UHFFFAOYSA-N 1-methyl-3-pent-3-enylbenzene Chemical compound CC=CCCC1=CC=CC(C)=C1 VRFKBBOWFOYOEY-UHFFFAOYSA-N 0.000 description 2
- SOAPJKOPHBEWOH-UHFFFAOYSA-N 2,7-dimethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1=C(C)C=C2CC(C)CCC2=C1 SOAPJKOPHBEWOH-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GLXIHKLBZUKOLW-NSCUHMNNSA-N [(e)-pent-3-enyl]benzene Chemical compound C\C=C\CCC1=CC=CC=C1 GLXIHKLBZUKOLW-NSCUHMNNSA-N 0.000 description 2
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 235000011128 aluminium sulphate Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RURREWSZSUQSNB-UHFFFAOYSA-N pent-4-enylbenzene Chemical compound C=CCCCC1=CC=CC=C1 RURREWSZSUQSNB-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KNQXALMJMHIHQH-UHFFFAOYSA-N 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(C)CCC(C)C2=C1 KNQXALMJMHIHQH-UHFFFAOYSA-N 0.000 description 1
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical class C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 1
- MAHOTQTWFPUVQK-UHFFFAOYSA-N 1-ethyl-2-hex-4-en-2-ylbenzene Chemical compound CCC1=CC=CC=C1C(C)CC=CC MAHOTQTWFPUVQK-UHFFFAOYSA-N 0.000 description 1
- NETQNSYTYLGOJN-UHFFFAOYSA-N 1-ethyl-2-hex-5-en-2-ylbenzene Chemical compound CCC1=CC=CC=C1C(C)CCC=C NETQNSYTYLGOJN-UHFFFAOYSA-N 0.000 description 1
- KRLQTXBKJMUYMD-UHFFFAOYSA-N 1-hex-3-enyl-2-methylbenzene Chemical compound CCC=CCCC1=CC=CC=C1C KRLQTXBKJMUYMD-UHFFFAOYSA-N 0.000 description 1
- LBKQYYRVBLCVHX-UHFFFAOYSA-N 1-hex-4-en-2-yl-4-methylbenzene Chemical compound CC=CCC(C)C1=CC=C(C)C=C1 LBKQYYRVBLCVHX-UHFFFAOYSA-N 0.000 description 1
- IWJQKRPKNOCREM-UHFFFAOYSA-N 1-hex-4-enyl-2-methylbenzene Chemical compound CC=CCCCC1=CC=CC=C1C IWJQKRPKNOCREM-UHFFFAOYSA-N 0.000 description 1
- MAUHXSLDMRIHLY-UHFFFAOYSA-N 1-methyl-2-pent-1-enylbenzene Chemical compound CCCC=CC1=CC=CC=C1C MAUHXSLDMRIHLY-UHFFFAOYSA-N 0.000 description 1
- AOZLFGNQSVVKNN-UHFFFAOYSA-N 1-methyl-2-pent-2-enylbenzene Chemical compound CCC=CCC1=CC=CC=C1C AOZLFGNQSVVKNN-UHFFFAOYSA-N 0.000 description 1
- HEFLAPWVCUEOGS-UHFFFAOYSA-N 1-methyl-3-pent-4-enylbenzene Chemical compound CC1=CC=CC(CCCC=C)=C1 HEFLAPWVCUEOGS-UHFFFAOYSA-N 0.000 description 1
- MUHKIWBIYGOXLC-UHFFFAOYSA-N 1-methyl-4-pent-3-enylbenzene Chemical compound CC=CCCC1=CC=C(C)C=C1 MUHKIWBIYGOXLC-UHFFFAOYSA-N 0.000 description 1
- QILGGMVPBQWAQA-UHFFFAOYSA-N 1-methyl-4-pent-4-enylbenzene Chemical compound CC1=CC=C(CCCC=C)C=C1 QILGGMVPBQWAQA-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- DXRBFZCGSZKZTL-UHFFFAOYSA-N 2,6-dimethyl-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC=C2CC(C)CCC2=C1 DXRBFZCGSZKZTL-UHFFFAOYSA-N 0.000 description 1
- OUCFBYVNDQNAHD-UHFFFAOYSA-N 2-(pent-4-enyl)toluene Chemical compound CC1=CC=CC=C1CCCC=C OUCFBYVNDQNAHD-UHFFFAOYSA-N 0.000 description 1
- 239000010963 304 stainless steel Substances 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 241001050985 Disco Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- KCWNHVWBZXEUQG-UHFFFAOYSA-N hept-4-en-2-ylbenzene Chemical compound CCC=CCC(C)C1=CC=CC=C1 KCWNHVWBZXEUQG-UHFFFAOYSA-N 0.000 description 1
- KPNLFQFVZPTZGH-UHFFFAOYSA-N hept-5-en-2-ylbenzene Chemical compound CC=CCCC(C)C1=CC=CC=C1 KPNLFQFVZPTZGH-UHFFFAOYSA-N 0.000 description 1
- YVNCCKPQDDILKX-UHFFFAOYSA-N hex-4-en-2-ylbenzene Chemical compound CC=CCC(C)C1=CC=CC=C1 YVNCCKPQDDILKX-UHFFFAOYSA-N 0.000 description 1
- QWWLPMZYNVWOHQ-UHFFFAOYSA-N hex-5-en-2-ylbenzene Chemical compound C=CCCC(C)C1=CC=CC=C1 QWWLPMZYNVWOHQ-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- YXJYBPXSEKMEEJ-UHFFFAOYSA-N phosphoric acid;sulfuric acid Chemical compound OP(O)(O)=O.OS(O)(=O)=O YXJYBPXSEKMEEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- JLQFVGYYVXALAG-CFEVTAHFSA-N yasmin 28 Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 JLQFVGYYVXALAG-CFEVTAHFSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/31—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Devices And Processes Conducted In The Presence Of Fluids And Solid Particles (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50026497A JPS5929565B2 (ja) | 1975-03-06 | 1975-03-06 | アルキルテトラリンの製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055964A true CA1055964A (en) | 1979-06-05 |
Family
ID=12195115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,704A Expired CA1055964A (en) | 1975-03-06 | 1975-07-03 | Process for the preparation of alkyltetralins |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5929565B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1055964A (enrdf_load_stackoverflow) |
| FR (1) | FR2302984A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1502170A (enrdf_load_stackoverflow) |
| NL (1) | NL161123C (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5512083B2 (ja) * | 2007-12-18 | 2014-06-04 | 日揮株式会社 | 反応器内部の反応速度制御方法、反応装置及びジメチルエーテルの製造方法。 |
| CN115504849A (zh) | 2021-06-07 | 2022-12-23 | 河北中化滏恒股份有限公司 | 1,4－二甲基四氢萘的制造方法 |
-
1975
- 1975-03-06 JP JP50026497A patent/JPS5929565B2/ja not_active Expired
- 1975-06-27 GB GB2731575A patent/GB1502170A/en not_active Expired
- 1975-07-03 CA CA230,704A patent/CA1055964A/en not_active Expired
- 1975-07-17 NL NL7508568A patent/NL161123C/xx not_active IP Right Cessation
- 1975-09-18 FR FR7528620A patent/FR2302984A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7508568A (nl) | 1976-09-08 |
| FR2302984B1 (enrdf_load_stackoverflow) | 1978-04-07 |
| NL161123C (nl) | 1980-01-15 |
| JPS51101963A (enrdf_load_stackoverflow) | 1976-09-08 |
| NL161123B (nl) | 1979-08-15 |
| JPS5929565B2 (ja) | 1984-07-21 |
| GB1502170A (en) | 1978-02-22 |
| FR2302984A1 (fr) | 1976-10-01 |
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