CA1055964A - Procede pour la preparation d'alkyltetralines - Google Patents

Procede pour la preparation d'alkyltetralines

Info

Publication number: CA1055964A
Authority: CA; Canada
Prior art keywords: reaction; reaction zone; catalyst; alkenylbenzene; temperature
Prior art date: 1975-03-06
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

Application number

CA230,704A

Other languages

English (en)

Inventor

Michiyuki Tokashiki

Hiroshi Sakai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Teijin Ltd

Original Assignee

Teijin Ltd

Priority date (The priority date 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 date listed.)

1975-03-06

Filing date

1975-07-03

Publication date

1979-06-05

1975-07-03 Application filed by Teijin Ltd filed Critical Teijin Ltd

1979-06-05 Application granted granted Critical

1979-06-05 Publication of CA1055964A publication Critical patent/CA1055964A/fr

Status Expired legal-status Critical Current

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)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Devices And Processes Conducted In The Presence Of Fluids And Solid Particles (AREA)

CA230,704A 1975-03-06 1975-07-03 Procede pour la preparation d'alkyltetralines Expired CA1055964A (fr)

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 (fr)	1979-06-05

Family

ID=12195115

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA230,704A Expired CA1055964A (fr)	1975-03-06	1975-07-03	Procede pour la preparation d'alkyltetralines

Country Status (5)

Country	Link
JP (1)	JPS5929565B2 (fr)
CA (1)	CA1055964A (fr)
FR (1)	FR2302984A1 (fr)
GB (1)	GB1502170A (fr)
NL (1)	NL161123C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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/fr 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
JPS5929565B2 (ja)	1984-07-21
JPS51101963A (fr)	1976-09-08
FR2302984A1 (fr)	1976-10-01
NL161123B (nl)	1979-08-15
FR2302984B1 (fr)	1978-04-07
GB1502170A (en)	1978-02-22
NL161123C (nl)	1980-01-15
NL7508568A (nl)	1976-09-08

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EP0812813A2 (fr)	1997-12-17	Procédé pour la préparation de dialkylnaphthalènes
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