JPS5852233A - パラタ−シヤリブチルフエノ−ルの製造方法 - Google Patents

パラタ−シヤリブチルフエノ−ルの製造方法

Info

Publication number: JPS5852233A
Authority: JP; Japan
Prior art keywords: acid; butylphenol; reaction; phenol; catalyst
Prior art date: 1981-09-21
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

Application number

JP56147805A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0222053B2 (de

Inventor

Toshiyuki Sugihara

杉原　俊行

Yasushi Tsutsui

筒井　靖「し」

Toshiaki Inagi

俊明稲木

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.)

YOTSUKAICHI GOSEI KK

Original Assignee

YOTSUKAICHI GOSEI KK

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.)

1981-09-21

Filing date

1981-09-21

Publication date

1983-03-28

1981-09-21 Application filed by YOTSUKAICHI GOSEI KK filed Critical YOTSUKAICHI GOSEI KK

1981-09-21 Priority to JP56147805A priority Critical patent/JPS5852233A/ja

1983-03-28 Publication of JPS5852233A publication Critical patent/JPS5852233A/ja

1990-05-17 Publication of JPH0222053B2 publication Critical patent/JPH0222053B2/ja

Status Granted legal-status Critical Current

Links

QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 title description 25
238000002360 preparation method Methods 0.000 title description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 46
239000003054 catalyst Substances 0.000 claims abstract description 26
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 13
239000004927 clay Substances 0.000 claims abstract description 11
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 7
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 7
229910015900 BF3 Chemical group 0.000 claims abstract description 5
229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 5
150000002910 rare earth metals Chemical group 0.000 claims abstract description 5
238000006462 rearrangement reaction Methods 0.000 claims abstract description 5
239000010457 zeolite Substances 0.000 claims abstract description 5
239000005909 Kieselgur Substances 0.000 claims abstract description 4
239000003456 ion exchange resin Chemical group 0.000 claims abstract description 4
229920003303 ion-exchange polymer Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract 3
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims description 44
238000004519 manufacturing process Methods 0.000 claims description 8
239000003377 acid catalyst Substances 0.000 claims description 4
239000000377 silicon dioxide Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 abstract description 48
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract description 29
239000002253 acid Substances 0.000 abstract description 28
239000002994 raw material Substances 0.000 abstract description 9
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract description 8
229930195733 hydrocarbon Natural products 0.000 abstract description 7
150000002430 hydrocarbons Chemical class 0.000 abstract description 7
229910021536 Zeolite Inorganic materials 0.000 abstract description 4
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 3
238000005336 cracking Methods 0.000 abstract description 2
239000011541 reaction mixture Substances 0.000 abstract 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 28
239000007795 chemical reaction product Substances 0.000 description 23
239000000203 mixture Substances 0.000 description 21
238000000034 method Methods 0.000 description 18
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 11
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 11
-1 etc.) Chemical compound 0.000 description 8
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 2
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 description 2
HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000005804 alkylation reaction Methods 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
239000007809 chemical reaction catalyst Substances 0.000 description 2
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
150000002085 enols Chemical class 0.000 description 2
239000011521 glass Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
PNKZBZPLRKCVLI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxybenzene Chemical compound CC(C)(C)OC1=CC=CC=C1 PNKZBZPLRKCVLI-UHFFFAOYSA-N 0.000 description 1
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
JIAMRSLGASIQPE-UHFFFAOYSA-N 1,6-dimethyl-5-nitrocyclohexa-2,4-diene-1-sulfonic acid Chemical compound [N+](=O)([O-])C=1C(C(C=CC1)(C)S(=O)(=O)O)C JIAMRSLGASIQPE-UHFFFAOYSA-N 0.000 description 1
RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
NCPFHAIPXWIXES-UHFFFAOYSA-N 1-nitronaphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=C([N+]([O-])=O)C(S(=O)(=O)O)=CC=C21 NCPFHAIPXWIXES-UHFFFAOYSA-N 0.000 description 1
XNJVIJQATFJERB-UHFFFAOYSA-N 2,3,4-trimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C)=C1C XNJVIJQATFJERB-UHFFFAOYSA-N 0.000 description 1
ZGZXYZZHXXTTJN-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1Cl ZGZXYZZHXXTTJN-UHFFFAOYSA-N 0.000 description 1
IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 description 1
IXSGUIFSMPTAGW-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C(F)(F)F IXSGUIFSMPTAGW-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
CMGPPGOUOGYCGD-UHFFFAOYSA-N 2-cyclohexylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C1CCCCC1 CMGPPGOUOGYCGD-UHFFFAOYSA-N 0.000 description 1
JIFAWAXKXDTUHW-UHFFFAOYSA-N 2-fluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1F JIFAWAXKXDTUHW-UHFFFAOYSA-N 0.000 description 1
WPFCHJIUEHHION-UHFFFAOYSA-N 2-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=C([N+]([O-])=O)C=CC2=C1 WPFCHJIUEHHION-UHFFFAOYSA-N 0.000 description 1
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
LOIHNWJKFVJSJT-UHFFFAOYSA-N 3-methylbenzene-1,2-disulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O LOIHNWJKFVJSJT-UHFFFAOYSA-N 0.000 description 1
JDQDSEVNMTYMOC-UHFFFAOYSA-N 3-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1 JDQDSEVNMTYMOC-UHFFFAOYSA-N 0.000 description 1
ZOZQXFASVITJFG-UHFFFAOYSA-N 3-nitrobenzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1S(O)(=O)=O ZOZQXFASVITJFG-UHFFFAOYSA-N 0.000 description 1
YDPFPDNDNZUKPL-UHFFFAOYSA-N 3-nitronaphthalene-1,5-disulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O YDPFPDNDNZUKPL-UHFFFAOYSA-N 0.000 description 1
PHZVGKMVVKFBCX-UHFFFAOYSA-N 4-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 PHZVGKMVVKFBCX-UHFFFAOYSA-N 0.000 description 1
JXBUOZMYKQDZFY-UHFFFAOYSA-N 4-hydroxybenzene-1,3-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O JXBUOZMYKQDZFY-UHFFFAOYSA-N 0.000 description 1
FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
OXVYWSXMLWQPHT-UHFFFAOYSA-N 4-methyl-8-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(C)=CC=C(S(O)(=O)=O)C2=C1[N+]([O-])=O OXVYWSXMLWQPHT-UHFFFAOYSA-N 0.000 description 1
WQFHQCVHUUSGMV-UHFFFAOYSA-N 4-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=C([N+]([O-])=O)C2=C1 WQFHQCVHUUSGMV-UHFFFAOYSA-N 0.000 description 1
VTSAIRRUQWCZGB-UHFFFAOYSA-N 4-nitronaphthalene-2,6-disulfonic acid Chemical compound [N+](=O)([O-])C1=CC(=CC2=CC=C(C=C12)S(=O)(=O)O)S(=O)(=O)O VTSAIRRUQWCZGB-UHFFFAOYSA-N 0.000 description 1
VGHJNLKOGBNGTR-UHFFFAOYSA-N 4-nitronaphthalene-2,7-disulfonic acid Chemical compound [O-][N+](=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VGHJNLKOGBNGTR-UHFFFAOYSA-N 0.000 description 1
DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 description 1
FTNWWQOFRQZWSC-UHFFFAOYSA-N 5-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1[N+]([O-])=O FTNWWQOFRQZWSC-UHFFFAOYSA-N 0.000 description 1
ZAPHEIOXULZTDR-UHFFFAOYSA-N 5-nitronaphthalene-2-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 ZAPHEIOXULZTDR-UHFFFAOYSA-N 0.000 description 1
VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 1
ZTRNMLNZZWIBPF-UHFFFAOYSA-N 6-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 ZTRNMLNZZWIBPF-UHFFFAOYSA-N 0.000 description 1
DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 description 1
CYJJLCDCWVZEDZ-UHFFFAOYSA-N 8-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 CYJJLCDCWVZEDZ-UHFFFAOYSA-N 0.000 description 1
ZMNKDHWBVMYLLC-UHFFFAOYSA-N 8-nitronaphthalene-1,3,5-trisulfonic acid Chemical compound [O-][N+](=O)C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 ZMNKDHWBVMYLLC-UHFFFAOYSA-N 0.000 description 1
CWBVVPNADQZLQY-UHFFFAOYSA-N 8-nitronaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC([N+]([O-])=O)=C21 CWBVVPNADQZLQY-UHFFFAOYSA-N 0.000 description 1
NSTVWFKHOITKNP-UHFFFAOYSA-N 8-nitronaphthalene-1,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(S(=O)(=O)O)=CC([N+]([O-])=O)=C21 NSTVWFKHOITKNP-UHFFFAOYSA-N 0.000 description 1
RLCVDUBXMVTRQZ-UHFFFAOYSA-N 8-nitronaphthalene-2-sulfonic acid Chemical compound C1=CC=C([N+]([O-])=O)C2=CC(S(=O)(=O)O)=CC=C21 RLCVDUBXMVTRQZ-UHFFFAOYSA-N 0.000 description 1
HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
PYXOHIOWTKLGKE-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=CC=1)S(=O)(=O)O)S(=O)(=O)O)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C=1C(=C(C(=CC=1)S(=O)(=O)O)S(=O)(=O)O)[N+](=O)[O-] PYXOHIOWTKLGKE-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
ILFFFKFZHRGICY-UHFFFAOYSA-N anthracene-1-sulfonic acid Chemical compound C1=CC=C2C=C3C(S(=O)(=O)O)=CC=CC3=CC2=C1 ILFFFKFZHRGICY-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
MHWVMMHIJHHXQP-UHFFFAOYSA-N benzene-1,2,3-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O MHWVMMHIJHHXQP-UHFFFAOYSA-N 0.000 description 1
MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
235000021028 berry Nutrition 0.000 description 1
239000001273 butane Substances 0.000 description 1
KOYGZROXUOTUEE-UHFFFAOYSA-N butane;but-1-ene Chemical compound CCCC.CCC=C KOYGZROXUOTUEE-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
UAKMCBRMMSMYLT-UHFFFAOYSA-N chloro(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)C1=CC=CC=C1 UAKMCBRMMSMYLT-UHFFFAOYSA-N 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
HWPZEWOIDTVKLI-UHFFFAOYSA-N dinitro(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C([N+]([O-])=O)([N+]([O-])=O)C1=CC=CC=C1 HWPZEWOIDTVKLI-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
HEWDOWUUTBCVJP-UHFFFAOYSA-N naphthalene-1,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HEWDOWUUTBCVJP-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
QFOYLCHPNNWUFY-UHFFFAOYSA-N phenanthrene-1-sulfonic acid Chemical compound C1=CC2=CC=CC=C2C2=C1C(S(=O)(=O)O)=CC=C2 QFOYLCHPNNWUFY-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
JOVLEOXYYWEEEW-UHFFFAOYSA-M sodium;1-amino-8-hydroxy-4-sulfonaphthalene-2-sulfonate Chemical compound [Na+].C1=CC(O)=C2C(N)=C(S([O-])(=O)=O)C=C(S(O)(=O)=O)C2=C1 JOVLEOXYYWEEEW-UHFFFAOYSA-M 0.000 description 1
QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000004230 steam cracking Methods 0.000 description 1
ZVTQDOIPKNCMAR-UHFFFAOYSA-N sulfanylidene(sulfanylideneboranylsulfanyl)borane Chemical class S=BSB=S ZVTQDOIPKNCMAR-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc 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

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

JP56147805A 1981-09-21 1981-09-21 パラタ−シヤリブチルフエノ−ルの製造方法 Granted JPS5852233A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP56147805A JPS5852233A (ja)	1981-09-21	1981-09-21	パラタ−シヤリブチルフエノ−ルの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56147805A JPS5852233A (ja)	1981-09-21	1981-09-21	パラタ−シヤリブチルフエノ−ルの製造方法

Publications (2)

Publication Number	Publication Date
JPS5852233A true JPS5852233A (ja)	1983-03-28
JPH0222053B2 JPH0222053B2 (de)	1990-05-17

Family

ID=15438607

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56147805A Granted JPS5852233A (ja)	1981-09-21	1981-09-21	パラタ−シヤリブチルフエノ−ルの製造方法

Country Status (1)

Country	Link
JP (1)	JPS5852233A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111205172A (zh) *	2020-01-13	2020-05-29	山东省临沂市三丰化工有限公司	一种2,4-二叔丁基苯酚的清洁生产方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3422157A (en) *	1966-04-18	1969-01-14	Union Carbide Corp	Process for continuous alkylation of arylhydroxides using ion exchange resins
JPS49823A (de) *	1972-04-17	1974-01-07
JPS4920190A (de) *	1972-06-20	1974-02-22
US3932537A (en) *	1971-09-09	1976-01-13	Reichhold Chemicals, Inc.	Alkylation of phenols

1981
- 1981-09-21 JP JP56147805A patent/JPS5852233A/ja active Granted

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3422157A (en) *	1966-04-18	1969-01-14	Union Carbide Corp	Process for continuous alkylation of arylhydroxides using ion exchange resins
US3932537A (en) *	1971-09-09	1976-01-13	Reichhold Chemicals, Inc.	Alkylation of phenols
JPS49823A (de) *	1972-04-17	1974-01-07
JPS4920190A (de) *	1972-06-20	1974-02-22

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111205172A (zh) *	2020-01-13	2020-05-29	山东省临沂市三丰化工有限公司	一种2,4-二叔丁基苯酚的清洁生产方法

Also Published As

Publication number	Publication date
JPH0222053B2 (de)	1990-05-17

Publication	Publication Date	Title
EP0406050B1 (de)	1994-09-07	Verfahren zur Herstellung von Phenolen
JPH07103058B2 (ja)	1995-11-08	ビスフェノールａの製造方法
JPS638089B2 (de)	1988-02-19
JPS63122636A (ja)	1988-05-26	アルキル基置換芳香族炭化水素の製造方法
CA1140945A (en)	1983-02-08	Process for preparation of high purity isobutylene
US2564072A (en)	1951-08-14	Alkylation process
JPH0529374B2 (de)	1993-04-30
NO139476B (no)	1978-12-11	Fremgangsmaate for fremstilling av et hoeyoktanprodukt ved totrinns alkylering av isobutan med henholdsvis propen og buten over hydrogenfluoridkatalysator
JPS5852233A (ja)	1983-03-28	パラタ−シヤリブチルフエノ−ルの製造方法
JPH0237898B2 (de)	1990-08-28
RU2142448C1 (ru)	1999-12-10	Способ получения пара-ксилола селективным метилированием толуола метилгалогенидами
CA1291172C (en)	1991-10-22	Process for the catalytic trans-halogenation of a polyiodo-benzene, and, in particular, of a di-iodo-benzene
JPS60149535A (ja)	1985-08-07	アルコ−ルの連続製造法
US4066713A (en)	1978-01-03	Process for the addition of organic acids to acetylenic compounds contained in inorganic or organic hydrocarbon streams
JP3792448B2 (ja)	2006-07-05	メタクリル酸の精製法
JPH0776533A (ja)	1995-03-20	α−メチルスチレン類の不飽和二量体の製造法
JPS61183230A (ja)	1986-08-15	２，２，３−トリメチルペンタンに富む留分の製造方法
JPH0456012B2 (de)	1992-09-07
DK172596B1 (da)	1999-02-15	Fremgangsmåde til fremstilling af et alkyleret carbonhydridprodukt ved trinvis væskefasealkylering af et carbonhydridsubstr
US5191136A (en)	1993-03-02	Process for production of sec-butylbenzene
EP0745579B1 (de)	1999-08-04	Verfahren zum Herstellen von sekundairem Butylacrylat durch Reaktion von Acrylsäure mit Butenisomeren
JPS63159333A (ja)	1988-07-02	２，４−ジ−ｔ−ブチルフエノ−ルの製造方法
JPH0347139A (ja)	1991-02-28	ｓｅｃ―ブチルベンゼンの製造方法
JP3360759B2 (ja)	2002-12-24	オレフィンの接触水和方法
JPH059135A (ja)	1993-01-19	ポリアルキルベンゼンの製造方法

JPS5852233A - パラタ−シヤリブチルフエノ−ルの製造方法 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15438607

Family Applications (1)

Country Status (1)

Cited By (1)

Citations (4)

Patent Citations (4)

Cited By (1)

Also Published As

Similar Documents