JPH0222053B2 - - Google Patents
Info
- Publication number
- JPH0222053B2 JPH0222053B2 JP56147805A JP14780581A JPH0222053B2 JP H0222053 B2 JPH0222053 B2 JP H0222053B2 JP 56147805 A JP56147805 A JP 56147805A JP 14780581 A JP14780581 A JP 14780581A JP H0222053 B2 JPH0222053 B2 JP H0222053B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- butylphenol
- phenol
- reaction
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 48
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 36
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 22
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000004927 clay Substances 0.000 claims description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 5
- 238000006462 rearrangement reaction Methods 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- 239000005909 Kieselgur Substances 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 3
- 150000002910 rare earth metals Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 49
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical group CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 36
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 27
- 239000007795 chemical reaction product Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- -1 C 4 hydrocarbons Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 11
- 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 8
- 239000002994 raw material Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 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 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PNKZBZPLRKCVLI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxybenzene Chemical compound CC(C)(C)OC1=CC=CC=C1 PNKZBZPLRKCVLI-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-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
- 239000001273 butane Substances 0.000 description 2
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-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
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 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
- 239000000463 material Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 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
- 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 2
- 150000002989 phenols Chemical class 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
- BHAATXNWFXYIHA-UHFFFAOYSA-N (2,4,6-trinitrophenyl)methanesulfonic acid Chemical compound OS(=O)(=O)CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O BHAATXNWFXYIHA-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
- 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
- ZZXDRXVIRVJQBT-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1C ZZXDRXVIRVJQBT-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
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- JUSXLWAFYVKNLT-UHFFFAOYSA-N 2-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Br JUSXLWAFYVKNLT-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
- CHGIWDWIZZBKNG-UHFFFAOYSA-N 4,8-dinitronaphthalene-2-sulfonic acid Chemical compound C1=CC=C([N+]([O-])=O)C2=CC(S(=O)(=O)O)=CC([N+]([O-])=O)=C21 CHGIWDWIZZBKNG-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
- 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
- UREOXAIKRFCBHW-UHFFFAOYSA-N 4-nitronaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=C([N+]([O-])=O)C2=C1S(O)(=O)=O UREOXAIKRFCBHW-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
- WLDFOWKHIWIHEE-UHFFFAOYSA-N 4-nitronaphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC([N+]([O-])=O)=C21 WLDFOWKHIWIHEE-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
- NXOIHHATVQOBMU-UHFFFAOYSA-N 7-nitronaphthalene-1-sulfonic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(S(=O)(=O)O)=CC=CC2=C1 NXOIHHATVQOBMU-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
- 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
- XJYBYQGLRAFVGT-UHFFFAOYSA-N 8-nitronaphthalene-1-sulfonic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(S(=O)(=O)O)=CC=CC2=C1 XJYBYQGLRAFVGT-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 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
- IEJVPSDTVKDCBF-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=CC=2C(=CC=C(C12)[N+](=O)[O-])S(=O)(=O)O Chemical compound [N+](=O)([O-])C1=CC=CC=2C(=CC=C(C12)[N+](=O)[O-])S(=O)(=O)O IEJVPSDTVKDCBF-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
- 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
- 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
- VJQIPKNMASGCOC-UHFFFAOYSA-N butan-2-yloxybenzene Chemical compound CCC(C)OC1=CC=CC=C1 VJQIPKNMASGCOC-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
- 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
- 238000000354 decomposition reaction Methods 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
- 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
- SITVNOOPPBSYNB-UHFFFAOYSA-N naphthalene-1,3,5,7-tetrasulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 SITVNOOPPBSYNB-UHFFFAOYSA-N 0.000 description 1
- INMHJULHWVWVFN-UHFFFAOYSA-N naphthalene-1,3,5-trisulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 INMHJULHWVWVFN-UHFFFAOYSA-N 0.000 description 1
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- FEWNRIKJXAQRJJ-UHFFFAOYSA-N naphthalene-1,3,7-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 FEWNRIKJXAQRJJ-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
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-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
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 238000002360 preparation method Methods 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
- 230000008707 rearrangement Effects 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 JPS5852233A (ja) | 1983-03-28 |
| JPH0222053B2 true 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) |
Families Citing this family (1)
| 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)
| 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)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5852233A (ja) | 1983-03-28 |
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