JPH0260664B2 - - Google Patents

Info

Publication number: JPH0260664B2
Authority: JP; Japan
Prior art keywords: tert; group; butyl; carbon atoms; reaction product
Prior art date: 1977-01-11
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

JP14150786A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6248662A (ja

Inventor

Esu Kotsutoman Kaakutsudo

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.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

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.)

1977-01-11

Filing date

1986-06-19

Publication date

1990-12-17

1977-01-11 Priority claimed from JP185877A external-priority patent/JPS5387327A/ja

1986-06-19 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1986-06-19 Priority to JP14150786A priority Critical patent/JPS6248662A/ja

1987-03-03 Publication of JPS6248662A publication Critical patent/JPS6248662A/ja

1990-12-17 Publication of JPH0260664B2 publication Critical patent/JPH0260664B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 14
150000002989 phenols Chemical class 0.000 claims description 12
125000002947 alkylene group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
239000007795 chemical reaction product Substances 0.000 description 25
-1 tert-butyl-4-hydroxybenzyl Chemical group 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000013078 crystal Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
238000010992 reflux Methods 0.000 description 13
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 9
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000003963 antioxidant agent Substances 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 7
230000003078 antioxidant effect Effects 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
239000002904 solvent Substances 0.000 description 6
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
239000004743 Polypropylene Substances 0.000 description 5
229920001155 polypropylene Polymers 0.000 description 5
DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000000034 method Methods 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
239000000395 magnesium oxide Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
229940044613 1-propanol Drugs 0.000 description 2
JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 2
HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 2
RXGGDIMRRGFCMJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3-hydroxybutan-2-yl)phenol Chemical compound CC(O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RXGGDIMRRGFCMJ-UHFFFAOYSA-N 0.000 description 2
KPYNPYLYIYBHEI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3-hydroxypropyl)phenol Chemical compound CC(C)(C)C1=CC(CCCO)=CC(C(C)(C)C)=C1O KPYNPYLYIYBHEI-UHFFFAOYSA-N 0.000 description 2
ROGIGVJNMOMGKV-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetic acid Chemical compound CC(C)(C)C1=CC(CSCC(O)=O)=CC(C(C)(C)C)=C1O ROGIGVJNMOMGKV-UHFFFAOYSA-N 0.000 description 2
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000004040 coloring Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
OAHOSAFPDBZWAU-UHFFFAOYSA-N (3-cyclooctyl-4-hydroxy-5-methylphenyl)methyl 3-sulfanylpropanoate Chemical compound CC1=CC(COC(=O)CCS)=CC(C2CCCCCCC2)=C1O OAHOSAFPDBZWAU-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
AKOUXCHVUHZABX-UHFFFAOYSA-N 2,6-dibutylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCC1=CC(=O)C=C(CCCC)C1=O AKOUXCHVUHZABX-UHFFFAOYSA-N 0.000 description 1
HJBNPHZFWDSJLR-UHFFFAOYSA-N 2,6-dicyclopentyl-4-(2-hydroxyethyl)phenol Chemical compound OC=1C(C2CCCC2)=CC(CCO)=CC=1C1CCCC1 HJBNPHZFWDSJLR-UHFFFAOYSA-N 0.000 description 1
QWRSZQIVPCUXAY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(1-hydroxyethoxy)phenol Chemical compound CC(O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QWRSZQIVPCUXAY-UHFFFAOYSA-N 0.000 description 1
ADBOIWHPABQNIV-UHFFFAOYSA-N 2,6-ditert-butyl-4-(10-hydroxydecyl)phenol Chemical compound CC(C)(C)C1=CC(CCCCCCCCCCO)=CC(C(C)(C)C)=C1O ADBOIWHPABQNIV-UHFFFAOYSA-N 0.000 description 1
XLWJPQQFJNGUPA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3-hydroxy-2,2-dimethylpropyl)phenol Chemical compound OCC(C)(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XLWJPQQFJNGUPA-UHFFFAOYSA-N 0.000 description 1
NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 description 1
LLZSGWFRZMQVBG-UHFFFAOYSA-N 2-decyl-4-(3-hydroxybutan-2-yl)phenol Chemical compound CCCCCCCCCCC1=CC(C(C)C(C)O)=CC=C1O LLZSGWFRZMQVBG-UHFFFAOYSA-N 0.000 description 1
PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 1
ZVXBWEIAIZEPGR-UHFFFAOYSA-N 4-(hydroxymethyl)-2,6-dimethylphenol Chemical compound CC1=CC(CO)=CC(C)=C1O ZVXBWEIAIZEPGR-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
WCALWFBKOIGUTM-UHFFFAOYSA-N [3-(3,5-ditert-butyl-4-hydroxyphenyl)-2,2-dimethylpropyl] 3-sulfanylpropanoate Chemical compound CC(C)(C)C1=CC(CC(C)(C)COC(=O)CCS)=CC(C(C)(C)C)=C1O WCALWFBKOIGUTM-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 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
230000015572 biosynthetic process Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
239000012986 chain transfer agent Substances 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
SNWKNPMDQONHKK-UHFFFAOYSA-N methyl 2-sulfanylpropanoate Chemical compound COC(=O)C(C)S SNWKNPMDQONHKK-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N n-butyl carbinol Natural products CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
238000011017 operating method Methods 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
RIMHDIYZJQVNSO-UHFFFAOYSA-N propyl 3-sulfanylpropanoate Chemical compound CCCOC(=O)CCS RIMHDIYZJQVNSO-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compositions Of Macromolecular Compounds (AREA)

JP14150786A 1977-01-11 1986-06-19 フェノール系化合物の製造方法 Granted JPS6248662A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP14150786A JPS6248662A (ja)	1977-01-11	1986-06-19	フェノール系化合物の製造方法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP185877A JPS5387327A (en)	1977-01-11	1977-01-11	Phenol system compound and process for preparing same
JP14150786A JPS6248662A (ja)	1977-01-11	1986-06-19	フェノール系化合物の製造方法

Publications (2)

Publication Number	Publication Date
JPS6248662A JPS6248662A (ja)	1987-03-03
JPH0260664B2 true JPH0260664B2 (fr)	1990-12-17

Family

ID=26335148

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14150786A Granted JPS6248662A (ja)	1977-01-11	1986-06-19	フェノール系化合物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS6248662A (fr)

1986
- 1986-06-19 JP JP14150786A patent/JPS6248662A/ja active Granted

Also Published As

Publication number	Publication date
JPS6248662A (ja)	1987-03-03

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US3953519A (en)	1976-04-27	Process for the preparation of a thiobis-2,6-disubstituted phenol from sulfur and a phenol
DE19900810A1 (de)	1999-09-09	Photokatonisch härtbare Zusammensetzung und Verfahren zu ihrer Herstellung
US4745203A (en)	1988-05-17	Process for the preparation of mixtures of metal salts of ring-substituted salicylic acid compounds
JPS6411222B2 (fr)	1989-02-23
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JPH0260664B2 (fr)	1990-12-17
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SU450800A1 (ru)	1974-11-25	Способ получени 6-алкил(арил)производных1,2,3,4-тетрагидрохинолина