JPS62138466A - ４，４′−モノチオビスフエノ−ル類の製法 - Google Patents
４，４′−モノチオビスフエノ−ル類の製法Info
- Publication number
- JPS62138466A JPS62138466A JP60280745A JP28074585A JPS62138466A JP S62138466 A JPS62138466 A JP S62138466A JP 60280745 A JP60280745 A JP 60280745A JP 28074585 A JP28074585 A JP 28074585A JP S62138466 A JPS62138466 A JP S62138466A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- sulfur dichloride
- phenol
- yield
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 title description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 14
- 150000002989 phenols Chemical class 0.000 claims description 10
- 150000002497 iodine compounds Chemical class 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- -1 bromine compound Chemical class 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 150000003739 xylenols Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- JPSMTGONABILTP-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)sulfanyl-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(SC=2C=C(C)C(O)=C(C)C=2)=C1 JPSMTGONABILTP-UHFFFAOYSA-N 0.000 description 2
- IBNFPRMKLZDANU-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)sulfanyl-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SC=2C=C(C)C(O)=CC=2)=C1 IBNFPRMKLZDANU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000238413 Octopus Species 0.000 description 1
- 241000277269 Oncorhynchus masou Species 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Inorganic materials [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60280745A JPS62138466A (ja) | 1985-12-12 | 1985-12-12 | ４，４′−モノチオビスフエノ−ル類の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60280745A JPS62138466A (ja) | 1985-12-12 | 1985-12-12 | ４，４′−モノチオビスフエノ−ル類の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62138466A true JPS62138466A (ja) | 1987-06-22 |
| JPH0453860B2 JPH0453860B2 (en]) | 1992-08-27 |
Family
ID=17629361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60280745A Granted JPS62138466A (ja) | 1985-12-12 | 1985-12-12 | ４，４′−モノチオビスフエノ−ル類の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62138466A (en]) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2436834A (en) * | 2006-04-07 | 2007-10-10 | John Henry Paul Tyman | Thiobisphenol antioxidant additives |
| CN102531979A (zh) * | 2012-01-06 | 2012-07-04 | 淄博万科化工有限公司 | 4,4'-二羟基二苯硫醚的生产方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4910663A (en]) * | 1972-05-24 | 1974-01-30 |
-
1985
- 1985-12-12 JP JP60280745A patent/JPS62138466A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4910663A (en]) * | 1972-05-24 | 1974-01-30 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2436834A (en) * | 2006-04-07 | 2007-10-10 | John Henry Paul Tyman | Thiobisphenol antioxidant additives |
| GB2436834B (en) * | 2006-04-07 | 2010-12-29 | John Henry Paul Tyman | The synthesis of di-[4-hydroxy-3-(tetramethylbutyl)phenyl)]-sulphide and t-nonyl analogue effective antioxidants for lubricating oils |
| CN102531979A (zh) * | 2012-01-06 | 2012-07-04 | 淄博万科化工有限公司 | 4,4'-二羟基二苯硫醚的生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0453860B2 (en]) | 1992-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS62138466A (ja) | ４，４′−モノチオビスフエノ−ル類の製法 | |
| JPH06157513A (ja) | ２−アセチルベンゾ［ｂ］チオフェンの製造法 | |
| JPS59122456A (ja) | ジシクロヘキシルジスルフイドの製造法 | |
| JPH07258204A (ja) | チオアリール化合物の製造方法 | |
| US4210766A (en) | Process for producing 2-halo-4-bromophenols | |
| CA1059149A (en) | Process for selectively producing 4,4'-monothiodiphenolic compounds in high yields | |
| JPS6348260A (ja) | ベンゼンスルフイン酸アルカリ金属塩の製法 | |
| US2849494A (en) | 2, 2'-thiobis | |
| JP4508377B2 (ja) | スルホニル化合物の製造方法 | |
| JPH08198841A (ja) | スルホニル化合物の製造方法 | |
| KR820001602B1 (ko) | 2, 2'-비스[4-(1, 1, 3, 3-테트라메틸부틸)페놀] 설파이드의 제조방법 | |
| JPS5842866B2 (ja) | ２，２′↓−ビス〔４↓−（１，１，３，３↓−テトラメチルブチル）フェノ−ル〕スルフィドの製造法 | |
| JPH0535139B2 (en]) | ||
| KR800001589B1 (ko) | 클로로 술포닐 벤조일 클로리드의 제조방법 | |
| JPS6121549B2 (en]) | ||
| JPH0656760A (ja) | ２，５−ジクロロアルキルチオベンゼンの製造法 | |
| JP2003064051A (ja) | スルホニル化合物の製造方法 | |
| JP2649722B2 (ja) | ４，４’‐（１―フェニルエチリデン）ビスフェノールの製造方法 | |
| KR910003635B1 (ko) | 2-(2-나프틸옥시)프로피온아닐리드 유도체의 제조방법 | |
| JPS603376B2 (ja) | カルコン誘導体及びその製造方法 | |
| JPH05140086A (ja) | ハロゲノチオフエノールの製造方法および精製方法 | |
| US6444853B1 (en) | Process for producing aromatic disulfides | |
| JPH01213260A (ja) | 高純度ビス（４−ヒドロキシフェニル）スルフィド化合物の製法 | |
| JPH023672A (ja) | ２，６‐ジエチルアニリン誘導体およびその製法 | |
| JPH0352885A (ja) | チオフェンジカルボン酸ジエステルを製造する方法 |