TWI570112B - Preparation of bis (β-epoxypropyl) sulfide and bis (β-epoxypropyl) polysulfide - Google Patents
Preparation of bis (β-epoxypropyl) sulfide and bis (β-epoxypropyl) polysulfide Download PDFInfo
- Publication number
- TWI570112B TWI570112B TW102119420A TW102119420A TWI570112B TW I570112 B TWI570112 B TW I570112B TW 102119420 A TW102119420 A TW 102119420A TW 102119420 A TW102119420 A TW 102119420A TW I570112 B TWI570112 B TW I570112B
- Authority
- TW
- Taiwan
- Prior art keywords
- metal
- epihalohydrin
- compound
- sulfide
- polysulfide
- Prior art date
Links
- 239000005077 polysulfide Substances 0.000 title claims description 39
- 229920001021 polysulfide Polymers 0.000 title claims description 39
- 150000008117 polysulfides Polymers 0.000 title claims description 39
- -1 β-epoxypropyl Chemical group 0.000 title claims description 30
- WISUILQECWFZCN-UHFFFAOYSA-N 2-(oxiran-2-ylmethylsulfanylmethyl)oxirane Chemical compound C1OC1CSCC1CO1 WISUILQECWFZCN-UHFFFAOYSA-N 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 69
- 229910052751 metal Inorganic materials 0.000 claims description 63
- 239000002184 metal Substances 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 238000004519 manufacturing process Methods 0.000 claims description 41
- 150000007514 bases Chemical class 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 239000011593 sulfur Substances 0.000 claims description 33
- 229910052976 metal sulfide Inorganic materials 0.000 claims description 16
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 6
- 150000002736 metal compounds Chemical class 0.000 claims description 5
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 5
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 5
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims description 3
- 229940016373 potassium polysulfide Drugs 0.000 claims description 3
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 claims description 3
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 claims description 3
- 150000003944 halohydrins Chemical class 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000004593 Epoxy Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 32
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 31
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
- 150000008282 halocarbons Chemical class 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
- 239000000920 calcium hydroxide Substances 0.000 description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 6
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 6
- 239000000347 magnesium hydroxide Substances 0.000 description 6
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical group [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
- 239000001095 magnesium carbonate Substances 0.000 description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OLPXIHXXKBDZES-UHFFFAOYSA-L 37488-76-9 Chemical compound [Na+].[Na+].[S-]S[S-] OLPXIHXXKBDZES-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- ZLCCLBKPLLUIJC-UHFFFAOYSA-L disodium tetrasulfane-1,4-diide Chemical compound [Na+].[Na+].[S-]SS[S-] ZLCCLBKPLLUIJC-UHFFFAOYSA-L 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003553 thiiranes Chemical group 0.000 description 2
- ZXACHZITICPUKS-UHFFFAOYSA-N 2-[(oxiran-2-ylmethyldisulfanyl)methyl]oxirane Chemical compound C1OC1CSSCC1CO1 ZXACHZITICPUKS-UHFFFAOYSA-N 0.000 description 1
- JUJMAXXTSMCFDV-UHFFFAOYSA-N 2-methyl-2-[(2-methyloxiran-2-yl)tetrasulfanyl]oxirane Chemical compound CC1(CO1)SSSSC1(C)CO1 JUJMAXXTSMCFDV-UHFFFAOYSA-N 0.000 description 1
- JCSQNJXQCZRNLO-UHFFFAOYSA-N 2-methyl-2-[(2-methyloxiran-2-yl)trisulfanyl]oxirane Chemical compound CC1(CO1)SSSC1(C)CO1 JCSQNJXQCZRNLO-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CQODGVQBRIGKLJ-UHFFFAOYSA-L [Na+].[Na+].[O-]OOO[O-] Chemical compound [Na+].[Na+].[O-]OOO[O-] CQODGVQBRIGKLJ-UHFFFAOYSA-L 0.000 description 1
- WMEKSYHDIDMJMC-UHFFFAOYSA-L [Na+].[Na+].[S-]SSS[S-] Chemical compound [Na+].[Na+].[S-]SSS[S-] WMEKSYHDIDMJMC-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012143171 | 2012-06-26 | ||
| JP2012181524 | 2012-08-20 | ||
| JP2012181523 | 2012-08-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201412726A TW201412726A (zh) | 2014-04-01 |
| TWI570112B true TWI570112B (zh) | 2017-02-11 |
Family
ID=49783033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102119420A TWI570112B (zh) | 2012-06-26 | 2013-05-31 | Preparation of bis (β-epoxypropyl) sulfide and bis (β-epoxypropyl) polysulfide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9133151B2 (enExample) |
| EP (1) | EP2865673B1 (enExample) |
| JP (1) | JP6128124B2 (enExample) |
| KR (1) | KR102013700B1 (enExample) |
| CN (1) | CN104379569B (enExample) |
| BR (1) | BR112014024437B8 (enExample) |
| IN (1) | IN2015DN00047A (enExample) |
| TW (1) | TWI570112B (enExample) |
| WO (1) | WO2014002876A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3052783B1 (fr) * | 2016-06-15 | 2018-05-25 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc renforcee pour pneumatique |
| CN112094213A (zh) * | 2019-06-18 | 2020-12-18 | 北京化工大学 | 一种环保型的非硅烷类偶联剂及其制备方法和橡胶组合物 |
| CN110156748A (zh) * | 2019-06-18 | 2019-08-23 | 江苏可奥熙光学材料科技有限公司 | 一种高折光率镜片单体的制备方法 |
| EP4209525A4 (en) * | 2020-09-01 | 2025-06-25 | SK pucore co., ltd. | POLYTHIOL COMPOSITION, OPTICAL COMPOSITION AND OPTICAL PRODUCTS |
| CN112480095B (zh) * | 2020-11-25 | 2022-06-10 | 益丰新材料股份有限公司 | 一种双(2,3-环硫丙基)硫醚的制备方法 |
| CN113461642B (zh) * | 2021-06-21 | 2023-03-10 | 西安瑞联新材料股份有限公司 | 一种2,2’-[硫代双(亚甲基)]双环氧乙烷的制备方法 |
| CN120208916B (zh) * | 2025-03-26 | 2025-11-25 | 合肥和晨生物科技有限公司 | 一种双(2,3-环硫丙基)二硫醚的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0761665A2 (en) * | 1995-08-16 | 1997-03-12 | Mitsubishi Gas Chemical Company, Inc. | Episulfide group containing alkyl sulfide compounds |
| EP1484352A1 (en) * | 2002-03-12 | 2004-12-08 | Mitsui Chemicals, Inc. | Thioepoxy based polymerizable composition and method for production thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3491660B2 (ja) * | 1995-08-16 | 2004-01-26 | 三菱瓦斯化学株式会社 | 新規な直鎖アルキルスルフィド型エピスルフィド化合物 |
| JP3864998B2 (ja) | 1995-09-08 | 2007-01-10 | 三菱瓦斯化学株式会社 | 新規な分岐アルキルスルフィド型エピスルフィド化合物 |
| JPH11180977A (ja) | 1997-10-16 | 1999-07-06 | Mitsubishi Gas Chem Co Inc | 新規なエピスルフィド化合物 |
| JP3315090B2 (ja) | 1998-03-13 | 2002-08-19 | 三井化学株式会社 | 重合性組成物 |
| JP4069342B2 (ja) | 1998-11-16 | 2008-04-02 | 三菱瓦斯化学株式会社 | ハロヒドリン化合物の製造方法 |
| JP2003048883A (ja) | 2001-05-29 | 2003-02-21 | Mitsubishi Gas Chem Co Inc | エピスルフィド化合物の製造方法 |
| JP4124678B2 (ja) * | 2002-03-12 | 2008-07-23 | 三井化学株式会社 | チオエポキシ系重合性組成物の製造方法 |
| WO2009066687A1 (ja) * | 2007-11-21 | 2009-05-28 | Konica Minolta Opto, Inc. | 対物レンズ及び撮像レンズ |
| KR101522755B1 (ko) * | 2008-02-13 | 2015-05-26 | 미츠비시 가스 가가쿠 가부시키가이샤 | 수지용 조성물 및 그것을 포함하는 광학렌즈 |
-
2013
- 2013-05-31 TW TW102119420A patent/TWI570112B/zh active
- 2013-06-21 EP EP13810392.4A patent/EP2865673B1/en active Active
- 2013-06-21 BR BR112014024437A patent/BR112014024437B8/pt active IP Right Grant
- 2013-06-21 JP JP2014522582A patent/JP6128124B2/ja active Active
- 2013-06-21 US US14/402,442 patent/US9133151B2/en active Active
- 2013-06-21 CN CN201380028568.8A patent/CN104379569B/zh active Active
- 2013-06-21 WO PCT/JP2013/067032 patent/WO2014002876A1/ja not_active Ceased
- 2013-06-21 IN IN47DEN2015 patent/IN2015DN00047A/en unknown
- 2013-06-21 KR KR1020147024557A patent/KR102013700B1/ko active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0761665A2 (en) * | 1995-08-16 | 1997-03-12 | Mitsubishi Gas Chemical Company, Inc. | Episulfide group containing alkyl sulfide compounds |
| EP1484352A1 (en) * | 2002-03-12 | 2004-12-08 | Mitsui Chemicals, Inc. | Thioepoxy based polymerizable composition and method for production thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014002876A1 (ja) | 2014-01-03 |
| EP2865673B1 (en) | 2019-02-27 |
| JPWO2014002876A1 (ja) | 2016-05-30 |
| KR20150035489A (ko) | 2015-04-06 |
| CN104379569A (zh) | 2015-02-25 |
| BR112014024437B8 (pt) | 2020-11-17 |
| BR112014024437A2 (pt) | 2017-07-25 |
| KR102013700B1 (ko) | 2019-08-23 |
| BR112014024437B1 (pt) | 2020-11-03 |
| IN2015DN00047A (enExample) | 2015-05-22 |
| TW201412726A (zh) | 2014-04-01 |
| US9133151B2 (en) | 2015-09-15 |
| EP2865673A4 (en) | 2016-02-24 |
| EP2865673A1 (en) | 2015-04-29 |
| CN104379569B (zh) | 2017-05-24 |
| US20150158836A1 (en) | 2015-06-11 |
| JP6128124B2 (ja) | 2017-05-17 |
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