JPWO2013161394A1 - トリメチルスルホキソニウムブロミドの製造方法、およびトリメチルスルホキソニウムブロミドを製造する反応系の温度制御方法 - Google Patents
トリメチルスルホキソニウムブロミドの製造方法、およびトリメチルスルホキソニウムブロミドを製造する反応系の温度制御方法 Download PDFInfo
- Publication number
- JPWO2013161394A1 JPWO2013161394A1 JP2014512399A JP2014512399A JPWO2013161394A1 JP WO2013161394 A1 JPWO2013161394 A1 JP WO2013161394A1 JP 2014512399 A JP2014512399 A JP 2014512399A JP 2014512399 A JP2014512399 A JP 2014512399A JP WO2013161394 A1 JPWO2013161394 A1 JP WO2013161394A1
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- bromide
- reaction
- methyl bromide
- reaction system
- 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.)
- Pending
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 146
- KEPJZBFFLDRKSF-UHFFFAOYSA-M trimethylsulfoxonium bromide Chemical compound [Br-].C[S+](C)(C)=O KEPJZBFFLDRKSF-UHFFFAOYSA-M 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims description 16
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims abstract description 204
- 229940102396 methyl bromide Drugs 0.000 claims abstract description 102
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 86
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000003247 decreasing effect Effects 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- RWNXXQFJBALKAX-UHFFFAOYSA-N 1-(dipropoxymethoxy)propane Chemical compound CCCOC(OCCC)OCCC RWNXXQFJBALKAX-UHFFFAOYSA-N 0.000 claims description 3
- PUAUAWJVTROGJG-UHFFFAOYSA-N 2-[tri(propan-2-yloxy)methoxy]propane Chemical compound CC(C)OC(OC(C)C)(OC(C)C)OC(C)C PUAUAWJVTROGJG-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 claims description 3
- CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 claims description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 3
- LFMXSZSVDQJYDU-UHFFFAOYSA-N 1-(tripropoxymethoxy)propane Chemical compound CCCOC(OCCC)(OCCC)OCCC LFMXSZSVDQJYDU-UHFFFAOYSA-N 0.000 claims 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 8
- 230000007423 decrease Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014512399A JPWO2013161394A1 (ja) | 2012-04-24 | 2013-03-06 | トリメチルスルホキソニウムブロミドの製造方法、およびトリメチルスルホキソニウムブロミドを製造する反応系の温度制御方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012099132 | 2012-04-24 | ||
| JP2012099132 | 2012-04-24 | ||
| JP2014512399A JPWO2013161394A1 (ja) | 2012-04-24 | 2013-03-06 | トリメチルスルホキソニウムブロミドの製造方法、およびトリメチルスルホキソニウムブロミドを製造する反応系の温度制御方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPWO2013161394A1 true JPWO2013161394A1 (ja) | 2015-12-24 |
Family
ID=49482734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014512399A Pending JPWO2013161394A1 (ja) | 2012-04-24 | 2013-03-06 | トリメチルスルホキソニウムブロミドの製造方法、およびトリメチルスルホキソニウムブロミドを製造する反応系の温度制御方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20150051424A1 (https=) |
| EP (1) | EP2842941A4 (https=) |
| JP (1) | JPWO2013161394A1 (https=) |
| CN (1) | CN104185623B (https=) |
| IN (1) | IN2014DN08353A (https=) |
| WO (1) | WO2013161394A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117018851A (zh) * | 2023-08-17 | 2023-11-10 | 舞阳威森生物医药有限公司 | 一种三甲基溴化亚砜生产用尾气处理装置 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5448713A (en) * | 1977-09-09 | 1979-04-17 | Searle & Co | Manufacture of trimethylsulfoxonium bromide |
| JPH09235268A (ja) * | 1995-12-28 | 1997-09-09 | Kureha Chem Ind Co Ltd | トリメチルスルホキソニウム ブロミドの製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2882663B2 (ja) * | 1990-05-28 | 1999-04-12 | 株式会社リコー | 画像符号量予測符号化方法および装置 |
| EP0781765B1 (en) * | 1995-12-28 | 2000-02-16 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing trimethylsulfoxonium bromide |
| JP2006265171A (ja) * | 2005-03-24 | 2006-10-05 | Toyotama Koryo Kk | 香料組成物及び芳香製品の芳香性を改良又は増強する新しい方法 |
-
2013
- 2013-03-06 CN CN201380015163.0A patent/CN104185623B/zh not_active Expired - Fee Related
- 2013-03-06 WO PCT/JP2013/056106 patent/WO2013161394A1/ja not_active Ceased
- 2013-03-06 EP EP13782308.4A patent/EP2842941A4/en not_active Withdrawn
- 2013-03-06 IN IN8353DEN2014 patent/IN2014DN08353A/en unknown
- 2013-03-06 JP JP2014512399A patent/JPWO2013161394A1/ja active Pending
- 2013-03-06 US US14/396,231 patent/US20150051424A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5448713A (en) * | 1977-09-09 | 1979-04-17 | Searle & Co | Manufacture of trimethylsulfoxonium bromide |
| JPH09235268A (ja) * | 1995-12-28 | 1997-09-09 | Kureha Chem Ind Co Ltd | トリメチルスルホキソニウム ブロミドの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2842941A1 (en) | 2015-03-04 |
| IN2014DN08353A (https=) | 2015-05-08 |
| US20150051424A1 (en) | 2015-02-19 |
| EP2842941A4 (en) | 2015-12-23 |
| CN104185623B (zh) | 2016-01-06 |
| WO2013161394A1 (ja) | 2013-10-31 |
| CN104185623A (zh) | 2014-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160809 |
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| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20170411 |