CN109293625B - 一种高纯度1,4-丁烷磺酸内酯的合成方法 - Google Patents
一种高纯度1,4-丁烷磺酸内酯的合成方法 Download PDFInfo
- Publication number
- CN109293625B CN109293625B CN201710614193.3A CN201710614193A CN109293625B CN 109293625 B CN109293625 B CN 109293625B CN 201710614193 A CN201710614193 A CN 201710614193A CN 109293625 B CN109293625 B CN 109293625B
- Authority
- CN
- China
- Prior art keywords
- butane sultone
- purity
- alcohol solvent
- chlorobutanol
- concentrating
- 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.)
- Active
Links
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000001308 synthesis method Methods 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims abstract description 32
- YEGPVWSPNYPPIK-UHFFFAOYSA-N 4-hydroxybutane-1-sulfonic acid Chemical compound OCCCCS(O)(=O)=O YEGPVWSPNYPPIK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 21
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 claims abstract description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 16
- 235000010265 sodium sulphite Nutrition 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 238000010992 reflux Methods 0.000 claims abstract description 15
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 11
- 230000018044 dehydration Effects 0.000 claims abstract description 10
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 10
- 239000011259 mixed solution Substances 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000011780 sodium chloride Substances 0.000 claims abstract description 8
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 8
- 238000001704 evaporation Methods 0.000 claims abstract description 7
- 230000008020 evaporation Effects 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims abstract description 4
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000005194 fractionation Methods 0.000 claims abstract description 4
- 230000020477 pH reduction Effects 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- PYLDCZJUHYVOAF-UHFFFAOYSA-N 4-chlorobutyl acetate Chemical compound CC(=O)OCCCCCl PYLDCZJUHYVOAF-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- BDFJWKALVSRGSR-UHFFFAOYSA-N butan-1-ol;sodium Chemical compound [Na].CCCCO BDFJWKALVSRGSR-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XUKSWKGOQKREON-UHFFFAOYSA-N 1,4-diacetoxybutane Chemical compound CC(=O)OCCCCOC(C)=O XUKSWKGOQKREON-UHFFFAOYSA-N 0.000 description 1
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
- GZLPFEYTAAXJCP-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-sulfonyl chloride Chemical group CC1=NOC(C)=C1S(Cl)(=O)=O GZLPFEYTAAXJCP-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006177 biological buffer Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710614193.3A CN109293625B (zh) | 2017-07-25 | 2017-07-25 | 一种高纯度1,4-丁烷磺酸内酯的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710614193.3A CN109293625B (zh) | 2017-07-25 | 2017-07-25 | 一种高纯度1,4-丁烷磺酸内酯的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109293625A CN109293625A (zh) | 2019-02-01 |
CN109293625B true CN109293625B (zh) | 2021-03-05 |
Family
ID=65168018
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710614193.3A Active CN109293625B (zh) | 2017-07-25 | 2017-07-25 | 一种高纯度1,4-丁烷磺酸内酯的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109293625B (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110105326A (zh) * | 2019-02-26 | 2019-08-09 | 武汉松石科技股份有限公司 | 一种1,3-丙烷磺酸内酯的制备方法 |
CN109956923A (zh) * | 2019-04-16 | 2019-07-02 | 张家港瀚康化工有限公司 | 微通道反应器制备1,4-丁烷磺内酯的方法 |
CN111175413B (zh) * | 2020-03-18 | 2022-08-02 | 山东滨州智源生物科技有限公司 | 一种磺丁基倍他环糊精钠原料或其制剂中4-氯丁醇醋酸酯含量的检测方法 |
CN112341427B (zh) * | 2020-10-30 | 2023-01-13 | 湖北吉和昌化工科技有限公司 | 1,4-丁烷磺酸内酯的合成工艺 |
CN114805288B (zh) * | 2021-01-20 | 2023-12-29 | 武汉松石科技股份有限公司 | 一种制备2,4-丁烷磺酸内酯的方法 |
CN114292257B (zh) * | 2021-12-27 | 2023-10-27 | 湖北吉和昌化工科技有限公司 | 一种1,4-丁烷磺内酯的合成方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101157681A (zh) * | 2007-11-01 | 2008-04-09 | 姜俊 | 一种制备1,3丙烷磺内酯的方法 |
CN106397392A (zh) * | 2016-08-31 | 2017-02-15 | 湖北吉和昌化工科技有限公司 | 1,4‑丁烷磺酸内酯及其合成工艺 |
-
2017
- 2017-07-25 CN CN201710614193.3A patent/CN109293625B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101157681A (zh) * | 2007-11-01 | 2008-04-09 | 姜俊 | 一种制备1,3丙烷磺内酯的方法 |
CN106397392A (zh) * | 2016-08-31 | 2017-02-15 | 湖北吉和昌化工科技有限公司 | 1,4‑丁烷磺酸内酯及其合成工艺 |
Also Published As
Publication number | Publication date |
---|---|
CN109293625A (zh) | 2019-02-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109293625B (zh) | 一种高纯度1,4-丁烷磺酸内酯的合成方法 | |
CN101386597A (zh) | 一种烷基咪唑类高铼酸盐离子液体及其制备方法 | |
CN109438488A (zh) | 一种液体草酸硼酸锂盐的制备方法 | |
CN112142574B (zh) | 一种9,9-二[4-(2-羟基乙氧基)苯基]芴的合成方法 | |
CN112830907A (zh) | 制备5-羟甲基糠醛的方法 | |
CN111057079A (zh) | 一种双草酸硼酸锂的提纯方法及双草酸硼酸锂 | |
CN101591247B (zh) | 合成4-(4-甲酯基苯基)丁醛的方法 | |
CN110294712B (zh) | 一种高纯咪唑醋酸盐离子液体的制备方法 | |
CN114315888A (zh) | 一种基于格氏法合成有机化合物的环保型方法 | |
CN112047883A (zh) | 顺苯磺酸阿曲库铵的制备方法 | |
US10294189B2 (en) | Process for producing fluorinated electrolyte solvent | |
CN102381947B (zh) | 手性2,2’-二烷氧基-1,1’联萘的合成方法 | |
CN102898501A (zh) | 以(-)-雪松二醇为手性辅助剂制备硼替佐米的方法 | |
CN114736144B (zh) | 一种多库酯钙的工业制备方法 | |
CN112010900B (zh) | 一种高纯反应型阻燃剂thpo的制备方法 | |
CN115557927A (zh) | 一种硫酸乙烯酯的制备方法 | |
CN101805241B (zh) | 一种制备氟取代茚化合物的方法 | |
CN101508678A (zh) | 2-甲基-4-氨基-5-乙酰氨甲基嘧啶的制备工艺方法 | |
CN109721584B (zh) | 一种制备1,4-二氧六环的方法 | |
CN102964233A (zh) | 一种3,5-二氟三氟甲基苯酮的合成方法 | |
CN102008978A (zh) | 手性催化剂及其制备方法和应用 | |
CN106167480A (zh) | 一种卡格列净中间体2‑(4‑氟苯基)噻吩的制备方法 | |
CN102731281A (zh) | 一种以洗油为原料制取粗芴和芴酮的方法 | |
CN103183610B (zh) | 一种从低纯度乙酸甲酯制取高纯度乙酸甲酯的方法 | |
CN112321428A (zh) | 一种r-(+)-2-(4-羟基苯氧基)丙酸乙酯的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20190201 Assignee: Feile New Material Technology (Shandong) Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000094 Denomination of invention: A synthesis method of high-purity 1,4-butanesulfonic acid lactone Granted publication date: 20210305 License type: Common License Record date: 20230506 |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20190201 Assignee: Yunnan Benyi Biotechnology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000117 Denomination of invention: A synthesis method of high-purity 1,4-butanesulfonic acid lactone Granted publication date: 20210305 License type: Common License Record date: 20230519 Application publication date: 20190201 Assignee: Yunnan Goudeli Biotechnology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000118 Denomination of invention: A synthesis method of high-purity 1,4-butanesulfonic acid lactone Granted publication date: 20210305 License type: Common License Record date: 20230519 |
|
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20190201 Assignee: Yunnan Weiqiang An Biotechnology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000119 Denomination of invention: A synthesis method of high-purity 1,4-butanesulfonic acid lactone Granted publication date: 20210305 License type: Common License Record date: 20230522 Application publication date: 20190201 Assignee: Yunnan Benyi Lanche Environmental Protection Technology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000120 Denomination of invention: A synthesis method of high-purity 1,4-butanesulfonic acid lactone Granted publication date: 20210305 License type: Common License Record date: 20230522 |
|
EC01 | Cancellation of recordation of patent licensing contract | ||
EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Feile New Material Technology (Shandong) Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000094 Date of cancellation: 20230807 |
|
EC01 | Cancellation of recordation of patent licensing contract | ||
EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Yunnan Benyi Lanche Environmental Protection Technology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000120 Date of cancellation: 20240426 Assignee: Yunnan Weiqiang An Biotechnology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000119 Date of cancellation: 20240426 Assignee: Yunnan Goudeli Biotechnology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000118 Date of cancellation: 20240426 Assignee: Yunnan Benyi Biotechnology Co.,Ltd. Assignor: JINGCHU University OF TECHNOLOGY Contract record no.: X2023420000117 Date of cancellation: 20240426 |