CN109293625A - 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
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- CN109293625A CN109293625A CN201710614193.3A CN201710614193A CN109293625A CN 109293625 A CN109293625 A CN 109293625A CN 201710614193 A CN201710614193 A CN 201710614193A CN 109293625 A CN109293625 A CN 109293625A
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- Prior art keywords
- nitrae
- isosorbide
- butane sultones
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- 239000001273 butane Substances 0.000 title claims abstract description 40
- 238000010189 synthetic method Methods 0.000 title claims abstract description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 title claims description 8
- 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 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 16
- 150000001298 alcohols Chemical class 0.000 claims abstract description 16
- 235000010265 sodium sulphite Nutrition 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000010992 reflux Methods 0.000 claims abstract description 13
- 238000011084 recovery Methods 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000011780 sodium chloride Substances 0.000 claims abstract description 8
- 238000009834 vaporization Methods 0.000 claims abstract description 8
- 238000005194 fractionation Methods 0.000 claims abstract description 7
- 230000008016 vaporization Effects 0.000 claims abstract description 7
- 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
- 238000010792 warming Methods 0.000 claims abstract description 4
- 230000020477 pH reduction Effects 0.000 claims abstract description 3
- 238000004064 recycling Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 235000019441 ethanol Nutrition 0.000 claims description 30
- 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 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 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
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- -1 filtering Substances 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000007701 flash-distillation Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 229920001084 poly(chloroprene) Polymers 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- BDFJWKALVSRGSR-UHFFFAOYSA-N butan-1-ol;sodium Chemical compound [Na].CCCCO BDFJWKALVSRGSR-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006177 biological buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 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
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 |
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| 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 true CN109293625A (zh) | 2019-02-01 |
| CN109293625B CN109293625B (zh) | 2021-03-05 |
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| 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 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CN111175413A (zh) * | 2020-03-18 | 2020-05-19 | 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 |
| CN112341427A (zh) * | 2020-10-30 | 2021-02-09 | 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 |
| CN114292257A (zh) * | 2021-12-27 | 2022-04-08 | 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 |
| CN114805288A (zh) * | 2021-01-20 | 2022-07-29 | 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 |
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 |
Cited By (10)
| 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 |
| CN111175413A (zh) * | 2020-03-18 | 2020-05-19 | 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 |
| 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 |
| CN112341427A (zh) * | 2020-10-30 | 2021-02-09 | 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 |
| 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 |
| CN114805288A (zh) * | 2021-01-20 | 2022-07-29 | 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 |
| 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 |
| CN114292257A (zh) * | 2021-12-27 | 2022-04-08 | 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 |
| 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 |
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| Publication number | Publication date |
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| CN109293625B (zh) | 2021-03-05 |
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