CN115073302A - 一种从副产母液中提取四丁基溴化铵的方法 - Google Patents
一种从副产母液中提取四丁基溴化铵的方法 Download PDFInfo
- Publication number
- CN115073302A CN115073302A CN202211009737.0A CN202211009737A CN115073302A CN 115073302 A CN115073302 A CN 115073302A CN 202211009737 A CN202211009737 A CN 202211009737A CN 115073302 A CN115073302 A CN 115073302A
- Authority
- CN
- China
- Prior art keywords
- crystallization
- liquid
- tetrabutylammonium bromide
- film evaporation
- mother liquor
- 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 title claims abstract description 64
- 239000006227 byproduct Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000012452 mother liquor Substances 0.000 title claims abstract description 37
- 239000007788 liquid Substances 0.000 claims abstract description 90
- 238000001704 evaporation Methods 0.000 claims abstract description 86
- 230000008020 evaporation Effects 0.000 claims abstract description 73
- 238000002425 crystallisation Methods 0.000 claims abstract description 70
- 230000008025 crystallization Effects 0.000 claims abstract description 66
- 238000001816 cooling Methods 0.000 claims abstract description 38
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 238000003756 stirring Methods 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 22
- 239000008367 deionised water Substances 0.000 claims description 20
- 229910021641 deionized water Inorganic materials 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 18
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 17
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 17
- 239000000843 powder Substances 0.000 claims description 16
- 239000005995 Aluminium silicate Substances 0.000 claims description 15
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 15
- 235000012211 aluminium silicate Nutrition 0.000 claims description 15
- 150000003863 ammonium salts Chemical class 0.000 claims description 15
- 239000004917 carbon fiber Substances 0.000 claims description 15
- 210000003918 fraction a Anatomy 0.000 claims description 15
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- 238000001354 calcination Methods 0.000 claims description 11
- 239000010413 mother solution Substances 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 11
- KEZYHIPQRGTUDU-UHFFFAOYSA-N 2-[dithiocarboxy(methyl)amino]acetic acid Chemical compound SC(=S)N(C)CC(O)=O KEZYHIPQRGTUDU-UHFFFAOYSA-N 0.000 claims description 10
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 10
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 10
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 10
- 239000004005 microsphere Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229920002401 polyacrylamide Polymers 0.000 claims description 10
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 10
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 10
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 10
- 238000000498 ball milling Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims description 8
- 238000012986 modification Methods 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 238000002386 leaching Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 5
- 238000005070 sampling Methods 0.000 claims description 5
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 4
- 238000002203 pretreatment Methods 0.000 claims description 3
- 238000002715 modification method Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 abstract description 99
- 238000011084 recovery Methods 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 13
- 239000010409 thin film Substances 0.000 abstract description 7
- 238000001514 detection method Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
- 229960003022 amoxicillin Drugs 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- -1 cyanide halide ion Chemical class 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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CN202211009737.0A CN115073302B (zh) | 2022-08-23 | 2022-08-23 | 一种从副产母液中提取四丁基溴化铵的方法 |
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CN202211009737.0A CN115073302B (zh) | 2022-08-23 | 2022-08-23 | 一种从副产母液中提取四丁基溴化铵的方法 |
Publications (2)
Publication Number | Publication Date |
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CN115073302A true CN115073302A (zh) | 2022-09-20 |
CN115073302B CN115073302B (zh) | 2022-11-04 |
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CN202211009737.0A Active CN115073302B (zh) | 2022-08-23 | 2022-08-23 | 一种从副产母液中提取四丁基溴化铵的方法 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103360262A (zh) * | 2012-03-28 | 2013-10-23 | 盐城工学院 | 一种利用四丁基溴化铵结晶母液制备三丁胺的方法 |
JP2016044149A (ja) * | 2014-08-25 | 2016-04-04 | フタムラ化学株式会社 | テトラブチルアンモニウムアセテートの製造方法 |
CN113248393A (zh) * | 2021-05-17 | 2021-08-13 | 山东同成医药股份有限公司 | 一种四丁基溴化铵的合成方法 |
CN114605271A (zh) * | 2022-04-14 | 2022-06-10 | 河北海力香料股份有限公司 | 一种合成四丁基溴化铵的方法 |
-
2022
- 2022-08-23 CN CN202211009737.0A patent/CN115073302B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103360262A (zh) * | 2012-03-28 | 2013-10-23 | 盐城工学院 | 一种利用四丁基溴化铵结晶母液制备三丁胺的方法 |
JP2016044149A (ja) * | 2014-08-25 | 2016-04-04 | フタムラ化学株式会社 | テトラブチルアンモニウムアセテートの製造方法 |
CN113248393A (zh) * | 2021-05-17 | 2021-08-13 | 山东同成医药股份有限公司 | 一种四丁基溴化铵的合成方法 |
CN114605271A (zh) * | 2022-04-14 | 2022-06-10 | 河北海力香料股份有限公司 | 一种合成四丁基溴化铵的方法 |
Non-Patent Citations (1)
Title |
---|
郭良科等: "四丁基溴化铵的合成", 《应用化工》 * |
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Denomination of invention: A Method for Extracting Tetrabutylammonium Bromide from Byproduct Mother Liquor Effective date of registration: 20230524 Granted publication date: 20221104 Pledgee: Shandong Shouguang Rural Commercial Bank Co.,Ltd. Pledgor: SHANDONG TONGCHENG MEDICINE CO.,LTD. Registration number: Y2023980041503 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20221104 Pledgee: Shandong Shouguang Rural Commercial Bank Co.,Ltd. Pledgor: SHANDONG TONGCHENG MEDICINE CO.,LTD. Registration number: Y2023980041503 |