CN106588958A - 一种连续制备炔醇双格氏试剂的生产系统及方法 - Google Patents
一种连续制备炔醇双格氏试剂的生产系统及方法 Download PDFInfo
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- CN106588958A CN106588958A CN201510661573.3A CN201510661573A CN106588958A CN 106588958 A CN106588958 A CN 106588958A CN 201510661573 A CN201510661573 A CN 201510661573A CN 106588958 A CN106588958 A CN 106588958A
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- alkynol
- grignard reagent
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- 239000000463 material Substances 0.000 claims abstract description 40
- 230000005484 gravity Effects 0.000 claims abstract description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 119
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- 239000003153 chemical reaction reagent Substances 0.000 claims description 29
- 238000002156 mixing Methods 0.000 claims description 19
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 8
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- 238000007599 discharging Methods 0.000 claims description 7
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002826 coolant Substances 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 2
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
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- 238000001514 detection method Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
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- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 description 1
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- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
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- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110642671A (zh) * | 2019-09-25 | 2020-01-03 | 上海应用技术大学 | 一种连续制备格氏试剂合成苯乙醇的系统和方法 |
CN110914237A (zh) * | 2017-07-20 | 2020-03-24 | 帝斯曼知识产权资产管理有限公司 | 生产3,7-二甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-壬-2z,7e-二烯-4-炔-1,6-二醇的方法 |
WO2020078262A1 (zh) * | 2018-10-19 | 2020-04-23 | 上虞新和成生物化工有限公司 | 一种格氏反应金属有机产物的绿色水解工艺 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1752062A (zh) * | 2005-10-27 | 2006-03-29 | 浙江大学 | 合成α-官能团化多取代烯丙醇的方法 |
CN101039889A (zh) * | 2004-05-24 | 2007-09-19 | 环球油品公司 | 具有固体催化剂再生和芳族副产物脱除的烷基化芳族化合物的方法 |
CN101294093A (zh) * | 2007-04-29 | 2008-10-29 | 华中农业大学 | 生物柴油的一体化生产工艺及专用装置 |
WO2010117285A2 (en) * | 2009-04-07 | 2010-10-14 | Zaklady Farmaceutyczne Polpharma Sa | Process for the preparation of grignard compounds |
CN102336643A (zh) * | 2011-07-13 | 2012-02-01 | 北京博源恒升高科技有限公司 | 苯酚类直接氧化合成苯醌类的工艺 |
CN103896737A (zh) * | 2014-03-31 | 2014-07-02 | 南京工业大学 | 一种利用微结构反应器制备炔丙醇的方法 |
CN104031747A (zh) * | 2014-06-13 | 2014-09-10 | 太原理工大学 | 一种生物柴油的生产装置及生产方法 |
CN203960096U (zh) * | 2014-07-10 | 2014-11-26 | 新化县诺威生物科技有限责任公司 | 格利雅试剂生产装置 |
-
2015
- 2015-10-14 CN CN201510661573.3A patent/CN106588958B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101039889A (zh) * | 2004-05-24 | 2007-09-19 | 环球油品公司 | 具有固体催化剂再生和芳族副产物脱除的烷基化芳族化合物的方法 |
CN1752062A (zh) * | 2005-10-27 | 2006-03-29 | 浙江大学 | 合成α-官能团化多取代烯丙醇的方法 |
CN101294093A (zh) * | 2007-04-29 | 2008-10-29 | 华中农业大学 | 生物柴油的一体化生产工艺及专用装置 |
WO2010117285A2 (en) * | 2009-04-07 | 2010-10-14 | Zaklady Farmaceutyczne Polpharma Sa | Process for the preparation of grignard compounds |
CN102336643A (zh) * | 2011-07-13 | 2012-02-01 | 北京博源恒升高科技有限公司 | 苯酚类直接氧化合成苯醌类的工艺 |
CN103896737A (zh) * | 2014-03-31 | 2014-07-02 | 南京工业大学 | 一种利用微结构反应器制备炔丙醇的方法 |
CN104031747A (zh) * | 2014-06-13 | 2014-09-10 | 太原理工大学 | 一种生物柴油的生产装置及生产方法 |
CN203960096U (zh) * | 2014-07-10 | 2014-11-26 | 新化县诺威生物科技有限责任公司 | 格利雅试剂生产装置 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110914237A (zh) * | 2017-07-20 | 2020-03-24 | 帝斯曼知识产权资产管理有限公司 | 生产3,7-二甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-壬-2z,7e-二烯-4-炔-1,6-二醇的方法 |
WO2020078262A1 (zh) * | 2018-10-19 | 2020-04-23 | 上虞新和成生物化工有限公司 | 一种格氏反应金属有机产物的绿色水解工艺 |
CN111072451A (zh) * | 2018-10-19 | 2020-04-28 | 上虞新和成生物化工有限公司 | 一种格氏反应金属有机产物的绿色水解工艺 |
CN111072451B (zh) * | 2018-10-19 | 2021-04-02 | 上虞新和成生物化工有限公司 | 一种格氏反应金属有机产物的水解工艺 |
CN110642671A (zh) * | 2019-09-25 | 2020-01-03 | 上海应用技术大学 | 一种连续制备格氏试剂合成苯乙醇的系统和方法 |
CN110642671B (zh) * | 2019-09-25 | 2022-08-23 | 上海应用技术大学 | 一种连续制备格氏试剂合成苯乙醇的系统和方法 |
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