CN101585771A - 利用氟代反应综合利用一氯硝基苯混合物的方法 - Google Patents
利用氟代反应综合利用一氯硝基苯混合物的方法 Download PDFInfo
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- CN101585771A CN101585771A CN 200910100558 CN200910100558A CN101585771A CN 101585771 A CN101585771 A CN 101585771A CN 200910100558 CN200910100558 CN 200910100558 CN 200910100558 A CN200910100558 A CN 200910100558A CN 101585771 A CN101585771 A CN 101585771A
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- CN
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- Prior art keywords
- chloronitrobenzene
- mixture
- reaction
- comprehensive utilization
- fluoro
- 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.)
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- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 24
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 26
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 13
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 13
- 238000001953 recrystallisation Methods 0.000 claims abstract description 12
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 9
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims abstract description 7
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 claims description 12
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 claims description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- -1 tributyl benzyl Chemical group 0.000 claims description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- LQOBMKYCRQDMTN-UHFFFAOYSA-N 3-(2-ethylphenyl)pentan-3-amine;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1C(N)(CC)CC LQOBMKYCRQDMTN-UHFFFAOYSA-N 0.000 claims description 3
- 230000001546 nitrifying effect Effects 0.000 claims description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 235000011164 potassium chloride Nutrition 0.000 abstract 1
- 239000001103 potassium chloride Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000011084 recovery Methods 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HUFIRBOBXZUFPV-UHFFFAOYSA-N benzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1 HUFIRBOBXZUFPV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
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CN 200910100558 CN101585771B (zh) | 2009-07-07 | 2009-07-07 | 利用氟代反应综合利用一氯硝基苯混合物的方法 |
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CN 200910100558 CN101585771B (zh) | 2009-07-07 | 2009-07-07 | 利用氟代反应综合利用一氯硝基苯混合物的方法 |
Publications (2)
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CN101585771A true CN101585771A (zh) | 2009-11-25 |
CN101585771B CN101585771B (zh) | 2013-05-08 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101838203A (zh) * | 2010-05-19 | 2010-09-22 | 盘锦兴福化工有限公司 | 邻氟硝基苯的生产工艺 |
CN102875521A (zh) * | 2012-09-27 | 2013-01-16 | 中国海洋石油总公司 | 一种相转移催化制备氟代碳酸酯的方法 |
CN108586257A (zh) * | 2018-05-03 | 2018-09-28 | 浙江解氏新材料股份有限公司 | 一种对氟硝基苯的新型制备方法 |
CN109851471A (zh) * | 2019-01-24 | 2019-06-07 | 浙江本立科技股份有限公司 | 一种2,4-二氯氟苯的合成方法 |
CN110437073A (zh) * | 2018-05-03 | 2019-11-12 | 浙江解氏新材料股份有限公司 | 一种氯硝基苯间位油的综合开发分离方法 |
CN115850085A (zh) * | 2022-12-29 | 2023-03-28 | 中国科学技术大学苏州高等研究院 | 一种由氯代硝基苯制备氟代硝基苯的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101289396A (zh) * | 2008-05-30 | 2008-10-22 | 浙江富盛控股集团有限公司 | 一种邻、间、对硝基氯苯混合组分的分离利用方法 |
-
2009
- 2009-07-07 CN CN 200910100558 patent/CN101585771B/zh active Active
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101838203A (zh) * | 2010-05-19 | 2010-09-22 | 盘锦兴福化工有限公司 | 邻氟硝基苯的生产工艺 |
CN102875521A (zh) * | 2012-09-27 | 2013-01-16 | 中国海洋石油总公司 | 一种相转移催化制备氟代碳酸酯的方法 |
CN102875521B (zh) * | 2012-09-27 | 2014-08-13 | 中国海洋石油总公司 | 一种相转移催化制备氟代碳酸酯的方法 |
CN108586257A (zh) * | 2018-05-03 | 2018-09-28 | 浙江解氏新材料股份有限公司 | 一种对氟硝基苯的新型制备方法 |
CN110437073A (zh) * | 2018-05-03 | 2019-11-12 | 浙江解氏新材料股份有限公司 | 一种氯硝基苯间位油的综合开发分离方法 |
CN110437073B (zh) * | 2018-05-03 | 2022-04-29 | 浙江解氏新材料股份有限公司 | 一种氯硝基苯间位油的综合开发分离方法 |
CN109851471A (zh) * | 2019-01-24 | 2019-06-07 | 浙江本立科技股份有限公司 | 一种2,4-二氯氟苯的合成方法 |
CN109851471B (zh) * | 2019-01-24 | 2022-02-01 | 浙江本立科技股份有限公司 | 一种2,4-二氯氟苯的合成方法 |
CN115850085A (zh) * | 2022-12-29 | 2023-03-28 | 中国科学技术大学苏州高等研究院 | 一种由氯代硝基苯制备氟代硝基苯的方法 |
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CN101585771B (zh) | 2013-05-08 |
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Owner name: ZHEJIANG PROVINCE CHANGSHAN CHANGSHENG CHEMICAL IN Free format text: FORMER OWNER: ZHEJIANG FUSHENG HOLDING GROUP CO., LTD. Effective date: 20130306 |
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Effective date of registration: 20130306 Address after: 324200 eco industrial park, Changshan County, Zhejiang Applicant after: Zhejiang Changshan Changsheng Chemical Engineering Co.,Ltd. Address before: 324202 Changshan County Industrial Park, Zhejiang, Quzhou Applicant before: Zhejiang Fusheng Holding Group Co.,Ltd. |
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Denomination of invention: Method for Comprehensive Utilization of Monochloronitrobenzene Mixtures through Fluorination Reaction Effective date of registration: 20231205 Granted publication date: 20130508 Pledgee: Zhejiang Tailong commercial bank Limited by Share Ltd. Quzhou Changshan branch Pledgor: Zhejiang Changshan Changsheng Chemical Engineering Co.,Ltd. Registration number: Y2023980069219 |