CN111848332A - 一种间氯三氟甲苯新的合成工艺 - Google Patents
一种间氯三氟甲苯新的合成工艺 Download PDFInfo
- Publication number
- CN111848332A CN111848332A CN202010820577.2A CN202010820577A CN111848332A CN 111848332 A CN111848332 A CN 111848332A CN 202010820577 A CN202010820577 A CN 202010820577A CN 111848332 A CN111848332 A CN 111848332A
- Authority
- CN
- China
- Prior art keywords
- chlorotrifluoromethane
- layering
- triethylamine
- weighing
- synthesis process
- 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
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 24
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 69
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims abstract description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 238000005303 weighing Methods 0.000 claims abstract description 30
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 238000002474 experimental method Methods 0.000 claims abstract description 19
- 238000005070 sampling Methods 0.000 claims abstract description 19
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 11
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 11
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 11
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000010410 layer Substances 0.000 claims description 54
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229910001868 water Inorganic materials 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 17
- 238000004458 analytical method Methods 0.000 claims description 16
- 239000006227 byproduct Substances 0.000 claims description 15
- 239000001103 potassium chloride Substances 0.000 claims description 15
- 235000011164 potassium chloride Nutrition 0.000 claims description 15
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- SPIFDSWFDKNERT-UHFFFAOYSA-N nickel;hydrate Chemical compound O.[Ni] SPIFDSWFDKNERT-UHFFFAOYSA-N 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 239000005416 organic matter Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 3
- 239000011230 binding agent Substances 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002699 waste material Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 230000001276 controlling effect Effects 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- YTCGOUNVIAWCMG-UHFFFAOYSA-N 1-chloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Cl)=C1 YTCGOUNVIAWCMG-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000005858 Triflumizole Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CN202010820577.2A CN111848332B (zh) | 2020-08-14 | 2020-08-14 | 一种间氯三氟甲苯新的合成工艺 |
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CN202010820577.2A CN111848332B (zh) | 2020-08-14 | 2020-08-14 | 一种间氯三氟甲苯新的合成工艺 |
Publications (2)
Publication Number | Publication Date |
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CN111848332A true CN111848332A (zh) | 2020-10-30 |
CN111848332B CN111848332B (zh) | 2023-03-24 |
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CN202010820577.2A Active CN111848332B (zh) | 2020-08-14 | 2020-08-14 | 一种间氯三氟甲苯新的合成工艺 |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4849557A (en) * | 1987-05-13 | 1989-07-18 | Central Glass Company, Limited | Preparation of trifluoromethyltoluene from halomethylbenzotrifluoride |
US4885415A (en) * | 1987-08-03 | 1989-12-05 | Bayer Aktiengesellschaft | Process for the preparation of benzotrifluorides which are substituted by fluorine and optionally in addition by chlorine |
EP0506200A1 (en) * | 1991-03-27 | 1992-09-30 | Dowelanco | A process for the preparation of o-chlorofluorobenzene |
US5283378A (en) * | 1990-10-18 | 1994-02-01 | Bayer Aktiengesellschaft | Process for the dechlorination and/or debromination of fluorine-and chlorine- and/or bromine-containing aromatic compounds |
US6482996B1 (en) * | 1999-09-09 | 2002-11-19 | Bayer Aktiengesellschaft | Method for the production or preparation of 2,6-dichlorotoluol |
CN111153758A (zh) * | 2019-06-19 | 2020-05-15 | 浙江大学 | 利用负载型金属氧化物催化芳香族含卤有机物脱卤的方法 |
-
2020
- 2020-08-14 CN CN202010820577.2A patent/CN111848332B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4849557A (en) * | 1987-05-13 | 1989-07-18 | Central Glass Company, Limited | Preparation of trifluoromethyltoluene from halomethylbenzotrifluoride |
US4885415A (en) * | 1987-08-03 | 1989-12-05 | Bayer Aktiengesellschaft | Process for the preparation of benzotrifluorides which are substituted by fluorine and optionally in addition by chlorine |
US5283378A (en) * | 1990-10-18 | 1994-02-01 | Bayer Aktiengesellschaft | Process for the dechlorination and/or debromination of fluorine-and chlorine- and/or bromine-containing aromatic compounds |
EP0506200A1 (en) * | 1991-03-27 | 1992-09-30 | Dowelanco | A process for the preparation of o-chlorofluorobenzene |
US6482996B1 (en) * | 1999-09-09 | 2002-11-19 | Bayer Aktiengesellschaft | Method for the production or preparation of 2,6-dichlorotoluol |
CN111153758A (zh) * | 2019-06-19 | 2020-05-15 | 浙江大学 | 利用负载型金属氧化物催化芳香族含卤有机物脱卤的方法 |
Non-Patent Citations (2)
Title |
---|
MASASHI TASHIRO ET AL.: "REDUCTIVE DEHALOGENATION OF HALOACETOPHENONES WITH RANEY ALLOYS IN ALKALINE SOLUTION", 《ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL》 * |
李红运等: "间氯三氟甲苯的制备", 《南京工业大学学报(自然科学版)》 * |
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Publication number | Publication date |
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CN111848332B (zh) | 2023-03-24 |
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Effective date of registration: 20240514 Address after: 735000, No. 9 Xingfu Road, Yumen East Town, Yumen City, Jiuquan City, Gansu Province Patentee after: Yumen Joins Hands with Zhongcheng Management Partnership Enterprise (Limited Partnership) Country or region after: China Address before: Room 201, Unit 5, Building 1, No. 688, Qiushi Road, Jinshanwei Town, Jinshan District, Shanghai, 201599 Patentee before: Shanghai Jiahua Technology Co.,Ltd. Country or region before: China |