CN115557827A - Preparation method of 3-chloro-3,3-difluoropropylene - Google Patents
Preparation method of 3-chloro-3,3-difluoropropylene Download PDFInfo
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- CN115557827A CN115557827A CN202211040543.7A CN202211040543A CN115557827A CN 115557827 A CN115557827 A CN 115557827A CN 202211040543 A CN202211040543 A CN 202211040543A CN 115557827 A CN115557827 A CN 115557827A
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- chloro
- difluoropropene
- difluoropropane
- dichloro
- phase transfer
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- AQBMNBSTXOCKKZ-UHFFFAOYSA-N 3-chloro-3,3-difluoroprop-1-ene Chemical group FC(F)(Cl)C=C AQBMNBSTXOCKKZ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- WGABYHBTXHBSEI-UHFFFAOYSA-N 1,3-dichloro-1,1-difluoropropane Chemical compound FC(F)(Cl)CCCl WGABYHBTXHBSEI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 14
- 239000012670 alkaline solution Substances 0.000 claims abstract description 8
- 150000003983 crown ethers Chemical group 0.000 claims abstract description 5
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
- 238000007033 dehydrochlorination reaction Methods 0.000 claims abstract description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000002202 Polyethylene glycol Chemical group 0.000 claims description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 4
- 229920001223 polyethylene glycol Chemical group 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 3
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 claims description 2
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 claims description 2
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 claims description 2
- 239000004353 Polyethylene glycol 8000 Substances 0.000 claims description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims description 2
- 229940057838 polyethylene glycol 4000 Drugs 0.000 claims description 2
- 229940093429 polyethylene glycol 6000 Drugs 0.000 claims description 2
- 229940085678 polyethylene glycol 8000 Drugs 0.000 claims description 2
- 235000019446 polyethylene glycol 8000 Nutrition 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 claims description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 2
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000003637 basic solution Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract description 3
- 239000004721 Polyphenylene oxide Chemical group 0.000 abstract 1
- 229920000570 polyether Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 1-bromo-3-chloro-1,1-difluoropropane Chemical compound 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention discloses a preparation method of 3-chloro-3,3-difluoropropene. The disclosed method comprises the dehydrochlorination reaction of 1,3-dichloro-1,1-difluoropropane in an alkaline solution to generate 3-chloro-3,3-difluoropropene under the action of a phase transfer catalyst, wherein the phase transfer catalyst is 1,3-dichloro-1,1-difluoropropane, the mass of the phase transfer catalyst is 0.5-5%, the molar ratio of alkali to 1,3-dichloro-1,1-difluoropropane is 1-5:1, the reaction temperature is 60-150 ℃, and the phase transfer catalyst is crown ether, quaternary ammonium salt, quaternary phosphonium salt or polyether. The preparation method has high product selectivity.
Description
Technical Field
The invention provides a preparation method of 3-chloro-3,3-difluoropropene, and particularly relates to a method for preparing 3-chloro-3,3-difluoropropene by taking 1,3-dichloro-1,1-difluoropropane as a raw material.
Background
In recent years, research on the synthesis of fluorine-containing compounds has been a hot area of international social attention. Fluorine atom is used as the element with the strongest electron-withdrawing ability, forms a C-F bond with strong bond energy with carbon atom, has the atomic radius similar to that of hydrogen atom, and can obviously change the physical and chemical properties and the biological activity of the compound after the atom is introduced into an organic matter.
3-chlorine-3,3-difluoropropene is a fluorine-containing chemical, can be used as a novel refrigerant or an intermediate of a foaming agent, and has important value in research on a preparation method of the fluorine-containing chemical. The existing synthesis method is to dissolve 1-bromo-3-chloro-1,1-difluoropropane in an ethanol solvent, and dropwise add a low-temperature potassium hydroxide ethanol liquid (10%) to prepare 3-chloro-3,3-difluoropropene, and the selectivity of the method is only 78%.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method of 3-chloro-3,3-difluoropropene.
Therefore, the preparation method provided by the invention comprises the following steps: under the action of a phase transfer catalyst, 1,3-dichloro-1,1-difluoropropane is subjected to dehydrochlorination reaction in an alkaline solution to prepare 3-chloro-3,3-difluoropropene, wherein the reaction temperature is 60-150 ℃; the phase transfer catalyst is crown ether, quaternary ammonium salt, quaternary phosphonium salt or polyethylene glycol; the alkaline solution is sodium hydroxide aqueous solution or potassium hydroxide aqueous solution.
Optionally, the mass of the phase transfer catalyst is 1,3-dichloro-1,1-difluoropropane, which is 0.5% -5%, and the molar ratio of the alkali of the alkaline solution to 1,3-dichloro-1,1-difluoropropane is 1-5:1.
Optionally, the reaction time is 1-24 h.
Optionally, the crown ether is cyclodextrin.
Optionally, the quaternary ammonium salt is tetrabutylammonium chloride, tetrabutylammonium bromide, benzyltriethylammonium chloride or dodecyltrimethylammonium chloride.
Optionally, the quaternary phosphonium salt is triphenylphosphine, tetrabutylphosphonium bromide, hexadecyltributylphosphonium bromide, methyltriphenylphosphonium bromide or tetrabutylphosphonium acetate.
Optionally, the polyethylene glycol is polyethylene glycol-4000, polyethylene glycol-6000 or polyethylene glycol-8000.
Optionally, the mass of the phase transfer catalyst is 1-2% of that of 1,3-dichloro-1,1-difluoropropane, the alkaline solution is a potassium hydroxide aqueous solution, and the mass concentration of the potassium hydroxide aqueous solution is 40-60%.
Optionally, the molar ratio of the alkali to 1,3-dichloro-1,1-difluoropropane is 1.2 to 1.5.
Optionally, the reaction temperature is 80-120 ℃, and the reaction time is 5-10 h.
Compared with the prior art, the invention adopts the phase transfer catalyst, the conversion rate of the raw materials is high, and the selectivity can reach 99.8 percent under better conditions.
Drawings
FIG. 1 is a GC-MS spectrum of 3-chloro-3,3-difluoropropene prepared in example 1.
Detailed Description
Unless otherwise defined, scientific and technical terms used herein are to be understood as commonly understood by one of ordinary skill in the relevant art. It is also understood that the temperatures, concentrations referred to herein are approximate values and are for illustrative purposes. Although methods and materials similar or equivalent to those described herein can be used in the practice of the present disclosure, suitable methods and materials are described in part below. Publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, to the extent that conflicts arise, herein. In addition, the materials, methods, solution concentrations, and examples are illustrative only and not intended to be limiting. In a specific scheme, a person skilled in the art can optimize the material ratio, concentration and operation parameter values involved in the method in a conventional experimental period according to the disclosure of the invention to achieve the purpose of the invention.
The present invention is further illustrated by the following specific examples, which are not intended to limit the invention in any way. In the following examples, GC-MS detection was used for the conversion and selectivity detection of the reactants.
Example 1:
100g of 50 percent (mass percent) KOH aqueous solution, 60g of 1, 3-dichloro-1,1-difluoropropane and 6g of cyclodextrin (1 wt percent) are sequentially put into a reaction kettle with a stirrer; the stirring is started, the reaction temperature is controlled at 100 ℃, after 10 hours of reaction, the reaction materials are cooled to room temperature, and after phase separation, organic matters are collected for gas chromatography analysis, the result shows that the conversion rate of 1,3-dichloro-1,1-difluoropropane is 99.0 percent, and the selectivity of 3-chloro-3,3-difluoropropene is 99.8 percent.
GC-MS detection of the product 3-chloro-3,3-difluoropropene showed the mass spectrum results shown in FIG. 1. The correlation peaks are attributed as follows: m/z113 is a molecular ion peak, m/z93 is CClF 2 CH＝CH 2 Ion peak after F removal, m/z85 is trifluorochloromethyl, m/z77 is CClF 2 CH＝CH 2 Ion peak after dechlorination, m/z51 is difluoromethyl; the above data demonstrate that the product obtained is 3-chloro-3,3-difluoropropene.
Examples 2 to 13:
examples 2 to 13 3-chloro-3,3-difluoropropene was prepared in the same manner as in example 1, except that the kind and content of the phase transfer catalyst, the reaction temperature and the reaction time were changed, and the reaction results were as shown in table 2.
TABLE 2
Example 14:
example 14 3-chloro-3,3-difluoropropene was prepared by the same procedure as in example 1, except that the lye concentration was changed to aqueous NaOH, and the results showed 98.5% conversion of 1,3-dichloro-1,1-difluoropropane and 97.8% selectivity to 3-chloro-3,3-difluoropropene.
Examples 15 to 20:
examples 15 to 20 3-chloro-3,3-difluoropropene was prepared in the same manner as in example 1, except that the lye concentration, the molar ratio of base to 1,3-dichloro-1,1-difluoropropane were varied and the reaction results are shown in table 3.
TABLE 3
The above description is only a partial example of the present invention, and is not intended to limit the present invention in any way, and any simple modifications, equivalent changes and modifications made to the above embodiment according to the technical essence of the present invention are within the technical scope of the present invention.
Claims (10)
1. A preparation method of 3-chloro-3,3-difluoropropene is characterized by comprising the following steps: under the action of a phase transfer catalyst, 1,3-dichloro-1,1-difluoropropane is subjected to dehydrochlorination reaction in an alkaline solution to prepare 3-chloro-3,3-difluoropropene, wherein the reaction temperature is 60-150 ℃; the phase transfer catalyst is crown ether, quaternary ammonium salt, quaternary phosphonium salt or polyethylene glycol; the alkaline solution is sodium hydroxide aqueous solution or potassium hydroxide aqueous solution.
2. The process for the preparation of 3-chloro-3,3-difluoropropene of claim 1 wherein the mass of said phase transfer catalyst is 0.5% to 5% of the mass of 1,3-dichloro-1,1-difluoropropane and the molar ratio of base of said basic solution to 1,3-dichloro-1,1-difluoropropane is 1 to 5:1.
3. The process for preparing 3-chloro-3,3-difluoropropene of claim 1 wherein the reaction time is 1 to 24 hours.
4. The method of making 3-chloro-3,3-difluoropropene according to claim 1, wherein said crown ether is a cyclodextrin.
5. The method of claim 1, wherein the quaternary ammonium salt is tetrabutylammonium chloride, tetrabutylammonium bromide, benzyltriethylammonium chloride or dodecyltrimethylammonium chloride.
6. The process for preparing 3-chloro-3,3-difluoropropene as claimed in claim 1, wherein said quaternary phosphonium salt is triphenylphosphine, tetrabutylphosphonium bromide, hexadecyltributylphosphonium bromide, methyltriphenylphosphonium bromide or tetrabutylphosphonium acetate.
7. The method of claim 1, wherein the polyethylene glycol is polyethylene glycol-4000, polyethylene glycol-6000 or polyethylene glycol-8000.
8. The method for preparing 3-chloro-3,3-difluoropropene according to claim 1, wherein the mass of the phase transfer catalyst is 1% -2% of that of 1,3-dichloro-1,1-difluoropropane, the alkaline solution is an aqueous solution of potassium hydroxide, and the concentration of the aqueous solution of potassium hydroxide is 40% -60%.
9. The process for the preparation of 3-chloro-3,3-difluoropropene of claim 1 wherein the molar ratio of said base to 1,3-dichloro-1,1-difluoropropane is 1.2 to 1.5.
10. The method for preparing 3-chloro-3,3-difluoropropene according to claim 1, wherein the reaction temperature is 80 ℃ to 120 ℃ and the reaction time is 5h to 10h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211040543.7A CN115557827A (en) | 2022-08-29 | 2022-08-29 | Preparation method of 3-chloro-3,3-difluoropropylene |
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| CN202211040543.7A CN115557827A (en) | 2022-08-29 | 2022-08-29 | Preparation method of 3-chloro-3,3-difluoropropylene |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864570A (en) * | 2012-12-18 | 2014-06-18 | 中化蓝天集团有限公司 | Preparation method of 1-chloro-3,3,3-trifluoropropene |
| CN105753636A (en) * | 2014-12-13 | 2016-07-13 | 西安近代化学研究所 | Separation method of 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene |
| WO2019203318A1 (en) * | 2018-04-19 | 2019-10-24 | Ａｇｃ株式会社 | Method for producing fluoroolefin |
| CN113527040A (en) * | 2020-04-22 | 2021-10-22 | 浙江省化工研究院有限公司 | Preparation method of halogenated propylene |
-
2022
- 2022-08-29 CN CN202211040543.7A patent/CN115557827A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864570A (en) * | 2012-12-18 | 2014-06-18 | 中化蓝天集团有限公司 | Preparation method of 1-chloro-3,3,3-trifluoropropene |
| CN105753636A (en) * | 2014-12-13 | 2016-07-13 | 西安近代化学研究所 | Separation method of 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene |
| WO2019203318A1 (en) * | 2018-04-19 | 2019-10-24 | Ａｇｃ株式会社 | Method for producing fluoroolefin |
| CN113527040A (en) * | 2020-04-22 | 2021-10-22 | 浙江省化工研究院有限公司 | Preparation method of halogenated propylene |
Non-Patent Citations (2)
| Title |
|---|
| R. N. HASZELDINE: "Fluoro-olefins. Part II. Synthesis and Reactions of Some 3:3:3-Trihalogenopropenes", JOURNAL OF THE CHEMICAL SOCIETY, 1 January 1953 (1953-01-01), pages 3371 - 3378 * |
| 徐卫国等: "一种1, 2-二溴-1, 1-二氯-2, 2-二氟乙烷的制备新方法", 化工生产与技术, vol. 13, no. 3, 30 June 2006 (2006-06-30), pages 6 - 7 * |
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