CN108264458B - Preparation method of hexafluoropropylene oxide dimer - Google Patents
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- C07C51/58—Preparation of carboxylic acid halides
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
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Abstract
The present invention relates to a method for producing a hexafluoropropylene oxide dimer, which comprises: in a polar aprotic solvent, hexafluoropropylene oxide is used as a raw material, a phase transfer agent is added, a composite catalytic system consisting of tertiary amine and diamine is used as a catalyst, and the hexafluoropropylene oxide dimer is obtained through reaction. The preparation method of the hexafluoropropylene oxide dimer provided by the invention has the advantages of high selectivity, mild reaction conditions, recyclable solvent and catalyst, simple and feasible operation method, environmental friendliness, easy industrial control and suitability for large-scale industrial production.
Description
Technical Field
The invention belongs to the technical field of fluorine-containing fine chemical engineering, and particularly relates to a preparation method of hexafluoropropylene oxide dimer.
Background
The fluorine-containing compound is one of the most rapidly-growing chemicals in the field of fine chemical engineering, has wide application in the fields of chemistry, chemical engineering, materials, pesticides, medicines and the like, and has wide development prospect and strong vitality. The hexafluoropropylene oxide dimer is colorless and transparent liquid at normal temperature, is a perfluoro active intermediate, can be used for introducing organic fluorine groups into organic molecules, and is used in pesticide and pharmaceutical industry. In the field of materials, the hexafluoropropylene oxide dimer is widely applied, and the terminal acyl fluoride active functional group can be modified to prepare fluorine treating agents such as fluorocarbon surfactant and the like with excellent performance; the high-performance perfluoropolyether can be prepared by continuously polymerizing the hexafluoropropylene oxide dimer, and is lubricating oil with excellent high-temperature resistance; the hexafluoropropylene oxide dimer can be used for preparing perfluoro-n-propyl vinyl ether (PPVE) after hydrolysis and decarboxylation, and can be used for synthesis and modification of fluorine-containing resin.
At present, there are few patents on the preparation method of hexafluoropropylene oxide dimer. In DE 2026669, silver nitrate is used as catalyst, the dimer yield can reach 86% at most, but silver nitrate has lightSensitivity and stability are poor, nitrous acid gas is easy to generate, and operation safety is low. In Japanese patent JP 62195345, cesium fluoride is used as a catalyst, and water or PEG is added in different amounts to prepare hexafluoropropylene oxide oligomer, and this process has low selectivity of hexafluoropropylene oxide dimer in the product and needs to be carried out at-20 deg.C, which is difficult to operate practically. In addition, the catalyst cesium fluoride is expensive and easy to absorb water, so that the large-scale production is not facilitated. The use of transition metal salts such as CuCl, CuCl is mentioned by the company Herchester in Chinese patent CN 10440922，CoCl2，ZnCl2The yield of hexafluoropropylene oxide dimer is about 80% in a catalytic system formed by the catalyst and tertiary diamine, but transition metal ions are used in the catalyst, so that the catalyst is difficult to recover and is easy to cause environmental pollution. Japanese patent JP 1990-259833 mentions that tertiary amines or pyridine or quinoline and urea are used as catalysts and a gas mixture of hexafluoropropylene oxide and hexafluoropropylene is used as a raw material in a certain ratio, and the yield of hexafluoropropylene oxide dimer obtained is not high, and gaseous by-products are generated, which increases the difficulty of practical operation.
Disclosure of Invention
Aiming at the problems of poor catalyst stability, low product selectivity, high operation difficulty, environmental unfriendliness and the like in the prior art, the invention discloses a simple and feasible preparation method of hexafluoropropylene oxide dimer, which comprises the following steps: in a polar aprotic solvent, hexafluoropropylene oxide is used as a raw material, a phase transfer agent is added, a composite catalytic system consisting of tertiary amine and tertiary diamine is used as a catalyst, and the hexafluoropropylene oxide dimer is obtained through reaction.
More specifically, the preparation method of the hexafluoropropylene oxide dimer comprises the following steps:
1) adding a composite catalytic system consisting of a polar aprotic solvent, tertiary amine and tertiary diamine as a catalyst and a phase transfer agent into a reaction vessel, and stirring for 0.5-1 h at room temperature;
2) controlling the pressure in the reaction vessel to be-1.0 Mpa, adding a hexafluoropropylene oxide monomer into the reaction vessel, controlling the temperature to be 20-30 ℃, and reacting for 0.5-5 h;
3) after the reaction is finished, taking out the reaction liquid, and rectifying and separating the product to obtain hexafluoropropylene oxide dimer;
4) recovering the solvent and the catalyst.
In some embodiments, the hexafluoropropylene oxide monomer is added through the bottom of the reaction vessel after being connected with a gas flow meter, and the feeding rate is 1-20 g/min, preferably 5-10 g/min.
In some embodiments, the phase transfer agent is a quaternary ammonium fluoride salt; further, the phase transfer agent is one or more of tetramethylammonium fluoride, tetraethylammonium fluoride, tetrapropylammonium fluoride or tetrabutylammonium fluoride.
In some embodiments, the tertiary amine has the formula (I):
wherein R is1、R2、R3Each independently is C1-C12A saturated or unsaturated hydrocarbon group of (a);
further, R1、R2、R3Each independently is C1-C6Alkyl of (C)1-C6Cycloalkyl or phenyl.
In some embodiments, the tertiary diamine has the structural formula (II):
wherein R is C1-C12A saturated or unsaturated hydrocarbon group or a carbonyl group; r4～R7Each independently is C1-C12A saturated or unsaturated hydrocarbon group of (a); further, R, R4～R7Are each independently C1-C6Alkyl of (C)1-C6Cycloalkyl groups of (a); further, R is ethyl or carbonyl, R4～R7Each independently is methyl or ethyl.
In some embodiments, the polar aprotic solvent is one or more of tetraglyme, diglyme, acetonitrile, propionitrile, or tetrahydrofuran.
In some embodiments, the molar ratio of tertiary amine to tertiary diamine in the composite catalytic system is 1-10: 1, preferably 5-10: 1; the concentration of the tertiary amine is 0.5-5 mol/L, preferably 1-3 mol/L.
In some embodiments, the molar ratio of the tertiary amine to the phase transfer agent is 1 to 10:1, preferably 1 to 5: 1.
In some embodiments, the solvent and catalyst recovered after the reaction is completed can be recycled.
Compared with the existing hexafluoropropylene oxide dimer synthesis technology, the hexafluoropropylene oxide dimer obtained by the invention has the advantages of high selectivity, mild reaction conditions, recyclable solvent and catalyst, simple and easy operation method, environmental friendliness, easy industrial control and suitability for large-scale industrial production.
Definition of terms
The invention is intended to cover alternatives, modifications and equivalents, which may be included within the scope of the invention as defined by the appended claims. Those skilled in the art will recognize that many methods and materials similar or equivalent to those described herein can be used in the practice of the present invention. The present invention is in no way limited to the methods and materials described herein. In the event that one or more of the incorporated documents, patents, and similar materials differ or contradict this application (including but not limited to defined terminology, application of terminology, described techniques, and the like), this application controls.
It will be further appreciated that certain features of the invention, which are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention which are, for brevity, described in the context of a single embodiment, may also be provided separately or in any suitable subcombination.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. All patents and publications referred to herein are incorporated by reference in their entirety.
The following definitions as used herein should be applied unless otherwise indicated. For the purposes of the present invention, the chemical elements are in accordance with the CAS version of the periodic Table of elements, and the 75 th version of the handbook of chemistry and Physics, 1994. In addition, general principles of Organic Chemistry can be referred to as described in "Organic Chemistry", Thomas Sorrell, University Science Books, Sausaltito: 1999, and "March's Advanced Organic Chemistry" by Michael B.Smith and Jerry March, John Wiley & Sons, New York:2007, the entire contents of which are incorporated herein by reference.
The term "comprising" or "comprises" is open-ended, i.e. comprising what is specified in the present invention, but not excluding other aspects.
The term "room temperature" means a temperature range of 25. + -. 5 ℃.
In the context of the present invention, all numbers disclosed herein are approximate values, regardless of whether the word "about" or "approximately" is used. The numerical value of each figure may differ by 1%, 2%, or 5%.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the following further discloses some non-limiting examples to further explain the present invention in detail.
The reagents used in the present invention are either commercially available or prepared by methods known in the art or by methods described herein.
In the present invention, h represents hour, g represents g, mL represents mL, and mmol represents mmol.
Comparative example
N, N-dimethylaniline (24.2g), tetramethylurea (4.6g) and acetonitrile (100mL) were charged to a 2L jacketed reaction vessel equipped with a condensing jacket, and stirred at room temperature for 1 h. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 10g/min, stirring for reaction, connecting a constant temperature refrigerating pump outside a jacket of the reaction kettle, maintaining the temperature in the kettle to be about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. The crude product was taken out from the reaction vessel, and the product was isolated by rectification to give hexafluoropropylene oxide dimer (308g) in a yield of 61.6% and a purity of 98.89% by GC test.
Example 1
Triethylamine (20.2g), tetramethylethylenediamine (4.6g), tetramethylammonium fluoride (9.3g) and tetrahydrofuran (100mL) were charged in a 2L reaction vessel equipped with a condensing jacket, and stirred at room temperature for 1 hour. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 10g/min, stirring for reaction, introducing condensed water into a jacket of the reaction kettle, maintaining the temperature in the kettle at about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (412g) was obtained in 82.4% yield with 98.85% purity by GC.
Example 2
N, N-dimethylaniline (24.2g), tetramethylethylenediamine (4.6g), tetraethylammonium fluoride (14.9g) and acetonitrile (100mL) were charged to a 2L jacketed reaction vessel equipped with a condensation jacket and stirred at room temperature for 0.5 h. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 5g/min, stirring for reaction, introducing condensed water into a jacket of the reaction kettle, maintaining the temperature in the kettle at about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (436g) was obtained in 87.2% yield and 99.03% purity by GC test.
Example 3
N, N-dimethylaniline (24.2g), tetramethylurea (4.6g), tetramethylammonium fluoride (9.3g) and acetonitrile (100mL) were charged into a 2L jacketed reaction vessel equipped with a condensation jacket, and stirred at room temperature for 1 h. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 10g/min, stirring for reaction, introducing condensed water into a jacket of the reaction kettle, maintaining the temperature in the kettle at about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (453g) was obtained in 90.6% yield and 99.12% purity by GC.
Example 4
N, N-diethylaniline (29.8g), tetramethylpropanediamine (5.2g), tetrabutylammonium fluoride (10.3g) and tetraglyme (100mL) were charged into a 2L jacketed reaction vessel equipped with a condensation jacket, and stirred at room temperature for 0.5 h. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 10g/min, stirring for reaction, introducing condensed water into a jacket of the reaction kettle, maintaining the temperature in the kettle at about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (377g) was obtained in 75.4% yield and 98.82% purity by GC test.
Example 5
N, N-diethylaniline (29.8g), tetraethylethylenediamine (6.9g), tetrapropylammonium fluoride (13g) and propionitrile (100mL) were charged to a 2L jacketed reaction vessel with a condensation jacket and stirred at room temperature for 1 h. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 10g/min, stirring for reaction, introducing condensed water into a jacket of the reaction kettle, maintaining the temperature in the kettle at about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (406g) was obtained in 81.2% yield and 99.07% purity by GC test.
Example 6
N, N-dimethylaniline (24.2g), tetraethylethylenediamine (6.9g), tetramethylammonium fluoride (9.3g) and diethylene glycol dimethyl ether (100mL) were charged in a 2L reaction vessel equipped with a condensation jacket, and stirred at room temperature for 1 hour. Pumping the reaction kettle to-0.1 Mpa, introducing hexafluoropropylene oxide monomer into the reaction kettle at the speed of 10g/min, stirring for reaction, introducing condensed water into a jacket of the reaction kettle, maintaining the temperature in the kettle at about 25 ℃, stopping introducing hexafluoropropylene oxide monomer (500g), and stirring for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (382g) was obtained in 76.4% yield and 98.67% purity by GC test.
Example 7
The solvent and the catalyst recovered in example 3 were mixed by about 100mL, acetonitrile (20mL) was added thereto, the mixture was pumped into a 2L reaction vessel equipped with a condensing jacket, the reaction vessel was evacuated to-0.1 MPa, hexafluoropropylene oxide monomer was introduced into the reaction vessel at a rate of 10g/min, the reaction was stirred, condensed water was introduced into the jacket of the reaction vessel, the temperature in the reaction vessel was maintained at about 25 ℃, and after introducing hexafluoropropylene oxide monomer (500g), the introduction was stopped, and the reaction was stirred for 3 hours. Taking the crude product out of the reaction kettle, rectifying and separating the product, and recovering the solvent and the catalyst. Hexafluoropropylene oxide dimer (447g) was obtained in 89.4% yield and 99.01% purity by GC test (the process was repeated 7 times more after recycling).
While the methods of the present invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications of the methods and applications described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of the present invention within the context, spirit and scope of the invention. Those skilled in the art can modify the process parameters appropriately to achieve the desired results with reference to the disclosure herein. It is expressly intended that all such similar substitutes and modifications which would be obvious to those skilled in the art are deemed to be included within the invention.
Claims (7)
1. A process for the preparation of hexafluoropropylene oxide dimer, comprising: in a polar aprotic solvent, hexafluoropropylene oxide is taken as a raw material, a phase transfer agent is added, a composite catalytic system consisting of tertiary amine and tertiary diamine is taken as a catalyst, and hexafluoropropylene oxide dimer is obtained through reaction; wherein the phase transfer agent is a quaternary ammonium fluoride salt;
the tertiary amine has the structural formula shown as the following formula (I):
wherein, R is1、R2、R3Each independently is C1-C6Alkyl of (C)1-C6Cycloalkyl or phenyl of (a);
the tertiary diamine has the structural formula (II):
wherein R is C1-C12A saturated or unsaturated hydrocarbon group of (a); r4～R7Each independently is C1-C12Saturated or unsaturated hydrocarbon groups of (a).
2. The process for producing a hexafluoropropylene oxide dimer according to claim 1, comprising the steps of:
1) adding a composite catalytic system consisting of a polar aprotic solvent, tertiary amine and tertiary diamine as a catalyst and a phase transfer agent into a reaction vessel, and stirring for 0.5-1 h at room temperature;
2) controlling the pressure in the reaction vessel to be-1.0 Mpa, adding a hexafluoropropylene oxide monomer into the reaction vessel, controlling the temperature to be 20-30 ℃, and reacting for 0.5-5 h;
3) after the reaction is finished, taking out the reaction liquid, and rectifying and separating the product to obtain hexafluoropropylene oxide dimer;
4) recovering the solvent and the catalyst.
3. The method for producing a hexafluoropropylene oxide dimer according to claim 1 or 2, wherein a hexafluoropropylene oxide monomer is added through the bottom of the reaction vessel after being connected to a gas flow meter, and a feeding rate is 1 to 20 g/min.
4. The method for producing a hexafluoropropylene oxide dimer according to claim 3, wherein the feed rate is 5 to 10 g/min.
5. The method for producing a hexafluoropropylene oxide dimer according to claim 1 or 2, wherein the quaternary ammonium fluoride salt is one or more of tetramethylammonium fluoride, tetraethylammonium fluoride, tetrapropylammonium fluoride or tetrabutylammonium fluoride.
6. The method for producing a hexafluoropropylene oxide dimer according to claim 1 or 2, wherein the polar aprotic solvent is one or more of tetraglyme, diglyme, acetonitrile, propionitrile or tetrahydrofuran.
7. The method for producing a hexafluoropropylene oxide dimer according to claim 1 or 2, wherein a molar ratio of a tertiary amine to a tertiary diamine in the composite catalyst system is 1 to 10: 1; the concentration of the tertiary amine is 0.5-5 mol/L;
the molar ratio of the tertiary amine to the phase transfer agent is 1-10: 1.
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| CN111072461A (en) * | 2019-12-19 | 2020-04-28 | 浙江巨圣氟化学有限公司 | Synthesis method of PPVE |
| CN117225476B (en) * | 2023-11-15 | 2024-02-20 | 山东华夏神舟新材料有限公司 | Supported metal catalyst and preparation and regeneration methods and application thereof |
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| JPS62195345A (en) * | 1986-02-21 | 1987-08-28 | Shin Etsu Chem Co Ltd | Production of hexafluoropropylene oxide oligomer |
| US4729856A (en) * | 1985-05-28 | 1988-03-08 | Ausimont S.P.A. | Process for the preparation of 2-perfluoropropoxy-perfluoropropionyl fluoride |
| CN1044092A (en) * | 1989-01-14 | 1990-07-25 | 赫彻斯特股份公司 | Process for dimerization of hexafluoropropene oxide |
| JPH04139146A (en) * | 1990-09-28 | 1992-05-13 | Nippon Mektron Ltd | Production of perfluoro(2-propoxypropionic acid) fluoride |
| CN103788363A (en) * | 2013-12-25 | 2014-05-14 | 上海艾肯化工科技有限公司 | Method for preparing perfluoropolyether with high molecular weight |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4729856A (en) * | 1985-05-28 | 1988-03-08 | Ausimont S.P.A. | Process for the preparation of 2-perfluoropropoxy-perfluoropropionyl fluoride |
| JPS62195345A (en) * | 1986-02-21 | 1987-08-28 | Shin Etsu Chem Co Ltd | Production of hexafluoropropylene oxide oligomer |
| CN1044092A (en) * | 1989-01-14 | 1990-07-25 | 赫彻斯特股份公司 | Process for dimerization of hexafluoropropene oxide |
| JPH04139146A (en) * | 1990-09-28 | 1992-05-13 | Nippon Mektron Ltd | Production of perfluoro(2-propoxypropionic acid) fluoride |
| CN103788363A (en) * | 2013-12-25 | 2014-05-14 | 上海艾肯化工科技有限公司 | Method for preparing perfluoropolyether with high molecular weight |
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