CN105061162A - Preparation method of 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether - Google Patents

Preparation method of 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether Download PDF

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Publication number
CN105061162A
CN105061162A CN201510458942.9A CN201510458942A CN105061162A CN 105061162 A CN105061162 A CN 105061162A CN 201510458942 A CN201510458942 A CN 201510458942A CN 105061162 A CN105061162 A CN 105061162A
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parts
reaction
composite catalyst
preparation
trifluoroethyl
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王金明
马利勇
徐峰
林晓云
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Juhua Group Technology Centre
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/05Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215Sulfur-containing compounds
    • B01J31/0222Sulfur-containing compounds comprising sulfonyl groups
    • B01J31/0224Sulfur-containing compounds comprising sulfonyl groups being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
    • B01J31/0237Amines
    • B01J31/0238Amines with a primary amino group
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
    • B01J31/0244Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08Ion-exchange resins
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00Catalysts, in general, characterised by their form or physical properties
    • B01J35/19Catalysts containing parts with different compositions
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32Addition reactions to C=C or C-C triple bonds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention discloses a preparation method of 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether. The method comprises the steps of: (a) by weight, reacting 100 parts of strongly basic anion exchange resin, 200-400 parts of water, 0.1-0.5 part of N-hydroxyethyl perfluorooctane sulfonamide, 5-20 parts of 1, 8-diazabicyclo (5, 4, 0)undec-7-ene, and 0.05-0.5 part of ethylenediamine tetraacetic acid disodium at 40DEG C-80DEG C for 10-20h to obtain a composite catalyst for standby use; and (b) by weight, adding 100 parts of trifluoroethanol and 30-100 parts of the composite catalyst prepared in step (1) into a reaction kettle, then introducing a tetrafluoroethylene monomer to carry out reaction at 40-80DEG C, after introduction of 300-500 parts of the tetrafluoroethylene monomer, ending the reaction, performing filtering and recovering the composite catalyst, and subjecting the filtrate to washing and refining, thus obtaining 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether. The 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether prepared by the method provided by the invention has the advantages of good activity, recyclability, few three wastes, green and environmental protection.

Description

A kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers
Technical field
The present invention relates to the preparation method of fluorine-containing ether compounds, particularly a kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers.
Background technology
It is CF that Daikin and Asahi Glass are all proposed molecular formula 3cH 20CF 2cHF 2hydrogen fluorine ether, the commercialization name of great Jin is called HFE-S7, and the commercialization name of Asahi Glass is called AE3000, is called AE3100 (having another name called HFE347pc-f) by commercialization name after alcohol dilution.The numerous characteristics of HFE-347pc-f and CFC-113 are relatively, without the need to large adjustment in using method, but because its KB value is less than CFC-113, solvency power is slightly poor, so have difference again during use, the KB value of HFE-347pc-f is less, solvency power is more weak, so need during cleaning to use ultrasonic assistant.Simultaneously, suitable KB value makes it can have good consistency with most of material, be easy to reclaim and use, the feature of the low latent heat of vaporization makes it to have in same kind solvent evaporation rate faster, be good dry solvent, but also have larger volatilization loss simultaneously, so, cleaning machine with cooling and reflux device will greatly reduce volatilization loss, cost-saving.In addition, because HFE-347pc-f and most of solvent have good mutual solubility, can use with the solvent of solvency power strong (KB value is larger), learning from other's strong points to offset one's weaknesses, is a kind of excellent clean-out system.
China Patent Publication No. CN1651378A provides a kind of new hydrofluoro ether and preparation method thereof, in dimethyl formamide DMF or dimethyl sulfoxide (DMSO) DMSO organic solvent, potassium hydroxide or sodium hydroxide is used to be catalyzer, prepare new hydrofluoro ether, raw material is trifluoro-ethylene, tetrafluoroethylene, vinylidene, R 1216, trifluorochloroethylene and trifluoroethanol, trifluoropropanol, methyl alcohol, ethanol, propyl alcohol, butanols, at 20 ~ 90 DEG C of reaction 1 ~ 10h, obtained hydrogen fluorine ether.
China Patent Publication No. CN102115428A provides a kind of synthetic method of hydrogen fluorine ether, according to ratio of weight and number with 20 ~ 100 parts of alcohol for raw material, described alcohols is a kind of in methyl alcohol, ethanol, propyl alcohol, trifluoro methyl alcohol, C3-Fluoroalcohol and octafluoropentanol, under 1 ~ 6 part of alkali catalyst exists, add 34 ~ 108 parts of Fluorine containing olefines continuously, react at 110 ~ 180 DEG C, reaction pressure is 0.6 ~ 1.2MPa, reaction times is 1 ~ 5h, after rectifying separation, obtain target product.
Above patent and catalyzer that technical literature uses are mainly alkali metal compound, and there is catalyst recovery difficulty, dregginess is high, and because solid particulate is thin, the shortcomings such as product and catalyst separating difficulty, simultaneously because use a large amount of solvent, easily cause environmental pollution.
Summary of the invention
Technical problem to be solved by this invention overcomes the deficiencies in the prior art, and provide a kind of good catalyst activity, product is easily separated, the preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers of environmental protection.
In order to solve above technical problem, present invention employs following technical scheme: a kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, comprises the following steps:
A () by weight, by strongly basic anion exchange resin 100 parts, 200 ~ 400 parts, water, N-hydroxyethyl perfluorinated octyl sulfuryl amine 0.1 ~ 0.5 part, 1,8-diazabicyclo (5,4,0) 11 5 ~ 20 parts, carbon-7-alkene, disodium ethylene diamine tetraacetate 0.05 ~ 0.5 part, at 40 DEG C ~ 80 DEG C reaction 10 ~ 20h, obtained composite catalyst, for subsequent use;
B () by weight, 100 parts of trifluoroethanols, composite catalyst that 30 ~ 100 parts of steps (1) are obtained are added reactor, then passes into tetrafluoroethylene monomer and react at 40 ~ 80 DEG C, after passing into 300 ~ 500 parts of tetrafluoroethylene monomers, terminate reaction, filtered and recycled composite catalyst, filtrate obtains 1,1,2 through washing to refine, 2,-four fluoro ethyl-2,2,2-trifluoroethyl ethers.
The described temperature of reaction of step (a) is preferably 50 DEG C ~ 70 DEG C, and the reaction times is preferably 12 ~ 18h.
The described temperature of reaction of step (b) is preferably 50 DEG C ~ 70 DEG C.
Of the present invention 1,1,2,2 ,-four fluoro ethyls-2,2, the preparation method of 2-trifluoroethyl ether carries out in two steps, first prepares solid composite catalyst, then uses tetrafluoroethylene and trifluoroethanol as raw material, under the catalysis of solid composite catalyst, carry out etherification reaction obtain 1,1,2,2,-four fluoro ethyl-2,2,2-trifluoroethyl ether products.When preparing solid composite catalyst, N-hydroxyethyl perfluorinated octyl sulfuryl amine, 1,8-diazabicyclo (5,4,0) 11 carbon-7-alkene (DBU), disodium ethylene diamine tetraacetate (EDTA) is as alkaline enhanced aid, can be adsorbed on resin surface, the comprehensive alkalescence of composite catalyst is strengthened, and catalyst activity is better.Use solid composite catalyst catalysis tetrafluoroethylene and trifluoroethanol to carry out etherification reaction and obtain 1,1,2,2,-four fluoro ethyl-2,2,2-trifluoroethyl ether products, solid composite catalyst and product are easy to be separated, and the composite catalyst reclaimed can recycle, and effectively decreases the discharge of waste residue.The present invention not with an organic solvent, to avoid in prior art volatile organic solvent to the pollution of environment.
Raw material described in the present invention all can commercially availablely obtain, as strongly basic anion exchange resin can use strength triumphant resin in Shanghai to sell the D201 of company limited's production, the products such as 201*7.The product that N-hydroxyethyl perfluorinated octyl sulfuryl amine can adopt Sichuan Hua Gao Chemical Co., Ltd. to produce.The product that 1,8-diazabicyclo (5,4,0) 11 carbon-7-alkene (DBU) can adopt the biochemical (Shanghai) Co., Ltd. of gill to produce.
Compared with prior art, the present invention has following beneficial effect:
1, good catalyst activity, when preparing solid composite catalyst, N-hydroxyethyl perfluorinated octyl sulfuryl amine, 1,8-diazabicyclo (5,4,0) 11 carbon-7-alkene (DBU), disodium ethylene diamine tetraacetate (EDTA) is as alkaline enhanced aid, can be adsorbed on resin surface, the comprehensive alkalescence of composite catalyst is strengthened, and catalyst activity is better, yield is more than 92%, and selectivity is more than 97%;
2, product is easily separated, the present invention uses solid composite catalyst catalysis tetrafluoroethylene and trifluoroethanol to carry out etherification reaction and obtains 1,1,2,2 ,-four fluoro ethyls-2,2,2-trifluoroethyl ether product, adopts conventional filter operation just can effective Separation and Recovery solid composite catalyst, enormously simplify product purifying technique;
3, environmental protection, the composite catalyst of recovery can recycle, and effectively decreases the discharge of waste residue, and the present invention not with an organic solvent, to avoid in prior art volatile organic solvent to the pollution of environment.
Embodiment
Below in conjunction with specific embodiment, illustrate the present invention further, but these embodiments are only for explaining the present invention, instead of for limiting the scope of the invention.
Raw material in embodiment all can commercially availablely obtain, and wherein part material is described as follows:
Strongly basic anion exchange resin adopts strength triumphant resin in Shanghai to sell the D201 strongly basic anion exchange resin of company limited's production.
The product that N-hydroxyethyl perfluorinated octyl sulfuryl amine adopts Sichuan Hua Gao Chemical Co., Ltd. to produce.
The product that 1,8-diazabicyclo (5,4,0) 11 carbon-7-alkene (DBU) adopts the biochemical (Shanghai) Co., Ltd. of gill to produce.
Embodiment 1
A kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, comprises the following steps:
Step 1: add D201 strongly basic anion exchange resin 100Kg in 500L reactor, 300Kg water, the N-hydroxyethyl perfluorinated octyl sulfuryl amine of 0.3Kg, 1, the 8-diazabicyclo (5 of 10Kg, 4,0) 11 carbon-7-alkene (DBU), the disodium ethylene diamine tetraacetate (EDTA) of 0.2Kg, in 60 DEG C of stirring reaction 15h, obtained composite catalyst, for subsequent use.
Step 2: disposablely in 1000L stainless steel autoclave add 100Kg trifluoroethanol, the composite catalyst that the above-mentioned steps (1) of 70Kg is obtained, close charging opening, with the air in nitrogen replacement still, then pass into tetrafluoroethylene monomer, heat up and start reaction, temperature of reaction controls at 60 DEG C, metering passes into the tetrafluoroethylene of reactor, when terminating reaction after the tetrafluoroethylene monomer passing into 400Kg, filtered and recycled composite catalyst, filtrate obtains 1 through washing, rectifying, 1,2,2 ,-four fluoro ethyls-2,2,2-trifluoroethyl ether.Yield and selectivity are in table 1.
Embodiment 2
A kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, comprises the following steps:
Step 1: add D201 strongly basic anion exchange resin 100Kg in 500L reactor, the N-hydroxyethyl perfluorinated octyl sulfuryl amine of 200Kg water, 0.1Kg, 1 of 5Kg, 8-diazabicyclo (5,4,0) 11 carbon-7-alkene (DBU), the disodium ethylene diamine tetraacetate (EDTA) of 0.05Kg, in 40 DEG C of stirring reaction 20h, obtained composite catalyst, for subsequent use.
Step 2: disposablely in 1000L stainless steel autoclave add 100Kg trifluoroethanol, the composite catalyst that the above-mentioned steps (1) of 30Kg is obtained, close charging opening, with the air in nitrogen replacement still, then pass into tetrafluoroethylene monomer, heat up and start reaction, temperature of reaction controls at 40 DEG C, metering passes into the tetrafluoroethylene of reactor, when terminating reaction after the tetrafluoroethylene monomer passing into 300Kg, filtered and recycled composite catalyst, filtrate obtains 1 through washing, rectifying, 1,2,2 ,-four fluoro ethyls-2,2,2-trifluoroethyl ether.Yield and selectivity are in table 1.
Embodiment 3
A kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, comprises the following steps:
Step 1: add D201 strongly basic anion exchange resin 100Kg in 500L reactor respectively, 400Kg water, the N-hydroxyethyl perfluorinated octyl sulfuryl amine of 0.5Kg, 1, the 8-diazabicyclo (5 of 20Kg, 4,0) 11 carbon-7-alkene (DBU), the disodium ethylene diamine tetraacetate (EDTA) of 0.5Kg, in 80 DEG C of stirring reaction 10h, obtained composite catalyst, for subsequent use.
Step 2: disposablely in 1000L stainless steel autoclave add 100Kg trifluoroethanol, the composite catalyst that the above-mentioned steps (1) of 100Kg is obtained, close charging opening, with the air in nitrogen replacement still, then pass into tetrafluoroethylene monomer, heat up and start reaction, temperature of reaction controls at 80 DEG C, metering passes into the tetrafluoroethylene of reactor, when terminating reaction after the tetrafluoroethylene monomer passing into 500Kg, filtered and recycled composite catalyst, filtrate obtains 1 through washing, rectifying, 1,2,2 ,-four fluoro ethyls-2,2,2-trifluoroethyl ether.Yield and selectivity are in table 1.
Embodiment 4
A kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, comprises the following steps:
Step 1: add D201 strongly basic anion exchange resin 100Kg in 500L reactor, 350Kg water, the N-hydroxyethyl perfluorinated octyl sulfuryl amine of 0.4Kg, 1, the 8-diazabicyclo (5 of 15Kg, 4,0) 11 carbon-7-alkene (DBU), the disodium ethylene diamine tetraacetate (EDTA) of 0.4Kg, in 50 DEG C of stirring reaction 12h, obtained composite catalyst, for subsequent use.
Step 2: disposablely in 1000L stainless steel autoclave add 100Kg trifluoroethanol, the composite catalyst that the above-mentioned steps (1) of 80Kg is obtained, close charging opening, with the air in nitrogen replacement still, then pass into tetrafluoroethylene monomer, heat up and start reaction, temperature of reaction controls at 50 DEG C, metering passes into the tetrafluoroethylene of reactor, when terminating reaction after the tetrafluoroethylene monomer passing into 450Kg, filtered and recycled composite catalyst, filtrate obtains 1 through washing, rectifying, 1,2,2 ,-four fluoro ethyls-2,2,2-trifluoroethyl ether.Yield and selectivity are in table 1.
Embodiment 5
A kind of preparation method of 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, comprises the following steps:
Step 1: add D201 strongly basic anion exchange resin 100Kg in 500L reactor, 250Kg water, the N-hydroxyethyl perfluorinated octyl sulfuryl amine of 0.2Kg, 1, the 8-diazabicyclo (5 of 7.5Kg, 4,0) 11 carbon-7-alkene (DBU), the disodium ethylene diamine tetraacetate (EDTA) of 0.1Kg, in 70 DEG C of stirring reaction 17h, obtained composite catalyst, for subsequent use.
Step 2: disposablely in 1000L stainless steel autoclave add 100Kg trifluoroethanol, the composite catalyst that the above-mentioned steps (1) of 50Kg is obtained, close charging opening, with the air in nitrogen replacement still, then pass into tetrafluoroethylene monomer, heat up and start reaction, temperature of reaction controls at 70 DEG C, metering passes into the tetrafluoroethylene of reactor, when terminating reaction after the tetrafluoroethylene monomer passing into 350Kg, filtered and recycled composite catalyst, filtrate obtains 1 through washing, rectifying, 1,2,2 ,-four fluoro ethyls-2,2,2-trifluoroethyl ether.Yield and selectivity are in table 1.
Comparative example 1
Step 1 does not add N-hydroxyethyl perfluorinated octyl sulfuryl amine, the other the same as in Example 1.Obtain 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ether products, yield and selectivity are in table 1.
Comparative example 2
Step 1 does not add 1,8-diazabicyclo (5,4,0) 11 carbon-7-alkene (DBU), the other the same as in Example 1.Obtain 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ether products, yield and selectivity are in table 1.
Comparative example 3
The potassium hydroxide adding 15% of trifluoroethanol quality in step 2 replaces composite catalyst, the other the same as in Example 1.Obtain 1,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ether products, yield and selectivity are in table 1.
Table 1: the yield of embodiment 1 ~ 3 and comparative example 1 ~ 3 and selectivity
Embodiment Yield % Selectivity .%
1 95 99
2 93 97
3 92 98
4 92 97
5 97 99
Comparative example 1 86 95
Comparative example 2 89 92
Comparative example 3 81 87

Claims (3)

1. one kind 1,2,2, the preparation method of-four fluoro ethyl-2,2,2-trifluoroethyl ethers, is characterized in that comprising the following steps:
A () by weight, by strongly basic anion exchange resin 100 parts, 200 ~ 400 parts, water, N-hydroxyethyl perfluorinated octyl sulfuryl amine 0.1 ~ 0.5 part, 1,8-diazabicyclo (5,4,0) 11 5 ~ 20 parts, carbon-7-alkene, disodium ethylene diamine tetraacetate 0.05 ~ 0.5 part, at 40 DEG C ~ 80 DEG C reaction 10 ~ 20h, obtained composite catalyst, for subsequent use;
B () by weight, 100 parts of trifluoroethanols, composite catalyst that 30 ~ 100 parts of steps (1) are obtained are added reactor, then passes into tetrafluoroethylene monomer and react at 40 ~ 80 DEG C, after passing into 300 ~ 500 parts of tetrafluoroethylene monomers, terminate reaction, filtered and recycled composite catalyst, filtrate obtains 1,1,2 through washing to refine, 2,-four fluoro ethyl-2,2,2-trifluoroethyl ethers.
2. the preparation method of according to claim 11,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, it is characterized in that the described temperature of reaction of step (a) is 50 DEG C ~ 70 DEG C, the reaction times is 12 ~ 18h.
3. the preparation method of according to claim 11,1,2,2 ,-four fluoro ethyl-2,2,2-trifluoroethyl ethers, is characterized in that the described temperature of reaction of step (b) is 50 DEG C ~ 70 DEG C.
CN201510458942.9A 2015-07-30 2015-07-30 Preparation method of 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether Pending CN105061162A (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1550481A (en) * 2003-05-20 2004-12-01 大金工业株式会社 Method for preparing fluoether compound
CN1651378A (en) * 2004-12-27 2005-08-10 大连振邦氟涂料股份有限公司 New hydrofluoro ether and its preparation method
CN103611570A (en) * 2013-12-10 2014-03-05 王金明 Preparation method of resin catalyst for synthesis of difluoromethyl ether
CN103772156A (en) * 2014-01-06 2014-05-07 巨化集团技术中心 Method of continuous catalytic synthesis of 1-alkoxyl-1,1,2,2-tetrafluoroethane in fixed bed
CN103980097A (en) * 2014-05-21 2014-08-13 芜湖职业技术学院 Method for synthesizing phenols by etherifying
CN104045524A (en) * 2014-07-10 2014-09-17 山东中氟化工科技有限公司 Clean production method for hydrofluoroester
CN104971774A (en) * 2015-07-08 2015-10-14 王金明 Preparation method for hydrofluoroether and catalyst thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1550481A (en) * 2003-05-20 2004-12-01 大金工业株式会社 Method for preparing fluoether compound
CN1651378A (en) * 2004-12-27 2005-08-10 大连振邦氟涂料股份有限公司 New hydrofluoro ether and its preparation method
CN103611570A (en) * 2013-12-10 2014-03-05 王金明 Preparation method of resin catalyst for synthesis of difluoromethyl ether
CN103772156A (en) * 2014-01-06 2014-05-07 巨化集团技术中心 Method of continuous catalytic synthesis of 1-alkoxyl-1,1,2,2-tetrafluoroethane in fixed bed
CN103980097A (en) * 2014-05-21 2014-08-13 芜湖职业技术学院 Method for synthesizing phenols by etherifying
CN104045524A (en) * 2014-07-10 2014-09-17 山东中氟化工科技有限公司 Clean production method for hydrofluoroester
CN104971774A (en) * 2015-07-08 2015-10-14 王金明 Preparation method for hydrofluoroether and catalyst thereof

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