CN104045524B - Clean production method for hydrofluoroester - Google Patents
Clean production method for hydrofluoroester Download PDFInfo
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- CN104045524B CN104045524B CN201410326217.1A CN201410326217A CN104045524B CN 104045524 B CN104045524 B CN 104045524B CN 201410326217 A CN201410326217 A CN 201410326217A CN 104045524 B CN104045524 B CN 104045524B
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- fluorine
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- tetrafluoroethylene
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- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 42
- 239000011737 fluorine Substances 0.000 claims abstract description 42
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 sodium alkoxide Chemical class 0.000 claims abstract description 9
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 7
- 239000011734 sodium Substances 0.000 claims abstract description 7
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- YEBAHVHZZBYXTG-UHFFFAOYSA-N sodium;hypofluorite Chemical class [Na+].F[O-] YEBAHVHZZBYXTG-UHFFFAOYSA-N 0.000 claims description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- 238000007664 blowing Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 230000002459 sustained effect Effects 0.000 claims description 10
- 238000010792 warming Methods 0.000 claims description 10
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 27
- 239000000463 material Substances 0.000 abstract description 17
- 150000001336 alkenes Chemical class 0.000 abstract description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JZJNHPJBZWEHPD-UHFFFAOYSA-N [F].[Na] Chemical compound [F].[Na] JZJNHPJBZWEHPD-UHFFFAOYSA-N 0.000 description 5
- UQMQEGXOVRHYOV-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanol Chemical compound [Na].OCC(F)(F)F UQMQEGXOVRHYOV-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of hydrofluoroester production and particularly relates to a clean production method for hydrofluoroester. The method is as follows: adding fluorine-containing sodium alkoxide catalyst into fluorine-containing alcohol liquor, adding fluorinated olefin, heating and stirring for reacting to obtain mixed liquor; carrying out after-treatment onto the mixed liquor to obtain hydrofluoroester, wherein the fluorine-containing sodium alkoxide catalyst is sodium trifluoroalkoxide, and the corresponding fluorine-containing alcohol is trifluoroalcohol or pentafluoroalcohol. The catalyst used by the method is fluorine-containing alkanol liquor of the fluorine-containing sodium alkoxide, and the fluorine-containing sodium alkoxide is one of reaction materials, so that any other solvent is not needed to be added, and therefore, separation of the solvent and reaction products is avoided, after-treatment steps are reduced, production cost is saved, reaction yield is high, product purity is high, and economic benefits are very high.
Description
Technical field
The present invention relates to hydrogen fluorine ether production technical field, particularly a kind of method of cleaner production hydrogen fluorine ether.
Background technology
Chlorofluorocarbons (CFCs) (CFCs) has excellent chemical stability, is widely used as refrigeration agent, whipping agent, propellant and industrial cleaning agent etc.But CFCs is one of essential substance destroying ozone, ozone-depleting is dived and is worth (ODP) height, and atmospheric residence time is very long, and the latent value (GWP) of Greenhouse effect is high.Therefore, develop CFCs substitute and become one of field that academia and industry member enliven very much.
In recent years, hydrogen fluorine ether more and more receives the concern of people as the surrogate of Chlorofluorocarbons (CFCs), and it is short that it has the air residence time, and the advantage such as do not damage the ozone layer and Greenhouse effect are low.
At present, the method preparing hydrogen fluorine ether has a lot, the preparation technology wherein mostly all adopting solvent to participate in, at solvent and basic cpd as under alkali metal hydroxide existence, reacts prepare hydrogen fluorine ether containing fluoroalkanol and fluorinated olefin.As patent CN102803191A, CN103739450A, CN1651378A etc.But above method all needs first through being separated, and then obtain last product through the method for washing, distillation, postprocessing working procedures is more.It is catalyzer with potassium hydroxide that CN102115428A describes one direct, do not add the method for other solvent, but this kind of method makes reaction conversion ratio only have 77% because the solubleness of potassium hydroxide in C3-Fluoroalcohol is not high.
Summary of the invention
Complicated in order to solve the aftertreatment existed in the synthesis of above hydrogen fluorine ether compound, the problem that transformation efficiency, yield are low, and need a large amount of solvent to cause environmental pollution, the invention provides a kind of cleaner production, cost-saving, yield is high, method that hydrogen fluorine ether is simply prepared in aftertreatment.
The present invention is achieved by the following measures:
The preparation method of hydrogen fluorine ether of the present invention, is under the effect of catalyzer at sodium fluoroalcoholates, does not add other solvent, reacts obtained by containing fluoroalkanol and fluorinated olefin; Comprise the following steps:
A method for cleaner production hydrogen fluorine ether, comprises the following steps:
(1) joined in fluorine-containing alcohol solution by sodium fluoroalcoholates catalyzer, add fluorinated olefin, heated and stirred is reacted, and obtains mixing solutions;
(2) above-mentioned mixing solutions is obtained hydrogen fluorine ether through aftertreatment;
Described sodium fluoroalcoholates catalyzer is trifluoro sodium alkoxide or five fluorine sodium alkoxide, and corresponding fluorine-containing alcohol is Trifluridol or five fluorine alcohol.
Described method, preferred sodium fluoroalcoholates is 0.17-0.22:1 with the weight ratio containing fluoroalkanol.
Described method, preferred sodium fluoroalcoholates is 0.2:1 with the weight ratio containing fluoroalkanol.
Described method, preferred sodium fluoroalcoholates mixes in the form of a solution with containing fluoroalkanol, and in sodium fluoroalcoholates solution, solvent is that mass concentration is 25% containing fluoroalkanol.
Described method, in preferred steps (1), temperature of reaction is 90-110 DEG C.
Described method, in preferred steps (2), temperature of reaction is 90-110 DEG C, and reaction pressure is 0.7 ~ 1.0MPa, and the reaction times is 6 ~ 10 hours.
Described method, preferred steps (2) concrete operations are as follows:
After reaction vessel is evacuated to-0.1MPa, add 2Kg containing fluoroalkanol, 4Kg concentration is the sodium fluoroalcoholates solution of 25%, then adds monomer tetrafluoroethylene to 0.4MPa, stirring is warming up to 90-110 DEG C, beginning gradation adds monomer and presses 0.9MPa to groove, controls still temperature at 90-110 DEG C simultaneously, is down to 0.7MPa again adds monomer to groove pressure when still internal pressure, so continue 2 hours, then start to add monomer continuously, then sustained reaction 5-7 hour, cooling, blowing.
Described method, the reactor of preferably wherein step (2) reaction is the withstand voltage reactor of stainless steel.
Described is R containing fluoroalkanol general formula
fcH
2oH:R
ffor CF
3 -, CF
3cF
2 -, CF
3(CF
2)
2 -, CF
3(CF
2)
3 -one, preferred CF
3 -or CF
3cF
2 -one.
Beneficial effect of the present invention:
The catalyzer that present method uses is the fluorine-containing alkanol solution of sodium fluoroalcoholates, and be one of reaction raw materials containing fluoroalkanol, so do not need to add other any solvent, thus avoid being separated of solvent and reaction product, reduce post-processing step, saved production cost, and reaction yield is high, product purity is high, has very high economic benefit.
Embodiment
For a better understanding of the present invention, further illustrate below in conjunction with specific embodiment.
embodiment 1
(1) add in 5L four-hole bottle by 4610g trifluoroethanol, nitrogen protection, mechanical stirring (rotating speed 500r/min), adds in flask by the sodium Metal 99.5 handled well, and sodium Metal 99.5 divides 10 batches to add, and adds 23g at every turn.After sodium Metal 99.5 completely dissolve, then add next batch.Temperature of reaction 60-70 DEG C, reacts 23 hours sodium Metal 99.5s and runs out of, obtained trifluoroethanol sodium solution.25% is about by detecting strength of solution;
(2) 10L autoclave is vacuumized, replace once with monomer, after being evacuated to-0.1MPa again, add 2Kg trifluoroethanol, 4Kg trifluoroethanol sodium solution, then add monomer to 0.4MPa, stir and be warming up to about 105 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 105 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 5 hours, cooling, blowing, to weigh, add tetrafluoroethylene 4.5Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 55 ~ 56 DEG C in top and be hydrogen fluorine ether product, product purity is 99.8%, and product yield is 82%.
embodiment 2
10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg trifluoroethanol, 3Kg concentration is the trifluoroethanol sodium solution of 25%, then adds tetrafluoroethylene to 0.4MPa, stirs and is warming up to about 105 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 105 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 5 hours, cooling, blowing, to weigh, add tetrafluoroethylene 3.6Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 55 ~ 56 DEG C in top and be hydrogen fluorine ether product, product purity is 99.6%, and product yield is 78%.
embodiment 3
10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg trifluoroethanol, 5.2Kg concentration is the trifluoroethanol sodium solution of 25%, then adds tetrafluoroethylene to 0.4MPa, stirs and is warming up to about 105 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 105 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 5 hours, cooling, blowing, to weigh, add tetrafluoroethylene 5.15Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 55 ~ 56 DEG C in top and be hydrogen fluorine ether product, product purity is 99.4%, and product yield is 80.2%.
embodiment 4
10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg trifluoroethanol, 2.2Kg concentration is the trifluoroethanol sodium solution of 25%, then adds tetrafluoroethylene to 0.4MPa, stirs and is warming up to about 105 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 105 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 7 hours, cooling, blowing, to weigh, add tetrafluoroethylene 2.73Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 55 ~ 56 DEG C in top and be hydrogen fluorine ether product, product purity is 98.6%, and product yield is 69.9%.
embodiment 5
(1) add in 5L four-hole bottle by 5268g five fluorine propyl alcohol, nitrogen protection, mechanical stirring (rotating speed 500r/min), adds in flask by the sodium Metal 99.5 handled well, and sodium Metal 99.5 divides 10 batches to add, and adds 18.4g at every turn.After sodium Metal 99.5 completely dissolve, then add next batch.Temperature of reaction 70-80 DEG C, reacts 25 hours sodium Metal 99.5s and runs out of, obtained five fluorine sodium propylate solution, is about 25% by detecting strength of solution;
(2) 10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg five fluorine propyl alcohol, 4Kg five fluorine sodium propylate solution, then add tetrafluoroethylene to 0.4MPa, stir and be warming up to about 108 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 108 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 6 hours, cooling, blowing, to weigh, add tetrafluoroethylene 3.1Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 67 ~ 68 DEG C in top and be hydrogen fluorine ether product, product purity is 97.5%, and product yield is 80.8%.
embodiment 6
10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg five fluorine propyl alcohol, 5Kg concentration is the five fluorine sodium propylate solution of 25%, then adds tetrafluoroethylene to 0.4MPa, stirs and is warming up to about 108 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 108 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 5 hours, cooling, blowing, to weigh, add tetrafluoroethylene 3.38Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 67 ~ 68 DEG C in top and be hydrogen fluorine ether product, product purity is 96.9%, and product yield is 78.8%.
embodiment 7
10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg five fluorine propyl alcohol, 2.8Kg concentration is the five fluorine sodium propylate solution of 25%, then adds tetrafluoroethylene to 0.4MPa, stirs and is warming up to about 108 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 108 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 5 hours, cooling, blowing, to weigh, add tetrafluoroethylene 2.24Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 67 ~ 68 DEG C in top and be hydrogen fluorine ether product, product purity is 96.6%, and product yield is 77.6%.
embodiment 8
10L autoclave is vacuumized, replace once with tetrafluoroethylene, after being evacuated to-0.1MPa again, add 2Kg five fluorine propyl alcohol, 2.2Kg concentration is the five fluorine sodium propylate solution of 25%, then adds tetrafluoroethylene to 0.4MPa, stirs and is warming up to about 108 DEG C, start gradation and add tetrafluoroethylene to storage tank pressure 0.90MPa, control still temperature at about 108 DEG C simultaneously.Be down to 0.7MPa when still internal pressure and again add tetrafluoroethylene to groove pressure, so continue 2 hours, then start to add tetrafluoroethylene continuously, then sustained reaction 5 hours, cooling, blowing, to weigh, add tetrafluoroethylene 2.04Kg altogether.The material of releasing is added rectifying still and carries out rectifying, collect the warm material at 67 ~ 68 DEG C in top and be hydrogen fluorine ether product, product purity is 96.6%, and product yield is 70.8%.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not by the restriction of embodiment; other is any do not deviate from spirit of the present invention and principle under make change, modification, combination, substitute, simplify and all should be equivalent substitute mode, be included within protection scope of the present invention.
Claims (3)
1. produce a method for hydrogen fluorine ether, it is characterized in that comprising the following steps:
(1) after reaction vessel being evacuated to-0.1MPa, add 2Kg fluorine-containing alcohol, 4Kg mass concentration is the sodium fluoroalcoholates solution of 25%, add monomer tetrafluoroethylene again to 0.4MPa, stirring is warming up to 90-110 DEG C, and beginning gradation adds monomer and presses 0.9MPa to groove, controls still temperature at 90-110 DEG C simultaneously, be down to 0.7MPa when still internal pressure and again add monomer to groove pressure, so continue 2 hours, then start to add monomer continuously, then sustained reaction 5-7 hour, cooling, blowing, obtain mixing solutions;
(2) above-mentioned mixing solutions is obtained hydrogen fluorine ether through aftertreatment;
Described sodium fluoroalcoholates catalyzer is trifluoro sodium alkoxide or five fluorine sodium alkoxide, and corresponding fluorine-containing alcohol is trifluoroethanol or five fluorine propyl alcohol;
Sodium fluoroalcoholates mixes with fluorine-containing alcohol in the form of a solution, and in sodium fluoroalcoholates solution, solvent is fluorine-containing alcohol.
2. method according to claim 1, is characterized in that in step (1), temperature of reaction is 90-110 DEG C.
3. method according to claim 1 and 2, the reactor of wherein step (1) reaction is the withstand voltage reactor of stainless steel.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410326217.1A CN104045524B (en) | 2014-07-10 | 2014-07-10 | Clean production method for hydrofluoroester |
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| CN201410326217.1A CN104045524B (en) | 2014-07-10 | 2014-07-10 | Clean production method for hydrofluoroester |
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| CN105061162A (en) * | 2015-07-30 | 2015-11-18 | 巨化集团技术中心 | Preparation method of 1, 1, 2, 2,-tetrafluoroethyl-2, 2, 2-trifluoroethyl ether |
| CN112142572A (en) * | 2020-09-18 | 2020-12-29 | 浙江巨化技术中心有限公司 | Continuous production method for synthesizing hydrofluoroether |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1798722A (en) * | 2003-06-04 | 2006-07-05 | 旭硝子株式会社 | Method for producing fluoroalkyl ether |
| EP2305626A1 (en) * | 2008-06-20 | 2011-04-06 | Daikin Industries, Ltd. | Method for producing fluorine-containing ether |
| CN102115428A (en) * | 2010-12-27 | 2011-07-06 | 锦州惠发天合化学有限公司 | Method for synthesizing hydrofluoro ether |
-
2014
- 2014-07-10 CN CN201410326217.1A patent/CN104045524B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1798722A (en) * | 2003-06-04 | 2006-07-05 | 旭硝子株式会社 | Method for producing fluoroalkyl ether |
| EP2305626A1 (en) * | 2008-06-20 | 2011-04-06 | Daikin Industries, Ltd. | Method for producing fluorine-containing ether |
| CN102115428A (en) * | 2010-12-27 | 2011-07-06 | 锦州惠发天合化学有限公司 | Method for synthesizing hydrofluoro ether |
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