CN105801335A - Synthetic process of 1,2 difluoro-1,2 dichloroethylene - Google Patents
Synthetic process of 1,2 difluoro-1,2 dichloroethylene Download PDFInfo
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- CN105801335A CN105801335A CN201610263117.8A CN201610263117A CN105801335A CN 105801335 A CN105801335 A CN 105801335A CN 201610263117 A CN201610263117 A CN 201610263117A CN 105801335 A CN105801335 A CN 105801335A
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- dichloroethylene
- fluoro
- zinc powder
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- 238000000034 method Methods 0.000 title claims abstract description 24
- UPVJEODAZWTJKZ-UPHRSURJSA-N (z)-1,2-dichloro-1,2-difluoroethene Chemical group F\C(Cl)=C(/F)Cl UPVJEODAZWTJKZ-UPHRSURJSA-N 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 71
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000006298 dechlorination reaction Methods 0.000 claims abstract description 22
- 238000004821 distillation Methods 0.000 claims abstract description 19
- 239000012535 impurity Substances 0.000 claims abstract description 17
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical compound FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- LWDGFGTYBDRKHU-UHFFFAOYSA-N 1,2-dichloro-1-fluoroethene Chemical group FC(Cl)=CCl LWDGFGTYBDRKHU-UHFFFAOYSA-N 0.000 claims description 29
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- -1 difluoro sym-tetrachloroethane Chemical compound 0.000 claims description 12
- QPFMBZIOSGYJDE-UHFFFAOYSA-N acetylene tetrachloride Natural products ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 11
- SHTHWCQBJTUESB-UHFFFAOYSA-N ethyl hypofluorite Chemical compound CCOF SHTHWCQBJTUESB-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- MSHXSYMNYJAOSS-UHFFFAOYSA-N 1,1-dichloro-2-fluoroethene Chemical group FC=C(Cl)Cl MSHXSYMNYJAOSS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000066 reactive distillation Methods 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 238000001704 evaporation Methods 0.000 claims 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 abstract 1
- UPVJEODAZWTJKZ-UHFFFAOYSA-N 1,2-dichloro-1,2-difluoroethene Chemical compound FC(Cl)=C(F)Cl UPVJEODAZWTJKZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 238000005457 optimization Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a synthetic process of 1,2 difluoro-1,2 dichloroethylene. The synthetic process comprises the following steps: dechlorination reaction: causing tetra-chlorodifluoroethane (R112) which is used as a raw material and zinc powder to carry out a dechlorination reaction under a condition of the presence of ethyl alcohol to generate difluoro-dichloroethene; distillation operation: slowly adding sodium ethoxide into distillate at the temperature of 0-60DEG C to carry out reaction distillation operation, causing impurities 1.1 difluoro-2.2 dichloroethene and alcohol to react to generate ether in the presence of catalyst, then, carrying out distillation operation to remove impurity ether, and obtaining the finished product 1,2 difluoro-1,2 dichloroethylene. An intermittent process is adopted, the distillate is added into a reaction still by metering and is stirred, the catalyst is slowly added to carry out the reaction distillation operation, and fractionation is carried out to obtain the product, wherein the purity of the product is greater than or equal to 99.5%, and the yield of the product is greater than or equal to 95%.
Description
Technical field
The invention belongs to chemical field, be specifically related to a kind of 1,2 two fluoro-1,2 dichloroethylene synthesis techniques.
Background technology
1,2 two fluoro-1,2 dichloroethylene are the chemical intermediates with essential industry meaning, are to prepare perfluoroalkyl (oxygen)
Vinyl ethers, such as the necessary intermediate of perfluoro methyl vinyl ether (being called for short PMVE).PMVE is to produce perfluoroether and low temperature resistant fluorine
Rubber and the important intermediate of modified fluoroplastics, be also synthesis fluoro-containing pesticide and the important source material of fluorine-containing medicines intermediate, city
Field has a extensive future.
Usual 1,2 two fluoro-1,2 dichloroethylene are by 1,2-difluoro sym-tetrachloroethane (be called for short F112) under zinc powder is catalyzed, in
In polar solvent, dechlorination reaction prepares.But traditional F112 exists such as next during producing 1,2 2 fluoro-1,2 dichloroethylene
A little problems: 1) traditional handicraft is zinc powder and ethanol disposably puts in reactor, then about 50 DEG C drip F112 and react.But
Be activation zinc powder together with a large amount of ethanol in the presence of easily lump, make stirring the most difficult, simultaneously bed material also be difficult to process.2)
The zinc powder of activation is relatively more active, and water reaction can produce hydrogen and amount of heat, so can produce the biggest when mixing with ethanol
Unsafe factor, easily causes ethanol combustion accident.For problem above, invent one more safe and environment-friendly, efficient
Process route.
Summary of the invention
Goal of the invention: in order to solve the deficiencies in the prior art, the invention provides a kind of 1,2 two fluoro-1,2 dichloroethylene and closes
Become technique.
Technical scheme: a kind of 1,2 two fluoro-1,2 dichloroethylene synthesis techniques, comprises the steps:
The first step, dechlorination reaction: using difluoro sym-tetrachloroethane (R112) is that raw material and zinc powder are carried out under conditions of ethanol exists
Dechlorination reaction generates dichlorodifluoroethylene, and the zinc powder of described 10% is activated by diluted acid, and the mesh number of zinc powder is 50-500 mesh,
Reaction equation is as follows:
；
Second step: distillation operation: the first step is distillated product: 1.2 2 fluoro-1.2 dichloroethylene, ethanol and impurity 1.1 2 are fluoro-
2.2 dichloroethylene slowly drip Sodium ethylate at a temperature of 10 DEG C-60 DEG C and carry out reactive distillation operation, impurity 1.1 2 fluoro-2.2
Dichloroethylene generates ethoxy fluorine ether with ethanol synthesis in the presence of Sodium ethylate, then carries out distillation operation, by impurity ethoxy fluorine ether
Remove, receive out finished product 1,2 two fluoro-1,2 dichloroethylene；Its reaction equation is as follows:
。
As optimization: in the described first step, dechlorination reaction, use batch technology, difluoro sym-tetrachloroethane is added after metering
Enter in reactor, open stirring, add zinc powder, be warmed up to 20 DEG C-70 DEG C, be slowly added dropwise to ethanol and react, control well back
Flow ratio, qualified after go out fraction to fraction groove, be progressively warmed up to about 90-120 DEG C to substantially without fraction.
As optimization: in the described first step, dechlorination reaction, the course of reaction time is 6-24 hour.
As optimization: in the described first step, dechlorination reaction, add zinc powder in 1:1-2mol ratio.
As optimization: in the described first step, dechlorination reaction, the ratio adding ethanol slowly dripped is 1:2-6mol.
As optimization: in the described first step, dechlorination reaction, zinc powder particle diameter is 50-800 mesh, preferably 200-500 mesh.
As optimization: in the described first step, dechlorination reaction, zinc powder needs, through diluted acid activation processing, to activate ratio
1-50% for zinc powder gross mass.
As optimization: in described second step, distillation operation, catalyst is alkaline metal organic salt, alkali metal alcoholates, such as first
Sodium alkoxide, Sodium ethylate.
As optimization: in described second step, distillation operation, reactant alcohol is methanol or ethanol.
Beneficial effect: the present invention uses batch technology, will distillate product and add in reactor through measuring, open stirring, slowly
Dropping sodium alkoxide, carries out reactive distillation operation, and fractional distillation obtains product.Finished product purity >=99.5%, yield >=95%.The present invention uses second
The feeding mode of ethanol is dripped, dangerous when decreasing during zinc powder is directly added into ethanol in traditional handicraft after alcohol and F112 mixing
Factor, does not has potential safety hazard；And zinc powder is not easy caking, it is to avoid in course of reaction, zinc powder lumps the risk of stuck stirring, and
Reaction terminates rear bed material and fails to lay down difficulty.
Accompanying drawing explanation
Fig. 1 is the process flow diagram of the present invention.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described.
Specific embodiment 1
As it is shown in figure 1, a kind of 1,2 two fluoro-1,2 dichloroethylene synthesis techniques, comprise the steps:
The first step, dechlorination reaction: using difluoro sym-tetrachloroethane (R112) is that raw material and zinc powder are carried out under conditions of ethanol exists
Dechlorination reaction generates dichlorodifluoroethylene, and the zinc powder of described 10% is activated by diluted acid, and the mesh number of zinc powder is 50 mesh, reaction
Equation is as follows:
；
In the described first step, dechlorination reaction, use batch technology, 204g difluoro sym-tetrachloroethane is joined reactor after metering
In, to open stirring, add zinc powder in 1:1mol ratio, be warmed up to 20 DEG C, be slowly added dropwise to ethanol and react, the ratio of ethanol is
1:2mol, controls reflux ratio well, qualified after go out fraction to fraction groove, be progressively warmed up to about 90 DEG C to substantially without fraction.Instead
Answering process time is 6 hours.
Second step: distillation operation: the first step is distillated product: 1.2 2 fluoro-1.2 dichloroethylene, ethanol and impurity 1.1 2
Fluoro-2.2 dichloroethylene slowly drip Sodium ethylate at a temperature of 10 DEG C and carry out reactive distillation operation, impurity 1.1 2 fluoro-2.2 2
Vinyl chloride generates ethoxy fluorine ether with ethanol synthesis in the presence of Sodium ethylate, then carries out distillation operation, is removed by impurity ethoxy fluorine ether
Go, receive out finished product 1,2 two fluoro-1,2 dichloroethylene；Its reaction equation is as follows:
。
In described second step, distillation operation, catalyst is alkaline metal organic salt, the pure salt of alkali metal, Feldalat NM.
Specific embodiment 2
As it is shown in figure 1, a kind of 1,2 two fluoro-1,2 dichloroethylene synthesis techniques, comprise the steps:
The first step, dechlorination reaction: using difluoro sym-tetrachloroethane (R112) is that raw material and zinc powder are carried out under conditions of ethanol exists
Dechlorination reaction generates dichlorodifluoroethylene, and the zinc powder of described 10% is activated by diluted acid, and the mesh number of zinc powder is 100 mesh, reaction
Equation is as follows:
；
In the described first step, dechlorination reaction, use batch technology, difluoro sym-tetrachloroethane joined in reactor after metering,
Open stirring, add zinc powder in 1:2mol ratio, be warmed up to 20 DEG C-70 DEG C, be slowly added dropwise to ethanol and react, the ratio of ethanol
For 1:6mol, control reflux ratio well, qualified after go out fraction to fraction groove, be progressively warmed up to about 120 DEG C to substantially without fraction.
The course of reaction time is 24 hours.
Second step: distillation operation: the first step is distillated product: 1.2 2 fluoro-1.2 dichloroethylene, ethanol and impurity 1.1 2
Fluoro-2.2 dichloroethylene slowly drip Sodium ethylate at a temperature of 60 DEG C and carry out reactive distillation operation, impurity 1.1 2 fluoro-2.2 2
Vinyl chloride generates ethoxy fluorine ether with ethanol synthesis in the presence of Sodium ethylate, then carries out distillation operation, is removed by impurity ethoxy fluorine ether
Go, receive out finished product 1,2 two fluoro-1,2 dichloroethylene；Its reaction equation is as follows:
。
In described second step, distillation operation, catalyst is alkaline metal organic salt, the pure salt of alkali metal, Feldalat NM.
Specific embodiment 3
As it is shown in figure 1, a kind of 1,2 two fluoro-1,2 dichloroethylene synthesis techniques, comprise the steps:
The first step, dechlorination reaction: using difluoro sym-tetrachloroethane (R112) is that raw material and zinc powder are carried out under conditions of ethanol exists
Dechlorination reaction generates dichlorodifluoroethylene, and the zinc powder of described 10% is activated by diluted acid, and the mesh number of zinc powder is 80 mesh, reaction
Equation is as follows:
；
In the described first step, dechlorination reaction, use batch technology, difluoro sym-tetrachloroethane joined in reactor after metering,
Open stirring, add zinc powder in 1:1.5mol ratio, be warmed up to 20 DEG C-70 DEG C, be slowly added dropwise to ethanol and react, the ratio of ethanol
Example is 1:3mol, controls reflux ratio well, qualified after go out fraction to fraction groove, be progressively warmed up to about 110 DEG C to substantially without fraction being
Only.The course of reaction time is 18 hours.
Second step: distillation operation: the first step is distillated product: 1.2 2 fluoro-1.2 dichloroethylene, ethanol and impurity 1.1 2
Fluoro-2.2 dichloroethylene slowly drip Sodium ethylate at a temperature of 40 DEG C and carry out reactive distillation operation, impurity 1.1 2 fluoro-2.2 2
Vinyl chloride generates ethoxy fluorine ether with ethanol synthesis in the presence of Sodium ethylate, then carries out distillation operation, is removed by impurity ethoxy fluorine ether
Go, receive out finished product 1,2 two fluoro-1,2 dichloroethylene；Its reaction equation is as follows:
。
In described second step, distillation operation, catalyst is alkaline metal organic salt, the pure salt of alkali metal, Feldalat NM.
The present invention is not limited to above-mentioned preferred forms, and anyone can show that under the enlightenment of the present invention other are various
The product of form, no matter but in its shape or structure, make any change, every have same as the present application or akin skill
Art scheme, within all falling within protection scope of the present invention.
Claims (9)
1. one kind 1,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: comprise the steps:
The first step, dechlorination reaction: using difluoro sym-tetrachloroethane (R112) is that raw material and zinc powder are carried out under conditions of ethanol exists
Dechlorination reaction generates dichlorodifluoroethylene, and the zinc powder of described 10% is activated by diluted acid, and the mesh number of zinc powder is 50-800 mesh,
Reaction equation is as follows:
；
Second step: distillation operation: the first step is distillated product: 1.2 2 fluoro-1.2 dichloroethylene, ethanol and impurity 1.1 2 are fluoro-
2.2 dichloroethylene slowly drips Sodium ethylate at a temperature of 10 DEG C-60 DEG C carries out reactive distillation operation, impurity 1.1 2 fluoro-2.2
Dichloroethylene reacts generation ether in the presence of a catalyst with alcohol, then carries out distillation operation, is removed by impurity ethoxy fluorine ether, receives out
Fluoro-1,2 dichloroethylene of finished product 1,2 2；Its reaction equation is as follows:
。
The most according to claim 11,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: the described first step, de-
In chlorine reaction, use batch technology, difluoro sym-tetrachloroethane is joined in reactor after metering, open stirring, add zinc powder,
At 0 DEG C-70 DEG C, be slowly added dropwise to ethanol and react, control reflux ratio well, qualified after go out fraction to fraction groove, progressively heat up
To about 90-120 DEG C to substantially without fraction.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: the described first step, de-
In chlorine reaction, the course of reaction time is 6-24 hour.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: the described first step, de-
In chlorine reaction, add zinc powder in 1:1-2mol ratio.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: the described first step, de-
In chlorine reaction, the ratio adding ethanol slowly dripped is 1:2-6mol.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: the described first step, de-
In chlorine reaction, zinc powder particle diameter is 50-800 mesh, preferably 200-500 mesh.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: the described first step, de-
In chlorine reaction, zinc powder needs through diluted acid activation processing, and activation ratio is the 1-50% of zinc powder gross mass.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: described second step, essence
Evaporating in operation, catalyst is alkaline metal organic salt, alkali metal alcoholates, such as Feldalat NM, Sodium ethylate.
The most according to claim 21,2 two fluoro-1,2 dichloroethylene synthesis techniques, it is characterised in that: described second step, essence
Evaporating in operation, reactant alcohol is methanol or ethanol.
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|---|---|---|---|
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| CN201610263117.8A CN105801335B (en) | 2016-04-26 | 2016-04-26 | A kind of 1,2 2 fluoro- 1,2 dichloroethylene synthesis technologies |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299148A (en) * | 2016-10-18 | 2018-07-20 | 邵武华航新材料有限公司 | A kind of method that coproduction prepares bis- chloro- 1,1,2- trifluoroethane of pentafluoroethane and 1,2- |
| WO2022261728A1 (en) * | 2021-06-18 | 2022-12-22 | Commonwealth Scientific And Industrial Research Organisation | Purification process |
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| CN1986512A (en) * | 2005-12-22 | 2007-06-27 | 索尔维索莱克西斯公司 | Process for preparing fluorohalogenethers |
| CN101910096A (en) * | 2008-01-08 | 2010-12-08 | 索维索莱克西斯公开有限公司 | Process for the synthesis of perfluorobutadiene |
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| Title |
|---|
| H.T,ET AL.: "reactions of fluoro monomer.I.mechanism of reaction of 1,1-dicloro-.2,2-difluoroethene with methol under conditions of base catalysis", 《ZHURNAL OBSHCHEI KHIMII》 * |
| 陈彬彬等: "1，2 － 二氟四氯乙烷脱氯新工艺开发", 《有机氟工业》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299148A (en) * | 2016-10-18 | 2018-07-20 | 邵武华航新材料有限公司 | A kind of method that coproduction prepares bis- chloro- 1,1,2- trifluoroethane of pentafluoroethane and 1,2- |
| CN108299148B (en) * | 2016-10-18 | 2020-09-29 | 福州绿航环保技术服务有限公司 | Method for coproducing pentafluoroethane and 1, 2-dichloro-1, 1, 2-trifluoroethane |
| WO2022261728A1 (en) * | 2021-06-18 | 2022-12-22 | Commonwealth Scientific And Industrial Research Organisation | Purification process |
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| CN105801335B (en) | 2019-06-18 |
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