CN105801335B - A kind of 1,2 2 fluoro- 1,2 dichloroethylene synthesis technologies - Google Patents
A kind of 1,2 2 fluoro- 1,2 dichloroethylene synthesis technologies Download PDFInfo
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- CN105801335B CN105801335B CN201610263117.8A CN201610263117A CN105801335B CN 105801335 B CN105801335 B CN 105801335B CN 201610263117 A CN201610263117 A CN 201610263117A CN 105801335 B CN105801335 B CN 105801335B
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- LWDGFGTYBDRKHU-UHFFFAOYSA-N 1,2-dichloro-1-fluoroethene Chemical group FC(Cl)=CCl LWDGFGTYBDRKHU-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000005516 engineering process Methods 0.000 title claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 71
- 235000019441 ethanol Nutrition 0.000 claims abstract description 35
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006298 dechlorination reaction Methods 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000004821 distillation Methods 0.000 claims abstract description 17
- 239000012535 impurity Substances 0.000 claims abstract description 17
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical class FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 claims abstract description 11
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 9
- MSHXSYMNYJAOSS-UHFFFAOYSA-N 1,1-dichloro-2-fluoroethene Chemical group FC=C(Cl)Cl MSHXSYMNYJAOSS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000066 reactive distillation Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- SHTHWCQBJTUESB-UHFFFAOYSA-N ethyl hypofluorite Chemical compound CCOF SHTHWCQBJTUESB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 4
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 claims 3
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 claims 1
- UPVJEODAZWTJKZ-UHFFFAOYSA-N 1,2-dichloro-1,2-difluoroethene Chemical group FC(Cl)=C(F)Cl UPVJEODAZWTJKZ-UHFFFAOYSA-N 0.000 claims 1
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 abstract description 5
- 238000005194 fractionation Methods 0.000 abstract description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000005457 optimization Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- -1 Sodium alkoxide Chemical class 0.000 description 2
- 230000004913 activation Effects 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
- UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical class FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 239000000376 reactant 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
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- 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 one kind 1,2 two fluoro- 1, and 2 dichloroethylene synthesis technologies include the following steps: dechlorination reaction: progress dechlorination reaction generation dichlorodifluoroethylene under the conditions of use difluoro tetrachloroethanes (R112) be raw material and zinc powder existing for the ethyl alcohol；Distillation operation: by distillate product 0 DEG C -60 DEG C at a temperature of be slowly added dropwise sodium ethoxide carry out reactive distillation operation, fluoro- 2.2 dichloroethylene of impurity 1.1 2 react in the presence of a catalyst with alcohol generation ether, then carry out distillation operation, impurity ether is removed, receive out finished product 1,2 two fluoro- 1,2 dichloroethylene.The present invention uses batch technology, will distillate product and in metered reaction kettle, is opened stirring, and catalyst is slowly added dropwise, and carries out reactive distillation operation, and fractionation obtains product.Finished product purity >=99.5%, yield >=95%.
Description
Technical field
The invention belongs to chemical fields, and in particular to one kind 1,2 two fluoro- 1,2 dichloroethylene synthesis technologies.
Background technique
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 (abbreviation PMVE).PMVE is production perfluoroether and low temperature resistant fluorine
The important intermediate of rubber and modified fluoroplastics, and the important source material of synthesis fluoro-containing pesticide and fluorine-containing medicines intermediate, city
Field has a extensive future.
Usual 1,2 two fluoro- 1,2 dichloroethylene be by 1,2- difluoro tetrachloroethanes (abbreviation F112) zinc powder catalysis under, in
Dechlorination reaction is made in polar solvent.But traditional F112 exists during producing 1,2 2 fluoro- 1,2 dichloroethylene as next
A little problems: 1) traditional handicraft is that zinc powder and ethyl alcohol are disposably put into reaction kettle, then 50 DEG C or so dropwise addition F112 are reacted.But
Be activation zinc powder and a large amount of ethyl alcohol together in the presence of be easy agglomeration, keep stirring very difficult, while bottom material is also difficult to handle.2)
The zinc powder of activation is more active and water reaction can generate hydrogen and amount of heat, so can generate when with ethyl alcohol mixing very big
Unsafe factor easily causes ethanol combustion accident.In view of the above problems, having invented a kind of 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 present invention provides one kind 1,2 two fluoro- 1,2 dichloroethylene are closed
At technique.
Technical solution: one kind 1,2 two fluoro- 1,2 dichloroethylene synthesis technologies include the following steps:
The first step, dechlorination reaction: under the conditions of using difluoro tetrachloroethanes (R112) for raw material and zinc powder existing for the ethyl alcohol
It carries out dechlorination reaction and generates dichlorodifluoroethylene, described 10% zinc powder is activated by diluted acid, and the mesh number of zinc powder is 50-500
Mesh, reaction equation are as follows:
；
Step 2: distillation operation: the first step is distillated product: 1.2 2 fluoro- 1.2 dichloroethylene, ethyl alcohol and impurity 1.1 2
Fluoro- 2.2 dichloroethylene 10 DEG C -60 DEG C at a temperature of sodium ethoxide be slowly added dropwise carry out reactive distillation operation, impurity 1.1 2 is fluoro-
2.2 dichloroethylene generate ethoxy fluorine ether with ethanol synthesis in the presence of sodium ethoxide, distillation operation are then carried out, by impurity ethoxy fluorine
Ether removes, and receives out finished product 1, and 2 two fluoro- 1,2 dichloroethylene；Its reaction equation is as follows:
。
As optimization: in the first step, dechlorination reaction, using batch technology, difluoro tetrachloroethanes being added after metering
Enter into reaction kettle, open stirring, zinc powder is added, is warming up to 20 DEG C -70 DEG C, is slowly added dropwise to ethyl alcohol and is reacted, controlled back
Flow ratio, fraction gone out after qualified to fraction slot, be gradually warming up to about 90-120 DEG C to substantially without fraction until.
As optimization: in the first step, dechlorination reaction, the reaction process time is 6-24 hours.
As optimization: in the first step, dechlorination reaction, zinc powder is added in 1:1-2mol ratio.
As optimization: in the first step, dechlorination reaction, the ratio of the addition ethyl alcohol slowly dripped is 1:2-6mol.
As optimization: in the first step, dechlorination reaction, zinc powder partial size is 50-800 mesh, preferably 200-500 mesh.
As optimization: in the first step, dechlorination reaction, zinc powder needs to be activated by diluted acid, activates ratio
For the 1-50% of zinc powder gross mass.
As optimization: in the second step, distillation operation, catalyst is alkaline metal organic salt, alkali metal alcoholates, such as first
Sodium alkoxide, sodium ethoxide.
As optimization: in the second step, distillation operation, reactant alcohol is methanol or ethyl alcohol.
The utility model has the advantages that the present invention uses batch technology, product will be distillated through opening stirring, slowly in metered reaction kettle
Sodium alkoxide is added dropwise, carries out reactive distillation operation, fractionation obtains product.Finished product purity >=99.5%, yield >=95%.The present invention uses second
The feeding mode of ethyl alcohol is added dropwise after pure and mild F112 mixing, reduces dangerous when zinc powder is directly added into ethyl alcohol in traditional handicraft
Factor, without security risk；And zinc powder is not easy to agglomerate, and avoids zinc powder in reaction process and agglomerates the risk of stuck stirring, and
Bottom material fails to lay down difficulty after reaction.
Detailed description of the invention
Fig. 1 is process flow diagram of the invention.
Specific embodiment
The present invention is further explained in the light of specific embodiments.
Specific embodiment 1
As shown in Figure 1, one kind 1,2 two fluoro- 1,2 dichloroethylene synthesis technologies include the following steps:
The first step, dechlorination reaction: under the conditions of using difluoro tetrachloroethanes (R112) for raw material and zinc powder existing for the ethyl alcohol
It carrying out dechlorination reaction and generates dichlorodifluoroethylene, described 10% zinc powder is activated by diluted acid, and the mesh number of zinc powder is 50 mesh,
Reaction equation is as follows:
；
In the first step, dechlorination reaction, using batch technology, 204g difluoro tetrachloroethanes is added to instead after metering
It answers in kettle, opens stirring, zinc powder is added in 1:1mol ratio, is warming up to 20 DEG C, is slowly added dropwise to ethyl alcohol and is reacted, the ratio of ethyl alcohol
Example is 1:2mol, controls reflux ratio, and fraction is gone out after qualified to fraction slot, is gradually warming up to about 90 DEG C to being without fraction substantially
Only.The reaction process time is 6 hours.
Step 2: distillation operation: the first step is distillated product: 1.2 2 fluoro- 1.2 dichloroethylene, ethyl alcohol and impurity 1.1 2
Fluoro- 2.2 dichloroethylene 10 DEG C at a temperature of be slowly added dropwise sodium ethoxide 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 ethoxide, then carries out distillation operation, impurity ethoxy fluorine ether is removed
It goes, receives out finished product 1,2 two fluoro- 1,2 dichloroethylene；Its reaction equation is as follows:
。
In the second step, distillation operation, catalyst is alkaline metal organic salt, the pure salt of alkali metal, sodium methoxide.
Specific embodiment 2
As shown in Figure 1, one kind 1,2 two fluoro- 1,2 dichloroethylene synthesis technologies include the following steps:
The first step, dechlorination reaction: under the conditions of using difluoro tetrachloroethanes (R112) for raw material and zinc powder existing for the ethyl alcohol
It carrying out dechlorination reaction and generates dichlorodifluoroethylene, described 10% zinc powder is activated by diluted acid, and the mesh number of zinc powder is 100 mesh,
Reaction equation is as follows:
；
In the first step, dechlorination reaction, using batch technology, difluoro tetrachloroethanes is added to reaction kettle after metering
In, stirring is opened, zinc powder is added in 1:2mol ratio, is warming up to 20 DEG C -70 DEG C, is slowly added dropwise to ethyl alcohol and is reacted, ethyl alcohol
Ratio is 1:6mol, controls reflux ratio, and fraction is gone out after qualified to fraction slot, is gradually warming up to about 120 DEG C to substantially without fraction
Until.The reaction process time is 24 hours.
Step 2: distillation operation: the first step is distillated product: 1.2 2 fluoro- 1.2 dichloroethylene, ethyl alcohol and impurity 1.1 2
Fluoro- 2.2 dichloroethylene 60 DEG C at a temperature of be slowly added dropwise sodium ethoxide 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 ethoxide, then carries out distillation operation, impurity ethoxy fluorine ether is removed
It goes, receives out finished product 1,2 two fluoro- 1,2 dichloroethylene；Its reaction equation is as follows:
。
In the second step, distillation operation, catalyst is alkaline metal organic salt, the pure salt of alkali metal, sodium methoxide.
Specific embodiment 3
As shown in Figure 1, one kind 1,2 two fluoro- 1,2 dichloroethylene synthesis technologies include the following steps:
The first step, dechlorination reaction: under the conditions of using difluoro tetrachloroethanes (R112) for raw material and zinc powder existing for the ethyl alcohol
It carrying out dechlorination reaction and generates dichlorodifluoroethylene, described 10% zinc powder is activated by diluted acid, and the mesh number of zinc powder is 80 mesh,
Reaction equation is as follows:
；
In the first step, dechlorination reaction, using batch technology, difluoro tetrachloroethanes is added to reaction kettle after metering
In, stirring is opened, zinc powder is added in 1:1.5mol ratio, is warming up to 20 DEG C -70 DEG C, is slowly added dropwise to ethyl alcohol and is reacted, ethyl alcohol
Ratio be 1:3mol, control reflux ratio, fraction gone out after qualified to fraction slot, be gradually warming up to about 110 DEG C to substantially without evaporating
It is divided into only.The reaction process time is 18 hours.
Step 2: distillation operation: the first step is distillated product: 1.2 2 fluoro- 1.2 dichloroethylene, ethyl alcohol and impurity 1.1 2
Fluoro- 2.2 dichloroethylene 40 DEG C at a temperature of be slowly added dropwise sodium ethoxide 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 ethoxide, then carries out distillation operation, impurity ethoxy fluorine ether is removed
It goes, receives out finished product 1,2 two fluoro- 1,2 dichloroethylene；Its reaction equation is as follows:
。
In the second step, distillation operation, catalyst is alkaline metal organic salt, the pure salt of alkali metal, sodium methoxide.
The present invention is not limited to above-mentioned preferred forms, anyone can show that other are various under the inspiration of the present invention
The product of form, however, make any variation in its shape or structure, it is all that there is skill identical or similar to the present application
Art scheme, is within the scope of the present invention.
Claims (5)
1. one kind 1,2- bis- fluoro- 1,2 dichloroethylene synthesis technologies, characterized by the following steps:
The first step, dechlorination reaction: it is anti-that dechlorination is carried out under the conditions of using difluoro tetrachloroethanes for raw material and zinc powder existing for the ethyl alcohol
Dichlorodifluoroethylene should be generated, described 10% zinc powder is activated by diluted acid, and the mesh number of zinc powder is 50-800 mesh, reaction side
Formula is as follows:
Step 2: distillation operation: the first step is distillated product: fluoro- 1,2 dichloroethylene of 1,2- bis-, ethyl alcohol and impurity 1,1- bis- are fluoro-
2,2- dichloroethylene 10 DEG C -60 DEG C at a temperature of sodium ethoxide be slowly added dropwise carry out reactive distillation operation, impurity 1,1- bis- is fluoro-
2,2- dichloroethylene are reacted with alcohol in the presence of a catalyst generates ether, then carries out distillation operation, impurity ethoxy fluorine ether is removed,
Receive out fluoro- 1,2 dichloroethylene of finished product 1,2- bis-；Its reaction equation is as follows:
2. 1,2- bis- fluoro- 1 according to claim 1,2 dichloroethylene synthesis technologies, it is characterised in that: the first step,
In dechlorination reaction, using batch technology, difluoro tetrachloroethanes is added in reaction kettle after metering, opens stirring, zinc powder is added,
It at 0 DEG C -70 DEG C, is slowly added dropwise to ethyl alcohol and is reacted, control reflux ratio, fraction is gone out after qualified to fraction slot, is gradually risen
Temperature to 90-120 DEG C to substantially without fraction until.
3. 1,2- bis- fluoro- 1 according to claim 2,2 dichloroethylene synthesis technologies, it is characterised in that: the first step,
In dechlorination reaction, the reaction process time is 6-24 hours.
4. 1,2- bis- fluoro- 1 according to claim 2,2 dichloroethylene synthesis technologies, it is characterised in that: the first step,
In dechlorination reaction, zinc powder is added by the molar ratio of 1:1-2.
5. 1,2- bis- fluoro- 1 according to claim 2,2 dichloroethylene synthesis technologies, it is characterised in that: the first step,
In dechlorination reaction, the molar ratio of the addition ethyl alcohol slowly dripped is 1:2-6.
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Effective date of registration: 20200119 Address after: 310000 No. 85, Xihu District, Hangzhou, Zhejiang, Xueyuan Road Patentee after: Xu Maoqian Address before: 226000 Nantong Qidong Economic Development Zone Jiangsu fine chemical industry concentrated area Patentee before: Nantong Baokai Chemical Co.,Ltd. |
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Effective date of registration: 20231121 Address after: 012000 Fluoride Industrial Park, Fengzhen City, Ulanqab City, Inner Mongolia Autonomous Region Patentee after: Inner Mongolia Oasis New Fluorine Environmental Protection Technology Co.,Ltd. Address before: No.85 Xueyuan Road, Xihu District, Hangzhou, Zhejiang 310000 Patentee before: Xu Maoqian |