CN101948367A - Preparation method taking 1,1,1-trifluoroethane as raw material - Google Patents
Preparation method taking 1,1,1-trifluoroethane as raw material Download PDFInfo
- Publication number
- CN101948367A CN101948367A CN2010102759920A CN201010275992A CN101948367A CN 101948367 A CN101948367 A CN 101948367A CN 2010102759920 A CN2010102759920 A CN 2010102759920A CN 201010275992 A CN201010275992 A CN 201010275992A CN 101948367 A CN101948367 A CN 101948367A
- Authority
- CN
- China
- Prior art keywords
- fluoro
- raw material
- halothane
- trifluoroethane
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002994 raw material Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 title abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 27
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 229960003132 halothane Drugs 0.000 claims description 24
- RGZHHTKDHXSAQQ-UHFFFAOYSA-N 1,1-dichloro-2-fluoroethane Chemical compound FCC(Cl)Cl RGZHHTKDHXSAQQ-UHFFFAOYSA-N 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- ZXUJWPHOPHHZLR-UHFFFAOYSA-N 1,1,1-trichloro-2-fluoroethane Chemical compound FCC(Cl)(Cl)Cl ZXUJWPHOPHHZLR-UHFFFAOYSA-N 0.000 claims description 11
- VEZJSKSPVQQGIS-UHFFFAOYSA-N 1-chloro-2-fluoroethane Chemical compound FCCCl VEZJSKSPVQQGIS-UHFFFAOYSA-N 0.000 claims description 11
- 238000004140 cleaning Methods 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 abstract description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 2
- 230000009466 transformation Effects 0.000 abstract description 2
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 239000007789 gas Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 208000012839 conversion disease Diseases 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- KLZDCUBZWUSEGO-UHFFFAOYSA-N CC.F.F.F.F.F Chemical compound CC.F.F.F.F.F KLZDCUBZWUSEGO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical class CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method taking 1,1,1-trifluoroethane as a raw material. The method comprises the following steps of: performing photo-chlorination or thermal chlorination on the 1,1,1-trifluoroethane to obtain mixed gas which contains 1,1,1-trifluoro-2-chloroethane, 1,1,1-trifluoro-2,2-dichloroethane and 1,1,1-trifluoro-2,2,2-trifluoroethane besides the 1,1,1-trifluoroethane serving as the raw material, wherein the molar ratio of chlorine gas to the 1,1,1-trifluoroethane is 0.01 to 3.3, the reaction temperature is controlled to be between 100 and 520 DEG C and a reaction pressure is controlled to be between 0 and 0.8 Pa; and performing water washing, alkali washing, fractional distillation and condensation on the mixed gas so as to obtain the 1,1,1-trifluoro-2-chloroethane, the 1,1,1-trifluoro-2,2-dichloroethane and the 1,1,1-trifluoro-2,2,2-trifluoroethane. The method has the advantages of high reaction transformation ratio/selectivity and yield, simple and convenient method and easy industrialized production because R133a, R123 and R113a are synthesized by performing photo-chlorination or thermal chlorination on the 1,1,1-trifluoroethane serving as the raw material.
Description
Technical field
The invention belongs to the organic fluorine chemical technology field, especially a kind of is the preparation method of raw material with the 1.1.1-Halothane.
Background technology
1.1.1 a trifluoro one 2 monochlorethanes commercial abbreviation HCFC133a or R133a, it is the important intermediate of agricultural chemicals medicine and fluorine Lyons substitute.About the preparation method of HCFC133a, many document records have been deposited.Mainly be divided into two classes, the first kind is to be raw material with trieline and anhydrous hydrofluoric acid, and liquid phase fluorination reaction synthesizes HCFC133a; Second class is the synthetic HCFC133a of unstripped gas solid state reaction catalytic fluorination with trieline and anhydrous hydrofluoric acid.Chinese patent: CN1127460C, CN1058013A.United States Patent (USP): US3003003, on the books to this
1.1.1 commercial HCFC123 or the R123 of abbreviating as of a trifluoro one 2.2 one C2H4F2 C2H4F2s, R123 has very wide Application Areas, is mainly used in refrigeration, fire-fighting, foaming industry, also can be used as raw material and produces pentafluoride ethane (R125) etc.Main production methods is raw material with R133a, prepares R123 through light chlorination formula thermal chlorination.Chinese patent: CM1273426C.CN1270156A is on the books to this.
1.1.1 a trifluoro one 2.2.2 one trichloroethane is commonly referred to CFC-113a or R113a, is a kind of important organic intermediate, main production methods has: (1) CFC-113 catalytic isomerization prepares CFC-113a.(2) be that the chlorination of raw material liquid-phase catalysis light prepares R133a with HCFC-133a, patent EP404297 EP407990 EP346612 US4060469 is all on the books.
Having the following disadvantages 1. in above-mentioned these patented methods respectively, starting material are difficult for obtaining; 2. product is more single; 3. impurity is more in the preparation process.4. equipment corrosion is serious in the preparation process.
Summary of the invention
The present invention will solve the shortcoming of above-mentioned prior art, providing a kind of is the preparation method of raw material with the 1.1.1-Halothane, it mainly is the method for preparing 1.1.1-three fluoro-2-monochloroethane, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane with the 1.1.1-Halothane, the mixed gas that contains R133a, R123, R113a after the purification chlorination is to produce R133a, R123, R113a method for product respectively.
The present invention solves the technical scheme that its technical problem adopts: this is the preparation method of raw material with the 1.1.1-Halothane, step is as follows: the 1.1.1-Halothane obtains containing the mixed gas of 1.1.1-three fluoro-2-monochloroethane, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane through light chlorination or thermal chlorination except that raw material 1.1.1-Halothane, chlorine and 1.1.1-Halothane be rate 0.01-3.3 in molar ratio, 100-520 ℃ of temperature of reaction control, reaction pressure 0-0.8 MPa; Mixed gas is through the washing alkali cleaning, and condensate fractionation obtains 1.1.1-three fluoro-2-monochlorethanes, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane.
As preferably, described 1.1.1-three fluoro-2-monochloroethane, 1.1.1-three fluoro-2.2-ethylene dichloride return reaction respectively during the course, increase the product ratio of 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane.
As preferably, described temperature of reaction is 150-510 ℃, and described reaction pressure is the 0.01-0.8 MPa, and the molar ratio of described chlorine and 1.1.1-Halothane is 0.03～2.5.
The effect that the present invention is useful is: with 1.1.1-Halothane HFC-143a (R143a, molecular formula C2H3F3) is light chlorination, thermal chlorination synthetic R133a, R123, the R113a of raw material, reaction conversion ratio selectivity and productive rate all very high, method is easy, is easy to suitability for industrialized production.
Description of drawings
Fig. 1 is a process flow sheet of the present invention;
Reference numeral: first chlorination reactor, 1, the second chlorination reactor, 2, the first water wash columns, 3, the second water wash columns 4, soda-wash tower 5, air storing duct 6, compressor 7, the first rectifying tower 8, the second rectifying tower 9, product groove 10.
Embodiment
The invention will be further described below in conjunction with drawings and Examples:
Thisly prepare 1.1.1-three fluoro-2-monochloroethane with the 1.1.1-Halothane, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-the method for three fluoro-2.2.2-trichloroethane, step is as follows: the 1.1.1-Halothane obtains containing 1.1.1-three fluoro-2-monochloroethane through light chlorination or thermal chlorination except that raw material 1.1.1-Halothane, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-the mixed gas of three fluoro-2.2.2-trichloroethane, mixed gas is through the washing alkali cleaning, and condensate fractionation obtains 1.1.1-three fluoro-2-monochlorethanes, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane.Described temperature of reaction is 150-510 ℃, and described reaction pressure is the 0.01-0.8 MPa, and the molar ratio of described chlorine and 1.1.1-Halothane is 0.03～2.5.Described 1.1.1-three fluoro-2-monochloroethane, 1.1.1-three fluoro-2.2-ethylene dichloride can return reaction respectively during the course, increase the product ratio of 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane.The present invention can be used for refrigeration agent, pharmaceutical manufacturing industry.
CH3CF3+Cl2→CH2ClCF3+HCl
CH3CF3+2Cl2→CHCl2CF3+2HCl
CH3CF3+3Cl2→Cl3CF3+3HCl
Ingredient proportion according to different chlorine and 1.1.1-Halothane (R143a) obtains different product ratios.
The simple flow process of technology of the present invention as shown in Figure 1, first chlorination reactor, 1, the second chlorination reactor, 2, the first water wash columns, 3, the second water wash columns 4 among the figure, soda-wash tower 5, air storing duct 6, compressor 7, the first rectifying tower 8, the second rectifying tower 9, product groove 10.
Raw material HFC-143a and chlorine are respectively from storing steel cylinder, charging in accordance with regulations, enter the light chlorination, the thermal chlorination reactor reacts, reaction product is handled through washing, soda-wash tower, removes by product HCL, and gas bag is stored, obtain crude product through cool condenser cooling, advance rectifying tower rectifying then, the boiling point difference according to three products (R133a.R123.R113a) obtains R133a, R123, R113a product respectively.
Chlorination reactor of the present invention adopts carbon tube, also can adopt glass or metal tube etc.The principal element that influences reaction result of the present invention comprises charge ratio, temperature of reaction, reaction time, chlorine and HFC-143a raw materials components mole ratio should preferably be controlled at 0.03～2.5 according to the present invention, if be lower than 0.03: 1, chlorine supply deficiency, reaction conversion ratio is reduced, and by product increases, and the raw materials components mole ratio of chlorine is if be higher than 2.5: 1, then the utilization ratio of chlorine descends, and can bring added burden to aftertreatment.Suitable reactions temperature of the present invention will not heat or cool off in the reaction at 150-510 ℃, visual response mouth of pipe footpath size and heat transfer heat radiation situation and decide, and this reaction relates to that to react be thermopositive reaction.Adding light source light photograph or indirect heating, can be with response situation conditioning equipment temperature.
The residence time of reaction mass in reaction tower is the another important factor that influences reaction result, the reaction time deficiency, chlorination reaction is insufficient, reaction conversion ratio and productive rate all can descend, reaction time is long also will to influence production capacity, energy consumption improves, and suitable reaction time should be controlled at 40～60 seconds, and the control of reaction time can realize by adjusting the raw material input speed.
By the inventive method, produce R133a, R123, R113a by the HCFC-143a chlorination, method is easy, and raw material can adopt the thick product of content below 98%, and reaction conversion ratio, selectivity and productive rate can reach more than 95%.Product of the present invention adopts gc analysis, and chromatographic stationary adopts organic carrier 407 mutually, 2 meters of column lengths, and 120 ℃ of column temperatures, hydrogen is adopted in carrier gas.
Embodiment 1: with long 1800mm, the Glass tubing of diameter 50mm is made first chlorination reactor 1, second chlorination reactor 2, and the reactor periphery is equipped with 8 of the white light emission pipes of wavelength 3000-3500A, long 840mm and the infrared heating device of power 3000KW.After the reaction beginning, connect power supply earlier, in reactor, lead to raw material HCFC-143a and chlorine then respectively, feeding speed: HCFC-143a0.95mol/h, chlorine 1.56mol/h, raw material is through being mixed into reactor, and reaction is carried out stopping after 5.5 hours, reaction product is through first water wash column 3 and second water wash column 4, soda-wash tower 5, cool off to such an extent that thick product 950 restrains, sampling analysis, wherein HCFC-133a content is 25.7%, HCFC-123 content 29.6%, R113a content are 42.8%.
Embodiment 2: the reaction unit that use-case 1 is same, remove the crude product that raw material HCFC-143a changes content 93.64% into, intake velocity change into HCFC-143a0.92mol/h outside the chlorine 2.13mol/h, other is all undertaken by example 1 same operational condition, reacts to stop after 5.5 hours, collects product 890 grams, sampling analysis, wherein HCFC-133a content is 4.7%, and HCFC-123 content 37.5%, R113a content are 54.3%.
In addition to the implementation, the present invention can also have other embodiments.All employings are equal to the technical scheme of replacement or equivalent transformation formation, all drop on the protection domain of requirement of the present invention.
Claims (5)
1. one kind is the preparation method of raw material with the 1.1-Halothane, and it is characterized in that: step is as follows:
(1), the 1.1.1-Halothane obtains containing the mixed gas of 1.1.1-three fluoro-2-monochloroethane, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane through light chlorination or thermal chlorination except that raw material 1.1.1-Halothane, chlorine and 1.1.1-Halothane be rate 0.01-3.3 in molar ratio, 100-520 ℃ of temperature of reaction control, reaction pressure 0-0.8 MPa;
(2), mixed gas through the washing alkali cleaning, condensate fractionation obtains 1.1.1-three fluoro-2-monochlorethanes, 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane.
2. according to claim 1 is the preparation method of raw material with the 1.1.1-Halothane, it is characterized in that: described 1.1.1-three fluoro-2-monochloroethane, 1.1.1-three fluoro-2.2-ethylene dichloride return reaction respectively during the course, increase the product ratio of 1.1.1-three fluoro-2.2-ethylene dichloride, 1.1.1-three fluoro-2.2.2-trichloroethane.
3. according to claim 1 is the preparation method of raw material with the 1.1.1-Halothane, it is characterized in that: described temperature of reaction is 150-510 ℃.
4. according to claim 1 is the preparation method of raw material with the 1.1.1-Halothane, it is characterized in that: described reaction pressure is the 0.01-0.8 MPa.
5. according to claim 1 is the preparation method of raw material with the 1.1.1-Halothane, it is characterized in that: the molar ratio of described chlorine and 1.1.1-Halothane is 0.03～2.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102759920A CN101948367A (en) | 2010-09-06 | 2010-09-06 | Preparation method taking 1,1,1-trifluoroethane as raw material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102759920A CN101948367A (en) | 2010-09-06 | 2010-09-06 | Preparation method taking 1,1,1-trifluoroethane as raw material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101948367A true CN101948367A (en) | 2011-01-19 |
Family
ID=43452017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102759920A Pending CN101948367A (en) | 2010-09-06 | 2010-09-06 | Preparation method taking 1,1,1-trifluoroethane as raw material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101948367A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617273A (en) * | 2012-03-07 | 2012-08-01 | 安徽海华化工有限公司 | Method for producing trichlorotrifluoroethane by high-temperature gas phase chlorination method |
| CN102766017A (en) * | 2012-07-31 | 2012-11-07 | 山东华安新材料有限公司 | Preparation method of tetrachloro-1,2-difluoroethane |
| CN106946646A (en) * | 2013-01-31 | 2017-07-14 | 浙江蓝天环保高科技股份有限公司 | A kind of method that coproduction prepares R122 and R112a |
| CN113264810A (en) * | 2021-06-03 | 2021-08-17 | 常熟三爱富振氟新材料有限公司 | Preparation process of F112 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2644845A (en) * | 1947-06-20 | 1953-07-07 | Purdue Research Foundation | Halogenation of fluorocarbons |
| CN1070633A (en) * | 1991-08-26 | 1993-04-07 | 纳慕尔杜邦公司 | 1,1,1-three chloro-2,2, the catalytic production method of 2-Halothane |
| CN1556083A (en) * | 2004-01-09 | 2004-12-22 | 浙江埃克盛化工有限公司 | Preparation method and production equipment of difluoro-chloroethane |
-
2010
- 2010-09-06 CN CN2010102759920A patent/CN101948367A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2644845A (en) * | 1947-06-20 | 1953-07-07 | Purdue Research Foundation | Halogenation of fluorocarbons |
| CN1070633A (en) * | 1991-08-26 | 1993-04-07 | 纳慕尔杜邦公司 | 1,1,1-three chloro-2,2, the catalytic production method of 2-Halothane |
| CN1556083A (en) * | 2004-01-09 | 2004-12-22 | 浙江埃克盛化工有限公司 | Preparation method and production equipment of difluoro-chloroethane |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617273A (en) * | 2012-03-07 | 2012-08-01 | 安徽海华化工有限公司 | Method for producing trichlorotrifluoroethane by high-temperature gas phase chlorination method |
| CN102617273B (en) * | 2012-03-07 | 2014-09-17 | 安徽海华科技股份有限公司 | Method for producing trichlorotrifluoroethane by high-temperature gas phase chlorination method |
| CN102766017A (en) * | 2012-07-31 | 2012-11-07 | 山东华安新材料有限公司 | Preparation method of tetrachloro-1,2-difluoroethane |
| CN106946646A (en) * | 2013-01-31 | 2017-07-14 | 浙江蓝天环保高科技股份有限公司 | A kind of method that coproduction prepares R122 and R112a |
| CN106946646B (en) * | 2013-01-31 | 2020-09-22 | 浙江蓝天环保高科技股份有限公司 | Method for co-producing R122 and R112a |
| CN113264810A (en) * | 2021-06-03 | 2021-08-17 | 常熟三爱富振氟新材料有限公司 | Preparation process of F112 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101665404B (en) | Method for producing 2,3,3,3-tetrafluoropropene | |
| CN101351427B (en) | Method for producing fluorinated organic compounds | |
| CN104203882B (en) | Production method of 2,3,3,3-tetrafluoropropene and 1,1-difluoroethylene | |
| JP6650523B2 (en) | Method for simultaneous production of 1-chloro-3,3,3-trifluoropropylene, 2,3,3,3-tetrafluoropropylene and 1,3,3,3-tetrafluoropropylene | |
| EP2826766B1 (en) | Production method for 2,3,3,3-tetra-fluoropropene | |
| CN115160988A (en) | Compositions containing trifluoroethylene | |
| CN104829417A (en) | Process for the preparation of fluorinated compounds | |
| CN103189338A (en) | Integrated process to coproduce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane | |
| US11572328B2 (en) | Process for manufacture of 2,3,3,3-tetrafluoropropene | |
| CN104016840A (en) | Method for preparing o-trifluoromethyl benzaldehyde | |
| WO2019047447A1 (en) | Method for co-producing various halogenated olefins and fluoroalkanes | |
| CN105399598A (en) | 1,1,1,3,3-perfluoropropane preparation device and preparation method | |
| JP5975096B2 (en) | Process for producing 2,3,3,3-tetrafluoropropene and 1,1-difluoroethylene | |
| CN113993828A (en) | Production method of reaction gas containing (E)-1,2-vinylidene fluoride | |
| CN101948367A (en) | Preparation method taking 1,1,1-trifluoroethane as raw material | |
| CN102603460B (en) | Preparation method of 2-chloro-1,1,1,2-tetrafluoropropane | |
| CN101747176B (en) | Method for preparation of trifluoro acetyl chloride with trifluoroethane chlorinated mixture | |
| CN103373894B (en) | Continuous method for preparing C3 saturated halogenated hydrocarbon alkyl | |
| CN107759440A (en) | A kind of method that fluorine by Fluorine containing olefine double bond is replaced as hydrogen | |
| CN104710273B (en) | A kind of preparation method of trifluoro-ethylene | |
| CN105330513A (en) | High-selectivity method for catalytically synthesizing cyclic hydrofluoroolefin | |
| CN115043701A (en) | Preparation method of cis-1-chloro-3, 3, 3-trifluoropropene | |
| CN101016223B (en) | Preparing method of pentafluorodichloropropane | |
| CN106565409A (en) | Method for preparing fluorinated compound CH2F-R (R is H or CF3) through difluoromethane pyrolysis | |
| CN105523915A (en) | Method for high-yield gas-phase catalytic cracking preparation of difluoroacetyl fluoride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20110119 |