CN1962584A - Method for preparing 1,1,1-trifluoroethane - Google Patents
Method for preparing 1,1,1-trifluoroethane Download PDFInfo
- Publication number
- CN1962584A CN1962584A CN 200610070378 CN200610070378A CN1962584A CN 1962584 A CN1962584 A CN 1962584A CN 200610070378 CN200610070378 CN 200610070378 CN 200610070378 A CN200610070378 A CN 200610070378A CN 1962584 A CN1962584 A CN 1962584A
- Authority
- CN
- China
- Prior art keywords
- halothane
- preparation
- continuously
- catalyzer
- hydrofluoric acid
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract description 13
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 title abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229960003132 halothane Drugs 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000007791 liquid phase Substances 0.000 claims description 8
- 229910052787 antimony Inorganic materials 0.000 claims description 7
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 7
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical group Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 hydrocarbon fluoride Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 30
- 239000000376 reactant Substances 0.000 description 18
- 230000009466 transformation Effects 0.000 description 15
- 238000003682 fluorination reaction Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 229910000831 Steel Inorganic materials 0.000 description 9
- 238000007599 discharging Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000010959 steel Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 239000012535 impurity Substances 0.000 description 8
- 230000002779 inactivation Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparing method of 1, 1, 1-trifluoroethane in the hydrocarbon fluoride technical domain, which comprises the following steps: aerating R142b and HF in the reactor continuously; reacting under 0.5-1.5Mpa at 0-50 Deg C; adding anhydrous fluohydric acid and catalyst.
Description
Technical field
The present invention relates to hydro carbons fluorizated technical field, be specifically related to fluoridize 1-chloro-1 at liquid-phase catalysis, 1-C2H4F2 C2H4F2 (R142b) preparation 1,1,1-Halothane (R143a) with anhydrous hydrofluoric acid.
Background technology
Fluorochlorohydrocarbon (CFC
s) be acknowledged as the arch-criminal who damages the ozone layer.Along with the formulation and the enforcement of " Vienna Convention on Protection of Ozone Layer " and Montreal Protocol on Substances that Deplete the Ozone Layer, developed country stopped fluorochlorohydrocarbon (CFC before 1 day January in 1996
s) production and consumption, developing country also will stop fluorochlorohydrocarbon (CFC fully on January 1st, 2010
s) production and consumption.Therefore, fluorochlorohydrocarbon (CFC
s) eliminate and the exploitation of novel surrogate has proposed new challenge and opportunity to relevant industrial circle.
1,1,1-Halothane (R143a) does not have destruction (its depletion of the ozone layer latent energy value ODP is 0) to ozonosphere, and be widely used in fields such as refrigeration agent, whipping agent, propelling agent, clean-out systems, especially the mixture with other materials compositions replaces F22 in refrigerator, air-conditioning and other application facet, has obtained good result.Therefore, that develops simple possible is used to prepare 1,1, and the method for 1-Halothane (R143a) is of great importance.
Be used to prepare 1,1, many methods of 1-Halothane (R143a) are open.For example, with the vinylidene fluoride is the liquid phase and the gaseous fluoridizing method of raw material, it is the gaseous fluoridizing method of raw material that Chinese patent 200510073612.4 discloses with the vinylidene fluoride, but the price height of vinylidiene fluoride, and the rapid inactivation of common catalyzer meeting in the gas phase fluorination process, a kind of like this method has certain limitation in industrial application.Also have in addition with R141b and be the gaseous fluoridizing method of raw material and be the gaseous fluoridizing method of raw material with R142b.Patent application 97117186.6 discloses a kind of by fluoridizing 1-chloro-1,1-C2H4F2 C2H4F2 (R142b) preparation 1,1, and the method for 1-Halothane (R143a), still, the easy inactivation of catalyzer, and always generate the muriate by product of 130 and 120 series.
Summary of the invention
At the deficiencies in the prior art, the purpose of this invention is to provide 1,1 of a kind of high reactivity, low by product, the preparation method of 1-Halothane (R143a).
By fluoridizing 1-chloro-1,1-C2H4F2 C2H4F2 (R142b) prepares 1,1, and the method for 1-Halothane (R143a) normally selects for use antimonic halogenide as catalyzer.But among traditional preparation method, the antimonic halogenide of catalyzer is very easy to inactivation, and its reason is that antimonic halogenide is reduced into the antimony trihalid easily under reaction conditions, thereby loses catalytic activity.In order to prevent in reaction process, to feed reducing gas, as Cl owing to being reduced into the inactivation that the antimony trihalid causes
2Gas.
Though the verified SbCl that is difficult in
5Or make R142b and chlorine reaction under other Lewis acids existence, but always reaction generates muriate, especially 130 series (CFCl
2CH
2Cl, CF
2ClCH
2Cl, CCl
2=CHCl and analogue) and 120 series (CCl
3CHCl
2, CCl
2FCHCl
2, CF
2ClCHCl
2And analogue) the muriate by product, as patent application 97117186.6 reported.
In order to prevent antimonic halogenide inactivation, and reduce the generation of muriate by product, we have attempted a lot of methods.It is shocking that we find, add anhydrous hydrofluoric acid and catalyzer before feeding intake earlier, can effectively prevent antimonic halogenide inactivation, and improve the generation of transformation efficiency, minimizing side reaction greatly.
Added anhydrous hydrofluoric acid before feeding intake earlier, anhydrous hydrofluoric acid and antimonic halogenide form associated complex SbX
5(HF) x makes to be difficult for antimonic halogenide stabilization being reduced.Therefore the stability of catalyzer is improved greatly, catalyzer moves 500 hours continuously, and transformation efficiency does not fall as follows.
Technical scheme of the present invention is as follows:
Fluoridize 1-chloro-1 with anhydrous hydrofluoric acid at liquid-phase catalysis, 1-C2H4F2 C2H4F2 (R142b) preparation 1,1,1-Halothane (R143a) adds anhydrous hydrofluoric acid and catalyzer earlier before it is characterized in that feeding intake.
The add-on of above-mentioned anhydrous hydrofluoric acid and the weight ratio of catalyzer are 5-20: 1.
And then in reactor, feed continuously R142b and HF.Reaction equation is as follows:
CH
3CF
2Cl+HF→CH
3CF
3+HCl
What the above-mentioned active catalyst that is used for liquid phase fluorination reaction was the most suitable is antimonic halogenide, preferred antimony pentachloride or antimonic chloro-fluoride.
In the reaction process, the weight ratio that feeds intake of anhydrous hydrofluoric acid and R142b is 1: 4.5-5.2.
In reaction, catalyst concentration is also very crucial.The weight content of antimony is the 1-10% of liquid phase reaction thing, preferred 2-5%.
In the present invention, pressure can guarantee that being reflected at liquid phase gets final product, and reaction pressure is at absolute pressure 0.5-1.5MPa, preferably carry out at 0.7-1.2MPa.
In the present invention, the scope of temperature of reaction is very wide, can be 0-50 ℃ temperature, preferably carry out at 5-30 ℃.
The invention has the advantages that: transformation efficiency height, transformation efficiency are up to more than 99%, and unique impurity is unreacted R142b in the product, does not have other by products; Catalyzer long service life, catalyzer move 500 hours continuously, and transformation efficiency does not fall as follows, are easy to suitability for industrialized production.
Embodiment
Embodiment 1:
With 20kg HF and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, feeds R142b 3000g/h, HF 640g/h then at normal temperatures more continuously.
When treating that pressure is raised to 0.7MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 5 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.1% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Embodiment 2:
With 20kg HF and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, feeds R142b 3000g/h, HF 640g/h then at normal temperatures continuously.
When treating that pressure is raised to 0.8MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 15 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.5% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Embodiment 3:
With 20kg HF and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, feeds R142b 3000g/h, HF 640g/h then at normal temperatures continuously.
When treating that pressure is raised to 0.9MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 25 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.2% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Embodiment 4:
With 20kg HF and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, and this mixture is fed R142b 3000g/h, HF 640g/h continuously by reflux to 45 ℃ under this temperature then.
When treating that pressure is raised to 0.8MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 45 ℃, the reactant gases of discharging removes HCl and HF through washing, forms with the gas chromatograph analyzing organic substance, and the purity of R143a is 85%, move after 24 hours, the purity of R143a drops to 70%, moves 100 hours continuously, and the purity of R143a drops to below 10%.
Embodiment 5:
With 10kg HF and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, and this mixture is fed R142b 3000g/h, HF 640g/h continuously by reflux to 25 ℃ under this temperature then.
When treating that pressure is raised to 0.9MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 25 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.0% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Embodiment 6:
With 40kg HF and 2kg SbCl
5The common steel that joins 60 liters is equipped with in the conventional fluorination reactor of condenser, and this mixture is fed R142b 3000g/h, HF 640g/h continuously by reflux to 20 ℃ under this temperature then.
When treating that pressure is raised to 1.2MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 20 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.0% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Embodiment 7:
The common steel that the chloro-fluoride of 20kg HF and 2kg antimony is joined 30 liters is equipped with in the conventional fluorination reactor of condenser, and this mixture is fed R142b 3300g/h, HF 640g/h continuously by reflux to 35 ℃ under this temperature then.
When treating that pressure is raised to 0.6MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 35 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.0% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Embodiment 8:
With 20kg HF and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, and this mixture is fed R142b 2880g/h, HF 640g/h continuously by reflux to 30 ℃ under this temperature then.
When treating that pressure is raised to 1.5MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 30 ℃, the reactant gases of discharging removes HCl and HF through washing, form with the gas chromatograph analyzing organic substance, the purity 99.3% of R143a, unique impurity is R142b.This test moves 500 hours continuously, and the purity of R143a is not fallen as follows.
Comparative Examples
With 20kg R142b and 2kg SbCl
5The common steel that joins 30 liters is equipped with in the conventional fluorination reactor of condenser, and this mixture is fed R142b 3000g/h, HF 640g/h continuously by reflux to 45 ℃ under this temperature then.
When treating that pressure is raised to 0.8MPa, discharge reactant gases continuously and keep reaction pressure by condenser, temperature is controlled at 45 ℃, the reactant gases of discharging removes HCl and HF through washing, forms with the gas chromatograph analyzing organic substance, and the purity of R143a is 65%, move after 18 hours, the purity of R143a drops to 55%, moves 24 hours continuously, and the purity of R143a drops to below 10%.
The effect comparison table
| Project | Feeding sequence | Temperature ℃ | Pressure MPa | Transformation efficiency % | Working time and effect |
| Embodiment 1 | Throw HF earlier | 5 | 0.7 | 99.1 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Embodiment 2 | Throw HF earlier | 15 | 0.8 | 99.5 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Embodiment 3 | Throw HF earlier | 25 | 0.9 | 99.2 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Embodiment 4 | Throw HF earlier | 45 | 0.8 | 85 | Operation is 24 hours continuously, and transformation efficiency begins to descend, and reduces to below 10% after 100 hours |
| Embodiment 5 | Throw HF earlier | 25 | 0.9 | 99.0 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Embodiment 6 | Throw HF earlier | 20 | 1.2 | 99.0 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Embodiment 7 | Throw HF earlier | 35 | 0.6 | 99.0 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Embodiment 8 | Throw HF earlier | 30 | 1.5 | 99.3 | Operation is 500 hours continuously, and transformation efficiency does not fall as follows |
| Comparative Examples | Throw R142b earlier | 45 | 0.8 | 65 | Operation is 18 hours continuously, and transformation efficiency begins to descend, and reduces to below 10% after 24 hours |
Claims (10)
1, a kind of 1,1, the preparation method of 1-Halothane fluoridizes 1-chloro-1 with anhydrous hydrofluoric acid at liquid-phase catalysis, 1-C2H4F2 C2H4F2 (R142b) preparation 1,1, and 1-Halothane (R143a) adds anhydrous hydrofluoric acid and catalyzer earlier before it is characterized in that feeding intake.
2, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that the anhydrous hydrofluoric acid that adds earlier and the weight ratio of catalyzer are 5-20: 1.
3, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that used catalyzer is the halogenide of tin or antimony.
4, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that used catalyzer is antimony pentachloride or antimonic chloro-fluoride.
5, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that, the weight content of antimony is total 1-10% that adds material.
6, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that, the weight content of antimony is always to add material 2-5% in the liquid phase reaction thing.
7, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that, operates under the absolute pressure 0.5-1.5Mpa to carry out.
8, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that, in the reaction process, anhydrous hydrofluoric acid with fluoridize 1-chloro-1, the feed ratio of 1-C2H4F2 C2H4F2 (R142b) is 1: 4.5-5.2.
9, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that, temperature of reaction is 0-50 ℃.
10, as claimed in claim 1 described 1,1, the preparation method of 1-Halothane is characterized in that, temperature of reaction is 5-30 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100703784A CN100540516C (en) | 2006-11-29 | 2006-11-29 | A kind of 1,1, the preparation method of 1-Halothane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100703784A CN100540516C (en) | 2006-11-29 | 2006-11-29 | A kind of 1,1, the preparation method of 1-Halothane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1962584A true CN1962584A (en) | 2007-05-16 |
| CN100540516C CN100540516C (en) | 2009-09-16 |
Family
ID=38081834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100703784A Active CN100540516C (en) | 2006-11-29 | 2006-11-29 | A kind of 1,1, the preparation method of 1-Halothane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100540516C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109809960A (en) * | 2019-02-25 | 2019-05-28 | 内蒙古永和氟化工有限公司 | The preparation method of 1,1,1- trifluoroethane |
| CN112299948A (en) * | 2020-12-01 | 2021-02-02 | 山东华安新材料有限公司 | Preparation method of 1, 1, 1-trifluoro-2-chloroethane |
-
2006
- 2006-11-29 CN CNB2006100703784A patent/CN100540516C/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109809960A (en) * | 2019-02-25 | 2019-05-28 | 内蒙古永和氟化工有限公司 | The preparation method of 1,1,1- trifluoroethane |
| CN112299948A (en) * | 2020-12-01 | 2021-02-02 | 山东华安新材料有限公司 | Preparation method of 1, 1, 1-trifluoro-2-chloroethane |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100540516C (en) | 2009-09-16 |
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Effective date of registration: 20240111 Address after: 1399 Gongye Road, Tangshan Town, Huantai County, Zibo City, Shandong Province, 256400 Patentee after: Shandong Dongyue Green Cold Technology Co.,Ltd. Address before: 256401 Tangshan Town, Huantai County, Shandong Province Patentee before: SHANDONG DONGYUE CHEMICAL Co.,Ltd. |