CN101723797A - Method for producing tetrafluoromethane by gas phase catalysis - Google Patents
Method for producing tetrafluoromethane by gas phase catalysis Download PDFInfo
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- CN101723797A CN101723797A CN200810121732A CN200810121732A CN101723797A CN 101723797 A CN101723797 A CN 101723797A CN 200810121732 A CN200810121732 A CN 200810121732A CN 200810121732 A CN200810121732 A CN 200810121732A CN 101723797 A CN101723797 A CN 101723797A
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Abstract
The invention discloses a method for producing a tetrafluoromethane by gas phase catalysis. Aiming at the defects of high needed reaction temperature and low conversion per pass existing in the conventional process for producing FC-14 by gas phase fluorination, the invention provides an economic and high-efficient method for producing the tetrafluoromethane by gas phase catalysis, which has the advantages of low needed reaction temperature and high conversion per pass. The method for producing the tetrafluoromethane comprises the following step: reacting halohydrocarbon with hydrogen fluoride at the presence of a gas phase fluorination catalyst in a gas phase to produce the tetrafluoromethane, wherein the molar ratio of the halohydrocarbon to the hydrogen fluoride is 1:1-10; the halohydrocarbon is one or more of the tetrafluoromethane, trichloromonofluomethane, dichlorodifluoromethane and monochlorotrifluoromethane; the used gas phase fluorination catalyst adopts a chromium compound as an active component and an aluminum compound as a carrier; and the molar ratio of the chromium to the aluminum is 1:1-19. The method for producing the tetrafluoromethane has the characteristics of long service life and high percent conversion of the halohydrocarbon.
Description
Technical field
The present invention relates to a kind of method of the method for producing tetrafluoromethane, particularly a kind of producing tetrafluoromethane by gas phase catalysis.
Background technology
Tetrafluoromethane (below can be described as FC-14) is a compound very useful in the industry, for example, it is the plasma etch gases of consumption maximum in the present microelectronics industry, its high-purity gas and the high-purity gas of tetrafluoromethane are joined the gas mixture of high purity oxygen gas, can be widely used in the etching of thin-film materials such as silicon, silicon-dioxide, silicon nitride, phosphorosilicate glass and tungsten; Also there are a large amount of uses aspects such as its production at electron device surface cleaning, solar cell, laser technology, gas phase insulation, super low temperature refrigeration agent, leak check agent, stain remover, Metal smelting and plastic industry.
In order to produce FC-14, the whole bag of tricks has been proposed up to now.The at present industrial method that is used to prepare FC-14 mainly contains following several:
(1) method of carbon and fluorine gas reaction;
(2) method of methane and fluorine gas reaction;
(3) method of hydrogen fluoromethane and fluorine gas reaction;
(4) method of thermolysis tetrafluoroethylene;
(5) electrochemical fluorination method;
(6) fluorochloromethane and hydrogen fluoride gaseous fluoridizing method.
In the method for above-mentioned (1), (2) and (3), exist following weak point: used reactive extremely strong, expensive fluorine gas as the fluorine source, its reaction is to carry out in violent condition, wayward, the danger of blast is arranged, and directly add the reactor that fluorine gas needs special construction, to the equipment requirements height, corrosive danger is arranged, thus the generation problem relevant with operation with industrial production.In addition, prevent blast and carbon distribution as Explosion suppressant although can adopt inert gas dilution fluorine gas or employing to fluoridize halogen, when being causes an important problem---the purifying difficulty is increased, produce a large amount of losses, so this process is uneconomic.Particularly when preparing FC-14 as the fluorine source,, use excessive fluorine gas usually, can cause like this containing remaining fluorine gas in the finished product, thereby bring difficulty to refining step equally in order to improve product yield with fluorine gas.In addition the method for (3) except that the fluorine gas of costliness as the fluorine source, its price as the hydrogen fluoromethane of raw material is also higher relatively, has all limited the scale of industrialized unit.
Exist following weak point in the method for above-mentioned (4): its pyrolysis temperature is up to 1100 ℃, and process energy consumption is big, and product purity and yield are low.
In the method for above-mentioned (5),, therefore can not supply raw materials with the finite quantity relevant with the finite length of electrode because electrochemical fluorination occurs in electrode surface.So electrochemical fluorination has the problem that yields poorly.Other has Russ P to adopt the anode gas that contains HF that electrolysis KF2HF generates as the fluorine source, make it 700～1200 ℃ down and charcoal react and prepare FC-14.Obviously, this method needs high temperature, and energy consumption is excessive.
At present, the synthetic more promising a kind of method of FC-14 of industrialization is exactly above-mentioned (6) fluorochloromethane and hydrogen fluoride gaseous fluoridizing method.This method technology is simple, is easy to continuous large-scale production, and raw materials cost is low, and does not need to use expensive F
2, operational safety, facility investment is low.Yet under most of situations, with the hydrogen fluoride fluorination of halogenated hydrocarbon carry out not smooth, reaction is many to be carried out having under the condition of catalyzer, and activity of such catalysts and stability are the keys of realization suitability for industrialized production.
The many activity of catalyzer that adopt in existing fluorochloromethane and the hydrogen fluoride gaseous fluoridizing method production FC-14 technology are relatively poor, stability is not high.In the case, in order to obtain satisfied productive rate, should synthetic FC-14 reaction needed under high temperature, low-speed, just can carry out, and adopt multistage successive reaction and excessive HF to improve the transformation efficiency of fluorochloromethane, so the economy of existing fluorochloromethane and hydrogen fluoride gaseous fluoridizing method production FC-14 technology is relatively poor more.
Summary of the invention
The objective of the invention is to produce existing desired reaction temperature height in the FC-14 technology, weak point that per pass conversion is low, the method for the producing tetrafluoromethane by gas phase catalysis of the economical and efficient that a kind of desired reaction temperature is low, per pass conversion is high is provided at existing gaseous fluoridizing method.
The present invention finishes by following technical scheme, a kind of method of producing tetrafluoromethane by gas phase catalysis, its method of producing tetrafluoromethane is: with halohydrocarbon in the presence of catalysts for gas phase fluorination with the hydrogen fluoride production tetrafluoromethane that in gas phase, reacts, wherein, the mol ratio between halohydrocarbon and the HF is 1: 1～10; Halohydrocarbon adopts one or more in tetrachloromethane, Trichloromonofluoromethane, Refrigerant 12, the monochlorotrifluoromethane.
In the method for above-mentioned described a kind of producing tetrafluoromethane by gas phase catalysis, the catalysts for gas phase fluorination that is adopted is that the compound of employing Cr is an active ingredient, and adopting the compound of Al is carrier, and the mol ratio between Cr and the Al is 1: 1～19.
Above-mentioned described catalysts for gas phase fluorination preparation method is: adopt Al (NO
3)
3, AlCl
3, Al
2O
3, AlO (OH), Al (OH)
3, AlF
3, Al
2(SO
4)
3, γ-Al
2O
3In one or more as the Al presoma; Adopt Cr (NO
3)
3, CrCl
3, Cr
2O
3, Cr (OH)
3, CrF
3, Cr (C
2H
3O
2)
3, Cr (OH) SO
4In one or more as the Cr presoma; Prepare throw out with the precipitator method, precipitation agent adopts a kind of in ammoniacal liquor, volatile salt, yellow soda ash, sodium hydroxide, the potassium hydroxide, throw out drying, roasting obtain this catalyst precursor, obtain the catalyzer of producing tetrafluoromethane by gas-phase fluorination again through hydrogen fluoride trealment.
The method of a kind of producing tetrafluoromethane by gas phase catalysis of the present invention, its method may further comprise the steps:
(1) in proportion the mixture of one or more halohydrocarbon in a certain amount of tetrachloromethane, Trichloromonofluoromethane, Refrigerant 12, the monochlorotrifluoromethane and HF is contacted in reactor under 300～420 ℃ with described catalyzer, be 2～30 seconds duration of contact;
(2) product to step (1) carries out the knockout tower separating treatment, obtains the A cut at the bottom of the tower, cat head obtains the B cut;
(3) will from the A cut that step (2) obtain, reclaim HF and through be added to step (1) reactor as charging in, recycle; To deliver to water wash column washing from the B cut that step (2) obtain and separate, obtain the C cut at the bottom of the tower, cat head obtains the D cut;
(4) will after distilling, reclaim HCl from the C cut that step (3) obtain; The D cut that will obtain from step (3) is through alkali cleaning, drying and be collected in the cold-trap.From cold-trap, isolate and deliver to rectifying tower behind the tetrafluoromethane and carry out separating treatment, the gained mixture is delivered in step (1) reactor as charging and is recycled at the bottom of the pure tetrafluoromethane of recovered overhead, the tower, and isolated other mixture is delivered to the use of step (1) reactor cycles as charging after vaporizing from cold-trap.
Method of the present invention need not specific installation, the catalyzer long service life, and the transformation efficiency height of halohydrocarbon, and, be easy to further separation and purification to the selectivity height of FC-14, can directly carry out fractionation and handle.In addition, the production unit of this method is similar to Refrigerant 12 (CFC-12) production unit, and the existing equipment that easily will show buttoned-up production CFC-12 is transformed into the production line of FC-14, can reduce the equipment input of novel process.
Method of the present invention is specially adapted to producing tetrafluoromethane by gas phase catalysis, shows high economic worth in by tetrachloromethane, Trichloromonofluoromethane, Refrigerant 12, monochlorotrifluoromethane producing tetrafluoromethane by gas-phase fluorination.
Description of drawings
Fig. 1 is a kind of process flow sheet of producing tetrafluoromethane by gas phase catalysis.
Embodiment
Further specify the method for a kind of producing tetrafluoromethane by gas phase catalysis of invention below by embodiment, but the present invention is not limited to following examples.
Embodiment 1
Be to take by weighing Cr at 1: 4 at first according to the mol ratio between Cr and the Al
2O
3And Al (OH)
3, mix with an amount of water, add certain amount of ammonia water to precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 70 ℃.With the oven dry after throw out after moulding at 300 ℃, N
2Roasting is 48 hours in the atmosphere, obtains the fluorination catalyst precursor.The fluorination catalyst precursor was handled 48 hours down at 250 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 300 ℃, and the mol ratio that feeds monochlorotrifluoromethane and HF is 1: 1 a mixed gas, and be 30 seconds the duration of contact of mixed gas and catalyzer; Exit gas is through the knockout tower separating treatment, reclaims HF and deliver in the reactor as charging to recycle from tower bottom distillate.The knockout tower overhead fraction is delivered to the water wash column washing separate, and from the water wash column tower bottom distillate, reclaim HCl.With the water wash column overhead fraction through alkali cleaning, drying and be collected in the cold-trap.From cold-trap, isolate and deliver to rectifying tower behind the tetrafluoromethane and carry out separating treatment, the gained mixture is delivered in the reactor as charging and is recycled at the bottom of the pure tetrafluoromethane of recovered overhead, the tower, and isolated other mixture is delivered to the reactor cycles use as charging after vaporizing from cold-trap.
Sampling analysis is formed through the product of alkali cleaning, dry after washing column overhead cut, its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 2
Be to take by weighing Cr (OH) at 1: 19 at first according to the mol ratio between Cr and the Al
3And Al (NO
3)
3, mix with an amount of water, add a certain amount of Na
2CO
3To precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 120 ℃.With the oven dry after throw out after moulding at 600 ℃, N
2Roasting is 24 hours in the atmosphere, obtains the fluorination catalyst precursor.The fluorination catalyst precursor was handled 30 hours down at 400 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 400 ℃, and the mol ratio that feeds Refrigerant 12 and HF is 1: 10 a mixed gas, and be 2 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 3
Be to take by weighing CrCl at 1: 3 at first according to the mol ratio between Cr and the Al
3And Al
2O
3, mix with an amount of water, add a certain amount of KOH to precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 90 ℃.Throw out after the oven dry through roasting 36 hours in 400 ℃, air atmosphere after the moulding, is obtained the fluorination catalyst precursor.The fluorination catalyst precursor was handled 35 hours down at 350 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 360 ℃, and the mol ratio that feeds Trichloromonofluoromethane and HF is 1: 6 a mixed gas, and be 10 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 4
Be to take by weighing CrF at 1: 1.5 at first according to the mol ratio between Cr and the Al
3And AlCl
3, mix with an amount of water, add a certain amount of (NH
4)
2CO
3To precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 140 ℃.With the oven dry after throw out after moulding at 750 ℃, N
2Roasting is 2 hours in the atmosphere, obtains the fluorination catalyst precursor.The fluorination catalyst precursor was handled 2 hours down at 700 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 380 ℃, and the mol ratio that feeds Refrigerant 12 and HF is 1: 10 a mixed gas, and be 20 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 5
Be to take by weighing Cr (C at 1: 1 at first according to the mol ratio between Cr and the Al
2H
3O
2)
3And Al
2(SO
4)
3, mix with an amount of water, add a certain amount of NaOH to precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 110 ℃.Throw out after the oven dry through roasting 12 hours in 600 ℃, air atmosphere after the moulding, is obtained the fluorination catalyst precursor.The fluorination catalyst precursor was handled 25 hours down at 450 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 400 ℃, and the mol ratio that feeds Trichloromonofluoromethane and HF is 1: 6 a mixed gas, and be 20 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 6
Be to take by weighing Cr (NO at 1: 9 at first according to the mol ratio between Cr and the Al
3)
3And AlF
3, mix with an amount of water, add certain amount of ammonia water to precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 130 ℃.Throw out after the oven dry through roasting 8 hours in 650 ℃, air atmosphere after the moulding, is obtained the fluorination catalyst precursor.The fluorination catalyst precursor was handled 12 hours down at 600 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 420 ℃, and the mol ratio that feeds tetrachloromethane and HF is 1: 8 a mixed gas, and be 16 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 7
Be to take by weighing Cr (OH) SO at 1: 15 at first according to the mol ratio between Cr and the Al
4And AlCl
3, mix with an amount of water, add a certain amount of Na
2CO
3To precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 100 ℃.With the oven dry after throw out after moulding at 500 ℃, N
2Roasting is 16 hours in the atmosphere, obtains the fluorination catalyst precursor.The fluorination catalyst precursor was handled 32 hours down at 380 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 380 ℃, and the mol ratio that feeds Trichloromonofluoromethane and HF is 1: 8 a mixed gas, and be 12 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 8
Be to take by weighing Cr (NO at 1: 2 at first according to the mol ratio between Cr and the Al
3)
3And γ-Al
2O
3, mix with an amount of water, add a certain amount of NaOH to precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 70 ℃.With the oven dry after throw out after moulding at 300 ℃, N
2Roasting is 48 hours in the atmosphere, obtains the fluorination catalyst precursor.The fluorination catalyst precursor was handled 48 hours down at 250 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 300 ℃, and the mol ratio that feeds monochlorotrifluoromethane and HF is 1: 1 a mixed gas, and be 18 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 9
Be to take by weighing Cr (NO at 1: 12 at first according to the mol ratio between Cr and the Al
3)
3And AlO (OH), mix with an amount of water, add a certain amount of (NH
4)
2CO
3To precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 90 ℃.Throw out after the oven dry through roasting 36 hours in 400 ℃, air atmosphere after the moulding, is obtained the fluorination catalyst precursor.The fluorination catalyst precursor was handled 16 hours down at 550 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 400 ℃, and the mol ratio that feeds Refrigerant 12 and HF is 1: 3 a mixed gas, and be 8 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Embodiment 10
Be to take by weighing CrCl at 1: 6 at first according to the mol ratio between Cr and the Al
3And Al (OH)
3, mix with an amount of water, add certain amount of ammonia water to precipitating fully, be neutral through separating, wash then to filtrate, again throw out is dried down at 140 ℃.Throw out after the oven dry through roasting 12 hours in 600 ℃, air atmosphere after the moulding, is obtained the fluorination catalyst precursor.The fluorination catalyst precursor was handled 2 hours down at 700 ℃ with HF, obtained fluorination catalyst.
With a certain amount of gained fluorination catalyst reactor of packing into, temperature of reaction is 420 ℃, and the mol ratio that feeds tetrachloromethane and HF is 1: 10 a mixed gas, and be 24 seconds the duration of contact of mixed gas and catalyzer; Exit gas adopts the treatment process identical with embodiment 1.Its raw material per pass conversion and the selectivity of FC-14 seen Table 1.
Table 1. embodiment 1-10 catalyzer is to CCl
4Activity and the selectivity of FC-14
Embodiment 11
According to the method for the foregoing description, after preparation catalyzer and the processing, one or more media and the HF that feed in tetrachloromethane, Trichloromonofluoromethane, Refrigerant 12, the monochlorotrifluoromethane carry out the industrialization producing tetrafluoromethane by gas-phase fluorination.The working condition of suitability for industrialized production all can be implemented by the reaction conditions control of the foregoing description 1-10.The industrialized unit flow process as shown in Figure 1.
Claims (4)
1. the method for a producing tetrafluoromethane by gas phase catalysis, it is characterized in that, the method of producing tetrafluoromethane by gas phase catalysis is: with halohydrocarbon in the presence of catalysts for gas phase fluorination and the hydrogen fluoride production tetrafluoromethane that in gas phase, reacts, wherein, the mol ratio between halohydrocarbon and the HF is 1: 1～10; Halohydrocarbon adopts one or more in tetrachloromethane, Trichloromonofluoromethane, Refrigerant 12, the monochlorotrifluoromethane.
2. the method for a kind of producing tetrafluoromethane by gas phase catalysis according to claim 1 is characterized in that, it is active ingredient that described catalysts for gas phase fluorination adopts the compound of Cr, and adopting the compound of Al is carrier, and the mol ratio between Cr and the Al is 1: 1～19.
3. the method for a kind of producing tetrafluoromethane by gas phase catalysis according to claim 1 and 2 is characterized in that, the method for producing tetrafluoromethane by gas phase catalysis comprises the steps:
(1) in proportion the mixture of one or more halohydrocarbon in a certain amount of tetrachloromethane, Trichloromonofluoromethane, Refrigerant 12, the monochlorotrifluoromethane and HF is contacted in reactor under 300～420 ℃ with described catalyzer, be 2～30 seconds duration of contact;
(2) product to step (1) carries out the knockout tower separating treatment, obtains the A cut at the bottom of the tower, cat head obtains the B cut;
(3) will from the A cut that step (2) obtain, reclaim HF and through be added to step (1) reactor as charging in, recycle; To deliver to water wash column washing from the B cut that step (2) obtain and separate, obtain the C cut at the bottom of the tower, cat head obtains the D cut;
(4) will after distilling, reclaim HCl from the C cut that step (3) obtain; The D cut that will obtain from step (3) is through alkali cleaning, drying and be collected in the cold-trap.From cold-trap, isolate and deliver to rectifying tower behind the tetrafluoromethane and carry out separating treatment, the gained mixture is delivered in step (1) reactor as charging and is recycled at the bottom of the pure tetrafluoromethane of recovered overhead, the tower, and isolated other mixture is delivered to the use of step (1) reactor cycles as charging after vaporizing from cold-trap.
4. the method for a kind of producing tetrafluoromethane by gas phase catalysis according to claim 2 is characterized in that, the preparation method of described catalysts for gas phase fluorination is: adopt Al (NO
3)
3, AlCl
3, Al
2O
3, AlO (OH), Al (OH)
3, AlF
3, Al
2(SO
4)
3, γ-Al
2O
3In one or more as the Al presoma; Adopt Cr (NO
3)
3, CrCl
3, Cr
2O
3, Cr (OH)
3, CrF
3, Cr (C
2H
3O
2)
3, Cr (OH) SO
4In one or more as the Cr presoma; Prepare throw out with the precipitator method, precipitation agent adopts a kind of in ammoniacal liquor, volatile salt, yellow soda ash, sodium hydroxide, the potassium hydroxide, throw out drying, roasting obtain this catalyst precursor, obtain the catalyzer of producing tetrafluoromethane by gas-phase fluorination again through hydrogen fluoride trealment.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102267866A (en) * | 2011-05-05 | 2011-12-07 | 浙江师范大学 | Preparation method for trifluoroethylene and tetrafluoroethane |
| CN108863710A (en) * | 2018-06-20 | 2018-11-23 | 临海市利民化工有限公司 | A kind of preparation method of tetrafluoromethane |
| TWI710545B (en) * | 2018-01-17 | 2020-11-21 | 日商昭和電工股份有限公司 | Manufacturing method of tetrafluoromethane |
| CN115838320A (en) * | 2023-02-28 | 2023-03-24 | 山东东岳化工有限公司 | Method for preparing monofluoromethane |
| CN116946978A (en) * | 2023-09-21 | 2023-10-27 | 山东东岳化工有限公司 | Method for preparing high-purity carbon tetrafluoride and chlorine |
-
2008
- 2008-10-16 CN CN200810121732A patent/CN101723797A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102267866A (en) * | 2011-05-05 | 2011-12-07 | 浙江师范大学 | Preparation method for trifluoroethylene and tetrafluoroethane |
| CN102267866B (en) * | 2011-05-05 | 2013-11-27 | 浙江师范大学 | Preparation method for trifluoroethylene and tetrafluoroethane |
| TWI710545B (en) * | 2018-01-17 | 2020-11-21 | 日商昭和電工股份有限公司 | Manufacturing method of tetrafluoromethane |
| US11034636B2 (en) | 2018-01-17 | 2021-06-15 | Showa Denko K.K. | Method for producing tetrafluoromethane |
| CN108863710A (en) * | 2018-06-20 | 2018-11-23 | 临海市利民化工有限公司 | A kind of preparation method of tetrafluoromethane |
| CN108863710B (en) * | 2018-06-20 | 2021-03-19 | 临海市利民化工有限公司 | Preparation method of tetrafluoromethane |
| CN115838320A (en) * | 2023-02-28 | 2023-03-24 | 山东东岳化工有限公司 | Method for preparing monofluoromethane |
| CN116946978A (en) * | 2023-09-21 | 2023-10-27 | 山东东岳化工有限公司 | Method for preparing high-purity carbon tetrafluoride and chlorine |
| CN116946978B (en) * | 2023-09-21 | 2024-02-02 | 山东东岳绿冷科技有限公司 | Method for preparing high-purity carbon tetrafluoride and chlorine |
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Application publication date: 20100609 |