CN1793094A - Process for preparing pentafluoroethylane - Google Patents
Process for preparing pentafluoroethylane Download PDFInfo
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- CN1793094A CN1793094A CN 200510097024 CN200510097024A CN1793094A CN 1793094 A CN1793094 A CN 1793094A CN 200510097024 CN200510097024 CN 200510097024 CN 200510097024 A CN200510097024 A CN 200510097024A CN 1793094 A CN1793094 A CN 1793094A
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- hydrogen fluoride
- tetrafluoroethylene
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- fluoride complex
- pentafluoride ethane
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Abstract
The invention relates to the manufacture method for penta-fluorin ethane. The feature is that the hydrogen fluoride complex is made up from the reaction of hydrogen fluoride, amine-group compound and carbonyl compound. The hydrogen fluoride complex and tetrafluoroethlene could take reaction to make penta-fluorin ethane. The invention is simple technology, mild reaction condition, high efficiency, and no pollution.
Description
Technical field
The present invention relates to a kind of preparation method of pentafluoride ethane, particularly a kind of method of utilizing tetrafluoroethylene and hydrogen fluoride complex to prepare pentafluoride ethane.
Background technology
The existing method of utilizing tetrafluoroethylene and hydrogen fluoride complex to prepare pentafluoride ethane, as U.S. Pat 5847245, the disclosed method of producing pentafluoride ethane of US5969199 by tetrafluoroethylene and the reaction of hydrofluoric complex compound, this method can be directly by tetrafluoroethylene and the synthetic pentafluoride ethane of hydrogen fluoride addition reaction, reaction is simple, does not produce environmental pollutant; But used hydrogen fluoride complex is the reaction product of hydrogen fluoride and aminated compounds, and this hydrofluoric complex compound reactive behavior is lower, easily forms crystallisate and loses response capacity, and not only the product yield is low, and purity is not high, especially is difficult to use in suitability for industrialized production.
Summary of the invention
At above problem, the purpose of this invention is to provide the pentafluoride ethane preparation method of all very high and suitable suitability for industrialized production of a kind of product yield and purity.
A kind of preparation method of pentafluoride ethane utilizes tetrafluoroethylene and hydrogen fluoride complex to prepare the method for pentafluoride ethane, it is characterized in that: hydrogen fluoride complex is the complex compound that hydrogen fluoride, aminated compounds and carbonyl compound reaction generate.
The present invention is hydrogen fluoride complex and the tetrafluoroethylene prepared in reaction pentafluoride ethane that generates with hydrogen fluoride, aminated compounds and carbonyl compound reaction.The hydrogen fluoride complex that generates because of hydrogen fluoride, aminated compounds and carbonyl compound reaction is active strong, is difficult for forming crystallisate and loses response capacity; So the present invention not only reacts simply, the reaction conditions gentleness, the production efficiency height does not produce environmental pollutant, and product yield and purity are all very high, is fit to suitability for industrialized production.
Embodiment
Describe in detail below in conjunction with embodiment:
Embodiment one:
A kind of hydrogen fluoride complex and tetrafluoroethylene of producing with hydrogen fluoride, aminated compounds and carbonyl compound prepares pentafluoride ethane.5 kilograms the hydrogen fluoride complex that generates with hydrogen fluoride, aminated compounds and carbonyl compound reaction is joined in 10 liters of autoclaves, be warming up to 80 ℃, add 1 kilogram in tetrafluoroethylene, stirring fast makes tetrafluoroethylene fully contact with hydrogen fluoride complex, reacted 0.3 hour, gas chromatographic analysis shows tetrafluoroethylene transformation efficiency 96%, separate 0.97 kilogram of product pentafluoride ethane, purity 96%.
Embodiment two:
A kind of hydrogen fluoride complex and synthetic pentafluoride ethane of producing with hydrogen fluoride, aminated compounds and carbonyl compound of tetrafluoroethylene.It is in 10 liters the highly compressed of the anti-1.0MPa tubular reactor (2.5 centimetres of internal diameters) that the hydrogen fluoride complex that 9 kilograms hydrogen fluoride, aminated compounds and carbonyl compound reaction are generated joins internal volume, be warming up to 90 ℃, slowly feed 2 kilograms in tetrafluoroethylene from Guan Yiduan, tetrafluoroethylene is fully contacted with hydrogen fluoride complex, and gas is overflowed through the other end.Gas chromatographic analysis shows that tetrafluoroethylene content is 2% in the evolving gas, and pentafluoride ethane content is 98%.Collect gas, through separate the product pentafluoride ethane, purity 99.6%.
Embodiment three
A kind of method of producing pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene.At first with hydrogen fluoride, aminated compounds, carbonyl compound by 1: 0.1-50: the 0.1-100 mol ratio is weighed, and mixes under-20 ℃～50 ℃, makes the hydrogen fluoride complex that share, and its general formula is (HF) m (A) n (B) x, wherein:
HF is a hydrogen fluoride.
A is an aminated compounds, can be that a kind of aminated compounds also can be the mixture of some kinds of aminated compoundss.As: can be methylamine, ethamine, Tri N-Propyl Amine, n-Butyl Amine 99, dimethylamine, diethylamine, di-n-propylamine, Di-n-Butyl Amine, Trimethylamine 99, triethylamine, Tri-n-Propylamine, tri-n-butylamine, sec.-propyl diethylamine, N, accelerine, N-methyl piperidine, pyridine, quinoline, pyrroles, N, N, N, N-Tetramethyl Ethylene Diamine, N, N, N, a certain in the aminated compoundss such as N-4-methyl-diaminopropane also can be some kinds mixture wherein.
B is a carbonyl compound, can be a kind of carbonyl compound, also can be the mixture of some kinds of carbonyl compound.As: can be acetone, butanone, metacetone, butyrone, methyl ethyl ketone, methyl hexyl ketone, pimelinketone, cyclooctanone, 2,3-dimethyl diketone, 2,5-hexanedione, 1, a certain in the carbonyl compound such as hydroresorcinol, methyl phenyl ketone, Propiophenone, isophorone, tetralone also can be some kinds mixture wherein.
M, n, x are the numerals of 0.1-100, represent the mole number of HF, A, B; They should meet the ratio of m: n: x=1: 0.1-50: 0.1-100.
Must notice that in this mixing process hydrogen fluoride have strong corrosion, and three kinds of materials react and emit a large amount of caloric requirements and in time cool off in this mixing process.
Then, this hydrogen fluoride complex is transferred to (reactor can be still formula, tower or duct type in the reactor, or other reactors), be warming up to 50 ℃～300 ℃, add tetrafluoroethylene, and tetrafluoroethylene is fully contacted with hydrogen fluoride complex, and reacted 0.01～1 hour, make the product pentafluoride ethane.Add tetrafluoroethylene after just the hydrogen fluoride complex that hydrogen fluoride, aminated compounds and carbonyl compound reaction are generated is warming up to 50 ℃～300 ℃ in reactor, and tetrafluoroethylene is fully contacted with hydrogen fluoride complex, react and make after 0.01～1 hour.
When carrying out above-mentioned reaction and produce pentafluoride ethane, the quality of single and the tetrafluoroethylene of hydrogen fluoride complex reaction can be 0.1-10 a times of hydrogen fluoride quality in the hydrogen fluoride complex.
In order to guarantee sufficient reacting completely, can in the process of tetrafluoroethylene and hydrogen fluoride complex reaction or after reacting, add hydrogen fluoride, the hydrogen fluoride that supplement consumed is fallen as required; Hydrofluoric interpolation quality is 0.2 times of the tetrafluoroethylene quality that reacts away with hydrogen fluoride complex.
For reacting fully fully, with the process of tetrafluoroethylene reaction in or add used up hydrogen fluoride complex after the reaction, can carry out again producing pentafluoride ethane with the reaction of tetrafluoroethylene.Hydrogen fluoride complex is added 0.2 times of quality that used up hydrofluoric quality should be the tetrafluoroethylene that reacts away with hydrogen fluoride complex.
Embodiment four:
A kind of method for preparing pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene.
At first, take by weighing hydrogen fluoride 1000 grams, n-Butyl Amine 99 9250 grams, pimelinketone 4900 grams.Hydrogen fluoride is added in the stainless steel cauldron of band stirring system and cooling system, under stirring and cooling off, slowly add n-Butyl Amine 99 and pimelinketone simultaneously, keep their adding speed to remain on substantially 925: 490, make temperature of reaction remain on-15 ℃ simultaneously.After all material adds well, keep stirring 1 hour, slowly be warmed up to normal temperature then, be spendable hydrogen fluoride complex.
Then, with 5000 restrain hydrogen fluoride complex join in 10 liters of autoclaves, be warmed up to 80 ℃, add 1000 gram tetrafluoroethylene continuously, stirring makes hydrogen fluoride complex fully contact with tetrafluoroethylene fast, reacts 0.3 hour, and gas chromatographic analysis shows tetrafluoroethylene transformation efficiency 96%, separate to such an extent that pentafluoride ethane 970 restrains purity 96%.
Embodiment five
A kind of method for preparing pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene.
At first, take by weighing hydrogen fluoride 1000 grams, N, N, N, N-4-methyl-diaminopropane 260 grams, methyl phenyl ketone 8100 grams.Hydrogen fluoride is added in the stainless steel cauldron of band stirring system and cooling system, under stirring and cooling off, slowly add N simultaneously, N, N, N,-4-methyl-diaminopropane and methyl phenyl ketone keep their adding speed to remain on substantially 26: 810, make temperature of reaction remain on-15 ℃ simultaneously.After all material adds well, keep stirring 1 hour, slowly be warmed up to normal temperature then, be spendable hydrogen fluoride complex.
Then, the 5000 gram hydrogen fluoride complexes that make are joined in 10 liters of autoclaves, be warmed up to 55 ℃, intermittently repeatedly add tetrafluoroethylene, totally 1000 restrain, stirring makes hydrogen fluoride complex fully contact with tetrafluoroethylene fast, reacted 0.9 hour, gas chromatographic analysis shows tetrafluoroethylene transformation efficiency 99%, separates to such an extent that pentafluoride ethane 940 restrains purity 99%.
Embodiment six
A kind of method of producing pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene.
At first, take by weighing hydrogen fluoride 1000 grams, Di-n-Butyl Amine 1250 grams, pyridine 5200 grams, methyl ethyl ketone 9000 grams.Hydrogen fluoride is added in the stainless steel cauldron of band stirring system and cooling system, under stirring and cooling off, slowly add Di-n-Butyl Amine, pyridine and methyl ethyl ketone simultaneously, keep their adding speed to remain on substantially 125: 520: 900, make temperature of reaction remain on-10 ℃ simultaneously.After all material adds well, keep stirring 1 hour, slowly be warmed up to normal temperature then, be spendable hydrogen fluoride complex.
Then, the 15000 gram hydrogen fluoride complexes that make are joined in the withstand voltage tower reactor of 20 liters of internal volumes, be warmed up to 260 ℃, add 5000 gram tetrafluoroethylene continuously, add the hydrogen fluoride of 1000 gram hydrogen fluoride simultaneously continuously with supplement consumed.Place filler so that hydrogen fluoride complex fully contacts with tetrafluoroethylene in tower reactor, reacted 0.6 hour, gas chromatographic analysis shows tetrafluoroethylene transformation efficiency 97%, separates to such an extent that pentafluoride ethane 4890 restrains purity 95.9%.
Embodiment seven
A kind of method for preparing pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene.
At first, take by weighing hydrogen fluoride 1000 grams, pyrroles's 22000 grams, methylamine 28000 grams, 2,3-dimethyl diketone 9000 grams, isophorone 65000 grams.Hydrogen fluoride is added in the stainless steel cauldron of band stirring system and cooling system, under stirring and cooling off, slowly add pyrroles, methylamine and 2 simultaneously, 3-dimethyl diketone, isophorone, keep their adding speed to remain on substantially 22: 28: 9: 65, make temperature of reaction remain on-10 ℃ simultaneously.After all material adds well, keep stirring 3 hours, slowly be warmed up to normal temperature then, be spendable hydrogen fluoride complex.
Then, the 50000 gram hydrogen fluoride complexes that make are joined in the pipeline reactor of 100 liters of internal volumes, pipeline reactor connects a liquor pump so that inner material can flow fast, and baffle plate is placed so that inner material can fully contact in inside simultaneously.Be warmed up to 250 ℃, add 20000 gram tetrafluoroethylene continuously, reacted 1 hour, gas chromatographic analysis shows tetrafluoroethylene transformation efficiency 99%, separates to such an extent that pentafluoride ethane 19200 restrains purity 98.5%.
Embodiment eight
A kind of method for preparing pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene.
At first, with used hydrogen fluoride complex 5000 grams among the embodiment five, add in the stainless steel cauldron of band stirring system and cooling system, under stirring and cooling off, slowly add hydrogen fluoride 200 grams, add good back and continue to stir 1 hour, promptly obtain and spendable hydrogen fluoride complex.
Then, the 5000 gram hydrogen fluoride complexes that make are joined in 10 liters of autoclaves, be warmed up to 55 ℃, intermittently repeatedly add tetrafluoroethylene, totally 1000 restrain, stirring makes hydrogen fluoride complex fully contact with tetrafluoroethylene fast, reacted 0.9 hour, gas chromatographic analysis shows tetrafluoroethylene transformation efficiency 99%, separates to such an extent that pentafluoride ethane 940 restrains purity 99%.
Obviously, preparing the method for pentafluoride ethane with hydrogen fluoride, aminated compounds, carbonyl compound and tetrafluoroethylene, is earlier with hydrogen fluoride, aminated compounds, carbonyl compound reaction the becoming hydrogen fluoride complex that share; Then, this hydrogen fluoride complex is transferred in the reactor, is warming up to 50 ℃～300 ℃, add tetrafluoroethylene, and tetrafluoroethylene is fully contacted with hydrogen fluoride complex, react and make after 0.01～1 hour.Tetrafluoroethylene can once, continuously or intermittently adding.
Embodiment nine
A kind of preparation of hydrogen fluoride complex.
Take by weighing 50 moles in hydrogen fluoride, 50 moles of n-Butyl Amine 99s, 50 moles of pimelinketone.Hydrogen fluoride is added in the stainless steel cauldron of band stirring system, cooling system, under stirring and cooling, slowly add n-Butyl Amine 99 and pimelinketone simultaneously, keep the adding speed of n-Butyl Amine 99 and pimelinketone identical, and control adding speed and cooling efficiency, make temperature of reaction remain on-15 ℃.After all material adds well, keep stirring 1 hour, slowly be warmed up to normal temperature then, be spendable hydrogen fluoride complex.
Claims (7)
1, a kind of preparation method of pentafluoride ethane utilizes tetrafluoroethylene and hydrogen fluoride complex to prepare the method for pentafluoride ethane, it is characterized in that: hydrogen fluoride complex is the complex compound that hydrogen fluoride, aminated compounds and carbonyl compound reaction generate.
2, the preparation method of pentafluoride ethane according to claim 1, it is characterized in that: add tetrafluoroethylene the hydrogen fluoride complex that hydrogen fluoride, aminated compounds and carbonyl compound reaction are generated is warming up to 50 ℃～300 ℃ in reactor after, and tetrafluoroethylene is fully contacted with hydrogen fluoride complex, react and make after 0.01～1 hour.
3, the preparation method of pentafluoride ethane according to claim 2 is characterized in that: add hydrogen fluoride in the process of tetrafluoroethylene and hydrogen fluoride complex reaction or after reacting.
4, the preparation method of pentafluoride ethane according to claim 3 is characterized in that: hydrofluoric interpolation quality is 0.2 times of the tetrafluoroethylene quality that reacts away with hydrogen fluoride complex.
5, according to the preparation method of claim 1,2,3 or 4 described pentafluoride ethanes, it is characterized in that: the quality of the tetrafluoroethylene of single and hydrogen fluoride complex reaction can be 0.1-10 a times of hydrogen fluoride quality in the hydrogen fluoride complex.
6, the preparation method of pentafluoride ethane according to claim 5 is characterized in that: once, continuously or intermittently adding of tetrafluoroethylene.
7, according to the preparation method of claim 1,2,3 or 4 described pentafluoride ethanes, it is characterized in that: once, continuously or intermittently adding of tetrafluoroethylene.
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| CNB2005100970244A CN100354242C (en) | 2005-12-29 | 2005-12-29 | Process for preparing pentafluoroethylane |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999439B (en) * | 2007-01-04 | 2010-10-06 | 西安近代化学研究所 | Preparation method of pentafluoroethane |
| CN110787836A (en) * | 2019-11-15 | 2020-02-14 | 常熟三爱富中昊化工新材料有限公司 | Method for prolonging service cycle of catalyst for heptafluoropropane synthesis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SG46638A1 (en) * | 1993-07-12 | 1998-02-20 | Solvay | Process for the addition of hf to halogenated alkenes |
| CN1286786C (en) * | 2004-07-22 | 2006-11-29 | 山东东岳高分子材料有限公司 | Production method of pentafluoroethane |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999439B (en) * | 2007-01-04 | 2010-10-06 | 西安近代化学研究所 | Preparation method of pentafluoroethane |
| CN110787836A (en) * | 2019-11-15 | 2020-02-14 | 常熟三爱富中昊化工新材料有限公司 | Method for prolonging service cycle of catalyst for heptafluoropropane synthesis |
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Effective date of registration: 20090508 Address after: Zhejiang Province, Jinhua City, Wucheng Development Zone, Jin Xi Tang Xi Zhen Zhejiang Xingteng Chemical Co Ltd postcode: 321075 Patentee after: Xingteng Chemical Co., Ltd., Zhejiang Address before: Zhejiang Province, Jinhua City, Wucheng Development Zone, Jin Xi Tang Xi Zhen Zhejiang Xingteng Chemical Co Ltd postcode: 321075 Co-patentee before: Shanghai Teng fluorine polymer materials research institute Patentee before: Zhejiang Star Chemical Co., Ltd. |
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Owner name: JINHUA YONGHE FLUOROCHEMICAL CO., LTD. Free format text: FORMER NAME: XINGTENG CHEMICAL CO., LTD., ZHEJIANG |
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Address after: 321075 Zhejiang Province, Jinhua city Wucheng District Development Zone Jinxi Tangxi town Zhejiang Xingteng Chemical Co Ltd Patentee after: Jinhua Yonghe Fluorochemical Co., Ltd. Address before: 321075 Zhejiang Province, Jinhua city Wucheng District Development Zone Jinxi Tangxi town Zhejiang Xingteng Chemical Co Ltd Patentee before: Xingteng Chemical Co., Ltd., Zhejiang |
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Owner name: ZHEJIANG YONGHE REFRIGERATION CO., LTD. Effective date: 20131106 |
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Effective date of registration: 20131106 Address after: 321075 Zhejiang Province, Jinhua city Wucheng District Development Zone Jinxi Tangxi town Zhejiang Xingteng Chemical Co Ltd Patentee after: Jinhua Yonghe Fluorochemical Co., Ltd. Patentee after: Zhejiang Yonghe Refrigerant Co., Ltd. Address before: 321075 Zhejiang Province, Jinhua city Wucheng District Development Zone Jinxi Tangxi town Zhejiang Xingteng Chemical Co Ltd Patentee before: Jinhua Yonghe Fluorochemical Co., Ltd. |