WO2011122573A1 - 3-クロロ-ペンタフルオロプロペンの製造方法 - Google Patents
3-クロロ-ペンタフルオロプロペンの製造方法 Download PDFInfo
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- WO2011122573A1 WO2011122573A1 PCT/JP2011/057676 JP2011057676W WO2011122573A1 WO 2011122573 A1 WO2011122573 A1 WO 2011122573A1 JP 2011057676 W JP2011057676 W JP 2011057676W WO 2011122573 A1 WO2011122573 A1 WO 2011122573A1
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- chloride
- pentafluoropropene
- perfluoroallylfluorosulfate
- chloro
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
Definitions
- the present invention relates to a process for producing 3-chloro-pentafluoropropene.
- CPFP 3-Chloro-pentafluoropropene
- CPFP manufacturing methods For example, a method of thermally decomposing chlorotrifluoroethylene (for example, see Patent Document 1), a method of fluorinating 1,1,1,2,3,3,3-heptachloro-2-fluoropropane and then dechlorinating (See, for example, Non-Patent Document 1)
- a method of producing 1,2,3-trichloropentafluoropropane from chloroform and tetrachloroethylene through an addition reaction, a fluorination reaction, etc. by dechlorination reaction eg, patent Document 2 is known.
- Non-Patent Document 2 a method of chlorinating 3-iodo-pentafluoropropene or 3-bromo-pentafluoropropene
- Non-Patent Document 3 describes that 3-iodo-pentafluoropropene and 3-bromo-pentafluoropropene are produced from perfluoroallylfluorosulfate.
- Patent Documents 1 and 2 and Non-Patent Documents 1 and 2 require a multi-step reaction.
- a process for producing 3-iodo-pentafluoropropene or 3-bromo-pentafluoropropene from a raw material monomer and a chlorination process are required. is there.
- Non-Patent Document 3 does not describe a method for producing 3-chloro-pentafluoropropene.
- 3-iodo-pentafluoropropene is produced from perfluoroallylfluorosulfate by iodination using potassium iodide.
- 3-bromo-pentafluoropropene is produced from perfluoroallylfluorosulfate by bromination using potassium bromide.
- 3-chloro-pentafluoropropene could not be produced by chlorinating perfluoroallylfluorosulfate using potassium chloride instead of potassium iodide or potassium bromide.
- the present invention provides a method for producing CPFP in a high yield by a one-step reaction by chlorination of perfluoroallylfluorosulfate.
- the present invention includes a step of bringing 3-fluoro-pentafluoropropene (perfluoroallyl chloride) into contact with perfluoroallylfluorosulfate ester and an onium chloride compound to obtain 3-chloro-pentafluoropropene, It is a manufacturing method.
- the method for producing 3-chloro-pentafluoropropene of the present invention includes a step of obtaining 3-chloro-pentafluoropropene by contacting perfluoroallylfluorosulfate with an onium chloride compound.
- the perfluoroallylfluorosulfate is chlorinated, and 3-chloro-pentafluoropropene can be produced by a one-step reaction.
- the yield is also excellent.
- 3-chloro-pentafluoropropene can be produced from perfluoroallylfluorosulfate ester in a one-step reaction without using heavy metals, thereby simplifying the production process, Cost can be reduced. In addition, since no metal halide is produced, the problem of industrial waste does not occur.
- the compound which consists of an onium cation and a chloride ion is mentioned, for example.
- the onium cation include those containing a hetero atom and a hydrocarbon group such as an alkyl group or a phenyl group bonded thereto.
- the hetero atom include nitrogen, phosphorus, sulfur, oxygen, selenium, tin, iodine, and antimony.
- the hetero atom is preferably nitrogen, phosphorus, sulfur or oxygen, more preferably nitrogen or phosphorus, and still more preferably nitrogen.
- the onium chloride compound is preferably a hydrochloride.
- the onium chloride compound is preferably a salt of an amine and hydrogen chloride.
- the amine is obtained by substituting one or more hydrogen atoms constituting ammonia with a hydrocarbon group such as an alkyl group or a phenyl group.
- the onium chloride compound may be a salt (heterocyclic onium chloride compound) composed of a cation having a heterocyclic structure and a chloride ion.
- a heterocyclic onium chloride compound a salt of a heterocyclic nitrogen compound in which one or more carbon atoms of benzene or cyclohexane are replaced with a nitrogen atom and hydrogen chloride is preferable.
- the number of atoms constituting the heterocyclic ring is preferably 3 to 6, and more preferably 5 or 6.
- the heterocyclic ring only needs to have one or more heteroatoms. Although two or more heteroatoms may be used, it is preferable that one heteroatom constitutes one heterocyclic ring. Examples of the hetero atom include the same as described above, and among these, a nitrogen atom is preferable.
- the onium chloride compound is preferably liquid at a temperature at which the perfluoroallylfluorosulfate ester and the onium chloride compound are brought into contact with each other. By being liquid, the chlorination reaction can proceed efficiently, and the yield of CPFP can be further improved.
- the onium chloride compound is preferably soluble in perfluoroallylfluorosulfate.
- onium chloride compounds include ammonium chloride compounds, phosphonium chloride compounds, sulfonium chloride compounds, oxonium chloride compounds, and the like. You may use these individually or in combination of 2 or more types.
- ammonium chloride compound examples include salts of chloride ions and ammonium ions.
- the ammonium ion is a primary, secondary, tertiary or quaternary ammonium ion, preferably a tertiary or quaternary ammonium ion.
- an alkyl group having 1 to 20 carbon atoms an aryl group having 6 to 30 carbon atoms which may have a substituent, or 7 to 13 carbon atoms which may have a substituent.
- an ammonium ion having an aralkyl group is preferred.
- ammonium chloride compound is ammonium chloride
- the chlorination reaction does not proceed efficiently, and 3-chloro-pentafluoropropene can be obtained in high yield. Can not.
- the salt of the heterocyclic nitrogen compound and hydrogen chloride which may have a substituent can also be mentioned.
- the substituent that the heterocyclic nitrogen compound may have is preferably a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
- the salt of the above heterocyclic nitrogen compound and hydrogen chloride is a salt of a heterocyclic nitrogen compound and hydrogen chloride in which one or more carbon atoms constituting the ring of the cyclic compound such as benzene or cyclohexane are replaced with nitrogen atoms. And at least one compound selected from the group consisting of piperidine hydrochloride, pyridine hydrochloride, pyrrolidine hydrochloride, quinoline hydrochloride and 1-ethyl-3-methylimidazolidinium chloride is more preferable.
- the phosphonium chloride compound is preferably a salt composed of chloride ions and phosphonium ions.
- the phosphonium ion is a quaternary phosphonium ion, and has, for example, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which may have a substituent, or a substituent. It preferably has an aralkyl group having 7 to 13 carbon atoms.
- the sulfonium chloride compound is preferably a salt composed of chloride ion and sulfonium ion, and examples thereof include tertiary sulfonium salts such as methylmethionine sulfonium chloride.
- the oxonium chloride compound is preferably a salt composed of a chloride ion and an oxonium ion.
- the onium chloride compound is preferably at least one selected from the group consisting of an ammonium chloride compound and a phosphonium chloride compound, and more preferably an ammonium chloride compound.
- X is nitrogen or phosphorus
- R 1 , R 2 , R 3 and R 4 are the same or different and each represents a hydrogen atom or an alkyl having 1 to 20 carbon atoms which may have a substituent.
- R 1 , R 2 , R 3 and R 4 are the same or different and each represents a hydrogen atom or an alkyl having 1 to 20 carbon atoms which may have a substituent.
- a group consisting of a salt of a heterocyclic nitrogen compound optionally having a substituent and hydrogen chloride It is preferable that it is at least one kind.
- R 1 , R 2 , R 3 and R 4 are not hydrogen atoms
- at least one of R 1 , R 2 , R 3 and R 4 is an alkyl having 1 to 20 carbon atoms. Or an aryl group having 7 to 13 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent.
- the alkyl group in formula (1) is an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms. .
- the alkyl group may be a linear alkyl group or a branched alkyl group.
- the aryl group in the formula (1) is an aryl group having 6 to 30 carbon atoms, and preferably an aryl group having 6 to 10 carbon atoms. Specifically, at least one group selected from the group consisting of a phenyl group, a tolyl group, a xylyl group, a naphthyl group, and an anthranyl group is preferable.
- the aralkyl group in the formula (1) is an aralkyl group having 7 to 13 carbon atoms. Specifically, it is preferably at least one group selected from the group consisting of a benzyl group, a phenethyl group, and a naphthylmethyl group.
- the alkyl group, aryl group or aralkyl group may have a substituent.
- substituents include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, and a halogen atom. Is preferred.
- X in the formula (1) is more preferably nitrogen.
- specific compounds represented by the formula (1) include tetrabutylammonium chloride, trioctylmethylammonium chloride, trimethylphenylammonium chloride, tetraphenylammonium chloride, (methoxymethyl) triphenyl.
- Quaternary ammonium salts such as ammonium chloride, benzyltrimethylammonium chloride, 1-ethylpyridinium chloride, 1-ethyl-3-methylimidazolidinium chloride; tertiary amine hydrochlorides such as triethylamine hydrochloride, trimethylamine hydrochloride, pyridine hydrochloride Secondary amine hydrochlorides such as diethylamine hydrochloride; primary amine hydrochlorides such as ethylamine hydrochloride; and the like. Of these, at least one selected from the group consisting of tetrabutylammonium chloride and triethylamine hydrochloride is preferable.
- specific compounds represented by the formula (1) include tetrabutylphosphonium chloride, cyanomethyltributylphosphonium chloride, benzyltriphenylphosphonium chloride, tetraphenylphosphonium chloride, (methoxymethyl) trimethyl. Examples thereof include phenylphosphonium chloride. Of these, tetraphenylphosphonium chloride is preferable.
- any one of R 1 ⁇ R 4 is a hydrogen atom
- any three of R 1 ⁇ R 4 is a tertiary amine hydrochloride salt is an alkyl group Is more preferable
- triethylamine hydrochloride is more preferable because it is inexpensive and easily available.
- the salt of the heterocyclic nitrogen compound and hydrogen chloride is the same as described above.
- the onium chloride compound is at least one selected from the group consisting of a compound represented by the above formula (1) and a salt of a heterocyclic nitrogen compound which may have a substituent and hydrogen chloride.
- it is a compound represented by the above formula (1).
- R 1 , R 2 , R 3 and R 4 are the same or different and are preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, It is more preferably an alkyl group having 1 to 10 carbon atoms, and further preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
- the method of bringing the perfluoroallylfluorosulfate ester into contact with the onium chloride compound is not particularly limited as long as the perfluoroallylfluorosulfate ester is brought into contact with the onium chloride compound.
- a reaction vessel charged with the onium chloride compound For example, a method in which perfluoroallylfluorosulfate is dropped, and a method in which an onium chloride compound and perfluoroallylfluorosulfate are charged in a reaction vessel and stirred.
- a method of dropping perfluoroallylfluorosulfate is preferred.
- the onium chloride compound may be contacted with perfluoroallylfluorosulfate in a state dissolved in a solvent, or may be contacted with perfluoroallylfluorosulfate without solvent.
- the contact between the perfluoroallylfluorosulfate ester and the onium chloride compound may be carried out in a solvent or in the absence of a solvent.
- a contact was considered that sufficient yield could not be obtained if it was carried out in the absence of a solvent.
- CPFP can be produced in a sufficiently high yield even when contact is made in the absence of a solvent.
- an organic solvent or an ionic liquid is preferable. More preferably, the organic solvent or ionic liquid does not dissociate protons.
- the organic solvent or ionic liquid may contain water as long as the effects of the present invention are not impaired, but the organic solvent or ionic liquid preferably does not substantially contain water. This is because hydrolysis of the perfluoroallylfluorosulfuric acid ester, which is a raw material, may advance in advance due to moisture contained therein. If CPFP is isolated and purified by water washing or distillation, it is preferable to use a water-soluble one having a boiling point difference of 50 ° C. or more as compared with CPFP.
- organic solvents examples include ethers such as diethyl ether, ethyl methyl ether, diisopropyl ether, dibutyl ether, dibenzyl ether, diphenyl ether, oxetane, tetrahydrofuran, tetrahydropyran, dioxane, methyl acetate, ethyl acetate, acetic acid Esters such as propyl, isopropyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, isopentyl acetate, ketones such as acetone, methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, cyclohexanone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Ethylene glycol monobutyl ether, ethylene glycol dimethyl ether (monoglyme
- the solvent preferably has a volume of 0 to 200% with respect to perfluoroallylfluorosulfate in order to increase the stirring efficiency. More preferably, the capacity is 0 to 20%. The lower limit of the solvent capacity may be 1% with respect to the perfluoroallylfluorosulfate used.
- the temperature at the time of contact between the perfluoroallylfluorosulfate and the onium chloride compound is, for example, preferably ⁇ 20 to 50 ° C., and more preferably 0 to 30 ° C. It exists in the said range from the point which can suppress the pressure concerning a reaction container and can perform reaction rapidly.
- the reaction time is not particularly limited because it depends on the reaction conditions such as the type of solvent and temperature, but it is usually about 0.01 to 50 hours, and in order to sufficiently proceed the reaction, 0.1 to It is preferably about 15 hours.
- reaction pressure is not particularly limited, but can be carried out, for example, at ⁇ 0.01 to 1 MPa. In view of the simplicity of the production process, it is also preferable to carry out at atmospheric pressure (1 atm).
- the onium chloride compound is preferably present in excess relative to the perfluoroallylfluorosulfate ester.
- the onium chloride compound is a solid or a high-viscosity liquid, the amount of the onium chloride compound is preferably as small as possible in order to increase the stirring efficiency.
- the onium chloride compound to be contacted with the perfluoroallylfluorosulfate is preferably 1 to 3 equivalents relative to the perfluoroallylfluorosulfate.
- the obtained 3-chloro-pentafluoropropene may be purified by a known method such as distillation or column chromatography.
- the present invention includes a step of contacting a perfluoroallylfluorosulfate ester and an onium chloride compound in a reaction solvent to obtain a product solution containing 3-chloro-pentafluoropropene, and a step of distilling the obtained product solution.
- the manufacturing method containing these may be sufficient.
- distillation high purity 3-chloro-pentafluoropropene can be obtained.
- the obtained 3-chloro-pentafluoropropene can be identified using, for example, a gas chromatograph / mass spectrometer.
- CPFP can be produced from perfluoroallylfluorosulfate in a one-step reaction with a high yield.
- the yield can be, for example, 70% or more, or 80% or more.
- the above yield is the ratio of 3-chloro-pentafluoropropene (mol) obtained to perfluoroallylfluorosulfate ester (mol) used.
- 3-Chloro-pentafluoropropene obtained by the above method is a useful compound as an intermediate that can be derived into a raw material monomer of a fluororesin used for an ion exchange resin, a polymer electrolyte membrane or the like.
- the polymer electrolyte membrane or ion exchange resin is, for example, an electrolyte membrane for a solid polymer electrolyte fuel cell, a lithium battery membrane, a salt electrolysis membrane, a water electrolysis membrane, a hydrohalic acid electrolysis membrane, or an oxygen concentrator Used as membranes, membranes for humidity sensors, membranes for gas sensors, etc.
- CPFP can be produced in a high yield by a one-step reaction by chlorination of perfluoroallylfluorosulfate. Also, no heavy metal is used and no metal halide is produced, so that there is no problem of industrial waste.
- Example 1 Triethylamine hydrochloride (97 g, 703 mmol) and diglyme 50 mL were placed in a 300 mL four-necked flask equipped with a Dimroth condenser, dropping funnel, and thermometer, and stirred with a magnetic stirrer.
- the Dimroth condenser was cooled with a ⁇ 20 ° C. refrigerant, and the reaction flask was cooled to 0 ° C. with an ice bath.
- the distillation residue was confirmed by NMR analysis to contain carboxylic acid, ammonium fluorosulfate, and an excess amount of triethylamine hydrochloride, which are thought to have hydrolyzed unreacted perfluoroallylfluorosulfate during quenching.
- Example 2 The reaction was performed in the same manner as in Example 1 except that pyridine hydrochloride (81.0 g, 701 mmol) was used instead of triethylamine hydrochloride. As a result, 86.8 g of the target perfluoroallyl chloride was obtained with respect to the used perfluoroallylfluorosulfate (135 g, 586 mmol) (yield 89%).
- Example 3 instead of triethylamine hydrochloride, the trade name aliquat 336 (72.7 g, 180 mmol, a mixture of tri-n-octylmethylammonium chloride based on tri-n-octylmethylammonium chloride) was used, and 54 g of acetone was used as a solvent. Except for this, the reaction was carried out in the same manner as in Example 1. As a result, 11.9 g of the desired perfluoroallyl chloride was obtained with respect to the used perfluoroallylfluorosulfate (31.1 g, 135 mmol) (yield 53%).
- Example 4 The reaction was performed in the same manner as in Example 1 except that the solvent was not used. As a result, 87.7 g of the desired perfluoroallyl chloride was obtained with respect to the used perfluoroallylfluorosulfate ester (135 g, 586 mmol) (yield 90%).
- Example 5 The reaction was performed in the same manner as in Example 1 except that 50 mL of triethylamine fluorosulfate was used as the solvent. As a result, 89.8 g of the desired perfluoroallyl chloride was obtained with respect to the used perfluoroallylfluorosulfate (135 g, 586 mmol) (yield 92%).
- Example 6 The reaction was performed in the same manner as in Example 1 except that tetrabutylammonium chloride (14.5 g, 52.2 mmol) was used instead of triethylamine hydrochloride. As a result, 7.0 g of the desired perfluoroallyl chloride was obtained with respect to the used perfluoroallylfluorosulfate ester (10.0 g, 43.5 mmol) (yield 96.4%).
- Example 7 The reaction was performed in the same manner as in Example 1 except that tetraphenylphosphonium chloride (24.5 g, 65.3 mmol) was used instead of triethylamine hydrochloride. As a result, 2.4 g of the desired perfluoroallyl chloride was obtained with respect to the perfluoroallylfluorosulfate used (10.0 g, 43.5 mmol) (yield 32.5%).
- the 3-chloro-pentafluoropropene obtained by the production method of the present invention can be suitably used as an intermediate that can be derived into a raw material monomer of a fluororesin used for an ion exchange resin, a polymer electrolyte membrane or the like.
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Abstract
Description
CF2=CFCF2OSO2F
で表される化合物である。
ジムロート冷却管、滴下ロート、温度計を装備した300mLの4つ口フラスコにトリエチルアミン塩酸塩(97g、703mmol)とジグライム50mLを入れ、マグネティックスターラーで攪拌した。ジムロート冷却管は-20℃の冷媒で冷却し、反応フラスコは氷浴で0℃に冷却した。滴下ロートよりパーフルオロアリルフルオロ硫酸エステル(135g、586mmol)を、フラスコ内が10℃以下に保たれるように、およそ1時間かけて滴下した。滴下後、1時間攪拌し、ジムロート冷却管からリービッヒ蒸留装置に取り替えた。フラスコを室温(25℃)に戻し、生成物(沸点12℃)の蒸留を行った。フラスコに100mLの水を加え、反応を止めた。目的のパーフルオロアリルクロライド(純度99GC%)が90.7g蒸留分として得られた(収率93%)。蒸留残渣にはクエンチの際に未反応のパーフルオロアリルフルオロ硫酸エステルが加水分解したと思われるカルボン酸、フルオロ硫酸アンモニウム塩および過剰量のトリエチルアミン塩酸塩がNMR分析より確認された。
トリエチルアミン塩酸塩の代わりに、ピリジン塩酸塩(81.0g、701mmol)を用いたこと以外は、実施例1と同様にして反応を行った。その結果、用いたパーフルオロアリルフルオロ硫酸エステル(135g、586mmol)に対して目的のパーフルオロアリルクロライドが86.8g得られた(収率89%)。
トリエチルアミン塩酸塩の代わりに、商品名aliquat336(72.7g、180mmol、塩化トリn-オクチルメチルアンモニウムを主成分とした塩化トリn-デシルメチルアンモニウムとの混合物)を用い、溶媒としてアセトン54gを用いたこと以外は、実施例1と同様にして反応を行った。その結果、用いたパーフルオロアリルフルオロ硫酸エステル(31.1g、135mmol)に対して目的のパーフルオロアリルクロライドが11.9g得られた(収率53%)
溶媒を使用しなかったこと以外は、実施例1と同様にして反応を行った。その結果、用いたパーフルオロアリルフルオロ硫酸エステル(135g、586mmol)に対して目的のパーフルオロアリルクロライドが87.7g得られた(収率90%)
溶媒として、50mLのトリエチルアミンフルオロ硫酸塩を用いたこと以外は、実施例1と同様にして反応を行った。その結果、用いたパーフルオロアリルフルオロ硫酸エステル(135g、586mmol)に対して目的のパーフルオロアリルクロライドが89.8g得られた(収率92%)
トリエチルアミン塩酸塩の代わりに、塩化アンモニウム(37.4g、700mmol)を用いたこと以外は、実施例1と同様にして反応を行った。反応はほとんど進行せず、目的のパーフルオロアリルクロライドが3.5g得られた(収率3%)。
トリエチルアミン塩酸塩の代わりに、塩化カリウム(52.2g、700mmol)を用いたこと以外は、実施例1と同様にして反応を行った。反応は全く進行せず、原料のパーフルオロアリルフルオロ硫酸エステルと塩化カリウムが回収された。反応混合物はろ過を行い、ろ液はNMRとGC分析から原料のパーフルオロアリルフルオロ硫酸エステルであることを確認した。
トリエチルアミン塩酸塩の代わりに、テトラブチルアンモニウムクロライド(14.5g、52.2mmol)を用いたこと以外は、実施例1と同様にして反応を行った。その結果、用いたパーフルオロアリルフルオロ硫酸エステル(10.0g、43.5mmol)に対して目的のパーフルオロアリルクロライドが7.0g得られた(収率96.4%)。
トリエチルアミン塩酸塩の代わりに、テトラフェニルホスホニウムクロライド(24.5g、65.3mmol)を用いたこと以外は、実施例1と同様にして反応を行った。その結果、用いたパーフルオロアリルフルオロ硫酸エステル(10.0g、43.5mmol)に対して目的のパーフルオロアリルクロライドが2.4g得られた(収率32.5%)。
Claims (5)
- パーフルオロアリルフルオロ硫酸エステルと塩化オニウム化合物とを接触させて3-クロロ-ペンタフルオロプロペンを得る工程を含む
ことを特徴とする3-クロロ-ペンタフルオロプロペンの製造方法。 - パーフルオロアリルフルオロ硫酸エステルに接触させる塩化オニウム化合物は、パーフルオロアリルフルオロ硫酸エステルに対して1~3当量である請求項1、2又は3記載の3-クロロ-ペンタフルオロプロペンの製造方法。
- 前記接触は、-20~50℃で行われる請求項1、2、3又は4記載の3-クロロ-ペンタフルオロプロペンの製造方法。
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US13/638,302 US8816138B2 (en) | 2010-03-29 | 2011-03-28 | Method for producing 3-chloro-pentafluoropropene |
JP2012508319A JP5440692B2 (ja) | 2010-03-29 | 2011-03-28 | 3−クロロ−ペンタフルオロプロペンの製造方法 |
CN201180015382.XA CN102834366B (zh) | 2010-03-29 | 2011-03-28 | 3-氯-五氟丙烯的制造方法 |
EP11762797.6A EP2554530B2 (en) | 2010-03-29 | 2011-03-28 | Method for producing 3-chloro-pentafluoropropene |
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2011
- 2011-03-28 JP JP2012508319A patent/JP5440692B2/ja active Active
- 2011-03-28 CN CN201180015382.XA patent/CN102834366B/zh active Active
- 2011-03-28 WO PCT/JP2011/057676 patent/WO2011122573A1/ja active Application Filing
- 2011-03-28 EP EP11762797.6A patent/EP2554530B2/en active Active
- 2011-03-28 US US13/638,302 patent/US8816138B2/en active Active
Patent Citations (3)
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US3047639A (en) | 1960-03-22 | 1962-07-31 | Allied Chem | Manufacture of chlorofluoropropenes |
JPS61118333A (ja) | 1984-11-13 | 1986-06-05 | Daikin Ind Ltd | パ−フルオロアリルクロライドの製法 |
JP2009167120A (ja) * | 2008-01-15 | 2009-07-30 | Asahi Glass Co Ltd | パーフルオロアリルブロミドの製造方法 |
Non-Patent Citations (5)
Title |
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BANKS, R. E. ET AL.: "Perfluoroallyl Fluorosulphonate", JOURNAL OF FLUORINE CHEMISTRY, vol. 20, 1982, pages 133 - 134, XP008159692 * |
JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 70, 1948, pages 130 |
JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 79, 1957, pages 4170 - 4174 |
JOURNAL OF FLUORINE CHEMISTRY, vol. 20, 1982, pages 132 - 134 |
See also references of EP2554530A4 * |
Also Published As
Publication number | Publication date |
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EP2554530A4 (en) | 2015-10-14 |
US8816138B2 (en) | 2014-08-26 |
EP2554530B2 (en) | 2019-06-12 |
CN102834366A (zh) | 2012-12-19 |
JPWO2011122573A1 (ja) | 2013-07-08 |
US20130023704A1 (en) | 2013-01-24 |
CN102834366B (zh) | 2015-03-18 |
JP5440692B2 (ja) | 2014-03-12 |
EP2554530A1 (en) | 2013-02-06 |
EP2554530B1 (en) | 2016-07-13 |
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