JP6470765B2 - ハロゲン化エタンで汚染された(ハイドロ)フルオロプロペンを精製するためのプロセス - Google Patents
ハロゲン化エタンで汚染された(ハイドロ)フルオロプロペンを精製するためのプロセス Download PDFInfo
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- JP6470765B2 JP6470765B2 JP2016571746A JP2016571746A JP6470765B2 JP 6470765 B2 JP6470765 B2 JP 6470765B2 JP 2016571746 A JP2016571746 A JP 2016571746A JP 2016571746 A JP2016571746 A JP 2016571746A JP 6470765 B2 JP6470765 B2 JP 6470765B2
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- 238000000034 method Methods 0.000 title claims description 94
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 title description 26
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title description 21
- 239000003463 adsorbent Substances 0.000 claims description 83
- 239000003507 refrigerant Substances 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 38
- 238000010438 heat treatment Methods 0.000 claims description 24
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 17
- 239000011148 porous material Substances 0.000 claims description 17
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002808 molecular sieve Substances 0.000 claims description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 12
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical group FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 11
- 230000008929 regeneration Effects 0.000 claims description 9
- 238000011069 regeneration method Methods 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 7
- 238000005498 polishing Methods 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 239000013529 heat transfer fluid Substances 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052756 noble gas Inorganic materials 0.000 claims description 2
- 150000002835 noble gases Chemical class 0.000 claims description 2
- 230000001172 regenerating effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- -1 ethane halide Chemical class 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000002156 adsorbate Substances 0.000 description 4
- 238000004378 air conditioning Methods 0.000 description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
- B01D53/0407—Constructional details of adsorbing systems
- B01D53/0438—Cooling or heating systems
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C17/38—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
- F25B43/00—Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat
- F25B43/003—Filters
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2259/40—Further details for adsorption processes and devices
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- B01D2259/40088—Regeneration of adsorbents in processes other than pressure or temperature swing adsorption by heating
- B01D2259/4009—Regeneration of adsorbents in processes other than pressure or temperature swing adsorption by heating using hot gas
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- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
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- Y02C20/30—Capture or disposal of greenhouse gases of perfluorocarbons [PFC], hydrofluorocarbons [HFC] or sulfur hexafluoride [SF6]
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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- Treatment Of Liquids With Adsorbents In General (AREA)
Description
吸着剤による気相吸着質の吸収量を、TGA分析器によってリアルタイムで測定した。以下の吸着剤を試験した。
分子ふるい3A−約3Åのその最大寸法にわたるサイズを有する開口を有する細孔
分子ふるい4A−約4Åのその最大寸法にわたるサイズを有する開口を有する細孔
分子ふるい5A−約5Åのその最大寸法にわたるサイズを有する開口を有する細孔
分子ふるい13X−約10Åのその最大寸法にわたるサイズを有する開口を有する細孔
及びケムビロン(Chemviron)207ea活性炭。
Claims (53)
- 1つ以上の所望のテトラフルオロプロペン及び1,1,1,2−テトラフルオロエタン(134a)を含む組成物を処理して、134aの濃度を低減させるためのプロセスであって、前記プロセスが、前記組成物を、6Å以下のその最大寸法にわたるサイズを有する開口を有する細孔を備える吸着剤と接触させることを含む、プロセス。
- 前記所望のテトラフルオロプロペンが、処理される前記組成物の少なくとも10重量%を構成する、請求項1に記載のプロセス。
- 前記所望のテトラフルオロプロペンが、処理される前記組成物の少なくとも50重量%を構成する、請求項2に記載のプロセス。
- 前記所望のテトラフルオロプロペンが、処理される前記組成物の少なくとも90重量%を構成する、請求項3に記載のプロセス。
- 前記吸着剤が、4Å〜6Åのそれらの最大寸法にわたるサイズを有する開口を有することを含む、請求項1〜4のいずれか一項に記載のプロセス。
- 前記吸着剤が、5Åのそれらの最大寸法にわたるサイズを有する開口を有する細孔を備える、請求項1〜5のいずれか一項に記載のプロセス。
- 前記吸着剤が、分子ふるいである、請求項1〜6のいずれか一項に記載のプロセス。
- 前記吸着剤が、ゼオライトを含む、請求項1〜7のいずれか一項に記載のプロセス。
- 前記テトラフルオロプロペンが、2,3,3,3−テトラフルオロプロペン(1234yf)である、請求項1に記載のプロセス。
- 前記接触ステップは、少なくともその一部が、0℃〜200℃の温度で行われる、請求項1〜9のいずれか一項に記載のプロセス。
- 前記接触ステップは、少なくともその一部が、20℃〜100℃の温度で行われる、請求項10に記載のプロセス。
- 前記接触ステップは、少なくともその一部が、20℃〜60℃の温度で行われる、請求項11に記載のプロセス。
- 前記温度が40℃である、請求項12に記載のプロセス。
- 前記接触ステップが、0.1MPa〜前記組成物の成分の飽和圧力の圧力で行われる、請求項1〜13のいずれか一項に記載のプロセス。
- 前記接触ステップの前に、吸着剤処理ステップをさらに含む、請求項1〜14のいずれか一項に記載のプロセス。
- 前記吸着剤処理ステップが、前記吸着剤を少なくとも150℃の最高温度まで加熱することを含む熱処理ステップを含む、請求項15に記載のプロセス。
- 前記吸着剤処理ステップが、前記吸着剤を少なくとも200℃の最高温度まで加熱することを含む熱処理ステップを含む、請求項16に記載のプロセス。
- 前記熱処理ステップが、前記吸着剤を少なくとも300℃の最高温度まで加熱することを含む、請求項16又は17に記載のプロセス。
- 前記熱処理ステップが、前記吸着剤を少なくとも400℃の最高温度まで加熱することを含む、請求項18に記載のプロセス。
- 前記熱処理ステップが、前記吸着剤を1℃/分〜100℃/分の速度で、前記最高温度まで加熱することを含む、請求項17〜19のいずれか一項に記載のプロセス。
- 前記熱処理ステップが、前記吸着剤を10℃/分〜60℃/分の速度で、前記最高温度まで加熱することを含む、請求項20に記載のプロセス。
- 前記熱処理ステップが、前記吸着剤を20℃/分〜40℃/分の速度で、前記最高温度まで加熱することを含む、請求項21に記載のプロセス。
- 前記熱処理ステップが、前記吸着剤を前記最高温度またはその付近で1秒間〜1時間維持することを含む、請求項17〜22のいずれか一項に記載のプロセス。
- 前記吸着剤処理ステップが、前記吸着剤を1種以上の不活性ガスに曝露することを含む曝露ステップを含む、請求項14〜23のいずれか一項に記載のプロセス。
- 前記不活性ガスがN2または1つ以上の希ガスである、請求項24に記載のプロセス。
- 前記曝露ステップが、前記熱処理ステップ前に、そのステップ中に、またはそのステップ後に行われる、請求項24または25に記載のプロセス。
- 前記プロセスが、134aの少なくとも50重量%を除去する、請求項1〜26のいずれか一項に記載のプロセス。
- 前記プロセスが、134aの少なくとも90重量%を除去する、請求項27に記載のプロセス。
- 前記プロセスが、134aの少なくとも98重量%を除去する、請求項28に記載のプロセス。
- 前記プロセスが、134aの濃度を、ガスクロマトグラフィーによる検出限界の、その付近の、またはそれを下回るレベルまで低減させる、請求項27〜29のいずれか一項に記載のプロセス。
- 前記吸着剤が、使用前に乾燥される、請求項1〜30のいずれか一項に記載のプロセス。
- 前記吸着剤の水分量が、1.5重量%未満である、請求項1〜31のいずれか一項に記載のプロセス。
- 前記処理される組成物が、前記吸着剤を含有する研磨層を、少なくとも一度通過し、前記研磨層が粒状吸着体層である、請求項1〜32のいずれか一項に記載のプロセス。
- 前記組成物が、2つ以上の研磨層を通過する、請求項33に記載のプロセス。
- 前記研磨層が、充填層または流動層を含む、請求項33または34に記載のプロセス。
- 前記組成物が、前記吸着剤と複数回接触する、請求項1〜35のいずれか一項に記載のプロセス。
- 前記吸着剤を、前記組成物と接触させた後に再生するステップをさらに含む、請求項1〜36のいずれか一項に記載のプロセス。
- 前記再生ステップが、前記吸着剤を加熱された不活性ガス流と接触させること、及び/または、前記または1つの不活性ガスが前記吸着剤上を通過する間、前記吸着剤を加熱することを含む、請求項37に記載のプロセス。
- 前記再生ステップが、前記吸着剤に圧力変化を受けさせることを含む、請求項37または38に記載のプロセス。
- 前記接触ステップの前及び/またはその後に行われ得る、1つ以上の付加的な精製ステップをさらに含む、請求項1〜39のいずれか一項に記載のプロセス。
- 前記付加的な精製ステップが、1つ以上の分子ふるいの使用を含む、請求項40に記載のプロセス。
- 前記1つ以上の分子ふるいが、酸安定性である、請求項41に記載のプロセス。
- 前記付加的な精製ステップが、乾燥剤及び/または蒸留技法の使用を含む、請求項40〜42のいずれか一項に記載のプロセス。
- 前記プロセスは、少なくともその一部が、気相または液相において行われる、請求項1〜43のいずれか一項に記載のプロセス。
- 使用済み冷媒の所望の成分を回収するための方法であって、前記方法が、冷媒システムから前記冷媒を除去することと、前記冷媒を、6Å以下のその最大寸法にわたって開口するサイズを有する細孔を備える吸着剤と接触させて、1つ以上の不所望の成分を除去するかまたは濃度を低減させることとを含み、前記所望の成分が、テトラフルオロプロペンを含み、前記不所望の成分が、134aを含む、方法。
- 前記所望のテトラフルオロプロペンが、前記使用済み冷媒の少なくとも10重量%を構成する、請求項45に記載の方法。
- 前記所望のテトラフルオロプロペンが、前記使用済み冷媒の少なくとも50重量%を構成する、請求項46に記載の方法。
- 前記所望のテトラフルオロプロペンが、前記使用済み冷媒の少なくとも90重量%を構成する、請求項45に記載の方法。
- 使用済み冷媒の所望の成分を回収するためのキットであって、前記キットが、6Å以下のその最大寸法にわたって開口するサイズを有する細孔を備える吸着剤を備える機器と、冷媒システムから前記冷媒を除去し、前記冷媒を前記機器と接触させて、1つ以上の不所望の成分を除去するかまたは濃度を低減させるための説明書とを備え、前記所望の成分が、テトラフルオロプロペンを含み、前記不所望の成分が、134aを含む、キット。
- 前記所望のテトラフルオロプロペンが、前記冷媒の少なくとも10重量%を構成する、請求項49に記載のキット。
- 前記所望のテトラフルオロプロペンが、前記冷媒の少なくとも50重量%を構成する、請求項50に記載のキット。
- 前記所望のテトラフルオロプロペンが、前記冷媒の少なくとも90重量%を構成する、請求項51に記載のキット。
- 少なくとも1つの所望のテトラフルオロプロペンを含み、134aを実質的に含まない伝熱流体を製造するプロセスであって、該プロセスが少なくとも1つのテトラフルオロプロペンが、請求項1〜44のいずれか一項に記載のプロセスによって精製されることを特徴とする、プロセス。
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GBGB1410174.5A GB201410174D0 (en) | 2014-06-09 | 2014-06-09 | Process |
PCT/GB2015/051671 WO2015189585A1 (en) | 2014-06-09 | 2015-06-09 | Process for purifying (hydro)fluoropropenes contaminated with halogenated ethane |
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Family Cites Families (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3446645A (en) * | 1968-05-06 | 1969-05-27 | Union Carbide Corp | Desiccant bodies |
US3625866A (en) | 1969-07-24 | 1971-12-07 | Union Carbide Corp | Zeolitic desiccant bodies and process for preparing same |
US3865887A (en) | 1972-06-21 | 1975-02-11 | Continental Oil Co | Process for removing lower alkyl chlorides from vinyl chloride monomers |
JPS6327968A (ja) | 1986-07-22 | 1988-02-05 | Toshiba Corp | 文書作成装置 |
JPS6443346A (en) | 1987-08-06 | 1989-02-15 | Union Showa Kk | Zeolite compact |
US4906796A (en) | 1989-03-08 | 1990-03-06 | Allied Signal Inc. | Process for purifying 1,1,1,2-tetrafluoroethane |
JPH0372437A (ja) | 1989-08-10 | 1991-03-27 | Showa Denko Kk | 1,1,1,2―テトラフルオロエタンの精製法 |
US4940824A (en) | 1989-12-14 | 1990-07-10 | Allied-Signal Inc. | Process for removing vinylidene chloride from 1,1-dichloro-1-fluoroethane |
JPH04110388A (ja) | 1990-08-31 | 1992-04-10 | Daikin Ind Ltd | 熱伝達用流体 |
US5164355A (en) | 1991-01-23 | 1992-11-17 | Air Products And Chemicals, Inc. | High capacity coconut shell char for carbon molecular sieves |
US5156768A (en) | 1991-04-05 | 1992-10-20 | Allied-Signal Inc. | Stabilized chlorine-containing refrigeration compositions |
JPH0656713A (ja) | 1991-04-27 | 1994-03-01 | Hoechst Ag | クロロフルオロ炭化水素の精製方法 |
US5288930A (en) * | 1991-08-02 | 1994-02-22 | Imperial Chemical Industries Plc | Purification of 1,1,1,2-tetrafluoroethane |
WO1993017988A1 (en) | 1992-03-10 | 1993-09-16 | E.I. Du Pont De Nemours And Company | Purification of hexafluoroethane products |
US5575833A (en) * | 1992-09-25 | 1996-11-19 | Parker-Hannifin Corporation | Refrigerant recycling system and apparatus |
BE1006432A3 (fr) | 1992-12-02 | 1994-08-23 | Solvay | Procede de purification de 1,1-difluoroethane. |
JP3213828B2 (ja) | 1993-05-24 | 2001-10-02 | ユニオン昭和株式会社 | HFC−32、HFC−152a用乾燥剤 |
US5536891A (en) | 1994-06-07 | 1996-07-16 | Vulcan Materials Company | Purification of 1,1,1,-trichloroethane |
US5910161A (en) | 1994-09-20 | 1999-06-08 | Fujita; Makoto | Refrigerating apparatus |
KR0159176B1 (ko) | 1995-04-12 | 1999-01-15 | 김은영 | 1,1-디플루오로에탄의 정제방법 |
US5742066A (en) | 1996-02-08 | 1998-04-21 | Bright Solutions, Inc. | Light source for use in leak detection in heating, ventilating, and air conditioning systems that utilize environmentally-safe materials |
JP3516322B2 (ja) | 1996-03-07 | 2004-04-05 | セントラル硝子株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの脱水方法 |
US5874657A (en) | 1996-11-01 | 1999-02-23 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,1-difluoroethane |
WO1998038264A1 (fr) | 1997-02-27 | 1998-09-03 | Daikin Industries, Ltd. | Refrigerateur et milieu hydraulique |
US6168720B1 (en) | 1997-06-20 | 2001-01-02 | Uop Llc | Process for drying CH2F2 refrigerant utilizing zeolite |
US6589444B2 (en) | 1997-11-10 | 2003-07-08 | Honeywell International Inc. | Process for separating water from chemical mixtures |
US6101818A (en) | 1997-11-10 | 2000-08-15 | Alliedsignal Inc. | Process for separating water from chemical mixtures |
JPH11293273A (ja) | 1998-04-15 | 1999-10-26 | Toshiba Corp | 冷凍サイクル用組成物、乾燥剤および冷媒圧縮機 |
JP2000039235A (ja) | 1998-07-22 | 2000-02-08 | Sharp Corp | 冷凍冷蔵庫の冷凍ユニット及び冷凍冷蔵庫の製造方法 |
JP3804289B2 (ja) | 1998-09-22 | 2006-08-02 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパン及び/又は1−クロロ−3,3,3−トリフルオロプロペンの製造方法 |
GB9920947D0 (en) | 1999-09-06 | 1999-11-10 | Ici Ltd | A method and apparatus for recovering a solvent |
US7084315B2 (en) * | 2000-05-04 | 2006-08-01 | Ineos Fluor Holdings Limited | Removal of (hydro)haloalkene impurities from product streams |
GB0010614D0 (en) | 2000-05-04 | 2000-06-21 | Ici Plc | Removal of (hydro)haloalkene impurities from product streams |
TWI288025B (en) | 2000-09-14 | 2007-10-11 | Showa Denko Kk | Adsorbent for purifying perfluorocarbon, process for producing same, high purity octafluoropropane and octafluorocyclobutane, and use thereof |
EP1351908B1 (en) | 2001-01-15 | 2005-07-20 | Showa Denko K.K. | Process for preparing octafluoropropane |
US7084316B2 (en) | 2002-07-02 | 2006-08-01 | Showa Denko K.K. | Process for purifying pentafluoroethane, process for producing the same, and use thereof |
US7230146B2 (en) | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
US20040089839A1 (en) | 2002-10-25 | 2004-05-13 | Honeywell International, Inc. | Fluorinated alkene refrigerant compositions |
EP2277942A3 (en) | 2002-10-25 | 2014-07-09 | Honeywell International, Incorporated. | Compositions containing fluorine substituted olefins |
US20080292564A1 (en) | 2002-10-25 | 2008-11-27 | Honeywell International, Inc. | Aerosol compositions containing fluorine substituted olefins and methods and systems using same |
AU2002357590A1 (en) | 2002-12-12 | 2004-06-30 | Hosei Co., Ltd. | Coffin device with cooling function |
GB0303972D0 (en) * | 2003-02-20 | 2003-03-26 | Ineos Fluor Holdings Ltd | Process |
JP2004339187A (ja) | 2003-03-18 | 2004-12-02 | Nippon Sanso Corp | パーフルオロ化合物の精製方法及び成膜方法 |
WO2005044765A2 (en) | 2003-11-10 | 2005-05-19 | Showa Denko K.K. | Purification method of, 1, 1-difluoroethane |
US7384519B2 (en) | 2003-12-23 | 2008-06-10 | Honeywell International Inc. | Process for the purification of pharmaceutical grade HFC-134a and polymer grade HCFC-22 |
WO2005067554A2 (en) | 2004-01-14 | 2005-07-28 | E.I. Dupont De Nemours And Company | Hydrofluorocarbon refrigerant compositions and uses thereof |
EP2292715B1 (en) | 2004-04-16 | 2012-08-22 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane |
US7629306B2 (en) | 2004-04-29 | 2009-12-08 | Honeywell International Inc. | Compositions comprising tetrafluoropropene and carbon dioxide |
TWI482748B (zh) | 2005-06-24 | 2015-05-01 | Honeywell Int Inc | 含有經氟取代之烯烴之組合物 |
PL1951838T3 (pl) | 2005-11-01 | 2013-12-31 | Du Pont | Kompozycje zawierające fluoroolefiny i ich zastosowania |
CN100537501C (zh) | 2006-04-14 | 2009-09-09 | 浙江蓝天环保高科技股份有限公司 | 1,1,1,3,3-五氟丙烷的提纯方法 |
GB0611742D0 (en) | 2006-06-14 | 2006-07-26 | Ineos Fluor Holdings Ltd | Desiccants for fluids |
US7597744B2 (en) * | 2006-07-12 | 2009-10-06 | Honeywell International Inc. | Use of molecular sieves for the removal of HFC-23 from fluorocarbon products |
CN101012146B (zh) | 2007-02-12 | 2012-07-25 | 四川省乐山市福华通达农药科技有限公司 | 由氯甲烷混合气体分离回收氯甲烷的方法 |
US9035111B2 (en) * | 2007-08-22 | 2015-05-19 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
GB0801209D0 (en) * | 2008-01-23 | 2008-02-27 | Ineos Fluor Holdings Ltd | Process |
FR2933402B1 (fr) * | 2008-07-03 | 2010-07-30 | Arkema France | Procede de purification de 2,3,3,3-tetrafluoro-1-propene (hfo1234yf) |
JP2010083818A (ja) * | 2008-09-30 | 2010-04-15 | Central Glass Co Ltd | 1,3,3,3−テトラフルオロプロペンの脱水方法 |
US8871112B2 (en) | 2008-11-19 | 2014-10-28 | E I Du Pont De Nemours And Company | Compositions comprising 2,3,3,3-tetrafluoropropene and hydrocarbons and uses thereof |
GB0918069D0 (en) * | 2009-10-15 | 2009-12-02 | Ineos Fluor Holdings Ltd | Process |
CN102101823B (zh) | 2009-12-16 | 2013-08-28 | 中化蓝天集团有限公司 | 一种1,1-二氟乙烷的气相提纯方法 |
CN102101822B (zh) | 2009-12-16 | 2013-08-28 | 中化蓝天集团有限公司 | 一种1,1-二氟乙烷的液相提纯方法 |
ES2545411T5 (es) | 2010-06-07 | 2024-04-05 | Amgen Inc | Dispositivo de administración de fármaco |
FR2973717B1 (fr) * | 2011-04-08 | 2013-03-29 | Ceca Sa | Procede de reduction de l'acidite totale de compositions frigorigenes |
US8337595B2 (en) * | 2011-04-20 | 2012-12-25 | Honeywell International Inc. | Purification of trans-1,3,3,3-tetrafluoropropene |
WO2013168178A1 (en) | 2012-03-30 | 2013-11-14 | Krishnan Archana Rajesh | Process for renaturation of polypeptides |
JPWO2013151070A1 (ja) | 2012-04-03 | 2015-12-17 | 旭硝子株式会社 | フルオロオレフィンの精製方法、およびフルオロオレフィンの製造方法 |
JP6107466B2 (ja) * | 2012-06-28 | 2017-04-05 | セントラル硝子株式会社 | トランス−1,3,3,3−テトラフルオロプロペンの精製方法 |
US8859829B2 (en) * | 2013-03-14 | 2014-10-14 | Honeywell International Inc. | Stabilizer and inhibitor for chloropropenes, such as tetrachloropropene 1,1,2,3-tetrachloropropene (1230xa), used in the manufacture of 2,3,3,3-tetrafluoropropene (1234yf) |
GB201307327D0 (en) * | 2013-04-23 | 2013-05-29 | Mexichem Amanco Holding Sa | Process |
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US20170100691A1 (en) | 2017-04-13 |
GB201410174D0 (en) | 2014-07-23 |
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US10456730B2 (en) | 2019-10-29 |
PL3151946T3 (pl) | 2022-11-14 |
AU2015273269A8 (en) | 2016-12-15 |
MX2022009519A (es) | 2022-09-09 |
KR20170002559A (ko) | 2017-01-06 |
EP3151946A1 (en) | 2017-04-12 |
BR112016028277A2 (pt) | 2017-08-22 |
US20200038800A1 (en) | 2020-02-06 |
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JP2017524660A (ja) | 2017-08-31 |
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CA2950389C (en) | 2019-11-12 |
CA2950389A1 (en) | 2015-12-17 |
WO2015189585A1 (en) | 2015-12-17 |
CN106536464A (zh) | 2017-03-22 |
BR112016028277B1 (pt) | 2022-12-13 |
CN106536464B (zh) | 2023-06-30 |
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