ES2617050T3 - Proceso para la purificación de (hidro)fluoroalquenos - Google Patents
Proceso para la purificación de (hidro)fluoroalquenos Download PDFInfo
- Publication number
- ES2617050T3 ES2617050T3 ES15173448.0T ES15173448T ES2617050T3 ES 2617050 T3 ES2617050 T3 ES 2617050T3 ES 15173448 T ES15173448 T ES 15173448T ES 2617050 T3 ES2617050 T3 ES 2617050T3
- Authority
- ES
- Spain
- Prior art keywords
- hydro
- r1243zf
- fluoroalkenes
- purification
- activated carbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract description 4
- 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 abstract 6
- 238000000746 purification Methods 0.000 title 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 14
- 239000003463 adsorbent Substances 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Un proceso para la retirada de uno o más compuestos de (hidro)fluoroalquino no deseados de un (hidro)fluoroalqueno, comprendiendo el proceso poner en contacto una composición que comprende el (hidro)fluoroalqueno y uno o más compuestos de (hidro)fluoroalquino no deseados con un adsorbente que contiene aluminio, un carbón activado o una mezcla de los mismos, en donde el (hidro)fluoroalqueno no contiene un resto >=CF2.
Description
5
10
15
20
25
30
35
40
- Carbón impregnado ST1x
- 46 9 100 31
- Carbón 207EA y KOH y KI al 10 %
- 13 5 70 8
- Alúmina de eta
- 7 7 18 16
Todos los adsorbentes explorados mostraron utilidad en la retirada de uno o ambos de R1225zc y TFMA de R1243zf. Sin embargo, los adsorbentes más efectivos eran los dopados con base, tanto de hidróxido como de carbonato de potasio, incluyendo el carbón ST1x.
Ejemplo de referencia 2
Una muestra de R1243zf disponible en el mercado (este puede obtenerse de Apollo Scientific, por ejemplo) se obtuvo y se analizó mediante GCMS capilar. Se encontró que este R1243zf contiene, entre otras, las siguientes impurezas:
- Impureza
- PPM p/p Punto de ebullición en °C
- R134a
- 2,5 26,074
- R1225zc
- 7,4 25,82
- R1234yf
- 26 29,69
- R134
- 87 23,15
- ZR1225ye
- 0,8 19,3
- R152a
- 251 24,023
- R40
- 0,9 24,15
- R31
- 11 9,15
- R133a
- 2,3 +7,51
R1225zc, El R31 y el R133a son compuestos tóxicos y se consideró deseable retirarlos del R1243zf antes de su uso, por ejemplo, como refrigerante. Incluso en el caso de que las diferencias del punto de ebullición hagan que la separación de algunos de estos componentes de R1243zf sea factible mediante destilación, los niveles bajos significan que dicho proceso consumiría mucha energía y sería ineficiente. Por lo tanto, se buscó un medio alternativo de retirar estas impurezas, particularmente el R1225zc, R31 y R133a, de 1243zf. Para este fin, se realizaron varios experimentos en los que se probó la eficacia de un intervalo de materiales adsorbentes para la retirada de los tres compuestos diana R31 y R133a de R 1243zf.
El intervalo de adsorbentes explorados comprendieron:
alúmina de eta (de BASF): una forma ácida de alúmina activada carbón activado de Chemviron 207c derivado de cáscaras de coco carbón activado de Chemviron 209M carbón activado de Chemviron 207EA ST1x de Chemviron: un carbón activado que comprende 207EA impregnado con diversas especies que incluyen una base o bases carbón activado de Chemviron 209m tamiz molecular 13X: un aluminosilicato o una zeolita AW500: un aluminosilicato estable ácido o una zeolita alúmina AL0104 (de BASF): una forma básica de alúmina
Los adsorbentes basados en carbono se preactivaron a 200 °C en flujo de nitrógeno durante 16 horas antes de su uso y los adsorbentes inorgánicos se activaron a 300 °C en flujo de nitrógeno de nuevo durante 16 horas. La eficacia de cada uno de los adsorbentes se sometió después a ensayo mediante el tratamiento de aproximadamente 100 g de R1243zf con entre 2 y 4 g de cada adsorbente en un sistema recirculatorio mediante el que el R1243zf se bombeó continuamente a través del lecho de adsorbente durante 16 horas a temperatura ambiente. Después del período de tratamiento, una muestra pequeña del R1243zf se tomó para análisis mediante GCMS capilar. El análisis del R1243zf tratado se comparó con el R1243zf sin tratar (véase la tabla anterior para las cantidades de impurezas) en la siguiente tabla.
7
11
Claims (1)
-
imagen1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0918069.6A GB0918069D0 (en) | 2009-10-15 | 2009-10-15 | Process |
| GB0918069 | 2009-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2617050T3 true ES2617050T3 (es) | 2017-06-15 |
Family
ID=41462387
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15173457T Active ES2701258T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
| ES15173448.0T Active ES2617050T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
| ES10774248T Active ES2784741T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
| ES16205166.8T Active ES2675739T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15173457T Active ES2701258T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10774248T Active ES2784741T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
| ES16205166.8T Active ES2675739T3 (es) | 2009-10-15 | 2010-10-08 | Proceso para la purificación de (hidro)fluoroalquenos |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US9012703B2 (es) |
| EP (5) | EP2952499B1 (es) |
| JP (4) | JP6067375B2 (es) |
| KR (4) | KR101721598B1 (es) |
| CN (3) | CN104370688B (es) |
| AU (1) | AU2010308156C1 (es) |
| BR (1) | BR112012008855B1 (es) |
| CA (1) | CA2776356A1 (es) |
| ES (4) | ES2701258T3 (es) |
| GB (1) | GB0918069D0 (es) |
| IN (1) | IN2012DN03033A (es) |
| MX (3) | MX2012004110A (es) |
| RU (3) | RU2015101087A (es) |
| TR (2) | TR201818613T4 (es) |
| WO (1) | WO2011045559A1 (es) |
| ZA (1) | ZA201202453B (es) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0611742D0 (en) | 2006-06-14 | 2006-07-26 | Ineos Fluor Holdings Ltd | Desiccants for fluids |
| GB0918069D0 (en) * | 2009-10-15 | 2009-12-02 | Ineos Fluor Holdings Ltd | Process |
| CA3220110A1 (en) | 2009-12-22 | 2011-07-21 | The Chemours Company Fc, Llc | Compositions comprising 2,3,3,3-tetrafluoropropene, 1,1,2,3-tetrachloropropene, 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1,2-tetrafluoropropane |
| GB2492847A (en) * | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| JP5899974B2 (ja) * | 2012-02-02 | 2016-04-06 | セントラル硝子株式会社 | （ｅ）−１−クロロ−３，３，３−トリフルオロプロペンの製造方法 |
| 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 |
| EP2867193B1 (en) * | 2012-06-06 | 2018-01-10 | The Chemours Company FC, LLC | Process for the reduction of rfccx impurities in fluoroolefins |
| 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 |
| ES2940562T3 (es) | 2013-03-13 | 2023-05-09 | Arkema Inc | Métodos para purificar y estabilizar hidrofluoroolefinas e hidroclorofluoroolefinas |
| US9334206B2 (en) | 2013-03-15 | 2016-05-10 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| EP2970058B1 (en) * | 2013-03-15 | 2023-12-13 | Honeywell International Inc. | Method for the removal of halogenated ethylene impuritites form a fluoroolefin mixture |
| US20150259267A1 (en) | 2014-03-14 | 2015-09-17 | E.I. Du Pont De Nemours And Company | PROCESS FOR THE REDUCTION OF RfC=CX IMPURITIES IN FLUOROOLEFINS |
| KR20150132289A (ko) * | 2013-03-15 | 2015-11-25 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 플루오로올레핀 중 알킨 불순물의 감소 방법 |
| US10995047B2 (en) | 2013-03-15 | 2021-05-04 | The Chemours Company Fc, Llc | Process for the reduction of RƒC≡CX impurities in fluoroolefins |
| GB201410174D0 (en) * | 2014-06-09 | 2014-07-23 | Mexichem Amanco Holding Sa | Process |
| FR3023286B1 (fr) * | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
| EP3187478B1 (en) * | 2014-08-25 | 2020-03-04 | AGC Inc. | Method for producing hydrofluoroolefin |
| DK3284797T3 (da) * | 2014-09-25 | 2021-02-01 | Daikin Ind Ltd | Sammensætning, der omfatter hfc og hfo |
| JP6028825B2 (ja) * | 2015-03-31 | 2016-11-24 | ダイキン工業株式会社 | ハイドロフルオロオレフィン化合物を含有する組成物 |
| WO2017029868A1 (ja) * | 2015-08-17 | 2017-02-23 | ダイキン工業株式会社 | ハロゲン化不飽和炭素化合物の分離方法 |
| US9938213B2 (en) * | 2015-08-19 | 2018-04-10 | Honeywell International Inc. | Methods for removing acidic impurities from halogenated propenes |
| US10005705B2 (en) | 2015-11-12 | 2018-06-26 | Honeywell International Inc. | Process for the production of fluorinated cyclobutane |
| JP6979066B2 (ja) * | 2016-11-02 | 2021-12-08 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 精製した２，３，３，３−テトラフルオロプロペン（ＨＦＯ−１２３４ｙｆ）を製造する方法 |
| WO2018092780A1 (ja) * | 2016-11-15 | 2018-05-24 | 旭硝子株式会社 | １－クロロ－２，３，３－トリフルオロプロペンの製造方法 |
| JP6323540B1 (ja) * | 2016-11-28 | 2018-05-16 | セントラル硝子株式会社 | ドライエッチング剤組成物及びドライエッチング方法 |
| GB201701099D0 (en) | 2017-01-23 | 2017-03-08 | Mexichem Fluor Sa De Cv | Process |
| EP4212500A1 (en) | 2018-06-06 | 2023-07-19 | Honeywell International Inc. | Method for dehydrochlorination of hcfc-244bb to manufacture hfo-1234yf |
| CN119954600A (zh) | 2018-08-24 | 2025-05-09 | 霍尼韦尔国际公司 | 用于产生三氟碘甲烷和三氟乙酰碘的方法 |
| US10941091B2 (en) * | 2018-12-03 | 2021-03-09 | Honeywell International Inc. | Processes for producing high-purity trifluoroiodomethane |
| EP3898878A4 (en) | 2018-12-21 | 2022-08-24 | Honeywell International Inc. | Azeotrope or azeotrope-like compositions of 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) and applications thereof |
| US11554956B2 (en) | 2019-04-16 | 2023-01-17 | Honeywell International Inc. | Integrated process and catalysts for manufacturing hydrogen iodide from hydrogen and iodine |
| WO2020225911A1 (ja) * | 2019-05-09 | 2020-11-12 | 日新電機株式会社 | 絶縁ガス用吸着剤及びガス絶縁電力機器 |
| JP7541693B2 (ja) * | 2019-08-20 | 2024-08-29 | 国立研究開発法人産業技術総合研究所 | 水試料中のペル及びポリフルオロアルキル化合物吸着活性炭 |
| EP4019124A4 (en) * | 2019-08-20 | 2023-10-04 | Futamura Kagaku Kabushiki Kaisha | PER- AND POLYFLUORALKYL COMPOUND ADSORBING ACTIVE CARBON |
| US12358796B2 (en) * | 2019-08-30 | 2025-07-15 | Resonac Corporation | Method for producing fluorine gas |
| CN114375287B (zh) * | 2019-09-12 | 2024-07-30 | 关东电化工业株式会社 | 具有＝cf2或＝chf的结构的氟烯烃的精制方法、以及高纯度氟烯烃及其制造方法 |
| JP7576789B2 (ja) * | 2020-09-30 | 2024-11-01 | 国立研究開発法人産業技術総合研究所 | 中性ペル及びポリフルオロアルキル化合物吸着活性炭及び水試料中の中性ペル及びポリフルオロアルキル化合物の分析方法 |
| KR20230075474A (ko) * | 2020-10-02 | 2023-05-31 | 솔베이(소시에떼아노님) | 기상의 플루오르화 올레핀을 정화하기 위한 프로세스 |
| WO2025174928A1 (en) * | 2024-02-16 | 2025-08-21 | The Chemours Company Fc, Llc | Purification of 2,3,3,3-tetrafluoropropene |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1540446A (en) | 1920-01-28 | 1925-06-02 | Baltimore Gas Engineering Corp | Aluminum gellike absorbent and process for making same |
| US2917556A (en) * | 1958-06-09 | 1959-12-15 | Du Pont | Process for separating vinylidene fluoride from vinyl fluoride |
| GB1052555A (es) * | 1963-05-31 | |||
| JPS6440507A (en) | 1987-08-06 | 1989-02-10 | Asahi Chemical Ind | Production of fluorine-containing polymer |
| JP2542394B2 (ja) * | 1987-08-06 | 1996-10-09 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | ヘキサフロロプロピレンの精製方法 |
| JPH07508215A (ja) * | 1992-06-19 | 1995-09-14 | カルゴン カーボン コーポレーション | 水酸化カリウムおよび／または水酸化ナトリウムまたはその塩で亜炭を処理することによる活性炭およびそれによる吸着 |
| US5462908A (en) | 1993-06-16 | 1995-10-31 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence | Organic amine impregnated activated carbon |
| EP0907402B1 (de) * | 1996-06-26 | 2001-05-23 | Cs Clean Systems Ag | Verfahren zur entfernung ozonabbauender und/oder klimawirksamer fluorierter verbindungen aus einem gasstrom sowie anwendung des verfahrens |
| US5705719A (en) | 1996-08-01 | 1998-01-06 | E. I. Du Pont De Nemours And Company | Selective removal of perfluoroisobutylene from streams of halogenated hydrocarbons |
| US6274782B1 (en) | 1997-04-16 | 2001-08-14 | Showa Denko K.K. | Method for purifying hexafluoroethane |
| 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 |
| JP2002154996A (ja) | 2000-11-17 | 2002-05-28 | Asahi Glass Co Ltd | 含フッ素不飽和化合物、その製法およびその使用 |
| US6544319B1 (en) | 2002-01-16 | 2003-04-08 | Air Products And Chemicals, Inc. | Purification of hexafluoro-1,3-butadiene |
| JP2003335712A (ja) | 2002-05-21 | 2003-11-28 | Tosoh F-Tech Inc | 含フッ素有機基を有するオレフィン化合物の精製方法 |
| WO2005044765A2 (en) * | 2003-11-10 | 2005-05-19 | Showa Denko K.K. | Purification method of, 1, 1-difluoroethane |
| US7897823B2 (en) | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
| JP2006156539A (ja) * | 2004-11-26 | 2006-06-15 | National Institute Of Advanced Industrial & Technology | プラズマ反応用ガス |
| RU2399607C2 (ru) | 2006-04-03 | 2010-09-20 | Е.И.Дюпон Де Немур Энд Компани | Селективно взаимодействующие олефины, содержащие концевую группу cf2, в смеси |
| JP4693811B2 (ja) * | 2006-06-13 | 2011-06-01 | セントラル硝子株式会社 | １，３，３，３−テトラフルオロプロペンの製造方法 |
| GB0611742D0 (en) | 2006-06-14 | 2006-07-26 | Ineos Fluor Holdings Ltd | Desiccants for fluids |
| CN101479220A (zh) * | 2006-06-30 | 2009-07-08 | 昭和电工株式会社 | 高纯度六氟丙烯的制造方法及清洗气 |
| US7597744B2 (en) | 2006-07-12 | 2009-10-06 | Honeywell International Inc. | Use of molecular sieves for the removal of HFC-23 from fluorocarbon products |
| US20080110883A1 (en) | 2006-11-13 | 2008-05-15 | Vetter Douglas J | Trash can cleaning lid |
| US20080110833A1 (en) * | 2006-11-14 | 2008-05-15 | Samuels George J | Iodine removal with activated carbon |
| US20100185029A1 (en) * | 2007-06-27 | 2010-07-22 | Arkema Inc. | Two step process for the manufacture of hydrofluoroolefins |
| US20110009678A1 (en) * | 2007-09-13 | 2011-01-13 | Arkema Inc. | Compositions containing a combination of z and e stereoisomers of hydrofluoroolefins |
| FR2933402B1 (fr) | 2008-07-03 | 2010-07-30 | Arkema France | Procede de purification de 2,3,3,3-tetrafluoro-1-propene (hfo1234yf) |
| JP5187212B2 (ja) * | 2009-02-03 | 2013-04-24 | セントラル硝子株式会社 | １，３，３，３−テトラフルオロプロペンの製造方法 |
| GB0918069D0 (en) * | 2009-10-15 | 2009-12-02 | Ineos Fluor Holdings Ltd | Process |
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