WO2008008695A1 - Use of molecular sieves for the removal of hfc-23 from fluorocarbon products - Google Patents

Use of molecular sieves for the removal of hfc-23 from fluorocarbon products Download PDF

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Publication number
WO2008008695A1
WO2008008695A1 PCT/US2007/072896 US2007072896W WO2008008695A1 WO 2008008695 A1 WO2008008695 A1 WO 2008008695A1 US 2007072896 W US2007072896 W US 2007072896W WO 2008008695 A1 WO2008008695 A1 WO 2008008695A1
Authority
WO
WIPO (PCT)
Prior art keywords
mixture
trifluoroiodomethane
trifluoromethane
hfc
process according
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.)
Ceased
Application number
PCT/US2007/072896
Other languages
English (en)
French (fr)
Inventor
Raymond H. Thomas
Rajiv R. Singh
Thomas W. Morris
Roy P. Robinson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Priority to JP2009519602A priority Critical patent/JP2009543793A/ja
Priority to EP18174105.9A priority patent/EP3415220A1/en
Priority to EP07799343A priority patent/EP2038043A1/en
Publication of WO2008008695A1 publication Critical patent/WO2008008695A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/10—Inorganic adsorbents
    • B01D2253/106—Silica or silicates
    • B01D2253/108—Zeolites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/20—Halogens or halogen compounds
    • B01D2257/206—Organic halogen compounds
    • B01D2257/2066—Fluorine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/20—Halogens or halogen compounds
    • B01D2257/206—Organic halogen compounds
    • B01D2257/2068—Iodine
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/30—Capture or disposal of greenhouse gases of perfluorocarbons [PFC], hydrofluorocarbons [HFC] or sulfur hexafluoride [SF6]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2
    • Y02P20/155—Perfluorocarbons [PFC]; Hydrofluorocarbons [HFC]; Hydrochlorofluorocarbons [HCFC]; Chlorofluorocarbons [CFC]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S95/00—Gas separation: processes
    • Y10S95/90—Solid sorbent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S95/00—Gas separation: processes
    • Y10S95/90—Solid sorbent
    • Y10S95/902—Molecular sieve
    • Y10S95/903—Carbon

Definitions

  • This invention relates to the use of molecular sieves to separate trifluoromethane (HFC-23) from a mixture of HFC-23 with other gases, particularly from mixtures containing HFC-23 and trifluoroiodomethane (CF3I).
  • HFC-23 trifluoromethane
  • CF3I trifluoroiodomethane
  • HFC's chlorofluorocarbons
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbon compounds
  • PFCs perfluorocarbon compounds
  • HFC's hydrofluorocarbon compounds
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbon compounds
  • GWP global warming potential
  • CF3I trifluoroiodomethane
  • a lubricant Any of a variety of conventional lubricants may be used.
  • An important requirement for the lubricant is that, when in use in a refrigerant system, there must be sufficient lubricant returning to the compressor of the system such that the compressor is lubricated.
  • suitability of a lubricant for any given system is determined partly by the refrigerant/lubricant characteristics and partly by the characteristics of the system in which it is intended to be used.
  • Suitable lubricants include mineral oil, alkyl benzenes, polyol esters, including polyalkylene glycols, PAG oil, and the like.
  • these lubricants which are hydrogen bearing for the most part, by interaction with trifluoroiodomethane results in the production of highly undesirable trifluoromethane (HFC-23) which has a high GWP.
  • HFC-23 highly undesirable trifluoromethane
  • This HFC-23 breakdown product is very undesirable in a product or composition that is intended to have and should have a low GWP.
  • molecular sieves of an acceptable effective pore size provides a process for trapping or separating HFC-23 from its mixture with materials, such as fluids or gases, particularly iodocarbons, whose molecular diameters are greater than that of HFC- 23 so as to reduce the amount of HFC-23 in the mixture.
  • the process may be conducted with any suitable molecular sieve and is suitable for separating HFC-23 from its mixture with any other material that has a molecular diameter, polarity or shape such that a separation is possible.
  • the process of this invention is particularly suitable for removing HFC-23 from refrigerant compositions, especially refrigerant compositions containing iodocarbons, such as trifluoroiodomethane.
  • the process of the invention is particularly suitable for removing HFC-23 produced in-situ by interaction between the components of a refrigerant composition containing an iodocarbon, such as trifluoroiodomethane, and a lubricant.
  • a process for trapping or separating at least a portion of HFC-23 from its mixture with other materials, such as fluids or gases, particularly iodocarbons so as to reduce the amount of HFC-23 in the mixture While it is difficult to predict molecular sieve separations, the inventors have shown that iodocarbons, particularly trifluoroiodomethane are such that they can be separated from fluorocarbons such as R-23 by the use of molecular sieves whose diameters are about 5 angstroms.
  • the process may be conducted with any suitable molecular sieve and is suitable for separating HFC-23 from its mixture with any other fluid or gas that has a molecular diameter greater than the molecular diameter of HFC-23.
  • the process of this invention is particularly suitable for removing HFC-23 from refrigerant compositions, especially refrigerant compositions containing iodocarbons, such as trifluoroiodomethane.
  • the process of the invention is particularly suitable for removing HFC-23 produced in-situ by interaction between the components of a refrigerant composition containing an iodocarbon, such as trifluoroiodomethane, and optionally a lubricant.
  • an "iodocarbon” is any compound containing iodine and carbon atoms and optionally other atoms.
  • the product containing the HFC-23 as an impurity in a composition with other desirable materials, such as fluid(s) or gas(es), can be brought into contact with the molecular sieve in either the liquid or gas phase, in a process that may be either a continuous or a batch process to adsorb the HFC-23 and thereby separate and remove it from the other desirable fluid(s) or gas(es).
  • the level to which the HFC-23 is reduced is dependent upon the capacity of the molecular sieve and the equilibrium between the HFC-23 and the mixture of gases and in the molecular sieve itself.
  • the process of this invention may employ any suitable molecular sieve including, but not limited to, suitable zeolite and carbon molecular sieves.
  • the suitable molecular sieve must have an acceptable effective pore size such as to adsorb HFC-23 but not adsorb the other favorable and desired fluids or gases. It has been discovered that 4A molecular sieves (having an effective pore size of 4A) will not separate HFC-23 from trifluroiodomethane, however 5A series molecular sieves (with an effective pore size of 5A) will very effectively achieve such separation of HFC-23 from trifluroiodomethane.
  • HFC-23 has an effective molecular diameter of less than 5A and that the effective molecular diameter of trifluoroiodomethane is greater than 5A.
  • separation of HFC-23 from trifluoroiodomethane can be effected by using molecular sieves whose diameters are less than the effective molecular diameter of trifluoroiodomethane.
  • HFC-23 can be adsorbed and separated from a composition containing HFC-23 and another fluid or gas having a greater molecular diameter than the HFC-23.
  • the other fluid or gas is one having an effective molecular diameter of 1 ⁇ A
  • molecular sieves having an effective pore size of from 5A to 9A may be employed to effect the adsorption and separation of HFC- 23 from the composition.
  • molecular sieves of an "effective pore size" are those molecular sieves that operate to preferentially reduce the amount of, or remove at least some of, HFC-23.
  • Such molecular sieves having an effective pore size are generally those having an effective pore size of from 5A to a pore size less than the effective molecular diameter of the other fluid(s) or gas(es).
  • Molecular sieves useful in the process of this invention are available from a variety of sources, including but not limited to, zeolite molecular sieves from Universal oil Products, Grace and Aldrich Chemical Co., and carbon molecular sieves from Aldrich Chemical Co., Chemos GmbH of Germany and Dayung Chemical Co., Ltd. of China.
  • AW500 zeolite molecular sieve (Aldrich chemical Co.) having an effective pore size of 5A was placed in an oven at 300 0 F (149 0 C) for four hours to activate the molecular sieve.
  • This activated molecular sieve was employed in the following Examples 1 , 2 and 4.
  • the molecular sieves employed in Example 3 and Comparative Examples 1 and 2 were activated in a similar manner.
  • Example 2 2.26 Grams of activated AW500 molecular sieve were placed into a stainless steel cylinder. 2.04 Grams of the refrigerant mixture trifluoroiodomethane/HFO-1234yf (1 ,1,1 ,2-tetrafluoropropene) (25/75) were added to the cylinder. The refrigerant mixture contained 4.1 wt. % HFC-23. After one hour the gas in the cylinder was examined and found to contain only 0.15 wt % HFC-23 because of the adsorption of the HFC-23 by the molecular sieve.
  • Example 4 2.5 Grams of activated AW500 molecular sieve were placed into a stainless steel cylinder. 2.5 Grams of the refrigerant mixture trifluoroiodomethane/HFO-1234 (tetrafluoropropene) (25/75) were added to the cylinder. The refrigerant mixture contained 0.5 wt. % HFC-23. After one hour the gas in the cylinder was examined and found to contain only 0.003 wt % HFC-23 because of the adsorption of the HFC-23 by the molecular sieve. [0018] Comparative Example 1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Separation Of Gases By Adsorption (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
PCT/US2007/072896 2006-07-12 2007-07-06 Use of molecular sieves for the removal of hfc-23 from fluorocarbon products Ceased WO2008008695A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2009519602A JP2009543793A (ja) 2006-07-12 2007-07-06 フルオロカーボン製品からｈｆｃ−２３を除去するためのモレキュラーシーブの使用
EP18174105.9A EP3415220A1 (en) 2006-07-12 2007-07-06 Use of molecular sieves for the removal of hfc-23 from fluorocarbon products
EP07799343A EP2038043A1 (en) 2006-07-12 2007-07-06 Use of molecular sieves for the removal of hfc-23 from fluorocarbon products

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/485,519 US7597744B2 (en) 2006-07-12 2006-07-12 Use of molecular sieves for the removal of HFC-23 from fluorocarbon products
US11/485,519 2006-07-12

Publications (1)

Publication Number Publication Date
WO2008008695A1 true WO2008008695A1 (en) 2008-01-17

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PCT/US2007/072896 Ceased WO2008008695A1 (en) 2006-07-12 2007-07-06 Use of molecular sieves for the removal of hfc-23 from fluorocarbon products

Country Status (4)

Country Link
US (1) US7597744B2 (https=)
EP (2) EP2038043A1 (https=)
JP (1) JP2009543793A (https=)
WO (1) WO2008008695A1 (https=)

Cited By (2)

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Publication number Priority date Publication date Assignee Title
JP2013508265A (ja) * 2009-10-15 2013-03-07 メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ （ヒドロ）フルオロアルケン類を精製する方法
WO2015189585A1 (en) * 2014-06-09 2015-12-17 Mexichem Amanco Holding S.A. De C.V. Process for purifying (hydro)fluoropropenes contaminated with halogenated ethane

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GB0611742D0 (en) 2006-06-14 2006-07-26 Ineos Fluor Holdings Ltd Desiccants for fluids
KR102884920B1 (ko) * 2008-05-07 2025-11-12 더 케무어스 컴퍼니 에프씨, 엘엘씨 1,1,1,2,3-펜타플루오로프로판 또는 2,3,3,3-테트라플루오로프로펜을 포함하는 조성물
CN104164214B (zh) * 2008-05-07 2018-04-24 科慕埃弗西有限公司 可用作热传递组合物的组合物
US8337595B2 (en) * 2011-04-20 2012-12-25 Honeywell International Inc. Purification of trans-1,3,3,3-tetrafluoropropene
US20130210946A1 (en) * 2012-02-10 2013-08-15 Honeywell International Inc. Blowing agents, foam premixes and foams containing halogenated olefin blowing agent and adsorbent
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
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
US10995047B2 (en) 2013-03-15 2021-05-04 The Chemours Company Fc, Llc Process for the reduction of RƒC≡CX impurities in fluoroolefins
GB201307327D0 (en) 2013-04-23 2013-05-29 Mexichem Amanco Holding Sa Process
US20150082981A1 (en) * 2013-09-20 2015-03-26 E I Du Pont De Nemours And Company Capture of trifluoromethane using ionic liquids
JP2016147815A (ja) * 2015-02-10 2016-08-18 宇部興産株式会社 フルオロヨードアルカンの吸着処理方法
CN107743479A (zh) 2015-04-24 2018-02-27 霍尼韦尔国际公司 降低244bb中的1233xf浓度的方法
CN108675914A (zh) * 2018-06-19 2018-10-19 宇极（廊坊）新材料有限公司 一种制备高纯三氟碘甲烷的方法
US10941091B2 (en) * 2018-12-03 2021-03-09 Honeywell International Inc. Processes for producing high-purity trifluoroiodomethane
US11326998B2 (en) 2019-04-19 2022-05-10 Kidde Technologies, Inc. System and method for monitoring a fire suppression blend
US10953257B2 (en) 2019-04-19 2021-03-23 Kidde Technologies, Inc. Fire suppression composition
US11291876B2 (en) 2019-04-19 2022-04-05 Kidde Technologies, Inc. Fire suppression agent composition
JP7582615B2 (ja) * 2020-02-14 2024-11-13 国立研究開発法人産業技術総合研究所 ペル及びポリフルオロアルキル化合物捕集個人曝露測定用サンプラー
TWI859415B (zh) * 2020-02-14 2024-10-21 國立研究開發法人產業技術總合研究所 用於收集全氟及多氟烷基化合物之個人暴露測量用採樣器
EP4674832A1 (en) * 2023-02-28 2026-01-07 Agc Inc. Method for purifying vinylidene fluoride
WO2025258262A1 (ja) * 2024-06-12 2025-12-18 Ａｇｃ株式会社 フッ化ビニリデンの精製方法

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Cited By (9)

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Publication number Priority date Publication date Assignee Title
JP2013508265A (ja) * 2009-10-15 2013-03-07 メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ （ヒドロ）フルオロアルケン類を精製する方法
US9012703B2 (en) 2009-10-15 2015-04-21 Mexichem Amanco Holdings S.A. De C.V. Process for purifying (hydro) fluoroalkenes
US9309176B2 (en) 2009-10-15 2016-04-12 Mexichem Amanco Holding S.A. De C.V. Process for purifying (hydro)fluoroalkenes
US9624148B2 (en) 2009-10-15 2017-04-18 Mexichem Amanco Holding S.A. De C.V. Process for purifying (hydro)fluoroalkenes
US9790152B2 (en) 2009-10-15 2017-10-17 Mexichem Amanco Holding S.A. De C.V. Process for purifying (hydro)fluoroalkenes
WO2015189585A1 (en) * 2014-06-09 2015-12-17 Mexichem Amanco Holding S.A. De C.V. Process for purifying (hydro)fluoropropenes contaminated with halogenated ethane
US10456730B2 (en) 2014-06-09 2019-10-29 Mexichem Fluor S.A. De C.V. Process for purifying (hydro) fluoropropenes contaminated with halogenated ethane
US11007471B2 (en) 2014-06-09 2021-05-18 Mexichem Fluor S.A. De C.V. Process for purifying (hydro)fluoropropenes contaminated with halogenated ethane
EP4074406A1 (en) * 2014-06-09 2022-10-19 Mexichem Fluor S.A. de C.V. Process for purifying tetrafluoropropenes contaminated with halogenated ethane

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EP3415220A1 (en) 2018-12-19
EP2038043A1 (en) 2009-03-25
US20080011159A1 (en) 2008-01-17
JP2009543793A (ja) 2009-12-10
US7597744B2 (en) 2009-10-06

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