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WO2018102250A1 - Procédé de séchage de hcfo-1233zd - Google Patents

Procédé de séchage de hcfo-1233zd Download PDF

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Publication number
WO2018102250A1
WO2018102250A1 PCT/US2017/063247 US2017063247W WO2018102250A1 WO 2018102250 A1 WO2018102250 A1 WO 2018102250A1 US 2017063247 W US2017063247 W US 2017063247W WO 2018102250 A1 WO2018102250 A1 WO 2018102250A1
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WO
WIPO (PCT)
Prior art keywords
chloro
trifluoropropene
water
azeotropic
azeotrope
Prior art date
Application number
PCT/US2017/063247
Other languages
English (en)
Inventor
Yuon Chiu
Stephen A. Cottrell
Hang T. Pham
Gustavo Cerri
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
Priority claimed from US15/368,027 external-priority patent/US9926244B2/en
Application filed by Honeywell International Inc. filed Critical Honeywell International Inc.
Priority to CN202310293598.7A priority Critical patent/CN116396143A/zh
Priority to MX2019006410A priority patent/MX2019006410A/es
Priority to EP17876338.9A priority patent/EP3548458A4/fr
Priority to KR1020197015714A priority patent/KR102652080B1/ko
Priority to CN201780074649.XA priority patent/CN110035988A/zh
Publication of WO2018102250A1 publication Critical patent/WO2018102250A1/fr

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    • 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
    • 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

Definitions

  • HCFO-1233zd l-chloro-3,3,3-trifluoropropene
  • the crude product from the process may require aqueous washing to remove i IF. HC1, and other acidic components.
  • the present disclosure pertains to azeotropic or azeotrope-like compositions of HFO-1233zd and water and processing such compositions.
  • HCFO-1233zd (1233zd) Commercial uses for HCFO-1233zd (1233zd) include foam blowing agent and solvent applications. In such applications, tight control of moisture content is typically needed to meet customer requirements. Occasionally, due to process issues, the moisture level in 1233zd may exceed specification limits.
  • the present disclosure provides separation processes that use azeotropic or azeotropic -like compositions of l-chloro-3,3,3-trifluoropropene (HCFO-1233zd) that allow for improved recovery rates of l-chloro-3,3,3-trifluoropropene during or after manufacturing processes.
  • Such recovery or separation processes can utilize the unique properties of azeotropic or azeotropic-like compositions with various combinations of separation techniques (e.g., distillation and decanting) that yield highly pure compositions of l-chloro-3,3,3-trifluoropropene and simultaneously offer high yields of l-chloro-3,3,3-trifluoropropene.
  • Such highly pure compositions of l-chloro-3,3,3-trifluoropropene may find useful applications in polymer technology as monomers or comonomers.
  • Methods for recovering l-chloro-3,3,3-trifluoropropene may include forming an azeotropic or azeotrope-like composition compri sing, consisting essentially of, or consisting of ! .-chloro-3,3,3-trifluoropropene and water, conveying the formed azeotropic or azeotrope-like composition into a separator, and recovering an organic layer comprising l -chloro-3,3,3- trifiuoropropene.
  • the composition may comprise as little as about 70 wt.% l -chloro-3,3,3-trifIuoropropene, 86 wt.% l-chloro-3,3,3-trifluoropropene, 90% wt.% 1- chloro-3,3,3-trifluoropropene, as great as 98.5 wt.% I -chloro-3,3,3-trifluoropropene, 99 wt.% 1- chloro-3,3,3-trifiuoropropene, 99.95 wt.
  • the compositions may have a boiling point of about 17.4°C ⁇ 1°C at a pressure of about 14.7 psia.
  • Various methods may also include additional steps, such as decanting off a water layer, returning the organic layer to a distillation column, and/or separating water in the organic layer from l-chloro-3,3,3-trifluoropropene with distillation.
  • some methods may result in a substantially pure 1-chloro- 3,3,3-trifiuoropropene, when removed from the distillation column, and may contain less than about 100 ppm of water by weight, contain less than about 50 ppm of water by weight, or contain less than about 40 ppm of water by weight.
  • the substantially pure l-chloro-3,3,3-trifluoropropene when removed from the distillation column, and may contain as little as about 10 ppm., 11 ppm, 15 ppm, or as great as 20 ppm., 25 ppm, 30 ppm, 40 ppm, 50 ppm, 100 ppm, or within any range defined between any two of the foregoing values (such as between 10 ppm and 40 pprn).
  • the azeotropic mixtures may have as little as about 70 wt.% l-chioro-3,3,3- trifluoropropene, 86 wt.% l-chloro-3,3,3-trifluoropropene, 90% wt.% l-chloro-3,3,3- trifluoropropene, as great as 98.5 wt.% l -chloro-3,3,3-trifluoropropene, 99 wt.% l-chloro-3,3,3- trifluoropropene, 99.95 wt.
  • % l-chioro-3,3,3-trifluoropropene or within any range defined between any two of the foregoing values (such as between 70 wt.% l-chloro-3,3,3- trifluoropropene and 99.95 wt. % l-chloro ⁇ 3,3,3-trifluoropropene) and as little as 0.05 wt.% water, 2.5 wt.% water, 10 wt.% water, or as great as 14 wt.% water, 20 wt.% water, 30 wt.
  • % water or w ithin any range defined between any two of the foregoing values (such as between 0.05wt.% water and 30 wt.% water) based on the combined weight of water and l-chloro-3,3,3- trifluoropropene.
  • the azeotropic mixtures may have a boiling point of about 17.4°C ⁇ 1°C at a pressure of about 14.7 psia.
  • compositions having l -chloro-3,3,3- trifluoropropene and water.
  • the compositions may consist of only water and 1 -chloro-3 ,3 ,3 -trifluoropropene .
  • compositions may have as little as about 70 wt.% l-chloro-3,3,3- trifluoropropene, 86 wt.% l-chloro-3,3,3-trifluoropropene, 90% wt.% l-chloro-3,3,3- trifluoropropene, as great as 98.5 wt.% l-chloro-3,3,3-trifluoropropene, 99 wt.% l-chloro-3,3,3- trifluoropropene, 99.95 wt.
  • the composition may have a boiling point of about 17.4°C ⁇ 1°C at a pressure of about 14.7 psia.
  • FIG. 1 is a process diagram for the recovery of l-chloro-3,3,3-trifluoropropene
  • FIG. 2 is a flow diagram of an exemplary method for recovering l -chloro-3,3,3- trifluoropropene .
  • this disclosure provides separation techniques that utilize azeotropic or azeotrope-like compositions of l-chloro-3,3,3-trifluoropropene (HCFC-1233zd) and water and methods of recovering l-chloro-3,3,3-trifluoropropene (HCFC-1233zd) from azeotropic or azeotrope-like compositions comprising l-chloro-3,3,3-trifluoropropene and water.
  • l-chloro-3,3,3-trifluoropropene forms azeotropic and azeotrope-like compositions or mixtures with water, and more particularly, forms heterogeneous azeotropic and azeotrope-like composition or mixtures with water.
  • l-chloro-3,3,3-trifluoropropene has a boiling point of about 19°C, has a vapor pressure of 1516 hPa at about 30°C, and has the following structure:
  • the modifier "about” used in connection with a quantity is inclusive of the stated value and has the meaning dictated by the context (for example, it includes at least the degree of error associated with the measurement of the particular quantity)-
  • the modifier "about” should also be considered as disclosing the range defined by the absolute values of the two endpoints. For example, the range “from about 2 to about 4" also discloses the range “from 2 to 4.”
  • U.S. Patent No. 8,921,621 describes a process for the production of l-chloro-3,3,3-trifluoropropene (HCFC-1233zd) on a commercial scale from the reaction of 1, 1,1,3,3-pentachloropropane (HCC-240fa) and HF.
  • HCC-240fa and HF are fed to a liquid phase reactor operating at high pressure.
  • the resulting product stream of 1233zd, HCl, HF, and other byproducts is partially condensed to recover HF by phase separation.
  • the recovered HF phase is recycled to the reactor.
  • the HCl is scmbbed from the vapor stream and recovered as an aqueous solution.
  • the remaining organic components including the desired HCFC-1233zd are scrubbed, dried and distilled to meet commercial product specifications.
  • FIG. 1 is a process diagram for the recovery of l-chloro-3,3,3-trifluoropropene from water.
  • wet and acid-free 1233zd (HCFO-1233zd) crude vapor from the caustic scrubber outlet are condensed in a condenser.
  • the condensed wet 1233zd will then flow (illustrated in FIG. I as flow stream 1 1) into a distillation pump tank or decanting tank 12, where the water will settle as the top layer (first aqueous layer 14) and the 1233zd will settle as bottom layer (first organic layer 16).
  • first removal stream 18 During commercial processing of 1233zd, it is expected that one should not need to attend to this water for up to 3 months at 1 ,500 Ibs/hr crude 1233zd production rate and when water is removed, it may be removed as first removal stream 18.
  • the removal of water as first removal stream 18 may be accomplished by decanting, selective pumping, or other liquid-liquid separating processes. A monitoring program to track this water volume, and its acidity content, e.g., to prevent any corrosion or overspill incident, has been developed.
  • the water is expected to contain about 2,000 ppm crude 1233zd, or about 0.03 lbs/hr organic.
  • the term " 'ppm" or "parts-per-million” shall be understood to be the mass fraction unless explicitly stated otherwise. This water can be recycled to the caustic scrubber for organic recovery and disposal.
  • first organic layer 16 may then be further processed, such as by distilling the first organic layer.
  • first organic layer 16 may flow through distillation inlet 22 to distillation column 20, where the l -chloro-3,3,3-trifluoropropene and water may be distilled, including being distilled until forming an azeotrope.
  • distillation column 20 can be understood to include any conventional fractionating column or fractionation column that uses distillation to separate a mixture into component parts or fractions based on differences in volatilities.
  • the first organic layer 16 may be distilled in distillation column, yielding a bottoms 24 of essentially pure I -chloro-3,3,3- trifluoropropene while overhead 26 may be condensed and sent either to the first separator 12 and/or to a second phase separator 30.
  • the top vapor fraction or overhead 26 may be an azeotropic or azeotrope-like composition of l -chloro-3,3,3- trifluoropropene and water.
  • 1,3,3 ,3-tetrafluoropropene may also be present and/or may also form an azeotrope with the water in the overhead of the distillation column.
  • other other organics and/or impurities in the composition which themselves form azeotropes with water may be used to ad vantageously further draw additional water from the contents of the distillation column 21 in addition to the water which is drawn into the principal azeotrope of 1 - chloro-3,3,3-trifluoropropene and water, further drying and purifying the 1233zd collected product.
  • both water-containing azeotropes of impurities and/or non- azeotropic compositions of impurities may be drawn away from 1233zd in the distillation column 20 to enhance the purity of the recovered 1233zd.
  • excess l-chloro-3,3,3-trifluoropropene may be present in azeotrope composition in the overhead, for example, due to tray inefficiencies or distillation column inefficiencies.
  • thermodynamic state of a fluid is defined by its pressure, temperature, liquid composition and vapor composition.
  • the liquid composition and vapor phase are essentially equal at a given temperature and pressure range. In practical terms this means that the components cannot be separated during a phase change.
  • an azeotrope is a liquid mixture that exhibits a maximum or minimum boiling point relative to the boiling points of surrounding mixture compositions.
  • azeotrope-like refers to compositions that are strictly azeotropic and/or that generally behave like azeotropic mixtures.
  • An azeotrope or an azeotrope-like composition is an admixture of two or more different components which, when in liquid form under a given pressure, will boil at a substantially constant temperature, which temperature may be higher or lower than the boiling temperatures of the individual components and which will provide a vapor composition essentially identical to the liquid composition undergoing boiling.
  • azeotropic compositions may be defined to include azeotrope-like compositions, which is a composition that behaves like an azeotrope, i.e., that has constant boiling characteristics or a tendency not to fractionate upon boiling or evaporation.
  • azeotrope-like compositions which is a composition that behaves like an azeotrope, i.e., that has constant boiling characteristics or a tendency not to fractionate upon boiling or evaporation.
  • the composition of the vapor formed during boiling or evaporation is the same as or substantially the same as the original liquid composition.
  • the liquid composition if it changes at ail, changes only to a minimal or negligible extent. This is in contrast with non-azeotrope-like compositions in which during boiling or evaporation, the liquid composition changes to a substantial degree.
  • the essential features of an azeotrope or an azeotrope-like composition are that at a given pressure, the boiling point of the liquid composition is fixed and that the composition of the vapor above the boiling composition is essentially that of the boiling liquid composition, i.e., essentially no fractionation of the components of the liquid composition takes place. Both the boiling point and the weight percentages of each component of the azeotropic composition may change when the azeotrope or azeotrope-like liquid composition is subjected to boiling at different pressures.
  • an azeotrope or an azeotrope-like composition may be defined in terms of the relationship that exists between its components or in terms of the compositional ranges of the components or in terms of exact weight percentages of each component of the composition characterized by a fixed boiling point at a specified pressure.
  • compositions which comprises effective amounts of l-chloro-3,3,3-trifluoropropene and water to form an azeotropic or azeotrope-like composition is pro vided.
  • effective amount is an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope-like mixture.
  • compositions preferably are binary azeotropes which comprise or consist essentially of combinations of l-chloro-3,3,3-trifluoropropene and water, or consist of combinations of l-chloro-3,3,3-trifluoropropene and water.
  • binary azeotropes which comprise or consist essentially of combinations of l-chloro-3,3,3-trifluoropropene and water, or consist of combinations of l-chloro-3,3,3-trifluoropropene and water.
  • the term '"consisting essentially of, with respect to the components of an azeotrope-like composition or mixture means the composition contains the indicated components in an azeotrope-like ratio, and may contain additional components provided that the additional components do not form new azeotrope-like systems.
  • azeotrope-like mixtures consisting essentially of two compounds are chose that form binary azeotropes, which optionally may include one or more additional components, provided that the additional components do not render the mixture non- azeotropic and do not fonn an azeotrope with either or both of the compounds (e.g., do not form a ternary azeotrope).
  • heteroazeotrope and ' “ heterogeneous azeotrope' 1 mean an azeotrope-like composition comprising a vapor phase existing concurrently with two liquid phases.
  • the present disclosure also encompasses generating an azeotropic or azeotrope-like composition of l-chloro-3,3,3-trifluoropropene and water followed by isolating the azeotrope from impurities.
  • the present disclosure also includes steps for separating and purifying 1- chloro-3,3,3-trifluoropropene from the azeotropic mixture, as discussed in greater detail below.
  • l-chloro-3,3,3-trifluoropropene may be produced using one or more methods that are known in the art, in which l-chloro-3,3,3-trifluoropropene is produced as a component of a reactant mixture containing one or more impurities.
  • essentially water-free or “water-free” refers to compositions of l-chloro-3,3,3-trifluoropropene which include less than 1.0 wt,% water.
  • compositions of l-ch1oro-3,3,3-trifluoropropene and water that have less than 0.4 wi.% water, or less than 0.1 wi.% water would be considered to be water-free.
  • Separation methods may include any method generally known in the art.
  • the excess water cars be removed from the I -chloro-3,3,3- trifluoropropene by liquid-liquid phase separation, though other alternatives include distillation or scrubbing.
  • the remaining water can then be removed from the l-chloro-3,3,3- trifluoropropene by distillation and/or the use of one or more drying media or desiccants such as molecular sieves, calcium sulfate, silica, alumina, and combinations thereof.
  • Exemplary methods can be used for recovering l-chioro-3, 3, 3 -trifluoropropene.
  • Recovery method 1 may include forming an azeotropic or azeotrope-like composition consisting essentially of l-chloro-3,3,3- trifluoropropene and water (step 2), conveying the formed azeotropic or azeotrope-like composition into a separator (step 3), and recovering an organic layer comprising l-chloro-3,3,3- trifluoropropene (step 4).
  • the overhead may be split, before or after condensing, into a light organics purge 25 and an overhead products stream 26, which may have an azeotropic composition of water and l-chloro-3,3,3-trifluoropropene, and may be condensed and sent to a second phase separator 30.
  • the light organics purge may be part of second phase separator 30.
  • Light organics purge may be used to remove light organics present in production systems and may include compounds such as 1,3,3,3- tetrafluoropropene (HFO-1234ze) isomers, 1 ,1, 1,3,3-pentafluoropropane (HFC ⁇ 245fa) and, in some cases, some HFO-1233zd.
  • HFO-1234ze 1,3,3,3- tetrafluoropropene
  • HFC ⁇ 245fa 1,3,3-pentafluoropropane
  • a second water phase 34 and a second organic layer 36 may form.
  • the second water phase 34 may be decanted off and discarded (illustrated second discard stream 38) or may be recycled (in whole or in part) to first phase separator 12 via recycle stream 32.
  • second organic layer 36 may have other organic compounds, in addition to 1- chloro-3,3,3-trifluoropropene.
  • reflux stream 40 from second organic layer may comprise significant amounts of 1,3,3,3-tetrafluoropropene (HFO-
  • HFC-245fa 1,1,1,3,3 - pentafiuoropropane
  • other impurities e.g., about 70 t.% HFO-1234ze, about 15 wt.% HFC-245fa, and about 15 wt.% l-chloro-3,3,3- trifluoropropene
  • Purified 1 -chloro-3,3,3-trifluoropropene removed from distillation column 20 as bottoms stream 24 may include less than 50 ppm, less than 40 pprn, less than 25 ppm, less than 20 ppm, or 10 ppm or less, of water or, in other embodiments, may include as little as 10 ppm, 15, ppm, or 20 ppm, or as great as 25 ppm, 40 ppm, or 50 ppm of water, or any amount of water within any range defined between any two of the foregoing values.
  • the purified l-chloro-3,3,3- trifluoropropene (1233zd) may be used as an end product such as a refrigerant, blowing agent, propellant, or diluent for gaseous sterilization, or it may be used as a monomer, as an intermediate, or otherwise further processed for the production of alternative HFOs or similar compounds.
  • the purified azeotrope meets the current need in the art for mixtures that have no ozone depletion potential and are negligible contributors to greenhouse global w arming and are nonflammable.
  • a mixture may be utilized in a wide range of uses such as, but not limited to, refrigerants, blowing agents, propellants and diluents for gaseous sterilization.
  • the azeotrope may be provided in combination with other useful additives or ingredients for such purposes.
  • the top water layer is withdrawn and expected to have about 4 lbs of water and to contain about 2,000 ppm of dissolved HCFO-1233zd or 0.008 lbs. This water can be recycled to the caustic scrubber for organic recover ⁇ ' or be disposed.
  • the bottom HCFO-1233zd organic layer is withdrawn and expected to have about 1,000 lbs of HCFO-1233zd and to contain about 400 ppm of dissolved water or 0.4 lbs.
  • This resulting HCFO-1233zd stream is then dried with a drying agent such as molecular sieve 3A or 4A, activated alumina, silica gel, CaSCU, and the like.
  • the drying equipment size can be made much smaller than those used in prior art processing. Furtliermore, given that the molecular sieve can be regenerated, the ultimate drying agent consumption can be minimized.
  • 1,000 lbs of liquid crude HCFO-1233zd containing 10 lbs of HF acid is mixed with about 300 lbs of water and/or diluted caustic solution and then washed to remove the acid at su b- cooled temperature while maintaining the mixture in a liquid phase.
  • the resulting wet and acid free HCFO-1233zd will then flow into a decanter.
  • the water or caustic solution will settle as top layer while the HCFO-1233zd will settle as bottom layer.
  • the above can be carried out stage-wise (e.g., first washing with water and decanting, then followed by washing with aqueous caustic and decanting, etc.).
  • the top water or caustic layer is withdrawn and expected to have about 300 lbs of water and to contain about 2,000 ppm. of dissolved HCFO-1233zd or 0.6 lbs. This water or caustic solution can subsequently be heated or stripped to recover valuable organic or be disposed.
  • the bottom HCFO-1233zd organic layer is withdrawn and expected to have about 1,000 lbs of HCFO-1233zd and to contain about 400 ppm of dissolved water or 0.4 lbs.
  • This resulting HCFO-1233zd stream is then dried with a drying agent such as molecular sieve 3 A or 4A, activated alumina, silica gel, CaSCU, and the like.
  • the drying equipment size can be made much smaller than those used in prior art processing. Furthermore, given that the molecular sieve can be regenerated, the ultimate drying agent consumption can be minimized.
  • Example 3 Processing of Crude 1233zd in a Pilot Plant [0058] 100 lbs of wet and acid-free crude HCFO-1233zd vapor from the caustic scrubber outlet is condensed in a condenser. The condensed wet HCFO-1233zd will then flow into a decanter. The water will settle as top layer while the HCFO-1233zd will settle as bottom layer,
  • the bottom HCFG-1233zd organic layer is withdrawn.
  • This resulting HCFO-1233zd stream is then dried with a drying agent such as molecular sieve 3A or 4A, activated alumina, silica gel, CaS0 , and the like.
  • the organic layer may be further processed, such as by forming an azeotropic or azeotrope-like composition to further separate water and l-chloro-3,3,3- trifluoropropene.
  • Example 4 1,000 lbs hr of wet and acid-free 1-chloro- 3,3,3-trifluoropropene vapor was condensed in a condenser.
  • the resulting mixture was then sent to a phase separator. Water settled as the top layer while the l-chloro-3,3,3-trifluoropropene settled as the bottom (organic) layer.
  • the water layer contained 2,000 ppm crude l-chloro-3,3,3- trifluoropropene or about 0.2 lbs/hr organic.
  • the water layer containing l-chloro-3,3,3- trifiuoropropene was then processed as below according to Example 4 and Example 5.
  • This overhead mixture was then sent to a phase separator or caustic scrubber to re- separate out the water from the l-chloro-3,3,3-trifluoropropene contained in the overhead.
  • the top layer was found to contain the 0,41b/hr of water and may either be recycled back to die first phase separator, may be discarded, or may be partially recycled.
  • the water phase of first phase separator may also be discarded or sent for further processing.
  • the organic phase was then returned to the distillation column as reflux.
  • the bottoms was found to yield nearly 100% l -chloro-3,3,3 ⁇ trifluoropropene, whereas the reflux scream 40 was found to contain about 50 ppm of water.
  • composition of the bottoms stream was able to be controlled to yield between 1 ppm by weight water to about 90 ppm by weight water.
  • a substantially pure and dry l-chloro-3,3,3-trifluoropropene was removed from the distillation column.
  • azeotropic or azeotropic-like compositions of l-chloro-3,3,3-trifluoropropene and water can be used to recover l -chloro-3,3,3- trifluoropropene in an economical fashion.

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Abstract

La présente invention concerne des procédés de séparation qui utilisent des compositions azéotropiques ou de type azéotropique de 1-chloro -3,3,3-trifluoropropène (HCFO -1233zd) qui permettent des taux de récupération améliorés de 1-chloro -3,3,3-trifluoropropène pendant ou après des processus de fabrication. De tels procédés de récupération ou de séparation peuvent utiliser les propriétés uniques de la composition azéotropique ou de type azéotropique avec diverses combinaisons de techniques de séparation (par exemple, distillation et décantation) qui produisent des compositions hautement pures de 1-chloro -3,3,3-trifluoropropène et offrent simultanément des rendements élevés de 1-chloro -3,3,3-trifluoropropène. De telles compositions hautement pures de 1-chloro -3,3,3-trifluoropropène peuvent trouver des applications utiles dans la technologie des polymères en tant que monomères ou co-monomères.
PCT/US2017/063247 2016-12-02 2017-11-27 Procédé de séchage de hcfo-1233zd WO2018102250A1 (fr)

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Application Number Priority Date Filing Date Title
CN202310293598.7A CN116396143A (zh) 2016-12-02 2017-11-27 用于干燥hcfo-1233zd的方法
MX2019006410A MX2019006410A (es) 2016-12-02 2017-11-27 Proceso para secar 1-cloro-3,3,3-trifluoropropeno (hcfo-1233zd).
EP17876338.9A EP3548458A4 (fr) 2016-12-02 2017-11-27 Procédé de séchage de hcfo-1233zd
KR1020197015714A KR102652080B1 (ko) 2016-12-02 2017-11-27 Hcfo-1233zd를 건조시키는 방법
CN201780074649.XA CN110035988A (zh) 2016-12-02 2017-11-27 用于干燥hcfo-1233zd的方法

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US15/368,027 US9926244B2 (en) 2008-10-28 2016-12-02 Process for drying HCFO-1233zd
US15/368,027 2016-12-02

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WO2018102250A1 (fr) * 2016-12-02 2018-06-07 Honeywell International Inc. Procédé de séchage de hcfo-1233zd
US20220396537A1 (en) * 2019-11-06 2022-12-15 Honeywell International Inc. Azeotrope or azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (hcfo-1233xf) and water
CN115779497A (zh) * 2022-12-07 2023-03-14 九江中船消防设备有限公司 一种2-溴-3,3,3-三氟丙烯除水装置

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EP3548458A4 (fr) 2020-07-15
JP2022110129A (ja) 2022-07-28
JP7402271B2 (ja) 2023-12-20
KR102652080B1 (ko) 2024-03-28
CN110035988A (zh) 2019-07-19
EP3548458A1 (fr) 2019-10-09
KR20190083347A (ko) 2019-07-11

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