WO2024049866A2 - Récupération/recyclage de mousse solide et récupération de liquide : compositions et procédés - Google Patents

Récupération/recyclage de mousse solide et récupération de liquide : compositions et procédés Download PDF

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Publication number
WO2024049866A2
WO2024049866A2 PCT/US2023/031480 US2023031480W WO2024049866A2 WO 2024049866 A2 WO2024049866 A2 WO 2024049866A2 US 2023031480 W US2023031480 W US 2023031480W WO 2024049866 A2 WO2024049866 A2 WO 2024049866A2
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WO
WIPO (PCT)
Prior art keywords
reclaimed
halogenated
liquid
unreclaimed
1336mzz
Prior art date
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PCT/US2023/031480
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English (en)
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WO2024049866A3 (fr
Inventor
Sheng Peng
Jeffrey B. Sowder
Barbara Haviland Minor
Jian SUN-BLANKS
Andrew R PANSULLA
Joshua Hughes
David Matthew Snyder
Anthony F. Stasio
Raymond Wu
Original Assignee
The Chemours Company Fc, Llc
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Application filed by The Chemours Company Fc, Llc filed Critical The Chemours Company Fc, Llc
Publication of WO2024049866A2 publication Critical patent/WO2024049866A2/fr
Publication of WO2024049866A3 publication Critical patent/WO2024049866A3/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/0026—Recovery of plastics or other constituents of waste material containing plastics by agglomeration or compacting
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/04—Disintegrating plastics, e.g. by milling
    • B29B17/0404—Disintegrating plastics, e.g. by milling to powder
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/04—Disintegrating plastics, e.g. by milling
    • B29B2017/0424—Specific disintegrating techniques; devices therefor
    • B29B2017/0468—Crushing, i.e. disintegrating into small particles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/04—Condition, form or state of moulded material or of the material to be shaped cellular or porous
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0012—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular thermal properties
    • B29K2995/0015—Insulating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00—Other particular articles
    • B29L2031/762—Household appliances
    • B29L2031/7622—Refrigerators
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • 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
    • F25B2345/00—Details for charging or discharging refrigerants; Service stations therefor
    • F25B2345/001—Charging refrigerant to a cycle
    • 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
    • F25B45/00—Arrangements for charging or discharging refrigerant

Definitions

  • the present invention relates to halogenated liquid and foam waste reclamation where spent halogenated liquids, such as refrigerants, solvents, immersion fluids, and foam wastes are reclaimed by physical and/or chemical treatments, converted to high purity components, compositions and products, and optionally compositionally rebalanced to meet the quality requirements of AHRI_700_2019 for reuse and recycle.
  • spent halogenated liquids such as refrigerants, solvents, immersion fluids, and foam wastes
  • Halogenated olefins e.g., hydrochloroolefins (HCO), chlorofluoroolefin (CFO), hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs) have been developed and are currently being used to replace chlorofluorocarbons (CFCs), hydrochlorofluorocarbons (HCFCs), and hydrofluorocarbons (HFCs), thereby providing heat transfer medium having lower global warming potential (GWP) and ozone depleting potential (ODP) properties which need to be reclaimed.
  • HCO hydrochloroolefins
  • CFO chlorofluoroolefin
  • HFOs hydrofluoroolefins
  • HCFOs hydrochlorofluoroolefins
  • HFCs hydrofluorocarbons
  • halogenated olefins HCOs, HFOs and HCFOs as well as fluorinated ethers, e.g., hydrofluoroether (HFE), fluoropolyether (PFPE, HFPE), hydrofluoroolefinic ether (HFOE), and hydrofluorocarbons (HFCs), collectively halogenated liquids, also find use as solvents, blowing agents, foam producing, cleaning and dielectric fluids for electronics which need to be reclaimed after use to reduce waste.
  • fluorinated ethers e.g., hydrofluoroether (HFE), fluoropolyether (PFPE, HFPE), hydrofluoroolefinic ether (HFOE), and hydrofluorocarbons (HFCs)
  • HFE hydrofluoroether
  • PFPE fluoropolyether
  • HFOE hydrofluoroolefinic ether
  • HFCs hydrofluorocarbons
  • the present invention is directed to integrated reclamation methods which treat and convert spent (e.g., used, contaminated) halogenated liquids and spent foam waste into high purity liquids, compositions and solids which meet industry standards for reuse and recycling.
  • spent halogenated liquids and foam wastes are recovered (collected) from various sources, such as systems circulating heat transfer liquids, storage facilities, discarded sources of refrigerants, foam making facilities, foam recycle centers, etc.
  • Physical and chemical properties of the spent liquids can be assessed, and treatments selected to remove contaminants, moisture, water, acidity, gases, e.g., air, oil, particulates/solids, stabilizers, etc., and provide high purity halogenated liquid components and mixtures/blends.
  • distillation or decanting may also be used.
  • Moisture removal can involve the use of molecular sieves or decanting or the combination of these two.
  • Distillation can be used to separate and/or purify liquid mixtures and liquid components of the spent halogenated liquids, for example separate R-514A into dichloroethylene (R-1130) and 1 ,1 ,1 ,4,4,4-hexafluorobut-2-ene (Z-1336mzz).
  • compositions including, but not limited to blends of at least one of HFO-E-1336mzz, HFO-Z-1336mzz, HFO-Z/E 1336mzz, HCFO-E-1224yd, HCFO- E-1233zd, HCFO-Z-1233zd, and HCFO-Z-1224yd from treatment using the disclosed reclamation process.
  • a stabilizer package includes at least one of an antioxidant, acid acceptor and metal stabilizer where the antioxidant is selected from butylated hydroxytoluene, butylated hydroxyanisole, tertiary-butylhydroquinone, 4- methoxyphenol, propyl 3,4,5-trihydroxybenzoate, the acid acceptor is selected from epoxy butane, amine, and acetaldehyde di-methylhydrazone (ADH) and the metal stabilizer is selected from N,N'-bis(salicylidene)-1 ,2-propanediamine, benzotriazole and its derivatives.
  • the antioxidant is selected from butylated hydroxytoluene, butylated hydroxyanisole, tertiary-butylhydroquinone, 4- methoxyphenol, propyl 3,4,5-trihydroxybenzoate
  • the acid acceptor is selected from epoxy butane, amine, and acetaldehyde di-methylhydrazone (ADH)
  • the metal stabilizer
  • HFO-E-1336mzz HFO-Z-1336mzz
  • HFO- Z/E 1336mzz HFO-Z-1224yd
  • HCFO-E-1233zd R-514A
  • HFO-E-1336mzz HFO- Z-1336mzz
  • HCFO-1233zd HCFO-1224yd components and blends.
  • liquid blend blowing agents including but not limited to at least one of E-1336mzz, Z- 1336mzz, E-1233zd, and Z-1224yd.
  • Vertrel TM specialty fluids such as Vertrel XF
  • OpteonTM specialty fluids such as SF10, SF30, SF33, CFX- 70, SF79, SF80, SF01 , SF05
  • 3M hydrofluoroethers such as Novec 7100, Novec 7200, Novec 7300, Novec 7500, Novec 649, Novec 71 DE, Novec 71 DA, Novec 72DA, Novec 72DE, Novec 71 IPA, Novec 73DE
  • Microcare MCF such as Microcare MCF.
  • the spent halogenated liquids including but not limited to liquid refrigerants, refrigerant blends, liquid blowing agents, solvents, and/or immersion coolants are collected, assessed and treated to remove at least one of acidity, oil, particulates/solids, stabilizer, and spent stabilizer, and moisture, and separated, and optionally compositionally rebalanced to produce high purity, industry compliant halogenated liquid components and blends for reuse as refrigerants, liquid blowing agents, solvents, and/or immersion coolants (fluids).
  • one or more unreclaimed (spent) chlorofluoroolefin (CFO), hydrochloroolefin (HCO), hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), hydrofluoroolefinic ether (HFOE), hydrofluoroketone (HFK), fluoroketone (FK) liquids are reclaimed to produce high purity components and blends.
  • hydrofluoroolefin (HFO) liquids and/or hydrochlorofluoroolefin (HCFO) liquids are reclaimed.
  • hydrofluoroether (HFE) liquids are reclaimed.
  • mixtures of one or more unreclaimed (spent) hydrofluoroolefin (HFO) liquids and/or hydrochlorofluoroolefin (HCFO) liquids and hydrofluoroether (HFE) liquids are reclaimed to produce high purity HFO, HCFO and HFE components and blends.
  • mixtures of one or more unreclaimed (spent) chlorofluoroolefin (CFO) liquids, hydrochloroolefin liquids (HCO) hydrofluoroolefin (HFO) liquids, hydrochlorofluoroolefin (HCFO) liquids, hydrofluoroether (HFE) liquids, fluoroketone (FK) and hydrofluoroketone (HFK) liquids are reclaimed to produce high purity CFO, CHO, HFO, HCFO, HFE and HFK components and blends.
  • refrigerant liquids are reclaimed.
  • solvents are reclaimed.
  • immersion coolants are reclaimed.
  • one of more of the compounds identified in Table 3 are reclaimed.
  • one of more of the compounds identified in Table 4 are reclaimed.
  • any of the reclaimed compositions disclosed herein are packaged in containers constructed of any suitable material and design that is capable of sealing the compositions.
  • suitable containers comprise pressure resistant containers such as a tank, a filling cylinder, and a secondary filing cylinder.
  • the container can be constructed from any suitable material such as carbon steel, manganese steel, chromium- molybdenum steel, among other low-alloy steels, stainless steel and in some case an aluminum alloy.
  • Refrigerant containing compositions stored in these containers can be transferred to a heat transfer system and, in turn, used as a working fluid.
  • spent foam wastes are collected, and crushed to form processible solids and release trapped vapors.
  • the crushed solids are pelletized and the vapors collected, separated and purified into reusable components and compositions.
  • one or more molecular sieves beds are used to remove water from the halogenated liquid, e.g., refrigerant, solvent, blowing agent and immersion fluid, e.g., water above or below its saturation point (greater than 350 ppm).
  • halogenated liquid e.g., refrigerant, solvent, blowing agent and immersion fluid, e.g., water above or below its saturation point (greater than 350 ppm).
  • unsolubilized water above its saturation point is removed from the refrigerant, solvent, blowing agent, trapped vapor and immersion fluid using distillation or decanting.
  • refrigerant blends, solvent blends, immersion fluids, and/or commercial blends are purified and, for example: separated into its components, such as R-514A into dichloroethylene (DCE) and Z- 1336mzz.
  • DCE dichloroethylene
  • the stabilizer and/or stabilizer package includes, but is not limited to, an antioxidant selected from butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), tertiary-butylhydroquinone, 4-methoxyphenol, propyl 3,4,5- trihydroxybenzoate), an acid acceptor (epoxy butane, amine, and acetaldehyde dimethylhydrazone (ADH)), and optionally a metal stabilizer (N,N'-bis(salicylidene)-1 ,2- propanediamine, benzotriazole and its derivatives).
  • BHT butylated hydroxytoluene
  • BHA butylated hydroxyanisole
  • ADH acetaldehyde dimethylhydrazone
  • metal stabilizer N,N'-bis(salicylidene)-1 ,2- propanediamine, benzotriazole and its derivatives.
  • FIG. 1 illustrates a method and system for reclaiming unreclaimed halogenated liquids according to an embodiment of the present invention.
  • Fig. 2 illustrates a method and system for foam waste reclamation according to an embodiment of the present invention.
  • FIG. 3 illustrates a method and system for foam waste reclamation according to another embodiment of the present invention.
  • Fig. 4 illustrates one embodiment of the present invention.
  • Fig. 5 illustrates system for purifying unreclaimed (non-purified) refrigerant liquids
  • Fig 6 illustrates a service center system.
  • the present invention is directed to integrated reclamation methods which treat and convert spent, e.g., used, contaminated, halogenated liquids and foam waste into high purity liquids, compositions and solids which meet industry standards for reuse and recycling.
  • Properties of the spent halogenated liquids can be assessed, and physical/chemical treatments selected to clean up the spent halogenated liquids to remove e.g., contaminants, moisture, water, acidity, gases, e.g., air, oil, particulates/solids, stabilizers, etc.
  • distillation or decanting may also be used.
  • Moisture removal can involve the use of molecular sieves, decanting.
  • Distillation can be used to separate and/or purify liquids and liquid components of the spent halogenated liquids, for example separate R-514A, into dichloroethylene (R-1130) and 1 ,1 ,1 ,4,4,4-hexafluorobut-2-ene (Z-1336mzz).
  • the reclaimed halogenated liquids may be reused in a wide variety of applications as substitutes for CFCs and for compositions containing less desirable HCFCs.
  • the present reclaimed halogenated liquids are useful as blowing agents, refrigerants, heating agents, power cycle agents, immersion coolants and cleaning agents.
  • the reclaimed halogenated liquids disclosed herein are packaged in containers constructed of any suitable material and design that are capable of sealing the liquid and/or liquid compositions. Examples of suitable containers comprise pressure resistant containers such as a tank, a filling cylinder, and a secondary filing cylinder.
  • the container can be constructed from any suitable material such as carbon steel, manganese steel, chromium-molybdenum steel, among other low-alloy steels, stainless steel and in some case an aluminum alloy. Refrigerant-containing compositions stored in these containers can be transferred to a heat transfer system and, in turn, used as a working fluid.
  • the liquid refrigerants, liquid blowing agents, solvent and/or immersion coolants (dielectric compatible heat transfer medium for electronics) to be reclaimed are selected from at least one hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), fluoropolyethers (PFPEs, HFPEs) or hydrofluoroolefinic ether (HFOE), and hydrofluorocarbons (HFCs).
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • HFE hydrofluoroether
  • PFPEs, HFPEs fluoropolyethers
  • HFOE hydrofluoroolefinic ether
  • HFCs hydrofluorocarbons
  • the liquid refrigerant and/or liquid heat transfer medium does not undergo a phase change and can be used in a coolant circuit to remove/transfer heat from power systems, vehicles, an exhaust system of a vehicle, an internal combustion engine (ICE).
  • ICE internal combustion engine
  • Hydrofluoroethers are compounds containing carbon, hydrogen and fluorine and also containing ether linkages.
  • Hydrofluoroolefins are compounds containing carbon, hydrogen and fluorine and also containing double bonds.
  • Hydrofluoroolefins are compounds containing carbon, hydrogen, fluorine and also a double bond.
  • ODP is defined in the “Scientific Assessment of Ozone Depletion, 2002,” a report of the World Meteorological association, incorporated here by reference.
  • GWP is defined relative to that of carbon dioxide and over a 100-year time horizon and defined in the same reference as for the ODP mentioned above.
  • a refrigerant is a compound or mixture of compounds used as working fluid used to carry heat from a heat source to a heat sink. Such heat transfer compositions may also be useful as a refrigerant in a cycle wherein the fluid undergoes a phase change; that is, from a liquid to a gas and back, or vice versa.
  • heat transfer systems include but are not limited to air conditioners, freezers, refrigerators, heat pumps, water chillers, flooded evaporator chillers, direct expansion chillers, walk-in coolers, high temperature heat pumps, mobile refrigerators, mobile air conditioning units, electric storage cooling systems, battery cooling, immersion cooling systems, data-center cooling systems, and combinations thereof.
  • immersion cooling is used to cool electronic devices, such as datacenter servers, insulated-gate bipolar transistor (IGBT) devices, telecommunication infrastructure, military electronics, televisions (TVs), cell phones, monitors, drones, automotive batteries, powertrains for electric vehicles (EVs), avionics devices, power devices and displays.
  • Immersion cooling systems are heat transfer devices wherein there is no compressor, and the heat transfer medium possesses suitable dielectric properties.
  • the object to be cooled is at least partially immersed in (in direct contact with) the heat transfer fluid contained in a vessel.
  • the heat transfer fluid may evaporate and condense in the vessel. In other embodiments, there may be no phase transition involved.
  • foam wastes are formed from compositions which generally include one or more components capable of forming foams and blowing agents.
  • the blowing agent compound is at least one of E-1336mzz, Z-1336mzz, E-1233zd, and Z-1224yd.
  • a refrigerant is a compound or mixture of compounds (blend) that function as a heat transfer fluid in a cycle wherein the fluid undergoes a phase change from a liquid to a gas and back.
  • compositions comprising, “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
  • a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
  • “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • transitional phrase “consisting essentially of” is used to define a composition, method that includes materials, steps, features, components, or elements, in addition to those literally disclosed provided that these additional included materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention, especially the mode of action to achieve the desired result of any of the processes of the present invention.
  • the term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of.”
  • Fig. 1 100 illustrates a non-limiting example of the process and system for reclaiming halogenated liquids and/or vapors according to the invention.
  • the unreclaimed (spent) liquids include hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFO), hydrofluoroethers (HFEs) and mixtures and blends, in particular at least one of E-1336mzz, Z- 1336mzz, E-1233zd, and Z-1224yd and R-514A.
  • HFOs hydrofluoroolefins
  • HCFO hydrochlorofluoroolefins
  • HFEs hydrofluoroethers
  • the unreclaimed (spent) liquids are fluoro- and perfluoro- butanes, pentanes, hexanes, heptanes, and octanes including, but not limited to, 1 ,1 , 1 ,2, 2, 3, 3, 4, 4, 5, 5, 6, 6 -tridecafluorooctane, 1 ,1 ,1 , 2, 2, 3, 4, 5,5,5- decafluoropentane, 1 ,1 ,1 ,3,3-pentafluorobutane, 1 , 1 ,2, 2, 3,3,4- heptafluorocyclopentane and tridecafluorooctane.
  • the unreclaimed (spent) liquids include fluorinated and perfluorinated C4-C7 unsaturated compounds, such as
  • the unreclaimed (spent) solvent includes, but is not limited, to saturated or unsaturated compounds containing only carbon, fluorine, and hydrogen atoms, wherein the number of carbons is 4-10.
  • Specific examples include tridecafluorooctane, decafluoropentane, pentafluorobutane, heptafluorocyclopentane, pentadecafluoroheptane, and hexafluorobutene.
  • unreclaimed (spent) halogenated liquids include for example, Z-1 ,1 ,1 ,4,4,4-hexafluoro-2- butene, 1 ,3,4,4, 4-pentafluoro-3-trifluoromethyl-1 -butene, 1 ,1 ,1 ,4,4,5,5,5-octafluoro-2- pentene, perfluorobutyl methyl ether, perflurobutyl ethyl ether, perfluoroisopropylmethyl ether, perfluoroethyl isopropyl ketone, heptafluorocyclopentane, and E-1 ,1 ,1-trifluoro-3-chloro-2-propene, alone or in combination with the fluoroethers disclosed in U.S.
  • Patent N. 9,840,685 B2 the disclosure of which is incorporated herein by reference in its entirety, as well as combinations with methylperfluoroheptene ether (M PH E) and trans-1 ,2- dichloroethylene, or the compositions of U.S. Patent No. 9,428,717B2, the disclosure of which is incorporated herein by reference in its entirety.
  • the unreclaimed (spent) liquid can include any of the immersion cooling liquids disclosed in U.S. Patent Application Publication No. 2020/0178414, the disclosure of which is incorporated herein by reference in its entirety.
  • halogenated liquids to be reclaimed and described herein is transferred from the recovery/collection system 110 and liquid, where appropriate, is analyzed and its quantity determined in station or system 120 to detect and measure impurities, including but not limited to NAG (non-absorbable gases), acids, solids, water and/or high boiling residue content.
  • impurities including but not limited to NAG (non-absorbable gases), acids, solids, water and/or high boiling residue content.
  • the unreclaimed halogenated liquids e.g., refrigerant, liquid blowing agent, solvent, immersion colling fluid
  • GC-FID GC-TCD
  • GC-MS FTIR
  • Goetz Bub Karl Fischer
  • Karl Fischer Byk-Garner Color
  • various other analytical methods to determine and optionally confirm the identity of the unreclaimed halogenated liquids.
  • organic product analysis involves gaschromatography (GC/MS) or liquid chromatography.
  • NAG non-condensable gases
  • NAG non-absorbable gases
  • concentration of non-condensable gases (NCG) or non-absorbable gases (NAG) may vary or be altered, resulting in a concentration of less than 1 .5 volume percent at 25°C, per AHRI 700, preferably below 0.9 volume percent at 25°C per AHRI 700.
  • NAG typically comprises air, (which is typically comprised of 78% nitrogen, 21 % oxygen, and about 1 % argon), accumulated in the vapor phase of refrigerants where the solubility of air in the liquid phase is extremely low. While reducing the total amount of NAG contained within liquid may be important, it is typically more desirable to reduce the oxygen containing portion of the NAG preferentially over the nitrogen portion.
  • NCG may be detected using one of infrared sensors, UV sensors, NIR sensors, ion mobility or plasma chromatographs, gas chromatography, refractometry, mass spectroscopy, high temperature thick film sensors, thin film field effect sensors, pellistor sensors, Taguchi sensors and quartz microbalance sensors as disclosed in U.S. Patent 2008/0069177 incorporated herein by reference in its entirety.
  • the unreclaimed liquid component or composition may be analyzed as described above to assess the physical and chemical properties of the unreclaimed liquid composition and perform a purity check to see how it compares to the industry standard of AHRI-700.
  • a first or primary purification will take place using a distillation column (adsorption/desorption and cryogenic cooling and/or other separations techniques) in system 130 and the first stage purified liquid reanalyzed and the purify rechecked.
  • the first or primary purification system will optionally include column with absorbent/adsorbent to remove inhibitors and/or stabilizers in the unreclaimed liquid compositions disclosed herein.
  • the column (not shown) may be upstream or downstream of the distillation component of system 130.
  • silica gel or other molecular sieve materials is used as the medium to remove the inhibitors and/or stabilizers, the unreclaimed liquid can be passed through the bed of silica gel and the inhibitor free ‘partially’ reclaimed product is transferred to one of more distillation columns to separate and isolate individual liquid components as the case may be.
  • the primary purification does not provide a treated product that is AHRI-700 compliant, it is transferred from system 130 to system 140 for further processing including targeted purification for NAG (purge stations), water (distillation/desiccant dryer), solids (filters), acidity (base bath), high boiling residue/chloride (distillation), and reanalyzed in the weighing and testing station, and purity rechecked to verify purity and industry compliance in system 140.
  • the NAG reduction station may contact the partially reclaimed liquid composition with a reducing agent, such as a metal powder, which may react with oxygen or other oxidizable components of the unreclaimed liquid composition.
  • the reducing agent may include iron powder. Treatment by the NAG reduction station may result in the concentration of one or more components of the partially reclaimed liquid composition being reduced to less than one or more predetermined thresholds.
  • reclaimed liquid components from 130 or 140 are mixed with additional fresh/virgin/high purity liquid components to provide a reconstituted, compositionally rebalanced, and reclaimed liquid, e.g., refrigerant, solvent, immersion coolant, blowing agent, composition compliant with AHRI 700-19 standards in system 150.
  • reclaimed liquid e.g., refrigerant, solvent, immersion coolant, blowing agent
  • Tracers, stabilizers, and conventional additives are added in system 160, and then a final purity check is performed so that reclaimed and reconstituted liquid is AHRI 700-19 compliant.
  • Each system 110, 120, 130, 140, 150 and 160 includes components for receiving and transferring liquid composition between upstream and downstream systems, such as flowlines, valves, pumps, controls, etc. (not shown).
  • NAGs are separated from the refrigerant using a membrane which is placed such that the NAGs can pass through the membrane and are removed while the refrigerant does not pass through the membrane.
  • system 200 illustrates a non-limiting example of a system and method for foam waste reclamation.
  • Foam waste including but not limited to rigid polyurethane
  • recovery system 210 is delivered, collected, sorted and weighed in recovery system 210, and then after sorting and weighing, transferred to treatment system 220 to physically reduce the dimensions of the foam waste into a suitable size by crushing or other technique.
  • the foam waste comprises a closed cell, rigid polyurethane foam, foam blowing agents and air remain within the cells.
  • the rigid foam is, crushed, pulverized, or shredded the blowing agent and air will be released.
  • the blowing agent that is released includes but is not limited to combinations of HFC and/or HFO components selected from HFC-134a, HFC-245fa, HFC-365mfc, HFC- 227ea, HCFO1233zd(E), HCFO-1224yd(Z), HFO-1336mzz(E) and HFO- 1336mzz(Z). Hydrocarbons may also be included such as (cyclopentane, isopentane, normal pentane. Generally, the released cell gas will be comprised of between 50 to 99.5 vol% air, and the balance the HFC and/or HFO.
  • the concentration could vary due to the amount of blowing agent used to create the foam, the amount lost to atmosphere during the life of the foam, the amount of air that infiltrates the foam during the life of the foam, as well as the amount of air introduced during reclaiming and/or recycling process, and the efficiency of the foam pulverization.
  • a vapor stream is formed and sent to one of the purification systems 130 and/or 140 from system 240, or a dedicated distillation system (not shown).
  • the cell gas composition would be known, prior to processing, as recovering the blowing agent would be a simpler process for neat HFC or HFO/air mixtures.
  • the integrated reclamation systems include testing stations for identifying components of products to be reclaimed, the vapor removed during crushing can be analyzed before purification. Crushed and/or pelletized foam waste from system 220 is collected and stored.
  • foam waste is sent through a process under vacuum (partial or total) where the foam would be crushed and pulverized under vacuum, and the vapor stream sent to a distillation process for liquid recovery. Solids are sent to a pelletizer for subsequent recycle. Once the foam is pulverized, the remaining solid portion is no longer a foam, it is polyurethane solids. These solids can be recovered, pelletized, or compressed and incinerated for fuel value, used as a concrete filler, or it is possible to recycled by glycolysis to chemically reduce the solids to a liquid polyol, which can be used again to make another polyurethane foam.
  • FIG. 4 illustrates a non-limiting example of a service center 400 including one or more systems 110, 120, 130, 140, 150 and 160 which can be connected to a mobile transport vehicle 420 to charge reclaimed refrigerant/refrigerant blends from system 410 through line 412, or recharge a refrigerant or refrigerant blend through line 412 which has been processed in system 410, and optionally withdraw spent refrigerant through line 422 from vehicle 420 for processing in system 410.
  • Fig. 5 illustrates system 500 for purifying unreclaimed (non-purified) refrigerant liquids from a mixture of N number of chemically distinct liquids collected in Step 1 , unit 510, which contains unpurified liquid mixtures Liquid 1 , Liquid 2.... liquid N.
  • Step 2 liquid components of liquid mixtures are separated via a separation process such as distillation.
  • Step 3 non purified separated liquids could require further processing, e.g., additional distillation removal of NAGs, etc.
  • Step 4 the purified liquid components of Step 4 are compared with industry quality standards, and involve removal of moisture, solids, volatile impurities.
  • additive and/or tracers components are introduced to each purified individual component.
  • Step 6 separated, purified, addivized components can be remixed into other blends or used as pure components.
  • Fig. 6 illustrates a service center system 600 where a source of reclaimed/re-blended refrigerant 610 from a system such as that illustrated in Fig. 5 is connected to a refrigerant circuit 650 of a transport vehicle (not shown) which includes, generally in seriatim, charging valve 612, expansion device 614, heat exchange 620, compressor 630, heat exchange 640 and flow lines 613, 615, 622, 631 and 641.
  • Reclaimed/re-blended refrigerant 610 is charged via line 611 which is in fluid communication with charging valve 612, which when opened charges refrigerant circuit 650.
  • One embodiment disclosed herein comprises a system with a contained supply of reclaimed/re-blended refrigerant, a refrigerant circuit including at least a charging valve and compressor, and a transfer line controllable connected said contained supply of reclaimed/re-blended refrigerant to a charging valve of the circuit.
  • Another embodiment disclosed herein comprises a purification system, a contained supply of purified refrigerant receiving product from the purification system, and a refrigerant circuit including at least a charging valve and compressor, and transfer line controllable connected to said contained supply of reclaimed/re- blended refrigerant to said charging valve. Additional Embodiments
  • the waste or spent halogenated liquids Prior to step a) the waste or spent halogenated liquids are recovered from various sources, such as systems circulating heat transfer liquid, storage facilities, discarded sources of refrigerants.
  • CFO chlorofluoroolefin
  • HCO hydrochloroolefin
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • HFE hydrofluoroether
  • HFOE hydrofluoroolefinic ether
  • HFK hydrofluoroketone
  • FK fluoroketone
  • a process embodiment where the foam waste and/or spent halogenated liquids of a) are: (i) collected from unreclaimed foam waste or unreclaimed halogenated liquids prior to the treating in a).
  • a process embodiment where the treating of a) comprises physical and chemical treatments.
  • a process embodiment where the treating of a) comprises at least one of moisture removal, contaminant removal and distillation.
  • a process embodiment including at least one of a1) an unreclaimed halogenated liquids selected from chlorofluoroolefin (CFO), hydrochloroolefin (HCO), hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), hydrofluoroolefinic ether (HFOE), fluoroketone (FK), hydrofluoroketone (HFK) and mixtures of two or more, a2) optionally identifying contaminants of a1); a3) selecting physical and/or chemical treatments based on a1) and optionally on a2); a4) treating the unreclaimed halogenated liquids of a1) and a2) using the physical and/or chemical treatments selected in step a3) to produce at least a partially reclaimed halogenated liquid; a5) comparing the purity of the at least partially reclaimed halogenated liquid of a3) against an industry standard; a6) optionally, further treating
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) is selected from one of HFO-E/Z-1336mzz, HCFO-Z-1224yd, HCFO-E-1233zd, R-514A (olefin blend comprised of cis- 1 ,1 ,1 ,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1 ,2-dichloroethene (R- 1130(E), HFO-Z/E 1336mzz blends, liquid HFC-245fa and Vertrel XF.
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) is selected from one of Vertrel XF, SF10, SF79, SF80, SF01 , SF05, SF30, SF33, F33E, F22E and F44E (see Tables 1-4).
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) is selected from halogenated liquid comprises one of a hydrofluoroether (HFE) and a hydrofluoroolefinic ether (HFOE).
  • HFE hydrofluoroether
  • HFOE hydrofluoroolefinic ether
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) is a hydrofluoroether (HFE) and comprises one of Novec 7100, Novec 7200, Novec 7300, Novec 7500, Novec 71 DE, Novec
  • HFE hydrofluoroether
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises chlorofluoroolefins (CFOs), hydrochloroolefins (HCOs), hydrochlorofluoroolefins (HCFOs), fluoroketones (FKs) or hydrofluoroketones (HFKs).
  • CFOs chlorofluoroolefins
  • HCOs hydrochloroolefins
  • HCFOs hydrochlorofluoroolefins
  • FKs fluoroketones
  • HFKs hydrofluoroketones
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) is reclaimed a stabilizer package is added to at least one of the partially reclaimed or completely reclaimed halogenated liquids and includes at least one antioxidant, at least one acid acceptor and at least one metal stabilizer where the antioxidant is selected from butylated hydroxytoluene, butylated hydroxyanisole, tertiary-butylhydroquinone, 4-methoxyphenol, propyl 3,4,5- trihydroxybenzoate, the acid acceptor is selected from epoxy butane, amine and acetaldehyde di-methylhydrazone (ADH), and the metal stabilizer is selected from N,N'-bis(salicylidene)-1 ,2-propanediamine, benzotriazole and its derivatives.
  • the antioxidant is selected from butylated hydroxytoluene, butylated hydroxyanisole, tertiary-butylhydroquino
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises HFO-E/Z-1336mzz and HFO-Z/E 1336mzz blends.
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises HCFO-E/Z-1224yd.
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises HCFO-E/Z-1233zd.
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises cis-1 ,1 ,1 ,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1 ,2-dichloroethene (R-1130(E)).
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises Vertrel XF (1 , 1 ,1 , 2, 3, 4, 4, 5,5,5- decafluoropentane).
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises one of MPHE (OpteonTM SF10); a blend comprising 94% trans-1 ,2-dichloroethylene, 5% MPHE and 1 % Vertrel XF (1 ,1 ,1 ,2,3,4,4,5,5,5-decafluoropentane) (OpteonTM SF79); a blend comprising 94% trans-1 ,2-dichloroethylene, 5% MPHE and 1 % Z-1336mzz (OpteonTM SF80); a blend comprising 98.4% Z-1336mzz and 1.6 % ethanol (OpteonTM SF01 ); a blend comprising 60% Z-1336mzz, 25% MPHE and 15% ethanol (OpteonTM SF05); a blend comprising 75% Z-1336mzz and 25% trans-1 ,2-dichloroethylene (OpteonTM SF10);
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises chlorofluoroolefins.
  • a process embodiment where the spent halogenated liquid of a) or the unreclaimed halogenated liquid of a1) comprises hydrofluoroketones (HFK)s
  • a system or method of using embodiments comprising one or more of:
  • a weighing/quantity and testing station comprising analytical systems to determine physical and chemical properties of the unreclaimed liquid selected from one of HFO-E/Z-1336mzz; HCFO-E/Z-1224yd; HCFO-E/Z-1233zd; R-514A (olefin blend comprised of cis- 1 ,1 ,1 ,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1 ,2- dichloroethene (R-1130(E)); HFO-Z/E 1336mzz blends; liquid HFC- 245fa; 1 ,1 ,1 ,2, 3,4,4, 5,5, 5-decafluoropentane (Vertrel XF); MPHE (OpteonTM SF10); a blend comprising 94% trans-1 , 2- dichloroethylene, 5% MPHE and 1 % Vertrel XF (1 , 1 ,1 , 2, 3, 4, 4, 5,5,5- de
  • waste foam treatment station comprising at least one crusher, at least one solids sorter, at least one pelletizer with vapor separation;
  • a first purification system for receiving and treating unreclaimed liquid from said weighing, testing station, vapor from said waste foam treatment station and first transport lines;
  • a target refrigerant system in flow communication with the first and second transport lines to receive treated liquid from the first and second purification systems for adjusting levels of reclaimed liquid components to target refrigerant levels of the AHRI 700 standards following purification at said first and second purification stations, including a blending station to provide reclaimed liquid blends components consistent with AHRI 700 standards;
  • stabilizer package dispensing station to add effective quantities of stabilizer package comprising at least one antioxidant, at least one acid acceptor and at least one metal stabilizer;
  • a purity check station to check the purity of unreclaimed liquid before purification, after the first and/or second purification treatments, and of the at least one first treated product and determining whether or not the first treated product meets or exceeds AHRI 700 standards
  • a system or method of using embodiment where the weighing and testing station include a scale at least one of a GC-FID, GC-TCD, GC-MS, FTIR, Goetz Bub, Karl Fischer, and Byk-Garner Color detector.
  • a system or method of using embodiment where the weighing and testing station include one of infrared sensors, UV sensors, NIR sensors, ion mobility or plasma chromatographs, gas chromatography, refractometry, mass spectroscopy, high temperature thick film sensors, thin film field effect sensors, pellistor sensors, Taguchi sensors and quartz microbalance sensors.
  • a system or method of using embodiment where the weighing and testing station include a scale, GC-MS and Taguchi sensor.
  • a system or method of using embodiment where at least one of the first and second purification systems include one of a distillation column, and adsorption/desorption column, and cryogenic cooler.
  • a system or method of using embodiment where at least one of the first and second purification systems include one an NCG purge units, a water distillation or desiccant dryer unit, a solids filter unit, and an acidity neutralizer, and a high distillation residue column.
  • a process of using embodiments of exchanging heat using reclaimed hydrofluoroethers e.g., methoxy-nonafluorobutane (NovecTM 7100); ethoxynonafluorobutane (NovecTM 7200); 1 ,1 ,1 ,2,2,3,4,5,5,5-decafluoro 3-methoxy-4- (trfluoromethyl) pentane (NovecTM 7300); 3-ethoxy-1 , 1 ,1 ,2, 3, 4, 4, 5, 5, 6, 6, 6- dodecafluoro-2-(trifluoromethyl)hexane (NovecTM 7500); dodecafluoro-2- methylpentan-3-one (NovecTM 649); blend comprising 50% methyl nonafluorobutyl ether and 50% trans-1 ,2-dichloroethylene (NovecTM 71 DE); blend comprising 52.7% methyl nonafluorobutyl ether, 44
  • a process of using embodiments of exchanging heat using reclaimed hydrofluoroketones including but not limited to trifluoroacetone, dodecafluoro- 2-methylpentan-3-one (Novec 649).
  • FK reclaimed fluoroketone
  • HF hydrofluoroketone
  • a process of using embodiments of using reclaimed halogenated liquids selected from one of hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), hydrofluoroolefinic ether (HFOE) as aerosol propellants, refrigerants, cleaning agents, expansion agents for thermoplastic and thermoset foams, heat transfer media, liquid dielectrics, power cycle working fluids, polymerization media, particulate removal fluids, carrier fluids, buffing abrasive agents, and displacement drying agents heat exchanging.
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • HFE hydrofluoroether
  • HFOE hydrofluoroolefinic ether
  • a heat exchanging embodiment comprising charging a system with a working fluid selected from at least one of reclaimed hydrofluoroolefins (HFOs), hydrochlorofluoroolefin (HCFOs), hydrofluoroethers (HFEs), hydrofluoroolefinic ether (HFOEs), and circulating the working fluid.
  • HFOs hydrofluoroolefins
  • HCFOs hydrochlorofluoroolefin
  • HFEs hydrofluoroethers
  • HFOEs hydrofluoroolefinic ether
  • a cooling embodiment cooling comprising directly contacting an electrical component with at least one reclaimed hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroethers (HFE), hydrofluoroolefinic ether (HFOE).
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • HFE hydrofluoroethers
  • HFOE hydrofluoroolefinic ether
  • a heat exchanging embodiment comprising charging a system with a working fluid selected from at least one of a reclaimed fluoroketone (FK) or hydrofluoroketone (HFK) and circulating the working fluid.
  • a cooling embodiment cooling comprising directly contacting an electrical component with at least one of a reclaimed fluoroketone (FK) or hydrofluoroketone (HFK).
  • a process embodiment comprising using at least one reclaimed hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroethers (HFE), hydrofluoroolefinic ether (HFOE) in refrigeration, in air conditioning, in heating, in heat transfer, in conversion of heat into mechanical work in a power cycle, as a foam blowing agent, as a solvent, or in preventing or quenching an electric discharge.
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • HFE hydrofluoroethers
  • HFOE hydrofluoroolefinic ether
  • a process embodiment comprising using at least one reclaimed hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroethers (HFE), hydrofluoroolefinic ether (HFOE), hydrofluoroketone (HFK). with a refrigerant component, an air conditioning component, a heating component, a heat transfer component, a working fluid component, a blowing agent component, a solvent component, or a dielectric component.
  • HFO hydrofluoroolefin
  • HCFO hydrochlorofluoroolefin
  • HFE hydrofluoroethers
  • HFOE hydrofluoroolefinic ether
  • HFK hydrofluoroketone
  • a process embodiment comprising using at least one reclaimed fluoroketone (FK) or hydrofluoroketone (HFK) in refrigeration, in air conditioning, in heating, in heat transfer, in conversion of heat into mechanical work in a power cycle, as a foam blowing agent, as a solvent, or in preventing or quenching an electric discharge.
  • FK reclaimed fluoroketone
  • HFK hydrofluoroketone
  • a process embodiment comprising at least one reclaimed fluoroketone (FK) or hydrofluoroketone (HFK) with a refrigerant component, an air conditioning component, a heating component, a heat transfer component, a working fluid component, a blowing agent component, a solvent component, or a dielectric component.
  • FK reclaimed fluoroketone
  • HFK hydrofluoroketone
  • composition embodiment comprising one or more reclaimed compounds and the compound that has been reclaimed is one of the compounds listed in Table
  • composition embodiment comprising one or more reclaimed compounds and the compound that has been reclaimed is one of the compounds listed in Table
  • a composition embodiment comprising one or more reclaimed compounds and the compound that has been reclaimed is one of the compounds listed in Table 3, optionally containing a tracer.
  • a composition embodiment comprising one or more reclaimed compounds and the compound that has been reclaimed is one of the compounds listed in Table 4, optionally containing a tracer.
  • HFO-E/Z-1336mzz comprises HFO-E 1336mzz, HFO-Z 1336mzz and mixtures of HFO-E 1336mzz and HFO-Z 1336mzz
  • HFO-E/Z-1224yd comprises HFO-E 1336mzz, HFO-Z 1224yd and mixtures of HFO-E 1224yd and HFO-Z 1224yd
  • HCFO-E/Z-1233zd comprises HCFO-E-1233zd, HCFO-Z-1233zd and mixtures of HCFO-E-1233zd and HCFO-Z-1233zd.

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  • Environmental & Geological Engineering (AREA)
  • Mechanical Engineering (AREA)
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  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

L'invention concerne des procédés et des systèmes pour récupérer un liquide usé et des matériaux solides formés à l'aide ou comprenant, mais sans y être limités, des réfrigérants liquides d'oléfine halogénée, des solvants, des fluides d'immersion et de la mousse. L'invention concerne également des compositions et des composants récupérés qui répondent à la qualité des normes de l'industrie AHRI_700_2019.
PCT/US2023/031480 2022-08-31 2023-08-30 Récupération/recyclage de mousse solide et récupération de liquide : compositions et procédés WO2024049866A2 (fr)

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