CN104592942A - Flame-retardant type refrigerant and preparation method thereof - Google Patents
Flame-retardant type refrigerant and preparation method thereof Download PDFInfo
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- CN104592942A CN104592942A CN201410820325.4A CN201410820325A CN104592942A CN 104592942 A CN104592942 A CN 104592942A CN 201410820325 A CN201410820325 A CN 201410820325A CN 104592942 A CN104592942 A CN 104592942A
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- ionic liquid
- flame retardant
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- fire retardant
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 51
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000003507 refrigerant Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000002608 ionic liquid Substances 0.000 claims abstract description 38
- ZDCRNXMZSKCKRF-UHFFFAOYSA-N tert-butyl 4-(4-bromoanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(Br)C=C1 ZDCRNXMZSKCKRF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 20
- 238000005057 refrigeration Methods 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 239000007791 liquid phase Substances 0.000 claims description 12
- 238000005660 chlorination reaction Methods 0.000 claims description 9
- KGLQOUUZPFEOCA-UHFFFAOYSA-N 1-bromo-3,3-difluoroprop-1-ene Chemical class BrC=CC(F)F KGLQOUUZPFEOCA-UHFFFAOYSA-N 0.000 claims description 6
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 3
- ZXLOSLWIGFGPIU-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;acetate Chemical compound CC(O)=O.CCN1CN(C)C=C1 ZXLOSLWIGFGPIU-UHFFFAOYSA-N 0.000 claims description 3
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 claims description 3
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical group FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 6
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical group FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 230000003134 recirculating effect Effects 0.000 description 10
- NOPJRYAFUXTDLX-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-methoxypropane Chemical compound COC(F)(F)C(F)(F)C(F)(F)F NOPJRYAFUXTDLX-UHFFFAOYSA-N 0.000 description 7
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 6
- CWIFAKBLLXGZIC-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-(2,2,2-trifluoroethoxy)ethane Chemical compound FC(F)C(F)(F)OCC(F)(F)F CWIFAKBLLXGZIC-UHFFFAOYSA-N 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000013529 heat transfer fluid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000012773 waffles Nutrition 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 1
- 102100040359 Angiomotin-like protein 2 Human genes 0.000 description 1
- 101000891151 Homo sapiens Angiomotin-like protein 2 Proteins 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- -1 refrigeration system Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
-
- 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
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/11—Ethers
- C09K2205/112—Halogenated ethers
-
- 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
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
-
- 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
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/132—Components containing nitrogen
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses a flame-retardant type refrigerant which comprises the following components in parts by weight: 14.85-28.5 parts of 3-bromo-3,3-difluoropropylene, 0.15-1.8 parts of ionic liquid, 60-80 parts of 2,3,3,3-tetrafluoropropylene and 1-10 parts of 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether. The invention also discloses a method for preparing the refrigerant. The process disclosed by the invention is simple and low in cost, and the prepared refrigerant product has good flame-retardant property and low GWP.
Description
Technical field
The present invention relates to refrigerant art, particularly a kind of flame retardant type refrigeration agent and preparation method thereof.
Background technology
HFO-1234yf is as single working medium refrigeration agent, and have excellent environmental parameter, its global warming potential GWP=4, ozone depletion potential ODP=0, lifetime climate performance (LCCP) is lower than HFC-134a, and air resolvent is identical with HFC-134a.And its system performance is better than HFC-134a.If select HFO-1234yf to substitute HFC-134a refrigeration agent, then car manufactures just can continue to continue to use former on-board air conditioner (Mobile Air-Conditioning, MAC) system.So HFO-1234yf is considered to the young mobile refrigerant replacement compared with tool potentiality, at present in West Europe accept by car manufactures, 2011 start progressively promote.Compare with the atmospheric lifetime refrigeration agent of other alternative HFC-134a of the GWP of HFO-1234yf has obvious environmental advantage, but it has low flammable, has the hidden danger causing fire.Therefore researchist develops the multiple composition containing HFO-1234yf, reduces its combustibility by adding fire retardant.As China Patent Publication No. CN102971394A discloses a kind of heat-transfer system, the method and composition that utilize heat-transfer fluid, described heat-transfer fluid comprises: (a) about 30 % by weight is to about HFC-134a of 65 % by weight; B () about 0 % by weight is to about HFO1234ze of 70 % by weight; (c) about 0 % by weight to about HFO-1234yf of 70 % by weight, condition is that in said composition, the total amount of HFO-1234ze and HFO-1234yf is at least about 35 % by weight, and this weight percent is based on the total amount of component (a)-(c) in said composition.This invention refer to and can reduce combustibility adding of fire retardant.
And for example China Patent Publication No. CN101636466A provides Azeotrope-like compositions comprising tetrafluoeopropene and CF3I and uses thereof, comprise for refrigerant composition, refrigeration system, foaming agent composotion and sprayable composition, comprise aerosol propellants.CF in said composition
3i component can be used as fire retardant, for suppressing the combustibility of HFO1234yf.
Existing method all will utilize and add fire retardant or nonflammable component raising flame retardant resistance, because the poor compatibility of fire retardant and HFO1234yf tetrafluoeopropene, disperse uneven, cause flame retardant effect poor, its refrigerant product prepared has higher GWP compared with the mono-working medium of HFO1234yf simultaneously, still has considerable influence to environment.
Summary of the invention
The technical problem to be solved in the present invention is the defect overcoming prior art, provides that a kind of technique is simple, cost is low, the flame retardant type refrigeration agent of environmental protection and preparation method thereof.
In order to solve the problems of the technologies described above, the present invention is achieved by the following technical solutions: a kind of flame retardant type refrigeration agent, and by weight, it is composed as follows:
Described ionic liquid is preferably the one in chlorination 1-allyl group-3-Methylimidazole, chlorination 1-butyl-3-Methylimidazole, chlorination 1-ethyl-3-methylimidazole, acetic acid 1-ethyl-3-methylimidazole.
The present invention also provides the preparation method of described flame retardant type refrigeration agent, comprises the following steps:
(1) by proportioning, 14.85 ~ 28.5 parts of bromo-3,3-difluoropropenes of 3-are mixed 10 ~ 20h with 0.15 ~ 1.8 part of ionic liquid under liquid phase state, obtains ionic liquid fire retardant;
(2) by proportioning, the ionic liquid fire retardant obtain step (1) and 60 ~ 80 part of 2,3,3,3-tetrafluoeopropene, 1 ~ 10 part of 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether mixture obtain flame retardant type refrigerant product.
Mixture described in step (2) preferably refers to turbulent flow circulation mixing 20-40h under liquid phase state.
First the present invention prepares ionic liquid fire retardant, bromo-for 3-3,3-difluoropropenes (BFO) and ionic liquid is fully dissolved, and generates ionic liquid fire retardant; Ionic liquid fire retardant and 2,3,3,3-tetrafluoeopropene (HFO1234yf), 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether joins in turbulent recirculating still with certain proportioning, obtains product through sufficient turbulent mixing.HFO1234yf, 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether and ionic liquid fire retardant have good solubleness and diffusivity, effectively can reduce the flammable performance of HFO1234yf.
The raw material used in the present invention all can commercially availablely obtain, as ionic liquid can adopt the ionic liquid product of Shanghai Di Bai chemical Technology Co., Ltd.; Bromo-3, the 3-difluoropropenes (BFO) of 3-can adopt
lark waffle learns a skill company limitedproduct; 2,3,3,3-tetrafluoeopropene (HFO1234yf, molecular formula C
3h
2f
4) product of Juhua Group Co. can be adopted; 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347, molecular formula CF
3cH
2oCF
2cF
2h) product of Juhua Group Co. can be adopted.
Turbulent recirculating still in the present invention is commercially available prod, as the turbulent recirculating still product of Wuhan Engineering Univ's development.
Compared with prior art, the present invention has following beneficial effect:
1, technique is simple, cost is low, and first the present invention prepares ionic liquid fire retardant, bromo-for 3-3,3-difluoropropenes (BFO) and ionic liquid is fully dissolved, and generates ionic liquid fire retardant; Ionic liquid fire retardant and 2,3,3,3-tetrafluoeopropene (HFO1234yf), 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347) joins in turbulent recirculating still with certain proportioning, make material be in turbulent state, the mixing of storeroom or dispersion are more quick, even, enormously simplify preparation technology, reduce cost, be conducive to industrialization scale operation;
2, the product prepared has good flame-retardance, and the ionic liquid fire retardant in product has the features such as fluid temperature is interval greatly, soluble end is wide, steam forces down, Heat stability is good, good flame retardation effect; 2,3,3,3-tetrafluoeopropene, 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether and ionic liquid fire retardant have good solubleness and diffusivity, can reduce the flammable performance of HFO1234yf further, improve the flame retardant resistance of refrigeration agent, refrigerant product LFL value (volume %) of the present invention is more than 13.2;
3, environmental protection, refrigeration agent global warming potential (GWP) of the present invention is below 25, and ozone depletion potential (ODP) is 0.
Embodiment
Below in conjunction with specific embodiment, the present invention is further detailed, but the present invention is not limited to described embodiment.
Raw material in the present invention and equipment all can commercially availablely obtain, wherein portion of material and description of equipment as follows:
Bromo-3, the 3-difluoropropenes (BFO) of 3-: purchased from
lark waffle learns a skill company limited.
2,3,3,3-tetrafluoeopropene (HFO1234yf): Juhua Group Co. produces.
1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347): Juhua Group Co. produces.
Ionic liquid (AMIMCI, BMIMCI, EMIMCI, EMIMAc): purchased from Shanghai Di Bai chemical Technology Co., Ltd..
Turbulent flow recirculating still: the turbulent recirculating still product of Wuhan Engineering Univ's development.
Embodiment 1
A kind of flame retardant type refrigeration agent, by every part of 1Kg, the formula that feeds intake is as follows:
Its preparation method is as follows:
The preparation of step (1) ionic liquid fire retardant
By proportioning, in 200L reactor, add 27.16 parts of bromo-3,3-difluoropropenes (BFO) of 3-, 0.84 part of chlorination 1-allyl group-3-Methylimidazole ionic liquid (AMIMCI), under liquid phase state, mix 15h, obtain ionic liquid fire retardant.
Step (2) mixture
By proportioning, the ionic liquid fire retardant that step (1) is prepared and 70 part of 2,3,3,3-tetrafluoeopropene (HFO1234yf), 2 part 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347, molecular formula CF
3cH
2oCF
2cF
2h) add in 200L turbulent flow recirculating still, under liquid phase state, turbulent flow circulation mixing 30h, obtains product.Be numbered WN-1.
Embodiment 2
A kind of flame retardant type refrigeration agent, by every part of 1Kg, the formula that feeds intake is as follows:
Its preparation method is as follows:
The preparation of step (1) ionic liquid fire retardant
By proportioning, in 200L reactor, add 28.5 parts of bromo-3,3-difluoropropenes (BFO) of 3-, 1.5 parts of chlorination 1-butyl-3-Methylimidazole ionic liquid (BMIMCI), under liquid phase state, mix 20h, obtain ionic liquid fire retardant.
Step (2) mixture
By proportioning, the ionic liquid fire retardant that step (1) is prepared and 60 part of 2,3,3,3-tetrafluoeopropene (HFO1234yf), 10 part 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347, molecular formula CF
3cH
2oCF
2cF
2h) add in 200L turbulent flow recirculating still, under liquid phase state, turbulent flow circulation mixing 40h, obtains product.Be numbered WN-2.
Embodiment 3
A kind of flame retardant type refrigeration agent, by every part of 1Kg, the formula that feeds intake is as follows:
Its preparation method is as follows:
The preparation of step (1) ionic liquid fire retardant
By proportioning, in 200L reactor, add 14.85 parts of bromo-3,3-difluoropropenes (BFO) of 3-, 0.15 part of chlorination 1-ethyl-3-methylimidazole (EMIMCI), under liquid phase state, mix 10h, obtain ionic liquid fire retardant.
Step (2) mixture in turbulent recirculation reactor
By proportioning, the ionic liquid fire retardant that step (1) is prepared and 80 part of 2,3,3,3-tetrafluoeopropene (HFO1234yf), 1 part 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347, molecular formula CF
3cH
2oCF
2cF
2h) add in 200L turbulent flow recirculating still, under liquid phase state, turbulent flow circulation mixing 20h, obtains product.Be numbered WN-3.
Embodiment 4
A kind of flame retardant type refrigeration agent, by every part of 1Kg, the formula that feeds intake is as follows:
Its preparation method is as follows:
The preparation of step (1) ionic liquid fire retardant
By proportioning, in 200L reactor, add 18.2 parts of bromo-3,3-difluoropropenes (BFO) of 3-, 1.8 parts of acetic acid 1-ethyl-3-methylimidazoles ionic liquid (EMIMAc), under liquid phase state, mix 18h, obtain ionic liquid fire retardant.
Step (2) mixture
By proportioning, the ionic liquid fire retardant that step (1) is prepared and 75 part of 2,3,3,3-tetrafluoeopropene (HFO1234yf), 5 part 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether (HFE-347, molecular formula CF
3cH
2oCF
2cF
2h) add in 200L turbulent flow recirculating still, under liquid phase state, turbulent flow circulation mixing 25h, obtains product.Be numbered WN-4.
Performance test:
Embodiment 1-4 products obtained therefrom is done flammability test according to U.S.'s ASTM-E681-01 standard, and wherein LFL is the low limit value of combustion limits, and LFL value is larger, and incendivity is lower.LFL value experimental result is in table 1.
Table 1: embodiment 1-4 products obtained therefrom and HFO1234yf Performance comparision
| Numbering | LFL value (volume %) | GWP |
| WN－1 | 16.8 | 23 |
| WN－2 | 19.1 | 25 |
| WN－3 | 14.7 | 15 |
| WN－4 | 13.2 | 21 |
| HFO1234yf | 6.9 | 4 |
Claims (4)
1. a flame retardant type refrigeration agent, is characterized in that by weight, it is composed as follows:
2. flame retardant type refrigeration agent according to claim 1, is characterized in that described ionic liquid is the one in chlorination 1-allyl group-3-Methylimidazole, chlorination 1-butyl-3-Methylimidazole, chlorination 1-ethyl-3-methylimidazole, acetic acid 1-ethyl-3-methylimidazole.
3. the preparation method of flame retardant type refrigeration agent according to claim 1, is characterized in that comprising the following steps:
(1) by proportioning, 14.85 ~ 28.5 parts of bromo-3,3-difluoropropenes of 3-are mixed 10 ~ 20h with 0.15 ~ 1.8 part of ionic liquid under liquid phase state, obtains ionic liquid fire retardant;
(2) by proportioning, the ionic liquid fire retardant obtain step (1) and 60 ~ 80 part of 2,3,3,3-tetrafluoeopropene, 1 ~ 10 part of 1,1,2,2-tetra-fluoro ethyl-2,2,2-trifluoroethyl ether mixture obtain flame retardant type refrigerant product.
4. the preparation method of flame retardant type refrigeration agent according to claim 3, is characterized in that the mixture described in step (2) refers to turbulent flow circulation mixing 20-40h under liquid phase state.
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| CN201410820325.4A CN104592942B (en) | 2014-12-24 | 2014-12-24 | A kind of flame retardant type refrigerant and preparation method thereof |
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| CN104592942B CN104592942B (en) | 2017-11-24 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105885080A (en) * | 2016-05-05 | 2016-08-24 | 巨化集团技术中心 | Foamer composition and preparation method thereof |
| CN107134592A (en) * | 2017-06-27 | 2017-09-05 | 山东大学 | A kind of fluoro ether electrolyte for lithium cells and preparation method thereof |
| JP2020511570A (en) * | 2017-03-06 | 2020-04-16 | アーケマ・インコーポレイテッド | Refrigerant with reduced flammability profile |
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| CN103189466A (en) * | 2010-11-08 | 2013-07-03 | 赢创德固赛有限公司 | Working medium for absorption heat pumps |
| WO2014151344A1 (en) * | 2013-03-15 | 2014-09-25 | Honeywell International Inc. | Low gwp heat transfer compositions containing difluoromethane, a fluorinated ethane and 1,3,3,3-tetrafluoropropene |
| CN104072691A (en) * | 2014-06-26 | 2014-10-01 | 衢州市中通化工有限公司 | Preparation method for flame retardant expanded polystyrene with core-shell structure |
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2014
- 2014-12-24 CN CN201410820325.4A patent/CN104592942B/en active Active
Patent Citations (5)
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|---|---|---|---|---|
| CN101400756A (en) * | 2006-03-14 | 2009-04-01 | 旭硝子株式会社 | Working medium for heat cycle, rankine cycle system, heat pump cycle system, and refrigeration cycle system |
| CN102089400A (en) * | 2008-07-08 | 2011-06-08 | 纳幕尔杜邦公司 | Compositions comprising ionic liquids and fluoroolefins and use thereof in absorption cycle systems |
| CN103189466A (en) * | 2010-11-08 | 2013-07-03 | 赢创德固赛有限公司 | Working medium for absorption heat pumps |
| WO2014151344A1 (en) * | 2013-03-15 | 2014-09-25 | Honeywell International Inc. | Low gwp heat transfer compositions containing difluoromethane, a fluorinated ethane and 1,3,3,3-tetrafluoropropene |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105885080A (en) * | 2016-05-05 | 2016-08-24 | 巨化集团技术中心 | Foamer composition and preparation method thereof |
| JP2020511570A (en) * | 2017-03-06 | 2020-04-16 | アーケマ・インコーポレイテッド | Refrigerant with reduced flammability profile |
| CN107134592A (en) * | 2017-06-27 | 2017-09-05 | 山东大学 | A kind of fluoro ether electrolyte for lithium cells and preparation method thereof |
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| CN104592942B (en) | 2017-11-24 |
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