JP6980771B2 - 1−クロロ−3,3,3−トリフルオロプロペンをベースにした組成物 - Google Patents
1−クロロ−3,3,3−トリフルオロプロペンをベースにした組成物 Download PDFInfo
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- JP6980771B2 JP6980771B2 JP2019515333A JP2019515333A JP6980771B2 JP 6980771 B2 JP6980771 B2 JP 6980771B2 JP 2019515333 A JP2019515333 A JP 2019515333A JP 2019515333 A JP2019515333 A JP 2019515333A JP 6980771 B2 JP6980771 B2 JP 6980771B2
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- 239000000203 mixture Substances 0.000 title claims description 210
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 title claims description 32
- 229920005862 polyol Polymers 0.000 claims description 85
- -1 polyol ester Chemical class 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000003507 refrigerant Substances 0.000 claims description 34
- 239000003381 stabilizer Substances 0.000 claims description 30
- 239000000314 lubricant Substances 0.000 claims description 26
- 150000003077 polyols Chemical class 0.000 claims description 26
- 239000012530 fluid Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 230000006835 compression Effects 0.000 claims description 17
- 238000007906 compression Methods 0.000 claims description 17
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 13
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 12
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 238000007710 freezing Methods 0.000 claims description 10
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 230000008014 freezing Effects 0.000 claims description 9
- 238000005057 refrigeration Methods 0.000 claims description 9
- 238000004378 air conditioning Methods 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 7
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 230000005611 electricity Effects 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000006520 cycloalkyl aryl alkyl group Chemical group 0.000 claims description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 2
- QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 claims 1
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 claims 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 description 18
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 17
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 16
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 13
- 150000002763 monocarboxylic acids Chemical class 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 229940059574 pentaerithrityl Drugs 0.000 description 11
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 10
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 9
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000013529 heat transfer fluid Substances 0.000 description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 6
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000000700 radioactive tracer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
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- 210000000056 organ Anatomy 0.000 description 3
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- 150000003573 thiols Chemical class 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 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 2
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 2
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 2
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- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
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- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 2
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
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- 150000008064 anhydrides Chemical class 0.000 description 2
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- 230000005540 biological transmission Effects 0.000 description 2
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- 238000002485 combustion reaction Methods 0.000 description 2
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- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
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- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C09K5/048—Boiling liquids as heat transfer materials
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
- F01D—NON-POSITIVE DISPLACEMENT MACHINES OR ENGINES, e.g. STEAM TURBINES
- F01D15/00—Adaptations of machines or engines for special use; Combinations of engines with devices driven thereby
- F01D15/10—Adaptations for driving, or combinations with, electric generators
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
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Description
本発明の一つの実施形態では、冷媒Fは少なくとも一種の安定剤化合物を含む。
(1)1−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233zd)と、二重結合を一つしか有しないC3−C6アルケンの安定剤化合物とを含む少なくとも一種の冷媒F、
(2)ポリオールエステル(POE)をベースにした少なくとも1種の潤滑剤。
− 1−ブテン(but-1-ene)
− シス−2−ブテン(cis-but-2-ene)
− トランス−2−ブテン
− 2−メチル−1−プロペン(2-methylprop-1-ene)
− 1−ペンテン
− シス−2−ペンテン
− トランス−2−ペンテン
− 2−メチル−1−ブテン(2-methylbut-1-ene)
− 2−メチル−2−ブテン
− 3−メチル−1−ブテン
(CH3)2C=CH−CH3(沸点39℃)
CH3−CH(CH3)−CH=CH2(沸点25℃)
本発明では、潤滑剤は一種または複数のポリオールのエステルで較正できる。一つの実施形態では、このポリオールエステルは少なくとも1種のポリオールとカルボン酸またはカルボン酸混合物とを反応させて得られる。
一つの実施形態では、本発明のポリオールエステルは下記式(I)に対応する:
R1[OC(O)R2]n (I)
(ここで、
R1は直鎖または分枝鎖の炭化水素基で、必要に応じて少なくとも1つのヒドロキシル基で置換されていてもよく、および/または、−O−、−N−および−S−からなる群から選択される少なくとも1つのヘテロ原子を含んでいてもよく、
各R2は下記i)〜iv)からなる群から互いに独立して選択され:
i) H、
ii) 脂肪族炭化水素基、
iii) 分岐鎖の炭化水素基、
iv) ii)および/またはiii)の基と8〜14個の炭素原子を有する脂肪族炭化水素基との混合物、
nは少なくとも2の整数である)
R1(OH)n (II)
(ここで、
R1は直鎖または分枝鎖の炭化水素基で、必要に応じて少なくとも1つ個のヒドロキシル基、好ましくは2つのヒドロキシル基で置換されていてもよく、および/または、−O−、−N−および−S−からなる群から選択される少なくとも1つのヘテロ原子を含むことができ、
nは2以上の整数である)
R2COOH (III)
(ここで、
R2は下記i)〜iv)からなる群から選択される:
i) H、
ii) 脂肪族炭化水素基、
iii) 分岐鎖の炭化水素基、
iv) ii)および/またはiii)の基と8〜14個の炭素原子を有する脂肪族炭化水素基との混合物)
好ましくは、R2は4〜20個、好ましくは5〜14個、好ましくは6〜8個の炭素原子を有する分岐鎖を有する炭化水素基である。
−C(R3)R4)(R5) (IV)
(ここで、
R3、R4およびR5は互いに独立してアルキル基であり、アルキル基の少なくとも一つは少なくとも2個の炭素原子を含む。これらの分枝鎖アルキル基はカルボキシル基と結合したときに「ネオ基、groupe neo」の名称で知られ、対応する酸はネオ酸(acide neo)とよばれる。R3およびR4はメチルで、R5は、少なくとも2個の炭素原子を含むアルキル基であるのが好ましい。
別の実施形態では、本発明のポリオールエステルは、最大で8個の炭素原子を有する1つまたは複数の分枝鎖カルボン酸の少なくとも一種のエステルを含む。このエステルは分枝鎖カルボン酸と1種または複数のポリオールとの反応で得られる。
i) 2−メチルブタン酸、3−メチルブタン酸およびこれらの混合物から選択されるカルボン酸、
ii)ネオペンチルグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール、トリペンタエリスリトールおよびこれらの混合物からなる群から選択されるポリオール。
ポリオールエステルは2−メチルブタン酸とジペンタエリスリトールとから得るのが好ましい。
ポリオールエステルは3−メチルブタン酸とペンタエリスリトールとから得るのが好ましい。
ポリオールエステルは3−メチルブタン酸とジペンタエリスリトールとから得るのが好ましい。
ポリオールエステルは2−メチルブタン酸とネオペンチルグリコールとから得るのが好ましい。
別の実施形態では、本発明のポリオールエステルは下記のi)とii)で得られるポリ(ネオペンチルポリオール)エステルである:
i) 下記式(V)を有するネオペンチルポリオール:
(ここで、
各Rは互いに独立してCH3、C2H5またはCH2OHであり、
pは1〜4の整数)
と、2〜15個の炭素原子を有する少なくとも一種のモノカルボン酸とを、酸触媒の存在下で、カルボキシル基とヒドロキシル基とのモル比を1:1以下にして反応させて、部分的にエステル化されたポリ(ネオペンチル)ポリオール組成物を形成し、
ii)i)の工程で得られたと部分的にエステル化されたポリ(ネオペンチル)ポリオール組成物を、2〜15個の炭素原子を有する他のカルボン酸と反応させて、最終的なポリ(ネオペンチルポリオール)エステルを得る。
R'C(O)OH (VII)
(ここで、
R'は直鎖または分枝鎖のC1−C12アルキル基、C6−C12アリール、C6−C30アラルキル基であり、好ましくは、R'はC4−C10アルキル基、好ましくはC5−C9アルキル基である。
i)45重量%〜55重量%のモノペンタエリスリトールのエステルと、2〜15個の炭素原子を有する少なくとも一種のモノカルボン酸、
ii)最大で13重量%のジペンタエリスリトールのエステルと、2〜15個の炭素原子を有する少なくとも1種のモノカルボン酸、
iii)最大で10重量%のトリペンタエリスリトールのエステルと、2〜15個の炭素原子を有する少なくとも1種のモノカルボン酸、
iv) 最大で25重量%のテトラエリトリトールおよび他のペンタエリスリトールオリゴマーのエステルと、2〜15個の炭素原子を有する少なくとも1種のモノカルボン酸。
R7、R8、R9、R10、R11およびR12は互いに独立してHまたはCH3であり、
a、b、c、y、xおよびzは互いに独立して整数であり、
a+x、b+yおよびc+zは互いに独立して1〜20の範囲の整数であり、
R13、R14およびR15は、互いに独立して、脂肪族または分岐鎖のアルキル基、アルケニル基、シクロアルキル基、アリール基、アルキルアリール基、アリールアルキル基、アリールシクロアルキル基、アルキルシクロアルキル基、シクロアルキルアルキルアルキル基、シクロアルキルアリール基、アルキルシクロアルキルアリール基、アルキルアリールシクロアルキル基、アリールシクロアルキルアルキル基、アリールアルキルシクロアルキル基、シクロアルキルアルキルアリール基およびシクロアルキルアリールアルキル基からなる群の中から選択され、
R13、R14およびR15は1〜17個の炭素原子を有し、必要に応じて置換されていてもよい)
R13COOH
R14COOH
R15COOH
(ここで、R13、R14およびR15は上記定義のもの)
さらに、カルボン酸の誘導体、例えば無水物、エステルおよびアシルハライドを使用することもできる。
(ここで、
R17とR18は、互いに独立して、HまたはCH3であり、
mおよびnの各々は互いに独立して整数であり、m+nは1〜10の範囲の整数であり、
R16とR19は互いに独立して、脂肪族または分枝鎖のアルキル、アルケニル、シクロアルキル、アリール、アルキルアリール、アリールアルキル、アリールシクロアルキル、シクロアルキルアルキル、アルキルシクロアルキル、シクロアルキルアリール、アルキルシクロアルキルアリール、アルキルアリールシクロアルキル、アリールシクロアルキルアルキル、アリールアルキルシクロアルキル、シクロアルキルアルキルアリールおよびシクロアルキルアリールアルキルなる群から選択され、
R16およびR19は1〜17個の炭素原子を有し、必要に応じて置換されていてもよい)
本発明の組成物における冷媒Fの質量割合は組成物の1〜5%、または組成物の5〜10%、または組成物の10〜15%、または組成物の15〜20%、または組成物の20〜25%。または組成物の25〜30%、または組成物の30〜35%、または組成物の35〜40%、または組成物の40〜45%、または組成物の45〜50%、または組成物の50〜55%、または組成物の55〜60%、または組成物の60〜65%、または組成物の65〜70%、または組成物の70〜75%、または組成物の75〜80%、または組成物の80〜85%、または組成物の85〜90%、または組成物の90〜95%、または組成物の95〜99%、または組成物の99〜99.5%、または組成物の99.5〜99.9%、または組成物の99.9%以上にすることができる。冷媒量Fの含有量は上記の複数の範囲内で変えることができ、例えば50〜55%と55〜60%で50〜60%にすることができる。
(1)1−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233zd)を含み、必要に応じて一つの二重結合のみを有する上記のC3−C6アルケン安定剤化合物をさらに含む冷媒F、
(2)少なくとも1種のポリオールエステル(POE)をベースにした潤滑剤、特に、上記(A)、(B)、(C)または(D)のポリオールエステル、特に、上記の式(I)、(VIII)または(XI)のポリオールエステルから選択される潤滑剤
(1)特にHCFO−1233zdの総重量に対してHCFO−1233zdEの質量割合が95%以上または99%以上または99.9%以上である、1−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233zd)と、2−メチル−2−エンブテン−および3−メチル−2−ブテンから選択される安定剤化合物とを含む冷媒F、
(2)上記式(I)のポリオールエステルをベースにしたて少なくとも一種の潤滑剤。
(1)1−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233zdの)を含む冷媒F、
(2)ポリオールエステル(POE)をベースにした少なくとも一種の潤滑剤、
(3)ナノ粒子、安定剤(本発明の安定剤化合物とは異なるもの)、界面活性剤、トレーサー剤、蛍光剤、臭化剤および可溶化剤から選択される少なくとも一種の添加剤。
本発明はさらに、蒸気圧縮回路中での熱伝達組成物としての上記組成物の使用にも関するものである。
本発明はさらに、熱伝達組成物として本発明組成物を収容した蒸気圧縮システムを含む設備(installation)の使用をベースにした熱伝達方法にも関するものである。この熱伝達方法は流体または物体の加熱または冷却方法にすることができる。
− 空調システム、または
− 冷凍システム、または、
− 冷凍システム、または、
− ヒートポンプシステム。
以下、本発明の実施例を示すが、本発明が以下の実施例に限定されるものではない。
熱安定性試験をASHRAE規格97−2007「冷媒システムで使用する材料の化学的安定性をテストするための密封ガラス管法(sealed glass tube method to test the chemical stability of materials for use within r饅ochfrig饅ochrant Systems)」に従って行った。
流体の質量(安定剤を含む):2g
潤滑剤の質量:5g
空気乾燥:0.2ミリモル
温度:180℃
期間:14日
下記の2つの商業用潤滑剤を試験した:
− PVE Bitzer32オイル(Bitzer/出光)、
− Solest 68オイル(CPI Engineering services inc)
冷媒Fは下記から成る:
2−メチル−2−ブテン 0.5重量%
HCFO−1233zd 99.5重量%
試験終了時に、気相を収集し、ガスクロマトグラフィーで分析した。主たる不純物はGC/MS(ガスクロマトグラフィーに質量分析を連結したもの)で同定した。
従って、この試験結果は、HFO−1233zd/POEオイル混合物の方がHFO−1233zd/PVEオイル混合物よりも熱的により安定であることを示している。
Claims (19)
- 冷媒Fと少なくとも1種のポリオールエステルをベースにした潤滑剤とを含む組成物であって、冷媒Fが1−クロロ−3,3,3−トリフルオロプロペンと、少なくとも一種の二重結合を一つしか有していないC3−C6アルケン安定化剤化合物とを含むことを特徴とする組成物。
- 安定剤化合物が1−ブテン、シス−2−ブテン、トランス−2−ブテン、2−メチル−1−プロペン、1−ペンテン、シス−2−ペンテン、トランス−2−ペンテン、2−メチル−1−ブテン、2−−メチル−2−ブテン、3−メチル−1−ブテンおよびこれらの混合物からなる群の中から選択される請求項1に記載の組成物。
- 安定剤化合物が2−メチル−2−ブテンおよび3−メチル−1−ブテンから選択される請求項1に記載の組成物。
- 1−クロロ−3,3,3−トリフルオロプロペンのトランス形態の重量割合が高く、90%以上である請求項1〜3のいずれかに記載の組成物。
- 1−クロロ−3,3,3−トリフルオロプロペンのトランス形態の重量割合が95%以上である請求項4に記載の組成物。
- 1−クロロ−3,3,3−トリフルオロプロペンのトランス形態の重量割合が99%以上である請求項5に記載の組成物。
- 1−クロロ−3,3,3−トリフルオロプロペンのトランス形態の重量割合が99.5%以上である請求項6に記載の組成物。
- 1−クロロ−3,3,3−トリフルオロプロペンのトランス形態の重量割合が99.9%以上である請求項7に記載の組成物。
- ポリオールエステルが下記の式(I)を有する請求項1〜8のいずれか一項に記載の組成物:
R1[OC(O)R2]n (I)
(ここで、
R1は直鎖または分枝鎖の炭化水素基で、必要に応じて少なくとも1つのヒドロキシル基で置換されていてもよく、および/または、−O−、−N−および−S−からなる群から選択される少なくとも1つのヘテロ原子を含んでいてもよく、
各R2は互いに独立して下記i)〜iv)からなる群から選択され:
i) H、
ii) 脂肪族炭化水素基、
iii) 分枝鎖の炭化水素基、
iv)ii)および/またはiii)の基と8〜14個の炭素原子を有する脂肪族炭化水素基との混合物、
nは2以上の整数) - ポリオールエステルが、ネオペンチルグリコール、グリセロール、トリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール、トリペンタエリスリトールおよびこれらの混合物からなる群から選択されるポリオールから得られる請求項1〜8のいずれか一項に記載の組成物。
- ポリオールエステルが、5〜8個の炭素原子を有する少なくとも一種の分枝鎖カルボン酸から得られる請求項1〜8,10のいずれか一項に記載の組成物。
- ポリオールエステルが下記の(i)と(ii)により得られたポリ(ネオペンチルポリオール)エステルである請求項1〜8のいずれかに記載の組成物:
(i) 下記式(V)を有するネオペンチルポリオール:
(ここで、
各Rは互いに独立してCH3、C2H5またはCH2OHであり、
pは1〜4の範囲の整数)
を2〜15個の炭素原子を有する少なくとも一種のモノカルボン酸と、酸触媒の存在下で、カルボキシル基とヒドロキシル基との間のモル比を1:1にして反応させて、部分的にエステル化したポリ(ネオペンチル)ポリオールの組成物を形成し、
(ii) (i)で得られた部分的にエステル化したポリ(ネオペンチル)ポリオールの組成物を2〜15個の炭素原子を有する他のカルボン酸と反応させて、ポリ(ネオペンチルポリオール)エステルの組成物を形成する。 - ポリオールエステルが下記の式(VIII)または(IX)を有する請求項1〜8のいずれかに記載の組成物:
(ここで、
R7、R8、R9、R10、R11およびR12は互いに独立してHまたはCH3であり、
a、b、c、y、xおよびzは互いに独立して整数であり、
a+x、b+yおよびc+zは互いに独立して1〜20の範囲の整数であり、
R13、R14およびR15は互いに独立して脂肪族または分岐鎖のアルキル基、アルケニル基、シクロアルキル基、アリール基、アルキルアリール基、アリールアルキル基、アルキルシクロアルキル基、シクロアルキルアルキル基、アリールシクロアルキル基、シクロアルキルアリール基、アルキルシクロアルキルアリール基、アルキルアリールシクロアルキル基、アリールシクロアルキルアルキル基、アリールアルキルシクロアルキル基、シクロアルキルアルキルアリール基およびシクロアルキルアリールアルキル基から選択され、
R13、R14およびR15は1〜17個の炭素原子を有し、必要に応じて置換されていてもよい)、または、
(ここで、
R17およびR18のそれぞれは互いに独立してHまたはCH3であり、
mおよびnの各々は互いに独立して整数であり、m+nは1〜10の範囲の整数であり、
R16およびR19は互いに独立して脂肪族または分枝鎖のアルキル基、アルケニル、シクロアルキル、アリール、アルキルアリール、アリールアルキル、アルキルシクロアルキル、シクロアルキルアルキル、アリールシクロアルキル、シクロアルキルアリール、アルキルシクロアルキルアリール、アルキルアリールシクロアルキル、アリールシクロアルキルアルキル、アリールアルキルシクロアルキル、シクロアルキルアルキルアリールおよびシクロアルキルアリールアルキルからなる群から選択され、
R16およびR19は1〜17個の炭素原子を有し、必要に応じて置換されていてもよい) - 潤滑剤の含有量が組成物の10重量%〜50重量%である請求項1〜13のいずれか一項に記載の組成物。
- 請求項1〜14のいずれか一項に記載の組成物の、蒸気圧縮システムまたは熱機関における伝熱組成物としての使用。
- 請求項1〜14のいずれか一項に記載の組成物を伝熱組成物として収容した回路を有する伝熱設備。
- ヒートポンプ、空調、冷蔵、冷凍および熱機関から選択される可動式または固定式の請求項16に記載の設備。
- 組成物の蒸発、電気を生成するタービン内での熱伝達組成物の膨張、熱伝達組成物の凝縮および熱伝達組成物の圧縮を連続して行う、熱機関を使用して電気を発生させる方法であって、伝達組成物熱が請求項1〜14のいずれか一項に記載の組成物であることを特徴とする方法。
- 熱伝達組成物の蒸発、熱伝達組成物の圧縮、熱伝達組成物の凝縮、熱伝達組成物の膨張を連続して含む、伝熱組成物を収容した蒸気圧縮システムによって流体または物体を加熱または冷却する方法であって、伝熱組成物が請求項1〜14のいずれか一項に記載の組成物であることを特徴とする方法。
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PCT/FR2017/052473 WO2018051036A1 (fr) | 2016-09-19 | 2017-09-15 | Composition a base de 1-chloro-3,3,3-trifluoropropene |
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CA3036255A1 (fr) | 2018-03-22 |
JP2019535841A (ja) | 2019-12-12 |
WO2018051036A1 (fr) | 2018-03-22 |
CN109790445B (zh) | 2021-05-04 |
PL3516007T3 (pl) | 2022-03-28 |
PT3516007T (pt) | 2022-03-18 |
ES2907559T3 (es) | 2022-04-25 |
EP3516007A1 (fr) | 2019-07-31 |
EP3516007B1 (fr) | 2022-01-05 |
KR20190054116A (ko) | 2019-05-21 |
KR102477083B1 (ko) | 2022-12-13 |
US10669465B2 (en) | 2020-06-02 |
MX2019003081A (es) | 2019-08-05 |
FR3056222B1 (fr) | 2020-01-10 |
US20190276721A1 (en) | 2019-09-12 |
CN109790445A (zh) | 2019-05-21 |
DK3516007T3 (da) | 2022-02-28 |
FR3056222A1 (fr) | 2018-03-23 |
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