CA2736216A1 - Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy)chloride - Google Patents
Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy)chloride Download PDFInfo
- Publication number
- CA2736216A1 CA2736216A1 CA2736216A CA2736216A CA2736216A1 CA 2736216 A1 CA2736216 A1 CA 2736216A1 CA 2736216 A CA2736216 A CA 2736216A CA 2736216 A CA2736216 A CA 2736216A CA 2736216 A1 CA2736216 A1 CA 2736216A1
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- hfo
- composition
- acetate
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 239000000203 mixture Substances 0.000 title claims abstract description 183
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 95
- ZGDAIZKZNKWBTM-UHFFFAOYSA-N 2-chloro-2,3,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(Cl)C(F)(F)F ZGDAIZKZNKWBTM-UHFFFAOYSA-N 0.000 title claims abstract description 42
- JXLLSNNXICBZIS-UHFFFAOYSA-N (2-chloro-2,3,3,3-tetrafluoropropyl) acetate Chemical compound CC(=O)OCC(F)(Cl)C(F)(F)F JXLLSNNXICBZIS-UHFFFAOYSA-N 0.000 title claims abstract description 33
- YZNCFBREKILROT-UHFFFAOYSA-N (2-chloro-2,3,3,3-tetrafluoropropyl) hypochlorite;zinc Chemical compound [Zn].FC(F)(F)C(F)(Cl)COCl YZNCFBREKILROT-UHFFFAOYSA-N 0.000 title claims abstract description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 167
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 129
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 111
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims abstract description 94
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 93
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 85
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims abstract description 69
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 59
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 50
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 claims abstract description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 45
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 41
- -1 CF3CHFCI) Chemical compound 0.000 claims abstract description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims abstract description 24
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 23
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 18
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 18
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims abstract description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- JQEQBVHLTKCNTI-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropyl acetate Chemical compound CC(=O)OCC(F)C(F)(F)F JQEQBVHLTKCNTI-UHFFFAOYSA-N 0.000 claims abstract description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 14
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 11
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 9
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims abstract description 8
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 7
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 7
- MFOQKYXGXHZFDL-UHFFFAOYSA-N 3,4,4,4-tetrafluorobutan-2-one Chemical compound CC(=O)C(F)C(F)(F)F MFOQKYXGXHZFDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- AOMUALOCHQKUCD-UHFFFAOYSA-N dodecyl 4-chloro-3-[[3-(4-methoxyphenyl)-3-oxopropanoyl]amino]benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(Cl)C(NC(=O)CC(=O)C=2C=CC(OC)=CC=2)=C1 AOMUALOCHQKUCD-UHFFFAOYSA-N 0.000 claims abstract description 5
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical compound FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- DASQIKOOFDJYKA-UHFFFAOYSA-N CCIF Chemical compound CCIF DASQIKOOFDJYKA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 89
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 18
- KEGQZXLRQSXPJU-UHFFFAOYSA-N 1,3-difluoro-1,3-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(F)CC(F)(C(F)(F)F)C1 KEGQZXLRQSXPJU-UHFFFAOYSA-N 0.000 claims description 15
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 claims description 8
- MRQDALCRZBHBEM-UHFFFAOYSA-N 3-chloro-3,4,4,4-tetrafluorobutan-2-one Chemical compound CC(=O)C(F)(Cl)C(F)(F)F MRQDALCRZBHBEM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003222 pyridines Chemical class 0.000 claims description 7
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- ILAUSMKPJVMSSC-UHFFFAOYSA-N (2-chloro-2,3,3,3-tetrafluoropropyl) formate Chemical compound FC(F)(F)C(F)(Cl)COC=O ILAUSMKPJVMSSC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 2
- WFLOTYSKFUPZQB-OWOJBTEDSA-N (e)-1,2-difluoroethene Chemical compound F\C=C\F WFLOTYSKFUPZQB-OWOJBTEDSA-N 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 28
- 230000008569 process Effects 0.000 abstract description 14
- 238000005057 refrigeration Methods 0.000 abstract description 8
- 238000004378 air conditioning Methods 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 description 62
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 55
- 229910052751 metal Inorganic materials 0.000 description 38
- 239000002184 metal Substances 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 36
- 239000007791 liquid phase Substances 0.000 description 26
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 18
- 239000011701 zinc Substances 0.000 description 18
- 229930040373 Paraformaldehyde Natural products 0.000 description 17
- 239000012535 impurity Substances 0.000 description 16
- 229920002866 paraformaldehyde Polymers 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 229910052725 zinc Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 239000012808 vapor phase Substances 0.000 description 11
- 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 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000007810 chemical reaction solvent Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 230000010354 integration Effects 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000008246 gaseous mixture Substances 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000004246 zinc acetate Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- CAQPTDOAJUMIAI-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)C(F)(F)F CAQPTDOAJUMIAI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 description 2
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 description 2
- VVLPGEFGTCIINI-UHFFFAOYSA-N 2,3,3-trifluoroprop-2-enyl acetate Chemical compound CC(=O)OCC(F)=C(F)F VVLPGEFGTCIINI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005796 dehydrofluorination reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DPPHNCGGFCAZGX-UHFFFAOYSA-N 1,1-difluorocyclobutane Chemical compound FC1(F)CCC1 DPPHNCGGFCAZGX-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- RQBSYMINZKITIR-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoropropan-1-ol Chemical compound OCC(Cl)C(F)(F)F RQBSYMINZKITIR-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical class [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- GIUIQFXYGQJOIZ-UHFFFAOYSA-M [Cl-].[Zn++].[O-]CC(F)(Cl)C(F)(F)F Chemical compound [Cl-].[Zn++].[O-]CC(F)(Cl)C(F)(F)F GIUIQFXYGQJOIZ-UHFFFAOYSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- 150000001930 cyclobutanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- QHNXEVRKFKHMRL-UHFFFAOYSA-N dimethylazanium;acetate Chemical compound CNC.CC(O)=O QHNXEVRKFKHMRL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
-
- 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
- C09K5/045—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 containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- 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
- C09K3/00—Materials not provided for elsewhere
- C09K3/14—Anti-slip materials; Abrasives
-
- 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
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10433408P | 2008-10-10 | 2008-10-10 | |
| US61/104,334 | 2008-10-10 | ||
| PCT/US2009/060094 WO2010042781A2 (en) | 2008-10-10 | 2009-10-09 | Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy) chloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2736216A1 true CA2736216A1 (en) | 2010-04-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2736216A Abandoned CA2736216A1 (en) | 2008-10-10 | 2009-10-09 | Compositions comprising 2,3,3,3-tetrafluoropropene, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoro-propyl acetate or zinc (2-chloro-2,3,3,3-tetrafluoropropoxy)chloride |
Country Status (12)
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|---|---|
| US (2) | US8147710B2 (OSRAM) |
| EP (1) | EP2331489A2 (OSRAM) |
| JP (1) | JP2012505296A (OSRAM) |
| KR (1) | KR20110084910A (OSRAM) |
| CN (1) | CN102177118A (OSRAM) |
| AU (1) | AU2009302263A1 (OSRAM) |
| BR (1) | BRPI0913806A2 (OSRAM) |
| CA (1) | CA2736216A1 (OSRAM) |
| MX (1) | MX2011003633A (OSRAM) |
| RU (1) | RU2011118429A (OSRAM) |
| TW (1) | TW201022425A (OSRAM) |
| WO (1) | WO2010042781A2 (OSRAM) |
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|---|---|---|---|---|
| MX2010012148A (es) | 2008-05-07 | 2010-12-06 | Du Pont | Composiciones que comprenden 2,3-dicloro-1,1,1-trifluoropropano, 2-cloro-1,1,1-trifluoropropeno, 2-cloro-1,1,1,2-tetrafluoropropano o 2,3,3,3-tetrafluoropropeno. |
| US8147709B2 (en) | 2008-05-07 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Compositions comprising 3,3,3-trifluoropropyne |
| CN102177118A (zh) | 2008-10-10 | 2011-09-07 | 纳幕尔杜邦公司 | 包含2,3,3,3-四氟丙烯、2-氯-2,3,3,3-四氟丙醇、乙酸2-氯-2,3,3,3-四氟丙酯或(2-氯-2,3,3,3-四氟丙氧基)氯化锌的组合物 |
| US9353302B2 (en) | 2010-08-13 | 2016-05-31 | Carrier Corporation | Fluorinated hydrocarbon composition |
| IT1406472B1 (it) | 2010-12-22 | 2014-02-28 | Nuovo Pignone Spa | Prova per similitudine di prestazione di compressore |
| EP3854860A1 (en) * | 2011-05-19 | 2021-07-28 | Agc Inc. | Working medium and heat-cycle system |
| US8845922B2 (en) * | 2011-12-20 | 2014-09-30 | Honeywell International Inc. | Compositions and use of vinylidene fluoride and blends thereof |
| CN102766022A (zh) * | 2012-08-09 | 2012-11-07 | 西安近代化学研究所 | 3，3，3-三氟丙醇的合成方法 |
| US9321867B2 (en) | 2012-12-21 | 2016-04-26 | Honeywell International Inc. | Synthesis of 2,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers |
| FR3000096B1 (fr) * | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| WO2014123120A1 (ja) * | 2013-02-05 | 2014-08-14 | 旭硝子株式会社 | ヒートポンプ用作動媒体およびヒートポンプシステム |
| WO2014159315A1 (en) * | 2013-03-14 | 2014-10-02 | Honeywell International Inc. | Compositions and methods comprising vinylidene fluoride |
| WO2014156743A1 (ja) * | 2013-03-28 | 2014-10-02 | 三菱電機株式会社 | スクロール圧縮機及びそれを備えた冷凍サイクル装置 |
| CN115160988B (zh) * | 2013-04-30 | 2024-05-14 | Ａｇｃ株式会社 | 包含三氟乙烯的组合物 |
| JP6384475B2 (ja) * | 2013-04-30 | 2018-09-05 | Ａｇｃ株式会社 | 熱サイクル用作動媒体 |
| BR112015031288B1 (pt) * | 2013-07-12 | 2021-10-13 | AGC Inc. | Fluido de trabalho para ciclo térmico, composição para sistema de ciclo térmico e sistema de ciclo térmico |
| GB2535383B (en) | 2013-07-30 | 2016-10-19 | Mexichem Amanco Holding Sa | Heat transfer compositions |
| WO2015115252A1 (ja) * | 2014-01-31 | 2015-08-06 | 旭硝子株式会社 | 熱サイクル用作動媒体、熱サイクルシステム用組成物および熱サイクルシステム |
| WO2015115551A1 (ja) * | 2014-01-31 | 2015-08-06 | 旭硝子株式会社 | 作動媒体の製造方法 |
| DE112015000583T5 (de) | 2014-01-31 | 2016-11-03 | Asahi Glass Company, Limited | Arbeitsfluid für einen Wärmekreisprozess, Zusammensetzung für ein Wärmekreisprozesssystem und Wärmekreisprozesssystem |
| EP3109302B1 (en) | 2014-02-20 | 2020-08-05 | AGC Inc. | Composition for heat cycle system, and heat cycle system |
| JP6520915B2 (ja) * | 2014-02-20 | 2019-05-29 | Ａｇｃ株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
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| WO2015125881A1 (ja) * | 2014-02-20 | 2015-08-27 | 旭硝子株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
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| WO2015136704A1 (ja) * | 2014-03-14 | 2015-09-17 | 三菱電機株式会社 | 圧縮機及び冷凍サイクル装置 |
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| CN101479219B (zh) * | 2006-06-27 | 2013-02-06 | 纳幕尔杜邦公司 | 四氟丙烯生产方法 |
| EP2066605B1 (en) * | 2006-09-05 | 2013-12-25 | E.I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
| WO2008030439A2 (en) * | 2006-09-05 | 2008-03-13 | E. I. Du Pont De Nemours And Company | Dehydrofluorination process to manufacture hydrofluoroolefins |
| CN101610987A (zh) * | 2006-10-31 | 2009-12-23 | 纳幕尔杜邦公司 | 含有2,3,3,3-四氟丙烯和/或1,2,3,3-四氟丙烯的组合物及其制备方法 |
| JP5321062B2 (ja) | 2006-11-01 | 2013-10-23 | ダイキン工業株式会社 | オレフィン類の製造方法 |
| GB0625214D0 (en) * | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| EP2592107A1 (en) | 2006-12-20 | 2013-05-15 | Honeywell International Inc. | Copolymers for barriers |
| US8058488B2 (en) | 2007-11-20 | 2011-11-15 | E. I. Du Pont De Nemours And Company | Synthesis of hydrofluoroalkanols and hydrofluoroalkenes |
| EP2215097A1 (en) | 2007-11-20 | 2010-08-11 | E. I. du Pont de Nemours and Company | Synthesis of hydrofluoroalkanols and hydrofluoroalkenes |
| MX2010012148A (es) * | 2008-05-07 | 2010-12-06 | Du Pont | Composiciones que comprenden 2,3-dicloro-1,1,1-trifluoropropano, 2-cloro-1,1,1-trifluoropropeno, 2-cloro-1,1,1,2-tetrafluoropropano o 2,3,3,3-tetrafluoropropeno. |
| US8147709B2 (en) * | 2008-05-07 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Compositions comprising 3,3,3-trifluoropropyne |
| US20090325445A1 (en) * | 2008-06-27 | 2009-12-31 | Bogdan Mary C | Method of insulating temporary polymeric structures with polyurethane or polyisocyanurate foam |
| CN102177118A (zh) | 2008-10-10 | 2011-09-07 | 纳幕尔杜邦公司 | 包含2,3,3,3-四氟丙烯、2-氯-2,3,3,3-四氟丙醇、乙酸2-氯-2,3,3,3-四氟丙酯或(2-氯-2,3,3,3-四氟丙氧基)氯化锌的组合物 |
| US20100172701A1 (en) * | 2008-12-12 | 2010-07-08 | Honeywell International Inc. | Barrier fortification enhancement and building structural units |
-
2009
- 2009-10-09 CN CN2009801401143A patent/CN102177118A/zh active Pending
- 2009-10-09 TW TW098134421A patent/TW201022425A/zh unknown
- 2009-10-09 MX MX2011003633A patent/MX2011003633A/es active IP Right Grant
- 2009-10-09 JP JP2011531192A patent/JP2012505296A/ja active Pending
- 2009-10-09 WO PCT/US2009/060094 patent/WO2010042781A2/en not_active Ceased
- 2009-10-09 RU RU2011118429/04A patent/RU2011118429A/ru not_active Application Discontinuation
- 2009-10-09 CA CA2736216A patent/CA2736216A1/en not_active Abandoned
- 2009-10-09 AU AU2009302263A patent/AU2009302263A1/en not_active Abandoned
- 2009-10-09 BR BRPI0913806A patent/BRPI0913806A2/pt not_active IP Right Cessation
- 2009-10-09 EP EP09748568A patent/EP2331489A2/en not_active Withdrawn
- 2009-10-09 KR KR1020117010557A patent/KR20110084910A/ko not_active Withdrawn
- 2009-10-09 US US12/576,388 patent/US8147710B2/en not_active Expired - Fee Related
-
2012
- 2012-02-27 US US13/405,657 patent/US8518294B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010042781A3 (en) | 2010-07-08 |
| JP2012505296A (ja) | 2012-03-01 |
| RU2011118429A (ru) | 2012-11-20 |
| MX2011003633A (es) | 2011-05-02 |
| AU2009302263A1 (en) | 2010-04-15 |
| KR20110084910A (ko) | 2011-07-26 |
| EP2331489A2 (en) | 2011-06-15 |
| US20120168672A1 (en) | 2012-07-05 |
| CN102177118A (zh) | 2011-09-07 |
| WO2010042781A2 (en) | 2010-04-15 |
| US8147710B2 (en) | 2012-04-03 |
| US20100090156A1 (en) | 2010-04-15 |
| TW201022425A (en) | 2010-06-16 |
| BRPI0913806A2 (pt) | 2015-10-20 |
| US8518294B2 (en) | 2013-08-27 |
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