TW201022425A - 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
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- TW201022425A TW201022425A TW098134421A TW98134421A TW201022425A TW 201022425 A TW201022425 A TW 201022425A TW 098134421 A TW098134421 A TW 098134421A TW 98134421 A TW98134421 A TW 98134421A TW 201022425 A TW201022425 A TW 201022425A
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- composition
- gas
- acetate
- additional compound
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- 239000000203 mixture Substances 0.000 title claims abstract description 188
- 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 98
- 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 32
- 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 abstract description 7
- 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 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 144
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 139
- 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 105
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 103
- 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 57
- 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 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 51
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 49
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims abstract description 49
- -1 CF3CClFCH2OZnCl Chemical compound 0.000 claims abstract description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 23
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 21
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 21
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims abstract description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 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 11
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims abstract description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 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 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 4
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims abstract description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims description 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 26
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 claims description 24
- 239000011701 zinc Substances 0.000 claims description 22
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052725 zinc Inorganic materials 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 claims description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 8
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 claims description 8
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- XAKXZZPEUKNHMA-UHFFFAOYSA-N decyl decanoate Chemical compound CCCCCCCCCCOC(=O)CCCCCCCCC XAKXZZPEUKNHMA-UHFFFAOYSA-N 0.000 claims description 6
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- JOWBFITYYIZBFK-UHFFFAOYSA-N 2,2-bis(sulfanyl)acetamide Chemical compound NC(=O)C(S)S JOWBFITYYIZBFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005640 Methyl decanoate Substances 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004760 aramid Chemical class 0.000 claims description 3
- 229920003235 aromatic polyamide Chemical class 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims 4
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 2
- QBVHMPFSDVNFAY-UHFFFAOYSA-N 1,1,1-trifluorobutan-2-one Chemical compound CCC(=O)C(F)(F)F QBVHMPFSDVNFAY-UHFFFAOYSA-N 0.000 claims 1
- ILJXIWRDZSPWPF-UHFFFAOYSA-N 3,4-dimethyl-1H-indol-2-amine Chemical class CC1=C2C(=C(NC2=CC=C1)N)C ILJXIWRDZSPWPF-UHFFFAOYSA-N 0.000 claims 1
- QCDKDIDFDVVDLU-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC1=2)N1CCCCC1 Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC1=2)N1CCCCC1 QCDKDIDFDVVDLU-UHFFFAOYSA-N 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- NOIDGHWGILDJIP-UHFFFAOYSA-N P(=O)([O-])([O-])[O-].C(CCCCCCCCC)[PH3+].C(CCCCCCCCC)[PH3+].C(CCCCCCCCC)[PH3+] Chemical compound P(=O)([O-])([O-])[O-].C(CCCCCCCCC)[PH3+].C(CCCCCCCCC)[PH3+].C(CCCCCCCCC)[PH3+] NOIDGHWGILDJIP-UHFFFAOYSA-N 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- ZIYVAZASIRJRHP-UHFFFAOYSA-N acetonitrile;hydron;fluoride Chemical compound F.CC#N ZIYVAZASIRJRHP-UHFFFAOYSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 26
- 230000008569 process Effects 0.000 abstract description 9
- 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 abstract description 7
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract description 7
- 238000004378 air conditioning Methods 0.000 abstract description 5
- 238000005057 refrigeration Methods 0.000 abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 2
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical compound FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 abstract 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 65
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 55
- 229910052751 metal Inorganic materials 0.000 description 37
- 239000002184 metal Substances 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 35
- 239000007789 gas Substances 0.000 description 33
- 239000007791 liquid phase Substances 0.000 description 24
- 239000012535 impurity Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 150000001299 aldehydes Chemical class 0.000 description 15
- 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 13
- 230000002829 reductive effect Effects 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229930040373 Paraformaldehyde Natural products 0.000 description 11
- 229920002866 paraformaldehyde Polymers 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000012808 vapor phase Substances 0.000 description 10
- 239000007810 chemical reaction solvent Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000010354 integration Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- CAQPTDOAJUMIAI-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)C(F)(F)F CAQPTDOAJUMIAI-UHFFFAOYSA-N 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005906 dihydroxylation reaction Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229930182558 Sterol Natural products 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 150000003432 sterols Chemical class 0.000 description 4
- 235000003702 sterols Nutrition 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical group [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- 239000004246 zinc acetate Substances 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 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
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
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- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
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- 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
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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
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- 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 (1)
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| US10433408P | 2008-10-10 | 2008-10-10 |
Publications (1)
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| TW201022425A true TW201022425A (en) | 2010-06-16 |
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| TW (1) | TW201022425A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2010042781A2 (cg-RX-API-DMAC7.html) |
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| PT2634232T (pt) | 2008-05-07 | 2022-06-02 | Chemours Co Fc Llc | Composições |
| AU2009244263B2 (en) | 2008-05-07 | 2014-05-22 | The Chemours Company Fc, Llc. | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3- tetrafluoropropene |
| CA2736216A1 (en) | 2008-10-10 | 2010-04-15 | E. I. Du Pont De Nemours And Company | 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 |
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| US9321867B2 (en) | 2012-12-21 | 2016-04-26 | Honeywell International Inc. | Synthesis of 2,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers |
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| CN106029852B (zh) | 2014-02-20 | 2019-05-17 | Ａｇｃ株式会社 | 热循环系统用组合物以及热循环系统 |
| MY178665A (en) * | 2014-02-20 | 2020-10-20 | Asahi Glass Co Ltd | Composition for heat cycle system, and heat cycle system |
| CN106029850B (zh) * | 2014-02-20 | 2019-12-10 | Ａｇｃ株式会社 | 热循环系统用组合物以及热循环系统 |
| EP3109292B1 (en) * | 2014-02-20 | 2020-09-02 | AGC Inc. | Working fluid for heat cycle |
| WO2015125884A1 (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 |
| JP6540685B2 (ja) | 2014-02-28 | 2019-07-10 | Ａｇｃ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 |
| EP3115431A4 (en) * | 2014-03-06 | 2017-10-11 | Asahi Glass Company, Limited | Working medium for heat cycle, and heat cycle system |
| WO2015132963A1 (ja) * | 2014-03-07 | 2015-09-11 | 三菱電機株式会社 | 熱交換器及び空気調和機 |
| EP3118540A4 (en) * | 2014-03-14 | 2017-11-01 | Mitsubishi Electric Corporation | Refrigerating device |
| 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 |
| WO2015136980A1 (ja) * | 2014-03-14 | 2015-09-17 | 三菱電機株式会社 | 冷凍サイクル装置 |
| JPWO2015140878A1 (ja) * | 2014-03-17 | 2017-04-06 | 三菱電機株式会社 | アキュムレータ及び冷凍サイクル装置 |
| US20170121581A1 (en) * | 2014-03-17 | 2017-05-04 | Asahi Glass Company, Limited | Heat pump apparatus |
| JP6493388B2 (ja) | 2014-03-17 | 2019-04-03 | Ａｇｃ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 |
| EP3121538A1 (en) * | 2014-03-17 | 2017-01-25 | Mitsubishi Electric Corporation | Refrigeration cycle apparatus |
| WO2015140869A1 (ja) * | 2014-03-17 | 2015-09-24 | 三菱電機株式会社 | スクロール圧縮機 |
| US10101069B2 (en) * | 2014-03-17 | 2018-10-16 | Mitsubishi Electric Corporation | Refrigeration cycle apparatus |
| JP6524995B2 (ja) * | 2014-03-18 | 2019-06-05 | Ａｇｃ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 |
| BR112016020985B1 (pt) * | 2014-03-18 | 2022-09-20 | Agc Inc | Composição para sistema de ciclo de calor e sistema de ciclo de calor |
| ES2820350T3 (es) | 2014-09-25 | 2021-04-20 | Daikin Ind Ltd | Composición que comprende HFC y HFO |
| CN106796057B (zh) | 2014-10-16 | 2019-10-25 | 三菱电机株式会社 | 冷冻循环装置 |
| KR101908875B1 (ko) | 2014-10-16 | 2018-10-16 | 미쓰비시덴키 가부시키가이샤 | 냉동 사이클 장치 |
| GB201501598D0 (en) | 2015-01-30 | 2015-03-18 | Mexichem Fluor Sa De Cv | Compositions |
| KR101918435B1 (ko) | 2015-02-19 | 2018-11-13 | 다이킨 고교 가부시키가이샤 | 불소화 탄화수소의 혼합물을 함유하는 조성물 및 그 제조 방법 |
| CN107532073A (zh) * | 2015-05-12 | 2018-01-02 | 旭硝子株式会社 | 热循环系统用组合物以及热循环系统 |
| JP6848861B2 (ja) * | 2015-06-01 | 2021-03-24 | Ａｇｃ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 |
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| GB2582364A (en) * | 2019-03-21 | 2020-09-23 | Mexichem Fluor Sa De Cv | Methods |
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| CN116694305B (zh) * | 2022-02-28 | 2025-09-16 | 山东东岳未来氢能材料股份有限公司 | 含三氟乙酰氟的低gwp值组合物及其用途 |
| CN116098816A (zh) * | 2022-07-21 | 2023-05-12 | 北京市春立正达医疗器械股份有限公司 | 一种氟化防龋泡沫的制作方法 |
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| JP2011522772A (ja) | 2007-11-20 | 2011-08-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ヒドロフルオロアルカノールおよびヒドロフルオロアルケンの合成 |
| US8058488B2 (en) * | 2007-11-20 | 2011-11-15 | E. I. Du Pont De Nemours And Company | Synthesis of hydrofluoroalkanols and hydrofluoroalkenes |
| PT2634232T (pt) * | 2008-05-07 | 2022-06-02 | Chemours Co Fc Llc | Composições |
| AU2009244263B2 (en) * | 2008-05-07 | 2014-05-22 | The Chemours Company Fc, Llc. | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3- tetrafluoropropene |
| US20090325445A1 (en) * | 2008-06-27 | 2009-12-31 | Bogdan Mary C | Method of insulating temporary polymeric structures with polyurethane or polyisocyanurate foam |
| CA2736216A1 (en) | 2008-10-10 | 2010-04-15 | E. I. Du Pont De Nemours And Company | 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 |
| US20100172701A1 (en) * | 2008-12-12 | 2010-07-08 | Honeywell International Inc. | Barrier fortification enhancement and building structural units |
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2009
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- 2009-10-09 MX MX2011003633A patent/MX2011003633A/es active IP Right Grant
- 2009-10-09 US US12/576,388 patent/US8147710B2/en not_active Expired - Fee Related
- 2009-10-09 AU AU2009302263A patent/AU2009302263A1/en not_active Abandoned
- 2009-10-09 RU RU2011118429/04A patent/RU2011118429A/ru not_active Application Discontinuation
- 2009-10-09 CN CN2009801401143A patent/CN102177118A/zh active Pending
- 2009-10-09 KR KR1020117010557A patent/KR20110084910A/ko not_active Withdrawn
- 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 JP JP2011531192A patent/JP2012505296A/ja active Pending
- 2009-10-09 WO PCT/US2009/060094 patent/WO2010042781A2/en not_active Ceased
- 2009-10-09 TW TW098134421A patent/TW201022425A/zh unknown
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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 |
| KR20110084910A (ko) | 2011-07-26 |
| CA2736216A1 (en) | 2010-04-15 |
| US8147710B2 (en) | 2012-04-03 |
| JP2012505296A (ja) | 2012-03-01 |
| AU2009302263A1 (en) | 2010-04-15 |
| RU2011118429A (ru) | 2012-11-20 |
| BRPI0913806A2 (pt) | 2015-10-20 |
| US8518294B2 (en) | 2013-08-27 |
| MX2011003633A (es) | 2011-05-02 |
| EP2331489A2 (en) | 2011-06-15 |
| US20120168672A1 (en) | 2012-07-05 |
| CN102177118A (zh) | 2011-09-07 |
| WO2010042781A2 (en) | 2010-04-15 |
| US20100090156A1 (en) | 2010-04-15 |
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