ES2968665T3 - Métodos - Google Patents
Métodos Download PDFInfo
- Publication number
- ES2968665T3 ES2968665T3 ES18724304T ES18724304T ES2968665T3 ES 2968665 T3 ES2968665 T3 ES 2968665T3 ES 18724304 T ES18724304 T ES 18724304T ES 18724304 T ES18724304 T ES 18724304T ES 2968665 T3 ES2968665 T3 ES 2968665T3
- Authority
- ES
- Spain
- Prior art keywords
- bromo
- tetrafluoro
- epoxypropane
- acetoxy
- tetrafluoropropane
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- SDKKMHPZNMQINR-UHFFFAOYSA-N 2-bromo-2,3,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(Br)C(F)(F)F SDKKMHPZNMQINR-UHFFFAOYSA-N 0.000 claims abstract description 31
- DHGQMHOMRCABJL-UHFFFAOYSA-N 2-fluoro-2-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1(F)CO1 DHGQMHOMRCABJL-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229920000570 polyether Polymers 0.000 claims abstract description 25
- WHQSIJLVZPYDHV-UHFFFAOYSA-N 2,2,3-trifluoro-3-(fluoromethyl)oxirane Chemical compound FCC1(F)OC1(F)F WHQSIJLVZPYDHV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims abstract description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 5
- MEMJQHNXLOXWQO-UHFFFAOYSA-N (2-bromo-2,3,3,3-tetrafluoropropyl) acetate Chemical compound C(C)(=O)OCC(C(F)(F)F)(F)Br MEMJQHNXLOXWQO-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 38
- -1 for example Substances 0.000 claims description 36
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- ULFHADFFJVZYKF-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)oxirane Chemical compound FC1OC1C(F)(F)F ULFHADFFJVZYKF-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 239000000314 lubricant Substances 0.000 claims description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- FONKJLQHHCWWSK-UHFFFAOYSA-N (2-bromo-1,3,3,3-tetrafluoropropyl) acetate Chemical compound C(C)(=O)OC(C(C(F)(F)F)Br)F FONKJLQHHCWWSK-UHFFFAOYSA-N 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- XVRNDNQEYALDCP-UHFFFAOYSA-N 2-bromo-1,3,3,3-tetrafluoropropan-1-ol Chemical compound BrC(C(F)(F)F)C(O)F XVRNDNQEYALDCP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910001510 metal chloride Inorganic materials 0.000 claims description 2
- 229910001512 metal fluoride Inorganic materials 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229960005235 piperonyl butoxide Drugs 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000007269 dehydrobromination reaction Methods 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- FJNZCBUVTKMTNI-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoropropan-1-ol Chemical compound OCC(Br)C(F)(F)F FJNZCBUVTKMTNI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000036983 biotransformation Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SOLYBTULJSCJLK-UHFFFAOYSA-N (2-bromo-3,3,3-trifluoropropyl) acetate Chemical compound CC(=O)OCC(Br)C(F)(F)F SOLYBTULJSCJLK-UHFFFAOYSA-N 0.000 description 1
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 description 1
- UIRCFIKJTSKUQM-UHFFFAOYSA-N 1-bromo-1-fluoropropan-1-ol Chemical group BrC(CC)(O)F UIRCFIKJTSKUQM-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- AQZRARFZZMGLHL-UHFFFAOYSA-N 2-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1CO1 AQZRARFZZMGLHL-UHFFFAOYSA-N 0.000 description 1
- ZRRFBWAUWDBNFH-UHFFFAOYSA-N 2-bromo-2,3,3,3-tetrafluoropropan-1-ol 2-fluoro-2-(trifluoromethyl)oxirane Chemical compound FC1(CO1)C(F)(F)F.BrC(C(F)(F)F)(CO)F ZRRFBWAUWDBNFH-UHFFFAOYSA-N 0.000 description 1
- QKBKGNDTLQFSEU-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Br)=C QKBKGNDTLQFSEU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UGLNYSQPQPOJPX-UHFFFAOYSA-N 3-bromo-1,1,2,2-tetrafluoropropan-1-ol Chemical compound BrCC(C(O)(F)F)(F)F UGLNYSQPQPOJPX-UHFFFAOYSA-N 0.000 description 1
- XDBLVWVZOHFZOV-UHFFFAOYSA-N BrC(C(F)(F)F)(CO)F.C(C)(=O)OCC(C(F)(F)F)(F)Br Chemical compound BrC(C(F)(F)F)(CO)F.C(C)(=O)OCC(C(F)(F)F)(F)Br XDBLVWVZOHFZOV-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 108010001202 Cytochrome P-450 CYP2E1 Proteins 0.000 description 1
- 102100024889 Cytochrome P450 2E1 Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000002739 cryptand Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/38—Lubricating compositions characterised by the base-material being a macromolecular compound containing halogen
-
- 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
- C10M147/00—Lubricating compositions characterised by the additive being a macromolecular compound containing halogen
- C10M147/04—Monomer containing carbon, hydrogen, halogen and oxygen
-
- 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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
- C10M2213/043—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Lubricants (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1706721.6A GB201706721D0 (en) | 2017-04-27 | 2017-04-27 | Methods |
| PCT/GB2018/051124 WO2018197897A1 (en) | 2017-04-27 | 2018-04-27 | Methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2968665T3 true ES2968665T3 (es) | 2024-05-13 |
Family
ID=59011195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES18724304T Active ES2968665T3 (es) | 2017-04-27 | 2018-04-27 | Métodos |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US11377432B2 (https=) |
| EP (1) | EP3615520B1 (https=) |
| JP (3) | JP7556689B2 (https=) |
| KR (1) | KR20190141680A (https=) |
| CN (1) | CN110546142B (https=) |
| DK (1) | DK3615520T3 (https=) |
| ES (1) | ES2968665T3 (https=) |
| GB (1) | GB201706721D0 (https=) |
| WO (1) | WO2018197897A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113423759B (zh) * | 2018-12-21 | 2023-12-29 | 墨西哥氟石股份公司 | 卤化聚醚的组合物 |
| GB2582364A (en) * | 2019-03-21 | 2020-09-23 | Mexichem Fluor Sa De Cv | Methods |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356291A (en) | 1981-04-03 | 1982-10-26 | E. I. Du Pont De Nemours And Company | Purification and polymerization of hexafluoropropylene oxide |
| JPH0625403A (ja) * | 1992-05-11 | 1994-02-01 | Japan Energy Corp | 含フッ素エーテルオリゴマー及びその製造方法 |
| JPH05310909A (ja) * | 1992-05-11 | 1993-11-22 | Japan Energy Corp | 含フッ素共重合体の製造方法 |
| JPH09110980A (ja) | 1995-10-13 | 1997-04-28 | Japan Energy Corp | トリフルオロプロピレンオキシド重合体の製造方法 |
| JPH09286853A (ja) * | 1996-04-23 | 1997-11-04 | Kao Corp | 含フッ素ポリエーテルの製造方法 |
| AU4811800A (en) * | 1999-05-04 | 2000-11-17 | E.I. Du Pont De Nemours And Company | Polyfluorinated epoxides and associated polymers and processes |
| DE19942534A1 (de) * | 1999-09-07 | 2001-03-08 | Henkel Ecolab Gmbh & Co Ohg | Fluorhaltige Schmiermittel |
| EP1655358A1 (de) * | 2004-11-04 | 2006-05-10 | Solvay Fluor GmbH | Arbeitsfluid zur Wärmeübertragung |
| EP1698650A1 (en) | 2005-03-02 | 2006-09-06 | 3M Innovative Properties Company | Polymerization of hexafluoropropylene oxide |
| WO2007105653A1 (ja) * | 2006-03-10 | 2007-09-20 | Asahi Glass Co., Ltd. | 含フッ素エポキシ化合物の開環重合による含フッ素重合体の製造方法 |
| US7456324B2 (en) | 2006-06-02 | 2008-11-25 | Great Lakes Chemical Corp. | Methods for preparing halohydrins and methods for preparing epoxides |
| JP5051445B2 (ja) | 2007-10-17 | 2012-10-17 | 株式会社ジェイテクト | 転がり軸受装置および主軸装置 |
| US7780345B2 (en) * | 2007-12-19 | 2010-08-24 | Motorola, Inc. | Method and apparatus for a temperature sensor for measuring peak temperatures |
| KR101067027B1 (ko) * | 2009-03-06 | 2011-09-23 | 한국화학연구원 | 헥사플루오로프로필렌 옥사이드 중합체 조성물 및 헥사플루오로프로필렌 올리고머를 활용한 헥사플루오로프로필렌 옥사이드 중합체의 제조방법 |
| EP3205649B1 (en) | 2014-11-21 | 2021-02-24 | Daikin Industries, Ltd. | Fluorinated unsaturated cyclic carbonate and process for producing the same |
| CN107709566B (zh) * | 2015-06-25 | 2021-06-08 | 中央硝子株式会社 | 光学活性含氟烷基环氧乙烷的工业制造方法 |
-
2017
- 2017-04-27 GB GBGB1706721.6A patent/GB201706721D0/en not_active Ceased
-
2018
- 2018-04-27 WO PCT/GB2018/051124 patent/WO2018197897A1/en not_active Ceased
- 2018-04-27 JP JP2019558540A patent/JP7556689B2/ja active Active
- 2018-04-27 ES ES18724304T patent/ES2968665T3/es active Active
- 2018-04-27 EP EP18724304.3A patent/EP3615520B1/en active Active
- 2018-04-27 KR KR1020197031470A patent/KR20190141680A/ko not_active Ceased
- 2018-04-27 DK DK18724304.3T patent/DK3615520T3/da active
- 2018-04-27 US US16/608,149 patent/US11377432B2/en active Active
- 2018-04-27 CN CN201880027469.0A patent/CN110546142B/zh active Active
-
2022
- 2022-06-01 US US17/829,598 patent/US11718597B2/en active Active
- 2022-11-17 JP JP2022184113A patent/JP2023015328A/ja active Pending
-
2024
- 2024-05-21 JP JP2024082704A patent/JP2024112914A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3615520B1 (en) | 2023-11-15 |
| US20220289701A1 (en) | 2022-09-15 |
| US11377432B2 (en) | 2022-07-05 |
| WO2018197897A1 (en) | 2018-11-01 |
| JP2023015328A (ja) | 2023-01-31 |
| CN110546142A (zh) | 2019-12-06 |
| DK3615520T3 (en) | 2023-11-27 |
| KR20190141680A (ko) | 2019-12-24 |
| JP2020517717A (ja) | 2020-06-18 |
| GB201706721D0 (en) | 2017-06-14 |
| JP2024112914A (ja) | 2024-08-21 |
| CN110546142B (zh) | 2023-09-05 |
| US20200148654A1 (en) | 2020-05-14 |
| US11718597B2 (en) | 2023-08-08 |
| JP7556689B2 (ja) | 2024-09-26 |
| EP3615520A1 (en) | 2020-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5093972B2 (ja) | フルオロオレフィンの製造方法 | |
| EP3872059B1 (en) | Process for the preparation of 2,3,3,3 tetrahydrofluoropropene | |
| KR101868766B1 (ko) | 1-클로로-2,3,3-트리플루오로프로펜의 제조 방법 | |
| JP5056946B2 (ja) | ２，３，３，３−テトラフルオロプロペンの製造方法 | |
| JP2024112914A (ja) | 方法 | |
| JP6892430B2 (ja) | （ペル）フルオロポリエーテルアミンの合成のための方法 | |
| TW202033481A (zh) | 環丁烯之製造方法 | |
| EP2321240B1 (fr) | Procede de preparation de composes fluores olefiniques | |
| JP2008308424A (ja) | ポリグリセリルエーテル誘導体 | |
| JP7576036B2 (ja) | パーフルオロ（２，４－ジメチル－２－フルオロホルミル－１，３－ジオキソラン）の製造方法 | |
| US11555024B2 (en) | Aldehyde adduct of hexafluoropropylene oxide, method of manufacturing trifluoropyruvyl fluoride dimer and method of manufacturing perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) | |
| JP2016530249A (ja) | −ｏｓｆ５基を含有するフッ素化化合物およびそれらの製造方法 | |
| EP3848359B1 (en) | Method for producing trifluoropyruvate fluoride dimer, and method for producing perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) | |
| KR102446846B1 (ko) | 불화알킬글리세린 유도체, 이의 제조방법 및 용도 | |
| Galimberti et al. | New catalytic alkylation of in situ generated perfluoro-alkyloxy-anions and perfluoro-carbanions | |
| JP4009724B2 (ja) | 含フッ素エーテル化合物の製造方法 | |
| JP2022528745A (ja) | １，２－ビス（ペルフルオロアルキル）エチレンのルイス酸触媒合成 | |
| JP4290093B2 (ja) | 含フッ素エーテル化合物の製造方法 | |
| RU2230057C1 (ru) | Способ получения фторангидридов полифторированных алкоксипропионовых кислот | |
| US7772443B2 (en) | Iodine-containing fluoropolyether and process for producing the same | |
| JP2018506572A (ja) | ジヨードペルフルオロ−ｃ３〜ｃ７−アルカンの段階的合成 | |
| JP5517202B2 (ja) | 含フッ素オキセタン化合物の製造方法 | |
| JP2015196680A (ja) | （ポリ）アルキレングリコールジアルキルエーテルの製造方法 | |
| US20180258017A1 (en) | Process for producing a fluorinated alkene | |
| HK1167384A (en) | Processes for reducing the amount of monofluoroacetate in hydrofluoroolefin production |