KR102499303B1 - 프로페닐아민 및 이의 제조 및 사용 방법 - Google Patents
프로페닐아민 및 이의 제조 및 사용 방법 Download PDFInfo
- Publication number
- KR102499303B1 KR102499303B1 KR1020197007494A KR20197007494A KR102499303B1 KR 102499303 B1 KR102499303 B1 KR 102499303B1 KR 1020197007494 A KR1020197007494 A KR 1020197007494A KR 20197007494 A KR20197007494 A KR 20197007494A KR 102499303 B1 KR102499303 B1 KR 102499303B1
- Authority
- KR
- South Korea
- Prior art keywords
- propenylamine
- composition
- perfluorinated
- isomer
- working fluid
- 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.)
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- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical compound CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims description 48
- 239000000203 mixture Substances 0.000 claims abstract description 139
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 7
- 239000012530 fluid Substances 0.000 claims description 63
- 238000006317 isomerization reaction Methods 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000012546 transfer Methods 0.000 claims description 25
- 230000007246 mechanism Effects 0.000 claims description 21
- 230000003197 catalytic effect Effects 0.000 claims description 16
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 14
- 239000013529 heat transfer fluid Substances 0.000 claims description 11
- 229910018287 SbF 5 Inorganic materials 0.000 claims description 9
- 229910019800 NbF 5 Inorganic materials 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910004529 TaF 5 Inorganic materials 0.000 claims description 4
- -1 perfluoro Chemical group 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000002904 solvent Substances 0.000 description 28
- 238000004140 cleaning Methods 0.000 description 24
- 239000003792 electrolyte Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- 239000000758 substrate Substances 0.000 description 22
- 239000004094 surface-active agent Substances 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
- 239000004604 Blowing Agent Substances 0.000 description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000000463 material Substances 0.000 description 17
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- 239000007788 liquid Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000001336 alkenes Chemical group 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 150000001450 anions Chemical class 0.000 description 10
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 10
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
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- 238000004293 19F NMR spectroscopy Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 239000002841 Lewis acid Substances 0.000 description 8
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 6
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- 239000010702 perfluoropolyether Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- AMLFJZRZIOZGPW-NSCUHMNNSA-N (e)-prop-1-en-1-amine Chemical compound C\C=C\N AMLFJZRZIOZGPW-NSCUHMNNSA-N 0.000 description 5
- BKDDXPKSQTVDCP-UHFFFAOYSA-N 1,1,2,3,3-pentafluoro-n,n-bis(trifluoromethyl)prop-2-en-1-amine Chemical compound FC(F)=C(F)C(F)(F)N(C(F)(F)F)C(F)(F)F BKDDXPKSQTVDCP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 239000011521 glass Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000012263 liquid product Substances 0.000 description 5
- 239000002667 nucleating agent Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229920001774 Perfluoroether Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000003570 air Substances 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical class ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052752 metalloid Inorganic materials 0.000 description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
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- 229920006362 Teflon® Polymers 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 3
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- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- NDULPSIUKNSNQT-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoro-N-(1,1,2,2,3,3,3-heptafluoropropyl)-N-(1,1,2,3,3-pentafluoroprop-2-enyl)propan-1-amine Chemical compound FC(C(=C(F)F)F)(N(C(C(C(F)(F)F)(F)F)(F)F)C(C(C(F)(F)F)(F)F)(F)F)F NDULPSIUKNSNQT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- RUWWEFDXKHVRBL-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,2,3,3-pentafluoroprop-2-enyl)morpholine Chemical compound FC(F)=C(F)C(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F RUWWEFDXKHVRBL-UHFFFAOYSA-N 0.000 description 2
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- HWINZWCWLOVBIS-UPHRSURJSA-N 2,2,3,3,5,5,6,6-octafluoro-4-[(e)-1,2,3,3,3-pentafluoroprop-1-enyl]morpholine Chemical compound FC(F)(F)C(\F)=C(/F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F HWINZWCWLOVBIS-UPHRSURJSA-N 0.000 description 2
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- 231100000053 low toxicity Toxicity 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/24—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
- F01K—STEAM ENGINE PLANTS; STEAM ACCUMULATORS; ENGINE PLANTS NOT OTHERWISE PROVIDED FOR; ENGINES USING SPECIAL WORKING FLUIDS OR CYCLES
- F01K25/00—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for
- F01K25/08—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for using special vapours
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/04—Auxiliary arrangements, e.g. for control of pressure or for circulation of fluids
- H01M8/04007—Auxiliary arrangements, e.g. for control of pressure or for circulation of fluids related to heat exchange
- H01M8/04029—Heat exchange using liquids
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/04—Auxiliary arrangements, e.g. for control of pressure or for circulation of fluids
- H01M8/04298—Processes for controlling fuel cells or fuel cell systems
- H01M8/04694—Processes for controlling fuel cells or fuel cell systems characterised by variables to be controlled
- H01M8/04701—Temperature
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K7/00—Constructional details common to different types of electric apparatus
- H05K7/20—Modifications to facilitate cooling, ventilating, or heating
- H05K7/20218—Modifications to facilitate cooling, ventilating, or heating using a liquid coolant without phase change in electronic enclosures
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Combustion & Propulsion (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| US201662377879P | 2016-08-22 | 2016-08-22 | |
| US62/377,879 | 2016-08-22 | ||
| PCT/US2017/047720 WO2018039096A1 (en) | 2016-08-22 | 2017-08-21 | Propenylamines and methods of making and using same |
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| Publication Number | Publication Date |
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| KR20190040979A KR20190040979A (ko) | 2019-04-19 |
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| CN (1) | CN109641819B (enExample) |
| WO (1) | WO2018039096A1 (enExample) |
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| KR102739483B1 (ko) | 2017-12-13 | 2024-12-05 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 하이드로플루오로올레핀 에테르, 조성물, 장치 및 이의 사용 방법 |
| US11551827B2 (en) | 2017-12-13 | 2023-01-10 | 3M Innovative Properties Company | Perfluorinated 1-alkoxypropenes in dielectric fluids and electrical devices |
| WO2019220293A1 (en) | 2018-05-15 | 2019-11-21 | 3M Innovative Properties Company | Perfluoroaminoolefins and methods of making and using the same |
| EP3900502A4 (en) | 2018-12-21 | 2022-11-02 | Honeywell International Inc. | HEAT TRANSFER PROCESSES, SYSTEMS AND FLUIDS |
| US20230247795A1 (en) | 2022-01-28 | 2023-08-03 | The Research Foundation For The State University Of New York | Regenerative preheater for phase change cooling applications |
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| US3000979A (en) | 1958-11-12 | 1961-09-19 | Du Pont | Isomerization of fluoroolefins |
| JPS647445A (en) | 1987-06-30 | 1989-01-11 | Nissin Electric Co Ltd | Gas-blast circuit-breaker |
| US4985556A (en) | 1987-09-10 | 1991-01-15 | Agency Of Industrial Science & Technology | Perfluoro(dialkylaminopropene) derivatives |
| JPS6470444A (en) | 1987-09-10 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| JPH0170445U (enExample) | 1987-10-28 | 1989-05-10 | ||
| JPS6470445A (en) * | 1988-07-23 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
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| EP1234261A4 (en) | 1999-07-07 | 2003-02-19 | Michael T Rossides | METHODS AND SYSTEMS FOR DETERMINING THE EXPECTED VALUE FOR PAYMENT AND VALUATION PURPOSES |
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| JP4458514B2 (ja) * | 2002-07-18 | 2010-04-28 | 第一三共株式会社 | 高純度のエナミン類の製造方法 |
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| US20070191506A1 (en) | 2006-02-13 | 2007-08-16 | 3M Innovative Properties Company | Curable compositions for optical articles |
| EP2035519B1 (en) | 2006-06-20 | 2016-12-21 | 3M Innovative Properties Company | Adhesive compositions, adhesive articles and methods for making the same |
| US7553999B2 (en) * | 2006-12-14 | 2009-06-30 | Chevron U.S.A. Inc. | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
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| US8361632B2 (en) | 2008-10-03 | 2013-01-29 | 3M Innovative Properties Company | Cloud point-resistant adhesives and laminates |
| US8361633B2 (en) | 2008-10-03 | 2013-01-29 | 3M Innovative Properties Company | Cloud point-resistant adhesives and laminates |
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| JP2011184582A (ja) | 2010-03-09 | 2011-09-22 | Three M Innovative Properties Co | 光学用粘着シート |
| US8426655B2 (en) | 2010-03-26 | 2013-04-23 | Honeywell International Inc. | Process for the manufacture of hexafluoro-2-butene |
| KR20130130698A (ko) | 2010-08-18 | 2013-12-02 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 응력 제거 광학 접착제를 포함하는 광학 조립체 및 그의 제조 방법 |
| CN108831587A (zh) | 2012-04-04 | 2018-11-16 | 3M创新有限公司 | 作为电介质气体的氟化腈 |
| WO2013161812A1 (ja) | 2012-04-27 | 2013-10-31 | 荒川化学工業株式会社 | 紫外線硬化型粘着剤組成物及び粘着層 |
| CN104520337B (zh) | 2012-05-29 | 2017-09-29 | 3M创新有限公司 | 液体光学粘合剂组合物 |
| CN107641486B (zh) | 2012-11-16 | 2021-04-02 | 3M创新有限公司 | 包含(甲基)丙烯酰基侧基的粘合剂、制品和方法 |
| KR20150095746A (ko) | 2012-12-10 | 2015-08-21 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 액체 광학 접착제 조성물 |
| EP3024810B1 (en) | 2013-07-25 | 2018-06-20 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of making same |
| EP3071613A1 (en) | 2013-11-21 | 2016-09-28 | 3M Innovative Properties Company | Liquid optical adhesive compositions |
| US9957428B2 (en) * | 2013-12-20 | 2018-05-01 | 3M Innovative Properties Company | Fluorinated olefins as working fluids and methods of using same |
| US9708236B2 (en) * | 2014-01-09 | 2017-07-18 | San Diego State University Research Foundation | Terminal alkene monoisomerization catalysts and methods |
| WO2015133517A1 (ja) | 2014-03-05 | 2015-09-11 | Jnc株式会社 | コーティング剤、硬化膜、積層体、成形物 |
| US10030185B2 (en) * | 2014-07-16 | 2018-07-24 | 3M Innovative Properties Company | Hydrofluoroether olefins and methods of using same |
| KR20170099923A (ko) | 2014-12-05 | 2017-09-01 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 시럽 중합체 조성물 및 그로부터의 접착제 |
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| US10738001B2 (en) * | 2015-06-05 | 2020-08-11 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
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2017
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- 2017-08-21 EP EP17844197.8A patent/EP3500546B1/en active Active
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- 2017-08-21 JP JP2019510608A patent/JP7076886B2/ja active Active
- 2017-08-21 KR KR1020197007494A patent/KR102499303B1/ko active Active
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2022
- 2022-07-27 US US17/874,851 patent/US11858875B2/en active Active
Non-Patent Citations (1)
| Title |
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| 비특허: J. Chem. Soc. Perkin Trans. (1975) |
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| EP3500546B1 (en) | 2021-02-24 |
| US20220380296A1 (en) | 2022-12-01 |
| CN109641819A (zh) | 2019-04-16 |
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| CN109641819B (zh) | 2022-01-07 |
| US11858875B2 (en) | 2024-01-02 |
| EP3500546A1 (en) | 2019-06-26 |
| US20210284892A1 (en) | 2021-09-16 |
| KR20190040979A (ko) | 2019-04-19 |
| JP2019535642A (ja) | 2019-12-12 |
| US11479525B2 (en) | 2022-10-25 |
| WO2018039096A1 (en) | 2018-03-01 |
| JP7076886B2 (ja) | 2022-05-30 |
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