JP6401097B2 - 潜熱蓄熱材 - Google Patents
潜熱蓄熱材 Download PDFInfo
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- JP6401097B2 JP6401097B2 JP2015070130A JP2015070130A JP6401097B2 JP 6401097 B2 JP6401097 B2 JP 6401097B2 JP 2015070130 A JP2015070130 A JP 2015070130A JP 2015070130 A JP2015070130 A JP 2015070130A JP 6401097 B2 JP6401097 B2 JP 6401097B2
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- substituted
- latent heat
- heat storage
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- storage material
- Prior art date
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- 238000005338 heat storage Methods 0.000 title claims description 111
- 239000011232 storage material Substances 0.000 title claims description 109
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 115
- 229910052757 nitrogen Inorganic materials 0.000 claims description 76
- 239000007983 Tris buffer Substances 0.000 claims description 36
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004450 alkenylene group Chemical group 0.000 claims description 9
- 125000004419 alkynylene group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 4
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 238000004781 supercooling Methods 0.000 description 76
- 239000000203 mixture Substances 0.000 description 71
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000000463 material Substances 0.000 description 47
- 230000000694 effects Effects 0.000 description 43
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- 238000007711 solidification Methods 0.000 description 32
- 230000008023 solidification Effects 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- 239000012043 crude product Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000011259 mixed solution Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000002597 Solanum melongena Nutrition 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 7
- 230000002776 aggregation Effects 0.000 description 7
- 239000012300 argon atmosphere Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 230000008719 thickening Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 210000001724 microfibril Anatomy 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- VUJRFBZFNLZSPI-UHFFFAOYSA-N 12-phenylmethoxydodecan-1-amine Chemical compound NCCCCCCCCCCCCOCC1=CC=CC=C1 VUJRFBZFNLZSPI-UHFFFAOYSA-N 0.000 description 3
- AZSATGGUIIEDIH-UHFFFAOYSA-N 2-(12-hydroxydodecyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCCCCCCCCO)C(=O)C2=C1 AZSATGGUIIEDIH-UHFFFAOYSA-N 0.000 description 3
- ZMMGNBYECHBRLH-UHFFFAOYSA-N 3,7-dimethyloctan-1-amine hydrochloride Chemical compound Cl.CC(C)CCCC(C)CCN ZMMGNBYECHBRLH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- VEKTZAJCKACLFH-UHFFFAOYSA-N 2-(3,7-dimethyloctyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCC(C)CCCC(C)C)C(=O)C2=C1 VEKTZAJCKACLFH-UHFFFAOYSA-N 0.000 description 2
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GXTLMPYXSUXUGH-UHFFFAOYSA-N C1=CC=C(C=C1)COCCCCCCCCCCCCN2C(=O)C3=CC=CC=C3C2=O Chemical compound C1=CC=C(C=C1)COCCCCCCCCCCCCN2C(=O)C3=CC=CC=C3C2=O GXTLMPYXSUXUGH-UHFFFAOYSA-N 0.000 description 2
- MKMOEGHVKSKFBQ-UHFFFAOYSA-N CN(C)CCCCCCCCCCCCN1C(=O)C2=CC=CC=C2C1=O Chemical compound CN(C)CCCCCCCCCCCCN1C(=O)C2=CC=CC=C2C1=O MKMOEGHVKSKFBQ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 125000000815 N-oxide group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- FTHDNRBKSLBLDA-UHFFFAOYSA-N cyclohexane-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)CC(C(O)=O)C1 FTHDNRBKSLBLDA-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
- HFVIYAZBVIGNAN-UHFFFAOYSA-N 1,1-dibromodecane Chemical compound CCCCCCCCCC(Br)Br HFVIYAZBVIGNAN-UHFFFAOYSA-N 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- VGSUDZKDSKCYJP-UHFFFAOYSA-N 1-bromo-3,7-dimethyloctane Chemical compound CC(C)CCCC(C)CCBr VGSUDZKDSKCYJP-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006439 1-n-propyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PHHKDUQVDGZAJS-UHFFFAOYSA-N CC(CCCCCCCCCCCN)NC Chemical compound CC(CCCCCCCCCCCN)NC PHHKDUQVDGZAJS-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ASIDMJNTHJYVQJ-UHFFFAOYSA-N bromo-dodecanol Chemical compound OCCCCCCCCCCCCBr ASIDMJNTHJYVQJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
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- 235000013922 glutamic acid Nutrition 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 1
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
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- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BPELEZSCHIEMAE-UHFFFAOYSA-N salicylaldehyde imine Chemical class OC1=CC=CC=C1C=N BPELEZSCHIEMAE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(1) 式(I):
nは、2〜5の整数であり、
Xは、シクロヘキサン環又はベンゼン環に由来する基であり、
R1は、-R2-Yであり、
R2は、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルキレン、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルケニレン、又は置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルキニレンであり、ここで、前記基は、1個以上の-O-、-S-、-NH-、置換若しくは非置換のC3〜C6シクロアルキレン、置換若しくは非置換のC3〜C6シクロアルケニレン、置換若しくは非置換のC3〜C6シクロアルキニレン、置換若しくは非置換の5〜15員のC3〜C6ヘテロシクロアルキレン、置換若しくは非置換のC7〜C20アリーレン又は置換若しくは非置換の5〜15員のヘテロアリーレンで中断されていてもよく、
Yは、直鎖若しくは分岐鎖のC1〜C6アルキル、-OR3、-NRN1RN2、-C(=O)R3、-COOR3、及び-SR3からなる群より選択される一価基であり、
R3は、水素、又は置換若しくは非置換の直鎖若しくは分岐鎖のC1〜C6アルキルであり、
RN1及びRN2は、互いに独立して、水素、又は置換若しくは非置換の直鎖若しくは分岐鎖のC1〜C6アルキルであり、
但し、前記基が置換されている場合、該置換基は、それぞれ独立して、ハロゲン、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C3〜C6シクロアルキル、C3〜C6シクロアルケニル、C3〜C6シクロアルキニル、C1〜C6アルコキシ、C6〜C15アリールオキシ、C7〜C20アリールアルキルオキシ、5〜15員のヘテロアリールオキシ、5〜15員のヘテロアリール-C1〜C6アルキルオキシ、C1〜C6アルコキシカルボニル、C3〜C6シクロアルコキシカルボニル、及びC1〜C6アシルオキシからなる群より選択される1個以上の1価基である。]
で表される化合物と、式(II):
H2N-(CH2)m-NH2 (II)
[式中、
mは、6〜14の整数である。]
で表されるジアミノアルカンとを含有する潜熱蓄熱材。
(2) 前記式(I)で表される化合物が、前記式(II)で表されるジアミノアルカンの総質量に対して1〜20質量%の範囲で含有される、前記(1)に記載の潜熱蓄熱材。
(3) nが3である、前記(1)又は(2)に記載の潜熱蓄熱材。
(4) R2が、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C12アルキレン、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C12アルケニレン、又は置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C12アルキニレンである、前記(1)〜(3)のいずれかに記載の潜熱蓄熱材。
(5) R2が、非置換の直鎖若しくは分岐鎖のC6〜C12アルキレンであり、
Yが、メチル、ヒドロキシル、又はN,N-ジエチルアミノである、前記(1)〜(4)のいずれかに記載の潜熱蓄熱材。
(6) 式(I)で表される化合物が、
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-シクロヘキシルトリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;又は
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
である、前記(1)〜(5)のいずれかに記載の潜熱蓄熱材。
(7) mが8〜12の整数である、前記(1)〜(6)のいずれかに記載の潜熱蓄熱材。
(8) 式(II)で表されるジアミノアルカンが、ジアミノオクタン又はジアミノドデカンである、前記(1)〜(7)のいずれかに記載の潜熱蓄熱材。
(9) 式(I):
nは、2〜5の整数であり、
Xは、シクロヘキサン環又はベンゼン環に由来する基であり、
R1は、-R2-Yであり、
R2は、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルキレン、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルケニレン、又は置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルキニレンであり、ここで、前記基は、1個以上の-O-、-S-、-NH-、置換若しくは非置換のC3〜C6シクロアルキレン、置換若しくは非置換のC3〜C6シクロアルケニレン、置換若しくは非置換のC3〜C6シクロアルキニレン、置換若しくは非置換の5〜15員のC3〜C6ヘテロシクロアルキレン、置換若しくは非置換のC7〜C20アリーレン又は置換若しくは非置換の5〜15員のヘテロアリーレンで中断されていてもよく、
Yは、直鎖若しくは分岐鎖のC1〜C6アルキル、-OR3、-NRN1RN2、-C(=O)R3、-COOR3、及び-SR3からなる群より選択される一価基であり、
R3は、水素、又は置換若しくは非置換の直鎖若しくは分岐鎖のC1〜C6アルキルであり、
RN1及びRN2は、互いに独立して、水素、又は置換若しくは非置換の直鎖若しくは分岐鎖のC1〜C6アルキルであり、
但し、前記基が置換されている場合、該置換基は、それぞれ独立して、ハロゲン、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C3〜C6シクロアルキル、C3〜C6シクロアルケニル、C3〜C6シクロアルキニル、C1〜C6アルコキシ、C6〜C15アリールオキシ、C7〜C20アリールアルキルオキシ、5〜15員のヘテロアリールオキシ、5〜15員のヘテロアリール-C1〜C6アルキルオキシ、C1〜C6アルコキシカルボニル、C3〜C6シクロアルコキシカルボニル、及びC1〜C6アシルオキシからなる群より選択される1個以上の1価基である。]
で表される化合物若しくはその塩、又はそれらの溶媒和物。
(10) 式(I)で表される化合物が、
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-シクロヘキシルトリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;又は
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
である、前記(9)に記載の化合物。
nが、3の整数であり、
Xが、1,3,5-位に-C(=O)-NH-R1で表される鎖式基が結合する構造を有するシクロヘキサン環又はベンゼン環に由来する基であり、
R1が、-R2-Yであり、且つ
R2が、オクチル、3-メチルオクチル又はドデカノイルである。
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-シクロヘキシルトリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;又は
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
である。
R1-NH2 (IV)
で表される化合物とを反応させる工程を含む、式(I)で表される化合物を製造する方法を適用することにより、実施することが好ましい。
以下の合成において、化合物の機器分析は以下の条件で行った。
1H-NMR:
分析装置:JEOL PMX60SI
周波数:60 MHz
掃引幅:0〜600 Hz
IR:
分析装置:Shimadzu FTIR-8300
HPLC:
分析装置:Shimadzu LC-10A
カラム:Mightysil RP-18 GP 250 mm×4.6 mm(5 μm)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF):アセトニトリル=1:4(化合物1、2及び5)
メタノール(化合物3、4及び6)
流速:0.5 ml/分
検出:UV(254 nm)
[1-1-1:アミンの合成(1)]
[1-2-1:酸クロリドの合成]
[1-3-1:アミンの合成(1)]
[1-4-1:アミンの合成(1)]
[1-5-1:酸クロリドの合成]
[1-6-1:N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド(化合物6)の合成]
サンプル瓶に、所定割合の過冷却付与材料及びジアミノアルカンを入れて、実施例の潜熱蓄熱材を調製した。過冷却付与材料としては、前記で調製した化合物1〜6を使用した。ジアミノアルカンとしては、ジアミノオクタン(DAO、H2N-(CH2)8-NH2)及びジアミノドデカン(DAD、H2N-(CH2)12-NH2)を使用した。各実施例の組成は、下記表1〜12に示した通りである。
〔3-1:状態観察〕
調製した実施例の潜熱蓄熱材を、約130℃に加熱して溶融させた。溶融した実施例の潜熱蓄熱材を、室温下で放冷して、該潜熱蓄熱材が凝固する状態を目視で観察した。観察した状態を、下記の基準で分類した。
状態(1):潜熱蓄熱材の各成分が互いに混じり合わない。
状態(2):潜熱蓄熱材の各成分が互いに混じり合うものの、粘度が増加しない。
状態(3):潜熱蓄熱材の各成分が互いに混じり合い且つ粘度が増加して、ゲル状態のまま過冷却する。
状態(4):潜熱蓄熱材の各成分が互いに混じり合い且つ粘度が増加するが、降温時に過冷却付与材料のみが凝集して相分離する。凝集が開始するまでは過冷却状態である。
前記手順で状態観察の実験を実施した実施例の潜熱蓄熱材を、それぞれ所定量(3〜5 mg)秤量した。示差走査熱量計(DSC)(DSC Q1000、テキサスインスツルメンツ社製)を用いて、秤量した実施例の潜熱蓄熱材のサンプルの溶融温度、溶融熱量、凝固温度及び凝固熱量を測定した。前記測定結果から、実施例の潜熱蓄熱材の過冷却温度を下記の式に基づき算出した。
過冷却温度=溶融温度−凝固温度
加熱溶融直後の状態、状態(3)及び状態(4)の潜熱蓄熱材の写真を図1に示す。図中、Aは加熱溶融直後の状態を、Bは状態(3)を、Cは状態(4)を、それぞれ示す。実施例の潜熱蓄熱材が、状態(3)又は(4)に分類される状態の場合、過冷却状態を発現したと判断した。なお、状態(1)又は(2)に分類される状態の潜熱蓄熱材であっても僅かに過冷却状態を示す場合があったが、本発明の潜熱蓄熱材における増粘効果に起因する過冷却状態の発現とは異なると考えられる。
実施例の潜熱蓄熱材の調製において、ジアミノアルカンに替えてジブロモデカン又はエリスリトールを用いた他は前記と同様の手順で、比較例の潜熱蓄熱材を調製した。
Claims (8)
- 式(I):
nは、2〜5の整数であり、
Xは、シクロヘキサン環又はベンゼン環に由来する基であり、
R1は、-R2-Yであり、
R2は、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルキレン、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルケニレン、又は置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C18アルキニレンであり、ここで、前記基は、1個以上の-O-、-S-、-NH-、置換若しくは非置換のC3〜C6シクロアルキレン、置換若しくは非置換のC3〜C6シクロアルケニレン、置換若しくは非置換のC3〜C6シクロアルキニレン、置換若しくは非置換の5〜15員のC3〜C6ヘテロシクロアルキレン、置換若しくは非置換のC7〜C20アリーレン又は置換若しくは非置換の5〜15員のヘテロアリーレンで中断されていてもよく、
Yは、直鎖若しくは分岐鎖のC1〜C6アルキル、-OR3、-NRN1RN2、-C(=O)R3、-COOR3、及び-SR3からなる群より選択される一価基であり、
R3は、水素、又は置換若しくは非置換の直鎖若しくは分岐鎖のC1〜C6アルキルであり、 RN1及びRN2は、互いに独立して、水素、又は置換若しくは非置換の直鎖若しくは分岐鎖のC1〜C6アルキルであり、
但し、前記基が置換されている場合、該置換基は、それぞれ独立して、ハロゲン、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C3〜C6シクロアルキル、C3〜C6シクロアルケニル、C3〜C6シクロアルキニル、C1〜C6アルコキシ、C6〜C15アリールオキシ、C7〜C20アリールアルキルオキシ、5〜15員のヘテロアリールオキシ、5〜15員のヘテロアリール-C1〜C6アルキルオキシ、C1〜C6アルコキシカルボニル、C3〜C6シクロアルコキシカルボニル、及びC1〜C6アシルオキシからなる群より選択される1個以上の1価基である。]で表される化合物と、式(II):
H2N-(CH2)m-NH2 (II)
[式中、
mは、6〜14の整数である。]
で表されるジアミノアルカンとを含有する潜熱蓄熱材。 - 前記式(I)で表される化合物が、前記式(II)で表されるジアミノアルカンの総質量に対して1〜20質量%の範囲で含有される、請求項1に記載の潜熱蓄熱材。
- nが3である、請求項1又は2に記載の潜熱蓄熱材。
- R2が、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C12アルキレン、置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C12アルケニレン、又は置換若しくは非置換の直鎖若しくは分岐鎖のC6〜C12アルキニレンである、請求項1〜3のいずれか1項に記載の潜熱蓄熱材。
- R2が、非置換の直鎖若しくは分岐鎖のC6〜C12アルキレンであり、
Yが、メチル、ヒドロキシル、又はN,N-ジエチルアミノである、請求項1〜4のいずれか1項に記載の潜熱蓄熱材。 - 式(I)で表される化合物が、
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(3,7-ジメチルオクチル)-1,3,5-シクロヘキシルトリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;
N,N',N''-トリス(12-ヒドロキシル-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-ベンゼントリカボキサミド;又は
N,N',N''-トリス(12-ジエチルアミノ-ドデカノイル)-1,3,5-シクロヘキシルトリカルボキサミド;
である、請求項1〜5のいずれか1項に記載の潜熱蓄熱材。 - mが8〜12の整数である、請求項1〜6のいずれか1項に記載の潜熱蓄熱材。
- 式(II)で表されるジアミノアルカンが、ジアミノオクタン又はジアミノドデカンである、請求項1〜7のいずれか1項に記載の潜熱蓄熱材。
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JP6312669B2 (ja) * | 2013-06-25 | 2018-04-18 | 株式会社ダイセル | 増粘安定剤、及びそれを用いた増粘安定化組成物 |
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