JP5706313B2 - 過熱水の存在下でアミドを製造する方法 - Google Patents
過熱水の存在下でアミドを製造する方法 Download PDFInfo
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- JP5706313B2 JP5706313B2 JP2011502253A JP2011502253A JP5706313B2 JP 5706313 B2 JP5706313 B2 JP 5706313B2 JP 2011502253 A JP2011502253 A JP 2011502253A JP 2011502253 A JP2011502253 A JP 2011502253A JP 5706313 B2 JP5706313 B2 JP 5706313B2
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- 125000003118 aryl group Chemical group 0.000 claims description 34
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
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- 238000004519 manufacturing process Methods 0.000 claims description 16
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000010923 batch production Methods 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
- 125000004122 cyclic group Chemical group 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 125000002619 bicyclic group Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 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
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- KJDZDTDNIULJBE-QXMHVHEDSA-N cetoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCCCC(O)=O KJDZDTDNIULJBE-QXMHVHEDSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 1
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 235000021299 gondoic acid Nutrition 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IIUXHTGBZYEGHI-UHFFFAOYSA-N iso-margaric acid Natural products CC(C)CCCCCCCCCCCCCC(O)=O IIUXHTGBZYEGHI-UHFFFAOYSA-N 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
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940031957 lauric acid diethanolamide Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 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
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 238000007144 microwave assisted synthesis reaction Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- FZQAYFWUOCXLKJ-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)octanamide Chemical compound CCCCCCCC(=O)N(CCO)CCO FZQAYFWUOCXLKJ-UHFFFAOYSA-N 0.000 description 1
- KUYQDJOFVBGZID-UHFFFAOYSA-N n,n-diethyl-2-methylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1C KUYQDJOFVBGZID-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- VIJUZNJJLALGNJ-UHFFFAOYSA-N n,n-dimethylbutanamide Chemical compound CCCC(=O)N(C)C VIJUZNJJLALGNJ-UHFFFAOYSA-N 0.000 description 1
- HNXNKTMIVROLTK-UHFFFAOYSA-N n,n-dimethyldecanamide Chemical compound CCCCCCCCCC(=O)N(C)C HNXNKTMIVROLTK-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- FJEVKYZLIRAAKE-UHFFFAOYSA-N n,n-dimethylpyridine-3-carboxamide Chemical compound CN(C)C(=O)C1=CC=CN=C1 FJEVKYZLIRAAKE-UHFFFAOYSA-N 0.000 description 1
- IFTIBNDWGNYRLS-UHFFFAOYSA-N n,n-dipropylacetamide Chemical compound CCCN(C(C)=O)CCC IFTIBNDWGNYRLS-UHFFFAOYSA-N 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
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- HSXFVHLMNNGPBN-UHFFFAOYSA-N n-ethyl-2-hydroxy-2-phenylacetamide Chemical compound CCNC(=O)C(O)C1=CC=CC=C1 HSXFVHLMNNGPBN-UHFFFAOYSA-N 0.000 description 1
- JKZQBSUPPNQHTK-UHFFFAOYSA-N n-ethyl-2-methylideneoctanamide Chemical compound CCCCCCC(=C)C(=O)NCC JKZQBSUPPNQHTK-UHFFFAOYSA-N 0.000 description 1
- XJZXPKBSAGMSKC-UHFFFAOYSA-N n-ethylethanamine;3-methylbenzoic acid Chemical compound CCNCC.CC1=CC=CC(C(O)=O)=C1 XJZXPKBSAGMSKC-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- ZBWPKQRQZDZVSF-UHFFFAOYSA-N n-octylformamide Chemical compound CCCCCCCCNC=O ZBWPKQRQZDZVSF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HSUGDXPUFCVGES-UHFFFAOYSA-N n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCCCC HSUGDXPUFCVGES-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical class CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 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
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 125000000913 palmityl 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])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 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920006260 polyaryletherketone Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000004079 stearyl 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])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 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003760 tallow 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
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/126—Microwaves
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
次の式(I)で表されるカルボン酸の少なくとも一種、
R3−COOH (I)
(式中、R3は、水素、または場合によっては置換されている1〜50個のC原子を有する炭化水素残基を示す。)と、
次の式(II)で表されるアミンの少なくとも一種、
HNR1R2 (II)
(式中、R1とR2は、互いに独立して、水素、または場合によっては置換されている1〜100個のC原子を有する炭化水素残基を示す。)と、
を反応させてアンモニウム塩とし、そしてこのアンモニウム塩を過熱水の存在下で、マイクロ波照射の下でカルボン酸アミドに転化する、上記の方法である。
次の式Iで表されるカルボン酸の少なくとも一種、
R3−COOH (I)
(式中、R3は、水素、または場合によっては置換されている1〜50個のC原子を有する炭化水素残基を示す。)と、
次の式IIで表されるアミンの少なくとも一種、
HNR1R2 (II)
(式中、R1とR2は、互いに独立して、水素、または場合によっては置換されている1〜100個のC原子を有する炭化水素残基を示す。)と、
を、水の存在下で反応させてアンモニウム塩とし、こうして製造されたアンモニウム塩を、100℃を超える温度でマイクロ波照射の下でカルボン酸アミドに転化する、上記の方法である。
R3−COOH (I)
(式中、R3は、水素、または場合によっては置換されている1〜50個のC原子を有する炭化水素残基を示す。)と、
次の式IIで表されるアミンの少なくとも一種、
HNR1R2 (II)
(式中、R1とR2は、互いに独立して、水素、または場合によっては置換されている1〜100個のC原子を有する炭化水素残基を示す。)と、
からなるアンモニウム塩に、マイクロ波照射の前に水を加える、上記の方法である。
−(R4−O)n−R5 (III)
(式中、
R4は、2〜6個のC原子、好ましくは2〜4個のC原子を有するアルキレン基、例えばエチレン、プロピレン、ブチレン、またはそれらの混合物を示し、
R5は、水素、1〜24個のC原子を有する炭化水素残基、または式−NR10R11の基を示し、
nは、2〜50、好ましくは3〜25、特に4〜10の数を示し、
R10、R11は、互いに独立して、水素、1〜24個のC原子、好ましくは2〜18個のC原子を有する脂肪族残基、5〜12員環のアリール基またはヘテロアリール基、1〜50個のポリ(オキシアルキレン)単位を有するポリ(オキシアルキレン)基を示し、ここで、ポリ(オキシアルキレン)単位は、2〜6個のC原子を有するアルキレンオキシド単位から誘導されるか、あるいはR10、R11が、これらが結合する窒素原子と共に、環員数が4、5、6、またはそれよりも多い環を形成する。)
を示す。
−[R6−N(R7)]m−(R7) (IV)
(式中、
R6は、2〜6個のC原子、好ましくは2〜4個のC原子を有するアルキレン基、例えばエチレン、プロピレン、またはそれらの混合物を示し、
各R7は、互いに独立して、水素、最大24個のC原子、例えば2〜20個のC原子を有するアルキル残基またはヒドロキシアルキル残基、ポリオキシアルキレン残基−(R4−O)p−R5、またはポリイミノアルキレン残基−[R6−N(R7)]q−(R7)(式中、R4、R5、R6およびR7は、上述の意味を有し、qとpは、互いに独立して、1〜50を示す。)を示し、
mは、1〜20の数、好ましくは2〜10の数、例えば3、4、5、または6を示す。)
を示す。この式IVの残基は、好ましくは1〜50個、特に2〜20個の窒素原子を含む。
マイクロ波の照射は、単モードマイクロ波反応装置であるBiotage社のタイプInitiator(登録商標)中で、2.45GHzの周波数で行う。温度測定はIRセンサによって行った。密封した耐圧性の5ml容量のガラスキュベット(耐圧性小ビン)を反応容器として用い、磁気撹拌器で均質化した。温度測定はIRセンサによって行う。
ガス導入管、撹拌器、内部温度計、圧調整器を備えた500mlの三口フラスコ中に、Lactol 90(登録商標)(乳酸1モル、90%濃度の水性調節物)100gを仕込んだ。氷冷しながらガス状のジメチルアミン45.1g(1モル)をゆっくりとフラスコ内に導入したところ、乳酸−N,N−ジメチルアンモニウム塩が激しい発熱反応において生成した。
ガス導入管、撹拌器、内部温度計、圧力調整器を備えた500mlの三口フラスコ中に、4−メトキシフェニル酢酸166.2g(1モル)を仕込み、冷却しながらジメチルアミン112.5g(40%濃度の水溶液として)でゆっくりと中和した。4−メトキシフェニル酢酸のN,N−ジメチルアンモニウム塩が、激しい発熱反応中で生成した。この塩の水溶液の固形分含量は76%であった。この溶液のアリコートにさらに水を加えて塩を50%に希釈した。
ガス導入管、撹拌器、内部温度計、圧力調整器を備えた500mlの三口フラスコ中に、デカン酸172g(1モル)を仕込み、ジメチルアミン112.5g(40%濃度の水溶液として)で慎重に中和した。デカン酸−N,N−ジメチルアンモニウム塩が、発熱反応中で生成した。ペースト状で水性形態のこの塩の固形分含量は76重量%であった。この溶液のアリコートにさらに水を加えて塩を55重量%に希釈した。
ガス導入管、撹拌器、内部温度計、圧力調整器を備えた500mlの三口フラスコ中に、m−トルイル酸136.2g(1モル)を仕込み、ジエチルアミン109.71g(1.5モル)で慎重に中和した。m−トルイル酸−N,N−ジエチルアンモニウム塩が、激しい発熱反応中で生成した。この原液からアリコートを取り、水を加えて、表4に示される水分含量に調整した。
Claims (21)
- カルボン酸アミドの製造方法であり、
次の式(I)で表されるカルボン酸の少なくとも一種、
R3−COOH (I)
(式中、R3は、水素、または1〜50個のC原子を有する炭化水素残基を示し、その際、該炭化水素残基は、置換されていないかまたはC 1 〜C 20 のアルキル基、C 1 〜C 5 アルコキシ基、ポリ(C 1 〜C 5 アルコキシ)基、ポリ(C 1 〜C 5 アルコキシ)アルキル基およびヒドロキシル基から選択される1つまたは複数の置換基で置換されている。)と、
次の式(II)で表されるアミンの少なくとも一種、
HNR1R2 (II)
(式中、R1とR2は、互いに独立して、水素、または1〜100個のC原子を有する炭化水素残基を示し、その際、該炭化水素残基は、置換されていないかまたはヒドロキシ基、C 1 〜C 5 アルコキシ基、シアノ基、ニトロ基、およびC 5 〜C 20 アリール基から選択される置換基で置換されており、および/または、
該炭化水素残基は、ヘテロ原子に割り込まれたアルキル残基であることができ、その際、そのアルキル残基は、
式IIIで表される残基、
−(R 4 −O) n −R 5 (III)
(式中、
R 4 は、2〜6個のC原子を有するアルキレン基を表し、
R 5 は、水素、または1〜24個のC原子を有する炭化水素残基を示し、
nは、2〜50の数を示す。)であるか、あるいは、
次の式IVで表される残基、
−[R 6 −N(R 7 )] m −(R 7 ) (IV)
(式中、
R 6 は、2〜6個のC原子を有するアルキレン基またはそれらの混合物を示し、
各R 7 は、互いに独立して、水素、24個までのC原子を有するアルキル残基またはヒドロキシアルキル残基、ポリオキシアルキレン残基−(R 4 −O) p −R 5 、またはポリイミノアルキレン残基−[R 6 −N(R 7 )] q −(R 7 )(式中、R 4 、R 5 、R 6 、およびR 7 は上述の意味を有し、qとpは、互いに独立して、1〜50を示す。)を示し、mは、1〜20の数を示す。)であるか、あるいは、
R1とR2は一緒に、これらが結合している窒素原子と共に環を形成する。)と、
を反応させてアンモニウム塩とし、そしてこのアンモニウム塩を過熱水の存在下で、マイクロ波照射の下でカルボン酸アミドに転化し、その際に、前記カルボン酸および前記アミンから形成された該アンモニウム塩に、マイクロ波での照射前に水が加えられ、その際にマイクロ波照射が150℃を超える温度で行われる、上記の方法。 - カルボン酸アミドの製造方法であり、
次の式Iで表されるカルボン酸の少なくとも一種、
R3−COOH (I)
(式中、R3は、水素、または1〜50個のC原子を有する炭化水素残基を示し、その際、該炭化水素残基は、置換されていないかまたはC 1 〜C 20 のアルキル基、C 1 〜C 5 アルコキシ基、ポリ(C 1 〜C 5 アルコキシ)基、ポリ(C 1 〜C 5 アルコキシ)アルキル基およびヒドロキシル基から選択される1つまたは複数の置換基で置換されている。)と、
次の式IIで表されるアミンの少なくとも一種、
HNR1R2 (II)
(式中、R1とR2は、互いに独立して、水素、または1〜100個のC原子を有する炭化水素残基を示し、その際、該炭化水素残基は、置換されていないかまたはヒドロキシ基、C 1 〜C 5 アルコキシ基、シアノ基、ニトロ基、およびC 5 〜C 20 アリール基から選択される置換基で置換されており、および/または、
該炭化水素残基は、ヘテロ原子に割り込まれたアルキル残基であることができ、その際、そのアルキル残基は、
式IIIで表される残基、
−(R 4 −O) n −R 5 (III)
(式中、
R 4 は、2〜6個のC原子を有するアルキレン基を表し、
R 5 は、水素、または1〜24個のC原子を有する炭化水素残基を示し、
nは、2〜50の数を示す。)であるか、あるいは、
次の式IVで表される残基、
−[R 6 −N(R 7 )] m −(R 7 ) (IV)
(式中、
R 6 は、2〜6個のC原子を有するアルキレン基またはそれらの混合物を示し、
各R 7 は、互いに独立して、水素、24個までのC原子を有するアルキル残基またはヒドロキシアルキル残基、ポリオキシアルキレン残基−(R 4 −O) p −R 5 、またはポリイミノアルキレン残基−[R 6 −N(R 7 )] q −(R 7 )(式中、R 4 、R 5 、R 6 、およびR 7 は上述の意味を有し、qとpは、互いに独立して、1〜50を示す。)を示し、mは、1〜20の数を示す。)であるか、あるいは、
R1とR2は一緒に、これらが結合している窒素原子と共に環を形成する。)と、
を、水の存在下で反応させてアンモニウム塩とし、こうして製造されたアンモニウム塩を、150℃を超える温度でマイクロ波照射の下でカルボン酸アミドに転化する、上記の方法。 - マイクロ波支援のアミド化反応の転化率を高める方法であり、その際に次の式Iで表されるカルボン酸の少なくとも一種、
R3−COOH (I)
(式中、R3は、水素、または1〜50個のC原子を有する炭化水素残基を示し、その際、該炭化水素残基は、置換されていないかまたはC 1 〜C 20 のアルキル基、C 1 〜C 5 アルコキシ基、ポリ(C 1 〜C 5 アルコキシ)基、ポリ(C 1 〜C 5 アルコキシ)アルキル基およびヒドロキシル基から選択される1つまたは複数の置換基で置換されている。)、および
次の式IIで表されるアミンの少なくとも一種
HNR1R2 (II)
(式中、R1とR2は、互いに独立して、水素、または1〜100個のC原子を有する炭化水素残基を示し、その際、該炭化水素残基は、置換されていないかまたはヒドロキシ基、C 1 〜C 5 アルコキシ基、シアノ基、ニトロ基、およびC 5 〜C 20 アリール基から選択される置換基で置換されており、および/または、
該炭化水素残基は、ヘテロ原子に割り込まれたアルキル残基であることができ、その際、そのアルキル残基は、
式IIIで表される残基、
−(R 4 −O) n −R 5 (III)
(式中、
R 4 は、2〜6個のC原子を有するアルキレン基を表し、
R 5 は、水素、または1〜24個のC原子を有する炭化水素残基を示し、
nは、2〜50の数を示す。)であるか、あるいは、
次の式IVで表される残基、
−[R 6 −N(R 7 )] m −(R 7 ) (IV)
(式中、
R 6 は、2〜6個のC原子を有するアルキレン基またはそれらの混合物を示し、
各R 7 は、互いに独立して、水素、24個までのC原子を有するアルキル残基またはヒドロキシアルキル残基、ポリオキシアルキレン残基−(R 4 −O) p −R 5 、またはポリイミノアルキレン残基−[R 6 −N(R 7 )] q −(R 7 )(式中、R 4 、R 5 、R 6 、およびR 7 は上述の意味を有し、qとpは、互いに独立して、1〜50を示す。)を示し、mは、1〜20の数を示す。)である。)
からなるアンモニウム塩にマイクロ波照射の前に水を加え、その際にマイクロ波照射が150℃を超える温度で行われる、上記の方法。 - マイクロ波の照射が、大気圧より高い圧力下で行われる、請求項1〜3のいずれか一つに記載の方法。
- R3が、C 1 〜C 20 のアルキル基、C1〜C5アルコキシ基、ポリ(C1〜C5アルコキシ)基、ポリ(C1〜C5アルコキシ)アルキル基およびヒドロキシル基から選択される1つまたは複数の置換基を有する、1〜50個のC原子を有する炭化水素残基である、請求項1〜4のいずれか一つに記載の方法。
- R3が、脂肪族、脂環式、芳香族、または芳香脂肪族炭化水素を示す、請求項1〜5のいずれか一つに記載の方法。
- R3が、1つまたは複数の二重結合を含む、請求項1〜6のいずれか一つに記載の方法。
- R1とR2が、互いに独立して、1〜100個の炭素原子を有する炭化水素残基を示す、請求項1〜7のいずれか一つに記載の方法。
- R1が1〜100個の炭素原子を有する炭化水素残基を示し、そしてR2が水素を示す、請求項1〜7のいずれか一つに記載の方法。
- R1またはR2、あるいは両方の残基が、互いに独立して、1〜24個のC原子を有する脂肪族残基を示す、請求項1〜7のいずれか一つに記載の方法。
- R1またはR2、あるいは両方の残基が、ヒドロキシ基、C1〜C5アルコキシ基、シアノ基、ニトロ基、およびC5〜C20アリール基から選択される置換基を有する、請求項1〜10のいずれか一つに記載の方法。
- R1またはR2、あるいは両方の基が、C5〜C20アリール基を有し、そしてこのアリール基が、ハロゲン原子、ハロゲン化アルキル残基、C1〜C20アルキル基、C2〜C20アルケニル基、C1〜C5アルコキシ基、エステル基、アミド基、シアノ基およびニトロ基から選択される1つまたは複数の置換基を有する、請求項1〜11のいずれか一つに記載の方法。
- R1とR2とが、窒素原子で結合されて一緒に環を形成する、請求項1〜7のいずれか一つに記載の方法。
- R1とR2が、互いに独立して、上記の式IIIで表される残基である、
請求項1〜7のいずれか一つに記載の方法。 - R1とR2が、互いに独立して、上記の式IVで表される残基である、
請求項1〜7のいずれか一つに記載の方法。 - マイクロ波による前記塩の照射が非連続のバッチ法で行われる、請求項1〜15のいずれか一つに記載の方法。
- マイクロ波による前記塩の照射が連続法で行われる、請求項1〜16のいずれか一つに記載の方法。
- マイクロ波による前記塩の照射が、広範囲に及ぶマイクロ波透過反応管中で行われる、請求項17に記載の方法。
- マイクロ波による前記塩の照射が、単モード−マイクロ波照射容器のマイクロ波の伝播方向に長手軸がある反応管中で行われる、請求項17または18に記載の方法。
- マイクロ波の照射が、カルボン酸およびアミンの全質量に基づいて0.5〜200重量%の水の存在下で実施される、請求項1〜19のいずれか一つに記載の方法。
- マイクロ波の照射が、180℃を超える温度で実施される、請求項1〜20のいずれか一つに記載の方法。
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- 2009-03-18 WO PCT/EP2009/001988 patent/WO2009121488A1/de active Application Filing
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CN101983185A (zh) | 2011-03-02 |
AU2009231123A1 (en) | 2009-10-08 |
ES2399784T3 (es) | 2013-04-03 |
MX2010010767A (es) | 2010-10-26 |
CN101983185B (zh) | 2015-09-02 |
JP2011516433A (ja) | 2011-05-26 |
EP2274271A1 (de) | 2011-01-19 |
KR20100135229A (ko) | 2010-12-24 |
EA018483B9 (ru) | 2013-12-30 |
WO2009121488A1 (de) | 2009-10-08 |
EA201001112A1 (ru) | 2010-12-30 |
EA018483B1 (ru) | 2013-08-30 |
CA2720341A1 (en) | 2009-10-08 |
EP2274271B1 (de) | 2013-01-23 |
US20110089021A1 (en) | 2011-04-21 |
DE102008017219A1 (de) | 2009-10-08 |
BRPI0910312A2 (pt) | 2015-09-29 |
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