ZA200402622B - Production of keto acids - Google Patents
Production of keto acids Download PDFInfo
- Publication number
- ZA200402622B ZA200402622B ZA200402622A ZA200402622A ZA200402622B ZA 200402622 B ZA200402622 B ZA 200402622B ZA 200402622 A ZA200402622 A ZA 200402622A ZA 200402622 A ZA200402622 A ZA 200402622A ZA 200402622 B ZA200402622 B ZA 200402622B
- Authority
- ZA
- South Africa
- Prior art keywords
- aminophenol
- carbon atoms
- phthalic anhydride
- reaction
- cycloalkyl
- Prior art date
Links
- 150000004715 keto acids Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 3-tetrahydrofuryl Chemical group 0.000 claims description 44
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 35
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 27
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 229940018563 3-aminophenol Drugs 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 230000035484 reaction time Effects 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 239000007790 solid phase Substances 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 18
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012965 benzophenone Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- NOXLTVYOJPQDLQ-UHFFFAOYSA-N 2-(dibutylamino)phenol Chemical compound CCCCN(CCCC)C1=CC=CC=C1O NOXLTVYOJPQDLQ-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- YOIQWFZSLGRZJX-UHFFFAOYSA-N 2-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC=C1O YOIQWFZSLGRZJX-UHFFFAOYSA-N 0.000 description 2
- AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 description 2
- FBWXLUBJSHUIGZ-UHFFFAOYSA-N 2-(n-ethylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CC)C1=CC=CC=C1 FBWXLUBJSHUIGZ-UHFFFAOYSA-N 0.000 description 2
- LOGNQTMUWFJKNJ-UHFFFAOYSA-N 2-[butyl(propyl)amino]phenol Chemical compound CCCCN(CCC)C1=CC=CC=C1O LOGNQTMUWFJKNJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- TWIRJXSANRWKKH-UHFFFAOYSA-N 2-(2-methylanilino)phenol Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1O TWIRJXSANRWKKH-UHFFFAOYSA-N 0.000 description 1
- KLDBLONDCZEWJG-UHFFFAOYSA-N 2-(3-methyl-n-propylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CCC)C1=CC=CC(C)=C1 KLDBLONDCZEWJG-UHFFFAOYSA-N 0.000 description 1
- IAGKEBNACOQUAP-UHFFFAOYSA-N 2-(3-methylanilino)phenol Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)O)=C1 IAGKEBNACOQUAP-UHFFFAOYSA-N 0.000 description 1
- NQTSBOHCYASAMX-UHFFFAOYSA-N 2-(cyclohexylamino)phenol Chemical compound OC1=CC=CC=C1NC1CCCCC1 NQTSBOHCYASAMX-UHFFFAOYSA-N 0.000 description 1
- RWWLLSSSJJQYDQ-UHFFFAOYSA-N 2-(dihexylamino)phenol Chemical compound CCCCCCN(CCCCCC)C1=CC=CC=C1O RWWLLSSSJJQYDQ-UHFFFAOYSA-N 0.000 description 1
- SVFWTJMLZPCSMK-UHFFFAOYSA-N 2-(dipropylamino)phenol Chemical compound CCCN(CCC)C1=CC=CC=C1O SVFWTJMLZPCSMK-UHFFFAOYSA-N 0.000 description 1
- XRYYXUTYPWJRNE-UHFFFAOYSA-N 2-(n,3-dimethylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(C)C1=CC=CC(C)=C1 XRYYXUTYPWJRNE-UHFFFAOYSA-N 0.000 description 1
- QJBSVIVBYKVMJU-UHFFFAOYSA-N 2-(n-butyl-2-methylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)C1=CC=CC=C1C QJBSVIVBYKVMJU-UHFFFAOYSA-N 0.000 description 1
- VQXZBNUTXNSKGX-UHFFFAOYSA-N 2-(n-butyl-3-methylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)C1=CC=CC(C)=C1 VQXZBNUTXNSKGX-UHFFFAOYSA-N 0.000 description 1
- FGMZBIAPGJPFSV-UHFFFAOYSA-N 2-(n-butyl-4-methylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)C1=CC=C(C)C=C1 FGMZBIAPGJPFSV-UHFFFAOYSA-N 0.000 description 1
- WENYZJYXEIHOIQ-UHFFFAOYSA-N 2-(n-butylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)C1=CC=CC=C1 WENYZJYXEIHOIQ-UHFFFAOYSA-N 0.000 description 1
- UXOTZTXQYPGXRR-UHFFFAOYSA-N 2-(n-ethyl-2-methylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CC)C1=CC=CC=C1C UXOTZTXQYPGXRR-UHFFFAOYSA-N 0.000 description 1
- JYYHTAQKASOEAA-UHFFFAOYSA-N 2-(n-ethyl-3-methylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CC)C1=CC=CC(C)=C1 JYYHTAQKASOEAA-UHFFFAOYSA-N 0.000 description 1
- YGYKAPGMWTWGFW-UHFFFAOYSA-N 2-(n-methylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(C)C1=CC=CC=C1 YGYKAPGMWTWGFW-UHFFFAOYSA-N 0.000 description 1
- HVHKBLCZQNDXOM-UHFFFAOYSA-N 2-(n-propylanilino)phenol Chemical compound C=1C=CC=C(O)C=1N(CCC)C1=CC=CC=C1 HVHKBLCZQNDXOM-UHFFFAOYSA-N 0.000 description 1
- JNIBPEJFXYGMNE-UHFFFAOYSA-N 2-[2-methylpropyl(propyl)amino]phenol Chemical compound CCCN(CC(C)C)C1=CC=CC=C1O JNIBPEJFXYGMNE-UHFFFAOYSA-N 0.000 description 1
- YLWRUKZNVCFFTF-UHFFFAOYSA-N 2-[2-phenylethyl(propyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CCC)CCC1=CC=CC=C1 YLWRUKZNVCFFTF-UHFFFAOYSA-N 0.000 description 1
- JMMIWWSBAFSEHG-UHFFFAOYSA-N 2-[3-ethoxypropyl(ethyl)amino]phenol Chemical compound CCOCCCN(CC)C1=CC=CC=C1O JMMIWWSBAFSEHG-UHFFFAOYSA-N 0.000 description 1
- FQNKTJPBXAZUGC-UHFFFAOYSA-N 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O FQNKTJPBXAZUGC-UHFFFAOYSA-N 0.000 description 1
- ADMQXASAAYDVNF-UHFFFAOYSA-N 2-[butan-2-yl(butyl)amino]phenol Chemical compound CCCCN(C(C)CC)C1=CC=CC=C1O ADMQXASAAYDVNF-UHFFFAOYSA-N 0.000 description 1
- MDRIJQWXHWCPRN-UHFFFAOYSA-N 2-[butan-2-yl(ethyl)amino]phenol Chemical compound CCC(C)N(CC)C1=CC=CC=C1O MDRIJQWXHWCPRN-UHFFFAOYSA-N 0.000 description 1
- MHTFVUPSSAPOKJ-UHFFFAOYSA-N 2-[butyl(2-methylpropyl)amino]phenol Chemical compound CCCCN(CC(C)C)C1=CC=CC=C1O MHTFVUPSSAPOKJ-UHFFFAOYSA-N 0.000 description 1
- NASLUNYMLAWBRX-UHFFFAOYSA-N 2-[butyl(2-phenylethyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)CCC1=CC=CC=C1 NASLUNYMLAWBRX-UHFFFAOYSA-N 0.000 description 1
- NEDXQXLBTGHIAJ-UHFFFAOYSA-N 2-[butyl(3-ethoxypropyl)amino]phenol Chemical compound CCOCCCN(CCCC)C1=CC=CC=C1O NEDXQXLBTGHIAJ-UHFFFAOYSA-N 0.000 description 1
- VVOXFEYITHGLOD-UHFFFAOYSA-N 2-[butyl(cyclohexyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)C1CCCCC1 VVOXFEYITHGLOD-UHFFFAOYSA-N 0.000 description 1
- UKSLXIWMDMGWFL-UHFFFAOYSA-N 2-[butyl(cyclohexylmethyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CCCC)CC1CCCCC1 UKSLXIWMDMGWFL-UHFFFAOYSA-N 0.000 description 1
- ANADVGJIOCOPAF-UHFFFAOYSA-N 2-[butyl(hexyl)amino]phenol Chemical compound CCCCCCN(CCCC)C1=CC=CC=C1O ANADVGJIOCOPAF-UHFFFAOYSA-N 0.000 description 1
- RUCMKBJBXFXFPG-UHFFFAOYSA-N 2-[butyl(methyl)amino]phenol Chemical compound CCCCN(C)C1=CC=CC=C1O RUCMKBJBXFXFPG-UHFFFAOYSA-N 0.000 description 1
- IXUWPCXNWVHOPP-UHFFFAOYSA-N 2-[butyl(pentyl)amino]phenol Chemical compound CCCCCN(CCCC)C1=CC=CC=C1O IXUWPCXNWVHOPP-UHFFFAOYSA-N 0.000 description 1
- PAHZGFLOHTXFMR-UHFFFAOYSA-N 2-[cyclohexyl(ethyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CC)C1CCCCC1 PAHZGFLOHTXFMR-UHFFFAOYSA-N 0.000 description 1
- VXMIKNOYOIKSQB-UHFFFAOYSA-N 2-[cyclohexyl(methyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(C)C1CCCCC1 VXMIKNOYOIKSQB-UHFFFAOYSA-N 0.000 description 1
- LHKHLKWURDRHII-UHFFFAOYSA-N 2-[cyclohexyl(propyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CCC)C1CCCCC1 LHKHLKWURDRHII-UHFFFAOYSA-N 0.000 description 1
- ZQOHRRJIOYEILB-UHFFFAOYSA-N 2-[cyclohexylmethyl(ethyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CC)CC1CCCCC1 ZQOHRRJIOYEILB-UHFFFAOYSA-N 0.000 description 1
- XRGZEAFEYZXNRO-UHFFFAOYSA-N 2-[cyclohexylmethyl(methyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(C)CC1CCCCC1 XRGZEAFEYZXNRO-UHFFFAOYSA-N 0.000 description 1
- XCIMNBXMBSELRS-UHFFFAOYSA-N 2-[cyclohexylmethyl(propyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CCC)CC1CCCCC1 XCIMNBXMBSELRS-UHFFFAOYSA-N 0.000 description 1
- AYCDITIHWXMHPQ-UHFFFAOYSA-N 2-[di(butan-2-yl)amino]phenol Chemical compound CCC(C)N(C(C)CC)c1ccccc1O AYCDITIHWXMHPQ-UHFFFAOYSA-N 0.000 description 1
- VOSQIDFRYCSRGV-UHFFFAOYSA-N 2-[ethyl(2-methylpropyl)amino]phenol Chemical compound CC(C)CN(CC)C1=CC=CC=C1O VOSQIDFRYCSRGV-UHFFFAOYSA-N 0.000 description 1
- ZDHOHUHNEZSHDS-UHFFFAOYSA-N 2-[ethyl(2-phenylethyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(CC)CCC1=CC=CC=C1 ZDHOHUHNEZSHDS-UHFFFAOYSA-N 0.000 description 1
- NPLDPFJOFYGGCX-UHFFFAOYSA-N 2-[ethyl(3-methylbutyl)amino]phenol Chemical compound CC(C)CCN(CC)C1=CC=CC=C1O NPLDPFJOFYGGCX-UHFFFAOYSA-N 0.000 description 1
- FZZXBUKXIPFPFO-UHFFFAOYSA-N 2-[ethyl(hexan-2-yl)amino]phenol Chemical compound CCCCC(C)N(CC)C1=CC=CC=C1O FZZXBUKXIPFPFO-UHFFFAOYSA-N 0.000 description 1
- ZQBMORUJKUGUAD-UHFFFAOYSA-N 2-[ethyl(pentan-2-yl)amino]phenol Chemical compound CCCC(C)N(CC)C1=CC=CC=C1O ZQBMORUJKUGUAD-UHFFFAOYSA-N 0.000 description 1
- WSYQICTYJNDJGM-UHFFFAOYSA-N 2-[ethyl(pentyl)amino]phenol Chemical compound CCCCCN(CC)C1=CC=CC=C1O WSYQICTYJNDJGM-UHFFFAOYSA-N 0.000 description 1
- FCFPSFMLBUJTAT-UHFFFAOYSA-N 2-[ethyl(propan-2-yl)amino]phenol Chemical compound CCN(C(C)C)C1=CC=CC=C1O FCFPSFMLBUJTAT-UHFFFAOYSA-N 0.000 description 1
- URJMHXLSDIRKCN-UHFFFAOYSA-N 2-[hexyl(methyl)amino]phenol Chemical compound CCCCCCN(C)C1=CC=CC=C1O URJMHXLSDIRKCN-UHFFFAOYSA-N 0.000 description 1
- YGHNCEWNRJLHGD-UHFFFAOYSA-N 2-[hexyl(propyl)amino]phenol Chemical compound CCCCCCN(CCC)C1=CC=CC=C1O YGHNCEWNRJLHGD-UHFFFAOYSA-N 0.000 description 1
- ZWKXECDMHQUWGL-UHFFFAOYSA-N 2-[methyl(oxolan-2-ylmethyl)amino]phenol Chemical compound C=1C=CC=C(O)C=1N(C)CC1CCCO1 ZWKXECDMHQUWGL-UHFFFAOYSA-N 0.000 description 1
- GONXLEDSOQHRRY-UHFFFAOYSA-N 2-[methyl(pentan-2-yl)amino]phenol Chemical compound CCCC(C)N(C)C1=CC=CC=C1O GONXLEDSOQHRRY-UHFFFAOYSA-N 0.000 description 1
- ZZJSRJYQKOYDOH-UHFFFAOYSA-N 2-[methyl(pentyl)amino]phenol Chemical compound CCCCCN(C)C1=CC=CC=C1O ZZJSRJYQKOYDOH-UHFFFAOYSA-N 0.000 description 1
- XTXUVXTUVUOJDV-UHFFFAOYSA-N 2-[methyl(propyl)amino]phenol Chemical compound CCCN(C)C1=CC=CC=C1O XTXUVXTUVUOJDV-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- OXELIFPFCCGAJX-UHFFFAOYSA-N 2-piperidin-1-ylphenol Chemical compound OC1=CC=CC=C1N1CCCCC1 OXELIFPFCCGAJX-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- MSEXTEOIXRLZTC-UHFFFAOYSA-N 3-amino-2,4-dibutylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1N MSEXTEOIXRLZTC-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 238000005119 centrifugation Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006623 cyclooctylmethyl group Chemical group 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
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/3275—Fluoran compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01811051 | 2001-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200402622B true ZA200402622B (en) | 2006-05-31 |
Family
ID=8184215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200402622A ZA200402622B (en) | 2001-10-26 | 2004-04-02 | Production of keto acids |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20040242891A1 (pt) |
| EP (1) | EP1442009A1 (pt) |
| JP (1) | JP2005507416A (pt) |
| CN (1) | CN1301962C (pt) |
| BR (1) | BR0213487A (pt) |
| CA (1) | CA2463156A1 (pt) |
| IL (1) | IL161288A0 (pt) |
| MX (1) | MXPA04003693A (pt) |
| WO (1) | WO2003037846A1 (pt) |
| ZA (1) | ZA200402622B (pt) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10319450A1 (de) * | 2003-04-30 | 2004-11-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmazeutische Formulierung des Telmisartan Natriumsalzes |
| US9029363B2 (en) | 2003-04-30 | 2015-05-12 | Boehringer Ingelheim International Gmbh | Telmisartan sodium salt pharmaceutical formulation |
| CN102503847B (zh) * | 2011-10-26 | 2015-09-16 | 河北建新化工股份有限公司 | 二苯酮酸类化合物的制备方法 |
| CN106349091A (zh) * | 2016-08-30 | 2017-01-25 | 沈阳化工大学 | 一种熔融态合成2‑（4‑二乙氨基‑2‑羟基苯甲酰基）苯甲酸的方法 |
| WO2018228981A1 (en) * | 2017-06-14 | 2018-12-20 | Sabic Global Technologies B.V. | Process for mono n-alkylation of aminophenol |
| CN109946353A (zh) * | 2018-11-08 | 2019-06-28 | 利多(香港)有限公司 | 电势型生物传感器和检测方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE87068C (pt) * | ||||
| GB2014629A (en) * | 1978-02-16 | 1979-08-30 | Ciba Geigy Ag | Pressure-sensitive Recording Material |
| JP3501816B2 (ja) * | 1991-04-25 | 2004-03-02 | 三井化学株式会社 | ケト酸の製造方法 |
| US5371285A (en) * | 1991-04-25 | 1994-12-06 | Mitsui Petrochemical Industries, Ltd. | Method of producing keto acids |
| ES2105191T3 (es) * | 1992-03-17 | 1997-10-16 | Ciba Geigy Ag | Compuestos cromogenos de fluorano. |
| GB9700375D0 (en) * | 1997-01-09 | 1997-02-26 | Ciba Geigy Ag | Purification process |
| WO2000026037A1 (en) * | 1998-10-30 | 2000-05-11 | Ciba Specialty Chemicals Holding Inc. | Heat sensitive recording material |
-
2002
- 2002-10-17 CA CA002463156A patent/CA2463156A1/en not_active Abandoned
- 2002-10-17 JP JP2003540129A patent/JP2005507416A/ja not_active Withdrawn
- 2002-10-17 MX MXPA04003693A patent/MXPA04003693A/es active IP Right Grant
- 2002-10-17 CN CNB028210492A patent/CN1301962C/zh not_active Expired - Fee Related
- 2002-10-17 IL IL16128802A patent/IL161288A0/xx unknown
- 2002-10-17 EP EP02785236A patent/EP1442009A1/en not_active Withdrawn
- 2002-10-17 BR BR0213487-0A patent/BR0213487A/pt not_active Application Discontinuation
- 2002-10-17 US US10/492,467 patent/US20040242891A1/en not_active Abandoned
- 2002-10-17 WO PCT/EP2002/011647 patent/WO2003037846A1/en not_active Application Discontinuation
-
2004
- 2004-04-02 ZA ZA200402622A patent/ZA200402622B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1575274A (zh) | 2005-02-02 |
| EP1442009A1 (en) | 2004-08-04 |
| CN1301962C (zh) | 2007-02-28 |
| JP2005507416A (ja) | 2005-03-17 |
| IL161288A0 (en) | 2004-09-27 |
| BR0213487A (pt) | 2004-11-03 |
| US20040242891A1 (en) | 2004-12-02 |
| WO2003037846A1 (en) | 2003-05-08 |
| CA2463156A1 (en) | 2003-05-08 |
| MXPA04003693A (es) | 2004-07-30 |
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