BE498859A - - Google Patents
Info
- Publication number
- BE498859A BE498859A BE498859DA BE498859A BE 498859 A BE498859 A BE 498859A BE 498859D A BE498859D A BE 498859DA BE 498859 A BE498859 A BE 498859A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- oxyaminobenzoic
- acids
- temperatures
- halogenated
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 52
- 150000002148 esters Chemical class 0.000 claims description 24
- 150000007513 acids Chemical class 0.000 claims description 23
- -1 N-substituted aminoalcohols Chemical class 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001414 amino alcohols Chemical group 0.000 description 9
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N Diethylethanolamine Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000001131 transforming Effects 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-Chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XIGLAOSAMPKYTP-UHFFFAOYSA-N [N+](=O)([O-])C1=C(CNC(C)O)C=CC=C1 Chemical compound [N+](=O)([O-])C1=C(CNC(C)O)C=CC=C1 XIGLAOSAMPKYTP-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229940075930 picrate Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2S)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- ODFURSVUPUXGCI-UHFFFAOYSA-N 1-(dibenzylamino)ethanol Chemical compound C=1C=CC=CC=1CN(C(O)C)CC1=CC=CC=C1 ODFURSVUPUXGCI-UHFFFAOYSA-N 0.000 description 1
- COKMLVOGWBEPNX-UHFFFAOYSA-N 1-(dipropylamino)ethanol Chemical compound CCCN(C(C)O)CCC COKMLVOGWBEPNX-UHFFFAOYSA-N 0.000 description 1
- LEYYLQKYOZYCRF-UHFFFAOYSA-N 1-(hexylamino)ethanol Chemical compound CCCCCCNC(C)O LEYYLQKYOZYCRF-UHFFFAOYSA-N 0.000 description 1
- OZHIYEINSCNALY-UHFFFAOYSA-N 1-aminobutan-1-ol Chemical class CCCC(N)O OZHIYEINSCNALY-UHFFFAOYSA-N 0.000 description 1
- NPEIGRBGMUJNFE-UHFFFAOYSA-N 1-aminohexan-1-ol Chemical class CCCCCC(N)O NPEIGRBGMUJNFE-UHFFFAOYSA-N 0.000 description 1
- WGAOZGUUHIBABN-UHFFFAOYSA-N 1-aminopentan-1-ol Chemical class CCCCC(N)O WGAOZGUUHIBABN-UHFFFAOYSA-N 0.000 description 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 1-aminopropan-1-ol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
- ULZRKSDAMUWQEZ-UHFFFAOYSA-N 1-anilinoethanol Chemical compound CC(O)NC1=CC=CC=C1 ULZRKSDAMUWQEZ-UHFFFAOYSA-N 0.000 description 1
- CMQZETQFZHIYJG-UHFFFAOYSA-N 2-(N-phenylanilino)ethanol Chemical compound C=1C=CC=CC=1N(CCO)C1=CC=CC=C1 CMQZETQFZHIYJG-UHFFFAOYSA-N 0.000 description 1
- HZLYGAQNCRJBDT-UHFFFAOYSA-N 2-(ethylamino)propan-2-ol Chemical compound CCNC(C)(C)O HZLYGAQNCRJBDT-UHFFFAOYSA-N 0.000 description 1
- MVLIVYYZHZKKQF-UHFFFAOYSA-N 2-(propylamino)propan-2-ol Chemical compound CCCNC(C)(C)O MVLIVYYZHZKKQF-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N 2-Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-N,N-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-bromopropan-1-ol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- CBJCOUAIXAWRQN-UHFFFAOYSA-N 3-chloro-2-phenylpropan-1-ol Chemical compound OCC(CCl)C1=CC=CC=C1 CBJCOUAIXAWRQN-UHFFFAOYSA-N 0.000 description 1
- 229940000641 4-Aminobenzoic Acid Drugs 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-Aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-N-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- LEWAAIPRLZCGGD-UHFFFAOYSA-N C(C)C(C)(O)NC(C)C Chemical compound C(C)C(C)(O)NC(C)C LEWAAIPRLZCGGD-UHFFFAOYSA-N 0.000 description 1
- KAGJBGNPHJPTJV-UHFFFAOYSA-N C(C)C1=CC=C(C=C1)CC(O)(N)C1=CC=C(C=C1)CC Chemical compound C(C)C1=CC=C(C=C1)CC(O)(N)C1=CC=C(C=C1)CC KAGJBGNPHJPTJV-UHFFFAOYSA-N 0.000 description 1
- PDISYOQMRIODAI-UHFFFAOYSA-N C1(=CC=CC=C1)CCCC(O)(N)CCC1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)CCCC(O)(N)CCC1=CC=CC=C1 PDISYOQMRIODAI-UHFFFAOYSA-N 0.000 description 1
- 229960003563 Calcium Carbonate Drugs 0.000 description 1
- 229960002887 Deanol Drugs 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N Isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N N,N-Diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 1
- MRBBWZVZGJDZBI-UHFFFAOYSA-N N-benzyl-3-chloropropan-1-amine Chemical compound ClCCCNCC1=CC=CC=C1 MRBBWZVZGJDZBI-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000003444 anaesthetic Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- JCIJQBHESSRAOT-UHFFFAOYSA-N methyl 4-(4-aminobenzoyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)C1=CC=C(N)C=C1 JCIJQBHESSRAOT-UHFFFAOYSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE498859A true BE498859A (ko) |
Family
ID=141417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE498859D BE498859A (ko) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE498859A (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029274A (en) * | 1949-10-22 | 1962-04-10 | Rheinpreussen Ag | Alkamine esters of amino salicylic acid |
| US3134805A (en) * | 1954-10-15 | 1964-05-26 | Sterling Drug Inc | Preparation of tertiary-aminoalkyl amino-alkoxybenzoates |
-
0
- BE BE498859D patent/BE498859A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029274A (en) * | 1949-10-22 | 1962-04-10 | Rheinpreussen Ag | Alkamine esters of amino salicylic acid |
| US3134805A (en) * | 1954-10-15 | 1964-05-26 | Sterling Drug Inc | Preparation of tertiary-aminoalkyl amino-alkoxybenzoates |
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