SU571185A3 - Способ выделени -изомера 2(6-метокси-2-нафтил)-пропионовой кислоты из его смеси - Google Patents
Способ выделени -изомера 2(6-метокси-2-нафтил)-пропионовой кислоты из его смесиInfo
- Publication number
- SU571185A3 SU571185A3 SU7301905966A SU1905966A SU571185A3 SU 571185 A3 SU571185 A3 SU 571185A3 SU 7301905966 A SU7301905966 A SU 7301905966A SU 1905966 A SU1905966 A SU 1905966A SU 571185 A3 SU571185 A3 SU 571185A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- isomer
- naphthyl
- methoxy
- propionic acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 16
- 239000002253 acid Substances 0.000 title claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 20
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- ZGWVFTHCCKENBK-UHFFFAOYSA-N guanidine;zinc Chemical compound [Zn].NC(N)=N ZGWVFTHCCKENBK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 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 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- 239000000706 filtrate Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- BSQPJKMLKCWQOE-UHFFFAOYSA-N 2-(1-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=CC=C2C(OC)=C(C(C)C(O)=O)C=CC2=C1 BSQPJKMLKCWQOE-UHFFFAOYSA-N 0.000 claims 1
- 241000723347 Cinnamomum Species 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 235000017803 cinnamon Nutrition 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- 239000008235 industrial water Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 claims 1
- 229910001950 potassium oxide Inorganic materials 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- -1 glycol ethers Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XQMPFCWHEKIBNV-UHFFFAOYSA-N 2-(6-methoxynaphthalen-1-yl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC2=CC(OC)=CC=C21 XQMPFCWHEKIBNV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QESCHNIJDGQPJN-UHFFFAOYSA-N dimethylamino(oxo)methanesulfonic acid Chemical compound CN(C)C(=O)S(O)(=O)=O QESCHNIJDGQPJN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 230000004572 zinc-binding Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24646172A | 1972-04-21 | 1972-04-21 | |
| US35019373A | 1973-04-11 | 1973-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU571185A3 true SU571185A3 (ru) | 1977-08-30 |
Family
ID=26937998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7301905966A SU571185A3 (ru) | 1972-04-21 | 1973-04-20 | Способ выделени -изомера 2(6-метокси-2-нафтил)-пропионовой кислоты из его смеси |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR200998A1 (cs) |
| AT (1) | AT325031B (cs) |
| CA (1) | CA995676A (cs) |
| CH (1) | CH574884A5 (cs) |
| CS (1) | CS161980B2 (cs) |
| DE (1) | DE2319245C3 (cs) |
| DK (1) | DK139715B (cs) |
| ES (1) | ES413924A2 (cs) |
| FI (1) | FI57927C (cs) |
| GB (1) | GB1422015A (cs) |
| HU (1) | HU166932B (cs) |
| IE (1) | IE37553B1 (cs) |
| IL (1) | IL42078A (cs) |
| IN (1) | IN138786B (cs) |
| IT (1) | IT1044244B (cs) |
| NL (1) | NL164549C (cs) |
| SE (1) | SE406083B (cs) |
| SU (1) | SU571185A3 (cs) |
| YU (1) | YU36678B (cs) |
-
1973
- 1973-04-13 IN IN878/CAL/73A patent/IN138786B/en unknown
- 1973-04-13 CA CA168,713A patent/CA995676A/en not_active Expired
- 1973-04-16 DE DE2319245A patent/DE2319245C3/de not_active Expired
- 1973-04-18 NL NL7305486.A patent/NL164549C/xx not_active IP Right Cessation
- 1973-04-18 AR AR247626A patent/AR200998A1/es active
- 1973-04-18 DK DK218673AA patent/DK139715B/da not_active IP Right Cessation
- 1973-04-18 FI FI1261/73A patent/FI57927C/fi active
- 1973-04-18 GB GB1881573A patent/GB1422015A/en not_active Expired
- 1973-04-19 YU YU1058/73A patent/YU36678B/xx unknown
- 1973-04-19 ES ES413924A patent/ES413924A2/es not_active Expired
- 1973-04-19 IE IE632/73A patent/IE37553B1/xx unknown
- 1973-04-19 SE SE7305624A patent/SE406083B/xx unknown
- 1973-04-19 CH CH565073A patent/CH574884A5/xx not_active IP Right Cessation
- 1973-04-20 SU SU7301905966A patent/SU571185A3/ru active
- 1973-04-20 CS CS2907A patent/CS161980B2/cs unknown
- 1973-04-20 HU HUSI1314A patent/HU166932B/hu unknown
- 1973-04-20 IT IT68148/73A patent/IT1044244B/it active
- 1973-04-20 AT AT356773A patent/AT325031B/de not_active IP Right Cessation
- 1973-04-20 IL IL42078A patent/IL42078A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN138786B (cs) | 1976-03-27 |
| NL164549C (nl) | 1981-01-15 |
| IE37553L (en) | 1973-10-21 |
| ES413924A2 (es) | 1976-11-16 |
| DK139715C (cs) | 1979-09-17 |
| CS161980B2 (cs) | 1975-06-10 |
| DK139715B (da) | 1979-04-02 |
| NL164549B (nl) | 1980-08-15 |
| IL42078A (en) | 1976-08-31 |
| YU105873A (en) | 1982-06-18 |
| HU166932B (cs) | 1975-06-28 |
| AR200998A1 (es) | 1975-02-06 |
| DE2319245C3 (de) | 1978-12-07 |
| FI57927C (fi) | 1980-11-10 |
| SE406083B (sv) | 1979-01-22 |
| CH574884A5 (cs) | 1976-04-30 |
| FI57927B (fi) | 1980-07-31 |
| NL7305486A (cs) | 1973-10-23 |
| YU36678B (en) | 1984-08-31 |
| DE2319245A1 (de) | 1973-10-25 |
| IE37553B1 (en) | 1977-08-17 |
| CA995676A (en) | 1976-08-24 |
| AT325031B (de) | 1975-09-25 |
| DE2319245B2 (de) | 1978-04-06 |
| GB1422015A (en) | 1976-01-21 |
| IT1044244B (it) | 1980-03-20 |
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