PL93841B1 - - Google Patents
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- Publication number
- PL93841B1 PL93841B1 PL17235774A PL17235774A PL93841B1 PL 93841 B1 PL93841 B1 PL 93841B1 PL 17235774 A PL17235774 A PL 17235774A PL 17235774 A PL17235774 A PL 17235774A PL 93841 B1 PL93841 B1 PL 93841B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- water
- alkyl
- aldehyde
- phenylpropionic
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 claims description 9
- 229960002218 sodium chlorite Drugs 0.000 claims description 9
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 claims 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000003791 organic solvent mixture Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 5
- YHEYEPDRELFHFM-UHFFFAOYSA-N 2-methyl-2-phenylhexanoic acid Chemical compound CCCCC(C)(C(O)=O)C1=CC=CC=C1 YHEYEPDRELFHFM-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl radical Chemical group 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910001923 silver oxide Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL17235774A PL93841B1 (cs) | 1974-07-01 | 1974-07-01 | |
| YU166275A YU36480B (en) | 1974-07-01 | 1975-06-27 | Process for obtaining alpha-phenylpropionic acid |
| SU752149407A SU691074A3 (ru) | 1974-07-01 | 1975-06-30 | Способ получени -фенилпропионовой кислоты |
| DD18700975A DD118605A5 (cs) | 1974-07-01 | 1975-07-01 | |
| RO7582723A RO67241A (ro) | 1974-07-01 | 1975-07-01 | Procedeu pentru prepararea derivatilor acidului alfa-fenilpropionic |
| CS466375A CS198169B2 (cs) | 1974-07-01 | 1975-07-01 | Způsob výroby derivátů kyseliny a-řenyipropianové |
| HU75PO00000592A HU172065B (hu) | 1974-07-01 | 1975-07-01 | Sposob poluchenija proizvodnykh al'fa-fenil-propionovoj kisloty |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL17235774A PL93841B1 (cs) | 1974-07-01 | 1974-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL93841B1 true PL93841B1 (cs) | 1977-06-30 |
Family
ID=19968031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17235774A PL93841B1 (cs) | 1974-07-01 | 1974-07-01 |
Country Status (7)
| Country | Link |
|---|---|
| CS (1) | CS198169B2 (cs) |
| DD (1) | DD118605A5 (cs) |
| HU (1) | HU172065B (cs) |
| PL (1) | PL93841B1 (cs) |
| RO (1) | RO67241A (cs) |
| SU (1) | SU691074A3 (cs) |
| YU (1) | YU36480B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63500241A (ja) * | 1985-07-12 | 1988-01-28 | ジ・アップジョン・カンパニ− | フルルビプロフェン製法 |
-
1974
- 1974-07-01 PL PL17235774A patent/PL93841B1/pl unknown
-
1975
- 1975-06-27 YU YU166275A patent/YU36480B/xx unknown
- 1975-06-30 SU SU752149407A patent/SU691074A3/ru active
- 1975-07-01 RO RO7582723A patent/RO67241A/ro unknown
- 1975-07-01 CS CS466375A patent/CS198169B2/cs unknown
- 1975-07-01 HU HU75PO00000592A patent/HU172065B/hu not_active IP Right Cessation
- 1975-07-01 DD DD18700975A patent/DD118605A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU691074A3 (ru) | 1979-10-05 |
| CS198169B2 (cs) | 1980-05-30 |
| YU36480B (en) | 1984-02-29 |
| DD118605A5 (cs) | 1976-03-12 |
| HU172065B (hu) | 1978-05-28 |
| RO67241A (ro) | 1980-04-15 |
| YU166275A (en) | 1982-02-25 |
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