PL129543B3 - Process for preparing di-n-propylacetic acid - Google Patents
Process for preparing di-n-propylacetic acid Download PDFInfo
- Publication number
- PL129543B3 PL129543B3 PL1981229649A PL22964981A PL129543B3 PL 129543 B3 PL129543 B3 PL 129543B3 PL 1981229649 A PL1981229649 A PL 1981229649A PL 22964981 A PL22964981 A PL 22964981A PL 129543 B3 PL129543 B3 PL 129543B3
- Authority
- PL
- Poland
- Prior art keywords
- acid
- sulfuric acid
- sodium
- scheme
- hydrolysis
- Prior art date
Links
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 6
- -1 alkali metal salts Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010586 diagram Methods 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims 1
- IVYXLCYENQNVHM-UHFFFAOYSA-N 2,2-diphenylpentanoic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(CCC)C1=CC=CC=C1 IVYXLCYENQNVHM-UHFFFAOYSA-N 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 20
- 229940005605 valeric acid Drugs 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 3
- YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus 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
- 239000000356 contaminant Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8003115A FR2475536A2 (fr) | 1980-02-13 | 1980-02-13 | Procede de preparation de l'acide di-n-propylacetique et de ses sels de metaux alcalins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL229649A3 PL229649A3 (US06566495-20030520-M00011.png) | 1982-05-24 |
| PL129543B3 true PL129543B3 (en) | 1984-05-31 |
Family
ID=9238525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981229649A PL129543B3 (en) | 1980-02-13 | 1981-02-12 | Process for preparing di-n-propylacetic acid |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113200848A (zh) * | 2021-03-29 | 2021-08-03 | 上海青平药业有限公司 | 一种丙戊酸制备新方法 |
| CN113173845A (zh) * | 2021-03-29 | 2021-07-27 | 上海青平药业有限公司 | 一种制备丙戊酸的方法 |
-
1980
- 1980-02-13 FR FR8003115A patent/FR2475536A2/fr active Granted
-
1981
- 1981-02-03 NZ NZ196174A patent/NZ196174A/xx unknown
- 1981-02-03 ZA ZA00810707A patent/ZA81707B/xx unknown
- 1981-02-06 DK DK053781A patent/DK154640C/da not_active IP Right Cessation
- 1981-02-10 CH CH88681A patent/CH646681A5/fr not_active IP Right Cessation
- 1981-02-10 NL NL8100623A patent/NL191439C/xx not_active IP Right Cessation
- 1981-02-11 GB GB8104287A patent/GB2068962B/en not_active Expired
- 1981-02-11 CS CS811001A patent/CS217992B2/cs unknown
- 1981-02-11 PT PT72486A patent/PT72486B/pt unknown
- 1981-02-12 BE BE0/203775A patent/BE887492A/fr not_active IP Right Cessation
- 1981-02-12 AR AR284274A patent/AR225211A1/es active
- 1981-02-12 PL PL1981229649A patent/PL129543B3/pl unknown
- 1981-02-12 GR GR64108A patent/GR73151B/el unknown
- 1981-02-12 ES ES1981499362A patent/ES499362A0/es active Granted
- 1981-02-12 AU AU67226/81A patent/AU535655B2/en not_active Expired
- 1981-02-12 SU SU813248453A patent/SU1060103A4/ru active
- 1981-02-12 IT IT8119684A patent/IT1210984B/it active
- 1981-02-12 IE IE264/81A patent/IE50863B1/en not_active IP Right Cessation
- 1981-02-13 AT AT0069381A patent/AT370718B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES8301873A2 (es) | 1983-01-16 |
| CH646681A5 (fr) | 1984-12-14 |
| DK154640C (da) | 1989-05-22 |
| DK53781A (da) | 1981-08-14 |
| PT72486A (en) | 1981-03-01 |
| CS217992B2 (en) | 1983-02-25 |
| PT72486B (en) | 1982-02-05 |
| BE887492A (fr) | 1981-08-12 |
| IE50863B1 (en) | 1986-08-06 |
| AU6722681A (en) | 1981-08-20 |
| AR225211A1 (es) | 1982-02-26 |
| FR2475536B2 (US06566495-20030520-M00011.png) | 1985-05-24 |
| NL191439B (nl) | 1995-03-01 |
| NL191439C (nl) | 1995-07-04 |
| PL229649A3 (US06566495-20030520-M00011.png) | 1982-05-24 |
| GR73151B (US06566495-20030520-M00011.png) | 1984-02-10 |
| ZA81707B (en) | 1982-02-24 |
| DK154640B (da) | 1988-12-05 |
| IT1210984B (it) | 1989-09-29 |
| ES499362A0 (es) | 1983-01-16 |
| NL8100623A (nl) | 1981-09-16 |
| IE810264L (en) | 1981-08-13 |
| ATA69381A (de) | 1982-09-15 |
| AU535655B2 (en) | 1984-03-29 |
| GB2068962B (en) | 1983-10-12 |
| FR2475536A2 (fr) | 1981-08-14 |
| NZ196174A (en) | 1983-05-10 |
| AT370718B (de) | 1983-04-25 |
| IT8119684A0 (it) | 1981-02-12 |
| GB2068962A (en) | 1981-08-19 |
| SU1060103A4 (ru) | 1983-12-07 |
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