FR2475536A2 - Procede de preparation de l'acide di-n-propylacetique et de ses sels de metaux alcalins - Google Patents
Procede de preparation de l'acide di-n-propylacetique et de ses sels de metaux alcalins Download PDFInfo
- Publication number
- FR2475536A2 FR2475536A2 FR8003115A FR8003115A FR2475536A2 FR 2475536 A2 FR2475536 A2 FR 2475536A2 FR 8003115 A FR8003115 A FR 8003115A FR 8003115 A FR8003115 A FR 8003115A FR 2475536 A2 FR2475536 A2 FR 2475536A2
- Authority
- FR
- France
- Prior art keywords
- acid
- preparation
- dipropylacetic
- medium
- hydrolysis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- -1 ALKALI METAL SALTS Chemical class 0.000 title description 2
- 229910052783 alkali metal Inorganic materials 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 10
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 229940016681 dipropylacetamide Drugs 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 27
- 229940005605 valeric acid Drugs 0.000 description 13
- 239000002253 acid Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 5
- 239000008213 purified water Substances 0.000 description 4
- 238000012549 training Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 3
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 208000026435 phlegm Diseases 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 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)
Priority Applications (23)
| 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 |
| ZA00810707A ZA81707B (en) | 1980-02-13 | 1981-02-03 | Process for preparing acetic acid derivatives |
| NZ196174A NZ196174A (en) | 1980-02-13 | 1981-02-03 | Preparation of di-n-propyl acetic acid |
| DE19813103776 DE3103776A1 (de) | 1977-03-15 | 1981-02-04 | Verfahren zur herstellung von di-n-propyl-essigsaeure |
| IL6206381A IL62063A (en) | 1977-05-05 | 1981-02-04 | Process for the preparation of di-n-propyl-acetic acid and salts thereof |
| MX10154281U MX6215E (es) | 1980-02-13 | 1981-02-06 | Procedimiento mejorado para preparar acido di-n-propilacetico |
| DK053781A DK154640C (da) | 1980-02-13 | 1981-02-06 | Fremgangsmaade til fremstilling af di-n-propleddikesyre |
| CH88681A CH646681A5 (fr) | 1980-02-13 | 1981-02-10 | Procede pour la preparation de l'acide di-n-propylacetique et de ses sels. |
| NL8100623A NL191439C (nl) | 1980-02-13 | 1981-02-10 | Werkwijze voor het bereiden van di-n-propylazijnzuur. |
| CS811001A CS217992B2 (en) | 1980-02-13 | 1981-02-11 | Method of making the di-n-propylvinegar acid |
| PT72486A PT72486B (en) | 1980-02-13 | 1981-02-11 | Process for the preparation of acetic acid derivatives |
| GB8104287A GB2068962B (en) | 1980-02-13 | 1981-02-11 | Process for preparing valproic acid |
| AU67226/81A AU535655B2 (en) | 1980-02-13 | 1981-02-12 | Du-npropyl acetic acid |
| YU36081A YU42379B (en) | 1977-03-15 | 1981-02-12 | Process for obtaining di-n-propylacetic acid |
| PL1981229649A PL129543B3 (en) | 1980-02-13 | 1981-02-12 | Process for preparing di-n-propylacetic acid |
| IE264/81A IE50863B1 (en) | 1980-02-13 | 1981-02-12 | Process for preparing acetic acid derivatives |
| ES499362A ES8301873A2 (es) | 1980-02-13 | 1981-02-12 | Procedimiento para preparar acido di-n-propilacetico |
| GR64108A GR73151B (cs) | 1980-02-13 | 1981-02-12 | |
| AR284274A AR225211A1 (es) | 1980-02-13 | 1981-02-12 | Un procedimiento para preparar acido di-n-propilacetico |
| BE0/203775A BE887492A (fr) | 1980-02-13 | 1981-02-12 | Procede pour la preparation de derives d'acide acetique |
| SU813248453A SU1060103A4 (ru) | 1980-02-13 | 1981-02-12 | Способ получени ди-н-пропилуксусной кислоты |
| IT8119684A IT1210984B (it) | 1980-02-13 | 1981-02-12 | Procedimento per la preparazione di un derivato dell'acido acetico. |
| AT0069381A AT370718B (de) | 1980-02-13 | 1981-02-13 | Verfahren zur herstellung von di-n -propylessigsaeure |
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 |
|---|---|
| FR2475536A2 true FR2475536A2 (fr) | 1981-08-14 |
| FR2475536B2 FR2475536B2 (cs) | 1985-05-24 |
Family
ID=9238525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8003115A Granted FR2475536A2 (fr) | 1977-03-15 | 1980-02-13 | Procede de preparation de l'acide di-n-propylacetique et de ses sels de metaux alcalins |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR225211A1 (cs) |
| AT (1) | AT370718B (cs) |
| AU (1) | AU535655B2 (cs) |
| BE (1) | BE887492A (cs) |
| CH (1) | CH646681A5 (cs) |
| CS (1) | CS217992B2 (cs) |
| DK (1) | DK154640C (cs) |
| ES (1) | ES8301873A2 (cs) |
| FR (1) | FR2475536A2 (cs) |
| GB (1) | GB2068962B (cs) |
| GR (1) | GR73151B (cs) |
| IE (1) | IE50863B1 (cs) |
| IT (1) | IT1210984B (cs) |
| NL (1) | NL191439C (cs) |
| NZ (1) | NZ196174A (cs) |
| PL (1) | PL129543B3 (cs) |
| PT (1) | PT72486B (cs) |
| SU (1) | SU1060103A4 (cs) |
| ZA (1) | ZA81707B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CN118373735B (zh) * | 2024-04-11 | 2025-02-21 | 湖南省湘中制药有限公司 | 一种氰基乙酸酯法制备丙戊酸 |
-
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 PL PL1981229649A patent/PL129543B3/pl unknown
- 1981-02-12 AU AU67226/81A patent/AU535655B2/en not_active Expired
- 1981-02-12 IT IT8119684A patent/IT1210984B/it active
- 1981-02-12 AR AR284274A patent/AR225211A1/es active
- 1981-02-12 GR GR64108A patent/GR73151B/el unknown
- 1981-02-12 IE IE264/81A patent/IE50863B1/en not_active IP Right Cessation
- 1981-02-12 BE BE0/203775A patent/BE887492A/fr not_active IP Right Cessation
- 1981-02-12 SU SU813248453A patent/SU1060103A4/ru active
- 1981-02-12 ES ES499362A patent/ES8301873A2/es not_active Expired
- 1981-02-13 AT AT0069381A patent/AT370718B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2475536B2 (cs) | 1985-05-24 |
| ES499362A0 (es) | 1983-01-16 |
| DK53781A (da) | 1981-08-14 |
| SU1060103A4 (ru) | 1983-12-07 |
| AR225211A1 (es) | 1982-02-26 |
| PT72486A (en) | 1981-03-01 |
| CH646681A5 (fr) | 1984-12-14 |
| ATA69381A (de) | 1982-09-15 |
| CS217992B2 (en) | 1983-02-25 |
| IE50863B1 (en) | 1986-08-06 |
| NL191439C (nl) | 1995-07-04 |
| AU535655B2 (en) | 1984-03-29 |
| NZ196174A (en) | 1983-05-10 |
| NL8100623A (nl) | 1981-09-16 |
| ES8301873A2 (es) | 1983-01-16 |
| PL229649A3 (cs) | 1982-05-24 |
| GB2068962A (en) | 1981-08-19 |
| ZA81707B (en) | 1982-02-24 |
| IT1210984B (it) | 1989-09-29 |
| AU6722681A (en) | 1981-08-20 |
| AT370718B (de) | 1983-04-25 |
| GR73151B (cs) | 1984-02-10 |
| IE810264L (en) | 1981-08-13 |
| DK154640B (da) | 1988-12-05 |
| PT72486B (en) | 1982-02-05 |
| BE887492A (fr) | 1981-08-12 |
| NL191439B (nl) | 1995-03-01 |
| PL129543B3 (en) | 1984-05-31 |
| DK154640C (da) | 1989-05-22 |
| GB2068962B (en) | 1983-10-12 |
| IT8119684A0 (it) | 1981-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CA | Change of address | ||
| CD | Change of name or company name |