SU1060103A4 - Способ получени ди-н-пропилуксусной кислоты - Google Patents
Способ получени ди-н-пропилуксусной кислоты Download PDFInfo
- Publication number
- SU1060103A4 SU1060103A4 SU813248453A SU3248453A SU1060103A4 SU 1060103 A4 SU1060103 A4 SU 1060103A4 SU 813248453 A SU813248453 A SU 813248453A SU 3248453 A SU3248453 A SU 3248453A SU 1060103 A4 SU1060103 A4 SU 1060103A4
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- propyl
- temperature
- propylacetic
- hydrolysis
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims abstract description 43
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 35
- YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- UZRGQIZTJOPZGE-UHFFFAOYSA-N 2-cyano-2-propylpentanoic acid Chemical compound CCCC(C(O)=O)(C#N)CCC UZRGQIZTJOPZGE-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000006114 decarboxylation reaction Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 claims 1
- 238000001256 steam distillation Methods 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract description 23
- 238000010992 reflux Methods 0.000 abstract description 11
- 229940005605 valeric acid Drugs 0.000 abstract description 11
- 239000012535 impurity Substances 0.000 abstract description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000004821 distillation Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 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 description 5
- 239000012153 distilled water Substances 0.000 description 5
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- -1 cyanoacetic acid ester Chemical class 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- IHPHPGLJYCDONF-UHFFFAOYSA-N Essigsaeure-propylamid Natural products CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- PBQCXUKFGKOTTE-UHFFFAOYSA-N n-propylacetamide Chemical compound [CH2]CCNC(C)=O PBQCXUKFGKOTTE-UHFFFAOYSA-N 0.000 description 2
- 229940005654 nitrite ion Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NICLKHGIKDZZGV-UHFFFAOYSA-N 2-cyanopentanoic acid Chemical compound CCCC(C#N)C(O)=O NICLKHGIKDZZGV-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 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
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- YRRFBANPGRXQNJ-UHFFFAOYSA-M acetyl(trimethyl)azanium;bromide Chemical compound [Br-].CC(=O)[N+](C)(C)C YRRFBANPGRXQNJ-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000012840 feeding operation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- BVJUXXYBIMHHDW-UHFFFAOYSA-N iodane Chemical compound I.I BVJUXXYBIMHHDW-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- SMBGWMJTOOLQHN-UHFFFAOYSA-N lead;sulfuric acid Chemical compound [Pb].OS(O)(=O)=O SMBGWMJTOOLQHN-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 235000016788 valerian Nutrition 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 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU703013 Addition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1060103A4 true SU1060103A4 (ru) | 1983-12-07 |
Family
ID=9238525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813248453A SU1060103A4 (ru) | 1980-02-13 | 1981-02-12 | Способ получени ди-н-пропилуксусной кислоты |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR225211A1 (enExample) |
| AT (1) | AT370718B (enExample) |
| AU (1) | AU535655B2 (enExample) |
| BE (1) | BE887492A (enExample) |
| CH (1) | CH646681A5 (enExample) |
| CS (1) | CS217992B2 (enExample) |
| DK (1) | DK154640C (enExample) |
| ES (1) | ES8301873A2 (enExample) |
| FR (1) | FR2475536A2 (enExample) |
| GB (1) | GB2068962B (enExample) |
| GR (1) | GR73151B (enExample) |
| IE (1) | IE50863B1 (enExample) |
| IT (1) | IT1210984B (enExample) |
| NL (1) | NL191439C (enExample) |
| NZ (1) | NZ196174A (enExample) |
| PL (1) | PL129543B3 (enExample) |
| PT (1) | PT72486B (enExample) |
| SU (1) | SU1060103A4 (enExample) |
| ZA (1) | ZA81707B (enExample) |
Families Citing this family (3)
| 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 |
| 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 ZA ZA00810707A patent/ZA81707B/xx unknown
- 1981-02-03 NZ NZ196174A patent/NZ196174A/xx unknown
- 1981-02-06 DK DK053781A patent/DK154640C/da not_active IP Right Cessation
- 1981-02-10 NL NL8100623A patent/NL191439C/xx not_active IP Right Cessation
- 1981-02-10 CH CH88681A patent/CH646681A5/fr not_active IP Right Cessation
- 1981-02-11 CS CS811001A patent/CS217992B2/cs unknown
- 1981-02-11 GB GB8104287A patent/GB2068962B/en not_active Expired
- 1981-02-11 PT PT72486A patent/PT72486B/pt unknown
- 1981-02-12 ES ES499362A patent/ES8301873A2/es not_active Expired
- 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 GR GR64108A patent/GR73151B/el unknown
- 1981-02-12 AR AR284274A patent/AR225211A1/es active
- 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
- 1981-02-13 AT AT0069381A patent/AT370718B/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| 1. Патент СССР W 703013, кл. С 07 С 53/126, 1977 (прототип). * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2475536A2 (fr) | 1981-08-14 |
| ES499362A0 (es) | 1983-01-16 |
| ZA81707B (en) | 1982-02-24 |
| GB2068962A (en) | 1981-08-19 |
| PT72486B (en) | 1982-02-05 |
| IT1210984B (it) | 1989-09-29 |
| AU6722681A (en) | 1981-08-20 |
| DK53781A (da) | 1981-08-14 |
| ES8301873A2 (es) | 1983-01-16 |
| DK154640C (da) | 1989-05-22 |
| CH646681A5 (fr) | 1984-12-14 |
| NL191439C (nl) | 1995-07-04 |
| AR225211A1 (es) | 1982-02-26 |
| PT72486A (en) | 1981-03-01 |
| IT8119684A0 (it) | 1981-02-12 |
| NZ196174A (en) | 1983-05-10 |
| ATA69381A (de) | 1982-09-15 |
| CS217992B2 (en) | 1983-02-25 |
| AU535655B2 (en) | 1984-03-29 |
| FR2475536B2 (enExample) | 1985-05-24 |
| GR73151B (enExample) | 1984-02-10 |
| IE810264L (en) | 1981-08-13 |
| PL129543B3 (en) | 1984-05-31 |
| NL8100623A (nl) | 1981-09-16 |
| PL229649A3 (enExample) | 1982-05-24 |
| NL191439B (nl) | 1995-03-01 |
| DK154640B (da) | 1988-12-05 |
| AT370718B (de) | 1983-04-25 |
| BE887492A (fr) | 1981-08-12 |
| IE50863B1 (en) | 1986-08-06 |
| GB2068962B (en) | 1983-10-12 |
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