CS197291B2 - Process for preparing di-n-propylacetic acid - Google Patents

Process for preparing di-n-propylacetic acid Download PDF

Info

Publication number: CS197291B2
Authority: CS; Czechoslovakia
Prior art keywords: propyl; acid; sodium; acetic acid; nitrile
Prior art date: 1977-03-15

Application number

CS773336A

Other languages

Czech (cs)

English (en)

Inventor

Michel Chignac

Claude Granin

Charles Piregol

Original Assignee

Labaz

Priority date (The priority date 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 date listed.)

1977-03-15

Filing date

1977-05-20

Publication date

1980-04-30

1977-05-20 Application filed by Labaz filed Critical Labaz

1980-04-30 Publication of CS197291B2 publication Critical patent/CS197291B2/cs

Links

NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 title claims abstract description 85
238000004519 manufacturing process Methods 0.000 title description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 36
YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 claims abstract description 27
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 22
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 abstract description 18
OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 claims abstract description 14
235000010288 sodium nitrite Nutrition 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 8
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 4
229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 61
-1 alkali metal salts Chemical class 0.000 claims description 35
229910052708 sodium Inorganic materials 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
230000007062 hydrolysis Effects 0.000 claims description 13
238000006460 hydrolysis reaction Methods 0.000 claims description 13
150000002825 nitriles Chemical class 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 10
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
229910052791 calcium Inorganic materials 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
229910052749 magnesium Inorganic materials 0.000 claims 2
239000011777 magnesium Substances 0.000 claims 2
IFTIBNDWGNYRLS-UHFFFAOYSA-N n,n-dipropylacetamide Chemical compound CCCN(C(C)=O)CCC IFTIBNDWGNYRLS-UHFFFAOYSA-N 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 34
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 21
239000002253 acid Substances 0.000 abstract description 18
UZRGQIZTJOPZGE-UHFFFAOYSA-N 2-cyano-2-propylpentanoic acid Chemical compound CCCC(C(O)=O)(C#N)CCC UZRGQIZTJOPZGE-UHFFFAOYSA-N 0.000 abstract description 16
150000002148 esters Chemical class 0.000 abstract description 13
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 abstract description 11
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract description 9
238000010438 heat treatment Methods 0.000 abstract description 7
239000012429 reaction media Substances 0.000 abstract description 4
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 abstract description 3
230000003301 hydrolyzing effect Effects 0.000 abstract description 3
239000001117 sulphuric acid Substances 0.000 abstract 2
235000011149 sulphuric acid Nutrition 0.000 abstract 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
230000000911 decarboxylating effect Effects 0.000 abstract 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 71
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 33
239000000203 mixture Substances 0.000 description 20
239000012071 phase Substances 0.000 description 20
238000010992 reflux Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
238000005804 alkylation reaction Methods 0.000 description 12
238000007127 saponification reaction Methods 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
230000029936 alkylation Effects 0.000 description 10
238000004821 distillation Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000001340 alkali metals Chemical class 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 8
238000006114 decarboxylation reaction Methods 0.000 description 8
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 8
239000012535 impurity Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
150000003242 quaternary ammonium salts Chemical class 0.000 description 6
238000002955 isolation Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
GSZKHLKKYPBXKM-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(C(C)C)C(O)=O GSZKHLKKYPBXKM-UHFFFAOYSA-N 0.000 description 4
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
239000008213 purified water Substances 0.000 description 4
UGKAGYIWOQXPKP-UHFFFAOYSA-N 2-cyano-3-methyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(C#N)(C(C)C)C(O)=O UGKAGYIWOQXPKP-UHFFFAOYSA-N 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
238000010908 decantation Methods 0.000 description 3
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
229940005605 valeric acid Drugs 0.000 description 3
FSCFMUWAEFAUJX-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C#N)C(C)C FSCFMUWAEFAUJX-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 2
IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 2
208000022821 personality disease Diseases 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
NICLKHGIKDZZGV-UHFFFAOYSA-N 2-cyanopentanoic acid Chemical compound CCCC(C#N)C(O)=O NICLKHGIKDZZGV-UHFFFAOYSA-N 0.000 description 1
OKJQSUPURXTNME-UHFFFAOYSA-N 2-prop-2-enylpent-4-enoic acid Chemical compound C=CCC(C(=O)O)CC=C OKJQSUPURXTNME-UHFFFAOYSA-N 0.000 description 1
UMJPVWFIBILILQ-UHFFFAOYSA-N 3-methyl-2-propan-2-ylbutanamide Chemical compound CC(C)C(C(C)C)C(N)=O UMJPVWFIBILILQ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
KJIUNWBQLGEYHK-UHFFFAOYSA-N [Na].C(C)(=O)OCC.C(C)O Chemical compound [Na].C(C)(=O)OCC.C(C)O KJIUNWBQLGEYHK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000508 neurotrophic effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
238000011017 operating method Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000011112 process operation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
229940084026 sodium valproate Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CS773336A 1977-03-15 1977-05-20 Process for preparing di-n-propylacetic acid CS197291B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7707588A FR2383907A1 (fr)	1977-03-15	1977-03-15	Procede de preparation de derives de l'acide acetique et derives obtenus par ce procede

Publications (1)

Publication Number	Publication Date
CS197291B2 true CS197291B2 (en)	1980-04-30

Family

ID=9188073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS773336A CS197291B2 (en)	1977-03-15	1977-05-20	Process for preparing di-n-propylacetic acid

Country Status (34)

Country	Link
US (1)	US4127604A (el)
JP (1)	JPS53112806A (el)
AR (1)	AR213000A1 (el)
AT (1)	AT351011B (el)
AU (1)	AU508174B2 (el)
BE (1)	BE854488A (el)
CA (1)	CA1077057A (el)
CH (1)	CH621108A5 (el)
CS (1)	CS197291B2 (el)
DD (1)	DD129776A5 (el)
DE (1)	DE2721264C2 (el)
DK (1)	DK154417C (el)
ES (1)	ES467890A1 (el)
FI (1)	FI63927C (el)
FR (1)	FR2383907A1 (el)
GB (1)	GB1529786A (el)
GR (1)	GR60800B (el)
HU (1)	HU178811B (el)
IE (1)	IE45346B1 (el)
IL (1)	IL52023A (el)
IN (1)	IN156430B (el)
IT (1)	IT1080752B (el)
LU (1)	LU77303A1 (el)
MX (1)	MX4567E (el)
NL (1)	NL176852C (el)
NO (1)	NO147521C (el)
NZ (1)	NZ184328A (el)
OA (1)	OA05695A (el)
PL (1)	PL108173B1 (el)
PT (1)	PT66543B (el)
SE (1)	SE418175B (el)
SU (1)	SU703013A3 (el)
YU (1)	YU40480B (el)
ZA (1)	ZA773776B (el)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3103776A1 (de) *	1977-03-15	1982-01-07	Sanofi, 75008 Paris	Verfahren zur herstellung von di-n-propyl-essigsaeure
DE2844638C2 (de) *	1978-10-13	1987-02-26	Ruhrchemie Ag, 4200 Oberhausen	Verfahren zur Herstellung von Di-n- propylessigsäure
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1977
- 1977-03-15 FR FR7707588A patent/FR2383907A1/fr active Granted
- 1977-04-25 IN IN621/CAL/77A patent/IN156430B/en unknown
- 1977-05-04 DK DK196077A patent/DK154417C/da not_active IP Right Cessation
- 1977-05-04 NO NO771578A patent/NO147521C/no unknown
- 1977-05-05 IL IL52023A patent/IL52023A/xx unknown
- 1977-05-05 SE SE7705258A patent/SE418175B/xx not_active IP Right Cessation
- 1977-05-06 GR GR53388A patent/GR60800B/el unknown
- 1977-05-09 LU LU77303A patent/LU77303A1/xx unknown
- 1977-05-10 CA CA278,112A patent/CA1077057A/en not_active Expired
- 1977-05-10 HU HU77LA916A patent/HU178811B/hu unknown
- 1977-05-11 DE DE2721264A patent/DE2721264C2/de not_active Expired
- 1977-05-11 BE BE177459A patent/BE854488A/xx not_active IP Right Cessation
- 1977-05-12 CH CH596477A patent/CH621108A5/fr not_active IP Right Cessation
- 1977-05-13 PT PT66543A patent/PT66543B/pt unknown
- 1977-05-20 CS CS773336A patent/CS197291B2/cs unknown
- 1977-05-20 NL NLAANVRAGE7705564,A patent/NL176852C/xx not_active IP Right Cessation
- 1977-05-20 AR AR267719A patent/AR213000A1/es active
- 1977-05-25 US US05/800,344 patent/US4127604A/en not_active Expired - Lifetime
- 1977-05-26 DD DD7700199160A patent/DD129776A5/xx unknown
- 1977-05-31 PL PL1977198561A patent/PL108173B1/pl unknown
- 1977-06-02 JP JP6562877A patent/JPS53112806A/ja active Granted
- 1977-06-03 GB GB23784/77A patent/GB1529786A/en not_active Expired
- 1977-06-03 MX MX775779U patent/MX4567E/es unknown
- 1977-06-06 SU SU772489907A patent/SU703013A3/ru active
- 1977-06-08 NZ NZ184328A patent/NZ184328A/xx unknown
- 1977-06-15 YU YU1492/77A patent/YU40480B/xx unknown
- 1977-06-16 FI FI771899A patent/FI63927C/fi not_active IP Right Cessation
- 1977-06-21 AU AU26265/77A patent/AU508174B2/en not_active Expired
- 1977-06-21 IE IE1272/77A patent/IE45346B1/en not_active IP Right Cessation
- 1977-06-23 ZA ZA00773776A patent/ZA773776B/xx unknown
- 1977-06-27 OA OA56207A patent/OA05695A/xx unknown
- 1977-07-11 IT IT25584/77A patent/IT1080752B/it active
- 1977-07-19 AT AT521077A patent/AT351011B/de not_active IP Right Cessation
1978
- 1978-03-15 ES ES467890A patent/ES467890A1/es not_active Expired

Also Published As

Publication number	Publication date
SU703013A3 (ru)	1979-12-05
DD129776A5 (de)	1978-02-08
AT351011B (de)	1979-07-10
HU178811B (en)	1982-06-28
YU40480B (en)	1986-02-28
DK196077A (da)	1978-09-16
SE418175B (sv)	1981-05-11
NZ184328A (en)	1979-10-25
IL52023A (en)	1979-10-31
OA05695A (fr)	1981-05-31
IL52023A0 (en)	1977-07-31
NO147521B (no)	1983-01-17
ATA521077A (de)	1978-12-15
NL7705564A (nl)	1978-09-19
IE45346B1 (en)	1982-08-11
CH621108A5 (el)	1981-01-15
PL108173B1 (pl)	1980-03-31
LU77303A1 (el)	1977-08-24
AU2626577A (en)	1979-01-04
FI771899A (fi)	1978-09-16
PL198561A1 (pl)	1978-10-09
JPS53112806A (en)	1978-10-02
DK154417C (da)	1989-04-10
SE7705258L (sv)	1978-09-16
NO147521C (no)	1983-04-27
IN156430B (el)	1985-08-03
GB1529786A (en)	1978-10-25
FR2383907A1 (fr)	1978-10-13
FR2383907B1 (el)	1979-07-20
ZA773776B (en)	1978-05-30
FI63927B (fi)	1983-05-31
GR60800B (en)	1978-08-30
CA1077057A (en)	1980-05-06
MX4567E (es)	1982-06-17
NO771578L (no)	1978-09-18
AR213000A1 (es)	1978-11-30
AU508174B2 (en)	1980-03-13
NL176852B (nl)	1985-01-16
PT66543B (en)	1978-10-18
JPS5640137B2 (el)	1981-09-18
ES467890A1 (es)	1978-11-01
FI63927C (fi)	1983-09-12
IE45346L (en)	1978-09-15
YU149277A (en)	1982-06-30
IT1080752B (it)	1985-05-16
PT66543A (en)	1977-06-01
DE2721264C2 (de)	1984-07-19
DK154417B (da)	1988-11-14
NL176852C (nl)	1985-06-17
US4127604A (en)	1978-11-28
BE854488A (fr)	1977-11-14
DE2721264A1 (de)	1978-09-21

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