HU182906B - Process for preparing 3,3-dimethyl-2-oxo-autyric acid and salts thereof - Google Patents
Process for preparing 3,3-dimethyl-2-oxo-autyric acid and salts thereof Download PDFInfo
- Publication number
- HU182906B HU182906B HU79MO1068A HUMO001068A HU182906B HU 182906 B HU182906 B HU 182906B HU 79MO1068 A HU79MO1068 A HU 79MO1068A HU MO001068 A HUMO001068 A HU MO001068A HU 182906 B HU182906 B HU 182906B
- Authority
- HU
- Hungary
- Prior art keywords
- acid
- dimethyl
- solution
- salt
- ruthenium
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 20
- 239000002253 acid Substances 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000003647 oxidation Effects 0.000 claims abstract description 15
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 15
- IAWVHZJZHDSEOC-UHFFFAOYSA-N 3,3-dimethyl-2-oxobutanoic acid Chemical compound CC(C)(C)C(=O)C(O)=O IAWVHZJZHDSEOC-UHFFFAOYSA-N 0.000 claims abstract description 13
- FWVNWTNCNWRCOU-UHFFFAOYSA-N 2-hydroxy-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)C(O)C(O)=O FWVNWTNCNWRCOU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000007800 oxidant agent Substances 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000012670 alkaline solution Substances 0.000 claims description 6
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 3
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical group O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000005708 Sodium hypochlorite Substances 0.000 abstract description 11
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract description 11
- FGEKTVAHFDQHBU-UHFFFAOYSA-N dioxoruthenium;hydrate Chemical compound O.O=[Ru]=O FGEKTVAHFDQHBU-UHFFFAOYSA-N 0.000 abstract description 7
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 239000000706 filtrate Substances 0.000 abstract description 2
- 150000003303 ruthenium Chemical class 0.000 abstract description 2
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000011949 solid catalyst Substances 0.000 abstract 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000001261 hydroxy acids Chemical class 0.000 description 15
- 238000001914 filtration Methods 0.000 description 7
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 7
- -1 alkali metal salts Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000004715 keto acids Chemical class 0.000 description 3
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 3
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000005583 Metribuzin Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- PWRYKCFNWWHKLP-UHFFFAOYSA-N ruthenium;hydrate Chemical compound O.[Ru] PWRYKCFNWWHKLP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96033078A | 1978-11-13 | 1978-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182906B true HU182906B (en) | 1984-03-28 |
Family
ID=25503053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79MO1068A HU182906B (en) | 1978-11-13 | 1979-11-13 | Process for preparing 3,3-dimethyl-2-oxo-autyric acid and salts thereof |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1097917B1 (en) * | 1999-11-03 | 2003-02-12 | Korea Research Institute Of Chemical Technology | Preparing method of alpha-ketocarboxylic acid derivatives |
| DE10236919A1 (de) * | 2002-08-12 | 2004-02-26 | Bayer Ag | Verfahren zur Herstellung von 3,3-Dimethyl-2-oxobuttersäure |
| JP4650714B2 (ja) * | 2003-09-01 | 2011-03-16 | ナガセケムテックス株式会社 | カルボニル化合物の製造方法 |
| CN113004141A (zh) * | 2019-12-19 | 2021-06-22 | 北京颖泰嘉和生物科技股份有限公司 | 3,3-二甲基-2-氧代丁酸和三嗪酮的制备方法 |
| CN112592265B (zh) * | 2020-12-21 | 2023-09-01 | 安达兰泽科技有限公司 | 3,3-二甲基-2-氧代丁酸及其钠盐的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1069955B (it) * | 1975-09-24 | 1985-03-25 | Air Prod & Chem | Procedimento per l'ossidazione catalitica selettiva di alcoli insaturi a formare composti carbonilici |
| US4052460A (en) * | 1976-01-20 | 1977-10-04 | Bayer Aktiengesellschaft | Production of 3,3-dimethyl-2-oxo-butyric acid salt |
-
1979
- 1979-09-20 CA CA336,011A patent/CA1113936A/en not_active Expired
- 1979-10-29 BR BR7906994A patent/BR7906994A/pt not_active IP Right Cessation
- 1979-11-05 DE DE7979104307T patent/DE2961465D1/de not_active Expired
- 1979-11-05 EP EP79104307A patent/EP0011207B1/de not_active Expired
- 1979-11-09 DD DD79216802A patent/DD146945A5/de unknown
- 1979-11-09 IL IL58678A patent/IL58678A/xx unknown
- 1979-11-12 DK DK477879A patent/DK153539C/da not_active IP Right Cessation
- 1979-11-13 CS CS797745A patent/CS209941B2/cs unknown
- 1979-11-13 HU HU79MO1068A patent/HU182906B/hu not_active IP Right Cessation
- 1979-11-13 JP JP14611679A patent/JPS5566536A/ja active Granted
- 1979-11-13 AR AR278864A patent/AR222669A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| BR7906994A (pt) | 1980-07-15 |
| EP0011207B1 (de) | 1981-11-25 |
| IL58678A (en) | 1982-11-30 |
| IL58678A0 (en) | 1980-02-29 |
| AR222669A1 (es) | 1981-06-15 |
| JPS6239149B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-08-21 |
| DK477879A (da) | 1980-05-14 |
| EP0011207A1 (de) | 1980-05-28 |
| DK153539B (da) | 1988-07-25 |
| JPS5566536A (en) | 1980-05-20 |
| DD146945A5 (de) | 1981-03-11 |
| CA1113936A (en) | 1981-12-08 |
| DE2961465D1 (en) | 1982-01-28 |
| CS209941B2 (en) | 1981-12-31 |
| DK153539C (da) | 1989-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |