CA1113936A - Catalytic oxidation of 3,3-dimethyl 2-hydroxybutyric acid to 2-oxo acid - Google Patents
Catalytic oxidation of 3,3-dimethyl 2-hydroxybutyric acid to 2-oxo acidInfo
- Publication number
- CA1113936A CA1113936A CA336,011A CA336011A CA1113936A CA 1113936 A CA1113936 A CA 1113936A CA 336011 A CA336011 A CA 336011A CA 1113936 A CA1113936 A CA 1113936A
- Authority
- CA
- Canada
- Prior art keywords
- dimethyl
- acid
- ruthenium
- salt
- process according
- 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.)
- Expired
Links
- 230000003647 oxidation Effects 0.000 title claims description 13
- 238000007254 oxidation reaction Methods 0.000 title claims 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 title claims description 8
- 150000004716 alpha keto acids Chemical class 0.000 title description 3
- 230000003197 catalytic effect Effects 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 12
- FGEKTVAHFDQHBU-UHFFFAOYSA-N dioxoruthenium;hydrate Chemical compound O.O=[Ru]=O FGEKTVAHFDQHBU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 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 description 6
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 4
- NTRJJLQIKWDNTO-UHFFFAOYSA-M sodium;3,3-dimethyl-2-oxobutanoate Chemical compound [Na+].CC(C)(C)C(=O)C([O-])=O NTRJJLQIKWDNTO-UHFFFAOYSA-M 0.000 claims 3
- SBPMNPYWNBFQOA-UHFFFAOYSA-N 2-hydroxy-3,3-dimethylbutanoic acid;sodium Chemical compound [Na].CC(C)(C)C(O)C(O)=O SBPMNPYWNBFQOA-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract description 2
- 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 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- GPPPQOUTVCYLRS-UHFFFAOYSA-M sodium;2-hydroxy-3,3-dimethylbutanoate Chemical compound [Na+].CC(C)(C)C(O)C([O-])=O GPPPQOUTVCYLRS-UHFFFAOYSA-M 0.000 abstract 1
- 239000011949 solid catalyst Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 150000001261 hydroxy acids Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 10
- 229910019093 NaOCl Inorganic materials 0.000 description 9
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 9
- 150000004715 keto acids Chemical class 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 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
- 239000012429 reaction media Substances 0.000 description 2
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OFKAVNQBCRJBJE-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound CC(C)(C)C1=NNC(=S)N(N)C1=O OFKAVNQBCRJBJE-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229930194542 Keto Natural products 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- -1 alkaline earth metal salts Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 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
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96033078A | 1978-11-13 | 1978-11-13 | |
| US960,330 | 1978-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113936A true CA1113936A (en) | 1981-12-08 |
Family
ID=25503053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA336,011A Expired CA1113936A (en) | 1978-11-13 | 1979-09-20 | Catalytic oxidation of 3,3-dimethyl 2-hydroxybutyric acid to 2-oxo acid |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112592265A (zh) * | 2020-12-21 | 2021-04-02 | 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 |
Families Citing this family (4)
| 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 |
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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112592265A (zh) * | 2020-12-21 | 2021-04-02 | 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 |
| 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 |
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 |
| HU182906B (en) | 1984-03-28 |
| DK153539B (da) | 1988-07-25 |
| JPS5566536A (en) | 1980-05-20 |
| DD146945A5 (de) | 1981-03-11 |
| 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 |
|---|---|---|---|
| MKEX | Expiry |