CS209941B2 - Method of making the 3,3-dimethyl-2-oxobutyric acid - Google Patents
Method of making the 3,3-dimethyl-2-oxobutyric acid Download PDFInfo
- Publication number
- CS209941B2 CS209941B2 CS797745A CS774579A CS209941B2 CS 209941 B2 CS209941 B2 CS 209941B2 CS 797745 A CS797745 A CS 797745A CS 774579 A CS774579 A CS 774579A CS 209941 B2 CS209941 B2 CS 209941B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- solution
- acid
- dimethyl
- ruthenium
- added
- Prior art date
Links
- IAWVHZJZHDSEOC-UHFFFAOYSA-N 3,3-dimethyl-2-oxobutanoic acid Chemical compound CC(C)(C)C(=O)C(O)=O IAWVHZJZHDSEOC-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000243 solution Substances 0.000 claims abstract description 35
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 14
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 14
- 230000003647 oxidation Effects 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 9
- 239000012670 alkaline solution Substances 0.000 claims abstract description 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007800 oxidant agent Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 150000001261 hydroxy acids Chemical class 0.000 claims description 14
- 150000004715 keto acids Chemical class 0.000 claims description 13
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 11
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 11
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- -1 alkali metal salt Chemical class 0.000 claims description 9
- FGEKTVAHFDQHBU-UHFFFAOYSA-N dioxoruthenium;hydrate Chemical compound O.O=[Ru]=O FGEKTVAHFDQHBU-UHFFFAOYSA-N 0.000 claims description 4
- XWURZHGKODQZMK-UHFFFAOYSA-N O.[Ru]=O Chemical compound O.[Ru]=O XWURZHGKODQZMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims 2
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims 1
- 229940005991 chloric acid Drugs 0.000 claims 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000005583 Metribuzin Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000011031 large-scale manufacturing process Methods 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
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 239000012431 aqueous reaction media Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 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
- 239000007787 solid Substances 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- RHLLDTPGTFRJDJ-UHFFFAOYSA-N OCl.OCl Chemical compound OCl.OCl RHLLDTPGTFRJDJ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96033078A | 1978-11-13 | 1978-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209941B2 true CS209941B2 (en) | 1981-12-31 |
Family
ID=25503053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS797745A CS209941B2 (en) | 1978-11-13 | 1979-11-13 | Method of making the 3,3-dimethyl-2-oxobutyric acid |
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 |
| HU182906B (en) | 1984-03-28 |
| 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 |
| DK153539C (da) | 1989-01-02 |
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