JPS6131093B2 - - Google Patents
Info
- Publication number
- JPS6131093B2 JPS6131093B2 JP52004476A JP447677A JPS6131093B2 JP S6131093 B2 JPS6131093 B2 JP S6131093B2 JP 52004476 A JP52004476 A JP 52004476A JP 447677 A JP447677 A JP 447677A JP S6131093 B2 JPS6131093 B2 JP S6131093B2
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- reaction
- permanganate
- dimethyl
- reaction mixture
- 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
- UDWZXMQIEHAAQT-UHFFFAOYSA-N 1,1-dichloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Cl)Cl UDWZXMQIEHAAQT-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 description 7
- 239000003513 alkali Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000012286 potassium permanganate Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 239000011449 brick Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910000975 Carbon steel Inorganic materials 0.000 description 2
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000010962 carbon steel Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 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 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RLGGOWVSISCWMB-UHFFFAOYSA-N 1,1,1-trichloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Cl)(Cl)Cl RLGGOWVSISCWMB-UHFFFAOYSA-N 0.000 description 1
- ULSAJQMHTGKPIY-UHFFFAOYSA-N 1-chloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CCl ULSAJQMHTGKPIY-UHFFFAOYSA-N 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 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 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/650,651 US4052460A (en) | 1976-01-20 | 1976-01-20 | Production of 3,3-dimethyl-2-oxo-butyric acid salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5289610A JPS5289610A (en) | 1977-07-27 |
| JPS6131093B2 true JPS6131093B2 (US07601507-20091013-C00023.png) | 1986-07-17 |
Family
ID=24609738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP447677A Granted JPS5289610A (en) | 1976-01-20 | 1977-01-20 | Method of producing 3*33dimethll22oxoobutyrate |
Country Status (14)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4564704A (en) * | 1976-01-20 | 1986-01-14 | Bayer Aktiengesellschaft | Production of 3,3-dimethyl-2-oxo-butyric acid salt |
| CA1113936A (en) * | 1978-11-13 | 1981-12-08 | Dennis E. Jackman | Catalytic oxidation of 3,3-dimethyl 2-hydroxybutyric acid to 2-oxo acid |
| US4614822A (en) * | 1978-11-13 | 1986-09-30 | Mobay Chemical Corporation | Catalytic oxidation of 3,3-dimethyl-2-hydroxybutyric acid to 2-oxo acid and preparation of 4-amino-6-tert.-butyl-3-thio-1,2,4-triazine-5(4-H)-one |
| FR2832226B1 (fr) | 2001-11-13 | 2004-10-22 | Nexans | Module de distribution et de connexion de fibres optiques destine a un repartiteur optique |
| JP4111756B2 (ja) * | 2002-06-20 | 2008-07-02 | セントラル硝子株式会社 | ３，３，３−トリフルオロ−２−ヒドロキシプロピオン酸およびその誘導体の製造方法 |
| DE10236919A1 (de) * | 2002-08-12 | 2004-02-26 | Bayer Ag | Verfahren zur Herstellung von 3,3-Dimethyl-2-oxobuttersäure |
| CN101898954A (zh) * | 2009-05-27 | 2010-12-01 | 北京紫光英力化工技术有限公司 | 二氯嚬哪酮碱解新工艺 |
| CN105884606A (zh) * | 2016-04-26 | 2016-08-24 | 湖州恒远生物化学技术有限公司 | 一种三甲基丙酮酸的合成工艺 |
| CN109293591B (zh) * | 2018-10-26 | 2020-11-10 | 江苏七洲绿色化工股份有限公司 | 一种三嗪酮的制备方法 |
| CN109912395A (zh) * | 2019-04-04 | 2019-06-21 | 杭州众立化工科技有限公司 | 一种微分环流连续生产二氯频呐酮的装置与工艺 |
| 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 |
-
1976
- 1976-01-20 US US05/650,651 patent/US4052460A/en not_active Expired - Lifetime
- 1976-10-26 DE DE2648300A patent/DE2648300C3/de not_active Expired
-
1977
- 1977-01-17 IL IL51272A patent/IL51272A/xx unknown
- 1977-01-17 GB GB1688/77A patent/GB1527472A/en not_active Expired
- 1977-01-17 BR BR7700288A patent/BR7700288A/pt unknown
- 1977-01-17 CH CH55277A patent/CH626039A5/de not_active IP Right Cessation
- 1977-01-17 NL NLAANVRAGE7700446,A patent/NL189291C/xx not_active IP Right Cessation
- 1977-01-17 GB GB11416/78A patent/GB1527474A/en not_active Expired
- 1977-01-17 GB GB11415/78A patent/GB1527473A/en not_active Expired
- 1977-01-18 AT AT25277A patent/AT346824B/de not_active IP Right Cessation
- 1977-01-18 IT IT19411/77A patent/IT1075057B/it active
- 1977-01-19 BE BE174195A patent/BE850523A/xx not_active IP Right Cessation
- 1977-01-19 DK DK20077A patent/DK20077A/da not_active Application Discontinuation
- 1977-01-19 ES ES455148A patent/ES455148A1/es not_active Expired
- 1977-01-20 JP JP447677A patent/JPS5289610A/ja active Granted
- 1977-01-20 FR FR7701570A patent/FR2338922A1/fr active Granted
-
1979
- 1979-11-07 IL IL58657A patent/IL58657A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT346824B (de) | 1978-11-27 |
| US4052460A (en) | 1977-10-04 |
| GB1527473A (en) | 1978-10-04 |
| BR7700288A (pt) | 1977-09-20 |
| ATA25277A (de) | 1978-04-15 |
| NL7700446A (nl) | 1977-07-22 |
| CH626039A5 (US07601507-20091013-C00023.png) | 1981-10-30 |
| IL58657A0 (en) | 1980-02-29 |
| NL189291C (nl) | 1993-03-01 |
| ES455148A1 (es) | 1978-01-01 |
| BE850523A (fr) | 1977-07-19 |
| FR2338922A1 (fr) | 1977-08-19 |
| FR2338922B1 (US07601507-20091013-C00023.png) | 1983-10-07 |
| JPS5289610A (en) | 1977-07-27 |
| IT1075057B (it) | 1985-04-22 |
| GB1527474A (en) | 1978-10-04 |
| IL51272A0 (en) | 1977-03-31 |
| DE2648300C3 (de) | 1980-07-03 |
| GB1527472A (en) | 1978-10-04 |
| NL189291B (nl) | 1992-10-01 |
| IL51272A (en) | 1980-11-30 |
| DE2648300B2 (de) | 1979-10-18 |
| DE2648300A1 (de) | 1977-07-21 |
| DK20077A (da) | 1977-07-21 |
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