DE2744828B2 - - Google Patents
Info
- Publication number
- DE2744828B2 DE2744828B2 DE2744828A DE2744828A DE2744828B2 DE 2744828 B2 DE2744828 B2 DE 2744828B2 DE 2744828 A DE2744828 A DE 2744828A DE 2744828 A DE2744828 A DE 2744828A DE 2744828 B2 DE2744828 B2 DE 2744828B2
- Authority
- DE
- Germany
- Prior art keywords
- mol
- osmium tetroxide
- ether
- mixture
- methyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000012285 osmium tetroxide Substances 0.000 description 11
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 11
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- -1 acetylene compound Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- LWOLUVLUAVXOMH-UHFFFAOYSA-N 1-methoxybut-1-yne Chemical compound CCC#COC LWOLUVLUAVXOMH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YHYKAMJEIQTQCW-UHFFFAOYSA-N sulfanylideneosmium Chemical compound [Os]=S YHYKAMJEIQTQCW-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT28041/76A IT1077057B (it) | 1976-10-06 | 1976-10-06 | Processo per la preparazione di alfa-ossoesteri |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2744828A1 DE2744828A1 (de) | 1978-04-13 |
| DE2744828B2 true DE2744828B2 (enExample) | 1979-06-21 |
| DE2744828C3 DE2744828C3 (de) | 1980-02-14 |
Family
ID=11222803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2744828A Expired DE2744828C3 (de) | 1976-10-06 | 1977-10-05 | Verfahren zur Herstellung von a -Oxoestern |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4232169A (enExample) |
| JP (1) | JPS5346919A (enExample) |
| BE (1) | BE859443A (enExample) |
| CA (1) | CA1108178A (enExample) |
| CH (1) | CH625200A5 (enExample) |
| DE (1) | DE2744828C3 (enExample) |
| FR (1) | FR2367047A1 (enExample) |
| GB (1) | GB1553330A (enExample) |
| IT (1) | IT1077057B (enExample) |
| LU (1) | LU78257A1 (enExample) |
| NL (1) | NL7710999A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5851892A (ja) * | 1981-09-24 | 1983-03-26 | Eisai Co Ltd | 粗エラスタ−ゼの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048622A (en) * | 1960-12-16 | 1962-08-07 | Union Carbide Corp | Preparation of alpha-ketoesters |
| US3065259A (en) * | 1961-02-27 | 1962-11-20 | Merck & Co Inc | Method of making alpha-diketones |
-
1976
- 1976-10-06 IT IT28041/76A patent/IT1077057B/it active
-
1977
- 1977-09-09 CA CA286,454A patent/CA1108178A/en not_active Expired
- 1977-09-16 GB GB38822/77A patent/GB1553330A/en not_active Expired
- 1977-09-20 FR FR7728242A patent/FR2367047A1/fr active Granted
- 1977-10-03 JP JP11796577A patent/JPS5346919A/ja active Pending
- 1977-10-05 LU LU78257A patent/LU78257A1/xx unknown
- 1977-10-05 DE DE2744828A patent/DE2744828C3/de not_active Expired
- 1977-10-06 BE BE181507A patent/BE859443A/xx not_active IP Right Cessation
- 1977-10-06 CH CH1224977A patent/CH625200A5/it not_active IP Right Cessation
- 1977-10-06 NL NL7710999A patent/NL7710999A/xx not_active Application Discontinuation
-
1979
- 1979-04-24 US US06/033,014 patent/US4232169A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4232169A (en) | 1980-11-04 |
| IT1077057B (it) | 1985-04-27 |
| LU78257A1 (enExample) | 1978-01-26 |
| DE2744828C3 (de) | 1980-02-14 |
| CH625200A5 (en) | 1981-09-15 |
| GB1553330A (en) | 1979-09-26 |
| FR2367047A1 (fr) | 1978-05-05 |
| FR2367047B1 (enExample) | 1982-10-22 |
| BE859443A (fr) | 1978-04-06 |
| NL7710999A (nl) | 1978-04-10 |
| CA1108178A (en) | 1981-09-01 |
| JPS5346919A (en) | 1978-04-27 |
| DE2744828A1 (de) | 1978-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ANIC S.P.A., PALERMO, IT |
|
| 8339 | Ceased/non-payment of the annual fee |