DE2257083B2 - Verfahren zur Herstellung von Glykolestem - Google Patents
Verfahren zur Herstellung von GlykolestemInfo
- Publication number
- DE2257083B2 DE2257083B2 DE2257083A DE2257083A DE2257083B2 DE 2257083 B2 DE2257083 B2 DE 2257083B2 DE 2257083 A DE2257083 A DE 2257083A DE 2257083 A DE2257083 A DE 2257083A DE 2257083 B2 DE2257083 B2 DE 2257083B2
- Authority
- DE
- Germany
- Prior art keywords
- production
- rcoo
- glycol esters
- oxidation
- palladium
- 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 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000002334 glycols Chemical class 0.000 title claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- -1 olefin compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004331 potassium propionate Substances 0.000 description 1
- 235000010332 potassium propionate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3173571 | 1971-11-26 | ||
| IT31735/71A IT941807B (it) | 1971-11-26 | 1971-11-26 | Procedimento per l ossidazione di composti vinilici |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2257083A1 DE2257083A1 (de) | 1973-05-30 |
| DE2257083B2 true DE2257083B2 (de) | 1975-08-14 |
| DE2257083C3 DE2257083C3 (enrdf_load_stackoverflow) | 1976-04-01 |
Family
ID=11234292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257083A Granted DE2257083B2 (de) | 1971-11-26 | 1972-11-21 | Verfahren zur Herstellung von Glykolestem |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE791713A (enrdf_load_stackoverflow) |
| DE (1) | DE2257083B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2160938B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1407480A (enrdf_load_stackoverflow) |
| IE (1) | IE38001B1 (enrdf_load_stackoverflow) |
| IT (1) | IT941807B (enrdf_load_stackoverflow) |
| LU (1) | LU66539A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7215699A (enrdf_load_stackoverflow) |
| NO (1) | NO135821C (enrdf_load_stackoverflow) |
-
0
- BE BE791713D patent/BE791713A/xx unknown
-
1971
- 1971-11-26 IT IT31735/71A patent/IT941807B/it active
-
1972
- 1972-11-15 IE IE1575/72A patent/IE38001B1/xx unknown
- 1972-11-17 GB GB5337372A patent/GB1407480A/en not_active Expired
- 1972-11-20 NL NL7215699A patent/NL7215699A/xx not_active Application Discontinuation
- 1972-11-21 DE DE2257083A patent/DE2257083B2/de active Granted
- 1972-11-22 FR FR7241407A patent/FR2160938B1/fr not_active Expired
- 1972-11-24 NO NO4312/72A patent/NO135821C/no unknown
- 1972-11-24 LU LU66539A patent/LU66539A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2160938A1 (enrdf_load_stackoverflow) | 1973-07-06 |
| LU66539A1 (enrdf_load_stackoverflow) | 1973-02-01 |
| NO135821C (enrdf_load_stackoverflow) | 1977-06-08 |
| NO135821B (enrdf_load_stackoverflow) | 1977-02-28 |
| BE791713A (fr) | 1973-03-16 |
| NL7215699A (enrdf_load_stackoverflow) | 1973-05-29 |
| IT941807B (it) | 1973-03-10 |
| DE2257083A1 (de) | 1973-05-30 |
| IE38001B1 (en) | 1977-12-07 |
| GB1407480A (en) | 1975-09-24 |
| IE38001L (en) | 1973-05-26 |
| FR2160938B1 (enrdf_load_stackoverflow) | 1975-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1543427C3 (enrdf_load_stackoverflow) | ||
| DE2462444B2 (de) | Verfahren zur Herstellung von Monocarbonsäureester« | |
| DE1468932B2 (de) | Verfahren zur kontinuierlichen herstellung von niedermolekularen aliphatischen acrylsaeureestern | |
| DE1000375C2 (de) | Verfahren zur Herstellung von kristallisierbaren Pentaenaldehydkomplexverbindungen mit Vitamin-A-Aldehydaufbau | |
| DE2257083C3 (enrdf_load_stackoverflow) | ||
| DE1223365B (de) | Verfahren zur Herstellung von sekundaeren Alkoholen und deren Estern | |
| DD215529A5 (de) | Verfahren zur herstellung von cyclohexandionderivaten | |
| DE2257083B2 (de) | Verfahren zur Herstellung von Glykolestem | |
| DE709129C (de) | Verfahren zur Herstellung von Anlagerungsverbindungen "Dien-Synthese" | |
| DE602005005354T2 (de) | Verfahren zur herstellung von 1,4-dialkyl-2,3-diol-1,4-butandion | |
| DE2844949A1 (de) | Verfahren zur herstellung von 4-acyloxy-2-methylcrotonaldehyden | |
| CH627727A5 (en) | Process for the preparation of phenylalkylcarboxylic acids | |
| DE3616363C2 (enrdf_load_stackoverflow) | ||
| EP0047831A1 (de) | Verfahren zur Herstellung von überwiegend linearen aliphatischen Carbonsäureestern | |
| DE1643644C3 (de) | Derivate des 3,7-Dimethyl-2,7octadien-1 -als und Verfahren zu deren Herstellung | |
| DE892893C (de) | Verfahren zur Herstellung von Carbonsaeureestern | |
| DE2163752B2 (de) | Verfahren zur Herstellung von fluorierten Aldehyden und Alkoholen | |
| DE2652202C2 (de) | Verfahren zur Herstellung von 3,7-Dimethyl-octan-7-ol-1-al oder dessen Ester | |
| DE1443807A1 (de) | 2,2-Dialkyl-Omega-Formylderivate sowie Verfahren zur Herstellung derselben | |
| DE1001258C2 (de) | Verfahren zur Herstellung von konjugierten Polyenen der Vitamin-A-Reihe | |
| DE3518075C2 (de) | Glyoxalderivate und Verfahren zu ihrer Herstellung | |
| AT264725B (de) | Verfahren zur Herstellung von Polyenverbindungen | |
| DE729187C (de) | Verfahren zur Herstellung von Methylencarbonsaeurealkylestern | |
| DE1076681B (de) | Verfahren zur Herstellung von Vitamin A-aldehyd | |
| DE875193C (de) | Verfahren zur Herstellung organischer sauerstoffhaltiger Verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |