DE3113857A1 - Verfahren zur oxyacetylierung von phenylacetat - Google Patents
Verfahren zur oxyacetylierung von phenylacetatInfo
- Publication number
- DE3113857A1 DE3113857A1 DE19813113857 DE3113857A DE3113857A1 DE 3113857 A1 DE3113857 A1 DE 3113857A1 DE 19813113857 DE19813113857 DE 19813113857 DE 3113857 A DE3113857 A DE 3113857A DE 3113857 A1 DE3113857 A1 DE 3113857A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl acetate
- acetate
- metal
- acetoxyacetophenone
- amount
- 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.)
- Withdrawn
Links
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229940049953 phenylacetate Drugs 0.000 title claims abstract description 21
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- BGAXCPSNMHVHJC-UHFFFAOYSA-N phenacyl acetate Chemical compound CC(=O)OCC(=O)C1=CC=CC=C1 BGAXCPSNMHVHJC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 8
- 239000011707 mineral Substances 0.000 claims abstract description 8
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 22
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000021736 acetylation Effects 0.000 description 12
- 238000006640 acetylation reaction Methods 0.000 description 12
- 150000001242 acetic acid derivatives Chemical class 0.000 description 9
- 238000010586 diagram Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- FBSAITBEAPNWJG-UHFFFAOYSA-N (2-acetyloxyphenyl) acetate Chemical class CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 4
- WWEDAIJJBDFOOK-UHFFFAOYSA-N (2-acetylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(C)=O WWEDAIJJBDFOOK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OTHYPAMNTUGKDK-UHFFFAOYSA-N (3-acetylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(C)=O)=C1 OTHYPAMNTUGKDK-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000006137 acetoxylation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical class OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20899/81A IT1195775B (it) | 1980-04-07 | 1981-04-02 | Processo di ossiacetilazione,catalizzato con palladio,di fenil acetato a meta-acetossiacetofenone |
| GB8110492A GB2073198B (en) | 1980-04-07 | 1981-04-03 | Palladium catalyzed oxy-acetylation of phenyl acetate to meta-acetoxyacetophenone |
| FR8106843A FR2479810A1 (fr) | 1980-04-07 | 1981-04-06 | Procede d'oxyacetylation catalysee par le palladium de l'acetate de phenyle en acetoxyacetophenones |
| NL8101687A NL8101687A (nl) | 1980-04-07 | 1981-04-06 | Werkwijze voor het oxyacetyleren van fenylacetaat. |
| DE19813113857 DE3113857A1 (de) | 1980-04-07 | 1981-04-06 | Verfahren zur oxyacetylierung von phenylacetat |
| JP56050671A JPS5936971B2 (ja) | 1980-04-07 | 1981-04-06 | 酢酸フエニルのメタ−アセトキシアセトフエノンへのパラジウム触媒によるオキシ−アセチル化 |
| BE0/204404A BE888318A (fr) | 1980-04-07 | 1981-04-07 | Procede d'oxyacetylation catalysee par le palladium de l'acetate de phenyle en acetocyacetophenones, |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13770880A | 1980-04-07 | 1980-04-07 | |
| DE19813113857 DE3113857A1 (de) | 1980-04-07 | 1981-04-06 | Verfahren zur oxyacetylierung von phenylacetat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3113857A1 true DE3113857A1 (de) | 1982-10-21 |
Family
ID=43742354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813113857 Withdrawn DE3113857A1 (de) | 1980-04-07 | 1981-04-06 | Verfahren zur oxyacetylierung von phenylacetat |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5936971B2 (enExample) |
| BE (1) | BE888318A (enExample) |
| DE (1) | DE3113857A1 (enExample) |
| FR (1) | FR2479810A1 (enExample) |
| GB (1) | GB2073198B (enExample) |
| IT (1) | IT1195775B (enExample) |
| NL (1) | NL8101687A (enExample) |
-
1981
- 1981-04-02 IT IT20899/81A patent/IT1195775B/it active
- 1981-04-03 GB GB8110492A patent/GB2073198B/en not_active Expired
- 1981-04-06 FR FR8106843A patent/FR2479810A1/fr active Granted
- 1981-04-06 JP JP56050671A patent/JPS5936971B2/ja not_active Expired
- 1981-04-06 DE DE19813113857 patent/DE3113857A1/de not_active Withdrawn
- 1981-04-06 NL NL8101687A patent/NL8101687A/nl not_active Application Discontinuation
- 1981-04-07 BE BE0/204404A patent/BE888318A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE888318A (fr) | 1981-10-07 |
| IT1195775B (it) | 1988-10-27 |
| IT8120899A0 (it) | 1981-04-02 |
| JPS5936971B2 (ja) | 1984-09-06 |
| JPS56156233A (en) | 1981-12-02 |
| FR2479810A1 (fr) | 1981-10-09 |
| GB2073198A (en) | 1981-10-14 |
| GB2073198B (en) | 1984-10-31 |
| FR2479810B1 (enExample) | 1985-04-12 |
| NL8101687A (nl) | 1981-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: STREHL, P., DIPL.-ING. DIPL.-WIRTSCH.-ING. SCHUEBE |
|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |