DE2032332A1 - Acylierung von Hexanondenvaten - Google Patents
Acylierung von HexanondenvatenInfo
- Publication number
- DE2032332A1 DE2032332A1 DE19702032332 DE2032332A DE2032332A1 DE 2032332 A1 DE2032332 A1 DE 2032332A1 DE 19702032332 DE19702032332 DE 19702032332 DE 2032332 A DE2032332 A DE 2032332A DE 2032332 A1 DE2032332 A1 DE 2032332A1
- Authority
- DE
- Germany
- Prior art keywords
- acylation
- acid
- dioximinocyclohexanone
- ketene
- anhydrides
- 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.)
- Pending
Links
- 238000005917 acylation reaction Methods 0.000 title claims description 20
- 230000010933 acylation Effects 0.000 title claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 title description 6
- 239000000523 sample Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims description 18
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- MLAWCOBYMMKWMA-UHFFFAOYSA-N 2,6-bis(hydroxyimino)cyclohexan-1-one Chemical compound ON=C1CCCC(=NO)C1=O MLAWCOBYMMKWMA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- -1 acetic anhydride Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 150000002561 ketenes Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
- MKLGDJMKBVJSSS-UHFFFAOYSA-N 4,6,7,8-tetrahydro-1,3-benzodioxin-5-one Chemical compound C1OCOC2=C1C(=O)CCC2 MKLGDJMKBVJSSS-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- JRPBGKUSZOBYTA-UHFFFAOYSA-N ethyl 5-cyano-2-hydroxyiminopentanoate Chemical compound CCOC(=O)C(=NO)CCCC#N JRPBGKUSZOBYTA-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83906169A | 1969-07-03 | 1969-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2032332A1 true DE2032332A1 (de) | 1971-01-21 |
Family
ID=25278762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702032332 Pending DE2032332A1 (de) | 1969-07-03 | 1970-06-30 | Acylierung von Hexanondenvaten |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE2032332A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2054140A5 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1256833A (cg-RX-API-DMAC10.html) |
| IT (1) | IT949227B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7009313A (cg-RX-API-DMAC10.html) |
-
1970
- 1970-06-17 GB GB1256833D patent/GB1256833A/en not_active Expired
- 1970-06-24 NL NL7009313A patent/NL7009313A/xx not_active Application Discontinuation
- 1970-06-30 DE DE19702032332 patent/DE2032332A1/de active Pending
- 1970-07-02 IT IT5184170A patent/IT949227B/it active
- 1970-07-03 FR FR7024799A patent/FR2054140A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1256833A (cg-RX-API-DMAC10.html) | 1971-12-15 |
| NL7009313A (cg-RX-API-DMAC10.html) | 1971-01-05 |
| IT949227B (it) | 1973-06-11 |
| FR2054140A5 (cg-RX-API-DMAC10.html) | 1971-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69716720T2 (de) | Verfahren zur cyclotrimerisierung von alkinen in wässrigen lösungen | |
| EP0760367A2 (de) | Verfahren zur Herstellung von 4-Acylamino-2,2,6,6-tetramethylpiperidinen | |
| DE69408578T2 (de) | Verfahren zur herstellung von 2-hydroxyarylaldehyden | |
| DE2414252C2 (cg-RX-API-DMAC10.html) | ||
| EP0002460A1 (de) | Verfahren zur Herstellung von 3,4-Methylendioxymandelsäure | |
| DE69309728T2 (de) | Verfahren zur Herstellung von Arylacrylsäuren und ihrer Ester | |
| DE2920267A1 (de) | Verfahren zur herstellung von substituierten 2-hydroxy-cyclopent-2-en-1- onen | |
| DE2852975C2 (de) | 5-Cyano-1-alkylpyrrol-2-essigsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2702088C2 (de) | Verfahren zur Autoxidation eines Cycloalkanons zu dem entsprechenden Cycloalkan-1,2-dion | |
| DE3327268A1 (de) | Verfahren fuer die herstellung des n-formyl-l-asparaginsaeureanhydrids | |
| DE3689764T2 (de) | Zwischenprodukte und Verfahren zu ihrer Herstellung. | |
| DE1951294C3 (de) | Verfahren zur Herstellung von 3-Hydroxy-2-methyl-y-pyron (Maltol) | |
| CH646679A5 (de) | Verfahren zur herstellung von 1,5-dimethyl-bicyclo(3,2,1)octanol-8. | |
| EP0061669B1 (de) | Verbessertes Verfahren zur Herstellung von Cyclohexan-1,3-dionen sowie einige neue bicyclische Cyclohexan-1,3-dione | |
| WO2004069784A1 (de) | Verfahren zur katalytischen oxidation von methan zu methanol über methanolester | |
| DD200795A5 (de) | Verfahren zur herstellung von diphenylaether-derivaten | |
| DE3813452A1 (de) | Verfahren zur herstellung von trifluormethylbenzoesaeure aus hexafluorxylol | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| DE2521610C2 (de) | Verfahren zur Herstellung von Arylessigsäuren und deren Estern | |
| DE2501742A1 (de) | O-(3-hydroxy-1-isochinolinyl)-benzoesaeure, n-phenylacetyl-phthalimid, verfahren zu dessen herstellung sowie ein verfahren zur herstellung von 7-oxo-7h-dibenzo- eckige klammer auf d e, h eckige klammer zu -chinolin-2-ol unter verwendung desselben | |
| AT249682B (de) | Verfahren zur Herstellung von 3,5-Diamino-6-chlor-pyrazincarbonsäureestern | |
| DE2459233C2 (de) | Verfahren zur Herstellung von Hydrochinon | |
| EP0741123A1 (de) | Verfahren zur Herstellung von Salzen substituierter oder unsubstituierter Phthalsäure-Derivate | |
| DE2166727A1 (de) | Cyclopropanderivate | |
| DE2256253C3 (de) | Verfahren zur Herstellung von Phthalimide- oder Cyclohexen-1,2-dicarboximidothionophosphaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |