DE2515074A1 - Verfahren zur oxydation von allylaceton zu 2,5-hexandion in einem loesungsmittelsystem aus wasser und tetrachlorkohlenstoff - Google Patents
Verfahren zur oxydation von allylaceton zu 2,5-hexandion in einem loesungsmittelsystem aus wasser und tetrachlorkohlenstoffInfo
- Publication number
- DE2515074A1 DE2515074A1 DE19752515074 DE2515074A DE2515074A1 DE 2515074 A1 DE2515074 A1 DE 2515074A1 DE 19752515074 DE19752515074 DE 19752515074 DE 2515074 A DE2515074 A DE 2515074A DE 2515074 A1 DE2515074 A1 DE 2515074A1
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- copper
- palladium
- solvent system
- ala
- 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
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 37
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 title claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 14
- 239000002904 solvent Substances 0.000 title claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 title 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 42
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 39
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 15
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 9
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 54
- 229910052763 palladium Inorganic materials 0.000 description 25
- XLYOFNOQVPJJNP-DYCDLGHISA-N deuterium hydrogen oxide Chemical compound [2H]O XLYOFNOQVPJJNP-DYCDLGHISA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000010410 layer Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000010949 copper Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000003822 preparative gas chromatography Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010405 reoxidation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- -1 acetonylacetone Chemical compound 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- VBRKIHDQHFBNJI-UHFFFAOYSA-N 1-hydroxyhexane-2,3-dione Chemical compound CCCC(=O)C(=O)CO VBRKIHDQHFBNJI-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- ZSDLLTJVENEIDW-UHFFFAOYSA-N 5-hydroxyhexan-2-one Chemical compound CC(O)CCC(C)=O ZSDLLTJVENEIDW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 235000008098 Oxalis acetosella Nutrition 0.000 description 1
- 240000007930 Oxalis acetosella Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 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
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- CLFYLNSQRWCJAY-UHFFFAOYSA-N hex-3-en-1-yne Chemical compound CCC=CC#C CLFYLNSQRWCJAY-UHFFFAOYSA-N 0.000 description 1
- OTSKZNVDZOOHRX-UHFFFAOYSA-N hex-3-ene-2,5-dione Chemical compound CC(=O)C=CC(C)=O OTSKZNVDZOOHRX-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000370 mercury sulfate Inorganic materials 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- PRDUHXPVDHDGKN-UHFFFAOYSA-N tetrachloromethane;hydrate Chemical compound O.ClC(Cl)(Cl)Cl PRDUHXPVDHDGKN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/458,474 US3972942A (en) | 1974-04-08 | 1974-04-08 | Oxidation of allylacetone to 2,5-hexanedione in a water-carbon tetrachloride solvent system |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2515074A1 true DE2515074A1 (de) | 1975-10-09 |
Family
ID=23820926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752515074 Pending DE2515074A1 (de) | 1974-04-08 | 1975-04-07 | Verfahren zur oxydation von allylaceton zu 2,5-hexandion in einem loesungsmittelsystem aus wasser und tetrachlorkohlenstoff |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3972942A (OSRAM) |
| JP (1) | JPS50135014A (OSRAM) |
| BE (1) | BE827643A (OSRAM) |
| CA (1) | CA1048543A (OSRAM) |
| DE (1) | DE2515074A1 (OSRAM) |
| FR (1) | FR2266685B1 (OSRAM) |
| GB (1) | GB1460554A (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203927A (en) * | 1978-04-11 | 1980-05-20 | Phillips Petroleum Company | Olefin oxidation process |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1129469B (de) * | 1957-09-28 | 1962-05-17 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden, Ketonen oder den Aldehyden entsprechenden Saeuren |
| US3303020A (en) * | 1963-10-21 | 1967-02-07 | Gulf Research Development Co | Process for the removal of a platinum group metal from an organic reaction product |
| NL136240C (OSRAM) * | 1968-12-04 | |||
| JPS4711411U (OSRAM) * | 1971-03-01 | 1972-10-11 |
-
1974
- 1974-04-08 US US05/458,474 patent/US3972942A/en not_active Expired - Lifetime
-
1975
- 1975-04-04 JP JP50041109A patent/JPS50135014A/ja active Pending
- 1975-04-07 GB GB1421675A patent/GB1460554A/en not_active Expired
- 1975-04-07 BE BE155160A patent/BE827643A/xx unknown
- 1975-04-07 FR FR7510752A patent/FR2266685B1/fr not_active Expired
- 1975-04-07 CA CA75223968A patent/CA1048543A/en not_active Expired
- 1975-04-07 DE DE19752515074 patent/DE2515074A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3972942A (en) | 1976-08-03 |
| GB1460554A (en) | 1977-01-06 |
| CA1048543A (en) | 1979-02-13 |
| FR2266685A1 (OSRAM) | 1975-10-31 |
| BE827643A (fr) | 1975-10-07 |
| FR2266685B1 (OSRAM) | 1979-05-11 |
| JPS50135014A (OSRAM) | 1975-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |