CA1048543A - Oxidation of allylacetone to 2,5-hexanedione in a water-carbon tetrachloride solvent system - Google Patents
Oxidation of allylacetone to 2,5-hexanedione in a water-carbon tetrachloride solvent systemInfo
- Publication number
- CA1048543A CA1048543A CA75223968A CA223968A CA1048543A CA 1048543 A CA1048543 A CA 1048543A CA 75223968 A CA75223968 A CA 75223968A CA 223968 A CA223968 A CA 223968A CA 1048543 A CA1048543 A CA 1048543A
- Authority
- CA
- Canada
- Prior art keywords
- chloride
- palladium
- allylacetone
- hexanedione
- solvent system
- 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.)
- Expired
Links
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 title claims abstract description 43
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000002904 solvent Substances 0.000 title claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 title abstract description 15
- 230000003647 oxidation Effects 0.000 title abstract description 13
- PRDUHXPVDHDGKN-UHFFFAOYSA-N tetrachloromethane;hydrate Chemical compound O.ClC(Cl)(Cl)Cl PRDUHXPVDHDGKN-UHFFFAOYSA-N 0.000 title description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 30
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 39
- 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
- 230000001590 oxidative effect Effects 0.000 claims description 11
- 229960003280 cupric chloride Drugs 0.000 claims description 10
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 8
- 229940045803 cuprous chloride Drugs 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 56
- 229910052763 palladium Inorganic materials 0.000 abstract description 27
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 21
- 229950005499 carbon tetrachloride Drugs 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000010949 copper Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000007800 oxidant agent Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010405 reoxidation reaction Methods 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910021120 PdC12 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 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
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OTSKZNVDZOOHRX-ONEGZZNKSA-N (e)-hex-3-ene-2,5-dione Chemical compound CC(=O)\C=C\C(C)=O OTSKZNVDZOOHRX-ONEGZZNKSA-N 0.000 description 1
- 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
- PNKIAICRRFHSBQ-UHFFFAOYSA-N 2-(bromomethyl)-3-methyloxirane Chemical compound CC1OC1CBr PNKIAICRRFHSBQ-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010960 commercial process Methods 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
- XLYOFNOQVPJJNP-DYCDLGHISA-N deuterium hydrogen oxide Chemical compound [2H]O XLYOFNOQVPJJNP-DYCDLGHISA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- -1 i.e. Chemical compound 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
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 238000006479 redox reaction 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
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 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 |
|---|---|
| CA1048543A true CA1048543A (en) | 1979-02-13 |
Family
ID=23820926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75223968A Expired CA1048543A (en) | 1974-04-08 | 1975-04-07 | Oxidation of allylacetone to 2,5-hexanedione in a water-carbon tetrachloride solvent system |
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 |
| FR2266685A1 (OSRAM) | 1975-10-31 |
| BE827643A (fr) | 1975-10-07 |
| FR2266685B1 (OSRAM) | 1979-05-11 |
| DE2515074A1 (de) | 1975-10-09 |
| JPS50135014A (OSRAM) | 1975-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2618389B2 (ja) | 水性トリフルオロメタンスルホン酸中でセリウムイオンを使用する有機化合物の酸化 | |
| US2773101A (en) | Catalytic reactions with osmium oxide catalysts | |
| CA1048543A (en) | Oxidation of allylacetone to 2,5-hexanedione in a water-carbon tetrachloride solvent system | |
| US4271320A (en) | Process for producing a higher carbonyl compound | |
| US3947521A (en) | Oxidation of allylacetone to 2,5-hexanedione | |
| EP1950191B1 (en) | Process for producing 3,3,3-trifluoropropionic acid | |
| JP2588695B2 (ja) | カルボニル基含有化合物の製造方法 | |
| US3376351A (en) | Process for producing methoxyphenol or ethoxyphenol | |
| EP0438143B1 (en) | Process for the preparation of dodecanedioic acid | |
| CA1048542A (en) | Oxidation of allylacetone to 2,5-hexanedione in a high-boiling hydrocarbon solvent system | |
| US2837575A (en) | Preparation of ketals | |
| US5382694A (en) | Process for the continuous production of aromatic aldehydes | |
| EP0076533B1 (en) | A process for the preparation of tertiary-butyl hydroperoxide | |
| CA1059531A (en) | Selective oxidation of chrysanthemyl alcohol | |
| US4334099A (en) | Preparation of hexafluoroacetone from hexafluorothioacetone dimer | |
| EP0039157B1 (en) | Chlorination of 4-methoxybenzoyl chloride | |
| US4263458A (en) | Preparation of aromatic fluoro-compounds | |
| JPH06107650A (ja) | ヘキサフルオロプロペンオキシドの製造方法 | |
| CA1064964A (en) | Process for dehalogenation and/or prevention of halogenation | |
| EP1468983B1 (en) | Process for producing 2,5-bis(trifluoromethyl)nitrobenzene | |
| JPS6116253B2 (OSRAM) | ||
| JP3296165B2 (ja) | ハイドロパーオキサイドの分解方法 | |
| JP3225605B2 (ja) | フェノール及びメチルエチルケトンの製造方法 | |
| JP3435655B2 (ja) | α，β−不飽和カルボン酸の製造方法 | |
| JP2000517326A (ja) | アルキンジオール又はアルキンジオールとアルキンモノオールとの混合物を製造する方法 |