CA1052824A - Process for the preparation of dioldions - Google Patents
Process for the preparation of dioldionsInfo
- Publication number
- CA1052824A CA1052824A CA229,052A CA229052A CA1052824A CA 1052824 A CA1052824 A CA 1052824A CA 229052 A CA229052 A CA 229052A CA 1052824 A CA1052824 A CA 1052824A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- preparation
- process according
- compounds
- alkaline
- 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
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims abstract description 8
- 239000012285 osmium tetroxide Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- -1 alkaline-earth metal chlorate Chemical class 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 4
- 150000002240 furans Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229960004926 chlorobutanol Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- KXUSQYGLNZFMTE-UHFFFAOYSA-N hex-2-yne-1,1-diol Chemical compound CCCC#CC(O)O KXUSQYGLNZFMTE-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-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 |
|---|---|---|---|
| IT23897/74A IT1014989B (it) | 1974-06-12 | 1974-06-12 | Processo per la preparazione di dioldioni |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052824A true CA1052824A (en) | 1979-04-17 |
Family
ID=11210722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,052A Expired CA1052824A (en) | 1974-06-12 | 1975-06-11 | Process for the preparation of dioldions |
Country Status (19)
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437648A (en) * | 1943-09-15 | 1948-03-09 | Research Corp | Catalytic oxidation of unsaturated organic compounds |
| US2718529A (en) * | 1952-06-28 | 1955-09-20 | Shell Dev | Hydroxylation of unsaturated aldehydes |
| US2773101A (en) * | 1952-07-25 | 1956-12-04 | Shell Dev | Catalytic reactions with osmium oxide catalysts |
| US2813130A (en) * | 1954-09-13 | 1957-11-12 | Shell Dev | Recovery of osmium compounds by adsorption on alumina |
| US3317592A (en) * | 1962-02-09 | 1967-05-02 | Celanese Corp | Catalyzed oxidation reactions |
| US3337635A (en) * | 1964-11-09 | 1967-08-22 | Marathon Oil Co | Method of producing ketols from hydrocarbons |
| US3488394A (en) * | 1966-05-11 | 1970-01-06 | Fmc Corp | Oxidation of olefinic compounds to glycols |
-
1974
- 1974-06-12 IT IT23897/74A patent/IT1014989B/it active
-
1975
- 1975-05-28 ZA ZA00753471A patent/ZA753471B/xx unknown
- 1975-06-03 YU YU1425/75A patent/YU37304B/xx unknown
- 1975-06-05 FR FR7517603A patent/FR2274592A1/fr active Granted
- 1975-06-09 CS CS754026A patent/CS196274B2/cs unknown
- 1975-06-10 LU LU72704A patent/LU72704A1/xx unknown
- 1975-06-11 IL IL47460A patent/IL47460A/xx unknown
- 1975-06-11 DK DK264575A patent/DK264575A/da not_active Application Discontinuation
- 1975-06-11 CA CA229,052A patent/CA1052824A/en not_active Expired
- 1975-06-11 HU HU75SA00002802A patent/HU171172B/hu unknown
- 1975-06-11 CH CH755875A patent/CH605522A5/xx not_active IP Right Cessation
- 1975-06-11 NO NO752081A patent/NO141513C/no unknown
- 1975-06-11 BE BE157225A patent/BE830110A/xx not_active IP Right Cessation
- 1975-06-12 US US05/586,357 patent/US4001333A/en not_active Expired - Lifetime
- 1975-06-12 JP JP50070242A patent/JPS5839136B2/ja not_active Expired
- 1975-06-12 SE SE7506764A patent/SE422200B/xx unknown
- 1975-06-12 GB GB2527975A patent/GB1473457A/en not_active Expired
- 1975-06-12 DD DD186601A patent/DD118068A5/xx unknown
- 1975-06-12 NL NL7507041A patent/NL7507041A/xx not_active Application Discontinuation
Also Published As
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