DE2129938B2 - Verfahren zur herstellung von epoxydverbindungen - Google Patents
Verfahren zur herstellung von epoxydverbindungenInfo
- Publication number
- DE2129938B2 DE2129938B2 DE19712129938 DE2129938A DE2129938B2 DE 2129938 B2 DE2129938 B2 DE 2129938B2 DE 19712129938 DE19712129938 DE 19712129938 DE 2129938 A DE2129938 A DE 2129938A DE 2129938 B2 DE2129938 B2 DE 2129938B2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- copper
- epoxy compounds
- compounds
- carbonyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 title description 10
- 239000004593 Epoxy Substances 0.000 title description 5
- 239000005749 Copper compound Substances 0.000 claims description 9
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 9
- 150000001880 copper compounds Chemical class 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- -1 copper halide Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000005840 aryl radicals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- HIDCXQDJRDKVAJ-UHFFFAOYSA-N CS(=O)C.[Cu] Chemical compound CS(=O)C.[Cu] HIDCXQDJRDKVAJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2611070 | 1970-06-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2129938A1 DE2129938A1 (de) | 1971-12-23 |
| DE2129938B2 true DE2129938B2 (de) | 1973-09-06 |
| DE2129938C3 DE2129938C3 (show.php) | 1974-04-11 |
Family
ID=11218649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712129938 Granted DE2129938B2 (de) | 1970-06-17 | 1971-06-16 | Verfahren zur herstellung von epoxydverbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3773798A (show.php) |
| BE (1) | BE768326A (show.php) |
| CA (1) | CA940937A (show.php) |
| DE (1) | DE2129938B2 (show.php) |
| FR (1) | FR2096053A5 (show.php) |
| GB (1) | GB1331856A (show.php) |
| LU (1) | LU63334A1 (show.php) |
| NL (1) | NL7108100A (show.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011954A (en) * | 1989-08-30 | 1991-04-30 | E. I. Du Pont De Nemours And Company | Epoxides and their preparation |
| US5214167A (en) * | 1989-08-30 | 1993-05-25 | E. I. Du Pont De Nemours And Company | Epoxides and their preparation |
-
1971
- 1971-05-27 GB GB1769571A patent/GB1331856A/en not_active Expired
- 1971-06-08 FR FR7120699A patent/FR2096053A5/fr not_active Expired
- 1971-06-10 BE BE768326A patent/BE768326A/xx unknown
- 1971-06-11 CA CA115,489A patent/CA940937A/en not_active Expired
- 1971-06-14 NL NL7108100A patent/NL7108100A/xx unknown
- 1971-06-15 LU LU63334D patent/LU63334A1/xx unknown
- 1971-06-16 DE DE19712129938 patent/DE2129938B2/de active Granted
- 1971-06-17 US US00154220A patent/US3773798A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2129938A1 (de) | 1971-12-23 |
| NL7108100A (show.php) | 1971-12-21 |
| GB1331856A (en) | 1973-09-26 |
| LU63334A1 (show.php) | 1971-09-13 |
| CA940937A (en) | 1974-01-29 |
| DE2129938C3 (show.php) | 1974-04-11 |
| FR2096053A5 (show.php) | 1972-02-11 |
| BE768326A (fr) | 1971-11-03 |
| US3773798A (en) | 1973-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |