DE2223299C3 - Verfahren zur Herstellung von alphasubstituierten Epoxid-Verbindungen - Google Patents
Verfahren zur Herstellung von alphasubstituierten Epoxid-VerbindungenInfo
- Publication number
- DE2223299C3 DE2223299C3 DE2223299A DE2223299A DE2223299C3 DE 2223299 C3 DE2223299 C3 DE 2223299C3 DE 2223299 A DE2223299 A DE 2223299A DE 2223299 A DE2223299 A DE 2223299A DE 2223299 C3 DE2223299 C3 DE 2223299C3
- Authority
- DE
- Germany
- Prior art keywords
- epoxy compounds
- substituted
- production
- alpha
- reaction
- 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 description 11
- 239000004593 Epoxy Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000005749 Copper compound Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001880 copper compounds Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- -1 halogen ion Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2449971 | 1971-05-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2223299A1 DE2223299A1 (de) | 1972-11-23 |
| DE2223299B2 DE2223299B2 (Direct) | 1974-02-14 |
| DE2223299C3 true DE2223299C3 (de) | 1974-10-03 |
Family
ID=11213758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2223299A Expired DE2223299C3 (de) | 1971-05-13 | 1972-05-12 | Verfahren zur Herstellung von alphasubstituierten Epoxid-Verbindungen |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT316574B (Direct) |
| AU (1) | AU466536B2 (Direct) |
| BE (1) | BE783339A (Direct) |
| CA (1) | CA996125A (Direct) |
| CH (1) | CH553774A (Direct) |
| DD (1) | DD97883A5 (Direct) |
| DE (1) | DE2223299C3 (Direct) |
| DK (1) | DK132274C (Direct) |
| FR (1) | FR2147922B1 (Direct) |
| GB (1) | GB1381012A (Direct) |
| LU (1) | LU65336A1 (Direct) |
| NL (1) | NL144270B (Direct) |
| NO (1) | NO137235C (Direct) |
| SE (1) | SE386176B (Direct) |
| ZA (1) | ZA722962B (Direct) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8516744D0 (en) * | 1985-07-02 | 1985-08-07 | British Petroleum Co Plc | Preparation of epoxides |
-
1972
- 1972-04-27 AU AU41628/72A patent/AU466536B2/en not_active Expired
- 1972-05-01 CA CA141,020A patent/CA996125A/en not_active Expired
- 1972-05-02 ZA ZA722962A patent/ZA722962B/xx unknown
- 1972-05-09 DK DK229772A patent/DK132274C/da active
- 1972-05-10 SE SE7206242A patent/SE386176B/xx unknown
- 1972-05-10 FR FR7216676A patent/FR2147922B1/fr not_active Expired
- 1972-05-10 NO NO1678/72A patent/NO137235C/no unknown
- 1972-05-11 GB GB2223572A patent/GB1381012A/en not_active Expired
- 1972-05-12 CH CH703472A patent/CH553774A/fr not_active IP Right Cessation
- 1972-05-12 DE DE2223299A patent/DE2223299C3/de not_active Expired
- 1972-05-12 LU LU65336D patent/LU65336A1/xx unknown
- 1972-05-12 AT AT416472A patent/AT316574B/de not_active IP Right Cessation
- 1972-05-12 DD DD162931A patent/DD97883A5/xx unknown
- 1972-05-12 BE BE783339A patent/BE783339A/xx unknown
- 1972-05-15 NL NL727206500A patent/NL144270B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2223299A1 (de) | 1972-11-23 |
| DK132274C (da) | 1976-05-10 |
| DE2223299B2 (Direct) | 1974-02-14 |
| CH553774A (fr) | 1974-09-13 |
| FR2147922A1 (Direct) | 1973-03-11 |
| SE386176B (sv) | 1976-08-02 |
| FR2147922B1 (Direct) | 1974-09-27 |
| GB1381012A (en) | 1975-01-22 |
| DD97883A5 (Direct) | 1973-05-20 |
| CA996125A (en) | 1976-08-31 |
| NL7206500A (Direct) | 1972-11-15 |
| NO137235B (no) | 1977-10-17 |
| BE783339A (fr) | 1972-09-01 |
| AU4162872A (en) | 1973-11-01 |
| ZA722962B (en) | 1973-02-28 |
| AU466536B2 (en) | 1975-10-30 |
| AT316574B (de) | 1974-07-25 |
| LU65336A1 (Direct) | 1972-08-23 |
| DK132274B (da) | 1975-11-17 |
| NO137235C (no) | 1978-01-25 |
| NL144270B (nl) | 1974-12-16 |
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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 | ||
| EGA | New person/name/address of the applicant | ||
| EHJ | Ceased/non-payment of the annual fee |