DE2123930C3 - Verfahren zur Herstellung von Glycid - Google Patents
Verfahren zur Herstellung von GlycidInfo
- Publication number
- DE2123930C3 DE2123930C3 DE2123930A DE2123930A DE2123930C3 DE 2123930 C3 DE2123930 C3 DE 2123930C3 DE 2123930 A DE2123930 A DE 2123930A DE 2123930 A DE2123930 A DE 2123930A DE 2123930 C3 DE2123930 C3 DE 2123930C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- glycide
- solution
- allyl alcohol
- acid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 36
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 14
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 235000011187 glycerol Nutrition 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 2
- 230000002349 favourable effect Effects 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims 2
- 241000282461 Canis lupus Species 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000010517 secondary reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2123930A DE2123930C3 (de) | 1971-05-14 | 1971-05-14 | Verfahren zur Herstellung von Glycid |
| NL7202425A NL7202425A (Direct) | 1971-05-14 | 1972-02-24 | |
| DD161230A DD94986A5 (Direct) | 1971-05-14 | 1972-03-01 | |
| CH324172A CH557809A (de) | 1971-05-14 | 1972-03-06 | Verfahren zur herstellung von glycid. |
| FR7212369A FR2137484B1 (Direct) | 1971-05-14 | 1972-04-07 | |
| US00248047A US3816479A (en) | 1971-05-14 | 1972-04-27 | Process for the production of glycide |
| GB1961772A GB1377249A (en) | 1971-05-14 | 1972-04-27 | Production of glycidol |
| BE783329A BE783329A (fr) | 1971-05-14 | 1972-05-10 | Procede de fabrication de glycide |
| CA141,915A CA963017A (en) | 1971-05-14 | 1972-05-11 | Process for producing glycide |
| IT68496/72A IT966906B (it) | 1971-05-14 | 1972-05-12 | Procedimento per la produzione della glicide |
| JP47047095A JPS5216088B1 (Direct) | 1971-05-14 | 1972-05-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2123930A DE2123930C3 (de) | 1971-05-14 | 1971-05-14 | Verfahren zur Herstellung von Glycid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2123930A1 DE2123930A1 (de) | 1972-12-07 |
| DE2123930B2 DE2123930B2 (de) | 1973-03-01 |
| DE2123930C3 true DE2123930C3 (de) | 1973-10-04 |
Family
ID=5807848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2123930A Expired DE2123930C3 (de) | 1971-05-14 | 1971-05-14 | Verfahren zur Herstellung von Glycid |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3816479A (Direct) |
| JP (1) | JPS5216088B1 (Direct) |
| BE (1) | BE783329A (Direct) |
| CA (1) | CA963017A (Direct) |
| CH (1) | CH557809A (Direct) |
| DD (1) | DD94986A5 (Direct) |
| DE (1) | DE2123930C3 (Direct) |
| FR (1) | FR2137484B1 (Direct) |
| GB (1) | GB1377249A (Direct) |
| IT (1) | IT966906B (Direct) |
| NL (1) | NL7202425A (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01171712A (ja) * | 1987-12-26 | 1989-07-06 | Osaka Diamond Ind Co Ltd | 微細孔の加工法並びに加工用ドリル |
| WO2008028176A1 (en) * | 2006-09-01 | 2008-03-06 | The Curators Of The University Of Missouri | Soybean based epoxy resin and methods of making and use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754418A (fr) * | 1969-08-06 | 1971-01-18 | Degussa | Procede de preparation de glycerine |
-
1971
- 1971-05-14 DE DE2123930A patent/DE2123930C3/de not_active Expired
-
1972
- 1972-02-24 NL NL7202425A patent/NL7202425A/xx not_active Application Discontinuation
- 1972-03-01 DD DD161230A patent/DD94986A5/xx unknown
- 1972-03-06 CH CH324172A patent/CH557809A/xx not_active IP Right Cessation
- 1972-04-07 FR FR7212369A patent/FR2137484B1/fr not_active Expired
- 1972-04-27 US US00248047A patent/US3816479A/en not_active Expired - Lifetime
- 1972-04-27 GB GB1961772A patent/GB1377249A/en not_active Expired
- 1972-05-10 BE BE783329A patent/BE783329A/xx not_active IP Right Cessation
- 1972-05-11 CA CA141,915A patent/CA963017A/en not_active Expired
- 1972-05-12 JP JP47047095A patent/JPS5216088B1/ja active Pending
- 1972-05-12 IT IT68496/72A patent/IT966906B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT966906B (it) | 1974-02-20 |
| DD94986A5 (Direct) | 1973-01-12 |
| GB1377249A (en) | 1974-12-11 |
| BE783329A (fr) | 1972-09-01 |
| DE2123930A1 (de) | 1972-12-07 |
| US3816479A (en) | 1974-06-11 |
| NL7202425A (Direct) | 1972-11-16 |
| JPS5216088B1 (Direct) | 1977-05-06 |
| CH557809A (de) | 1975-01-15 |
| CA963017A (en) | 1975-02-18 |
| FR2137484B1 (Direct) | 1974-12-06 |
| DE2123930B2 (de) | 1973-03-01 |
| FR2137484A1 (Direct) | 1972-12-29 |
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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 | ||
| 8339 | Ceased/non-payment of the annual fee |