DE2109453C3 - Verfahren zur Herstellung von vicinalen Glykolen - Google Patents
Verfahren zur Herstellung von vicinalen GlykolenInfo
- Publication number
- DE2109453C3 DE2109453C3 DE2109453A DE2109453A DE2109453C3 DE 2109453 C3 DE2109453 C3 DE 2109453C3 DE 2109453 A DE2109453 A DE 2109453A DE 2109453 A DE2109453 A DE 2109453A DE 2109453 C3 DE2109453 C3 DE 2109453C3
- Authority
- DE
- Germany
- Prior art keywords
- water
- epoxides
- internal
- production
- vicinal
- 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 6
- 150000002334 glycols Chemical group 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000002118 epoxides Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 cyclic epoxides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- 125000003827 glycol group Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- VLJLXEKIAALSJE-UHFFFAOYSA-N 13-oxabicyclo[10.1.0]tridecane Chemical compound C1CCCCCCCCCC2OC21 VLJLXEKIAALSJE-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Manufacture And Refinement Of Metals (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2109453A DE2109453C3 (de) | 1971-02-27 | 1971-02-27 | Verfahren zur Herstellung von vicinalen Glykolen |
| BE779906A BE779906A (fr) | 1971-02-27 | 1972-02-25 | Procede pour la fabrication de diols vicinaux |
| NL7202506A NL7202506A (OSRAM) | 1971-02-27 | 1972-02-25 | |
| IT67611/72A IT953937B (it) | 1971-02-27 | 1972-02-26 | Procedimento per la produzione di dioli vicinali |
| FR7206702A FR2126460B1 (OSRAM) | 1971-02-27 | 1972-02-28 | |
| GB908772A GB1338196A (en) | 1971-02-27 | 1972-02-28 | Process for the production of vicinal diols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2109453A DE2109453C3 (de) | 1971-02-27 | 1971-02-27 | Verfahren zur Herstellung von vicinalen Glykolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2109453A1 DE2109453A1 (de) | 1972-09-28 |
| DE2109453B2 DE2109453B2 (de) | 1973-05-17 |
| DE2109453C3 true DE2109453C3 (de) | 1974-01-10 |
Family
ID=5800052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2109453A Expired DE2109453C3 (de) | 1971-02-27 | 1971-02-27 | Verfahren zur Herstellung von vicinalen Glykolen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE779906A (OSRAM) |
| DE (1) | DE2109453C3 (OSRAM) |
| FR (1) | FR2126460B1 (OSRAM) |
| GB (1) | GB1338196A (OSRAM) |
| IT (1) | IT953937B (OSRAM) |
| NL (1) | NL7202506A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2256907C3 (de) * | 1972-11-20 | 1982-03-18 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur Herstellung von vicinalen Di- und Polyolen |
| DE2931753C2 (de) * | 1979-08-04 | 1984-10-04 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von vicinalen Alkylenglykolen |
| DE2938154A1 (de) * | 1979-09-21 | 1981-04-09 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 1,2-diolen hoeherer kohlenstoffzahl |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB686402A (en) * | 1950-03-11 | 1953-01-21 | Distillers Co Yeast Ltd | Manufacture of glycols |
| US3475499A (en) * | 1967-03-23 | 1969-10-28 | Halcon International Inc | Preparation of glycols and glycol ethers |
-
1971
- 1971-02-27 DE DE2109453A patent/DE2109453C3/de not_active Expired
-
1972
- 1972-02-25 NL NL7202506A patent/NL7202506A/xx unknown
- 1972-02-25 BE BE779906A patent/BE779906A/xx not_active IP Right Cessation
- 1972-02-26 IT IT67611/72A patent/IT953937B/it active
- 1972-02-28 GB GB908772A patent/GB1338196A/en not_active Expired
- 1972-02-28 FR FR7206702A patent/FR2126460B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE779906A (fr) | 1972-06-16 |
| DE2109453B2 (de) | 1973-05-17 |
| FR2126460B1 (OSRAM) | 1977-04-01 |
| NL7202506A (OSRAM) | 1972-08-29 |
| DE2109453A1 (de) | 1972-09-28 |
| IT953937B (it) | 1973-08-10 |
| GB1338196A (en) | 1973-11-21 |
| FR2126460A1 (OSRAM) | 1972-10-06 |
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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 |