DE2501743C2 - Verfahren zur Abtrennung von Glyoxylsäure aus wässrigen, Glyoxylsäure und Glyoxal enthaltenden Gemischen - Google Patents
Verfahren zur Abtrennung von Glyoxylsäure aus wässrigen, Glyoxylsäure und Glyoxal enthaltenden GemischenInfo
- Publication number
- DE2501743C2 DE2501743C2 DE2501743A DE2501743A DE2501743C2 DE 2501743 C2 DE2501743 C2 DE 2501743C2 DE 2501743 A DE2501743 A DE 2501743A DE 2501743 A DE2501743 A DE 2501743A DE 2501743 C2 DE2501743 C2 DE 2501743C2
- Authority
- DE
- Germany
- Prior art keywords
- glyoxylic acid
- glyoxal
- acid
- separation
- mixtures containing
- 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
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 title claims description 74
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 title claims description 54
- 229940015043 glyoxal Drugs 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 title claims description 8
- 238000000926 separation method Methods 0.000 title description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 238000000605 extraction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 241000566113 Branta sandvicensis Species 0.000 description 2
- -1 Cyclopentanone methyl cyclopentanol Chemical compound 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical group CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- SEUTYDPWWXFDLF-UHFFFAOYSA-N O.C(C)(=O)OCC.CC(=O)CC Chemical compound O.C(C)(=O)OCC.CC(=O)CC SEUTYDPWWXFDLF-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- PTABKUAUBJZSEC-UHFFFAOYSA-N acetylene ethane-1,2-diol Chemical compound C#C.OCCO PTABKUAUBJZSEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- SOEVVANXSDKPIY-UHFFFAOYSA-M sodium glyoxylate Chemical compound [Na+].[O-]C(=O)C=O SOEVVANXSDKPIY-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2501743A DE2501743C2 (de) | 1975-01-17 | 1975-01-17 | Verfahren zur Abtrennung von Glyoxylsäure aus wässrigen, Glyoxylsäure und Glyoxal enthaltenden Gemischen |
| US05/645,112 US4026929A (en) | 1975-01-17 | 1975-12-29 | Selective extraction of glyoxylic acid from aqueous mixture with glyoxal |
| CH1692575A CH595313A5 (enExample) | 1975-01-17 | 1975-12-31 | |
| JP51002903A JPS5755697B2 (enExample) | 1975-01-17 | 1976-01-14 | |
| NLAANVRAGE7600383,A NL179367C (nl) | 1975-01-17 | 1976-01-15 | Werkwijze voor het afscheiden van glyoxylzuur uit waterrijke, glyoxylzuur en glyoxal bevattende mengsels. |
| GB172376A GB1471852A (en) | 1975-01-17 | 1976-01-16 | Process for isolating glyoxylic acid from mixtures containing glyoxylic acid from mixtures containing glyoxal and glyoxylic acid |
| FR7601143A FR2297830A1 (fr) | 1975-01-17 | 1976-01-16 | Procede d |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2501743A DE2501743C2 (de) | 1975-01-17 | 1975-01-17 | Verfahren zur Abtrennung von Glyoxylsäure aus wässrigen, Glyoxylsäure und Glyoxal enthaltenden Gemischen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2501743A1 DE2501743A1 (de) | 1976-07-22 |
| DE2501743C2 true DE2501743C2 (de) | 1982-07-15 |
Family
ID=5936655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2501743A Expired DE2501743C2 (de) | 1975-01-17 | 1975-01-17 | Verfahren zur Abtrennung von Glyoxylsäure aus wässrigen, Glyoxylsäure und Glyoxal enthaltenden Gemischen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4026929A (enExample) |
| JP (1) | JPS5755697B2 (enExample) |
| CH (1) | CH595313A5 (enExample) |
| DE (1) | DE2501743C2 (enExample) |
| FR (1) | FR2297830A1 (enExample) |
| GB (1) | GB1471852A (enExample) |
| NL (1) | NL179367C (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2540105B1 (fr) * | 1983-01-29 | 1986-02-14 | Basf Ag | Procede pour la purification de solutions aqueuses de glyoxal |
| DE3334863A1 (de) * | 1983-09-27 | 1985-04-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von waessrigen glyoxylsaeureloesungen |
| AT392638B (de) * | 1989-06-05 | 1991-05-10 | Chemie Linz Gmbh | Verfahren zur kontinuierlichen herstellung einer konzentrierten waessrigen loesung von glyoxylsaeure |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644508A (en) * | 1969-07-23 | 1972-02-22 | United States Steel Corp | Process for the recovery of glyoxylic acid |
-
1975
- 1975-01-17 DE DE2501743A patent/DE2501743C2/de not_active Expired
- 1975-12-29 US US05/645,112 patent/US4026929A/en not_active Expired - Lifetime
- 1975-12-31 CH CH1692575A patent/CH595313A5/xx not_active IP Right Cessation
-
1976
- 1976-01-14 JP JP51002903A patent/JPS5755697B2/ja not_active Expired
- 1976-01-15 NL NLAANVRAGE7600383,A patent/NL179367C/xx not_active IP Right Cessation
- 1976-01-16 FR FR7601143A patent/FR2297830A1/fr active Granted
- 1976-01-16 GB GB172376A patent/GB1471852A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2297830A1 (fr) | 1976-08-13 |
| CH595313A5 (enExample) | 1978-02-15 |
| NL7600383A (nl) | 1976-07-20 |
| FR2297830B1 (enExample) | 1979-06-22 |
| GB1471852A (en) | 1977-04-27 |
| NL179367B (nl) | 1986-04-01 |
| US4026929A (en) | 1977-05-31 |
| JPS5195018A (enExample) | 1976-08-20 |
| NL179367C (nl) | 1986-09-01 |
| JPS5755697B2 (enExample) | 1982-11-25 |
| DE2501743A1 (de) | 1976-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |