DE2634439C2 - Verfahren zur Herstellung von Glyoxal - Google Patents
Verfahren zur Herstellung von GlyoxalInfo
- Publication number
- DE2634439C2 DE2634439C2 DE19762634439 DE2634439A DE2634439C2 DE 2634439 C2 DE2634439 C2 DE 2634439C2 DE 19762634439 DE19762634439 DE 19762634439 DE 2634439 A DE2634439 A DE 2634439A DE 2634439 C2 DE2634439 C2 DE 2634439C2
- Authority
- DE
- Germany
- Prior art keywords
- ethylene glycol
- glyoxal
- gas
- parts
- reactor
- 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
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 title claims description 65
- 229940015043 glyoxal Drugs 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 174
- 239000007789 gas Substances 0.000 claims description 43
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000008246 gaseous mixture Substances 0.000 claims description 23
- -1 bromine compound Chemical class 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000007865 diluting Methods 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 28
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 12
- 239000011261 inert gas Substances 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- 229950005228 bromoform Drugs 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
- ZDUOUNIIAGIPSD-UHFFFAOYSA-N 1,1,1-tribromoethane Chemical compound CC(Br)(Br)Br ZDUOUNIIAGIPSD-UHFFFAOYSA-N 0.000 description 1
- AONKGGMHQHWMSM-UHFFFAOYSA-N 1,1,1-tribromopropane Chemical compound CCC(Br)(Br)Br AONKGGMHQHWMSM-UHFFFAOYSA-N 0.000 description 1
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NTIGNJOEVBTPJJ-UHFFFAOYSA-N 3,3-dibromopentane Chemical compound CCC(Br)(Br)CC NTIGNJOEVBTPJJ-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/04—Electrodes or formation of dielectric layers thereon
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/12—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing more than one —CHO group
- C07C47/127—Glyoxal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60056075A | 1975-07-31 | 1975-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2634439A1 DE2634439A1 (de) | 1977-02-10 |
| DE2634439C2 true DE2634439C2 (de) | 1985-07-11 |
Family
ID=36778069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762634439 Expired DE2634439C2 (de) | 1975-07-31 | 1976-07-30 | Verfahren zur Herstellung von Glyoxal |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5946212B2 (fr) |
| BR (1) | BR7604682A (fr) |
| CA (1) | CA1064963A (fr) |
| DE (1) | DE2634439C2 (fr) |
| FR (1) | FR2319613A1 (fr) |
| GB (1) | GB1542900A (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2803318A1 (de) * | 1978-01-26 | 1979-08-09 | Basf Ag | Verfahren zur herstellung von glyoxal |
| DE2831229A1 (de) * | 1978-07-15 | 1980-01-31 | Basf Ag | Verfahren zur herstellung von diketonen |
| DE2832405A1 (de) * | 1978-07-24 | 1980-02-14 | Basf Ag | Verfahren zur herstellung von glyoxal aus aethylenglykol |
| DE2922599A1 (de) * | 1979-06-02 | 1980-12-04 | Basf Ag | Verfahren zur kontinuierlichen herstellung von glyoxal |
| DE3130800A1 (de) * | 1981-08-04 | 1983-02-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von glyoxal |
| US4503261A (en) * | 1982-07-22 | 1985-03-05 | Basf Aktiengesellschaft | Preparation of glyoxal |
| DE3390191C2 (de) * | 1982-08-30 | 1989-01-26 | Mitsui Toatsu Chemicals | Verfahren zur Herstellung von glyoxal |
| JPS5946237A (ja) * | 1982-09-09 | 1984-03-15 | Mitsubishi Petrochem Co Ltd | グリオキサ−ルの製造方法 |
| US4978803A (en) * | 1989-06-26 | 1990-12-18 | American Cyanamid Company | Vapor phase oxidation process for making glyoxal |
| DE19811288A1 (de) * | 1998-03-16 | 1999-09-23 | Basf Ag | Verfahren zur Herstellung von Carbonylverbindungen |
| DE69929435T2 (de) * | 1998-05-20 | 2006-09-14 | Nippon Shokubai Co., Ltd. | Verfahren zur herstellung von alpha-oxoaldehyden |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2339346A (en) * | 1940-07-30 | 1944-01-18 | Carbide & Carbon Chem Corp | Process for making dicarbonylic compounds |
| GB1272592A (en) * | 1968-05-06 | 1972-05-03 | Laporte Chemical | Vapour phase oxidation of hydroxy compounds |
-
1976
- 1976-06-22 CA CA255,418A patent/CA1064963A/fr not_active Expired
- 1976-06-28 GB GB2691376A patent/GB1542900A/en not_active Expired
- 1976-07-19 BR BR7604682A patent/BR7604682A/pt unknown
- 1976-07-30 DE DE19762634439 patent/DE2634439C2/de not_active Expired
- 1976-07-30 FR FR7623432A patent/FR2319613A1/fr active Granted
- 1976-07-31 JP JP9087576A patent/JPS5946212B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1064963A (fr) | 1979-10-23 |
| FR2319613A1 (fr) | 1977-02-25 |
| BR7604682A (pt) | 1977-08-02 |
| GB1542900A (en) | 1979-03-28 |
| FR2319613B1 (fr) | 1982-07-23 |
| DE2634439A1 (de) | 1977-02-10 |
| JPS5217408A (en) | 1977-02-09 |
| JPS5946212B2 (ja) | 1984-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE941428C (de) | Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen | |
| EP0467144B1 (fr) | Masses de formule générale | |
| DE2220799C3 (de) | Verfahren zur Herstellung von Acrylsäure durch Oxydation von Acrolein | |
| EP0356703A2 (fr) | Procédé pour l'oxidation de 5-hydroxymétyl furfural | |
| DE2634439C2 (de) | Verfahren zur Herstellung von Glyoxal | |
| DE2610249C2 (de) | Verfahren zur Herstellung von Acrylsäure bzw. Methacrylsäure | |
| DE2523757C3 (de) | Verfahren zur Herstellung von Methacrylsäure durch katalytische Oxidation von Methacrolein mit Sauerstoff | |
| DE1962431A1 (de) | Verfahren zur Herstellung ungesaettigter aliphatischer Carbonsaeuren | |
| DE897560C (de) | Verfahren zur Herstellung von ungesaettigten Nitrilen | |
| DE2941341C2 (de) | Verfahren zur Herstellung von Methacrolein | |
| DE2164905A1 (fr) | ||
| DE3030463A1 (de) | Verfahren zur herstellung von aromatischen polycarbonsaeuren | |
| DE2353131B2 (de) | Katalysator für die Gasphasenoxydation von ungesättigten Aldehyden zu ungesättigten Carbonsäuren | |
| DE1593149C3 (de) | Verfahren zur Herstellung von Acrylnitril bzw. Methacrylnitril aus Propylen bzw. Isobutylen | |
| DE2337510C2 (de) | Verfahren zur Herstellung von Acrylsäure oder Methacrylsäure | |
| DE2632395C3 (de) | Katalysator für die Verwendung zur Herstellung von Anisaldehyd | |
| DE2161471C3 (de) | Verfahren zur Herstellung von Acrolein und Acrylsäure | |
| DE2244264B2 (fr) | ||
| DE1468428B2 (de) | Verfahren zur Herstellung von Acrylsäure bzw. Methacrylsäure aus Propylen bzw. Isobutylen | |
| DE2104849A1 (de) | Verfahren zur Herstellung von Acrolein oder Methacrolein | |
| DE1805355A1 (de) | Verfahren zur Herstellung von Ketonen aus Olefinen | |
| DE2454587C2 (de) | Verfahren zur Herstellung von Methacrylsäure | |
| DE1177628B (de) | Verfahren zur Herstellung von Akrolein oder Methakrolein durch katalytisch Oxydation von Propylen oder Isobutylen. | |
| DE2040455C3 (de) | Verfahren zur Herstellung von Essigsäure | |
| DE2552652C3 (de) | Verfahren zum Herstellen von Dibenzofuran |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |