DE1967147C2 - Verfahren zur Herstellung von Glyoxal durch Dampfphasenoxydation von Athylenglykol - Google Patents
Verfahren zur Herstellung von Glyoxal durch Dampfphasenoxydation von AthylenglykolInfo
- Publication number
- DE1967147C2 DE1967147C2 DE19691967147 DE1967147A DE1967147C2 DE 1967147 C2 DE1967147 C2 DE 1967147C2 DE 19691967147 DE19691967147 DE 19691967147 DE 1967147 A DE1967147 A DE 1967147A DE 1967147 C2 DE1967147 C2 DE 1967147C2
- Authority
- DE
- Germany
- Prior art keywords
- glyoxal
- ethylene glycol
- catalyst
- solution
- percent
- 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 111
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 108
- 229940015043 glyoxal Drugs 0.000 title claims description 56
- 230000003647 oxidation Effects 0.000 title claims description 20
- 238000007254 oxidation reaction Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 12
- 239000012808 vapor phase Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000007789 gas Substances 0.000 claims description 38
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000012535 impurity Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003957 anion exchange resin Substances 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 3
- 238000007514 turning Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 9
- 235000005985 organic acids Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YLVACWCCJCZITJ-UHFFFAOYSA-N 1,4-dioxane-2,3-diol Chemical compound OC1OCCOC1O YLVACWCCJCZITJ-UHFFFAOYSA-N 0.000 description 8
- 229960004275 glycolic acid Drugs 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 hydroxycarbonyl compounds Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 238000005705 Cannizzaro reaction Methods 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/835—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with germanium, tin or lead
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/843—Arsenic, antimony or bismuth
-
- 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
- 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
- C07C45/39—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 secondary hydroxyl group
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
-
- 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
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- 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
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- 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
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2142268A GB1272592A (en) | 1968-05-06 | 1968-05-06 | Vapour phase oxidation of hydroxy compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1967147B1 DE1967147B1 (de) | 1979-06-13 |
| DE1967147C2 true DE1967147C2 (de) | 1980-02-14 |
Family
ID=10162679
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691967147 Expired DE1967147C2 (de) | 1968-05-06 | 1969-05-06 | Verfahren zur Herstellung von Glyoxal durch Dampfphasenoxydation von Athylenglykol |
| DE19691923048 Expired DE1923048C3 (de) | 1968-05-06 | 1969-05-06 | Verfahren zur Herstellung von Dicarbonylverbindungen durch Dampfphasenoxydation eines aliphatischen Diols bzw. von Cyclohexan-l,2-diol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691923048 Expired DE1923048C3 (de) | 1968-05-06 | 1969-05-06 | Verfahren zur Herstellung von Dicarbonylverbindungen durch Dampfphasenoxydation eines aliphatischen Diols bzw. von Cyclohexan-l,2-diol |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0271812A1 (de) * | 1986-12-19 | 1988-06-22 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Carbonylverbindungen |
| EP0287884A1 (de) * | 1987-04-15 | 1988-10-26 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Carbonylverbindungen |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1064963A (en) * | 1975-07-31 | 1979-10-23 | American Cyanamid Company | Vapor phase oxidation process for glyoxal |
| US4258216A (en) * | 1975-07-31 | 1981-03-24 | American Cyanamid Company | Vapor phase oxidation process for glyoxal |
| JPS5490109A (en) * | 1977-12-24 | 1979-07-17 | Basf Ag | Manufacture of fatty hydroxycarbonyl compound etherified with fatty group |
| DE2803318A1 (de) * | 1978-01-26 | 1979-08-09 | Basf Ag | Verfahren zur herstellung von glyoxal |
| 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 |
| DE3012004A1 (de) * | 1980-03-28 | 1981-10-15 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von methylglyoxal |
| JPS5838227A (ja) * | 1981-09-01 | 1983-03-05 | Mitsui Toatsu Chem Inc | アルデヒドの製造法 |
| DE3213227A1 (de) * | 1982-04-08 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von formaldehyd |
| US4503261A (en) * | 1982-07-22 | 1985-03-05 | Basf Aktiengesellschaft | Preparation of glyoxal |
| US4555583A (en) * | 1982-08-30 | 1985-11-26 | Mitsui Toatsu Chemicals, Incorporated | Preparation process for glyoxal |
| US4439625A (en) * | 1982-09-29 | 1984-03-27 | E. I. Du Pont De Nemours And Company | Production of formaldehyde |
| US4599459A (en) * | 1984-08-31 | 1986-07-08 | Masanao Hirose | Method for the ultrasonic treatment of a dilute alcoholic solution |
| RU2321577C2 (ru) * | 2006-04-25 | 2008-04-10 | Институт органического синтеза УрО РАН | Способ получения глиоксальсодержащих продуктов |
| CN101472873A (zh) * | 2006-05-17 | 2009-07-01 | 巴斯夫欧洲公司 | 烃氧化反应中的温度控制 |
| WO2007132011A1 (de) * | 2006-05-17 | 2007-11-22 | Basf Aktiengesellschaft | Verfahren zur herstellung vicinaler dioxoverbindungen durch oxidation vicinaler dihydroxyverbindungen an einer strukturierten katalysatorschüttung |
| DE102008018480B4 (de) | 2007-04-13 | 2020-10-15 | Basf Se | Verfahren zur Herstellung vicinaler Dioxoverbindungen durch Oxidation vicinaler Dihydroxyverbindungen |
| DE102008002535A1 (de) | 2007-06-25 | 2009-01-02 | Basf Se | Verfahren zur Herstellung vicinaler Dioxoverbindungen durch Oxidation vicinaler Dihydroxyverbindungen an Silber enthaltenden Dünnschichtkatalysatoren |
| RU2392170C1 (ru) * | 2008-10-06 | 2010-06-20 | Геращенко Григорий Аркадьевич | Элемент обводов для надувной лодки (варианты) |
| EP2382175B1 (de) | 2008-12-29 | 2015-02-25 | Basf Se | Verfahren zur reinigung wässriger glyoxal-lösungen |
| US8461396B2 (en) | 2010-10-01 | 2013-06-11 | Basf Se | Process for purifying aqueous glyoxal solutions |
| EP2621878B1 (de) | 2010-10-01 | 2016-06-01 | Basf Se | Verfahren zur reinigung wässriger glyoxal-lösungen |
| EP4214185B1 (en) | 2020-09-17 | 2024-07-17 | Basf Se | Process for the production of glyoxal |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1497817A (en) * | 1918-08-13 | 1924-06-17 | Seth B Hunt | Process of making acetone and other ketones |
| US2051266A (en) * | 1935-03-23 | 1936-08-18 | Shell Dev | Catalytic oxidation of polyhydric alcohols |
| US2462107A (en) * | 1943-05-03 | 1949-02-22 | Ninol Dev Co | Process for preparation of diacetyl |
| FR1060331A (fr) * | 1951-08-02 | 1954-04-01 | Basf Ag | Procédé pour obtenir les uréines du glyoxal |
| US3049446A (en) * | 1960-02-05 | 1962-08-14 | Sun Chemical Corp | Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials |
-
1968
- 1968-05-06 GB GB2142268A patent/GB1272592A/en not_active Expired
-
1969
- 1969-05-05 NO NO184469A patent/NO133034C/no unknown
- 1969-05-05 NL NL6906866A patent/NL168487C/xx not_active IP Right Cessation
- 1969-05-05 CH CH684269A patent/CH535193A/de not_active IP Right Cessation
- 1969-05-06 SE SE637769A patent/SE363816B/xx unknown
- 1969-05-06 BR BR20855169A patent/BR6908551D0/pt unknown
- 1969-05-06 FR FR6914418A patent/FR2007925A1/fr active Pending
- 1969-05-06 BE BE732584D patent/BE732584A/xx not_active IP Right Cessation
- 1969-05-06 DE DE19691967147 patent/DE1967147C2/de not_active Expired
- 1969-05-06 DE DE19691923048 patent/DE1923048C3/de not_active Expired
- 1969-05-06 ES ES366867A patent/ES366867A1/es not_active Expired
-
1972
- 1972-08-14 JP JP8137872A patent/JPS4930807B1/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0271812A1 (de) * | 1986-12-19 | 1988-06-22 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Carbonylverbindungen |
| EP0287884A1 (de) * | 1987-04-15 | 1988-10-26 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Carbonylverbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL168487C (nl) | 1982-04-16 |
| DE1923048A1 (de) | 1969-11-20 |
| NO133034B (enrdf_load_stackoverflow) | 1975-11-17 |
| SE363816B (enrdf_load_stackoverflow) | 1974-02-04 |
| DE1923048C3 (de) | 1980-06-19 |
| FR2007925A1 (enrdf_load_stackoverflow) | 1970-01-16 |
| BR6908551D0 (pt) | 1973-01-04 |
| BE732584A (enrdf_load_stackoverflow) | 1969-11-06 |
| CH535193A (de) | 1973-03-31 |
| DE1923048B2 (de) | 1979-07-19 |
| JPS4930807B1 (enrdf_load_stackoverflow) | 1974-08-16 |
| ES366867A1 (es) | 1971-06-16 |
| GB1272592A (en) | 1972-05-03 |
| NL168487B (nl) | 1981-11-16 |
| NO133034C (enrdf_load_stackoverflow) | 1976-02-25 |
| NL6906866A (enrdf_load_stackoverflow) | 1969-11-10 |
| DE1967147B1 (de) | 1979-06-13 |
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