DE239651C - - Google Patents
Info
- Publication number
- DE239651C DE239651C DENDAT239651D DE239651DA DE239651C DE 239651 C DE239651 C DE 239651C DE NDAT239651 D DENDAT239651 D DE NDAT239651D DE 239651D A DE239651D A DE 239651DA DE 239651 C DE239651 C DE 239651C
- Authority
- DE
- Germany
- Prior art keywords
- contact
- mass
- oxygen
- aldehydes
- oxidation
- 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.)
- Active
Links
- 239000000126 substance Substances 0.000 claims description 9
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical class O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- -1 B. methyl alcohol Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C45/27—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
- C07C45/33—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 CHx-moieties
- C07C45/34—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 CHx-moieties in unsaturated compounds
- C07C45/36—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 CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
^PATENTSCHRIFT^ PATENT LETTERING
Ki 239651 -KLASSE 12 o. GRUPPE Ki 239651 - CLASS 12 or GROUP
Patentiert im Deutschen Reiche vom 25. Juni 1909 ab.Patented in the German Empire on June 25, 1909.
Vorliegende Erfindung bezieht sich auf ein ■Verfahren zur Oxydation von aromatischen Kohlenwasserstoffen und deren Substitutionsprodukten, wie z. B. Chlortoluol, sowie von Alkoholen, wie z. B. Methylalkohol, durch Überleiten von Dämpfen der zu oxydierenden Körper in Mischung mit Sauerstoff oder sauerstoffhaltigen Gasen über Kontaktmassen bei geeigneter erhöhter Temperatur, und bezwecktThe present invention relates to a method for the oxidation of aromatic substances Hydrocarbons and their substitution products, such as. B. chlorotoluene, as well as from Alcohols such as B. methyl alcohol, by passing over vapors to be oxidized Bodies in a mixture with oxygen or oxygen-containing gases via contact masses suitable elevated temperature, and intended
ίο die Bildung von Aldehyden durch Wahl einer geeigneten Kontaktmasse. Der Erfindung zufolge werden als Kontaktmasse die Rückstände der Reduktion von Salzen der Chromsäure mit flüchtigen Basen, insbesondere von Ammonsalzen der Chromsäure, benutzt. Im Unterschiede von auf anderem Wege gewönnenem Chromoxyd besitzt diese Masse für die genannten Stoffe eine besondere Aktivität, welche die erfolgreiche Oxydation ermöglicht.ίο the formation of aldehydes by choosing one suitable contact ground. According to the invention, the residues are used as the contact mass the reduction of salts of chromic acid with volatile bases, in particular of ammonium salts of chromic acid. in the Differences from chromium oxide obtained in other ways are what this mass possesses for them These substances have a special activity that enables successful oxidation.
Eine für den Zweck geeignete Kontaktmasse erhält man z. B., wenn man chromsaures Ammon oder doppeltchromsaures Ammon verglüht oder mit Methylalkohol befeuchtet und anzündet. Diese in chemischem Sinne im wesentlichen aus Chromoxyd bestehende Masse kann unmittelbar oder vermischt mit anderen Substanzen, insbesondere mit Stoffen, die sonst als Kontaktkörper geeignet sind, aber für sich allein eine Oxydation der aromatischen Kohlenwasserstoffe usw. zu Aldehyden nicht herbeizuführen vermögen, verwendet werden. Die Wirksamkeit dieser Masse beruht anscheinend auf ihrem von der Flüchtigkeit der Base des verwendeten Salzes herrührenden geringen Volumgewicht. A contact compound suitable for the purpose is obtained, for. B. if you use chromic ammonium or ammonium double chromate burned up or moistened with methyl alcohol and ignited. This in the chemical sense in Substantially consisting of chromium oxide mass can be used directly or mixed with others Substances, especially with substances that are otherwise suitable as contact bodies, but for themselves alone not to bring about an oxidation of the aromatic hydrocarbons etc. to aldehydes able to be used. The effectiveness of this mass is apparently based on their low volume weight resulting from the volatility of the base of the salt used.
Bei der Ausführung des Verfahrens verfährt man in der gleichen Weise, wie es bei der Oxydation von Stoffen unter Benutzung von Kontaktmassen üblich ist.The procedure for carrying out the procedure is the same as that for Oxidation of substances using contact masses is common.
Man kann beispielsweise käufliches Xylol in der Weise in ein Gemisch der isomeren Toluylaldehyde umwandeln, daß man Xyloldämpfe, mit Luft vermischt, über die Kontaktmasse streichen läßt, welche vorher so weit erhitzt wird, daß beim Überleiten der mit Luft vermischten Dämpfe die Kontaktsubstanz ins Glühen kommt. Die über die Kontaktmasse hinweggeleiteten Dämpfe und ihre Umsetzungsprodukte werden darauf durch eine Kühlvorrichtung geschickt, in welcher eine Kondensation eintritt. Das Kondensat enthält neben unzersetztem Xylol, Wasser und Verbrennungsprodukten Toluylaldehyde, welche letzteren nach bekannten Verfahren, beispielsweise über die Natriumbisulfitverbindung, getrennt werden.For example, commercial xylene can be converted into a mixture of the isomers in this way Convert toluyl aldehydes, so that xylene vapors, mixed with air, can be stroked over the contact mass, which is previously heated so far that when passing over the vapors mixed with air cause the contact substance to glow. The ones about the Contact mass diverted vapors and their conversion products are due to it sent a cooling device in which a condensation occurs. The condensate contains undecomposed xylene, water and combustion products, toluic aldehydes, which the latter separated by known processes, for example via the sodium bisulfite compound will.
Bei einem Versuch, bei welchem 100 g Xyloldämpfe über die Kontaktmasse geleitet wurden, ergab sich eine Ausbeute von etwa 30 bis 40 g Toluylaldehyde. Die Luftzufuhr wurde dabei so gewählt, daß die Kontaktsubstanz in dunkle Rotglut geriet.In an experiment in which 100 g of xylene vapors were passed over the contact mass, the yield was about 30 to 40 grams of toluic aldehyde. The air supply was chosen so that the contact substance turned into a dark red heat.
Claims (1)
Verfahren zur Darstellung von Aldehyden aus aromatischen Kohlenwasserstoffen und deren Substitutionsprodukten oder aus Alkoholen durch Oxydation mit Sauerstoff oder sauerstoffhaltigen Gasen in Gegenwarf einer Kontaktsubstanz, dadurch gekennzeichnet, daß als Kontaktmasse die Rückstände der Reduktion von Salzen der Chromsäure mit flüchtigen Basen, insbesondere von Ammonsalzen der Chromsäure, benutzt werden.Patent claim:
Process for the preparation of aldehydes from aromatic hydrocarbons and their substitution products or from alcohols by oxidation with oxygen or oxygen-containing gases in the presence of a contact substance, characterized in that the residues of the reduction of salts of chromic acid with volatile bases, in particular ammonium salts of chromic acid, are used as the contact mass. to be used.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE239651C true DE239651C (en) |
Family
ID=499075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT239651D Active DE239651C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE239651C (en) |
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0
- DE DENDAT239651D patent/DE239651C/de active Active
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