BE511229A - - Google Patents
Info
- Publication number
- BE511229A BE511229A BE511229DA BE511229A BE 511229 A BE511229 A BE 511229A BE 511229D A BE511229D A BE 511229DA BE 511229 A BE511229 A BE 511229A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- oxidation
- derivatives
- pressure
- carried out
- Prior art date
Links
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
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl groups
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)
Description
<EMI ID=1.1>
NITRIQUE.
L'invention concerne un procédé qui convient parfaitement pour
<EMI ID=2.1>
élevées. Vu l'application d'une température et d'une pression élevées, l'oxydation peut s'effectuer en peu de temps et avec un haut rendement, sans l'emploi de catalyseurs spéciaux quelconques.
<EMI ID=3.1>
oxydation du diphénylméthane en benzophénone et la transformation par oxydation du benzyltoluène en acide benzoylbenzoique.
Le procédé de l'invention n'est cependant pas limité à ces composés mais est également applicable à leur homologues et dérivés par substitutiono
Exemple lo Cette oxydation", tout comme celle décrite dans l'exem-
<EMI ID=4.1>
xydable et muni d'un agitateur/ d'un thermomètre et d'un dispositif pour charger l'autoclave sous pression'.
Ce dernier appareil consistait en récipients inattaquables aux-acides,. dont
<EMI ID=5.1>
permettait de recharger l'autoclave avec les constituants réactionnels au cours de la réaction.
Ces récipients pouvaient également servir à égaliser la pression dans l'autoclave en cours de réaction. L'évacuation des gaz nitreux pouvait se faire au besoin à travers ces récipients ou à travers une soupape d'évacuation spéciale.
L'autoclave était chérgée de diphénylméthane et d'acide nitri- <EMI ID=6.1>
Le produit de la réaction a été séparé.. lavé dans l'eau et dans une solution de soude diluée et ensuite distillée sous vide On a recueilli une fraction principale;! pour laquelle les constantes ci-après ont été dé-terminées. A titre de comparaisons on trouvera ci-après les caractéristiques théoriques et celles données dans la littérature antérieure pour le diphénylméthane et le benzophénone.
<EMI ID=7.1>
Il résulte des données ci-dessus que le produit principal obtenu par oxydation est représenté par le benzophénoneo
Exemple 2 % On a employé le même appareillage que celui de
<EMI ID=8.1>
autoclave du benzyltoluène (un mélange d'isomères) avec un excès de 50% diacide nitrique dilué à 15%. " L'oxydation a été effectuée à une température ne dépassant pas 203[deg.]C et à une pression ne dépassant pas 32 kg/cm2<,
L'analyse du produit a fourni les chiffres ci-après.
A titre de comparaison on a donné les valeurs théoriques pour l'acide
<EMI ID=9.1>
<EMI ID=10.1>
<EMI ID=11.1>
partie seulement de l'acide nitrique était introduite dès le début. Lorsque celle-ci a réagit;, on a introduit le restant à travers un récipient sous pressions après quoi la réaction a recommence..
<EMI ID=12.1>
Des oxydations analogues ont en outre été effectuées avec
un acide plus forts par exemple à 30% et avec un excès différente avec des températures., pressions et méthodes de chargement différentes.
<EMI ID=13.1>
cipients sous pression. L�évacuation peut se faire en continu à travers un tube muni de soupapes commandées par la pression
Une analyse carbone-hydrogène du produit brut des exemples 2-3
a fait ressortir que celui-ci consistait essentiellement en acides benzbyl-
<EMI ID=14.1>
tion nouveau et économique de produits de cette nature.
Ce procédé a également été essayé avec de bons résultats sur des dérives par substitution de benzyltoluène par exemple les nitro-dérives.
REVENDICATIONS.
1. Procédé d'oxydation du groupe méthylène du diphénylméthane et de ses homologues et des dérivés par substitution de ces composés, par l'acide nitrique, caractérisé en ce que l'oxydation s'effectue à une pression supérieure à la pression atmosphérique et à une température supérieu-
<EMI ID=15.1>
<EMI ID = 1.1>
NITRIC.
The invention relates to a method which is ideally suited for
<EMI ID = 2.1>
high. Due to the application of high temperature and pressure, the oxidation can be carried out in a short time and with high efficiency, without the use of any special catalysts.
<EMI ID = 3.1>
oxidation of diphenylmethane to benzophenone and oxidation transformation of benzyltoluene to benzoylbenzoic acid.
The process of the invention is however not limited to these compounds but is also applicable to their homologues and derivatives by substitution.
Example lo This oxidation ", like that described in the example
<EMI ID = 4.1>
xable and provided with a stirrer / thermometer and a device for loading the autoclave under pressure.
The latter apparatus consisted of acid-proof receptacles. whose
<EMI ID = 5.1>
allowed the autoclave to be recharged with the reaction constituents during the reaction.
These vessels could also be used to equalize the pressure in the autoclave during the reaction. The nitrous gases could be evacuated if necessary through these containers or through a special evacuation valve.
The autoclave was loaded with diphenylmethane and nitri- <EMI ID = 6.1>
The reaction product was separated, washed with water and dilute sodium hydroxide solution and then vacuum distilled. A main fraction was collected; for which the following constants have been determined. By way of comparisons, the theoretical characteristics and those given in the previous literature for diphenylmethane and benzophenone will be found below.
<EMI ID = 7.1>
It follows from the above data that the main product obtained by oxidation is represented by benzophenoneo
Example 2% The same apparatus as that of
<EMI ID = 8.1>
autoclave benzyltoluene (a mixture of isomers) with an excess of 50% nitric diacid diluted to 15%. "The oxidation was carried out at a temperature not exceeding 203 [deg.] C and at a pressure not exceeding 32 kg / cm2 <,
Product analysis yielded the following figures.
For comparison we gave the theoretical values for the acid
<EMI ID = 9.1>
<EMI ID = 10.1>
<EMI ID = 11.1>
only part of the nitric acid was introduced from the start. When this reacted, the remainder was introduced through a pressure vessel after which the reaction recommenced.
<EMI ID = 12.1>
Similar oxidations were also carried out with
a stronger acid for example at 30% and with a different excess with different temperatures, pressures and loading methods.
<EMI ID = 13.1>
pressure vessels. The evacuation can be done continuously through a tube with pressure-controlled valves
A carbon-hydrogen analysis of the crude product of Examples 2-3
showed that this consisted mainly of benzbyl- acids
<EMI ID = 14.1>
new and economical tion of products of this nature.
This process has also been tried with good results on derivatives by substitution of benzyltoluene, for example nitro-derivatives.
CLAIMS.
1. A process for the oxidation of the methylene group of diphenylmethane and its homologues and derivatives by substitution of these compounds, with nitric acid, characterized in that the oxidation is carried out at a pressure greater than atmospheric pressure and at a higher temperature
<EMI ID = 15.1>
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE310497X | 1951-05-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
BE511229A true BE511229A (en) |
Family
ID=20307622
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BE511229D BE511229A (en) | 1951-05-08 |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE511229A (en) |
CH (1) | CH310497A (en) |
DE (1) | DE934525C (en) |
FR (1) | FR1055446A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3031506A (en) * | 1958-07-29 | 1962-04-24 | Rohm & Haas | Method for the preparation of diaryl ketones |
US4022838A (en) * | 1975-05-27 | 1977-05-10 | Gulf Research & Development Company | Process for preparing diarylketones |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE539476C (en) * | 1929-03-24 | 1931-11-26 | I G Farbenindustrie Akt Ges | Process for the oxidation of organic compounds in the liquid phase by means of gases containing oxygen |
-
0
- BE BE511229D patent/BE511229A/fr unknown
-
1952
- 1952-05-05 FR FR1055446D patent/FR1055446A/en not_active Expired
- 1952-05-06 CH CH310497D patent/CH310497A/en unknown
- 1952-05-06 DE DEA15717A patent/DE934525C/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR1055446A (en) | 1954-02-18 |
DE934525C (en) | 1955-10-27 |
CH310497A (en) | 1955-10-31 |
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