Author Topic: Benzoic Acid via Toluene  (Read 5021 times)

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foxy2

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Re: Benzoic Acid via Toluene
« Reply #20 on: November 27, 2001, 10:27:00 PM »
Buy it!!
Is there a less suspicious chemical??
There are non-chemical companies that sell it.

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foxy2

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Re: Benzoic Acid via Toluene
« Reply #21 on: November 27, 2001, 10:59:00 PM »
Surfactant-assisted permanganate oxidation of aromatic compounds.    
Jursic, Branko.  
Can. J. Chem.  (1989),  67(9),  1381-3. 

Abstract
KMnO4 in aq. solns. of surfactant can be used to oxidize arom. compds. to the corresponding acids.  Oxidn. of arom. alcs. and aldehydes proceeds under mild reaction conditions, while the oxidn. of alkylbenzenes requires higher temps.  The yields are very high and the work-up is simple.


New method for synthesis of benzoic acid.    
Bratulescu, George; Le Bigot, Yves; Delmas, Michel.   
Ecole National Superieure de Chimie de Toulouse,  Franta,  Rom.    Rev. Chim. (Bucharest)  (2000),  51(5),  357-358.
ISSN: 0034-7752.  Journal  written in Romanian.
Abstract
Benzoic acid was prepd. in 60% yield by toluene oxidn. with potassium permanganate on aluminum chloride hexahydrate support without solvent,using microwave irradn.


Mechanochemical oxidation of organic model compounds by means of potassium permanganate. (In German)   
Nuchter, Matthias; Ondruschka, Bernd; Trotzki, Ronald.      
J. Prakt. Chem. (Weinheim, Ger.)  (2000),  342(7),  720-724.
Abstract
According to the investigation of solvent-free oxidns. of org. model compds. with KMnO4 on inorg. carriers, mechanochem. stimulation can induce oxidns.  In the case of benzyl-type arenes, these conversions are selective at good yields.  Olefines react to yield carboxylic acids.  The presence of water mostly enhances the yield.


Catalytic oxidation of toluene to benzoic acid and oxidation of other aromatic hydrocarbons.    
Zhang, Xiang-Fu; Shi, Xiao-Tian.  
Hecheng Huaxue  (1998),  6(4),  433-437.  
Journal  written in Chinese.
Abstract
Benzoic acid was obtaines in 85% yield by catalytic oxidn. of toluene in acetic acid in the presence of cobalt trichloroacetate, manganese trichloroacete, and ammonium bromide as catalysts, and acetonitrile as accelerator, pure oxygen as oxidizing agent at temp. 110°C ± 2°C for 15 h.  This catalytic system exhibited the same activity for other arom. hydrocarbons.


Investigation of ultrasound catalyzed oxidation of arylalkanes using aqueous potassium permanganate.
Soudagar, S.R.; Samant, S.D.  
Ultrason. Sonochem.  (1995),  Volume Date 1995,  2(1),  S15-S18.
Abstract
Various arylalkanes, e.g., R1C6H4Me (R1 = H, 2-Me, 4-NO2) were oxidized to the corresponding arylcarboxylic acids, e.g., BzOH, 1,2-(HO2C)2C6H4, and 4-O2NC6H4CO2H, using aq. KMnO4 under heterogeneous conditions and in the presence of ultrasound.  The toluene/water system was studied in detail.  Various parameters, such as the effect of stirring, quantity of KMnO4 and reaction time were optimized.  The reaction was found to be considerably accelerated at ambient temp.


Catalytic-liquid phase oxidation of toluene.    
Chaudhri, Tanweer A.; Ahmed, Munir; Akhtar, Mukhtar A.   
Pak. J. Sci. Ind. Res.  (1990),  33(10),  458-60. 
ISSN: 0030-9885.  Journal  written in English.
Abstract
Air oxidn. of RC6H4Me (R = H, 2-Cl, 4-Cl, 4-Me) in the presence of cobalt naphthenate as a catalyst gave 70-95% RC6H4CO2H.  

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tomjuan

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Re: Benzoic Acid via Toluene
« Reply #22 on: November 29, 2001, 11:32:00 AM »
This doesn't seem limited to toluene. This is basically a side-chain oxidation - wouldn't any phenyl-based molecule with an alpha C-H bond convert to benzoic acid via side-chain oxidation? Like aspartamine (nutra-sweet), for example, or even penicillin?

Also, H2O2 is much easier for many bees to come by, and reportedly has a higher oxidation potential than KMnO4. Could this be used instead?