Dimethyl-p-toluidine

The basic patent (US Patent 3256219) indicates that the system is viable with conventional resins although special grades have been developed that are said to be particularly suitable. One example in the patent recommends the use of a polyester prepared using a maleic acid, phthalic acid and propylene glycol ratio of 2 1 33 and with an acid value of 40. To 500g of such a resin are added 10g of benzoyl peroxide and 167 g of styrene. Water 600 g is then stirred in at 5-10°C until a white creamy water-in-oil emulsion is obtained. A solution of 0.8 g of dimethyl-p-toluidine in lOOg of styrene is stirred into the emulsion and the resin is cast between plates and cured at 50°C. 

Dimethyl-4-heptanone (diisobutyl ketone) Dimethyl sulphate N,N-Dimethyl-p-toluidine Dimethylamine... 

The acylation of dienamines has not been extensively investigated. The dienamine (127) prepared by Birch reduction of N,N-dimethyl-p-toluidine has been shown to react with diketene (90) to give the chromone (128), showing that attack occurs at the /9-carbon of the dienamine system. 

This latter, when heated at 150° to 160° C. with dimethyl-p-toluidine is decomposed with the production of vanillin. 

Organic peroxide-aromatic tertiary amine system is a well-known organic redox system 1]. The typical examples are benzoyl peroxide(BPO)-N,N-dimethylani-line(DMA) and BPO-DMT(N,N-dimethyl-p-toluidine) systems. The binary initiation system has been used in vinyl polymerization in dental acrylic resins and composite resins [2] and in bone cement [3]. Many papers have reported the initiation reaction of these systems for several decades, but the initiation mechanism is still not unified and in controversy [4,5]. Another kind of organic redox system consists of organic hydroperoxide and an aromatic tertiary amine system such as cumene hydroperoxide(CHP)-DMT is used in anaerobic adhesives [6]. Much less attention has been paid to this redox system and its initiation mechanism. A water-soluble peroxide such as persulfate and amine systems have been used in industrial aqueous solution and emulsion polymerization [7-10], yet the initiation mechanism has not been proposed in detail until recently [5]. In order to clarify the structural effect of peroxides and amines including functional monomers containing an amino group, a polymerizable amine, on the redox-initiated polymerization of vinyl monomers and its initiation mechanism, a series of studies have been carried out in our laboratory. 

Dimethylphenol lb 149 Dimelhylphenols lb 148,149 N,N-Dimethyl-p-toluidine lb 268 Dimethyl sulfoxide as intrinsic detector... 

A drop of amine added to benzoyl peroxide is enough to cause a deflagration or a detonation of the peroxide, depending on to what extent the apparatus is confined. Phenylamine, N,N-dimethylaniline, N,N-dimethyl-p-toluidine react the same way. 

Matsson and co-workers (Axelsson et al., 1987) measured the carbon-ll/carbon-14 a-carbon KIEs for the Menshutkin reaction between N,N-dimethyl-p-toluidine and labelled methyl iodide in methanol at 30°C. The 1 -labelled methyl iodide required for this study was prepared in three steps [reaction (23)] from the "C atoms produced in a cyclotron (L ngstrom etal., 1987). 

The bone cement used in these studies was a two-component system. The liquid component [9.75 mL methyl methacrylate (MMA) 0.25 mL A,A-dimethyl-p-toluidine (DMPT) 75 mg/kg hydroquinone] was mixed with a solid component [3.0 g poly(methyl methacrylate) (PMMA) 15.0 g MMA-styrene copolymer benzoyl peroxide, mass fraction 2% 2.0 g BaSOJ to form the cement. Dissolution of the solid component proceeded simultaneously with polymerization once the cement was mixed. 

Dimerization of arylamine cation-radicals is a prominent example of the product s steric hindrance effects on the reaction course. Although stable in AN, the A,A-dimethyl-p-toluidine dimerizes if its uncharged counterpart is present in the solution (Goto et al. 2002, Oyama and Goto 2003). The cation-radical loses a proton, and the parent amine reacts as a base, accepting this proton. Coupling of benzylic radicals is an understandable result of the following reaction ... 

N, N Dimetbyl-3,5 dinitro-p-toluidine, scarlet-red ndls (from petr eth) or prisms (from acet ac), mp 95° si sol in cold ale petr eth otherwise readily sol in org solvs was prepd by nitrating dimethyl-p-toluidine with 30% nitric acid dil sulfuric acid solns (Ref 2, pplOlO 442)... 

Enamines also react with diketene to form chromones (60JCS26). One drawback to this method is the use of 2,3-dihydro-Ar,Ar-dimethyl-p-toluidine, prepared by Birch reduction of the aromatic amine, and the consequent need to aromatize the reduced chromone which is the initial product. 

Commercial N,N-dimethyl-p-toluidine, obtained from Aldrich Chemical Company, Inc., was used without purification. 

This simple steam distillation removes the unchanged N,N-dimethyl-p-toluidine present in the crude product. 

This procedure is an adaptation of one described by Hauser and co-workers.4 The product has also been prepared from 2-bromo-N,N-dimethyl-p-toluidine by halogen-metal interchange with n-butyllithium followed by condensation with benzophenone,4 a procedure that is less convenient than that presently described. 

It is noteworthy that metallation of N,N-dimethyl-p-toluidine takes place at the position ortho to the dimethylamino group rather than on or ortho to the aryl methyl group. Appar-... 

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