The Synthesis Of Three Kinds Of Vitamin E Esters And Their Preliminary Application In Cigarette

Research shows smokers often have low levels of vitamin E and confirmed levels of vitamin E of smokers were 30 percent below the levels of vitamin E of non-smokers. A lack of vitamin E may causes many kinds of diseases, so smokers should supplement vitamin E. Focusing on developing a low hazard cigarette with containing plenty of vitamin E in mainstream cigarette smoke and reducing consumption of vitamin E of smokers, this paper mainly does the following researches:1. A method was developed for the quantization of vitamin E in cigarette and cigarette mainstream smoke wet total particulate matter (WTPM) collected on a Cambridge filter. Vitamin E in tobacco, cigarette and cigarette mainstream smoke wet total particulate matter (WTPM) were detected by this method. The results indicated that:Vitamin E belongs to trace substance, which is about one in one thousand in flue-cured tobacco and below five-ten thousandths in sun-cured tobacco, burley tobacco and oriental tobacco;The percent transfer of vitamin E from tobacco to mainstream smoke are about 8-16%(flue-cured type cigarette),1-12%(blended type cigarette).2. Vitamin E is oxidize easily,which limits it's added directly into cigarette to a great extent. Inspired by the application of vitamin E in medicine, cosmetics, etc, we transform vitamin E into the form of its esters added in cigarette. Using triethylamine and DCC as the catalyst, Vitamin E acetate, vitamin E succinate and vitamin E nicotinate were synthesized from acetic anhydride, succinic anhydride, nicotinic acid and vitamin E, Whose structure are identified by 1H-NMR,13C-NMR spectroscopy and GC-MS.3. For investigating their application effect in cigarette, Vitamin E esters of different concentration gradients were added to cigarettes by the spice injector. Vitamin E and TSNAs in mainstream cigarette smoke were systematically analyzed, and cigarettes quality were evaluated by the sense of evaluating experts. The results indicated that:Vitamin E esters have the better stability than Vitamin E, Vitamin E in mainstream cigarettes with Vitamin E esters smoke WTPM was increased; With the same addition, the Vitamin E mainstream cigarettes with vitamin E succinate smoke WTPM was higher than that with vitamin E nicatinate and vitamin E acetate;Vitamin E succinate could restrain the TSNAs in cigarette mainstream smoke; The sensory evaluation showed that the vitamin E succinate imparted a characteristic flavor to the smoke of cigarette, under the condition of 2mg/cig have the best quality.4.A cigarette additive could't be evaluated fully and accurately only from the chemical components in mainstream smoke of cigarettes, due to the complexity of the combustion of cigarette.The pyrolysis behavior of vitamin E succinate was investigated by on-line pyrolysis-gas chromatography-mass spectrometry (Py/GC-MS) in the presence of helium. This study provide theoretical evidence for the application of vitamin E succinate as a cigarette additive from the viewpoint of molecule. GC-MS was used for the qualitative and semi-quantitative analysis of the pyrolysis products of vitamin E succinate at 450,600,750 and 900℃.72 pyrolysis products were detected, including vitamin E, cinnamic aldehyde, benzenepropanal. The results indicated that:flavorous substances, such as Cinnamic aldehyde and Benzenepropanal, were released from parent compound under 450-750℃. However, above 750℃, flavor was not found in the pyrolysis products. With the raise of pyrolysis temperature, complicated pyrolysis products appeared, and the content of harmful substances, such as anthracene, phenanthren and Fluorene, were also increased. According to the relative content and category of the pyrolysis products, the possible pyrolysis mechanism of Vitamin E succinate was also discussed.