Study On The Preparation Of Veratraldehyde And Its Derivatives

Perfume is a kind of substance that can be perceived by human sense of smell or taste.It plays an important role in many aspects of human life,such as additives for cosmetics,food,medicines,etc.Among of widely used fragrances,aromatic aldehydes possess splendid features containing actively chemical property,and pleasant and strong aroma,which have become the research interests in chemical industry as well aslaboratory investigation.For example,3,4-dimethoxybenzaldehyde(cucurbitaldehyde)is the representative compound.And it can be used not only as a fragrance alone,but also as an important intermediate for the synthesis of compounds such as vanillin,isopenillin,resveratrol and cucurbitac.An experimental route was confirmed by consulting relevant literatures for the preparation of N-methylformanilide using N-methylaniline and formic acid.The obtained N-methylformanilide can sequentially react with phthalic acid to produce veratraldehyde.Accordingly,the reaction conditions are optimized,such as molar ratio of reaction materials,reaction time,reaction temperature.Under the optimized reactive conditions,the yield of N-methylformanilide and cucurbitaldehyde can reach to 96.32% and 88.56%,respectively.Furthermore,the purity of products were characterized by high performance liquid chromatography.We also characterized the structure of the products by infrared spectroscopy and nuclear magnetic resonance spectroscopy.As we all know,Vanillin,iso-vanillin,resveratrol and cucurbitacic acid are the main derivatives of veratraldehyde.We also determined the synthetic route for the synthesis of vanillin,iso-vanillin,resveratrol and cucurbitacin using ascorbic aldehyde as a starting material.The reaction conditions are optimized,such as molar ratio of reaction materials,reaction time,reaction temperature.Under the optimal reaction conditions,the yield of vanillin was 89.54%,the yield of iso-vanillin was 88.73%,the yield of cucurbit acid was 95.46%,and the yield of resveratrol was 93.85%.The purity of the reaction product was characterized by high performance liquid chromatography,and the structure of the product was characterized by infrared spectroscopy and nuclear magnetic resonance spectroscopy.On the basis of the laboratory's small test,the synthesis of 3,4-dimethoxybenzaldehyde was scaled up.Finally,we carried out the industrial design by the physical properties of the reactants,material balance and heat balance calculation,combined with industry standards.In addition,The model and material selection,as well as technological parameters of production equipmentswere optimized.