Dissertation
Dissertation > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Vitamin manufacturing > Vitamin C

Synthesis of Ascorbyl Flurbiprofenate and the Technical Study of Its Green Production

Author WangZe
Tutor TangLuHong
School Jiangnan University
Course Microbial and Biochemical Pharmacy
Keywords Green Technology L-ascorbyl flurbiprofenate stabilization of VC Ascorbic acid triple-phosphate
CLC TQ466.3
Type Master's thesis
Year 2011
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Ascorbic acid is also called as Vitamin C,VC. which is a 2,3,5,6 4-hydroxy -2 - cyclohexyl acid - lactone, with a hydroxyl group in each carbon atom of the carbon-carbon double bond. VC can not only promote the synthesis of collagen, but also Participate in a variety of hydroxylation reactions in vivo. VC have the effect of oxidation resistance and anti-freeradical as an reducing agent. Since VC was synthesized successfully by Reichestein from Switzerland in 1934, the VC-producing grows very fast. So the derivatives of VC are also being developed continuously.There are two main types of VC-derivatives. One group contains the VC fatty acid esters which are made up for improving bad fat-soluble of VC. They used in the domain of Food additives as antioxidant。The other group contains the stability VC-derivatives for its instabilization. They are used to be used in the domain of feed additives as stability nutrient content. In addition, SVCT1 and SVCT2 which is the transporters of VC have the ability that it takes VC into the central nervous system. So VC was also tried to make up to pro-drugs with the drug which has carboxyl and act on the central nervous system.A new chemical entity, L-ascorbyl flurbiprofenate (L-AF), the L-ascorbic acid ester of Flurbiprofen, has been synthesized successfully from Flurbiprofen and L-ascorbic acid in Tert-amyl alcohol catalyzed by lipase. After separation and purification, the product has been crystallized. HPLC-MS showed that the purity was higher than 95% and which fit to the molecular mass of L-AF(402). The spectrums of UV, IR, H1 NMR and C13 NMR further confirmed the structure. Meanwhile, a number of physical and chemical parameters were determined.We have studied the stability derivatives of VC: Ascorbate and ascorbyl-2-triple-phosphate which is the most outstanding product in all aspects at present.We modified the process parameters of ascorbic acid 3-phosphate and made the process steps optimized. We used the VC-solution which is the waste of process of VC fatty esters and L-ascorbyl profenate process as subtract. We not only reduce the waste, but also achieve the lower cost,higher added value.

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