Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy
Investigation involving enantioselective synthesis of chiral compounds catalysed by immobilised enzyme lipase is a viable option. In this study, acetic anhydride as an acylating agent was employed with (±)-menthol, a secondary alcohol in enantioselective synthesis of (-)-menthyl acetate in a fed ba...
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Faculty of Chemical and Natural Resources Engineering, UTM
2001
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my.utm.50702010-06-01T03:23:14Z http://eprints.utm.my/id/eprint/5070/ Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy Sarmidi, Mohamad Roji Lim, Jinny Lay Poh Ng, Tit Soo T Technology (General) Investigation involving enantioselective synthesis of chiral compounds catalysed by immobilised enzyme lipase is a viable option. In this study, acetic anhydride as an acylating agent was employed with (±)-menthol, a secondary alcohol in enantioselective synthesis of (-)-menthyl acetate in a fed batch reactor. (-)-menthyl acetate is an optically active flavour and fragrance compound. Molar ratio concentration of acetic anhydride to (±)-menthol is 1:4. The ratio of alcohol to acyl donor, acid anhydride to (±)-menthol was prepared at 15 mmole/L : 60 mmole/L in 25 ml n-heptane. The reaction was catalysed by commercially available immobilised enzyme lipase, chirazymeL-3, c. -f, C2 lyo from candida rugosa. The incorporation of a fed batch feeding system to the batch reactor configuration was investigated. The system was evaluated in terms of molar percentage yield and productivity. The reactions were carried out at 30°C in n-heptane and molar yield as high as 8.72% -29.57% were attained after 48 hours of reaction. This fed batch feeding system was thought able to minimise the hydrolysis of acetic anhydride. A high concentration of acetic anhydride in a batch reaction system is not a viable option since water present in the reaction mixture would promote the hydrolysis of acetic anhydride catalysed by the same enzyme. A fed batch feeding strategy of 12uL, 10uL, 8uL and 6uL produced the highest molar percentage yield with 29.57% of (-)-menthyl acetate formation and productivity of 0.00154mM/min. The enzyme loading used was only 40% from the actual equivalent amount. Faculty of Chemical and Natural Resources Engineering, UTM 2001 Article PeerReviewed application/pdf en http://eprints.utm.my/id/eprint/5070/1/MohamadRojiSarmidi2001_EnantioselectiveSynthesisOf%28-%29-MenthylAcetate.pdf Sarmidi, Mohamad Roji and Lim, Jinny Lay Poh and Ng, Tit Soo (2001) Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy. Proceedings of The 15th Symposium of Malaysian Chemical Engineers SOMChE 2001 . pp. 472-476. |
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T Technology (General) Sarmidi, Mohamad Roji Lim, Jinny Lay Poh Ng, Tit Soo Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| description |
Investigation involving enantioselective synthesis of chiral compounds catalysed by immobilised enzyme lipase is a viable option. In this study, acetic anhydride as an acylating agent was employed with (±)-menthol, a secondary alcohol in enantioselective synthesis of (-)-menthyl acetate in a fed batch reactor. (-)-menthyl acetate is an optically active flavour and fragrance compound. Molar ratio concentration of acetic anhydride to (±)-menthol is 1:4. The ratio of alcohol to acyl donor, acid anhydride to (±)-menthol was prepared at 15 mmole/L : 60 mmole/L in 25 ml n-heptane. The reaction was catalysed by commercially available immobilised enzyme lipase, chirazymeL-3, c. -f, C2 lyo from candida rugosa. The incorporation of a fed batch feeding system to the batch reactor configuration was investigated. The system was evaluated in terms of molar percentage yield and productivity. The reactions were carried out at 30°C in n-heptane and molar yield as high as 8.72% -29.57% were attained after 48 hours of reaction. This fed batch feeding system was thought able to minimise the hydrolysis of acetic anhydride. A high concentration of acetic anhydride in a batch reaction system is not a viable option since water present in the reaction mixture would promote the hydrolysis of acetic anhydride catalysed by the same enzyme. A fed batch feeding strategy of 12uL, 10uL, 8uL and 6uL produced the highest molar percentage yield with 29.57% of (-)-menthyl acetate formation and productivity of 0.00154mM/min. The enzyme loading used was only 40% from the actual equivalent amount. |
| format |
Article |
| author |
Sarmidi, Mohamad Roji Lim, Jinny Lay Poh Ng, Tit Soo |
| author_facet |
Sarmidi, Mohamad Roji Lim, Jinny Lay Poh Ng, Tit Soo |
| author_sort |
Sarmidi, Mohamad Roji |
| title |
Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| title_short |
Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| title_full |
Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| title_fullStr |
Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| title_full_unstemmed |
Enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| title_sort |
enantioselective synthesis of (-)-menthyl acetate in a batch stirred tank reactor: effects of fed batch feeding strategy |
| publisher |
Faculty of Chemical and Natural Resources Engineering, UTM |
| publishDate |
2001 |
| url |
http://eprints.utm.my/id/eprint/5070/1/MohamadRojiSarmidi2001_EnantioselectiveSynthesisOf%28-%29-MenthylAcetate.pdf http://eprints.utm.my/id/eprint/5070/ |
| _version_ |
1643644228253777920 |
| score |
13.251813 |