Reactor design for the novozym 435-catalysed enantioselective esterification of 4-methyloctanic acid

N.W.J.T. Heinsman, P.L.J. van der Weide, A. van der Padt, M.C.R. Franssen, R.M. Boom, K. van 't Riet

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)

Abstract

The bench scale Novozym 435? catalysed esterification of 4-methyloctanoic acid with ethanol was studied at 35°C. Esterification in a batch reactor (molar ratio of 1:8 (acid:EtOH)) resulted in the isolation of the enantiomerically enriched product (eep=81 percent and substrate (ees=93 percent) In order to integrate reaction and separation, liquid-vapour equilibria calculations were performed showing that an excess of ethanol results in a very low ester fraction in the vapour phase. Since this is undesirable for an integrated process of reaction and product removal, a repeated batch reaction was performed using a molar ratio of 10:1 (acid:EtOH). After six cycles (45 percent conversion) the ee of 4-methyloctanoic acid ethyl ester turned out to be 80 percent. For different E values the eep was calculated for batch and repeated batch reactions. It was shown that in all cases the eep was higher for the repeated batch reaction. However, the product is not enantiopure since the E value of the reaction is rather low at the low ethanol concentration used. An alternative approach would be the continuous separation of the product during the reaction. A mathematical model was developed to describe esterification in a packed bed reactor integrated with product separation. This model shows that integration of reaction and product removal in advance is not suitable either to obtain an enantiomerically pure product. Since the optimal reaction conditions (high ethanol concentration) and the optimal separation system (low ethanol concentration) do not match in this reaction, the preference is given to the batch reaction at high ethanol concentrations because in that case the highest enantioselectivity of the enzyme is obtained.
LanguageEnglish
Pages429-436
JournalBiocatalysis and Biotransformation
Volume20
Issue number6
DOIs
Publication statusPublished - 2002

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Esterification
Ethanol
Acids
Esters
Enantioselectivity
Batch reactors
Packed beds
Phase equilibria
Novozyme 435
Theoretical Models
Enzymes
Vapors
Mathematical models
Substrates

Cite this

Heinsman, N.W.J.T. ; van der Weide, P.L.J. ; van der Padt, A. ; Franssen, M.C.R. ; Boom, R.M. ; van 't Riet, K. / Reactor design for the novozym 435-catalysed enantioselective esterification of 4-methyloctanic acid. In: Biocatalysis and Biotransformation. 2002 ; Vol. 20, No. 6. pp. 429-436.
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abstract = "The bench scale Novozym 435? catalysed esterification of 4-methyloctanoic acid with ethanol was studied at 35°C. Esterification in a batch reactor (molar ratio of 1:8 (acid:EtOH)) resulted in the isolation of the enantiomerically enriched product (eep=81 percent and substrate (ees=93 percent) In order to integrate reaction and separation, liquid-vapour equilibria calculations were performed showing that an excess of ethanol results in a very low ester fraction in the vapour phase. Since this is undesirable for an integrated process of reaction and product removal, a repeated batch reaction was performed using a molar ratio of 10:1 (acid:EtOH). After six cycles (45 percent conversion) the ee of 4-methyloctanoic acid ethyl ester turned out to be 80 percent. For different E values the eep was calculated for batch and repeated batch reactions. It was shown that in all cases the eep was higher for the repeated batch reaction. However, the product is not enantiopure since the E value of the reaction is rather low at the low ethanol concentration used. An alternative approach would be the continuous separation of the product during the reaction. A mathematical model was developed to describe esterification in a packed bed reactor integrated with product separation. This model shows that integration of reaction and product removal in advance is not suitable either to obtain an enantiomerically pure product. Since the optimal reaction conditions (high ethanol concentration) and the optimal separation system (low ethanol concentration) do not match in this reaction, the preference is given to the batch reaction at high ethanol concentrations because in that case the highest enantioselectivity of the enzyme is obtained.",
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Reactor design for the novozym 435-catalysed enantioselective esterification of 4-methyloctanic acid. / Heinsman, N.W.J.T.; van der Weide, P.L.J.; van der Padt, A.; Franssen, M.C.R.; Boom, R.M.; van 't Riet, K.

In: Biocatalysis and Biotransformation, Vol. 20, No. 6, 2002, p. 429-436.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Reactor design for the novozym 435-catalysed enantioselective esterification of 4-methyloctanic acid

AU - Heinsman, N.W.J.T.

AU - van der Weide, P.L.J.

AU - van der Padt, A.

AU - Franssen, M.C.R.

AU - Boom, R.M.

AU - van 't Riet, K.

PY - 2002

Y1 - 2002

N2 - The bench scale Novozym 435? catalysed esterification of 4-methyloctanoic acid with ethanol was studied at 35°C. Esterification in a batch reactor (molar ratio of 1:8 (acid:EtOH)) resulted in the isolation of the enantiomerically enriched product (eep=81 percent and substrate (ees=93 percent) In order to integrate reaction and separation, liquid-vapour equilibria calculations were performed showing that an excess of ethanol results in a very low ester fraction in the vapour phase. Since this is undesirable for an integrated process of reaction and product removal, a repeated batch reaction was performed using a molar ratio of 10:1 (acid:EtOH). After six cycles (45 percent conversion) the ee of 4-methyloctanoic acid ethyl ester turned out to be 80 percent. For different E values the eep was calculated for batch and repeated batch reactions. It was shown that in all cases the eep was higher for the repeated batch reaction. However, the product is not enantiopure since the E value of the reaction is rather low at the low ethanol concentration used. An alternative approach would be the continuous separation of the product during the reaction. A mathematical model was developed to describe esterification in a packed bed reactor integrated with product separation. This model shows that integration of reaction and product removal in advance is not suitable either to obtain an enantiomerically pure product. Since the optimal reaction conditions (high ethanol concentration) and the optimal separation system (low ethanol concentration) do not match in this reaction, the preference is given to the batch reaction at high ethanol concentrations because in that case the highest enantioselectivity of the enzyme is obtained.

AB - The bench scale Novozym 435? catalysed esterification of 4-methyloctanoic acid with ethanol was studied at 35°C. Esterification in a batch reactor (molar ratio of 1:8 (acid:EtOH)) resulted in the isolation of the enantiomerically enriched product (eep=81 percent and substrate (ees=93 percent) In order to integrate reaction and separation, liquid-vapour equilibria calculations were performed showing that an excess of ethanol results in a very low ester fraction in the vapour phase. Since this is undesirable for an integrated process of reaction and product removal, a repeated batch reaction was performed using a molar ratio of 10:1 (acid:EtOH). After six cycles (45 percent conversion) the ee of 4-methyloctanoic acid ethyl ester turned out to be 80 percent. For different E values the eep was calculated for batch and repeated batch reactions. It was shown that in all cases the eep was higher for the repeated batch reaction. However, the product is not enantiopure since the E value of the reaction is rather low at the low ethanol concentration used. An alternative approach would be the continuous separation of the product during the reaction. A mathematical model was developed to describe esterification in a packed bed reactor integrated with product separation. This model shows that integration of reaction and product removal in advance is not suitable either to obtain an enantiomerically pure product. Since the optimal reaction conditions (high ethanol concentration) and the optimal separation system (low ethanol concentration) do not match in this reaction, the preference is given to the batch reaction at high ethanol concentrations because in that case the highest enantioselectivity of the enzyme is obtained.

U2 - 10.1080/1024242021000040864

DO - 10.1080/1024242021000040864

M3 - Article

VL - 20

SP - 429

EP - 436

JO - Biocatalysis and Biotransformation

T2 - Biocatalysis and Biotransformation

JF - Biocatalysis and Biotransformation

SN - 1024-2422

IS - 6

ER -