The Production of Enantiomerically Pure 1-Phenylethanol in Green Solvent Media via Enzymatic Kinetic Resolution Method

Ayşe Bozan; Rahime Songür; Ülkü Mehmetoğlu

Makale detayları

The Production of Enantiomerically Pure 1-Phenylethanol in Green Solvent Media via Enzymatic Kinetic Resolution Method

Yazarlar:

Ayşe Bozan | Rahime Songür | Ülkü Mehmetoğlu

Yayıncı:

Gazi University

Ana Başlıklar:

Mühendislik

Dergi:

Politeknik Dergisi Vol.27 Issue 4, pp.1213-1222

Belge Tipi:

Makale

Yayın Tarihi:

9/2024

Belge Dili:

Türkçe

Document ID (Org No.):

2001327706

pISSN:

2147-9429

Anahtar kelimeler:

Özet:

 Solvents are among the most critical components in chemical processes. For this reason, in addition to its important properties such as structure, cost and availability, a solvent must be also safe and environmentally friendly. Therefore, the research on the use of green solvents to replace the traditional ones have gained wide interest.1-phenylethanol is one of the important chiral building blocks which are used for producing fine chemicals in several industries. In this work, it was aimed to produce enantiomerically pure 1-phenylethanol in the green solvent media. Accordingly, propylene carbonate PC, dimethyl carbonate DMC and 2-methyltetrahydrofuran MeTHF were used. Best results were obtained by using DMC. 100 enantiomeric excess for the substrate ees and 50 conversion were reached with 240 mM substrate concentration, 20 mgmL lipase concentration and 3 hours reaction time at 40 and 250 rpm. In this work; DMC, which is characterized as one of the greenest solvents, was used as the reaction solvent for the first time in the enzymatic kinetic resolution of racemic 1-phenylethanol. When compared with the literature, in which both traditional and other green solvents were used, it was observed that DMC can replace these solvents, considering its advantageous properties such as low eco-toxicity, high biodegrability and low cost, together with its high ees and conversion values.

 Solvents are among the most critical components in chemical processes. For this reason, in addition to its important properties such as structure, cost and availability, a solvent must be also safe and environmentally friendly. Therefore, the research on the use of green solvents to replace the traditional ones have gained wide interest.1-phenylethanol is one of the important chiral building blocks which are used for producing fine chemicals in several industries. In this work, it was aimed to produce enantiomerically pure 1-phenylethanol in the green solvent media. Accordingly, propylene carbonate PC, dimethyl carbonate DMC and 2-methyltetrahydrofuran MeTHF were used. Best results were obtained by using DMC. 100 enantiomeric excess for the substrate ees and 50 conversion were reached with 240 mM substrate concentration, 20 mgmL lipase concentration and 3 hours reaction time at 40 and 250 rpm. In this work; DMC, which is characterized as one of the greenest solvents, was used as the reaction solvent for the first time in the enzymatic kinetic resolution of racemic 1-phenylethanol. When compared with the literature, in which both traditional and other green solvents were used, it was observed that DMC can replace these solvents, considering its advantageous properties such as low eco-toxicity, high biodegrability and low cost, together with its high ees and conversion values.

 Solvents are among the most critical components in chemical processes. For this reason, in addition to its important properties such as structure, cost and availability, a solvent must be also safe and environmentally friendly. Therefore, the research on the use of green solvents to replace the traditional ones have gained wide interest.1-phenylethanol is one of the important chiral building blocks which are used for producing fine chemicals in several industries. In this work, it was aimed to produce enantiomerically pure 1-phenylethanol in the green solvent media. Accordingly, propylene carbonate PC, dimethyl carbonate DMC and 2-methyltetrahydrofuran MeTHF were used. Best results were obtained by using DMC. 100 enantiomeric excess for the substrate ees and 50 conversion were reached with 240 mM substrate concentration, 20 mgmL lipase concentration and 3 hours reaction time at 40 and 250 rpm. In this work; DMC, which is characterized as one of the greenest solvents, was used as the reaction solvent for the first time in the enzymatic kinetic resolution of racemic 1-phenylethanol. When compared with the literature, in which both traditional and other green solvents were used, it was observed that DMC can replace these solvents, considering its advantageous properties such as low eco-toxicity, high biodegrability and low cost, together with its high ees and conversion values.

 Çözücüler kimyasal proseslerdeki en kritik bileşenlerdendir. Bu yüzden çözücünün yapısı, maliyeti ve ulaşılabilir olması gibi önemli özelliklerinin yanı sıra güvenilir ve çevre dostu olması da gerekmektedir. Bu nedenle, son zamanlarda geleneksel çözücülerin yerini alabilecek yeşil çözücü arayışları hız kazanmıştır. Bu çalışmada değerli kimyasalların üretiminde önemli kiral yapı bloklarından olan 1-feniletanolün yeşil çözücü ortamında enantiyomerik saflıkta elde edilmesi amaçlanmış ve bu doğrultuda propilen karbonat PK, dimetil karbonat DMK ve 2-metiltetrahidrofuran MeTHF kullanılmıştır. En iyi sonuçlar DMK kullanıldığında sağlanmış olup 240 mM substrat ve 20 mgmL lipaz derişimlerinde, 40 ve 250 rpmde gerçekleştirilen 3 saat reaksiyon sonunda substrat için 100 enantiyomerik aşırılık ees ile 50 dönüşüme ulaşılmıştır. Bu çalışma ile en yeşil çözücülerden biri olarak nitelendirilen DMK ilk kez rasemik 1-feniletanolün enzimatik kinetik rezolüsyonunda çözücü ortamı olarak kullanılmıştır. Sonuçlar, literatürde hem geleneksel hem de diğer yeşil çözücülerle gerçekleştirilen çalışmalarla karşılaştırıldığında DMKnın düşük eko-toksikliği, biyo-bozunurluğu, düşük maliyetli olması gibi avantajlı özelliklerinin yanı sıra yüksek ees ve dönüşüm de sağlaması neticesinde bu çözücülerin yerine geçebileceğini göstermiştir.

Makale detayları

The Production of Enantiomerically Pure 1-Phenylethanol in Green Solvent Media via Enzymatic Kinetic Resolution Method

Yazarlar:

Ayşe Bozan | Rahime Songür | Ülkü Mehmetoğlu

Yayıncı:

Gazi University

Ana Başlıklar:

Mühendislik

Dergi:

Politeknik Dergisi Vol.27 Issue 4, pp.1213-1222

Belge Tipi:

Makale

Yayın Tarihi:

9/2024

Belge Dili:

Türkçe

Document ID (Org No.):

2001327706

pISSN:

2147-9429

Green solvent

dimethyl carbonate

1-phenylethanol

kinetic resolution

Novozyme 435Yeşil çözücü

dimetil karbonat

1-feniletanol

kinetik rezolüsyon

Novozyme 435

Sayı

Makale detayları

Yazarlar: Ayşe Bozan | Rahime Songür | Ülkü Mehmetoğlu

Yayıncı: Gazi University

Ana Başlıklar: Mühendislik

Dergi: Politeknik Dergisi Vol.27 Issue 4, pp.1213-1222

Belge Tipi: Makale

Yayın Tarihi: 9/2024

Belge Dili: Türkçe

Document ID (Org No.): 2001327706

pISSN: 2147-9429

Sayı

Yazarlar:

Ayşe Bozan | Rahime Songür | Ülkü Mehmetoğlu

Yayıncı:

Gazi University

Ana Başlıklar:

Mühendislik

Dergi:

Politeknik Dergisi Vol.27 Issue 4, pp.1213-1222

Belge Tipi:

Makale

Yayın Tarihi:

9/2024

Belge Dili:

Türkçe

Document ID (Org No.):

2001327706

pISSN:

2147-9429