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

Öz

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 mg/mL 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.

Anahtar Kelimeler

• Green solvent
• dimethyl carbonate
• 1-phenylethanol
• kinetic resolution
• Novozyme 435

Yeşil Çözücü Ortamında Enzimatik Kinetik Rezolüsyon Yöntemi ile Enantiyomerik Saflıkta 1-Feniletanol Üretimi

Öz

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 mg/mL lipaz derişimlerinde, 40℃ ve 250 rpm’de 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 DMK’nın 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.

Anahtar Kelimeler

• Yeşil çözücü
• dimetil karbonat
• 1-feniletanol
• kinetik rezolüsyon
• Novozyme 435

Kaynakça

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