Organocatalytic Upgrading of Furfural and 5-Hydroxymethyl Furfural to C10 and C12 Furoins with Quantitative Yield and Atom-Efficiency
نویسندگان
چکیده
There is increasing interest in the upgrading of C5 furfural (FF) and C6 5-hydroxymethyl furfural (HMF) into C10 and C12 furoins as higher energy-density intermediates for renewable chemicals, materials, and biofuels. This work utilizes the organocatalytic approach, using the in situ generated N,S-heterocyclic carbene catalyst derived from thiazolium ionic liquids (ILs), to achieve highly efficient self-coupling reactions of FF and HMF. Specifically, variations of the thiazolium IL structure have led to the most active and efficient catalyst system of the current series, which is derived from a new thiazolium IL carrying the electron-donating acetate group at the 5-ring position. For FF coupling by this IL (0.1 mol %, 60 °C, 1 h), when combined with Et3N, furoin was obtained in >99% yield. A 97% yield of the C12 furoin was also achieved from the HMF coupling by this catalyst system (10 mol % loading, 120 °C, 3 h). On the other hand, the thiazolium IL bearing the electron-withdrawing group at the 5-ring position is the least active and efficient catalyst. The mechanistic aspects of the coupling reaction by the thiazolium catalyst system have also been examined and a mechanism has been proposed.
منابع مشابه
Application and Optimization of Dispersive Liquid-liquid Microextraction Coupled with High-performance Liquid Chromatography for Sensitive Determination of Furfural and Hydroxymethyl Furfural in Jarred and Canned Baby-foods
Background and Objectives: Furfural (F) and hydroxymethyl furfural (HMF) are cyclic aldehydes, which are formed during the heat processing of foods. These chemical contaminants have received much attention due to their suspected health hazards and heat damage indicators. The aim of the present study was extraction and determination of F and HMF in baby-foods using dispersive liquid-liquid micro...
متن کاملIdentification and Quantification of 5-Hydroxymethyl Furfural in Food Products
5-Hydroxymethylfurfural (5-HMF) is known as an indicator of quality deterioration in a wide range of foods. The current study covered 70 samples taken from domestically produced foods and drinks available on the Iranian markets (including honey, jam, fruit cakes tomato paste, ketchup, syrup, fruit juice, canned fruit, UHT milk, instant coffee and jelly powder). HMF levels were determined using ...
متن کاملDetermination of Acrylamide and 5-hydroxymethyl-2-furfural (HMF) Levels and Related Parameters in Turkish Pekmez (A Traditional Fruit Product)
Background: Pekmez is an important fruit-based food of Turkish culinary culture. The aim of this study is to determine the levels of acrylamide (AA), 5-hydroxymethyl-2-furfural (HMF) and other selected parameters in grape, mulberry and carob Pekmez. Methods: AA and HMF were analyzed by Liquid Chromatography and High Performance Liquid Chromatography, respectively. Also, glucose, fructose, pH, ...
متن کاملIdentification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14.
The toxic fermentation inhibitors in lignocellulosic hydrolysates pose significant problems for the production of second-generation biofuels and biochemicals. Among these inhibitors, 5-(hydroxymethyl)furfural (HMF) and furfural are specifically notorious. In this study, we describe the complete molecular identification and characterization of the pathway by which Cupriavidus basilensis HMF14 me...
متن کاملبررسی و مقایسه حذف فورفورال از فاضلاب توسط راکتور بیولوژیکی سیکلی (CBR) و گرانولهای قارچ فوزاریوم کولموروم
Background and Objectives: Furfural with a chemical formula of C5H4O2 is a toxic and hazardous substance for human and environment. Furfural and its derivatives such as furfuryl alcohol, alone or in combination with phenol, acetone or urea are used mainly in the production of resin. The second major application of furfural is in the production of solvents such furan and tetrafuran frequently us...
متن کامل