Synthesis of 5-Acetoxymethyl- and 5-Hydroxymethyl-2-vinyl-furan

The total amount of cellulose from paper, wood, food, and other human activity waste produced in the EU is in the order of 900 million tons per year. This resource represents a sizable opportunity to produce renewable chemicals and energy. This paper reports, unprecedently in the literature, the usage of four different urban wastes such as cigarette butts, sanitary pant diapers, newspapers, and soybean peels as cellulose fonts to produce valuable industrial intermediates such as levulinic acid (LA), 5-acetoxymethyl-2-furaldehyde (AMF), 5-(hydroxymethyl)furfural (HMF), and furfural. The process is accomplished by the hydrothermal treatment of cellulosic waste using both Brønsted and Lewis acid catalysts such as CH3COOH (2.5–5.7 M), H3PO4 (15%), and Sc(OTf)3 (20% w:w), thus obtaining HMF (22%), AMF (38%), LA (25–46%), and furfural (22%) with good selectivity and under relatively mild conditions (T = 200 °C, time = 2 h). These final products can be employed in several chemical sectors, for example, as solvents, fuels, and for new materials as a monomer precursor. The characterization of matrices was accomplished by FTIR and LCSM analyses, demonstrating the influence of morphology on reactivity. The low e-factor values and the easy scale up render this protocol suitable for industrial applications.

show abstract

“…AMF (5-Acetoxymethyl-2-furaldehyde): Ref. [ 23 ] colorless oil, GC/MS (70 eV) m / z (rel. intensity).…”

Section: Methodsmentioning

confidence: 99%

Eco-Friendly Catalytic Synthesis of Top Value Chemicals from Valorization of Cellulose Waste

et al. 2023

View full text Add to dashboard Cite

show abstract

“…HMVF also exhibits cell adhesion property. 41 Hence, the derivatives of HMF obtained through various reactions are crucial for medicines, food industries, pesticides, and other fields.…”

Section: Production and Chemistry Of Hmfmentioning

confidence: 99%

Recent advances in biotransformation of 5‐Hydroxymethylfurfural: challenges and future aspects

Saikia

Rathankumar

Kumar

et al. 2021

J of Chemical Tech & Biotech

View full text Add to dashboard Cite

In a biorefinery process, 5-Hydroxymethylfurfural (HMF) is a promising biomass-derived chemical with diverse industrial applications. The biotransformation of HMF to different high-valued furanic derivatives, such as 2,5-furandicarboxylic acid, 2,5-diformylfuran, 5-hydroxymethyl-2-furancarboxylic acid, and 5-formyl-2-furancarboxylic acid, has led to the transition from fossil-derived products to bio-based chemicals through sustainable routes. Although, chemocatalytic conversion of HMF has been extensively studied in the recent years, the higher selectivity, environment friendliness, and mild reaction conditions of HMF bioconversion has established these processes as a promising alternative to harsh chemical conditions. To understand the present status and challenges of HMF bioconversion, this review retrospects and describes the recent advancements in the biotransformation of HMF and systematically assesses the recent findings and developments in the HMF biotransformation through various reaction schemes. Further, this review illustrates, in comprehensive detail, the merits and challenges of various biological processes and it proposes a few research trends for economical and facile HMF bioconversion for commercialization.

show abstract

“…First, 6 was protected by acetylation to give furfuryl acetate (7) [4], which was subjected to Vilsmeier formylation to yield 5-(formyl)furfuryl acetate (8) [5]. Then, 3 was obtained by deacetylation [6].…”

Section: Scheme 2 Synthesis Of 5-hydroxypyrrolidin-2-one (2)mentioning

confidence: 99%

The First Synthesis of Sessiline

Ilkei¹,

Faragó²,

Sánta³

et al. 2014

IJOC

View full text Add to dashboard Cite

Sessiline is an alkaloid which was recently isolated from the fruits of Acanthopanax sessiliflorus. The molecule contains two five-membered heterocyclic units joined together by an acylaminocarbinol-ether type bond. Here, we describe the first, simple synthesis of sessiline from 5-hydroxypyrrolidin-2-one and 5-hydroxymethylfurfural, which are prepared from succinimide and furfuryl alcohol, respectively. The coupling reaction takes place on moderate heating under neat conditions.

show abstract

Synthesis of 5-Acetoxymethyl- and 5-Hydroxymethyl-2-vinyl-furan

Cited by 14 publications

References 10 publications

Eco-Friendly Catalytic Synthesis of Top Value Chemicals from Valorization of Cellulose Waste

Eco-Friendly Catalytic Synthesis of Top Value Chemicals from Valorization of Cellulose Waste

Recent advances in biotransformation of 5‐Hydroxymethylfurfural: challenges and future aspects

The First Synthesis of Sessiline

Contact Info

Product

Resources

About