4196-96-7

Upstream product

• 98-01-1 furfural 
• 108-10-1 4-methyl-2-pentanone 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 

Downstream Products

• 24383-84-4 1t-[2]furyl-5-methyl-hex-1-en-3-one-(2,4-dinitro-phenylhydrazone) 
• 871-83-0 isodecane 
• 6975-98-0 2-methyldecane 

Relevant academic research and scientific papers

Practical aqueous reactions leading to skeletally diverse carbohydrate-derived ketones

Four types of skeletally diverse compounds have been synthesized from protected aldosyl hemiacetals and methyl ketones using cheap catalysts in water in one pot. Among the four skeletons, two of them are not accessible by current methods. The reactions are operationally simple, high yielding and scalable, which opens a practical channel for utilizing carbohydrates to produce chemical and pharmaceutical intermediates and products.

Solvent-free synthesis of C10 and C11 branched alkanes from furfural and methyl isobutyl ketone

Our best results jet: C10 and C11 branched alkanes, with low freezing points, are synthesized through the aldol condensation of furfural and methyl isobutyl ketone from lignocellulose, which is then followed by hydrodeoxygenation. These jet-fuel-range alkanes are obtained in high overall yields (≈90 %) under solvent-free conditions. Copyright

Rational design of bifunctional hierarchical Pd/SAPO-5 for the synthesis of tetrahydrofuran derivatives from furfural

The one-pot aldol condensation/crotonization reaction between furfural and methyl isobutyl ketone (MIBK), followed by hydrogenation with molecular H2, was implemented for preparing tetrahydrofuran derivatives. To this aim, we developed a robust Pd/HPSAPO-5 catalyst based on the crystalline silico-aluminophosphate SAPO-5 with hierarchical porosity and optimized silicon content. The hierarchical HPSAPO-5 catalyst was synthesized using a bottom-up method starting from pre-synthesized MCM-41, with the surfactant (CTAB) inside the mesopores, serving both as Si source and mesoporogen. NH3-TPD and FT-IR spectroscopy of adsorbed probe molecules combined with solid-state 1H MAS NMR were used to assess the nature, strength and accessibility of the acid sites. The structural and textural properties of the catalysts were investigated using X-ray diffraction (XRD) and N2 adsorption. HR-TEM was used to assess the dispersion and location of Pd nanoparticles on HPSAPO-5. The spent catalyst could be restored and reused after calcination.

One-step Pd/C and Eu(OTf)3 catalyzed hydrodeoxygenation of branched C11 and C12 biomass-based furans to the corresponding alkanes

Solvent-free NaOH catalyzed aldol condensation of biomass-derived 5-hydroxymethyl furfural (HMF) and furfural with methyl isobutyl ketone (MIBK) was studied, producing branched C11and C12furan compounds in high yields of up to 96%. Through use of a Pd/C and Eu(OTf)3catalytic system, the condensation products of the bio-based starting materials were further hydrodeoxygenated (HDO) in one-step to biofuel compatible branched alkanes 2-methylundecane (3) and 2-methyldecane (4) in excellent yields of 90% and 98%, respectively. In the one-step HDO developed herein, the variation of solvent had a significant effect on the reaction route and degree of conversion of furans to alkanes in the HDO process. Very high overall yields of alkanes 3 (86%) and 4 (94%) were obtained starting from the biomass-based HMF and furfural.

Direct Catalytic Conversion of Furfural to Furan-derived Amines in the Presence of Ru-based Catalyst

The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan-derived amines was developed [e.g., 1-(furan-2-yl)-4-methylpentan-2-amine] with high yield (up to 95 %) from (E)-1-(furan-2-yl)-5-methylhex-1-en-3-one. The catalyst used was Ru/C, and it was recyclable up to the fourth cycle. To further realize cost-efficiency, a one-reactor tandem concept was attempted. To this aim direct reaction from furfural was investigated. A high yield (74 %) towards 1-(furan-2-yl)-4-methylpentan-2-amine could be achieved starting directly from furfural in the presence of methyl isobutyl ketone, NH3, H2, and Ru/C catalyst.

PROCESS FOR THE REDUCTIVE AMINATION OF A CARBONYL COMPOUND

The invention relates to a process for the reductive amination of a carbonyl compound. The invention furthermore relates to a process for the preparation of a furan-derived amine starting from furfural or a derivative thereof.

PROCESS FOR REDUCTIVE AMINATION OF α,β-UNSATURATED CARBONYL COMPOUND

A process for the reductive amination of an α,β-unsaturated carbonyl compound and a process for the preparation of a tetrathydrofuran-derived amine starting from furfural or a derivative thereof.

PROCESS FOR REDUCTIVE AMINATION OF α, β-UNSATURATED KETONE

A process for reductive amination of α,β-unsaturated ketone is disclosed. A process for preparation of furan-derived amine starting from furfural or derivative thereof is also disclosed. The process is conducted in the presence of supported Ru as catalyst, the support of the supported Ru is selected from ceramics and carbon and preferably from Al 2O 3 and C.

Total hydrogenation of bio-derived furans over supported Ru subnanoclusters prepared via amino acid-assisted deposition

Development of a highly efficient and robust catalyst with reduced usage of noble metals is extremely desirable for selective hydrogenations of furan-containing bio-based feedstocks, which represents an attractive and sustainable alternative to petrochemical resources. Herein, we describe a new type of well-dispersed Ru subnanoclusters (ca. 0.50 wt%) supported on commercial P25 TiO2 material obtained from a facile and effective amino acid-assisted deposition-precipitation strategy. The as-synthesized catalyst exhibits superior catalytic activity and selectivity for direct hydrogenation of industrially important furfural as well as a range of structurally diverse bio-based furanic compounds to their corresponding fully hydrogenated derivatives. An average turnover frequency (ATOF) value as high as 367 h-1 at 80 °C and 4 MPa H2 is obtained, which is the highest reported value. This catalyst also shows stable furfural total hydrogenation in 5 reaction cycles conducted at 80 °C (52 mmol-scale, turnover number up to 12?500). In terms of the kinetic and structural characterizations, the key performances of the ultrasmall Ru clusters are proposed to mainly originate from an enhanced number of unsaturated surface Ru atoms and change in local coordination environment. Our work highlights the importance of the subnanometric size of Ru clusters in the advancement of efficient and affordable approaches towards bio-based chemical production.

Highly efficient Nb2O5 catalyst for aldol condensation of biomass-derived carbonyl molecules to fuel precursors

Aldol condensation is of significant importance for the production of fuel precursors from biomass-derived chemicals and has received increasing attention. Here we report a Nb2O5 catalyst with excellent activity and stability in the aldol condensation of biomass-derived carbonyl molecules. It is found that in the aldol condensation of furfural with 4-heptanone, Nb2O5 has obviously superior activity, which is not only better than that of other common solid acid catalysts (ZrO2 and Al2O3), more importantly, but also better than that of solid base catalysts (MgO, CaO, and magnesium-aluminum hydrotalcite). The detailed characterizations by N2 sorption/desorption, NH3-TPD, Py-FTIR and DRIFTS study of acetone adsorption reveal that Nb2O5 has a strong ability to activate the C=O bond in carbonyl molecules, which helps to generate a metal enolate intermediate and undergo the nucleophilic addition to form a new C–C bond. Furthermore, the applicability of Nb2O5 to aldol condensation is extended to other biomass-derived carbonyl molecules and high yields of target fuel precursors are obtained. Finally, a multifunctional Pd/Nb2O5 catalyst is prepared and successfully used in the one-pot synthesis of liquid alkanes from biomass-derived carbonyl molecules by combining the aldol condensation with the sequential hydrodeoxygenation.