3757-32-2

Usage

Uses

Used in Food and Beverage Industry:
Isobutyl 4-oxovalerate is used as a flavoring agent for its fruity scent, enhancing the taste and aroma of various food and drink products, contributing to a more enjoyable consumer experience.
Used in Perfume Production:
Isobutyl 4-oxovalerate serves as a fragrance ingredient in perfumes, leveraging its pleasant scent to create appealing and long-lasting olfactory effects in a range of scented products.
Used in Cosmetics:
In the cosmetics industry, isobutyl 4-oxovalerate is used as a scent component, adding a fresh and fruity note to various cosmetic products, thereby improving their sensory appeal.
Used in Cleaning and Household Products:
Isobutyl 4-oxovalerate is utilized as a fragrance additive in cleaning and household products, providing a pleasant aroma that makes the use of these products more enjoyable and masks potential unpleasant odors.

InChI:InChI=1/C9H16O3/c1-7(2)6-12-9(11)5-4-8(3)10/h7H,4-6H2,1-3H3

Upstream product

• 98-00-0 (2-furyl)methyl alcohol 
• 78-83-1 2-methyl-propan-1-ol 
• 123-76-2 levulinic acid 
• 9004-34-6 cellulose 
• 3128-06-1 5-ketohexanoic acid 

Relevant academic research and scientific papers

Esterification of levulinic acid over Sn(II) exchanged Keggin heteropolyacid salts: An efficient route to obtain bioaditives

In this paper, we describe a process to add value to the biomass derivatives (i.e., levulinic acid), converting it to bioadditives over solid Sn(II) exchanged Keggin heteropolyacid salts. These solid catalysts are an attractive alternative to the traditional soluble and corrosive Br?nsted acid catalysts. Among Sn(II) heteropoly salts, the Sn1.5PW12O40 was the most active and selective catalyst, achieving high conversions (ca. 90 %) and selectivity (90–97 %) for alkyl esters and angelica lactone, the main reaction products. The impacts of the main reaction parameters (i.e., catalyst load, temperature, and the molar ratio of alcohol to acid) were investigated. The use of renewable raw material, and an efficient and recyclable catalyst are the main positive features of this process. The Sn1.5PW12O40 catalyst was easily recovered and reused without loss activity.

Efficient alcoholysis of furfuryl alcohol to n-butyl levulinate catalyzed by 5-sulfosalicylic acid

It is urgent to study the utilization of biomass energy to solve the environmental problems caused by the excessive use of fossil fuels. In this study, a rapid and efficient route for the conversion of furfuryl alcohol (FA) into n-butyl levulinate (BL) has been catalyzed by 5-sulfosalicylic acid. The nearly complete conversion of FA and a considerable 99.7% selectivity of BL are obtained under the optimal conditions. Based on the experimental results, a possible mechanism for the alcoholysis of FA is proposed. The present study provided a promising way for alkyl levulinates synthesis over economical and environmentally benign catalysts.

A New Sulfonic Acid-Functionalized Organic Polymer Catalyst for the Synthesis of Biomass-Derived Alkyl Levulinates

Abstract: Alkyl levulinates are important biobased chemicals with great fuel-blending properties and good reactivity. In this work, a new functionalized nitrogen-containing organic polymer bearing sulfonic acid groups (PDVTA-SO3H) was successfully prepared and studied for the esterification of levulinic acid with alcohols to produce alkyl levulinates. The results showed that this sulfonic acid-functionalized organic polymer possessed high catalytic activity, and the yield of n-butyl levulinate reached 97.4% under the mild conditions. PDVTA-SO3H exhibited strong acidic sites and high stability, and would be well expected to be a potential candidate better than some commercial sulfonic solid catalysts for alkyl levulinates production. The catalyst had been reused without any treatment for five times and the results proved its potential for industrial applications. Graphic Abstract: A new sulfonic acid-functionalized organic polymer showed high activity in the conversion of biomass derived levulinic acid into alkyl levulinates.[Figure not available: see fulltext.]

Influence of butanol isomers on the reactivity of cellulose towards the synthesis of butyl levulinates catalyzed by liquid and solid acid catalysts

Butyl esters of levulinic acid form an interesting class of bio-based compounds that can be used, for example, as fuel additives. Their preparation mainly proceeds through the esterification of levulinic acid while the few reported studies on their direct synthesis from cellulose give limited information. In the present work, we studied for the first time in detail the influence of butanol isomers on the non-catalyzed cellulose liquefaction and the acid catalyzed formation of butyl levulinates from cellulose. In the absence of catalysts there was no influence of the alcohol class on liquefaction which reached 70-85% after 2 hours at 300 °C. In the presence of catalysts, we showed that the class of the alcohol had a significant influence on the butyl levulinate yield. With primary alcohols yields of 50% were obtained in the presence of H2SO4 (200 °C, 30 min). This level of yield can be considered as very interesting for these kinds of one-pot transformations involving cellulose. With secondary alcohols, yields less than 20% were obtained while no butyl levulinate was formed with tertiary alcohols. We also report for the first time this transformation in the presence of solid acids. Insoluble Cs2HPW12O40 or sulfated zirconia catalyzed the reaction heterogeneously despite deactivation leading to limited yields of 13% (200 °C, 1 hour). We finally show that water in butanol had an ambivalent role in enhancing the cellulose reactivity but limiting the esterification step and found that 5-7 wt%/butanol of water was the optimum amount.

Efficient conversion of furfuryl alcohol to ethyl levulinate with sulfonic acid-functionalized MIL-101(Cr)

Catalytic ethanolysis of furfuryl alcohol (FA) to ethyl levulinate (EL) with MIL-101(Cr)-SO3H, prepared by simple one-pot hydrothermal treatment, is presented for the first time. The as-prepared catalyst with high surface area, hydrothermal and chemical stability, good dispersion, and feasible accessibility of -SO3H Br?nsted acid sites was found to show superior performance to other sulfonic acid-functionalized solid catalysts. Besides the special textural properties, the obtained good catalytic activity of 79.2% EL yield and 100% FA conversion were also dependent on the density and strength of the Br?nsted acid and the reaction parameters. A slight loss of catalytic activity after five consecutive recycles and the hot filtration experiment confirmed the good stability of MIL-101(Cr)-SO3H. Two coexisting reaction paths for the ethanolysis of FA to EL catalyzed by MIL-101(Cr)-SO3H were proposed, wherein 2-ethoxymethylfuran (2-EMF) was observed to be the dominant intermediate.

Efficient and selective alcoholysis of furfuryl alcohol to alkyl levulinates catalyzed by double SO3H-functionalized ionic liquids

The production of alkyl levulinates from furfuryl alcohol (FAL) in alcohol media was investigated at moderate temperature in the presence of Bronsted acidic ionic liquids. The reaction was examined and optimized under batch conditions, where it was found that furfuryl alcohol was rapidly and almost quantitatively converted into intermediate products including 2-alkoxymethylfuran and 4,5,5-trialkoxypentan-2-one, and high alkyl levulinates yield of 95% can be achieved after reaching a steady state in 2 h. An advantage of this catalyst system is that undesired dialkyl ether (DEE) formed by a side reaction of the dehydration of alcohol is negligible. The Hammett method was used to determine the acidities of these ionic liquids, which indicated that the acidity and the molecular structure have strong effects on the catalytic activity of ionic liquids. Based on the experimental results, a possible mechanism for the alcoholysis of FAL is proposed.

Graphene oxide: An efficient acid catalyst for alcoholysis and esterification reactions

Evidence is presented for graphene oxide (GO), prepared by modified Hummers method, as a highly active, selective and reusable solid-acid catalyst for the production of alkyl levulinates via alcoholysis or esterification. 95.5% yield of ethyl levulinate was achieved by GO in furfuryl alcohol alcoholysis. Moreover, the surface SO3H groups were identified as the primary active sites, while the surface carboxyl groups worked synergistically to adsorb furfuryl alcohol.

Efficient conversion of furfuryl alcohol into alkyl levulinates catalyzed by an organic-inorganic hybrid solid acid catalyst

A clean, facile, and environment-friendly catalytic method has been developed for the conversion of furfuryl alcohol into alkyl levulinates making use of the novel solid catalyst methylimidazolebutylsulfate phosphotungstate ([MIMBS]3PW12O40). The solid catalyst is an organic-inorganic hybrid material, which consists of an organic cation and an inorganic anion. A study for optimizing the reaction conditions such as the reaction time, the temperature and the catalyst loading has been performed. Under optimal conditions, a high n-butyl levulinate yield of up to 93 % is obtained. Furthermore, the kinetics of the reaction pathways and the mechanism for the alcoholysis of furfuryl alcohol are discussed. This method is environmentally benign and economical for the conversion of biomass-based derivatives into fine chemicals. Size zero waste: A clean, facile, and environment-friendly catalytic method has been developed for the conversion of furfuryl alcohol into alkyl levulinates, making use of the novel solid catalyst methylimidazolebutylsulfate phosphotungstate ([MIMBS]3PW 12O40). Under the optimal conditions, a high n-butyl levulinate yield of up to 93 % was obtained, with easy work-up procedures and minimal waste generation.

Reaction of Carboxonium Ions of Cyclic Acetals, IX. - Synthesis of Rosefuran and Structurally Related Terpene-like Esters, Alcohols, and Olefins

Thermolysis of the 4-(o-toluoyloxy)-1,3-dioxolanes 4 leads to the furans 6/7 which, via Grignard reaction, can be converted into the alcohols 8/9.Subsequent dehydratization affords the olefins 10/11, e.g. rosefuran (10a).

Green syntheses of levulinate esters using ionic liquid 1-Methyl imidazolium hydrogen sulphate [MIM][HSO4] in solvent free system

In the present work, n-butyl levulinate is synthesized by esterification of levulinic acid (LA) with n-butanol using Br?nsted acidic ionic liquid [MIM][HSO4] as a catalyst in a solvent free condition. The prepared IL was characterized by FT-IR, 13C‐NMR and 1H–NMR. For optimization study, central composite design (CCD) method was employed. Design of experiments and statistical analysis is performed using Design Expert 11 software. The highest yield 89.6% and selectivity 98.1% of n-butyl levulinate were achieved at 90 °C. Biphasic layers of product and IL were observed resulting in self-separation of product. Effects of changes in variable parameters on conversion like LA: n-butanol molar ratio, LA:IL molar ratio and temperature were studied. Arrhenius plot was obtained and Activation energy (Ea) was calculated as 53.16 KJ/mol. Substrate study was performed on sec-, iso-, and tert-butanol and 1-Pentanol and n-Hexanol giving high yield and selectivity of corresponding levulinate esters. Catalyst was reused five times without significant decrease in yield.