3757-32-2

Basic information

• Product Name: isobutyl 4-oxovalerate
• Synonyms: isobutyl 4-oxovalerate;4-Oxopentanoic acid isobutyl ester;Isobutyl levulinate;Ai3-31915;Einecs 223-162-6;Pentanoic acid, 4-oxo-, 2-methylpropyl ester
• CAS NO: 3757-32-2
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.22154
• EINECS: 223-162-6
• Mol File: 3757-32-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 228°C (estimate)
• Flash Point: 94.5°C
• Appearance: /
• Density: 0.9669
• Vapor Pressure: 0.0539mmHg at 25°C
• Refractive Index: 1.4249 (estimate)
• CAS DataBase Reference: isobutyl 4-oxovalerate(CAS DataBase Reference)
• NIST Chemistry Reference: isobutyl 4-oxovalerate(3757-32-2)
• EPA Substance Registry System: isobutyl 4-oxovalerate(3757-32-2)

Safety Data

• Hazardous Substances Data: 3757-32-2(Hazardous Substances Data)

Usage

General Description

Isobutyl 4-oxovalerate is a chemical compound with the molecular formula C8H14O3. It is an ester, which means it is formed through the reaction of an alcohol (isobutyl alcohol) with a carboxylic acid (4-oxovaleric acid). Isobutyl 4-oxovalerate has a fruity aroma and is commonly used as a flavor and fragrance ingredient in the food and beverage industry. It is also used in the production of perfumes and cosmetics due to its pleasant scent. Additionally, it can be found in some cleaning and household products as a fragrance additive. Isobutyl 4-oxovalerate is considered safe for use in these applications when used in accordance with regulations and guidelines.

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 articles and documents

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.

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.