591-68-4

Usage

Uses

Used in Food Industry:
n-Butyl valerate is used as a food flavoring agent for imparting a fruity aroma to food products, enhancing their overall taste and appeal.
Used in Chemical Production:
n-Butyl valerate is used as a chemical intermediate in the synthesis of various chemicals, contributing to the development of a wide range of products in the chemical industry.

InChI:InChI=1/C9H18O2/c1-3-5-7-9(10)11-8-6-4-2/h3-8H2,1-2H3

Upstream product

• 71-36-3 butan-1-ol 
• 109-52-4 valeric acid 
• 2082-59-9 pentanoic anhydride 
• 26719-05-1 mercuric n-valerate 
• 638-29-9 n-valeryl chloride 
• 61097-75-4 2-nitro-3-heptanone 
• 201230-82-2 carbon monoxide 
• 2374-26-7 butylmercury ⁽¹⁺⁾; nitrate 
• 109-65-9 1-bromo-butane 
• 16179-36-5 2-Hydroxyethyl pentanoate 
• 502-56-7 nonanone-5 
• 925-19-9 dipentanoyl peroxide 
• 24406-16-4 lithium di-n-butylcuprate 
• 81357-55-3 S-2-pyridyl pentanothioate 

Relevant academic research and scientific papers

Eco-Friendly Natural Clay: Montmorillonite Modified with Nickel or Ruthenium as an Effective Catalyst in Gamma-Valerolactone Synthesis

Ni/Ru metals supported on cheap and available support montmorillonite K10 were used for the selective hydrogenation of levulinic acid to γ-valerolactone. Different loadings of the metals were applied by the impregnation method, and detailed characterization was performed (UV–VIS, XRD, TPR, TPD, particle size distribution, SEM, XRF). Metals’ homogeneous distribution on the surface was confirmed. The selectivity to the desired product was almost independent on the used material. A detailed study of the influence of solvents on the studied reaction was also performed—protic alcohol-based solvents caused the formation of levulinic and valeric acid esters in the reaction mixture. The selectivity was influenced mainly by the alcohol structure (the highest selectivity obtained using isopropyl alcohol and sec-butanol). Mainly the solvent’s donor number (except ethanol) influenced the reaction rate. The prepared catalysts are promising, available, and cheap materials for the studied reaction. Solvent may significantly influence the yield of γ-valerolactone. Graphic Abstract: [Figure not available: see fulltext.].

Development and Validation of a Novel Free Fatty Acid Butyl Ester Gas Chromatography Method for the Determination of Free Fatty Acids in Dairy Products

Accurate quantification of free fatty acids in dairy products is important for both product quality control and legislative purposes. In this study, a novel fatty acid butyl ester method was developed, where extracted free fatty acids are converted to butyl esters prior to gas chromatography with flame ionization detection. The method was comprehensively validated to establish linearity (20-700 mg/L; R2 > 0.9964), limits of detection (5-8 mg/L), limits of quantification (15-20 mg/L), accuracy (1.6-5.4% relative error), interday precision (4.4-5.3% relative standard deviation), and intraday precision (0.9-5.6% relative standard deviation) for each individual free fatty acid. A total of 17 dairy samples were analyzed, covering diverse sample matrices, fat content, and degrees of lipolysis. The method was compared to direct on-column injection and fatty acid methyl ester methods and overcomes limitations associated with these methods, such as either column-phase absorption or deterioration, accurate quantification of short-chain free fatty acids, and underestimation of polyunsaturated free fatty acid.

Sol-gel immobilisation of lipases: Towards active and stable biocatalysts for the esterification of valeric acid

Alkyl esters are high added value products useful in a wide range of industrial sectors. A methodology based on a simple sol-gel approach (biosilicification) is herein proposed to encapsulate enzymes in order to design highly active and stable biocatalysts. Their performance was assessed through the optimization of valeric acid esterification evaluating the effect of different parameters (biocatalyst load, presence of water, reaction temperature and stirring rate) in different alcoholic media, and comparing two different methodologies: conventional heating and microwave irradiation. Ethyl valerate yields were in the 80–85% range under optimum conditions (15 min, 12% m/v biocatalyst, molar ratio 1:2 of valeric acid to alcohol). Comparatively, the biocatalysts were slightly deactivated under microwave irradiation due to enzyme denaturalisation. Biocatalyst reuse was attempted to prove that good reusability of these sol-gel immobilised enzymes could be achieved under conventional heating.

Preparation of valeric acid and valerate esters from biomass-derived levulinic acid using metal triflates + Pd/C

Recently, great attention has been paid to the study of the conversion of biomass-derived compounds to value-Added chemicals. Levulinic acid (LA) is a versatile and valuable chemical and its various applications have been described. The selective conversion of biomass-derived LA to produce valeric acid and valerate esters was successfully performed in the presence of H2, in which metal triflates and Pd/C were used as the catalysts. Under optimal conditions, a 99% conversion of LA and a 92% selectivity of valeric acid was obtained with Hf(OTf)4 and Pd/C as the catalysts at a relatively low temperature of 150 °C. Moreover, the metal center of the catalyst, the solvent, the reaction temperature and other reaction conditions were studied. In addition, the results of the recycling experiment exhibited that the catalysts continued to have a satisfactory activity after being reused 5 times.

Highly efficient transformation of Γ-valerolactone to valerate esters over structure-controlled copper/zirconia catalysts prepared via a reduction-oxidation route

Design and development of novel and efficient catalysts are crucial but challenging for the catalytic conversion of biomass and derivatives to fuels and chemicals. In this paper, a novel separate nucleation and aging steps assistant reduction-oxidation strategy was developed to synthesis CuO/ZrO2 complex precursor with homogeneously distributed Cu and Zr components, which can be used as an ideal precursor for the synthesis of highly dispersed Cu/ZrO2 catalyst. Characterization results revealed that homogeneous dispersion of CuO, high surface area of ZrO2 support with controlled porous structure, and strong interaction between CuO and ZrO2 in CuO/ZrO2 precursor could lead to the enhanced Cu dispersion and the formation of Cu+ active centers. The synthesized Cu/ZrO2 catalysts exhibited excellent catalytic performance (85.4% conversion of GVL and 98.0% selectivity of pentyl valerate) in the catalytic transformation of GVL to valerate esters, more efficient than that of Cu/ZrO2-CP and Cu/ZrO2-CH catalysts prepared via co-precipitation and chemisorption hydrolysis methods, respectively. The superior catalytic performance was mainly attributed to both the cooperation of Cu0 and Cu+ species and the highly dispersed surface Cu0, thereby improving the adsorption and polarization of C[dbnd]O bond in GVL and the following dissociation of H2 to produce active hydrogen for the hydrogenation step during the catalytic transformation of GVL. Moreover, such copper-based catalysts exhibited potential applications in the exploitation and utilization of biomass resources with significantly enhanced efficiency.

Deep eutectic solvent choline chloride·2CrCl3·6H2O: An efficient catalyst for esterification of formic and acetic acid at room temperature

A highly efficient and selective method for esterification of formic and acetic acid with alcohols has been achieved at room temperature, with the choline chloride (ChCl)/chromium(iii) chloride hexahydrate (CrCl3·6H2O) deep eutectic solvent as a catalyst. High yields and good selectivities of organic esters are obtained using DES [ChCl][CrCl3·6H2O]2 with the molar ratio 5:1 (carboxylic acids:alcohols) at room temperature in 24 h. The ease of recovery and reusability of DES with high catalytic activity makes this method efficient and practical.

Synthesis of carboxylic acid esters in the presence of micro- and mesoporous aluminosilicates

The catalytic properties of zeolites HY, HBeta, and HZSM-12 and of mesoporous amorphous aluminosilicate in liquid-phase esterification of aliphatic (monobasic C1-C18, dibasic C6, C10) and aromatic (benzoic, trimellitic, phthalic) carboxylic acids with butanol were studied. Zeolite HBeta appeared to be the most active catalyst. Procedures were developed for preparing esters in the presence of zeolitic catalyst HBeta, ensuring 100% selectivity of ester formation at 90-98% conversion of the acid.

Ruthenium-catalyzed hydrogenation of levulinic acid: Influence of the support and solvent on catalyst selectivity and stability

The catalytic performance of 1 wt% Ru-based catalysts in the hydrogenation of levulinic acid (LA) has been studied at 40 bar H2 and 473 K. This was done by assessing the influence of the support acidity (i.e., Nb 2O5, TiO2, H-β, and H-ZSM5) and solvent (i.e., dioxane, 2-ethylhexanoic acid (EHA), and neat LA). The Ru/TiO2 gave excellent selectivity to γ-valerolactone (GVL) (97.5%) at 100% conversion and was remarkably stable even under severe reaction conditions. Ru/H-ZSM5 showed a 45.8% yield of pentanoic acid (PA) and its esters in dioxane, which is the first example of this one-pot conversion directly from LA at 473 K. The gradual deactivation of zeolite-supported catalysts in EHA and neat LA was mainly caused by dealumination, as confirmed by 27Al MAS NMR. Coke buildup originated from angelicalactone and, remarkably, occurred preferentially in the zigzag channels of H-ZSM5 as shown by systematic shifts in the XRD patterns. The GVL ring-opening step is considered to be the rate-determining step on the pathway to PA, necessitating an acidic support.

Catalytic conversion of biomass-derived levulinic acid to valerate esters as oxygenated fuels using supported ruthenium catalysts

The development of the catalytic conversion of biomass-based platform molecules into oxygenated fuel molecules is of great significance in order to reduce the dependence on fossil resources and to solve environmental problems. Alkyl valerate esters were proven to have the potential to be renewable additives of gasoline and diesel. In this work, we studied the hydrogenation of levulinic acid (LA) to valerate esters over supported Ru catalysts, and found that the acidity was an important factor for the catalyst performance. A bifunctional catalyst Ru/SBA-SO3H was developed as an active catalyst, and a highest yield of 94% to ethyl valerate (EV) was achieved. The catalyst was characterized by nitrogen adsorption/desorption methods, X-ray power diffraction (XRD), transmission electron spectroscopy (TEM) and X-ray photoelectron spectroscopy (XPS). The effects of reaction conditions were comprehensively investigated and probable reaction pathways were proposed and verified. The conversion of LA to various alkyl valerate esters can also be catalyzed by the bifunctional catalyst. In addition, supported Cu and Ni catalysts were also screened under similar reaction conditions as Ru-based catalysts, and the combination of Ni/SBA-15 and SBA-SO3H exhibited activity for the conversion of LA to EV.

Synthesis of short chain alkyl esters using cutinase from Burkholderia cepacia NRRL B2320

Short chain alkyl esters are well appreciated for fruity flavors they provide. These are mainly applied to the fruit-flavored products like jam, jelly, beverages, wine and dairy. Cutinase from Burkholderia cepacia NRRL B 2320 was found to be active in catalyzing the synthesis of alkyl esters in organic solvent. The optimal temperature range for the enzyme catalyzed synthesis was found to be from 35 °C to 40 °C. The maximum conversion (%) during synthesis of ester was obtained for butyric acid (C4) and valeric acid (C5) with butanol reflecting the specificity of the enzyme for short-chain length fatty acids. In case of alcohol specificity, butanol was found to be most preferred substrate by the enzyme and conversion (%) decreased with increasing carbon chain length of alcohol used in the esterification reaction. The kinetic analysis for the synthesis of butyl butyrate by varying concentration of one substrate at a time (butanol or butyric acid), showed that Ping-Pong Bi Bi model with acid inhibition and influence of initial water is most suitable model for the prediction of the reaction kinetics.