Butyl Formate Research Articles

Metabolite profiling of different Iranian traditional yogurts using an untargeted metabolomics approach

We used gas chromatography-mass spectrometry (GC-MS) with an untargeted metabolomics approach to look at the metabolite profiles of traditional Iranian yogurts made from cow, goat, buffalo, and sheep milk. Results showed that different animal milks significantly influenced physicochemical properties and fatty acid (FA) composition, resulting in diverse metabolites. Over 80 % of all the fatty acids in the yogurt samples were saturated. The main fatty acids found were myristic acid (C14:0), palmitic acid (C16:0), and oleic acid + petroselenic acid (cis-9 C18:1 + cis-6 C18:1). In total, 36 metabolites, including esters, aldehydes, alcohols, and acids, were detected. Some important metabolites that changed yogurt profiles were 2-heptanone, methyl acetate, 2-propanone, butyl formate, and 4-methyl benzal. Associations between metabolite profiles and milk compositional traits were also observed, with statistical models showing a strong correlation between metabolite profiles and FA content. This study is the first to explore the impact of different animal sources and regions in Iran on the metabolome profiles of traditional yogurts. These results give us useful information about how metabolites differ between species and can be used to make new dairy products based on milk compositions and metabolites, which will help with future formulations of autochthonous starters.

Comparative study on nutritional quality and serum biochemical indices of common carp (Cyprinus carpio) aged 11 to 13 months aged cultured in traditional ponds and land-based container aquaculture systems

In the study, the physical characteristics, nutritional composition, mineral elements, volatile substances, and serum biochemistry of common carp (Cyprinus carpio) after rearing for two months were compared and analyzed to reveal the differences in muscle nutritional quality and serum biochemical indices between fish raised in traditional ponds (TP) and land-based container recirculating aquaculture systems (C-RAS). One hundred fish were selected from each aquaculture mode for the following experiments. Results show that: in terms of physical properties, C-RAS frozen seepage rate was significantly lower than that in TP (P < 0.05), the chewiness, gumminess, springiness, resilience, adhesiveness, cohesiveness, and shearing of C-RAS group were significantly higher than in TP (P < 0.01). Regarding muscle nutrients, the moisture, the crude lipid contents of C-RAS group were significantly lower than that of the TP group (P < 0.05), and the crude protein content of C-RAS group was extremely significantly higher than that in TP (P < 0.01). The saturated fatty acids (ΣSFA) and polyunsaturated fatty acids (ΣPUFA) in the muscle of C-RAS were significantly higher than that in TP (P < 0.01), and monounsaturated fatty acids (ΣMUFA) of C-RAS were significantly lower than that in TP (P < 0.01). Methionine content in C-RAS was significantly higher than that in TP (P < 0.05). In terms of mineral elements, the contents of K and Se in C-RAS were significantly higher than those in TP, and the content of Zn in C-RAS was significantly lower than that in TP (P < 0.05). In terms of volatile substances, nonanal, octanal, and benzaldehyde in C-RAS were significantly lower than those in TP(P < 0.01), 2,3-diethyl-5-methylpyrazine, ethyl 3-methylpentanoate, butyl formate were significantly higher than those in TP (P < 0.01). In terms of serum biochemistry, the glucose index in C-RAS was extremely significantly lower than that in TP group, total protein, albumin, alkaline phosphatase, and triglyceride were extremely significantly higher than those in TP (P < 0.01). Experiments show that the aquaculture mode has a large impact on the physical properties of the common carp, nutrients, mineral elements, volatile matter, and serum biochemical. In conclusion, the common carp cultured in C-RAS systems had better muscle nutritional quality, which provides a reference for future regulation of fish nutritional quality by C-RAS.

Water-DMSO Co–Solvent effect and kinetics of acid catalyzed Hydrolysis of butyl formate and Influence on Activation Parameters

The acid catalyzed hydrolysis of butyl formate in presence of 0.1N-HCI in water and the presence of water-DMSO mixture containing up to 30-70% (v/v) was studied over the temperature ranging from 20-400C. The rate of reaction decreases with decrease of water content of the solvent mixture and reached minima at about 70% of organic solvent. The number of water molecule associated with activated complex was showing decrease in trend with increase of temperature, is an indication of change in mechanism from unimolecular to bimolecular in reaction media. The parameters of thermodynamic activation were also calculated and discussed in terms of solvent effect with help of plots of ΔH* versus ΔS*, the isokinetic temperature was calculated and found to be greater than 300.

A study on reaction between chloroformaldehyde and 𝒏 −butanol

The earlier study of the author (Mallick13) shows that chloroform reacts with nitric acid to form chloroformaldehyde. The objective of the present study is to investigate the nature of chemical reaction between chloroformaldehyde and n-butanol. Detailed investigation clearly indicates that chloride ion is formed during the chemical reaction between chloroformaldehyde and n-butanol. 1HNMR spectrum of the product does not show the characteristic peak of alcoholic −𝑂𝐻 group. On the basis of experimental studies and 1HNMR spectroscopy analysis, a probable mechanism is proposed to explain the reaction between chloroformaldehyde and n-butanol. The mechanism shows that n-butyl formate is formed during the reaction between chloroformaldehyde and n-butanol Keywords: Chloroform, Nitric acid, Chloroformaldehyde, 𝑛 −Butanol, Silver nitrate, 𝑛 −Butyl formate.

Promotion effect of molten salt hydrate on co-esterification of biomass-derived levulinic and formic acids

Efficient esterification of biomass-derived levulinic acid (LA) to levulinate was investigated in molten salt hydrates (MSH) for the first time. A series of molten salt hydrates (LiBr·3H2O, LiCl·3H2O, ZnCl2·3H2O, CaCl2·3H2O and CaBr2·3H2O) were examined in terms of their catalytic activity and Hammett acidity (H0). Among them, CaBr2·3H2O, ZnBr2·3H2O and ZnCl2·3H2O exhibited excellent activity. It was found that formic acid (FA), a compound that is cogenerated with LA in converting cellulose and hemicellulose as well as their derived sugars, can significantly enhance esterification of LA when reacting in MSHs. Mechanism analysis demonstrated that the promotion effect of FA on the formation of levulinate was resulted from transesterification of LA with butyl formate (BF). Under same conditions, as high as 99.8 % of butyl levulinate (BL) yield was obtained in CaCl2·3H2O, while it was merely 19.6% in the absence of CaCl2·3H2O. Hammett acidity measurement confirmed that CaCl2·3H2O is able to promote the protonation of LA and FA, and thus accelerating the esterification and transesterification reactions. Besides, reacting in CaCl2·3H2O can spontaneously form a biphasic reaction system: an organic phase that mainly consists of BL and n-butanol, and an aqueous phase composed of CaCl2, acids and water. Such a biphasic system help boost the esterification equilibrium and the subsequent separation and purification of the synthesized esters.

Diffusion mechanism and properties of chemical liquids and their mixtures in 977‐2 epoxy resin

AbstractEpoxy resin is a versatile high‐performance thermosetting material with attractive properties for many engineering applications. However, epoxy resins may come into contact with various chemical liquid environments while in service which can degrade their mechanical properties and deteriorate their performance. Water diffusion into epoxy resins is well‐studied; however, little research has been reported on the diffusion mechanisms of other liquids/solvents and their mixtures. Therefore, this study addresses this gap through the use of gravimetric analysis to investigate the absorption of water and various chemical liquids, and their mixtures into epoxy resin. The liquid diffusion characterizations, which include weight gain, diffusion coefficients, and edge effects have been investigated. A two‐stage absorption process was observed for water, ethanol, methanol, and their mixtures. A unique three‐stage diffusion process of butyl formate, decalin, and their mixtures in 977‐2 epoxy resin was observed. A correction factor was used to account for the edge effects. The experimental results showed a dependency of saturation levels and diffusion coefficients on the polarity of the liquids and on the interaction level between the penetrants and the polymer. Furthermore, the absorption rate of the binary mixtures is intermediate between the rates of either penetrant.

Oxidation of C5 esters: Influence of the position of the ester function

AbstractThe oxidation of esters has been extensively studied over the past 15 years, mainly focusing on methyl‐ and ethyl‐esters. Recently, the oxidation of esters produced from higher alcohols has received more and more attention. In this work, we report experiments and modeling on the oxidation of a series of four esters with five carbon atoms, namely, methyl butanoate, ethyl propanoate, propyl acetate, and butyl formate. The oxidation of these esters was performed in a jet‐stirred reactor under the same experimental conditions (τ = 700 ms, p = 10 atm, φ = 1, and Xfuel, initial = 1000 ppm). The mole fraction profiles obtained from these experiments were used to develop a unique detailed kinetic mechanism for the oxidation of these four esters, which performs well against our experimental data and on data from the literature. Although these esters are isomers, this work highlights the influence of the position of the ester function in terms of global reactivity and product distribution. In particular, this comparison shows the strong impact of the nature of the products (i.e., acid + alkene) formed by the different molecular decomposition reactions during the oxidation process of these esters.

Antibacterial Activity of Volatile Organic Compounds Produced by the Octocoral-Associated Bacteria Bacillus sp. BO53 and Pseudoalteromonas sp. GA327.

The present research aimed to evaluate the antibacterial activity of volatile organic compounds (VOCs) produced by octocoral-associated bacteria Bacillus sp. BO53 and Pseudoalteromonas sp. GA327. The volatilome bioactivity of both bacteria species was evaluated against human pathogenic antibiotic-resistant bacteria, methicillin-resistant Staphylococcus aureus, Acinetobacter baumanni, and Pseudomonas aeruginosa. In this regard, the in vitro tests showed that Bacillus sp. BO53 VOCs inhibited the growth of P. aeruginosa and reduced the growth of S. aureus and A. baumanni. Furthermore, Pseudoalteromonas sp. GA327 strongly inhibited the growth of A. baumanni, and P. aeruginosa. VOCs were analyzed by headspace solid-phase microextraction (HS-SPME) joined to gas chromatography-mass spectrometry (GC-MS) methodology. Nineteen VOCs were identified, where 5-acetyl-2-methylpyridine, 2-butanone, and 2-nonanone were the major compounds identified on Bacillus sp. BO53 VOCs; while 1-pentanol, 2-butanone, and butyl formate were the primary volatile compounds detected in Pseudoalteromonas sp. GA327. We proposed that the observed bioactivity is mainly due to the efficient inhibitory biochemical mechanisms of alcohols and ketones upon antibiotic-resistant bacteria. This is the first report which describes the antibacterial activity of VOCs emitted by octocoral-associated bacteria.

Antifungal activity of the volatile organic compounds produced by Bacillus velezensis strains against postharvest fungal pathogens

Abstract It is known that Volatile Organic Compounds (VOCs), among several other mechanisms, are responsible for the antagonistic activity produced by microorganisms. In this work the volatilome of three biocontrol Bacillus velezensis strains (BUZ-14, I3 and I5) was tested in vitro and on fruit against Botrytis cinerea, Monilinia fructicola, M. laxa, Penicillium italicum, P. digitatum and P. expansum. In vitro, pathogens growth was significantly inhibited, in particular M. laxa, M. fructicola and P. italicum (66, 72 and 80 %, respectively) by BUZ-14 and B. cinerea (100 %) by I3 and I5, compared to the control. In vivo tests also showed significant inhibitions since volatile metabolites of I3 reduced grey mould in grapes by 50 % and those of BUZ-14 decreased brown rot severity in apricots, especially by M. fructicola, from 60 to 4 mm. VOCs were identified by solid phase microextraction (SPME) coupled with Gas Chromatography-Mass Spectrometry (GC–MS) and the antifungal activity of some of them was tested both in vitro and in vivo against the fungal pathogens. The main volatiles identified ranged from 12 to 15 compounds including 2-nonanone, 2-undecanone, 2-heptanone, 1-butanol, acetoin, benzaldehyde, butyl formate, diacetyl, nonane, or pyrazine, among others. Benzaldehyde and diacetyl obtained the lowest minimum inhibitory concentrations in vitro, ranging from 0.005 to 0.125 mL L−1 depending on the pathogen tested. Moreover, diacetyl was able to control grey mould caused by B. cinerea in table grapes with only 0.02 mL L−1 and to reduce blue rot in mandarins at the same dose up to 60 %. In this study, diacetyl and benzaldehyde have been identified as promising compounds to apply in active packaging during the postharvest commercialization of fruit. However, prior to the application, it is crucial to determine not only the active dose but also the phytotoxic, since some fruit species such as apples and apricots have proven to be highly sensitive.

Improvement of Detection Sensitivity of Triglyceride with Methylamine Formate as Ionization Enhancer in Reversed Phase Liquid Chromatography-Electrospray Ionization Mass Spectrometry

Abstract A novel ionization enhancer, methylamine formate, was proposed for improving the detection sensitivity of triglyceride in edible oil by reversed phase liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS). The commonly used isopropanol-acetonitrile-methanol-water and isopropanol-acetonitrile were selected as the mobile phase. By using a reversed phase C18 column, and taking the corn oil in isopropyl alcohol as sample solution, we compared methylamine formate with ammonium formate, as ionization enhancers, for their effect on the detection sensitivity of triglyceride by LC-ESI-MS after screening other different ionization enhancers, such as formic acid, acetic acid, ammonium formate, ammonium acetate, butyl formate, dibutylamine formate, triethylamine formate, diethylamine formate, methylamine formate, and ethylamine formate. The result indicated that, using methylamine formate in mobile phase, the mass spectral peak response and the signal to noise ratio of trilinolein component were all about 5 times higher than that using ammonium formate. The effect of the concentration of methylamine formate ionization enhancer, the flow rate of the mobile phase and the flow rate of nebulizing gas on the detection of methylamine formate was investigated. The concentration of triglyceride components in corn oil starting to form aggregates was similar in different mobile phases in the electrospray process according to measurement of the relationship between corn oil concentrations and the total ion chromatogram peak area of triglyceride. In particular, the peak area of trilinolein was linear with its concentration in the range of 7 × 10 −7 −2 × 10 −4 M with the correlation coefficient R 2 = 0.9997, but increased slower in the higher concentration range. According to the experimental data, the mechanism for improvement of detection sensitivity of methylamine formate was suggested as that the addition of methylamine mono-charged ions with hydrophobic groups had lower solvation energy, which made the enriched addition ions easily evaporation from the droplet surface, thus improving the electrospray ionization efficiency. This method provided an effective way to improve the detection sensitivity of triglyceride in edible oil by LC-ESI-MS.

A Chemical Kinetic Investigation on Butyl Formate Oxidation: Ab Initio Calculations and Experiments in a Jet-Stirred Reactor

Biofuels are expected to play a significant role in the quest for greener energy generation. In this perspective, esters produced from biomass are promising candidates. This work presents the first computational kinetic study on n-butyl formate (BF) oxidation under combustion conditions coupled to an experimental study in a jet-stirred reactor. Absolute rate constants for hydrogen abstraction reactions by the OH radical were calculated using the G3//MP2/aug-cc-pVDZ model chemistry, in conjunction with statistical rate theory (TST). Subsequently, the fate of the butyl formate radicals was also investigated by calculating absolute rate constants for combustion relevant decomposition channels such as β-scission and hydrogen transfer reactions. The derived rate expressions were used in the presently developed detailed kinetic mechanism, which was validated over experimental data obtained in a jet-stirred reactor at 10 atm and for three different mixtures (φ = 0.45, 0.9, and 1.8). Rate of production analyses w...

Isobaric Vapor–Liquid Equilibrium for Binary Systems of Thioglycolic Acid with Water, Butyl Acetate, Butyl Formate, and Isobutyl Acetate at 101.3 kPa

The isobaric vapor–liquid equilibrium (VLE) data for the systems (thioglycolic acid + water), (thioglycolic acid + butyl acetate), (thioglycolic acid + butyl formate), and (thioglycolic acid + isobutyl acetate) were measured at P = 101.3 kPa by using a vapor recirculating type (modified Rose) equilibrium still. The thermodynamic consistency test of the experimental data for the four binary systems were confirmed by the method of Van Ness. The experimental VLE data were correlated by the three activity coefficient models of Wilson, nonrandom two-liquid (NRTL), and universal quasi-chemical (UNIQUAC). The results show that all the calculated data by the Wilson, NRTL, and UNIQUAC models are in good agreement with the measured VLE data. Meanwhile, the binary interaction parameters of the three models for the binary systems were regressed.

Reaction products and mechanisms for the reaction of n-butyl vinyl ether with the oxidants OH and Cl: Atmospheric implications

Abstract A reaction product study for the degradation of butyl vinyl ether (CH3(CH2)3OCH CH2) by reaction with chlorine atoms (Cl) and hydroxyl radicals (OH) has been carried out using Fourier Transform Infrared absorption spectroscopy (FTIR) and/or Gas Chromatography-Mass Spectrometry with a Time of Flight analyzer (GC-TOFMS). The rate coefficient for the reaction of butyl vinyl ether (BVE) with chlorine atoms has also been evaluated for the first time at room temperature (298 ± 2) K and atmospheric pressure (708 ± 8) Torr. The rate coefficient obtained was (9.9 ± 1.5) × 10−10 cm3 molecule−1 s−1 and this indicates the high reactivity of butyl vinyl ether with Cl atoms. However, this value may be affected by the dark reaction of BVE with Cl2. The results of a qualitative study of the Cl reaction show that the main oxidation products are butyl formate (CH3(CH2)3OC(O)H), butyl chloroacetate (CH3(CH2)3OC(O)CH2Cl and formyl chloride (HCOCl). Individual yields in the ranges ∼16–40% and 30–70% in the absence and presence of NOx, respectively, have been estimated for these products. In the OH reaction, butyl formate and formic acid were identified as the main products, with yields of around 50 and 20%, respectively. Based on the results of this work and a literature survey, the addition of OH radicals and Cl atoms at the terminal C atom of the double bond in CH3(CH2)3OCH CH2 has been proposed as the first step in the reaction mechanism for both of the studied oxidants. The tropospheric lifetime of butyl vinyl ether is very short and, as a consequence, it will be rapidly degraded and will only be involved in tropospheric chemistry at a local level. The degradation products of these reactions should be considered when evaluating the atmospheric impact.

Efficient Hydrogenation of Alkyl Formate to Methanol over Nanocomposite Copper/Alumina Catalysts

The production of methanol, an important fuel and chemical feedstock, from carbon dioxide is an important process for CO2 utilization. We describe herein a mild and efficient method for the indirect hydrogenation of carbon dioxide to methanol via a CO2-derived formate ester intermediate by using a simple heterogeneous catalyst system comprising Cu highly dispersed in an alumina matrix under solvent-free conditions. This catalyst is also effective for the hydrogenation of other formate esters, such as ethyl formate, propyl formate, and butyl formate.

Removal of methyl tertiary butyl ether (MTBE) from contaminated water using UV-assisted nano composite materials

This study was designed to examine the efficacy of UV-assisted nano material treatments to remove methyl tertiary butyl ether (MTBE) from contaminated water. The focus was to investigate the applicability of combining the degradation potential of nano TiO2 photocatalysis and adsorption power of carbon nano tubes (CNTs). Effect of different combinations of two ultraviolet radiations (UVA and UVC) and three types of nano materials: TiO2, CNTs, and TiO2/CNTs on MTBE remediation was studied. Removal efficiency of different combinations varied significantly with highest removal (95%) achieved by UVC-TiO2, followed by UVC-CNTs (75%) and UVA-TiO2/CNTS (60%). However, additive effect of UV/TiO2/CNTs on MTBE removal from water was not observed. Major degradation byproducts formed were acetone, tertiary butyl formate, and tertiary butyl alcohol.

Correction to “Hydrogen Abstraction from n-Butyl Formate by H• and HO2•”

Correction to “Hydrogen Abstraction from <i>n</i>-Butyl Formate by H^• and HO₂^•”

Assessment, measurement and correlation of (vapour + liquid) equilibrium of (carbon dioxide + butyl, isobutyl, and amyl formate) systems

In this work, three formates (butyl, isobutyl, and amyl formate) were considered as relative perfect CO2 absorption performance based on the excess Gibbs function as the thermodynamics criterion. An online static-analytical method was used to measure the (vapour + liquid) equilibrium (VLE) data for the CO2+butyl, isobutyl, and amyl formates under the pressure of (0.2 to 6)MPa and the temperatures at a range from (283.15 to 343.15)K. Then the VLE data were correlated by Peng–Robinson (PR) equation of state (EOS) with classic mixing rule, PR EOS with Wong–Sandler (WS) mixing rule and Soave–Redlich–Kwong (SRK) EOS with classic mixing rule. It is shown that SRK EOS is comparatively appropriate for CO2+butyl formate binary system. Both PR EOS with classic mixing rule and SRK EOS can be used to correlate the binary systems of CO2+isobutyl, amyl formate. It is found that the solubility order of three formates for CO2 from high to low is arranged as CO2+amyl formate>CO2+butyl formate>CO2+isobutyl formate, showing the system of CO2+amyl formate has the best absorption performance. By comparison, it indicates that formates have a greater solubility for CO2 than acetates on the condition of the same temperature and pressure. In addition, the thermophysical properties, mole absorption and mass absorptive amount of several industrial absorbents were assessed and the absorption performance of amyl formate for CO2 is better than other physical absorbents. Thus, the study concluded that amyl formate has potential research value as physical absorbent for CO2 capture.

Mechanistic and kinetic study on the ozonolysis of n-butyl vinyl ether, i-butyl vinyl ether and t-butyl vinyl ether

Density functional theory (DFT) and ab initio method are employed to elucidate the mechanisms for O3-initiated oxidation of n-butyl vinyl ether (n-BVE) and its isomers (i-BVE and t-BVE). For each BVE, the reactions proceed via O3 cycloaddition resulting in the formation of primary ozonides (POZs) and then two self-decomposition pathways of POZs are followed. Major products are identified to be formaldehyde and butyl formates (CH3CH2CH2CH2OCHO for n-BVE, (CH3)2CHCH2OCHO for i-BVE and (CH3)3COCHO for t-BVE). The total and individual rate constants for main product channels have been calculated using the modified multichannel Rice–Ramsperger–Kassel–Marcus (RRKM) approach. At 298K and 101kPa, the calculated total rate constants are 2.50×10−16, 3.41×10−16 and 4.17×10−16cm3molecule−1s−1 for n-BVE+O3, i-BVE+O3 and t-BVE+O3, respectively, which are in perfect agreement with experimental results. The total rate coefficients are almost pressure independent in the range of 0.001–101kPa but obviously positive temperature dependent over the whole study temperature range (200–400K). Also, the favorable reaction pathways have been determined through the estimation of branching ratios. Moreover, the influence of alkoxy group structure on the reactivity of vinyl ethers was examined.

Reaction kinetics studies of the conversions of formic acid and butyl formate over carbon-supported palladium in the liquid phase

Formic acid and butyl formate conversion were studied in the liquid phase over Pd and Ru catalysts. Pd/C was more active, selective, and stable for CO2/H2 production in the liquid phase. Kinetic studies were performed over Pd/C at temperatures from 403 to 443K, at space velocities from 3.8 to 970h−1, in the presence of CO and H2 at partial pressures from 0 to 0.4 and 12.6atm, respectively, and liquid water. Space velocity studies probed the importance of primary decomposition pathways to CO2 and CO compared to the secondary water–gas shift reaction. Generally, the rate of the primary pathway was an order of magnitude higher than the rate of the secondary pathway. Over Pd/C, formic acid decomposed primarily via decarboxylation (to CO2/H2), whereas butyl formate primarily decomposed via decarbonylation (to CO/butanol). When water was present, the formate ester hydrolyzed, which increased the selectivity toward CO2 and H2.

Conversion of Biomass‐Derived Levulinate and Formate Esters into γ‐Valerolactone over Supported Gold Catalysts

The utilization of biomass has recently attracted tremendous attention as a potential alternative to petroleum for the production of liquid fuels and chemicals. We report an efficient alcohol-mediated reactive extraction strategy by which a hydrophobic mixture of butyl levulinate and formate esters, derived from cellulosic biomass, can be converted to valuable γ-valerolactone (GVL) by a simple supported gold catalyst system without need of an external hydrogen source. The essential role of the supported gold is to facilitate the rapid and selective decomposition of butyl formate to produce a hydrogen stream, which enables the highly effective reduction of butyl levulinate into GVL. This protocol simplifies the recovery and recycling of sulfuric acid, which is used for cellulose deconstruction.