2050-60-4

Basic information

• Product Name: Dibutyl oxalate
• Synonyms: DIBUTYL OXALATE;Dibutyl ethanedioate;ETHANEDIOIC ACID DIBUTYL ESTER;OXALIC ACID DI-N-BUTYL ESTER;Butyl ethanedioate;Dibutyl ester of oxalic acid;Dibutylethanedionate;Oxalic acid, dibutyl ester
• CAS NO: 2050-60-4
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.25
• EINECS: 218-092-8
• Product Categories: Pharmaceutical Intermediates;C10 to C11;Carbonyl Compounds;Esters
• Mol File: 2050-60-4.mol

Chemical Properties

• Melting Point: −29 °C(lit.)
• Boiling Point: 239-240 °C(lit.)
• Flash Point: 228 °F
• Appearance: clear colourless liquid
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.04mmHg at 25°C
• Refractive Index: n20/D 1.423(lit.)
• Water Solubility: Practically insoluble in water
• BRN: 1776065
• CAS DataBase Reference: Dibutyl oxalate(CAS DataBase Reference)
• NIST Chemistry Reference: Dibutyl oxalate(2050-60-4)
• EPA Substance Registry System: Dibutyl oxalate(2050-60-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 37/38-41-43-20/21
• Safety Statements: 26-36/37/39-23
• WGK Germany: 3
• Hazardous Substances Data: 2050-60-4(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Dibutyl oxalate is used as a research compound for studying the degradation rate in ruminal contents, which can help improve our understanding of animal digestion and the factors that influence it.
Used in Veterinary Industry:
Dibutyl oxalate is used as a diagnostic tool to assess the rumen health of adapted and non-adapted animals, potentially aiding in the development of strategies to improve ruminant digestion and overall animal health.

InChI:InChI=1/C10H18O4/c1-3-5-7-13-9(11)10(12)14-8-6-4-2/h3-8H2,1-2H3

Upstream product

• 144-62-7 oxalic acid 
• 71-36-3 butan-1-ol 
• 95-92-1 oxalic acid diethyl ester 
• 79-37-8 oxalyl dichloride 
• 201230-82-2 carbon monoxide 
• 2372-45-4 sodium butanolate 
• 109-65-9 1-bromo-butane 
• 14077-31-7 {NiI₂py4} 
• 14647-21-3 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 
• 14076-99-4 [nickel(II)(pyridine)4(chloride)2] 
• 36673-36-6 dibromobis(triphenylphosphine)nickel(II) 
• 787624-20-8 bis(triphenylphosphine)nickel(II) diiodide 
• 14264-16-5 bis(triphenylphosphine)nickel(II) chloride 
• 14024-85-2 {Ni(pyridine)2}Br₂ 

Downstream Products

• 1871-89-2 N,N'-bis-(2-hydroxyethyl)oxamide 
• 101100-90-7 2,4,6-trimethyl-mandelic acid-butyl ester 
• 22899-33-8 cyclohexyl-hydroxy-acetic acid butyl ester 
• 5524-55-0 n-butyl 2-oxo-2-phenylacetate 
• 10153-83-0 butyl 2,4-dioxopentanoate 
• 5524-58-3 Mesityl-glyoxalsaeure-butylester 
• 136811-00-2 N-[4-(4-Methoxy-phenyl)-thiazol-2-yl]-oxalamic acid butyl ester 
• 64528-22-9 Butoxy-oxalyl-methyl-p-tolyl-sulfon 
• 135-98-8 sec-Butylbenzene 
• 52182-16-8 butyl 2-hydroxy-2,2-diphenylacetate 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 

Relevant articles and documents

Preparation method of dibutyl oxalate

The invention discloses a preparation method of dibutyl oxalate, and relates to the technical field of organic synthesis. The preparation method comprises the steps that in an N,N-dimethylformamide solvent, n-butyl chloride and oxalate are taken as raw materials and react at a certain temperature and reaction time to prepare a dibutyl oxalate crude product, and a dibutyl oxalate product is obtained through water washing, vacuum distillation and drying; N,N-dimethylformamide is selected as the solvent to study various influence factors of the reaction of oxalate and n-butyl chloride in detail;and the amount ratio of the n-butyl chloride to the oxalate is 2.0:1 to 2.2:1, the reaction time is 2-4 h, the reaction temperature is 40-60 DEG C, and the product yield is 68.7-81.7%. According to the preparation method, the reaction is conducted at the low heating temperature, and the production energy consumption of the dibutyl oxalate can be lowered; the preparation method does not need to usea large number of acids or auxiliary reagents, the production cost can be lowered, and the preparation method is environmentally friendlier.

Method for synthesizing symmetric oxalate by using dimethyl oxalate and alcohols in one step

The invention relates to a method for synthesizing symmetric oxalate, in particular to a method for synthesizing the symmetric oxalate by using dimethyl oxalate and alcohols in one step. The symmetricoxalate is synthesized by using the dimethyl oxalate and the high carbon alcohols such as ethanol, propanol, butanol and pentanol as reaction raw materials and by adopting a one-step synthesis method. A catalyst used in the method is a mesoporous-microporous composite multifunctional basic catalyst, and has the advantages that mesopores significantly improve the mass transfer efficiency, while micropores significantly enlarge the specific surface area of a carrier and improve the dispersion of an active center. 10% MgO-5% Al2O3-8% Fe2O3/Na-meso-Y is used as the catalyst, the raw material ethanol and the dimethyl oxalate are enabled to be subjected to reaction under the atmospheric pressure at the temperature of 100 DEG C under the condition that the space velocity is 2 h-1, wherein the molar ratio of the raw material ethanol to the dimethyl oxalate is equal to 20 to 1; the selectivity of the product diethyl oxalate is stabilized to be about 82%, and the steady state operation is performed for 1000h; the catalytic activity and the product selectivity are basically unchanged. The whole reaction path has the characteristics of being short in synthetic route, simple in process flow and high in raw material conversion rate and product selectivity, and enabling the catalyst to be stable and non-deactivated.

Template-free sol–gel synthesis of high surface area mesoporous silica based catalysts for esterification of di-carboxylic acids

High surface area mesoporous silica based catalysts have been prepared by a simple hydrolysis/sol–gel process without using any organic template and hydrothermal treatment. A controlled hydrolysis of ethyl silicate-40, an industrial bulk chemical, as a silica precursor, resulted in the formation of very high surface area (719?m2/g) mesoporous (pore size 67?? and pore volume 1.19?cc/g) silica. The formation of mesoporous silica has been correlated with the polymeric nature of the ethyl silicate-40 silica precursor which on hydrolysis and further condensation forms long chain silica species which hinders the formation of a close condensed structure thus creating larger pores resulting in the formation of high surface mesoporous silica. Ethyl silicate-40 was used further for preparing a solid acid catalyst by supporting molybdenum oxide nanoparticles on mesoporous silica by a simple hydrolysis sol–gel synthesis procedure. The catalysts showed very high acidity as determined by NH3-TPD with the presence of Lewis as well as Br?nsted acidity. These catalysts showed very high catalytic activity for esterification; a typical acid catalyzed organic transformation of various mono- and di-carboxylic acids with a range of alcohols. The in situ formed silicomolybdic acid heteropoly-anion species during the catalytic reactions were found to be catalytically active species for these reactions. Ethyl silicate-40, an industrial bulk silica precursor, has shown a good potential for its use as a silica precursor for the preparation of mesoporous silica based heterogeneous catalysts on a larger scale at a lower cost.

A kind of preparation method of succinic acid diester

Disclosed is a method for preparing succinic acid diester, in which levulinic acid or levulinate esters are used as raw materials, molecular oxygen is used as oxygen source, and succinic acid diester is produced by catalytic selective oxidation and esterification reaction. The levulinic acid or levulinate esters used as raw materials in the method can be obtained from biomass such as cellulose, starch, agricultural and forestry residues or the like. The method is a new route for preparing succinic acid diester that does not rely on fossil resourse. As the reaction condition in the process is moderate and has a high succinic acid diester selectivity, it has important application prospect.

Quaternary Ammonium Salt Functionalized Methoxypolyethylene Glycols-Supported Phosphotungstic Acid Catalyst for the Esterification of Carboxylic Acids with Alcohols

The quaternary ammonium salt functionalized methoxypolyethylene glycols-supported phosphotungstic acid catalyst was prepared and characterized using X-ray diffraction, fourier transform infrared spectroscopy and thermogravimetric analysis. The immobilized phosphotungstic acid catalyst exhibited excellent catalytic activity and selectivity, which was shown to be an efficient heterogeneous catalyst for catalyzing the esterification of carboxylic acids with alcohols under mild conditions. The catalyst could be separated by simple separation and can be used six times without significant losing of catalytic activity and selectivity. Graphical Abstract: [Figure not available: see fulltext.]

Improved oxazole Method for the Practical and Efficient Preparation of Pyridoxine Hydrochloride (Vitamin B6)

Vitamin B6, a well-studied vitamin B, has been synthesized using an oxazole method for the past 20 years. The oxazole method provided 56.2% overall yield but also generated safety, environmental, and health problems, such as using toxic benzene as solvent and unstable, corrosive, and pollutive HCl and POCl3 as reagents. To use the same equipment but the least amount of toxic agents, we developed new reaction conditions for the early steps. For example, we successfully replaced toxic HCl/benzene conditions with NaHSO4/PhCH3 conditions and also developed a novel and efficient dehydrating agent trichloroisocyanuric acid/Ph3P/Et 3N to synthesize the key intermediate 5-butoxy-4-methyl oxazole, instead of using phosphorus oxychloride. These improvements resolved safety, waste avoidance, and workup issues that plagued the previous methodologies. Our process comprised six easy synthetic steps and generated vitamin B6 with 99.4% purity in 56.4% overall yield.

Reductive coupling of aldehydes by H2S in aqueous solutions, a C-C bond forming reaction of prebiotic interest

We report here a novel reductive coupling reaction of conjugated, non- or poorly enolizable aldehydes induced by H2S and operative in aqueous solutions under prebiotically relevant conditions. This reaction leads from retinal to β-carotene, and from benzylic aldehydes to the corresponding diarylethylenes. This novel reaction also opens a new potentially prebiotic pathway leading from glyoxylic acid to various compounds that are involved in the reductive tricarboxylic acid cycle. This C-C bond forming reaction of prebiotic interest might have been operative, notably, in the sulfide-rich environments of hydrothermal vents, which have been postulated as possible sites for the first steps of organic chemical evolution.

Vapor pressures and enthalpies of vaporization of a series of the symmetric linear n -alkyl esters of dicarboxylic acids

Vapor pressures and the molar enthalpies of vaporization of the linear aliphatic alkyl esters of dicarboxylic acids R-CO2-(CH 2)n-CO2-R with n = (0 to 4) with R = C 2H5, n-C3H7, and n-C 4H9 have been determined using the transpiration method. A linear correlation of enthalpies of vaporization (at T = 298.15 K) of the esters with the number n and with Kovat's indices has been found, proving the internal consistency of measured data.

Ionic liquids as solvent for efficient esterification of carboxylic acids with alkyl halides

The selective esterification of carboxylic acid derivatives with a variety of alkyl halides was carried out using ionic liquid as solvent in the presence of triethylamine. The reaction was found to proceed under relatively mild conditions with excellent conversions (up to 99%) and selectivities. The ionic liquid was recycled and reused. TUeBITAK.

Effects of acidity and immiscibility of lactam-based Bronsted-acidic ionic liquids on their catalytic performance for esterification

Several lactam-based Bronsted-acidic ionic liquids with different acidities were synthesized and applied to the esterification of carboxylic acids with alcohols. High conversion and perfect selectivity were obtained under mild conditions. Among the ionic liquids investigated, those having a methyl sulfonate anion (which has weaker acidity than those with a tetrafluoroborate anion) afforded the highest activity for esterification. The results indicated that the acidity and immiscibility of Bronsted-acidic ionic liquids has a synergistic effect on their esterification performance. Furthermore, after removal of water under vacuum, such ionic liquids could be reused several times without substantial loss of activity.