95-92-1 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 95-92-1 differently. You can refer to the following data:
1. colourless liquid
2. Anhydrous oxalic acid and ethanol were esterified in the presence of toluene to produce crude diethyl oxalate. The crude ester is distilled into finished product. Raw material consumption quota: 985kg / T oxalic acid, 744kg / T ethanol (95%) and 73.4kg/t toluene. Another preparation method is to add ethanol, benzene and oxalic acid into the reactor, heat it to 68 ℃, azeotrope reflux dehydration, and take no water out as the end point of the reaction, then recover benzene to obtain crude diethyl oxalate, distill under reduced pressure, and collect 103 ℃ / 6kpa fraction to diethyl oxalate. It is purified by washing with dilute sodium carbonate solution, drying anhydrous potassium carbonate or sodium sulfate and vacuum distillation.
Another preparation method is to add 45g (0.5mol) of anhydrous oxalic acid ① (2), 81g (1.76mol) of anhydrous ethanol, 200ml of benzene and 10ml of concentrated sulfuric acid into the reaction bottle equipped with agitator and water separator. It is heated under stirring and refluxed at 68 ~ 70 ℃ for azeotropic dehydration. After the water is basically evaporated, ethanol and benzene are evaporated. Wash with water after cooling, wash with saturated sodium bicarbonate solution, wash with water, and dry with anhydrous sodium sulfate. Diethyl oxalate (57g) was obtained by atmospheric distillation and collecting the fraction at 182 ~ 184 ℃, with a yield of 78%. ① dehydrate oxalic acid with anhydrous chloroform water until it crystallizes as follows: steam it with anhydrous oxalic acid and inject it into the powder containing carbon. Filter by suction, dry and store in dryer for standby. Anhydrous oxalic acid can also be prepared by drying directly in an oven. In this experiment, a corresponding amount of oxalic acid containing crystal water can also be used, but the reaction time is longer.
Uses
Different sources of media describe the Uses of 95-92-1 differently. You can refer to the following data:
1. manufacture of phenobarbital, ethylbenzyl malonate, triethylamine, and similar chemicals, plastics, dyestuff intermediates. Solvent for cellulose esters, perfumes.
2. Diethyl oxalate is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates. It is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics. It is involved in the transesterification reaction with phenol to get dipheny oxalate. It is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives. Further, it is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine. In addition to this, it is utilized in the microemulsion synthesis of zinc oxide nanoparticles.
Application
Diethyl oxalate has the general properties of esters. It absorbs moisture in the air and decomposes slowly. It reacts with ammonia to form amide compounds and condenses with acetone to ethyl pyruvate. It is mainly used in the pharmaceutical industry. It is an intermediate of azathioprine, peripheral sulfanilamide, carboxyphenyllipase penicillin, ethoxybenzylpenicillin, chloroquine lactate, thiabendazole, sulfamethoxazole and other drugs. It can be used as an intermediate of plastics, dyes and other products, and as a solvent of cellulose and spices.Diethyl acetate is often used as the substrate of nucleophilic reagent α,γ- Dicarbonyl esters, ketone compounds, synthesis of heterocyclic compounds, etc. synthesis α,γ- Dicarbonyl esters can be formed by nucleophilic substitution reaction between ketones and diethyl oxalate under alkaline conditions α,γ- Dicarbonyl ester (formula 1). The dicarbonyl ester often exists in enol structure and can be used to synthesize heterocyclic compounds (formula 2)
Production Methods
Diethyl oxalate is produced via esterification of ethanol and
oxalic acid. It is a preferred solvent for cellulose acetate and
nitrate.
General Description
A colorless liquid. Flash point 168°F. Slightly denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes; may be mildly toxic by ingestion; may emit irritating fumes in a fire. Vapors are much heavier than air. Used as a solvent for plastics and in the manufacture of perfumes and pharmaceuticals.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Diethyl oxalate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides
Hazard
Toxic by ingestion, strong irritant to skin
and mucous membranes.
Health Hazard
TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Safety Profile
Poison by ingestion.
Flammable liquid when exposed to heat or
flame; can react with oxidzing materials. To
fight fire, use foam, CO2, dry chemical.
When heated to decomposition it emits
acrid smoke and fumes. See also
OXALATES and ESTERS.
Check Digit Verification of cas no
The CAS Registry Mumber 95-92-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 95-92:
(4*9)+(3*5)+(2*9)+(1*2)=71
71 % 10 = 1
So 95-92-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3
95-92-1Relevant articles and documents
Cyanide selective chemodosimeter in aqueous medium, on test strips and its application in real sample analysis
Ghosh, Tamal,Raina, Ashish,Singh, Yadvendra,Yadav, Komal Kumar
, (2020)
Abstract: In this paper, synthesis, characterization and detection of CN? by the compound (N′1E,N′2E)-N′1,N′2-bis((2-hydroxynaphthalen-1-yl)methylene)oxalohydrazide (1) have been reported. Compound 1 is synthesized by the reaction of oxalyldihydrazide and 2-hydroxy-1-naphthaldehyde and characterized by FTIR, 1H NMR and ESI-Mass spectroscopy. UV–Visible spectral band of 1 is observed to be broadened and shifted to longer wavelength upon addition of CN? ion selectively in H2O-DMSO (8:2 v/v) medium. Based on the UV–Visible spectral data, the detection limit of cyanide ion for 1 is found to be 30.2 μM. Colourless solution of 1 changes to yellow in the presence of cyanide ion selectively. The same colour change is also observed on Whatman filter paper test strip. Fluorescence intensity of 1 is quenched due to the nucleophilic addition reaction of cyanide with one of the two imine carbons. 1H NMR titration of 1 with CN? ion corroborates the reaction of the latter with one of the two imine carbons of the former, leading to the appearance of cyanomethyl proton signal at 6.15 ppm and consequently, its behaviour as chemodosimeter. The above mentioned chemodosimeter nature of 1 is also validated by ESI-Mass spectroscopy data. Compound 1 is capable for the detection of CN? in water for real samples with concomitant colour change. Graphic abstract: Compound 1 behaves as selective cyanide chemodosimeter with associated change in its colour (in solution and on Whatman filter paper test strip) and fluorescence. 1H NMR titration and ESI-Mass data confirm the nucleophilic addition reaction of cyanide with 1. Compound 1 can be used for the detection of CN? in water for real samples.[Figure not available: see fulltext.].
-
Fenton,Steinwand
, p. 701 (1974)
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A nanostructured CeO2 promoted Pd/α-alumina diethyl oxalate catalyst with high activity and stability
Jin, Erlei,He, Leilei,Zhang, Yulong,Richard, Anthony R.,Fan, Maohong
, p. 48901 - 48904 (2014)
A Pd/α-Al2O3 nanocatalyst was synthesized and investigated as a catalyst for CO oxidative coupling to diethyl oxalate and CeO2 was used as a promoter. With the highest activity and stability found so far, great CO conversion and diethyl oxalate selectivity were achieved due to the addition of CeO2. This journal is
PROCESS FOR THE SYNTHESIS OF ETHYLENE GLYCOL
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Page/Page column 49-51, (2021/10/11)
The invention relates to a process for the production of ethylene glycol from CO2, comprising the steps of : i) Reducing CO2 to CO; ii) Reacting the CO produced in step i) with an amine to form an oxamide or an oxamate or with an alcohol to form an oxalate; and iii) Reducing the oxamide, oxamate or oxalate formed in step ii) to form ethylene glycol, a process for the production of an oxamide, oxamate or oxalate and a process for the production of polyethylene terephthalate.
