ChemicalBook > CAS DataBase List > Diethyl oxalate

Diethyl oxalate

Product Name
Diethyl oxalate
CAS No.
95-92-1
Chemical Name
Diethyl oxalate
Synonyms
ETHYL OXALATE;OXALIC ACID DIETHYL ESTER;Oxalic ether;Ceftriaxone Impurity 5;GKSW;oxalicether;EthyIoxalate;Diethyl oxate;Diαthyloxalat;Diαthyloxalat
CBNumber
CB4400958
Molecular Formula
C6H10O4
Formula Weight
146.14
MOL File
95-92-1.mol
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Diethyl oxalate Property

Melting point:
-41 °C (lit.)
Boiling point:
185 °C (lit.)
Density 
1.076 g/mL at 25 °C (lit.)
vapor density 
5.03 (vs air)
vapor pressure 
1 mm Hg ( 47 °C)
refractive index 
n20/D 1.410(lit.)
Flash point:
168 °F
storage temp. 
Store below +30°C.
solubility 
Miscible with alcohols, ether and other common organic solvents.
form 
Liquid
color 
Clear
explosive limit
0.42-2.67%(V)
Water Solubility 
MAY DECOMPOSE
Sensitive 
Moisture Sensitive
Merck 
14,3125
BRN 
606350
Dielectric constant
8.2（21℃）
Stability:
Stable, but moisture sensitive. Incompatible with strong oxidizing agents.
InChIKey
WYACBZDAHNBPPB-UHFFFAOYSA-N
LogP
0.560
CAS DataBase Reference
95-92-1(CAS DataBase Reference)
NIST Chemistry Reference
Ethanedioic acid, diethyl ester(95-92-1)
EPA Substance Registry System
Ethyl oxalate (95-92-1)
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Safety

Hazard Codes 
Xn,T
Risk Statements 
22-36-68/21-48/25-35-61-60
Safety Statements 
23-45-36/37/39-28-26-25-24-53
RIDADR 
UN 2525 6.1/PG 3
WGK Germany 
1
RTECS 
RO2800000
Autoignition Temperature
410 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29171900
Hazardous Substances Data
95-92-1(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 400 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P314Get medical advice/attention if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.07059
Product name
Diethyl oxalate
Purity
for synthesis
Packaging
100mL
Price
$33.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.07059
Product name
Diethyl oxalate
Purity
for synthesis
Packaging
500mL
Price
$36.4
Updated
2024/03/01
Sigma-Aldrich
Product number
8.07059
Product name
Diethyl oxalate
Purity
for synthesis
Packaging
1L
Price
$51.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.07059
Product name
Diethyl oxalate
Purity
for synthesis
Packaging
25L
Price
$667
Updated
2024/03/01
Sigma-Aldrich
Product number
135364
Product name
Diethyl oxalate
Purity
≥99%
Packaging
1kg
Price
$63.7
Updated
2024/03/01
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Diethyl oxalate Chemical Properties,Usage,Production

Chemical Properties

colourless liquid

Chemical Properties

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

manufacture of phenobarbital, ethylbenzyl malonate, triethylamine, and similar chemicals, plastics, dyestuff intermediates. Solvent for cellulose esters, perfumes.

Uses

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.

Production Methods

Diethyl oxalate is produced via esterification of ethanol and oxalic acid. It is a preferred solvent for cellulose acetate and nitrate.

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)

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.

Diethyl oxalate Preparation Products And Raw materials

Raw materials

Oxalic acid Ethanol Toluene Ethanol 95% Methanol

Preparation Products

ETHYL 1-METHYL-5-PROPYL-1H-PYRAZOLE-3-CARBOXYLATE 5-TERT-BUTYL-1H-PYRAZOLE-3-CARBOXYLIC ACID 3-Phenyl-1H-pyrazole-5-carboxamide ,97% Ethyl 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylate ,97% 5-(3-CHLOROPHENYL)-1H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL 5-(3-NITROPHENYL)-1H-PYRAZOLE-3-CARBOXYLATE ETHYL 2,4-DIOXOHEPTANOATE 5-Fluoroindole-2-carboxylic acid 3-(4-Methoxyphenyl)-1H-pyrazole-5-carboxamide ,97% 1-Methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide ,97% ETHYL 5-(2-FURYL)-1H-PYRAZOLE-3-CARBOXYLATE ETHYL 5-METHYLISOXAZOLE-3-CARBOXYLATE Ethyl 5-(tert-butyl)-2H-pyrazole-3-carboxylate 3-(4-CHLOROPHENYL)-1H-PYRAZOLE-5-CARBOHYDRAZIDE ETHYL A-ETHOXYOXALYLPHENYL ACETATE 5-Chloroindole 5-METHYL-1 H-PYRAZOLE-3-CARBOXYLIC ACID HYDRAZIDE Ethyl 2,4-dioxovalerate 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid Cromolyn Disodium Salt dimethyl 4-chloropyridine-2,6-dicarboxylate 4-Fluoroindole 5-(4-METHOXY-PHENYL)-2H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL ESTER Gliclazide Ethyl 5-thien-2-yl-1H-pyrazole-3-carboxylate Imazamox 1-METHYL-3-PROPYLPYRAZOLE-5-CARBOXYLIC ACID ETHYL 3-(4-CHLOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLATE ETHYL PROPIONYL PYRUVATE Ethyl 3-(5-methylfuran-2-yl)-1H-pyrazole-5-carboxylate ,97% OROTIC ACID MONOHYDRATE 1-METHYL-5-PROPYL-1H-PYRAZOLE-3-CARBOXYLIC ACID 5-PHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL ESTER ETHYL 1,3-BENZOTHIAZOLE-2-CARBOXYLATE DIETHYL OXALPROPIONATE 5-Methyl-1H-pyrazole-3-carboxylic acid 4-BROMO-5-METHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID Chelidonic acid ETHYL 2-(1-METHYL-1H-IMIDAZOL-2-YL)-2-OXOACETATE 3-(tert-Butyl)-1H-pyrazole-5-carbohydrazide
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Diethyl oxalate Suppliers

Americas 1 Belgium 2 China 316 Czech 1 Czech Republic 2 Europe 2 France 4 Germany 16 India 51 Ireland 1 Japan 8 Poland 1 Slovakia 1 South Korea 2 Switzerland 3 The Netherlands 1 Ukraine 1 United Kingdom 14 United States 49 Global 476
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View Lastest Price from Diethyl oxalate manufacturers

Jinan Finer Chemical Co., Ltd
Product
Diethyl oxalate 95-92-1
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
2000mt/year
Release date
2021-07-16
Hebei Weibang Biotechnology Co., Ltd
Product
Diethyl oxalate 95-92-1
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100 mt
Release date
2024-11-13
Hebei Chuanghai Biotechnology Co,.LTD
Product
Diethyl oxalate 95-92-1
Price
US $10.50/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 ton
Release date
2024-08-21

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  • Dithyl oxalate
  • Diethyl oxalate purum, >=99.0% (GC)
  • Diethyl Oxalate [for SpectrophotoMetry]
  • Diethyl oxalat
  • Diethyleoxalate
  • Ethanedioicacid, 1,2-diethyl ester
  • DiethylOxalate&gt
  • DiethylOxalate[forSpectrophotometry]&gt
  • Diethyl oxalate (DEOX)
  • Diethyl oxalate ISO 9001：2015 REACH
  • Diethyl oxalate, puriss, 99%+
  • Diethyl Oxalate LR
  • Diethyl oxalate, puriss
  • Ceftriaxone Impurity 2
  • Ceftriaxone Impurity 5
  • Ceftriaxone Impurity 11
  • Ceftriaxone Impurity 31
  • EthyIoxalate
  • Diethyl Oxalate, ≥ 98.0%
  • Diαthyloxalat
  • Diethyl Oxalate 99% For Synthesis
  • 95-92-1
  • Solvents for Spectrophotometry
  • Solvents for HPLC & Spectrophotometry