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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;dlethyloxalate
CBNumber:
CB4400958
Molecular Formula:
C6H10O4
Molecular Weight:
146.14
MDL Number:
MFCD00009119
MOL File:
95-92-1.mol
MSDS File:
SDS
Last updated:2023-11-28 16:31:43

Diethyl oxalate Properties

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
Indirect Additives used in Food Contact Substances DIETHYL OXALATE
FDA 21 CFR 175.105
CAS DataBase Reference 95-92-1(CAS DataBase Reference)
EWG's Food Scores 1-3
FDA UNII 860M3ZWF6J
NIST Chemistry Reference Ethanedioic acid, diethyl ester(95-92-1)
EPA Substance Registry System Ethyl oxalate (95-92-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H314-H373
Precautionary statements  P260-P280-P301+P312-P303+P361+P353-P305+P351+P338-P314
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
Toxicity LD50 orally in Rabbit: 400 mg/kg
NFPA 704
2
1 1

Diethyl oxalate price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.07059 Diethyl oxalate for synthesis 95-92-1 100mL $33.1 2024-03-01 Buy
Sigma-Aldrich 8.07059 Diethyl oxalate for synthesis 95-92-1 500mL $36.4 2024-03-01 Buy
Sigma-Aldrich 8.07059 Diethyl oxalate for synthesis 95-92-1 1L $51.6 2024-03-01 Buy
Sigma-Aldrich 8.07059 Diethyl oxalate for synthesis 95-92-1 25L $667 2024-03-01 Buy
Sigma-Aldrich 135364 Diethyl oxalate ≥99% 95-92-1 1kg $63.7 2024-03-01 Buy
Product number Packaging Price Buy
8.07059 100mL $33.1 Buy
8.07059 500mL $36.4 Buy
8.07059 1L $51.6 Buy
8.07059 25L $667 Buy
135364 1kg $63.7 Buy

Diethyl oxalate Chemical Properties,Uses,Production

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.

Chemical Properties

colourless liquid

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.

Uses

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

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)
synthesize heterocyclic compounds

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.

64-17-5
144-62-7
95-92-1
Synthesis of Diethyl oxalate from Ethanol and Oxalic acid

Diethyl oxalate Preparation Products And Raw materials

Raw materials

Preparation Products

1of8

Global( 452)Suppliers
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Anhui Royal Chemical Co., Ltd.
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View Lastest Price from Diethyl oxalate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Diethyl oxalate pictures 2024-03-28 Diethyl oxalate
95-92-1
US $0.00 / Kg/Drum 1KG 99% 2000mt/year Jinan Finer Chemical Co., Ltd
Diethyl oxalate pictures 2023-08-31 Diethyl oxalate
95-92-1
US $100.00 / drum 1drum 99 5000 Hebei Fengqiang Trading Co., LTD
Diethyl oxalate pictures 2023-08-26 Diethyl oxalate
95-92-1
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
AKOS BBS-00004457 Ethanedioic acid diethyl ester DIETHYL OXALATE DIETHYL ETHANEDIOATE RARECHEM AL BI 0114 C2H5OCOCOOC2H5 Diethyl ester of oxalic acid Diethyl ester, oxalic acid Diethylester kyseliny stavelove diethylesterkyselinystavelove dlethyloxalate oxalicether Diethyl oxate DIETHYL OXALATE, STANDARD FOR GC DIETHYL OXALATE, 99+% DiethyloxalateForSynthesis diethyl ethaneioate DIETHYL OXALATE, 98.0% MIN DIETHYL OXALATE, 99.0% MIN Oxalsurediethylester Diαthyloxalat oxalic acid diethylester diethyl oxalate DIETHYL OXALATE pure Diethyl oxalate, 99% 1KG Diethyl oxalate, 99% 2.5KG Diethyl oxalate, 99% 25GR Diethyl oxalate, 99% 500GR Dithyl oxalate Diethyl oxalate purum, >=99.0% (GC) Diethyl Oxalate [for SpectrophotoMetry] Diethyl oxalat Diethyleoxalate Oxalic acid diethyl ester Oxalic acid diethyl ester Oxalic acid diethyl ester DIethlyoxalate GKSW Ethanedioicacid, 1,2-diethyl ester DiethylOxalate> DiethylOxalate[forSpectrophotometry]> Diethyl oxalate (DEOX) Diethyl oxalate ISO 9001:2015 REACH Diethyl oxalate, puriss, 99%+ Diethyl Oxalate LR Diethyl oxalate, puriss ETHYL OXALATE OXALIC ACID DIETHYL ESTER Oxalic ether Diethyloxaiate Ceftriaxone Impurity 2 Ceftriaxone Impurity 11 Ceftriaxone Impurity 5 Ceftriaxone Impurity 31 EthyIoxalate 95-92-1 Solvents for Spectrophotometry Solvents for HPLC & Spectrophotometry Esters DID - DIN Organic Building Blocks