Diethyl Oxalate

HCID 7268

Basic information

CAS
95-92-1
Standard SMILES
CCOC(=O)C(=O)OCC
InChIKey
WYACBZDAHNBPPB-UHFFFAOYSA-N
Molecular formula
C6H10O4
Average molar mass
146.14 g/mol
Monoisotopic mass
146.0579088

Overview

Ethyl oxalate appears as a colorless liquid. 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.

Names & identifiers

Preferred name
Diethyl Oxalate
IUPAC
diethyl oxalate
English name
Diethyl oxalate
Molecular formula
C6H10O4
Molecular weight
146.14

Names & synonyms

DIETHYL OXALATE95-92-1Ethyl oxalateOxalic etherEthyl oxalate (VAN)NSC 8851Diethylester kyseliny staveloveDTXSID2044472HSDB 2131EINECS 202-464-1UNII-860M3ZWF6JDiethyl ester of oxalic acid
Show more names
OXALIC ACID DIETHYL ESTERDEOiethyl oxalateCeftriaxone Impurity 5GKSWoxalicetherEthyIoxalateDiethyl oxate
UN2525Diethylester kyseliny stavelove [Czech]BRN 0606350860M3ZWF6JETHYL OXOLATENSC-8851C2H5OCOCOOC2H5Ethanedioic acid, 1,2-diethyl ester

Database identifiers

CAS
95-92-1
PubChem CID
7268
DTXSID
DTXSID2044472
ChEMBL
CHEMBL3183226
UNII
860M3ZWF6J
EC Number
202-464-1
Nikkaji
J43.379I

Properties

Computed structural properties

XLogP
0.6
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
10

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Esters, Other

Flammable agents - 2nd degree

CosmeticsChelating; Plasticiser; Hair conditioning
SpringerMaterials PropertiesBoiling point
LogP0.56
OdorAROMATIC ODOR
Food AdditivesFood

Physicochemical properties

Melting point
-41 °C · -41 °C (lit.)
Boiling point
185 °C · 185 °C (lit.)
Density
1.076 g/mL · 1.076 g/mL at 25 °C (lit.)
vapor density
5.03 · 5.03 (vs air)
vapor pressure
1 mm · 1 mm Hg ( 47 °C)
refractive index
20 · n20/D 1.410(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P337+P317, P363, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: Ethanedioic acid, diethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanedioic acid, 1,2-diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioic acid, 1,2-diethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14261

Diethyl oxalate: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Oxalate esters (C1-C4): Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· Combustible material: may burn but does not ignite readily.

Fire Potential · 3 items

MODERATE WHEN EXPOSED TO HEAT OR FLAME

THIS ESTER IS A COMBUSTIBLE LIQ, BUT IT DOES NOT PRODUCE A FLAMMABLE CONCN OF VAPOR @ ROOM TEMP.

SOME ESTERS WITH HIGHER FLASH POINTS, LIKE...ETHYL OXALATE, ARE NOT SO DANGEROUS AT ROOM TEMP. THEY ARE NEVERTHELESS READILY IGNITED AS FLAMMABLE LIQ, & SOURCE OF IGNITION MUST NOT BE ALLOWED TO COME IN CONTACT WITH THEM.

Health Hazards · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Safety & protection

Fire FightingExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresFOAM, CARBON DIOXIDE, DRY CHEMICAL
Storage Conditions · 2 items

STORAGE TANKS CONTAINING FLAMMABLE ESTERS SHOULD BE SITUATED IN MOUNDED COMPOUND CONSTRUCTED TO RETAIN MAX QUANTITY OF LIQ THAT COULD ESCAPE FROM TANKS. /ESTERS/

...DRUMS & OTHER SMALLER RECEPTACLES CONTAINING ESTERS SHOULD BE KEPT IN /FIRE RESISTANT/ STOREROOM...WITH MOUNDED OR RAMPED DOORWAY TO PREVENT ESCAPE OF SPILLED LIQ. /ESTERS/

Toxicology

Adverse EffectsNeurotoxin - Acute solvent syndrome
Human Toxicity Excerpts · 5 items

...COMPLAINTS OF WEAKNESS, HEADACHE, AND NAUSEA, TOGETHER WITH EVIDENCE OF SOME SLIGHT ANEMIA AND LEUKOPENIA, NEUTROPENIA, AND EOSINOPHILIA WERE ENCOUNTERED IN WORKMEN WHO HAD BEEN EXPOSED FOR SEVERAL MONTHS TO CONCN OF 0.76 MG/L. ...SYMPTOMS REGRESSED WHEN EXPOSURE CEASED.

SYMPTOMATOLOGY: 1. BURNING PAIN IN THROAT, ESOPHAGUS, & STOMACH. ... 2. VOMITING...BURNING PAIN, SEVERE PURGING. 3. PULSE...WEAK, IRREGULAR... SOMETIMES IMPERCEPTIBLE. HYPOTENSION &...SIGNS OF CARDIOVASCULAR COLLAPSE APPEAR. 5. ...OLIGURIA, ALBUMINURIA, & HEMATURIA MAY PERSIST FOR WK. /OXALATE/

SYMPTOMATOLOGY: 4. IF DEATH IS DELAYED FOR FEW HR, NERVOUS OR NEUROMUSCULAR SYMPTOMS DEVELOP: HEADACHE, MUSCLE CRAMP (PARTICULARLY OF JAWS & EXTREMITIES), TETANY, SOMETIMES CONVULSIONS, STUPOR, COMA, & DEATH. /OXALATE/

WHILE EVIDENCE FOR TOXICITY...REMAINS OBSCURE, IT WOULD SEEM REASONABLE TO USE STRICT PRECAUTIONS TO AVOID PROLONGED INHALATION OR SKIN CONTACT...

STRONG IRRITANT TO SKIN AND MUCOUS MEMBRANES, ESP BY INGESTION.

Non-Human Toxicity Excerpts · 2 items

DOSES OF 10 ML/KG ON GUINEA PIG SKIN CAUSED NO FATALITIES AND LITTLE IRRITATION.

RAT ORAL LD50 IS 0.4-1.6 G/KG WITH DISTURBANCE OF RESPIRATION AND MUSCLE TWITCHING NOTED AS PROMINENT SYMPTOMS. MASSIVE RENAL OXALATE DEPOSITS AND DILATATION OF TUBULES WERE SEEN AFTER ORAL DOSE OF 400 MG/KG IN RAT.

Probable Routes of Human ExposureNO CASES OF LETHAL POISONING FROM ETHYL OXALATE IN INDUSTRY ARE KNOWN, BUT ITS POTENTIAL TOXIC ACTION MUST BE TAKEN INTO CONSIDERATION.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
RO2800000
ridadr
UN 2525
hs_code
29171900

Chemistry & industry

Pharmacology

Metabolism/MetabolitesETHYL OXALATE IS HYDROLYZED IN BODY TO FORM OXALIC ACID WHICH ACCOUNTS FOR ITS TOXIC ACTION.

Uses & manufacturing

Uses · 6 items

Used to make pharmaceuticals, plastics, dyes, and dyestuff intermediates; Also used as a solvent for cellulose esters, ethers, resins, perfumes, and lacquers for electronics; [HSDB]

Semiconductor Manufacturing [Category: Industry]

MANUFACTURE OF PHENOBARBITAL, ETHYLBENZYL MALONATE, TRIETHYLAMINE, & SIMILAR CHEMICALS; MANUFACTURE OF PLASTICS, DYESTUFF INTERMEDIATES; SOLVENT FOR CELLULOSE ESTERS

ORGANIC SYNTHESES, ESP IN MFR OF PHARMACEUTICALS; SOLVENT FOR ETHERS & RESINS

RADIO TUBE CATHODE FIXING LACQUERS

SOLVENT FOR PERFUMES & FOR NATURAL & SYNTHETIC RESINS (CELLULOSE ESTERS); AGENT IN RADIO TUBE CATHODE FIXING LACQUERS; CHEM INT FOR PHARMACEUTICALS, PLASTICS & DYES

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

(1975) No Data

U.S. Production · 3 items

2023: 70,547 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

Industry UsesSoil amendments (fertilizers)
Methods of Manufacturing · 3 items

ESTERIFICATION OF OXALIC ACID WITH ETHANOL

PREPN: CLARKE, DAVIS, ORG SYN 2, 23 (1922); COLL VOL I, 256; KENYON, COLL VOL I, 258 (P 261 IN 2ND ED).

ETHYL OXALATE IS PRODUCED BY STANDARD ESTERIFICATION PROCEDURE, USING ETHYL ALCOHOL AND OXALIC ACID.

Applications · 3 items

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

UsesDiethyl 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.

General DescriptionEthyl oxalate appears as a colorless liquid. 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.

Preparation methods · 1 item

PreparationAnhydrous oxalic acid and ethanol were esterified in the presence of toluene to produce crude diethyl oxalate. The crude ester was distilled to obtain the finished product. The raw material consumption per ton of product was: 985 kg of oxalic acid, 744 kg of ethanol (95%), and 73.4 kg of toluene.Another preparation method was as follows: Ethanol, benzene, and oxalic acid were added into the reactor and heated to 68 °C for azeotropic reflux dehydration. The reaction endpoint was determined by the cessation of water separation. Benzene was then recovered to yield crude diethyl oxalate, which was distilled under reduced pressure, with the fraction collected at 103 °C / 6 kPa being diethyl oxalate. The product was purified by washing with a dilute sodium carbonate solution, drying over anhydrous potassium carbonate or sodium sulfate, and vacuum distillation.Another preparation method involved adding 45 g (0.5 mol) of anhydrous oxalic acid ①, 81 g (1.76 mol) of anhydrous ethanol, 200 mL of benzene, and 10 mL of concentrated sulfuric acid into a reaction flask equipped with a stirrer and a water separator. The mixture was heated under stirring and refluxed at 68–70 °C for azeotropic dehydration. After most of the water had been evaporated, ethanol and benzene were removed by evaporation. The crude product was washed with water after cooling, then washed with a saturated sodium bicarbonate solution, followed by another water wash, and finally dried with anhydrous sodium sulfate. Diethyl oxalate (57 g) was obtained by atmospheric distillation, with the fraction collected at 182–184 °C, giving a yield of 78%.① Preparation of anhydrous oxalic acid: Oxalic acid was dehydrated with anhydrous chloroform until crystallization occurred, as follows: The mixture was steamed with anhydrous oxalic acid and injected into a powder containing carbon. The product was filtered by suction, dried, and stored in a desiccator for later use. Anhydrous oxalic acid could also be prepared by drying directly in an oven. In this experiment, a corresponding amount of oxalic acid containing water of crystallization could also be used, but the reaction time was longer.

Upstream & downstream products

Downstream products

Ethyl 1-methyl-5-propyl-1H-pyrazole-3-carboxylate5-tert-Butyl-1H-pyrazole-3-carboxylic acid3-Phenyl-1H-pyrazole-5-carboxamide ,97%Ethyl 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylate ,97%5-(3-Chlorophenyl)-1H-pyrazole-3-carboxylic acidEthyl 5-(3-nitrophenyl)-1H-pyrazole-3-carboxylateEthyl 2,4-dioxoheptanoate5-Fluoroindole-2-carboxylic acid3-(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-carboxylateEthyl 5-methylisoxazole-3-carboxylate

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
邹平铭远进出口贸易有限公司18364991597
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Related reactions

1,466 records

Compound notes

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