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Diethyloxalat
ETHYL OXALATE · OXALIC ACID DIETHYL ESTER · DEO · Oxalic ether · iethyl oxalate · Ceftriaxone Impurity 5 · GKSW · oxalicether
Identifikatoren & physikalische Daten
| CAS No. | 95-92-1 |
|---|---|
| Summenformel | C6H10O4 |
| Durchschnittliche Molmasse | 146,14 g/mol |
| Monoisotopische Masse | 146,0579088 g/mol |
| SMILES | CCOC(=O)C(=O)OCC |
| InChIKey | WYACBZDAHNBPPB-UHFFFAOYSA-N |
| PubChem CID | 7268 |
| ChEMBL | CHEMBL3183226 |
| EC No. | 202-464-1 |
| DTXSID | DTXSID2044472 |
| Lokaler Name | Diethyloxalat |
Chemische & physikalische Eigenschaften
| XLogP | 0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 114 |
| Stoffklassen | Other Classes -> Esters, OtherFlammable agents - 2nd degree |
| Kosmetika | ChelatingPlasticiserHair conditioning |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | 0.56 |
| Geruch | AROMATIC ODOR |
| Lebensmittelzusatzstoffe | Food |
| Dichte | 1.0785 @ 20 °C/4 °C1.079 @ 20°C1.076 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | COLORLESS, OILY LIQUID |
| Löslichkeit | SPARINGLY SOL IN WATER WHICH DECOMP IT GRADUALLYMISCIBLE WITH USUAL ORG SOLVENTSSOL IN ALL PROPORTIONS IN ALCOHOL, ETHER, ACETONEMISCIBLE WITH ETHYL ACETATEMiscible with alcohols, ether and other common organic solvents.MAY DECOMPOSE |
| Flammpunkt | 168 °F (NFPA, 2010)168 °F CC |
| Siedepunkt | 185.7 °C @ 760 MM HG185.4 °C @760 [mm Hg]185 °C (lit.) |
| Schmelzpunkt | -41 °C (lit.) |
| Dampfdichte | 5.03 (vs air) |
| Dampfdruck | 1 mm Hg ( 47 °C) |
| Brechungsindex | n20/D 1.410(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear |
| Explosionsgrenze | 0.42-2.67%(V) |
| Merck | 14,3125 |
| BRN | 606350 |
| Henry-Konstante | 4.5×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 8.2(21℃) |
| Stabilität | Stable, but moisture sensitive. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | CHELATINGPLASTICISERFRAGRANCEHAIR CONDITIONINGSOLVENT |
| InChI | 1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3 |
| InChIKey | WYACBZDAHNBPPB-UHFFFAOYSA-N |
| SMILES | CCOC(=O)C(=O)OCC |
| LogP (Verteilungskoeffizient) | 0.560 |
| CAS Datenbank | 95-92-1(CAS DataBase Reference) |
| NIST chemische Informationen | Ethanedioic acid, diethyl ester(95-92-1) |
| EPA chemische Informationen | Ethyl oxalate (95-92-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: 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)DangerH302 (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) |
|---|---|
| Regulatorische Informationen | Chemical: Ethanedioic acid, diethyl esterCommission 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/14261Diethyl oxalate: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Oxalate esters (C1-C4): Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· Combustible material: may burn but does not ignite readily. |
| Brandpotenzial | MODERATE WHEN EXPOSED TO HEAT OR FLAMETHIS 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. |
| Gesundheitsgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| Gefahrenübersicht | A strong skin and mucous membrane irritant[Hawley] An eye irritant[eChemPortal: ERMAESIS] An irritant[MSDSonline] |
| DOT-Nummer und Handbuch | 2525 156 |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Reactivity Profile | ETHYL 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 |
| DOT Emergency Guidelines | /GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire or Explosion: 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./GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Health: TOXICinhalation, 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 which 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./GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas./GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLYit is not effective in spill situations where direct contact with the substance is possible.For more DOT Emergency Guidelines (Complete) data for DIETHYL OXALATE (8 total), please visit the HSDB record page. |
| DOT Hazard Classification | Ethyl oxalateUN2525Div 6.1 Poisonous materials (49 eCFR § 173.132)PG III: the degree of danger presented by the material is minor |
| Brandbekämpfung | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:General First Aid: |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | FOAM, CARBON DIOXIDE, DRY CHEMICAL |
| Lagerbedingungen | 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/ |
| Freisetung ohne Brand | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: |
| Preventive Measures | ...PROVISION SHOULD BE MADE FOR REMOVAL OF VAPORS AS THEY ARE EVOLVED &...HEATING SHOULD NOT BE SUCH AS TO EXPOSE VAPOR TO OPEN FLAME. /ESTERS/BEFORE HEAT (EG IN FORM OF WELDING OR CUTTING FLAME) IS USED TO CUT OR REPAIR A VESSEL THAT HAS CONTAINED ORGANIC ESTER, ANY SLUDGE...MUST BE REMOVED & VESSEL PURGED WITH STEAM TO INSURE THAT EXPLOSIVE CONCN OF VAPOR WILL NOT FORM IN COURSE OF WORK. /ESTERS/ATMOSPHERE SHOULD BE TESTED FOR PRESENCE OF FLAMMABLE VAPOR & ONLY WHEN TESTING ESTABLISHES THAT VESSEL IS SAFE SHOULD HEAT BE APPLIED. /ESTERS/ |
| Isolation and Evacuation | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Immediate precautionary measure |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:EYE & FACE PROTECTION & RESPIRATORY PROTECTIVE EQUIPMENT SHOULD BE AVAILABLE...IN CASE OF EXPOSURE TO THESE ESTERS IN EMERGENCIES ASSOC, FOR EXAMPLE, WITH SERIOUS ESCAPE OF LIQUID. /ESTERS/ |
| Emergency Response Planning Guidelines | · Note: Most foams will react with the material and release corrosive/toxic gases. |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Human Toxicity Excerpts | ...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 | 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 Exposure | NO CASES OF LETHAL POISONING FROM ETHYL OXALATE IN INDUSTRY ARE KNOWN, BUT ITS POTENTIAL TOXIC ACTION MUST BE TAKEN INTO CONSIDERATION. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2525 |
| Zollcode | 29171900 |
| RTECS-Nr. | RO2800000 |
| R-Sätze (R) | 22-36-68/21-48/25-35-61-60 |
| Toxizität | LD50 orally in Rabbit: 400 mg/kg |
| Gefahrensymbole | Xn,T |
| Sicherheitshinweise (S) | 23-45-36/37/39-28-26-25-24-53 |
| Gefahrenklasse | 6.1Acute Tox. 4 OralEye Dam. 1Skin Corr. 1BSTOT RE 2 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 95-92-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 410 °C |
Anwendungen & Verwendung
Verwenden
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.