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Methacrylsureanhydrid
1-Methylacrylic anhydride · Methacrylic acid anhydride · METHACRYLIC ANHTDRIDE · methacrylicacidanhydride · 2-methyl-2-propenoicacianhydride · 2-METHYL-2-PROPENOIC ACID ANHYDRIDE · 2-Propenoic acid, 2-methyl-, anhydride · 276685-500ML
Identifikatoren & physikalische Daten
| CAS No. | 760-93-0 |
|---|---|
| Summenformel | C8H10O3 |
| Durchschnittliche Molmasse | 154,16 g/mol |
| Monoisotopische Masse | 154,06299418 g/mol |
| SMILES | C=C(C)C(=O)OC(=O)C(=C)C |
| InChIKey | DCUFMVPCXCSVNP-UHFFFAOYSA-N |
| PubChem CID | 12974 |
| EC No. | 212-084-8 |
| DTXSID | DTXSID60862404 |
| Lokaler Name | Methacrylsureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 201 |
| Stoffklassen | Other Classes -> Acid Anhydrides, Other |
| SpringerMaterials Properties | Optical coefficient |
| Dichte | Specific gravity: 1.0351.035 @25 °C1.04 g/mL at 20 °C |
| Viscosity | 3 mPa |
| Löslichkeit | > 10% in ether> 10% in ethanolMiscible with ethanol and ether.98g/L at 20℃ |
| Siedepunkt | 192 °F at 5 mmHg (EPA, 1998)89 °C at 5 mm Hg240 °C @760 [mm Hg]87 °C13 mm Hg(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Dampfdruck | 8.83 [mmHg]0.01 [mm Hg] @25 °C90Pa at 20℃ |
| Brechungsindex | Index of refraction: 1.4540 @ 20 °CIndex of refraction: 1.453 at 25 °C/Dn20/D 1.453(lit.) |
| Physical Description | Methacrylic anhydride is a liquid. (EPA, 1998)[CAMEO] Colorless liquid[MSDSonline] |
| Schmelzpunkt | -20°C |
| Flammpunkt | 184 °F |
| Lagerbedingungen | under inert gas (nitrogen or Argon) at 2-8°C |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Light yellow to Light orange |
| BRN | 1761982 |
| Stabilität | Stable. Flammable. Moisture-sensitive. |
| InChI | 1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3 |
| InChIKey | DCUFMVPCXCSVNP-UHFFFAOYSA-N |
| SMILES | CC(=C)C(=O)OC(=O)C(C)=C |
| LogP (Verteilungskoeffizient) | 1.23 |
| CAS Datenbank | 760-93-0(CAS DataBase Reference) |
| NIST chemische Informationen | Methacrylic anhydride(760-93-0) |
| EPA chemische Informationen | Methacrylic anhydride (760-93-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.7% (5 of 184) of reports.DangerH302+H332 (57.6%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation]P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 184 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | 2-Propenoic acid, 2-methyl-, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 1,1'-anhydride 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: 28-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/52772-Propenoic acid, 2-methyl-, anhydride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.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.) |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | (Non-Specific -- Methacrylic Acid) This material may burn but may not ignite readily. Flammable/ poisonous gases may accumulate in tanks and hopper cars. Some of these materials may ignite combustibles (wood, paper, oil, etc.). (EPA, 1998) |
| Gesundheitsgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Gefahrenübersicht | Reacts with water exothermically producing methacrylic acid[CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitisMay cause skin sensitization[MSDSonline] |
| Reaktive Gruppe | Hydrocarbons, Aliphatic Unsaturated |
| Reactivity Alerts | Water-Reactive |
| Reactivity Profile | METHACRYLIC ANHYDRIDE reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. |
| Air and Water Reactions | Reacts exothermically with water to form methacrylic acid. |
| CERCLA-Meldepflichtmengen | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methacrylic anhydride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs. |
| Hazard Classes and Categories | Acute Tox. 4 (71.7%) |
| Skin, Eye, and Respiratory Irritations | Methacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/ |
| Brandbekämpfung | (Non-Specific -- Methacrylic Acid) Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. |
| Erste Hilfe | Note: No information on specific clinical effects of exposure was available. |
| Lagerbedingungen | Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/ |
| Freisetung ohne Brand | (Non-Specific -- Methacrylic Acid) Do not touch spilled materialstop leak if you can do so without risk. For small spills, absorb with sand or other noncombustible absorbent material and place into containers for later disposal. For large spills, dike far ahead of spill for later disposal. (EPA, 1998) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Preventive Measures | ... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Protective Action Criteria (PAC) | 0.41 [mg/m3]4.5 [mg/m3]16 [mg/m3] |
| Personal Protective Equipment (PPE) | For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/ |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Antidote and Emergency Treatment | Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at lO to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/ |
| Toxicity Data | LC50 (mice) = 450 mg/m3/2h |
| Non-Human Toxicity Values | LC50 Mouse ihl 450 mg/cu m/2 hr |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3265 8/PG 2 |
| Zollcode | 29161900 |
| RTECS-Nr. | OZ5700000 |
| R-Sätze (R) | 20-37/38-41 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-39 |
| Gefahrenklasse | 8Acute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 760-93-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Methacrylic anhydride is a reactive monomer used primarily as a monomer in the preparation of polymers, particularly poly(methacrylic acid) and its copolymers. The reaction mechanism involves the formation of covalent bonds between methacrylic acid and acetic anhydride molecules, resulting in the formation of a novel compound. The newly formed compound then undergoes a series of reactions including hydrolysis and polymerisation. Methacrylic anhydride produces polymers with good chemical and thermal stability, which are used in a wide range of applications in various industries such as bio-renewable resins, pH-sensitive hydrogels, thermoset plastics, coatings, adhesives and plastics.
Verwenden
Methacrylic anhydride is a reactive monomer used for the preparation of different type of monomers under mild reaction conditions. It finds applications in light-curing coatings, cross-linked materials like synthetic resin. It acts as an intermediate for the preparation of fibers and resins.
Herstellung & Synthese
synthetische
To synthesize Methacrylic anhydride, sodium methacrylate (1 mol), propionyl chloride (3 mol), and a polymerization inhibitor (0.1 mol) were added to a reaction kettle. The mixture was heated to 90-100 ℃ and refluxed for 8 hours. Methacrylic anhydride was then obtained by distilling and collecting fractions at 100-105 ℃. The yield of the product was 98.33%.