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Home > Encyclopedia > Methacrylic anhydride

Methacrylic anhydride

Methacrylic anhydride structure

Methacrylic anhydride 

structure
  • CAS No:

    760-93-0

  • Formula:

    C8H10O3

  • Chemical Name:

    Methacrylic anhydride

  • Synonyms:

    2-Propenoic acid,2-methyl-,1,1′-anhydride;Methacrylic anhydride;2-Propenoic acid,2-methyl-,anhydride;Methacrylic acid anhydride;Methacryloyl anhydride;NSC 24159;Bis(methacrylic acid) anhydride;Dimethacrylic acid anhydride;Norsocryl 500;2-Methylprop-2-enoyl 2-methylprop-2-enoate;1801647-10-8;2055573-68-5

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

liquid


Methacrylic anhydride is a liquid. (EPA, 1998)|Liquid


Methacrylic anhydride is a liquid. (EPA, 1998)

Methacrylic anhydride Basic Attributes

154.165

154.16

212-084-8

N2RJR03340

24159

3265|2531

2916190090

Characteristics

43.4

1.82

Methacrylic anhydride is a liquid. (EPA, 1998)

1.035 g/cm3

-20°C

89 °C @ Press: 5 Torr

84.4±0.0 °C

1.443

> 10% in ethanol

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products.

Reacts exothermically with water to form methacrylic acid.

Hydrocarbons, Aliphatic Unsaturated

Water-Reactive

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.

Safety Information

II

8

UN 3265 8/PG 2

1

R20;R37/38;R41

S26-S39

OZ5700000

Xn:Harmful;

Stable. Flammable. Moisture-sensitive.

P261-P280-P301 + P312 + P330-P305 + P351 + P338 + P310

H302 + H332-H315-H317-H318-H335

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.

(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)

|Danger|H302 (40.54%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P330, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 79 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

(Non-Specific -- Methacrylic Acid) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. (Non-Specific -- Methacrylic Acid) This material may react violently with water. Small fires: dry chemical, carbon dioxide, water spray, or foam. Large fires: water spray, fog, or foam. Move container from fire area if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. (EPA, 1998)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(Non-Specific -- Methacrylic Acid) Do not touch spilled material; stop 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)

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/

... 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.

Methacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/

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.

Toxicity

LC50 Mouse ihl 450 mg/cu m/2 hr

Drug Information

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

Note: No information on specific clinical effects of exposure was available. Signs and Symptoms of Methacrylic Anhydride Exposure: Signs and symptoms of acute exposure to methacrylic anhydride may include headache, dizziness, weakness, and nausea. May cause irritation of the eyes, skin, and respiratory tract. Esophageal or gastrointestinal tract irritation or burns may also be noted. Emergency Life-Support Procedures: Acute exposure to methacrylic anhydride may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to methacrylic anhydride. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to methacrylic anhydride. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. DO NOT induce vomiting or attempt to neutralize! 4. Transport to a health care facility. (EPA, 1998)

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/

Methacrylic anhydride Use and Manufacturing

Uses

Intermediates

Production

25,000 - 100,000 lb

All other basic organic chemical manufacturing|2-Propenoic acid, 2-methyl-, 1,1'-anhydride: ACTIVE|METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

Thin-layer chromatography (TLC), polarography, and spectrometry are used for soln measurements. Methacrylates in air have been analyzed by TLC, polarography, and colorimetry. Polarography has been used for determination of any residual monomer in the polymer. /Methacrylic acid & derivatives/

Computed Properties

Molecular Weight:154.16
XLogP3:1.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:154.062994177
Monoisotopic Mass:154.062994177
Topological Polar Surface Area:43.4
Heavy Atom Count:11
Complexity:202
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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