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Home > Encyclopedia > 2-Cyanoethyl acrylate

2-Cyanoethyl acrylate

2-Cyanoethyl acrylate structure

2-Cyanoethyl acrylate 

structure
  • CAS No:

    106-71-8

  • Formula:

    C6H7NO2

  • Chemical Name:

    2-Cyanoethyl acrylate

  • Synonyms:

    2-Propenoic acid,2-cyanoethyl ester;Acrylic acid,ester with hydracrylonitrile;Hydracrylonitrile,acrylate (ester);2-Cyanoethyl acrylate;2-Cyanoethyl propenoate;NSC 18593;2-Cyanoethyl prop-2-enoate

2-Cyanoethyl acrylate Basic Attributes

125.12500

125.13

203-426-7

3ICU1C15OY

18593

DTXSID1044776

Liquid

2926909090

Characteristics

50.09000

0.62928

2.069 g/cm3

-16.9ºC

108 °C @ Press: 12 Torr

124 °C

1.436

Soluble in water

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products. ... The acrylic esters may be stored in mild or stainless steel, or aluminum. /Acrylic acid & derivatives/

0.0585mmHg at 25°C

4.3 (AIR= 1)

Polymerizes when heated|React readily with electrophilic, free-radical, and nucleophilic agents /Acrylic acid & esters/

2-Cyanoethyl acrylate|C*: Compounds that autopolymerize due to peroxide formation if inhibitors are depleated or not present|PubChem|Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. 1(78) 349

Safety Information

II

8

3276

20/21/22-36/37/38

S26-S36/37/39

AT1500000

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

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.

|Danger|H301 (13.33%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 15 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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/|Protection required for safe handling of acrylic acid and esters commonly includes use of impervious gloves, shoe soles, and clothing; splash-proof goggles ... /Acrylic acid & derivatives/

A fire hazard when exposed to heat or flame.

Water or foam may cause frothing ....

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.

THE LOWER-MOL-WT ESTERS OF ACRYLIC ACIDS ARE IRRITANTS TO SKIN, EYES, & MUCOUS MEMBRANES. /ACRYLIC ACID ESTERS/|A skin and eye irritant.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Toxicity

LD50 Rat oral 180 mg/kg|LD50 Rabbit skin 220 ul/kg

Drug Information

Basic treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures 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 ... . /Irritating materials/|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 if 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 ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/

Three cases of contact dermatitis, due to exposure to ethyl cyanoacrylate (ECA) containing glue, in women aged 42, 23, and 48 years were described. The patients presented with complaints of a pruritic eczematous eruption on the hands. The lesions were concentrated primarily around the periungual folds and fingertips. In the 48 year old, patient the hand dermatitis was associated with chronic eyelid dermatitis. The 23 and 48 year old patients had been undergoing nail wrapping for about 6 months. The 42 year old patient was a manicurist who specialized in nail wrapping. Patch testing with the International Contact Dermatitis Research Group (ICDRG) standard battery and a resin of toluene-sulfonamide and formaldehyde was performed. All patients were negative to the resin and the 42 and 23 year old patients gave negative responses to the entire ICDRG battery. The 48 year old patient was negative to the ICDRG battery except for 0.5 percent diaminodiphenylmethane in petrolatum. The patients were patch tested with Krazy Glue, an acrylate based glue used in nail wrapping. All three gave moderate to strong positive responses. Their dermatitis cleared when they avoided contact with Krazy Glue. Analytical data supplied by the manufacturer showed that Krazy Glue contains 99.95 percent ECA and 0.05 percent undefined acrylic contaminants. The product had not induced any allergic reactions in animal studies. The author suggests that ECA is the allergen responsible for the patients' dermatitis, and that the localization of the rash to the hands suggests that the dermatitis originates from direct contact with ECA rather than from systemic absorption. He also suggests that dermatologists in areas where nail wrapping is popular should be on the alert for patients with possible cyanoacrylate allergies.|THE ACUTE TOXICITY OF THE ACRYLATES DECREASES WITH INCREASING MOLECULAR WEIGHT. ... HUMAN SIGNS & SYMPTOMS FOLLOWING INGESTION OF ACRYLIC MONOMERS INCL COLLAPSE, SEVERE RESPIRATORY DIFFICULTIES, & CNS STIMULATION. ACUTE INHALATION OF HIGHER CONCN MAY CAUSE MARKED IRRITATION, SALIVATION, CONJUNCTIVAL IRRITATION, & PRONOUNCED PULMONARY IRRITATION OR EDEMA. PROLONGED SKIN OR EYE CONTACT MAY RESULT IN SEVERE TISSUE DAMAGE. THE PATHOLOGY FROM SINGLE EXPOSURE IS CONTRARY TO REPEATED EXPOSURE EFFECTS, WHICH INCL PULMONARY CONGESTION OR HEMORRHAGE & CLOUDY SWELLING OF LIVER & KIDNEY. /ACRYLATES/

2-Cyanoethyl acrylate Use and Manufacturing

Methods of Manufacturing

Sodium cyanide + ethylene oxide + acrylic acid (epoxidation/esterification)|In ... propylene oxidation process acrolein is first formed by the catalytic oxidation of propylene vapor at high temp in the presence of steam. The acrolein is then oxidized to acrylic acid. ... The acrylic acid is esterified with alcohol to the ... acrylic ester in a separate process. /Acrylic ester monomers/

Uses

Forms polymers and copolymers for viscosity index improvers; adhesives; textile finishes & sizes.

Production

(1977) AT LEAST 4.54X10+6 G|(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

... Hydroquinone or monomethyl ether hydroquinone are added to acrylic monomers to stabilize them .... /Acrylic ester monomers/

2-Propenoic acid, 2-cyanoethyl ester: ACTIVE

Chemical assay is preferably performed by gas-liquid chromatography or by the conventional methods for determination of unsaturation such as bromination or addition of mercaptan, sodium bisulfide, morpholine, or mercuric acetate. /Acrylic acid & derivatives/|RETENTION TIMES FOR ACRYLATES WERE MEASURED WITH 2 DIFFERENT COLUMNS (C18 CORASIL & C8 LICHROSORB) USING REVERSE-PHASE HIGH PRESSURE LIQ CHROMATOGRAPHY IN ORDER TO OBTAIN THE PARTITION COEFFICIENTS OF ACRYLATES BETWEEN 1-OCTANOL AND WATER (LOG P). /ACRYLATES/

Computed Properties

Molecular Weight:125.13
XLogP3:0.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:125.047678466
Monoisotopic Mass:125.047678466
Topological Polar Surface Area:50.1
Heavy Atom Count:9
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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