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Home > Encyclopedia > Methyl cyanoacrylate

Methyl cyanoacrylate

Methyl cyanoacrylate structure

Methyl cyanoacrylate 

structure
  • CAS No:

    137-05-3

  • Formula:

    C5H5NO2

  • Chemical Name:

    Methyl cyanoacrylate

  • Synonyms:

    2-Propenoic acid,2-cyano-,methyl ester;Acrylic acid,2-cyano-,methyl ester;ADhere;α-Cyanoacrylic acid methyl ester;Eastman 910;Methyl α-cyanoacrylate;Methyl 2-cyanoacrylate;Mecrylate;Methyl cyanoacrylate;2-Cyanoacrylic acid methyl ester;Mecrilat;Cyanobond SS;Cemedine 3000;Cemedine 3000 Type-II;CA 7 (adhesive);CA 7;Cemedine 3000DX;Sicomet 7000;Mecrilate;Fimofix P 1048;Cyanobond 5000;Three Bond 1701;Eastman 910 Super Glue;Wipescar;118232-59-0;12790-65-7;53028-65-2

Description

Colorless liquid with a characteristic odor.


Methyl 2-cyanoacrylate is a clear slightly yellow liquid. (NTP, 1992)|COLOURLESS LIQUID.|Clear to slightly yellow liquid with a characteristic odor.|Colorless liquid with a characteristic odor.


Methyl 2-cyanoacrylate is a clear slightly yellow liquid. (NTP, 1992)

Methyl cyanoacrylate Basic Attributes

111.09900

111.10

205-275-2

WN7979561R

1272

1993

DTXSID4025589

Clear, colorless liquid|Thick liquid

2926909090

Characteristics

50.09000

0.23918

Methyl 2-cyanoacrylate is a clear slightly yellow liquid. (NTP, 1992)

1.1044 g/cm3 @ Temp: 27 °C

-40 °C

47-49 °C @ Press: 1.8 Torr

67.6ºC

1.428

30%

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/

(77°F): 0.2 mmHg

Relative vapour density (air = 1): 3.8

Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

Strong, acrid odor

Specific gravity: 1.1044 at 20 °C/25 °C|Contact with moisture causes rapid polymerization|React readily with electrophilic, free-radical, and nucleophilic agent /Acrylic acid & esters/|Hydroxyl radical reaction rate constant = 3.1X10-12 cu cm/molecule-sec at 25 °C (est)

Insoluble in water.

Nitriles

Polymerizable

METHYL 2-CYANOACRYLATE is an unsaturated aliphatic nitrile and acrylate ester. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. 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.

Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

Safety Information

1993

R36/37/38

S23;S26;S24/25

AS7000000

Xi

Separated from incompatible materials. See Chemical Dangers. Well closed. Store only if stabilized.

Liquid /dries/ within 15-45 seconds without aid of catalysts, heat, or solvent evaporation.

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

H315

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Moisture (Note: Contact with moisture causes rapid polymerization).

WHO; Concise International Chemical Assessment Document 36, Methyl Cyanoacrylate and Ethyl Cyanoacrylate (2001). CICADs are concise documents that provide summaries of the relevant scientific information concerning the potential effects of chemicals upon human health and/or the environment. The primary objective of CICADs is characterization of hazard and dose-response from exposure to a chemical.[Available from, as of February 15, 2011: http://www.inchem.org/documents/cicads/cicads/cicad36.htm]

Flash point data for this compound are not available but it is probably non-flammable. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree, Reactive - 1st degree

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 183 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P271, P280, P284, P304+P340, P305+P351+P338, P310, P312, P320, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P260, P261, P264, P270, P271, P280, P284, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P337+P313, P342+P311, P362, P370+P378, P403+P233, P403+P235, P405, and P501

Fires involving this compound should be controlled using a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)|Use foam, powder, carbon dioxide. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). 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)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then use absorbent paper to pick up liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do no reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should wash daily at the end of each work shift. Remove: No recommendation is made specifying the need for removing clothing that becomes wet or contaminated. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|(See protection codes)

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/|The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|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. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

A human eye irritant. NOAEL for irritancy due to MCA vapor of 1 ppm (4.5 mg/cu m). Eye irritation ... noticed @ 5 ppm, & 20 ppm causes lacrimation & rhinorrhea.

Vacated 1989 OSHA PEL TWA 2 ppm (8 mg/cu m); STEL 4 ppm (16 mg/cu m) is still enforced in some states.

Recommended Exposure Limit: 10 hr Time-Weighted avg: 2 ppm (8 mg/cu m).|Recommended Exposure Limit: 15 min Short-Term Exposure Limit: 4 ppm (16 mg/cu m).

Personal protection: face shield and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Remove all ignition sources. Do NOT wash away into sewer. Absorb liquid in sand or inert absorbent. Let solidify.

Separated from incompatible materials. See Chemical Dangers. Well closed. Store only if stabilized.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

The vapour is irritating to the eyes and respiratory tract. Inhalation of the vapour may cause asthmatic reactions. Immediately glues (sticks to) biological tissues.

Repeated or prolonged contact with skin may cause dermatitis.

NO open flames. Above 79 °C use a closed system and ventilation.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Toxicity

LD50 Rat oral 1.6-3.2 g/kg|LD50 Guinea pigs dermal > 10 mL/kg|LC50 Rat inhalation 101 ppm/6 hr

Methyl 2-cyanoacrylate's production and use as an adhesive(1,2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.7(SRC), determined from a structure estimation method(2), indicates that methyl 2-cyanoacrylate is expected to have very high mobility in soil(SRC). However, movement of methyl 2-cyanoacrylate through soil will be hindered by its rapid polymerization as it comes into contact with moisture or other weakly basic substances(3-5). Since methyl 2-cyanoacrylate polymerizes rapidly on contact with moisture, volatilization from moist soil surfaces is not a relevant environmental process for this substance. Methyl 2-cyanoacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.2 mm Hg at 25 °C(3). Biodegradation is not an important environmental fate proces due to rapid polymerization(3-5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.7(SRC), determined from a structure estimation method(2), indicates that methyl 2-cyanoacrylate is not expected to adsorb to suspended solids and sediment(SRC). However, methyl 2-cyanoacrylate polymerizes rapidly on contact with moisture or other weakly basic substances(3-5). Therefore, environmental processes such as volatilization from water surfaces and bioconcentration in aquatic organisms are not relevant for this substance(SRC). Biodegradation is not an important environmental fate proces due to rapid polymerization(3-5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl 2-cyanoacrylate, which has a vapor pressure of 0.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl 2-cyanoacrylate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.2 days(SRC), calculated from its rate constant of 3.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Methyl 2-cyanoacrylate contains chromophores that absorb strongly at wavelengths >290 nm, and therefore may be susceptible to direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of methyl 2-cyanoacrylate with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The 2-cyanoacrylic esters are highly reactive and polymerize nearly instantaneously through an anionic mechanism on contact with moisture or other weakly basic substances (2,3,4). Therefore, rapid polymerization is expected to be the dominant fate process for methyl 2-cyanoacrylate in soil and water. Methyl 2-cyanoacrylate contains chromophores that absorb strongly at wavelengths >290 nm, and therefore may be susceptible to direct photolysis by sunlight(5).

Methyl 2-cyanoacrylate polymerizes rapidly on contact with moisture(1,2,3). Therefore, bioconcentration in aquatic organisms is not a relevant environmental process for this substance(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of methyl 2-cyanoacrylate can be estimated to be 3.7(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl 2-cyanoacrylate is expected to have very high mobility in soil. However, movement of methyl 2-cyanoacrylate through soil will be hindered by its rapid polymerization as it comes into contact with moisture or other weakly basic substances(3-5).

Methyl 2-cyanoacrylate polymerizes rapidly on contact with moisture (1-3). Therefore, volatilization from moist soil and water surfaces is not a relevant transport process for this substance(SRC). Methyl 2-cyanoacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.2 mm Hg at 25 °C(1).

... /IN/ SIMULATED WORKBENCH EXPOSURE ... VAPOR LEVELS RANGED FROM ABOUT 1 PPM TO 60 PPM.|Those engaged in the mfr of this material and its formulation and application into quick-setting, high-strength adhesive cements.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 51,367 workers (22,918 of these were female) were potentially exposed to methyl 2-cyanoacrylate in the US(1). Occupational exposure to methyl 2-cyanoacrylate may occur through inhalation and dermal contact with this compound at workplaces where methyl 2-cyanoacrylate is produced or used. Members of the general population may be exposed to methyl 2-cyanoacrylate via inhalation or dermal contact when using commercial cyanoacrylate adhesives(SRC).

Drug Information

Methyl-2-cyanoacrylate, a widely used material for coating cerebral aneurysm, was recently withdrawn.|Tissue Adhesives|Cyanoacrylate has been used in medicine and dentistry for many years. It has been used as a postextraction dressing and retrograde filling material in endodontic surgery. /Cyanoacrylate/|Glues based on cyanoacrylates are widely used as contact adhesives for metal, glass, rubber, plastics and textiles, as well for biological materials, including binding tissues and sealing wounds in surgery. /Cyanoacrylates/|For more Therapeutic Uses (Complete) data for METHYL 2-CYANOACRYLATE (8 total), please visit the HSDB record page.

Methyl-2-cyanoacrylate, a widely used material for coating cerebral aneurysm, was recently withdrawn.|A 61-year-old woman developed fever, neck stiffness, and cerebrospinal fluid eosinophilia after an operation for an intracranial aneurysm. ... To detect the cause of this disorder, ... 2-day closed patch testing /was done/ with the substances thought to be possible allergens. ... A positive reaction to methyl-2-cyanoacrylate, the main ingredient of Biobond, the tissue adhesive used in the surgery /was recorded/. This substance could have caused postoperative allergic meningitis.|Skin, eye or mouth contact may result in almost immediate tissue-to-tissue bonding. To pull or pry adherent skin surfaces apart commonly causes evulsion of epidermis.|In the absence of tissue-to-tissue bonding, do not attempt to peel off the adhesive; sweat or other secretions will eventually accumulate under the adhesive film and cause it to lift off.|Use of excessive quantities appears to retard healing and increases probabilities of adhesions.

Substances used to cause adherence of tissue to tissue or tissue to non-tissue surfaces, as for prostheses. (See all compounds classified as Tissue Adhesives.)

Following oral administration of 0.05 mL liquid beta-(14)C-methyl cyanoacrylate (MCA) (as monomer and polymer) to groups of two rats, radioactivity was detected in the urine, indicating that some absorption had occurred. For the rats receiving liquid MCA monomer into the oral cavity by syringe, approximately 2% of the radiolabel administered was recovered in urine over 48 hr. For rats receiving poly-MCA directly into the stomach, the total mean recovery from urine samples after 4 days was approximately 16%. A mean total of 18% of the radiolabel administered was recovered from feces on completion of the 4-day sampling period. However, the detection of radiolabel in the stool samples may well reflect the passage of poly-MCA particles directly through the gastrointestinal tract rather than any absorption and metabolism.|Following dermal application of 0.5 mL liquid liquid beta-(14)C-methyl cyanoacrylate (MCA) to groups of two rats, radioactivity was detected in the urine, indicating limited dermal absorption (up to 4% of the applied dose over a 6-day collection period). When the liquid was applied to skin with the epidermis removed, the amount of radiolabel recovered from urine increased approximately 3-fold.|Methyl 2-cyanoacrylate was rapidly absorbed from the skin incision site & eliminated in the urine in guinea pigs. Initial metabolites possessed the carbon skeleton of the monomer, whereas metabolites excreted from day 2 onward represented absorbed & degraded polymeric material.|The alkyl /cyanoacrylate/ esters can be absorbed through skin, with the methyl showing the highest rate of urine excretion, 12% of cmpd being excreted in five days when originally applied to rat skin.

Following sc implantation of (14)C-labeled methyl 2-cyanoacrylate into dogs radioactive urea was found in the urine. Hypothesis: hydrolytic chain scission & ester hydrolysis may be involved in in vivo degradation of cyanoacrylate tissue adhesives.

Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, nose; blurred vision, lacrimation (discharge of tears); rhinitis Target Organs: Eyes, skin, respiratory system (NIOSH, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 0.9% saline (NS) 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ There is one ... study available in which odor perception and sensory irritation were investigated in humans exposed to methyl cyanoacrylate (MCA) vapor. The study involved the use of an exposure chamber; however, due to the difficulties in generating MCA exposure atmospheres, exposure was achieved via a simulated work procedure in which the subjects applied the adhesive to microscope slides or other glass sheets. ... The operations were graduated so as to produce vapor concentrations ranging from 1 to 60 ppm (4.5 to 272 mg/cu m). Air samples were taken in the breathing zone of each individual with sampling periods of 5 min, and collection was repeated 10 times/hr for the duration of the study. ... Subjects filled in a questionnaire at the end of each 5-min sampling period to indicate odor perception and irritancy responses. In preliminary trials marked eye and nose irritation were reported at 40 to 60 ppm (182-272 mg/cu m). For two individuals, blurred vision was reported some time after the exposure and persisted for approximately 2 hr. Fourteen individuals participated in the main study, with some performing the simulated occupational tasks more than once; adhesives were applied dropwise onto glass slides using a syringe or directly from the adhesive container. These procedures are a closer simulation of many of the occupational uses of the cyanoacrylate adhesives than was the preliminary study. ... No effects were reported in any of the 14 subjects at 1 ppm (4.5 mg/cu m). The odor threshold was reported to be 1 to 5 ppm (4.5 to 23 mg/cu m). Throat and nose "irritation" were subjectively reported from 2 to 20 ppm (9.1 to 91 mg/cu m) or more, although the severity was unclear (at 2 ppm [9.1 mg/cu m], ...no more than 3 of the 14 people reported effects). Eye irritation and "burning" were reported from 4 to 15 ppm (18 to 68 mg/cu m) or more, although ... it is impossible to tell exactly what proportion of volunteers reported effects. At concentrations above 20 ppm (91 mg/cu m), lacrimation and rhinorrhea were reported (except for one individual in whom rhinorrhea was reported at around 7 ppm [32 mg/cu m]), and these were more pronounced at 50 to 60 ppm (227-272 mg/cu m) (a level at which painful eye irritation was also reported). The study report suffers from a number of limitations. ... Despite these limitations, it is possible to identify a NOAEL for irritancy due to MCA vapor of 1 ppm (4.5 mg/cu m) from this study. At around 2 ppm (9.1 mg/cu m), the nasal and throat effects were of unclear severity in no more than 3 of the 14 volunteers, with marked effects (rhinorrhea and lacrimation) at around 20 ppm (91 mg/cu m) or more.|/HUMAN EXPOSURE STUDIES/ Vapor exposure of normal volunteers to /cyanoacrylate/ methyl ester ... @ 40-60 ppm in air ... is very objectionable, producing irritation of the eyes and nose, & "blurred vision" which was noted by two volunteers ... 2 hr after exposure. At lower concn, ... eye irritation ... noticed @ 5 ppm, & 20 ppm causes lacrimation & rhinorrhea.|/SIGNS AND SYMPTOMS/ Accidentally, cyanoacrylate glues that are in common household use have been applied to the eye mistakenly as eyedrops, causing immediate brief smarting, and firm gluing of the lids together. ... In the common accidental dropping of the glue on the eye or similar splashing, the glue may cause transient punctate epithelial keratopathy, but as a rule it does not adhere to the cornea or conjunctiva. /Cyanoacrylate glues/|/SIGNS AND SYMPTOMS/ An outbreak of irritant dermatitis among electronic assembly workers was caused by the vaporization of a monomer under conditions of low relative humidity. /n-alkyl-alhpa-cyanoacrylates/|For more Human Toxicity Excerpts (Complete) data for METHYL 2-CYANOACRYLATE (13 total), please visit the HSDB record page.

methyl 2-cyanoacrylate

The substance can be absorbed into the body by inhalation of its vapour.|inhalation, ingestion, skin and/or eye contact

irritation eyes, skin, nose; blurred vision, lacrimation (discharge of tears); rhinitis


Cough. Headache. Sore throat.


Dry skin. Redness. Pain.


Redness. Pain.

Eyes, skin, respiratory system

Methyl cyanoacrylate Use and Manufacturing

Methods of Manufacturing

The important step in most of the published syntheses is the classical Knoevenagel reaction using formaldehyde and a cyanoacetic ester. In this first step oligomeric cyanoacrylates, water, and other byproducts are formed. The reaction can be catalyzed by bases (e.g., amines), alkali metal tetraborates, metal carbonyls, or phase-transfer catalysts. The raw condensation product from the first reaction is depolymerized thermally (either continuously or discontinuously) and purified by distillation, chromatography on alumina or silica gel, crystallization in polyethylene columns, or treatment with zinc chloride. Alternatively, 2-cyanoacrylates can be manufactured by the ethoxycarbonylation of cyanoacetylene in the presence of nickel carbonyl. /2-Cyanoacrylates/|... /Alkyl 2-cyanoacrylates/ are prepared by pyrolyzing the poly(alkyl)-2-cyanoacrylates produced when formaldehyde is condensed with the corresponding alkyl cyanoacetates. /Cyanoacrylate adhesives/|Acrylate esters can be made by reacting a vinyl halide with carbon monoxide and an organic halide in the presence of a group VIII catalyst. Also developed is a process that yields acrylate esters after the generation of 2-halo-1-alkenes from hydrocarbon streams. Both processes were developed by Dow Chemical Co.

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2998]

To prevent premature polymerization, inhibitors are added. Supplied commercially as "Eastman 910." /Cyanoacrylate adhesives/|... Hydroquinone or monomethyl ether hydroquinone are added to acrylic monomers to stabilize them ... . /Acrylic ester monomers/

2-Propenoic acid, 2-cyano-, methyl ester: ACTIVE|Initially, cyanoacrylates were used /experimentally and clinically as a new tissue adhesive/ but these monomers have now fallen out of favor because of their toxic properties. The chief disadvantages ... are their irritant properties and their rapid degradation.|These adhesives have excellent polymerizing and bonding properties. /Cyanoacrylate adhesives/|... /2-cyanoacrylic acid/ methyl ester has been used satisfactorily for a special purpose in patients, applied to the skin of the eyelids & to the eye lashes to glue the lids temporarily closed, & in this application it has produced no ocular inflammation.

Method: OSHA 55; Procedure: high pressure liquid chromatography with ultraviolet detection; Analyte: methyl 2-cyanoacrylate; Matrix: air; Detection Limit: 10 ppb (0.05 mg/cu m).|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 liquid chromatography in order to obtain the partition coefficients of acrylates between 1-octanol and water (Log P). /ACRYLATES/

Fire Hazards -> Flammable - 2nd degree, Reactive - 1st degree

Computed Properties

Molecular Weight:111.10
XLogP3:0.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:111.032028402
Monoisotopic Mass:111.032028402
Topological Polar Surface Area:50.1
Heavy Atom Count:8
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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