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Home > Encyclopedia > Hexyl methacrylate

Hexyl methacrylate

Hexyl methacrylate structure

Hexyl methacrylate 

structure
  • CAS No:

    142-09-6

  • Formula:

    C10H18O2

  • Chemical Name:

    Hexyl methacrylate

  • Synonyms:

    2-Propenoic acid,2-methyl-,hexyl ester;Methacrylic acid,hexyl ester;Hexyl alcohol,methacrylate;Hexyl methacrylate;ENT 25419;Hexyl 2-methyl-2-propenoate;n-Hexyl methacrylate;SR 211;NSC 24169;2-Methyl-2-propenoic acid hexyl ester

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

PHYSICAL DESCRIPTION: Clear colorless liquid. (NTP, 1992)


N-hexyl methacrylate is a clear colorless liquid. (NTP, 1992)


N-hexyl methacrylate is a clear colorless liquid. (NTP, 1992)

Hexyl methacrylate Basic Attributes

170.25

170.25

1754703

205-521-9

538B2Q3HSV

24169

3082

DTXSID4025406

Liquid

2916140000

Characteristics

26.3

3.73 (est)

N-hexyl methacrylate is a clear colorless liquid. (NTP, 1992)

0.880 g/cm3 @ Temp: 25 °C

-59--55°C

162 °C

82°C

1.4310

In water, 39.97 mg/L at 25 deg C (est)

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. Storage temp below 30 deg C are recommended for the polyfunctional methacrylates.

2.29 mm Hg at 25 deg C (est)

5.9 (Air = 1)

Henry's Law constant = 5.97X10-4 atm-cu m/mole at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.55X10-11 cu cm/molec-sec at 25 °C (est)

This compound may be sensitive to heat, light, and air. May form peroxides. Slightly water soluble (NTP, 1992).

Acrylates and Acrylic Acids

Polymerizable

N-HEXYL METHACRYLATE may be sensitive to heat, light, and air. Combustible, polymerizes. (NTP, 1992)

Safety Information

III

3082

36/37/38-51/53-43

26-36-36/37-24/25

Xi

P280-P304 + P340 + P312-P305 + P351 + P338-P333 + P313-P337 + P313

H315-H317-H319-H335

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.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 250 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all 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 alcohol followed by washing with a strong soap and water solution. Do not 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)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Suitable protective clothing and self-contained respiratory protective apparatus should be available for use of those who may have to rescue persons overcome by fumes. /Acrylic acid and derivatives/

Combustible

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.

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 a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|... 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/

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

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Drug Information

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity.|Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme a derivative, which then enters the normal lipid metabolism. /Methacrylates/

ACUTE/CHRONIC HAZARDS: Toxic. (NTP, 1992)

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)

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Esters and related compounds/|/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 necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Provide a low-stimulus environment. 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 ... . Treat frostbite by rapid rewarming ... . /Esters and related compounds/|/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 ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

/OTHER TOXICITY INFORMATION/ Biologically, methacrylates resemble acrylates, except for lower reactivity and thus decreased toxicity. This is probably due to steric hindrance by its methyl group and in turn decreased rates of membrane transport and systemic translocation. /Methacrylic esters/

hexyl methacrylate

Hexyl methacrylate Use and Manufacturing

Methods of Manufacturing

The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/|Esterification or transesterification of n-hexyl alcohol with either methacrylic acid or methyl methacrylate

Uses

Monomer for plastics, molding powder, solvent coatings, adhesives, oil additives; emulsions for textile, leather and paper finishing.|Comonomer for acrylic resins.|Comonomer for polymers for deformation recording media.

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5404]

2-Propenoic acid, 2-methyl-, hexyl ester: ACTIVE|Alkyl mercury compounds have been used as seed disinfectants and for fungicides. They have also been used in organic synthesis. /Mercury alkyl compounds/|Methyl methacrylate, and in general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. Nonetheless, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/

THE METHOD IS BASED ON THE SEPARATION OF THE ESTERS FROM HEXYL ALCOHOL DURING ASPIRATION FROM THE AIR, AND THEIR SUBSEQUENT PHOTOMETRIC DETERMINATION BASED ON THEIR REACTION WITH NINHYDRIN IN A SULFURIC ACID MEDIUM. THE SENSITIVITY OF DETERMINATION IN THE STUDIED SOLN IS 5 UG, & THE ERROR IS 1.5-16.2% FOR HEXYLMETHACRYLATE.|Thin-layer chromatography, 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:170.25
XLogP3:4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:170.130679813
Monoisotopic Mass:170.130679813
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:150
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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