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Home > Encyclopedia > Neopentyl glycol diacrylate

Neopentyl glycol diacrylate

Neopentyl glycol diacrylate structure

Neopentyl glycol diacrylate 

structure
  • CAS No:

    2223-82-7

  • Formula:

    C11H16O4

  • Chemical Name:

    Neopentyl glycol diacrylate

  • Synonyms:

    2-Propenoic acid,1,1′-(2,2-dimethyl-1,3-propanediyl) ester;Acrylic acid,2,2-dimethyltrimethylene ester;2-Propenoic acid,2,2-dimethyl-1,3-propanediyl ester;1,3-Propanediol,2,2-dimethyl-,diacrylate;2,2-Dimethyltrimethylene acrylate;Sartomer SR 247;Dimethylolpropane diacrylate;2,2-Dimethylpropane-1,3-diol diacrylate;Neopentyl glycol diacrylate;Neopentanediol diacrylate;NK Ester A-NPG;Kayarad NPGDA;Viscoat 247;NPGDA;Viscoat 215;2,2-Dimethylpropanediol diacrylate;Light Acrylate ND-A;Light Acrylate NP-A;Sartomer 247;NSC 97407;A-NPG;NP-A;Etermer EM 225;EM 225;SR 247;(2,2-Dimethyl-3-prop-2-enoyloxypropyl) prop-2-enoate;2,2-Dimethylpropane-1,3-diyl diacrylate;95576-40-2;127194-97-2

  • Categories:

    Specialty Chemicals

Description

LIQUID.


Liquid|LIQUID.

Neopentyl glycol diacrylate Basic Attributes

212.242

212.24

218-741-5

0OHU17DNNU

1286

97407

DTXSID0051869

Colorless liquid

2916190090

Characteristics

52.60000

1.86

Liquid

1.0 g/cm3

6 °C

96 °C @ Press: 0.98 Torr

123.6±18.2 °C

1.452

Solubility in water: poor

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/

0.03 mm Hg at 20 deg C

Relative vapour density (air = 1): 7.3

Henry's Law constant = 3.6X10-7 atm-cu m/mol at 25 °C (est)

BP at 0.13 kPa: 96 °C|React readily with electrophilic, free-radical, and nucleophilic agent /Acrylic acid & esters/|Vapors are uninhibited and may polymerize; the liquid substance may polymerize|Hydroxyl radical reaction rate constant = 2.24X10-11 cu cm/molecule-sec at 25 °C (est)

Vapours are uninhibited and may polymerize in vents or flame arresters, causing blockage.

Safety Information

III

6.1(b)

UN 2810 6.1/PG 2

1

R24;R36/38;R43

S28-S39-S45

AS8925000

T:Toxic;

Cool. Store only if stabilized.

P280-P305 + P351 + P338-P312

H311-H315-H317-H319

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.

Combustible.

|Danger|H311: Toxic in contact with skin [Danger Acute toxicity, dermal]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P312, P321, P322, P332+P313, P333+P313, P337+P313, P361, P362, P363, P405, and P501|H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]|Aggregated GHS information provided by 280 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

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/|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/

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 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.|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 lower-molecular-wt esters of acrylic acids are irritants to skin, eyes and mucous membranes. /Acrylic acid esters/

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit.

Cool. Store only if stabilized.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles, face shield or eye protection in combination with breathing protection.

Toxicity

LD50 Rabbit skin 283 uL/kg|LD50 Rat oral 5190 uL/kg

2,2-Dimethyltrimethylene acrylate's production and use as a monomer in the production of UV-curable polymers, resins, coatings and inks(1) 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 40(SRC), determined from a structure estimation method(2), indicates that 2,2-dimethyltrimethylene acrylate is expected to have very high mobility in soil(SRC). Volatilization of 2,2-dimethyltrimethylene acrylate from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 3.6X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Although 2,2-dimethyltrimethylene acrylate has a vapor pressure of 0.03 mm Hg at 20 °C(3), the compound is a liquid at room temperatures and presents a vapor and inhalation exposure in spill or occupational handling scenarios(3). By analogy to other acrylates (ethyl acrylate, butyl acrylate and hydroxypropyl acrylate) that have been shown to biodegrade readily via the Japanese MITI test (52-61% theoretical BOD in 2 weeks or 83% in 4 weeks)(4), 2,2-dimethyltrimethylene acrylate may also biodegrade readily(SRC). [|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that 2,2-dimethyltrimethylene acrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected to be slow(3) based upon an estimated Henry's Law constant of 3.6X10-7 atm-cu m/mole at 25 °C(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 148 days and 1080 days, respectively(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.016 L/mole-sec(SRC) can be estimated using a structure estimation method(4) which corresponds to half-lives of 13.6 and 1.36 years at pH values of 7 and 8, respectively(SRC). According to a classification scheme(5), an estimated BCF of 20(SRC), from an estimated log Kow of 2,48(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). By analogy to other acrylates (ethyl acrylate, butyl acrylate and hydroxypropyl acrylate) that have been shown to biodegrade readily via the Japanese MITI test (52-61% theoretical BOD in 2 weeks or 83% in 4 weeks)(6), 2,2-dimethyltrimethylene acrylate may also biodegrade readily(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2-dimethyltrimethylene acrylate, which has a vapor pressure of 0.03 mm Hg at 20 °C(2)), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,2-dimethyltrimethylene acrylate 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 17 hours(SRC), calculated from its rate constant of 2.24X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase 2,2-dimethyltrimethylene acrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 3.3 days(SRC), calculated from its rate constant of 3.5X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2,2-dimethyltrimethylene acrylate with photochemically-produced hydroxyl radicals has been estimated as 2.24X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2,2-dimethyltrimethylene acrylate with ozone has been estimated as 3.5X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.3 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.016 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 13.6 and 1.36 years at pH values of 7 and 8, respectively(2).

An estimated BCF of 20 was calculated in fish for 2,2-dimethyltrimethylene acrylate(SRC), using an estimated log Kow of 2.48(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,2-dimethyltrimethylene acrylate can be estimated to be 40(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2-dimethyltrimethylene acrylate is expected to have very high mobility in soil.

The Henry's Law constant for 2,2-dimethyltrimethylene acrylate is estimated as 3.6X10-7 atm-cu m/mole at 25 °C(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2-dimethyltrimethylene acrylate is expected to volatilize slowly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 148 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 1080 days(SRC). 2,2-Dimethyltrimethylene acrylate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur slowly(SRC). Although 2,2-dimethyltrimethylene acrylate has a vapor pressure of 0.03 mm Hg at 20 °C(3), the compound is a liquid at room temperatures and presents a vapor and inhalation exposure in spill or occupational handling scenarios(3).

Occupational exposure to 2,2-dimethyltrimethylene acrylate may occur through inhalation of vapor and dermal contact(1) with this compound at workplaces where 2,2-dimethyltrimethylene acrylate is produced or used(SRC).

Drug Information

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/

/SIGNS AND SYMPTOMS/ The toxicity of the acrylates decreases with increasing molecular weight. ... Human signs & symptoms following ingestion of acrylic monomers include collapse, severe respiration difficulties, and CNS stimulation. Inhalation of higher concentrations may cause marked irritation, salivation, conjunctival irritation, and 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 include pulmonary congestion or hemorrhage and cloudy swelling of liver and kidney. /Acrylates/

neopentylglycol diacrylate

The substance can be absorbed into the body by inhalation and through the skin.

Cough. Sore throat.


MAY BE ABSORBED! Redness.


Redness. Pain.

Neopentyl glycol diacrylate Use and Manufacturing

Methods of Manufacturing

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/|Acrylates can be prepared by ... dehydration of the corresponding hydroxyalkanoic acid, saponification of the alkene nitrile, catalytic hydration of acetylene and carbon monoxide, or the reaction of acetone with hydrocyanic acid. /Acrylates/|ESTERIFICATION OF NEOPENTYL GLYCOL WITH ACRYLIC ACID

Uses

Adhesives and sealant chemicals


Adhesives and sealants

Production

(1977) AT LEAST 4.54X10+5 G|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5409]

Adhesive manufacturing|2-Propenoic acid, 1,1'-(2,2-dimethyl-1,3-propanediyl) ester: ACTIVE|... Hydroquinone or monomethyl ether hydroquinone are added to acrylic monomers to stabilize them ... . /Acrylic ester monomers/

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 and 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/

Computed Properties

Molecular Weight:212.24
XLogP3:2.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:212.10485899
Monoisotopic Mass:212.10485899
Topological Polar Surface Area:52.6
Heavy Atom Count:15
Complexity:240
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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