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Home > Encyclopedia > 1,6-Hexanediol diacrylate

1,6-Hexanediol diacrylate

1,6-Hexanediol diacrylate structure

1,6-Hexanediol diacrylate 

structure
  • CAS No:

    13048-33-4

  • Formula:

    C12H18O4

  • Chemical Name:

    1,6-Hexanediol diacrylate

  • Synonyms:

    2-Propenoic acid,1,1′-(1,6-hexanediyl) ester;Acrylic acid,hexamethylene ester;2-Propenoic acid,1,6-hexanediyl ester;1,6-Hexanediol diacrylate;Hexamethylene diacrylate;Hexamethylene acrylate;Hexamethyleneglycol diacrylate;1,6-Hexanediyl diacrylate;SR 238;1,6-Hexamethylene diacrylate;Sartomer SR 238;Setalux UV 2243;Hexaneglycol diacrylate;HDDA;Kayarad HDDA;Light Acrylate 1,6HX-A;1,6-HDDA;1,6-Hexenediol diacrylate;NK Ester A-HD;C 716;Viscoat 230;Photomer 4017;1,6HX-A;AHD;Sartomer 238;1,6-Hexamethylenediol diacrylate;Kayarad KS-HDDA;Actilane 425;Light Ester 1.6HX-A;Laromer HDDA;HDODA;Hexamethylenediol diacrylate;Genomer 1223;NK Ester A-HD-N;KS-HDDA;SR 238F;AgiSyn 2816;A-HD-N;1.6HX;EM 221;C 6DA;V 230;M 200;SM 626;M 200 (acrylate);Photomer 4017F;SR 2389;EM 221TF;SR 238NS;Light Acrylate SR 238F;SR 238B;FA 126AS;1,2-Bisacryloyloxyhexane;Miramer M 200;1,6-Hexandiol diacrylate;Newfrontier HDDA;LM 254;Hexylene-1,6-diacrylate;Doublemer HDDA;Cognis 4017;Fancryl FA 126AS;1,6-Hexyleneglycol diacrylate;SR 238TFN;EM 2021;74872-03-0;88250-32-2;106717-06-0;126038-89-9;174845-65-9;181826-08-4;198694-76-7;671774-75-7;1220287-86-4;1934258-74-8

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Colorless transparent liquidHexamethylene diacrylate (also known as hexanediol diacrylate) is a di-functional acrylic monomer that can be polymerized by free radicals. It is used in ultra violet (UV) and electron beam (EB) applications as a reactive component in formulating coatings and inks, furniture and floor coatings, coatings on plastic substrates, varnishes for packing items and more.


1,6-hexanediol diacrylate is a clear yellow liquid. (NTP, 1992)|Liquid|Clear yellow liquid with a mild ester-like odor.


1,6-hexanediol diacrylate is a clear yellow liquid. (NTP, 1992)

1,6-Hexanediol diacrylate Basic Attributes

226.27

226.27

235-921-9

FY751V5MMY

3082

DTXSID9025401

29161290

Characteristics

52.6

2.6

1,6-hexanediol diacrylate is a clear yellow liquid. (NTP, 1992)

1.01 g/cm3

<25 °C

158-165 °C @ Press: 5 Torr

>230 °F

n 20/D 1.456(lit.)

Slightly miscible with water.Insoluble 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. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/

<0.01 mm Hg ( 20 °C)

>1 (vs air)

Henry's Law constant = 3.7X10-8 atm cu m/mol @ 25 °C /Estimated/

Reacts readily with electrophilic, free-radical, and nucleophilic agents /Acrylic acids and esters/|Hydroxyl radical reaction rate constant = 2.7X10-11 cu cm/molecule-sec @ 25 °C /Estimated/

Insoluble in water.

Acrylates and Acrylic Acids

Polymerizable

1,6-HEXANEDIOL DIACRYLATE is temperature sensitive (NTP, 1992). May react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release gaseous hydrogen. Can undergo very exothermic addition polymerization reactions. May undergo autoxidation upon exposure to the air to form explosive peroxides.

Safety Information

III

9

UN 3082 9/PG 3

2

R36/38;R43

39

AT1430000

Xi

P280-P305 + P351 + P338

H315-H317-H319

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

This chemical is probably combustible. (NTP, 1992)

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 3296 companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide 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: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (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/|... Gloves and protective clothing and shoes or boots should be used in addition to eye (or full face) protective equipment. /Acrylic acid & derivatives/

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 molecular weight esters of acrylic acids are irritants to skin, eyes and mucous membranes. /Acrylic acid esters/

Toxicity

LD50 Rabbit dermal 3600 mg/kg|LD50 Rat oral 5 g/kg

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. /Acrylates/

...Dimethacrylates proved to be moderate to strong sensitizers in the guinea pig.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 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)

Basic treatment: Establish a patent airway. 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 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|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. 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 /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. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/HUMAN EXPOSURE STUDIES/ /Brief/ topical contact with 1,6-hexanediol diacrylate may cause delayed irritant dermatitis. During a 4 yr observation of 20 workers, contact sensitization did not occur.|/SIGNS AND SYMPTOMS/ Human signs and symptoms following ingestion of acrylic monomers include collapse, severe respiratory difficulties, and CNS stimulation. /Acrylates/|/SIGNS AND SYMPTOMS/ Allergic reactions have been reported for some acrylates. /Acrylates/|/CASE REPORTS/ ... We report two cases of workers in the printing industry who developed allergic contact dermatitis to 1,6-hexanediol diacrylate (HDDA) within a short period of exposure. The first developed within weeks of exposure to a plastic sheet primed with HDDA. The second developed after a single accidental exposure.|/CASE REPORTS/ A case of sensitization after a single occupational exposure to 1,6-hexanediol-diacrylate (HDDA) was reported in an employee in a plastic paint factory.

1,6-hexanediol diacrylate

1,6-Hexanediol diacrylate Use and Manufacturing

Methods of Manufacturing

ESTERIFICATION OF 1,6-HEXANEDIOL WITH ACRYLIC ACID|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/|The acrylates can be manufactured by a number of procedures. These include dehydration of the corresponding hydroxyalkanoic acid, saponification of the alkaline nitrile, catalytic hydration of acetylene and carbon monoxide, or the reaction of acetone with hydrocyanic acid. /Acrylates/

Uses

Adhesives and sealant chemicals


Adhesives and sealants

Production

10,000,000 - 50,000,000 lb|(1979) PROBABLY GREATER THAN 4.54X10+6 G|(1981) PROBABLY GREATER THAN 4.54X10+6 G

Adhesive manufacturing|2-Propenoic acid, 1,1'-(1,6-hexanediyl) 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, 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:226.27
XLogP3:2.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:11
Exact Mass:226.12050905
Monoisotopic Mass:226.12050905
Topological Polar Surface Area:52.6
Heavy Atom Count:16
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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