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Home > Encyclopedia > 1,4-Butanediol diglycidyl ether

1,4-Butanediol diglycidyl ether

1,4-Butanediol diglycidyl ether structure

1,4-Butanediol diglycidyl ether 

structure
  • CAS No:

    2425-79-8

  • Formula:

    C10H18O4

  • Chemical Name:

    1,4-Butanediol diglycidyl ether

  • Synonyms:

    Oxirane,2,2′-[1,4-butanediylbis(oxymethylene)]bis-;Butane,1,4-bis(2,3-epoxypropoxy)-;2,2′-[1,4-Butanediylbis(oxymethylene)]bis[oxirane];1,4-Butanediol diglycidyl ether;1,4-Bis(2,3-epoxypropoxy)butane;Tetramethylene glycol diglycidyl ether;1,4-Bis(glycidyloxy)butane;[Tetramethylenebis(oxymethylene)]dioxirane;1,4-Bis(2,3-epoxypropyloxy)butane;1,4-Diglycidyloxybutane;1,4-Butylene glycol diglycidyl ether;NSC 24834;BDDGE;1,4-Bis(oxiran-2-ylmethoxy)butane;Diluent 600;2-[4-(Oxiran-2-ylmethoxy)butoxymethyl]oxirane;BDDE;54350-59-3;162786-24-5

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Clear yellow liquid


1,4-butanediol diglycidyl ether is a clear pale yellow liquid. (NTP, 1992)|Liquid|COLOURLESS-TO-YELLOW LIQUID.


1,4-butanediol diglycidyl ether is a clear pale yellow liquid. (NTP, 1992)

1,4-Butanediol diglycidyl ether Basic Attributes

202.25

202.25

115238

219-371-7

E9MU425FIB

0110

24834

3334

DTXSID7024667

2910900090

Characteristics

43.5

-0.15

Clear yellow Liquid

1.1 g/cm3 @ Temp: 25 °C

155-160 °C

>230 °F

1.476

Solubility in water: miscible

-20°C

~10 mm Hg ( 20 °C)

Relative vapour density (air = 1): 7.0

Oral-rat LD50: 1134 mg/kg

Thermal decomposition emits toxic and spicy irritating smoke

Hygroscopic. Water soluble

Ethers

Polymerizable

1,4-BUTANEDIOL DIGLYCIDYL ETHER reacts with acids. (NTP, 1992)

Safety Information

NONH for all modes of transport

1

20/21-36/38-43-52/53-22

26-28-37/39-28B

EJ5100000

Xn

Treasury, low temperature, dry

Stable under normal temperatures and pressures.

P273-P280-P305 + P351 + P338

H302 + H312 + H332-H315-H317-H319-H412

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.

1-Chloro-2,3-epoxypropane, the mono- and di-2,3-epoxypropyl ethers of 1,4-butanediol, and 2,2-bis(4(2',3'-epoxypropoxy)phenyl)propane can, in the presence of catalytic quantities of halide ions, cause dehydrochlorination of trichloroethylene to dichloroacetylene, which causes minor explosions when the mixture is boiled under reflux. ... /Trichloroethylene; Epoxides/

Glycidyloxy compounds used in expoxy resin systems: A toxicology review.[Gardiner TH et al; Regul Toxicol Pharmacol 15 (2 Part 2): S1-S77 (1992)]|WHO; Chemical Safety Card: 1,4-Butanediol diglycidyl ether (1991)

This chemical is combustible. (NTP, 1992)|Combustible.

|Warning|H312: Harmful in contact with skin [Warning Acute toxicity, dermal]|P261, P264, P271, P272, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P333+P313, P337+P313, P362, P363, and P501|H302 (32.01%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 834 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, and P501|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use powder, alcohol-resistant foam, carbon dioxide.

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 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 and protect it from mineral acids. (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)

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.

Separated from strong oxidants, acids and bases. Cool. Keep in the dark. Ventilation along the floor.

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

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

Toxicity

moderately toxic

Drug Information

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes, nose mucous membranes and skin. ACUTE/CHRONIC HAZARDS: This compound is an irritant to the skin, eyes and nose. (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)


Fresh air, rest.


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


Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Three cases of occupational contact allergy due to an epoxy reactive diluent, 1,4-butanediol diglycidyl ether are reported. The patients were women employed in a brush factory. A two component epoxy glue was used to fix the bristles of certain brushes. Although the patients used a filling machine to fill metal parts of the brushes with the glue mixture, the glue constantly came in contact with the patients hands and arms. Airborne exposure was also possible as thousands of glued brushes were stored in the same work room. The first patient had been gluing for 6 mo, the second patient for 6 wk, and the third for 3 wk. None had dermatitis on the face. They used disposable polyvinyl chloride gloves during filling. The second worker worked for 4 wk without gloves. The first and third workers used barrier creams rather than gloves once the dermatitis started because the employer believed the gloves had caused the problem. The glue contained a bisphenol A type epoxy resin, the reactive diluent 1,4-butanediol diglycidyl ether and inert fillers. In all cases, patch tests to the /diluent/ showed positive reactions. Permeation tests showed that /the diluent/ penetrated disposable polyvinyl chloride and rubber gloves less than 30 min, yielding an allergic patch test reaction. ...

1,4-bis(2,3-epoxypropoxy)butane

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

Cough. Sore throat.


Redness. Pain.


Redness. Pain.

1,4-Butanediol diglycidyl ether Use and Manufacturing

Methods of Manufacturing

REACTION OF 1,4-BUTANEDIOL WITH EPICHLOROHYDRIN IN THE PRESENCE OF A LEWIS ACID CATALYST FOLLOWED BY DEHYDROHALOGENATION WITH SODIUM HYDROXIDE

Uses


Adhesives and sealant chemicals


Adhesives and sealants

Production

1,000,000 - 10,000,000 lb|(1977) AT LEAST 4.54X10+7 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Adhesive manufacturing|Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Computed Properties

Molecular Weight:202.25
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:202.12050905
Monoisotopic Mass:202.12050905
Topological Polar Surface Area:43.5
Heavy Atom Count:14
Complexity:144
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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