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Resorcinol diglycidyl ether

Resorcinol diglycidyl ether structure

Resorcinol diglycidyl ether 

structure
  • CAS No:

    101-90-6

  • Formula:

    C12H14O4

  • Chemical Name:

    Resorcinol diglycidyl ether

  • Synonyms:

    Oxirane,2,2′-[1,3-phenylenebis(oxymethylene)]bis-;Benzene,m-bis(2,3-epoxypropoxy)-;2,2′-[1,3-Phenylenebis(oxymethylene)]bis[oxirane];m-Bis(2,3-epoxypropoxy)benzene;Resorcinol diglycidyl ether;Diglycidyl resorcinol ether;Resorcinol glycidyl ether;Resorcinol bis(2,3-epoxypropyl) ether;1,3-Bis(2,3-epoxypropoxy)benzene;m-Bis(glycidyloxy)benzene;NSC 76621;1,3-Diglycidyloxybenzene;1,3-Dihydroxybenzene diglycidyl ether;2-[3-(Oxiran-2-ylmethoxy)phenoxymethyl]oxirane;2-[[3-(Oxiran-2-ylmethoxy)phenoxy]methyl]oxirane;KMC 694;168331-52-0;2056031-50-4

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

YELLOW PASTE OR LIQUID WITH CHARACTERISTIC ODOUR.


Diglycidyl resorcinol ether appears as clear yellow or straw-yellow viscous liquid. Boiling point 172°C; density 1.21 g / cm3. Possible carcinogen.|Liquid|YELLOW PASTE OR LIQUID WITH CHARACTERISTIC ODOUR.


Diglycidyl resorcinol ether appears as clear yellow or straw-yellow viscous liquid. Boiling point 172°C; density 1.21 g / cm3. Possible carcinogen.|Diglycidyl resorcinol ether is an aromatic ether.|Diglycidyl Resorcinol Ether is a combustible, yellowish liquid with a slight phenolic odor. Diglycidyl resorcinol ether is used as a liquid spray epoxy resin and in the production of other epoxy resins. Exposure to this substance irritates the eyes, skin and respiratory tract and adversely affects the immune system, central nervous system, liver and gastrointestinal tract. This substance is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. (NCI05)

Resorcinol diglycidyl ether Basic Attributes

222.237

222.24

202-987-5

FXN2Y6QZ2W

0193

76621

2811

DTXSID2020470

C44376

STRAW-YELLOW LIQUID

2910900090

Characteristics

43.52000

1.15

Diglycidyl resorcinol ether appears as clear yellow or straw-yellow viscous liquid. Boiling point 172°C; density 1.21 g / cm3. Possible carcinogen.

1.21 g/cm3 @ Temp: 25 °C

32-33 °C

172 °C @ Press: 0.8 Torr

156.6±26.4 °C

1.557

Miscible with most org resins

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should b

VAPOR PRESSURE LOW

Relative vapour density (air = 1): 7.7

SLIGHT PHENOLIC ODOR

Insoluble in water.

Ethers

DIGLYCIDYL RESORCINOL ETHER is an alkylating agent. Reacts with compounds having a labile hydrogen (NTP, 1992).

Safety Information

II

6.1

2811

2

R21/22;R36/38;R40;R43;R52/53;R68

S23-S36/37-S61

VH1050000

Xn:Harmful;

Separated from strong oxidants, strong bases, strong acids and amines. Cool. Keep in the dark.

Stable. Combustible. Incompatible with strong oxidizing agents.

P273-P280-P305 + P351 + P338

H302 + H312-H315-H317-H319-H341-H351-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.|Incineration: It should be atomized into an incinerator and combustion may be improved by mixing with a more flammable solvent (acetone or benzene).|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for DIGLYCIDYL RESORCINOL ETHER (7 total), please visit the HSDB record page.

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Diglycidyl Resorcinol Ether (101-90-6) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s072disl.pdf]|DHHS/NTP; Toxicology & Carcinogenesis Studies of Diglycidyl Resorcinol Ether (Technical Grade) in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 257 (1986) NIH Publication No. 87-2513

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

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P405, and P501|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P405, and P501|Aggregated GHS information provided by 440 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P271, P272, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501

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

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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, FIRST REMOVE ALL SOURCES OF IGNITION. Then, 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 60-70% ethanol followed by washing with a 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 under ambient conditions. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek protective clothing is not worn during the handling of this chemical, wear disposable Tyvek sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for DIGLYCIDYL RESORCINOL ETHER (10 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

MODERATELY TO HIGHLY IRRITATING ON SKIN CONTACT.|Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/|... Instances of eye irritation in workers have been noticed. /Diglycidyl resorcinol/

Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from strong oxidants, strong bases, strong acids and amines. Cool. Keep in the dark.

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

Repeated or prolonged contact may cause skin sensitization. This substance is possibly carcinogenic to humans.

NO open flames.

See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE. AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

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

Toxicity

LD50 Rat oral 2.57 g/kg|LD50 Mouse intragastric 0.98 g/kg|LD50 Rabbit intragastric 1.24 g/kg|LD50 Rat ip 0.178 g/kg|For more Non-Human Toxicity Values (Complete) data for DIGLYCIDYL RESORCINOL ETHER (7 total), please visit the HSDB record page.

Toxicology and carcinogenesis studies of technical grade diglycidyl resorcinol ether (81 % pure) were conducted by admin the chemical in corn oil by gavage to groups of 50 male and 50 female F344/N rats at doses of 25 or 50 mg/kg and to groups of 50 male and female B6C3F1 mice at doses of 50 or 100 mg/kg. A supplemental study of similar design in male and female rats (0 or 12 mg/kg) was started approximately 12 months later because of high mortality in the 50 mg/kg dose groups. Doses were administered five times per week for 103 weeks. Groups of 50 rats and 50 mice of each sex received corn oil by gavage on the same dosing schedule and served as vehicle controls. ... Under the conditions of these 2-year gavage studies, technical grade diglycidyl resorcinol ether caused hyperkeratosis and hyperplasia of the forestomach in rats and mice. DGRE was carcinogenic for male and female F344/N rats and for male and female B6C3Fl mice, causing both benign and malignant neoplasms of the forestomach. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice; Positive; Female Mice: Positive.

Drug Information

SYMPTOMS: Symptoms of exposure to this compound include respiratory tract irritation, severe skin and eye irritation and skin sensitization. On skin contact it can cause severe burns. ACUTE/CHRONIC HAZARDS: This compound is a severe irritant of the skin and eyes. It causes skin burns on contact. When heated to decomposition it emits acrid smoke and irritating fumes. (NTP, 1992)|Carcinogens

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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. Transport the victim IMMEDIATELY to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


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

/SRP:/ 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/|/SRP:/ 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/

DIGLYCIDYL RESORCINOL ETHER PRODUCES SEVERE BURNS ON CONTACT WITH SKIN, & SKIN SENSITIZATION HAS OCCURRED IN LIMITED NUMBER OF CASES.|QUESTIONABLE DECREASE IN WHITE COUNT & SUGGESTION OF APPEARANCE OF ATYPICAL MONOCYTIC CELLS IN PERIPHERAL BLOOD.|... SLIGHTLY TOXIC BY INGESTION. MODERATELY TO HIGHLY IRRITATING ON SKIN CONTACT MODERATE RADIOMIMETIC ACTIVITY.|Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/

1,3-bis(2,3-epoxypropoxy)benzene

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

Cough. Sore throat.


MAY BE ABSORBED! Redness. Pain.


Redness. Pain.

Resorcinol diglycidyl ether Use and Manufacturing

Methods of Manufacturing

REACTION OF EXCESS OF EPICHLOROHYDRIN WITH RESORCINOL IN ALKALINE SOLN.

Uses

Adhesives and sealant chemicals


Adhesives and sealants

Production

(1977) NOT PRODUCED COMMERCIALLY IN USA|(1979) NOT PRODUCED COMMERCIALLY IN USA

All other chemical product and preparation manufacturing|Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.|CURED RESINS MADE FROM IT HAVE BEEN REPORTED TO HAVE CHARACTERISTICS WHICH MAKE THEM USEFUL FOR ELECTRICAL, CASTING, TOOLING, ADHESIVE & LAMINATING APPLICATIONS & AS COATING FOR METAL & CERTAIN PAVEMENTS TO INCR TENSILE STRENGTH.

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:222.24
XLogP3:1.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:222.08920892
Monoisotopic Mass:222.08920892
Topological Polar Surface Area:43.5
Heavy Atom Count:16
Complexity:211
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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