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1,4-Butanediol diglycidyl ether

HCID 17046
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
2425-79-8
Standard SMILES
C(CCOCC1CO1)COCC1CO1
InChIKey
SHKUUQIDMUMQQK-UHFFFAOYSA-N
Molecular formula
C10H18O4
Average molar mass
202.25 g/mol
Monoisotopic mass
202.12050906

Overview

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

Names & identifiers

Preferred name
1,4-Butanediol diglycidyl ether
IUPAC
2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane
English name
1,4-Butanediol diglycidyl ether
Molecular formula
C10H18O4
Molecular weight
202.25

Names & synonyms

1,4-Butanediol diglycidyl ether2425-79-81,4-Butane diglycidyl ether1,4-DiglycidyloxybutaneAraldit DY 026Butanediol diglycidyl ether1,4-Bis(glycidyloxy)butane1,4-BIS(2,3-EPOXYPROPOXY)BUTANETetramethylene glycol diglycidyl etherGrilonit RV 18061,4-Bis(2,3-epoxypropyloxy)butaneDTXSID7024667
Show more names
BDDE1,4-bis(oxiran-2-ylMethoxy)butane1,4-Diglycidloxybutane1,4-Butanediol diglycidyl ether >=95%BUDGE1,4-Butanediyl diglycidyl ethertk10352
Butane, 1,4-bis(2,3-epoxypropoxy)-Butane-1:4-diol diglycidyl etherTK 10352CD 15006 AE9MU425FIBOxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-NSC-24834(Tetramethylenebis(oxymethylene))dioxirane

Database identifiers

CAS
2425-79-8、26951-52-0
PubChem CID
17046

Properties

Computed structural properties

XLogP
0
Topological polar surface area
43.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
9
Heavy atoms
14
Formal charge
0
Complexity
144

Experimental & physicochemical properties

Chemical ClassesIndustrial compound
PolymersPlastics & Rubber -> Glycidyl Ethers
LogP-0.15
Density · 5 items

1.09 to 1.10 at 77 °F (NTP, 1992)

1.1 g/cu cm @ 25 °C

1.1 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.08

1.049 @25 °C

Solubility · 2 items

10 to 50 mg/mL at 70 °F (NTP, 1992)

Solubility in water: miscible

Flash Point · 3 items

greater than 200 °F (NTP, 1992)

129 °C

129 °C

Boiling Point · 4 items

311 to 320 °F at 11 mmHg (NTP, 1992)

155-160 @ 11 mm Hg

266 °C

266 °C @760 [mm Hg]

Vapor DensityRelative vapor density (air = 1): 7.0
Vapor Pressure · 2 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H312: Harmful in contact with skin [Warning Acute toxicity, dermal]

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P317, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Danger

H302+H312+H332 (10%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Chemical: Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-

Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 14-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/16131

Butanediol diglycidyl ether: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelClass 9
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes, nose mucous membranes and skin.

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used as reactive diluent for epoxy resins (reduces viscosity) and as a flexibilizer for aromatic resins; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

REACTIVE DILUENT FOR EPOXY RESINS (REDUCES VISCOSITY)

FLEXIBILIZER FOR AROMATIC RESINS

U.S. Production · 3 items

2023: 700,000 - <850,000 lb

(1977) AT LEAST 4.54X10+7 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Consumer UsesViscosity modifiers
Industry UsesIntermediate
Methods of ManufacturingREACTION OF 1,4-BUTANEDIOL WITH EPICHLOROHYDRIN IN THE PRESENCE OF A LEWIS ACID CATALYST FOLLOWED BY DEHYDROHALOGENATION WITH SODIUM HYDROXIDE
General Manufacturing Information · 2 items

Construction

Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-: ACTIVE

Applications · 3 items

Description1,4-Butanediol diglycidyl ether is a reactive diluent in epoxy resins.

Uses1,4-Butanediol diglycidyl ether is used for preparing amylose, xylan and hydroxyethyl-cellulose, to cross link polyethylenimine which also serves as a hole-blocking layer in organic solar cells, to cross link hyaluronic acid into hydrogels and for the activation of soluble dextran polymers. It is the most commonly used homobifunctional epoxide compound

General DescriptionClear pale yellow liquid.

Upstream & downstream products

Upstream raw materials

Related reactions

2 records
New reaction record
HRID 5034 reaction equation
HRID 5034As reactantuspto-grants-1993_09
HRID 373331 reaction equation
HRID 373331As productuspto-grants-1992_11

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
DTXSID
DTXSID7024667
ChEMBL
CHEMBL1450123
UNII
E9MU425FIB
EC Number
219-371-7、608-023-3
Nikkaji
J42.721G

9.8 [mmHg]

Vapor pressure, kPa at 20 °C: 1.3

Physical Description · 4 items

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

Liquid

Colorless to yellow liquid; [ICSC] Light yellow viscous liquid; [MSDSonline]

COLOURLESS-TO-YELLOW LIQUID.

Relative Evaporation Rate0.012-0.018 Pa.s @ 25 °C

Physicochemical properties

Melting point
-21 °C · -21 °C
Boiling point
266 °C · 266 °C (lit.)
Density
1.1 g/mL · 1.1 g/mL at 25 °C (lit.)
vapor pressure
10 mm · ~10 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.453
Flash point
230 °F · >230 °F
storage temp.
2 · Inert atmosphere,2-8°C
solubility
Chloroform (Soluble), Methanol (Slightly)
form
Liquid
Specific Gravity
1.07 · 1.07
color
Clear yellow
Water Solubility
SOLUBLE
Sensitive
Hygroscopic
BRN
115238 · 115238
Stability
Hygroscopic
InChI
1S/C10H18O4/c1(3-11-5-9-7-13-9)2-4-12-6-10-8-14-10/h9-10H,1-8H2
InChIKey
SHKUUQIDMUMQQK-UHFFFAOYSA-N
SMILES
C(CCOCC1CO1)COCC2CO2
LogP
-0.27 at · -0.27 at 25℃
CAS DataBase Reference
2425 · 2425-79-8(CAS DataBase Reference)
FDA UNII
9 MU425FIB · E9MU425FIB
NIST Chemistry Reference
2 · Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-(2425-79-8)
EPA Substance Registry System
1 · 1,4-Butanediol diglycidyl ether (2425-79-8)
UNSPSC Code
41116107 · 41116107
NACRES
23 · NA.23
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302+H312+H332-H315-H317-H318-H412
Precautionary statements
273 · P273-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xn
Risk Statements
20 · 20/21-36/38-43-52/53-22
Safety Statements
26 · 26-28-37/39-28B
WGK Germany
1 · 1
RTECS
5100000 · EJ5100000
F
3 · 3-10
TSCA
TSCA listed
HS Code
29109000 · 29109000
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Irrit. 2Skin Sens. 1
Hazardous Substances Data
2425 · 2425-79-8(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 1134mg/kg
REACH Registrations
Active
Hazards SummaryA respiratory tract irritant; A severe skin and eye irritant; May cause skin sensitization; [ICSC] An irritant; May cause skin sensitization; Can be absorbed through skin; [MSDSonline] Danger of skin sensitization; [MAK] See GLYCDYL ETHERS.
Reactive GroupEthers
EC ClassificationSymbol: Xn; R: 20/21-36/38-43; S: (2)-26-28-37/39
Special Reports · 2 items

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)

TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, 2,2'-(1,4-butanediylbis(oxymethylene))bis- is included on this list.

Reactivity AlertsPolymerizable
Reactivity Profile1,4-BUTANEDIOL DIGLYCIDYL ETHER reacts with acids. (NTP, 1992)
Chemical DangersThe substance can presumably form explosive peroxides. Reacts with strong oxidants, acids and bases.

Safety & protection

Fire Fighting · 2 items

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.

First Aid Measures · 4 items

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.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

First Aid · 1 item

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.

Safe StorageSeparated from strong oxidants, acids and bases. Cool. Keep in the dark. Ventilation along the floor.
Nonfire Spill Response · 1 item

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.

Disposal Methods · 1 item

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.

Spillage Disposal · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskNo 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.
Skin PreventionProtective gloves. Protective clothing.

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesThe substance can be absorbed into the body through the skin and by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

Burning sensation. Sore throat.

TSCA Test Submissions · 3 items

1,4-Butanediol-diglycidyl ether was evaluated for the ability to increase the incidence of nuclear anomalies in bone marrow cells of male and female hamsters treated by oral gavage. In one trial, groups of 12 animals ( 6 male, 6 female ) received 600, 1200 or 2400 mg/kg of test article 1x daily for 2 days. In a second trial, groups of 16 animals ( 8 male, 8 female ) received 1000, 1500, 2000, 2500 or 3000 mg/kg of test article 1x daily for 2 days. In both trials, hamsters were sacrificed 24 hours following the second dose. A statistically significant ( Chi-square test, p < 0.05 ) increase in the percentage of cells with nuclear anomalies (including single Jolly bodies, fragments of nuclei in erythrocytes, micronuclei in erythroblasts and leucopoietic cells, and polyploid cells) was observed at 2400 mg/kg in the first test, and at 1500, 2500 and 3000 mg/kg in the second test. The toxicity of 1,4-butandiol-diglycidyl ether to hamsters at the doses administered was not reported.

The mutagenicity of 1,4-butanediol diglycidyl ether (BDE) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, BDE, diluted with DMSO, was tested for mutagenicity at concentrations up to 10,000 ug/plate using the plate incorporation method. BDE caused a reproducible positive response without activation in tester strains TA1538, TA98 and TA100 and with activation in testers strains TA98 and TA100. Positive responses were observed at dose levels as low as 500 ug/plate, both with and without activation.

The ability of 1,4-butanediol-diglycidyl ether (BDGE) to induce Sister Chromatid Exchange (SCE) in bone marrow cells of male and female Chinese hamsters (4/sex/group) orally exposed by gavage to single doses of 0, 600, 1200 or 2400 mg/kg was evaluated. Animals were sacrificed 24 hrs after treatment. Slides of 2 female and 2 male animals from each group were examined and 25 metaphases of the second cell cycle were analyzed per animal. None of the tested concentrations induced a statistically significant increase in the frequency of SCE relative to the solvent controls (0.5% sodium carboxymethylcellulose plus 0.1% Tween 80).

Human Toxicity Excerpts · 1 item

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. ...

Non-Human Toxicity Excerpts · 1 item

SENSITIZATION CAPACITY OF 6 EPOXY REACTIVE DILUENTS (INCL 1,4-BIS(2,3-EPOXYPROPOXY)BUTANE) WAS INVESTIGATED WITH GUINEA PIG MAXIMIZATION TEST. ALL LOW MOL WT REACTIVE DILUENTS (MOL WT 175 TO 360) PROVED TO BE SENSITIZERS. ONE DILUENT OF MOL WT 1700 PRODUCED NO REACTION.

Toxicity DataLC (rat) > 250 ppm/6h

Regulatory information

TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, 2,2'-(1,4-butanediylbis(oxymethylene))bis- is included on this list.

Safety data

F
3-10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
EJ5100000
hs_code
29109000
Toxicity
LD50 oral in rat: 1134mg/kg
risk_code
20/21-36/38-43-52/53-22
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
Xn
safety_code
26-28-37/39-28B
Storage Class
10 - Combustible liquids
Hazard statements
H302+H312+H332-H315-H317-H318-H412
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Irrit. 2Skin Sens. 1
Precautionary statements
P273-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
Hazardous Substances Data
2425-79-8(Hazardous Substances Data)
Epichlorohydrin
1,4-Butanediol

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