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1,4-ブタンジオールジグリシジルエーテル

1,4-Butanediol diglycidyl ether

HCID 17046
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印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
2425-79-8
標準SMILES
C(CCOCC1CO1)COCC1CO1
InChIKey
SHKUUQIDMUMQQK-UHFFFAOYSA-N
分子式
C10H18O4
平均分子量
202.25 g/mol
単同位体質量
202.12050905

概要

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

名称と識別子

優先名称
1,4-Butanediol diglycidyl ether
IUPAC
2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane
現地名
1,4-ブタンジオールジグリシジルエーテル
英語名
1,4-Butanediol diglycidyl ether
分子式
C10H18O4
分子量
202.25

名称と別名

1,4-Butanediol diglycidyl ether2425-79-81,4-Butane diglycidyl ether1,4-DiglycidyloxybutaneAraldit DY 026Butanediol diglycidyl ether1,4-Bis(glycidyloxy)butaneGrilonit RV 1806Tetramethylene glycol diglycidyl ether1,4-BIS(2,3-EPOXYPROPOXY)BUTANE1,4-Bis(2,3-epoxypropyloxy)butaneButane, 1,4-bis(2,3-epoxypropoxy)-
名称をさらに表示
1,4-ブタンジオールジグリシジルエーテル1,4-ブタンジイルビス(グリシジルエーテル)1,4-ビス(グリシジルオキシ)ブタン2,2'-[1,4-ブタンジイルビス(オキシメチレン)]ビス(オキシラン)2,2'-[1,4-ブタンジイルビス(オキシ)ビスメチレン]ビスオキシラン2,2'-[1,4-ブタンジイルビス(オキシメチレン)]ビスオキシラン2,2'-[(ブタン-1,4-ジイル)ビス(オキシメチレン)]ビスオキシランテトラメチレンビス(オキシメチレン)ビスオキシラン1,4-ビス[(オキシラン-2-イル)メトキシ]ブタン1,4-ジ(グリシジルオキシ)ブタン1,4-ブチレングリコールジグリシジルエーテル2,2'-(1,4-ブタンジイルビスオキシビスメチレン)ビスオキシラン2,2'-[テトラメチレンビス(オキシメチレン)]ビス(オキシラン)2,2'-[テトラメチレンビス(オキシメチレン)]ビスオキシラン1,4-ビス(オキシラニルメトキシ)ブタン1,4ブタンジオルジグリシジルエテルアルキレングリコールジグリシジルエーテル1,4-ジグリシジルオキシブタン1,4-ビス(2,3-エポキシプロポキシ)ブタンテトラメチレングリコールジグリシジルエーテルBDDE1,4-bis(oxiran-2-ylMethoxy)butane1,4-Diglycidloxybutane1,4-Butanediol diglycidyl ether >=95%

データベース識別子

CAS
2425-79-8、26951-52-0
PubChem CID
17046
DTXSID
DTXSID7024667
ChEMBL
CHEMBL1450123
UNII
E9MU425FIB
EC Number
219-371-7、608-023-3
Nikkaji
J42.721G

物性

構造計算による物性

XLogP
0
極性表面積
43.5 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
9
重原子数
14
形式電荷
0
複雑度
144

実験および物理化学的性質

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

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 件

10 to 50 mg/mL at 70 °F (NTP, 1992)

Solubility in water: miscible

Flash Point · 3 件

greater than 200 °F (NTP, 1992)

129 °C

129 °C

Boiling Point · 4 件

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 件

9.8 [mmHg]

Vapor pressure, kPa at 20 °C: 1.3

Physical Description · 4 件

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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)

危険有害性情報

Regulatory Information · 5 件

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.

REACH registered substance: 1,4-bis(2,3-epoxypropoxy)butane (EC: 219-371-7)

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

DOT LabelClass 9
Fire Hazards · 2 件

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.
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.

化学と産業

用途と製造

Uses · 4 件

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 件

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 件

Construction

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

応用分野 · 3 件

説明1,4-Butanediol diglycidyl ether is a reactive diluent in epoxy resins.

使用1,4-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

一般的な説明Clear pale yellow liquid.

調製方法

The compound results from condensation of butanediol with epichlorohydrin followed by dehydrochlorination with caustic.

関連反応

2 件
反応記録を作成
HRID 5034 の反応式
HRID 5034反応物としてuspto-grants-1993_09
HRID 373331 の反応式
HRID 373331生成物としてuspto-grants-1992_11

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
BUDGE
1,4-Butanediyl diglycidyl ether
tk10352
Butane-1:4-diol diglycidyl etherDTXSID7024667TK 10352CD 15006 AE9MU425FIBOxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-NSC-24834(Tetramethylenebis(oxymethylene))dioxirane

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

物理化学的性質

融点
-21 °C · -21 °C
沸点
266 °C · 266 °C (lit.)
比重(密度)
1.1 g/mL · 1.1 g/mL at 25 °C (lit.)
蒸気圧
10 mm · ~10 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.453
闪点
230 °F · >230 °F
貯蔵温度
2 · Inert atmosphere,2-8°C
溶解性
Chloroform (Soluble), Methanol (Slightly)
外見
液体
比重
1.07 · 1.07
色
クリアイエロー
水溶解度
溶ける
BRN
115238 · 115238
安定性
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 データベース
2425 · 2425-79-8(CAS DataBase Reference)
NISTの化学物質情報
2 · Oxirane, 2,2'-[1,4-butanediylbis(oxymethylene)]bis-(2425-79-8)
EPAの化学物質情報
1 · 1,4-Butanediol diglycidyl ether (2425-79-8)

化学的性質

化学的特性Clear yellow liquid

Reactive GroupEthers
EC ClassificationSymbol: Xn; R: 20/21-36/38-43; S: (2)-26-28-37/39
Special Reports · 2 件

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 件

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.

安全と保護具

Fire Fighting · 2 件

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 件

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 件

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 件

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 件

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 件

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.

毒性情報

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 件

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

Burning sensation. Sore throat.

TSCA Test Submissions · 3 件

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 件

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 件

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

法規制情報

TSCA Requirements · 2 件

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.

安全データ

F
3-10
wgk
1
tsca
TSCA listed
rtecs
EJ5100000
毒性
LD50 oral in rat: 1134mg/kg
hs_code
29109000
risk_code
20/21-36/38-43-52/53-22
化審法
(2)-396
安衛法
変異原性物質
消防法
危-4-3-III
hazard_code
Xn
safety_code
26-28-37/39-28B
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Irrit. 2Skin Sens. 1
ストレージクラス
10 - Combustible liquids
有毒物質データの
2425-79-8(Hazardous Substances Data)

上流・下流製品情報

上流原料

エピクロロヒドリン1,4-ブタンジオール