ジエチレントリアミン

Diethylenetriamine

HCID 8111CAS 111-40-0

基本情報

標準SMILES
NCCNCCN
InChIKey
RPNUMPOLZDHAAY-UHFFFAOYSA-N
分子式
C4H13N3
平均分子量
103.17 g/mol
単同位体質量
103.11094742

概要

Diethylenetriamine appears as a yellow liquid with an ammonia-like odor. Less dense than water. Corrosive to metals and tissue. Vapors heavier than air. Burns, although possibly difficult to igntie. Toxic oxides of nitrogen produced during combustion. Used as a solvent for plastics and dyes and in chemical synthesis.

名称と識別子

優先名称
Diethylenetriamine
IUPAC
N'-(2-aminoethyl)ethane-1,2-diamine
現地名
ジエチレントリアミン
英語名
Diethylenetriamine
分子式
C4H13N3
分子量
103.17

名称と別名

DIETHYLENETRIAMINE111-40-0Bis(2-aminoethyl)amine2,2'-Diaminodiethylamine1,4,7-TriazaheptaneDETADiethylene triamineBarsamide 115Epicure TAncamine DETA3-Azapentane-1,5-diamineAminoethylethandiamine
名称をさらに表示
ジエチレントリアミン2-[(2-アミノエチル)アミノ]エタンアミン2,2'-イミノビス(エタン-1-アミン)2,2'-イミノビス(エタンアミン)N-(2-アミノエチル)-1,2-エタンジアミン2,2'-イミノビスエタンアミン1,5-ジアミノ-3-アザペンタン1,4,7-トリアザヘプタン3-アザペンタン-1,5-ジアミン2,2'-イミノジエタンアミン2,2'-イミノジ(エタンアミン)2,2'-ジアミノジエチルアミンイミノビス(エチレン)ジアミンビス(2-アミノエチル)アミンビス-(2-アミノ-エチル)-1,2-エチレンジアミンジエチレントリアミン, 99%ジ(2-アミノエチル)アミンN -(2-アミノエチル)-1 ,2-エタンジアミンジエチレン トリアミン)N1-(2-aMinoethyl)ethane-1,2-diaMineDIENDIETHYLENTRIAMINEDETA DiethylenetriamineDiethylenetriamindiethylenetriamine(deta)
N,N-Bis(2-aminoethyl)amine1,5-Diamino-3-azapentaneImino-bis-ethylamine1,2-Ethanediamine, N-(2-aminoethyl)-ChS-P 12,2'-Iminobis(ethanamine)N-(2-Aminoethyl)-1,2-ethanediamineBis(beta-aminoethyl)amine

データベース識別子

CAS
111-40-0、75037-24-0
PubChem CID
8111
DTXSID
DTXSID2025050
ChEMBL
CHEMBL303429
ChEBI
CHEBI:30629
UNII
03K6SX4V2J
EC Number
203-865-4、616-182-5
Nikkaji
J5.108J

物性

構造計算による物性

XLogP
-2.1
極性表面積
64.1 Ų
水素結合供与体数
3
水素結合受容体数
3
回転可能結合数
4
重原子数
7

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Amines, Aliphatic

Corrosives

pHSTRONGLY ALKALINE
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 件

-1.3

-1.3

Odor · 2 件

AMMONIACAL ODOR

... Strong, ammonia-like odor ...

Food AdditivesPROCESSING AID -> FDA Substance added to food

物理化学的性質

融点
-40 °C · -40 °C
沸点
206 °C · 206 °C
比重(密度)
0.955 g/mL · 0.955 g/mL at 25 °C(lit.)
蒸気密度
3.6 · 3.6 (vs air)
蒸気圧
0.08 mm · 0.08 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.484(lit.)

化学的性質

化学的特性Diethylenetriamine is a corrosive yellow liquid and a solvent. It has a strong ammonia odor and is prone to absorbing moisture. It can dissolve in water, acetone, benzene, ether, methanol, but is not soluble in n-heptane.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 3716) of reports.

Danger

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 5 件

Chemical: 1,2-Ethanediamine, N-(2-aminoethyl)-

1,2-Ethanediamine, N1-(2-aminoethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Ethanediamine, N1-(2-aminoethyl)- 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)

Status: Active Update: 14-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15883

Diethylene triamine: HSNO Approval: HSR002966 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1,2-Ethanediamine, N-(2-aminoethyl)-: Environment tier I assessment
DOT LabelCorrosive
Fire Hazards · 3 件

Special Hazards of Combustion Products: Irritating vapors are generated when heated. (USCG, 1999)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 97 °C explosive vapour/air mixtures may be formed.

Fire PotentialLOW, WHEN EXPOSED TO HEAT OR FLAME
Health Hazards · 2 件

Prolonged breathing of vapors may cause asthma. Liquid burns skin and eyes. A skin rash can form. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer immediately for medical attention .

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

Rinse mouth. Do NOT induce vomiting. Rest. Refer immediately for medical attention.

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 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.

General First Aid:

(General first aid procedures)

Safe StorageSeparated from strong oxidants, acids, organic nitro compounds and food and feedstuffs. Keep in a well-ventilated room.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Target OrgansEyes, skin, respiratory system
Environmental Fate · 3 件

TERRESTRIAL FATE: If released on land, diethylenetriamine would principally leach into the ground. The only circumstance where biodegradation would be significant is where the microorganisms at the site are well acclimated. Some of the diethylenetriamine may volatilize from the soil surface. (SRC)

AQUATIC FATE: The fate of diethylenetriamine released into water is unknown. Volatilization and adsorption to sediment will not be significant loss mechanisms. Biodegradation would not be expected to be significant unless the microorganisms at the site were well acclimated. (SRC)

ATMOSPHERIC FATE: Diethylenetriamine emitted to the atmosphere will degrade by reaction with photochemically produced hydroxyl radicals. The estimated half-life for this reaction is 2.7 hr(1,SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 5 件

Sore throat. Cough. Burning sensation. Laboured breathing. Symptoms may be delayed.

Pain. Serious skin burns.

Pain. Severe deep burns. Loss of vision.

Burning sensation. Abdominal pain. Shock or collapse.

irritation eyes, skin, mucous membrane, upper respiratory system; dermatitis, skin sensitization; eye, skin necrosis; cough, dyspnea (breathing difficulty), pulmonary sensitization

ICSC Environmental DataEnvironmental effects of the substance have been adequately investigated, but no significant effects have been found.

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. Diethylenetriamine is included on this list.

安全データ

OEB
B
OEL
TWA: 1 ppm (4 mg/m3) [skin]
wgk
2
tsca
TSCA listed
rtecs
IE1225000
ridadr
UN 2079

化学と産業

薬理情報

Mechanism of Action... The mechanism of action /for pulmonary or dermal sensitization/ is probably a cross-linking of proteins with bifunctional amine groups.
MeSH Pharmacological Classification · 1 件

A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81)

Absorption, Distribution and Excretion · 1 件

Diethylenetriamine is readily absorbed through the gastrointestinal tract and 96% of the administered dose is excreted withing 48 hr. Roughly equal amounts are excreted in the feces and urine with at least 4 metabolites being detected (but not identified) in the latter. Only a small proportion (<2%) was recovered as expired carbon dioxide. Any residual remaining in the animal was found primarily in kidney, liver, bladder and large intestine.

Cellular LocationsCytoplasm

用途と製造

Uses · 6 件

Used as a solvent, fuel component, and saponification agent; [ACGIH] Used in the production of epoxy resin curing agents and reactive polyamide resins; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

CHEM INT FOR REACTIVE POLYAMIDE RESINS, FATTY AMINOAMIDES, FATTY IMIDAZOLINES.

SOLVENT FOR SULFUR, ACID GASES, VARIOUS RESINS, DYES; SAPONIFICATION AGENT FOR ACIDIC MATERIALS.

In the synthesis of polymer antistatic agents for textiles

In synthesis of 2-part epoxy amine hardeners

U.S. Production · 4 件

2023: 50,000,000 - <100,000,000 lb

(1972) 1.47X10+10 G

(1974) 1.47X10+10 G (SALES)

(1992) 38,941,000 kgs

Consumer UsesHardener
Industry UsesNot Known or Reasonably Ascertainable
Methods of ManufacturingREACTION OF ETHYLENE DICHLORIDE AND AMMONIA
Formulations/PreparationsGrade: Technical
応用分野 · 7 件

解説ジエチレントリアミン (英: Diethylenetriamine) とは、化学式C4H13N3、示性式HN(CH2CH2NH2)2であらわされる有機化合物です。 一級アミンに分類される化合物であり、別名には、2,2′-イミノジエチルアミン、2,2′-ジアミノジエチルアミン、ビス(2-アミノエチル)アミンなどの名称が有り、DETAと略されることもあります。CAS登録番号は、111-40-0です。 化学的性質はエチレンジアミンに類似しており、同じような用途で用いられます。分子骨格はジエチレングリコールに類似していると捉えられることもあります。

用途繊維関係(防しわ剤、界面活性剤、染料固着剤)、紙の湿潤強化剤、農薬関係(殺菌剤、殺虫剤、除草剤)、キレート剤、コーティング材、接着剤、イオン交換樹脂、ゴム薬品、ロケットの液体燃料、エポキシ樹脂硬化剤

用途有機合成原料。

用途繊維関係、農薬原料

説明Diethylenetriamine is a hardener in epoxy resins of the Bisphenol A type. It has been reported as a sensitizer in ultrasonic baths for cleaning jewels, in synthetic lubricants and in carbonless copy paper.

一般的な説明A yellow liquid with an ammonia-like odor. Less dense than water. Corrosive to metals and tissue. Vapors heavier than air. Burns, although possibly difficult to igntie. Toxic oxides of nitrogen produced during combustion. Used as a solvent for plastics and dyes and in chemical synthesis.

使用用途ジエチレントリアミンの主な使用用途は、紙湿潤強化剤、エポキシ樹脂硬化剤、、、繊維処理剤、有機合成材料などです。このうち紙湿潤強化剤は、最も多くのジエチレントリアミンを消費している用途です。 ジエチレントリアミンをと反応させ、エピクロルヒドリンを付加することによって合成されるポリアミド樹脂に使用されています。繊維処理剤としては、防しわ剤、界面活性剤、染料固着剤などの製品があります。 また、農薬関係では、殺菌剤、殺虫剤、除草剤などの用途でも用いられる物質です。特に身近な使用用途としては、エポキシ樹脂系のや熱硬化樹脂の硬化剤が挙げられます。これらの製品はジエチレントリアミンがエポキシド基と反応することによって、架橋構造が形成される原理を利用したものです。

調製方法

Diethylenetriamine is produced by the reaction of ethylene dichloride with ammonia. Diethylenetriamine is used in biological studies, for polyamines inhibition to carbonic anhydrases by anchoring to the zinc-coordinated water molecule.

純化方法Dry the amine with Na and distil, preferably under reduced pressure, or in a stream of N2. [Beilstein 4 IV 1284.]

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