Tetraethylenepentamine

HCID 8197CAS 112-57-2

基本情報

標準SMILES
NCCNCCNCCNCCN
InChIKey
FAGUFWYHJQFNRV-UHFFFAOYSA-N
分子式
C8H23N5
平均分子量
189.3 g/mol
単同位体質量
189.19534574

概要

Tetraethylenepentamine appears as a viscous liquid. Slightly less dense than water. Vapors heavier than air. Corrosive to the eyes, skin, mouth, throat and stomach. Vapors irritate the eyes and corrosive to the upper respiratory tract. Vapors may irritate the eyes. Flash point 325 °F.

名称と識別子

優先名称
Tetraethylenepentamine
IUPAC
N'-[2-[2-(2-aminoethylamino)ethylamino]ethyl]ethane-1,2-diamine
現地名
テトラエチレンペンタミン
英語名
Tetraethylenepentamine
分子式
C8H23N5
分子量
189.3

名称と別名

TETRAETHYLENEPENTAMINE112-57-2Tetren1,4,7,10,13-PentaazatridecaneTetraethylene pentamineTetraethylpentylamine1,11-Diamino-3,6,9-triazaundecane3,6,9-TriazaundecamethylenediamineDEH 263,6,9-Triazaundecane-1,11-diamineAncamine TEPATETRAEN
名称をさらに表示
テトラエチレンペンタミンN,N''-(イミノビスエチレン)ビス(エチレンジアミン)イミノビス(エチレンイミノエチレン)ジアミンテトラエチレンペンタアミンN-(2-アミノエチル)-N'-[2-(2-アミノエチルアミノ)エチル]-1,2-エタンジアミンN-(2-アミノエチル)-N'-[2-[(2-アミノエチル)アミノ]エチル]-1,2-エタンジアミン2,2'-イミノビス(エチレンイミノ)ビス(エタンアミン)1,4,7,10,13-ペンタアザトリデカンテトレン2,2'-[イミノビス(エチレンイミノ)]ビス(エタンアミン)3,6,9-トリアザウンデカン-1,11-ジアミンN-[2-[2-(2-アミノエチルアミノ)エチルアミノ]エチル]エタン-1,2-ジアミンN,N''-(イミノビスエチレン)ビス(1,2-エタンジアミン)3,6,9-トリアザ-1,11-ウンデカンジアミン2,2'-[イミノビス(エチレンイミノ)]ビスエタンアミン2,2'-イミノビス(2,1-エタンジイルイミノ)ビス(エタンアミン)ビス[2-(2-アミノエチルアミノ)エチル]アミンテトラエチルペンチルアミン3,6,9-トリアザウンデカン-1,11-ジアミン (テトラエチレンペンタミン)3,6,9-トリアザウンデカン-1,11-ジアミン (別名 テトラエチレンペンタミン)TetraethyenepentamineN1-(2-aMinoethyl)-N2-(2-((2-aMinoethyl)aMino)ethyl)ethane-1,2-diaMine2-Ethanediaminedeh26TETRENED.E.H. 26Texlin 400
DTXSID7026108YZD1C9KQ28INSULCURE 91,2-Ethanediamine, N-(2-aminoethyl)-N'-[2-[(2-aminoethyl)amino]ethyl]-NSC-886031,2-Ethanediamine, N-(2-aminoethyl)-N'-(2-((2-aminoethyl)amino)ethyl)-DTXCID006108CHEBI:49798

データベース識別子

CAS
112-57-2、26913-06-4、27233-92-7
PubChem CID
8197
DTXSID
DTXSID7026108
ChEMBL
CHEMBL138297
ChEBI
CHEBI:49798
UNII
YZD1C9KQ28
EC Number
203-986-2、608-018-6、682-669-4
Nikkaji
J5.129B

物性

構造計算による物性

XLogP
-2.9
極性表面積
88.1 Ų
水素結合供与体数
5
水素結合受容体数
5
回転可能結合数
10
重原子数
13

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Amines, Aliphatic

Corrosives

Drugs · 2 件

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Listed in ZINC15

pHALKALINE
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 件

log Kow= 1.503

-3.16 (calculated)

OdorAMMONIACAL; DIAGREEABLE, PENETRATING

物理化学的性質

融点
-40 °C · -40 °C (lit.)
沸点
340 °C · 340 °C
比重(密度)
0.998 g/mL · 0.998 g/mL at 25 °C (lit.)
蒸気密度
6.53 · 6.53 (vs air)
蒸気圧
0.01 mm · <0.01 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.505(lit.)

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, P273, 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, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1834) of reports.

Danger

H302+H312 (10.6%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]

危険有害性情報

Regulatory Information · 4 件

Chemical: 1,2-Ethanediamine, N-(2-aminoethyl)-N'-[2-[(2-aminoethyl)amino]ethyl]-

1,2-Ethanediamine, N1-(2-aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Ethanediamine, N1-(2-aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]- 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)

Tetraethylenepentamine: Does not have an individual approval but may be used under an appropriate group standard

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 - Selected linear polyethyleneamines: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 3 件

Special Hazards of Combustion Products: Ammonia and toxic oxides of nitrogen may form in fires. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialSlight, when exposed to heat or flame.
Health Hazards · 2 件

Inhalation may cause nausea and slight irritation; compound is a sensitizer, and prolonged contact may cause asthma. Ingestion can cause burns of mouth, esophagus, and possibly stomach. Contact with eyes or skin may cause burns. Repeated skin contact may cause dermatitis. (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 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use dry powder, carbon dioxide, water in large amounts, foam.

First Aid Measures · 4 件

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Put clothes in sealable container. Refer immediately for medical attention.

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

Rinse mouth. Do NOT induce vomiting. 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 · 2 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:

Safe StorageProvision to contain effluent from fire extinguishing. Separated from strong acids, strong oxidants, chlorinated hydrocarbons and food and feedstuffs. Dry. Store in an area without drain or sewer access.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: An estimated Koc value of 3.6(1,SRC) for tetraethylenepentamine indicates high mobility in soil(2) and leaching may occur(SRC). However, tetraethylenepentamine will exist primarily as a cation under environmental conditions (pH 5-9) and no experimental data are available which suggest whether it will adsorb to soil more strongly than its estimated Koc value indicates. Volatilization from moist soils is not expected to be rapid based upon a low Henry's Law constant. Amines are potentially susceptible to hydrolysis(1). Therefore, tetraethylenepentamine is expected to hydrolyze in moist soils; however, no rates were located(SRC). Furthermore, no data were located which suggest biodegradation is an important terrestrial fate process of tetraethylenepentamine(SRC).

AQUATIC FATE: Based on an estimated Henry's Law constant of 3.0X10-20 atm-cu m/mole at 25 °C(2), tetraethylenepentamine is expected to be essentially nonvolatile from water(1). An estimated Koc of 3.6 and BCF of 4.2 suggest that adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processes for tetraethylenepentamine in water systems(1). Based on pKa1, pKa2, pKa3, pKa4, and pKa5 values of 9.68, 9.10, 8.08, 4.72, and 2.98(3), respectively, tetraethylenepentamine will exist primarily as a cation under environmental conditions (pH 5-9). However, no experimental data are available which suggest whether it will adsorb to sediment more strongly than its estimated Koc value indicates. Amines are potentially susceptible to hydrolysis(4). Therefore, tetraethylenepentamine may hydrolyze in aquatic environments, but no rates were located(SRC). Furthermore, no data were located which suggest biodegradation is an important environmental fate process of tetraethylenepentamine in aquatic systems(SRC).

ATMOSPHERIC FATE: Based on a measured vapor pressure of 8.0X10-7 mm Hg at 25 °C(1), tetraethylenepentamine may exist in both the particulate and vapor phases in the ambient atmosphere(3). Vapor phase tetraethylenepentamine is degraded in the ambient atmosphere by reaction with photochemically formed hydroxyl radicals; the half-life for this reaction in air can be estimated to be about 1.2 hrs(2,SRC). Particulate phase tetraethylenepentamine may be susceptible to dry deposition. Also, based on its complete water solubility at 20 °C(4), removal from air via wet deposition is likely to occur(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesSerious local effects by all routes of exposure.
Signs and Symptoms · 4 件

Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing.

Redness. Pain. Skin burns.

Redness. Pain. Burns.

Burns in mouth and throat. Burning sensation in the throat and chest. Shock or collapse.

ICSC Environmental DataThe substance is toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment.
Soil Adsorption/Mobility · 1 件

Based on an estimated log Kow of -1.503(2) and a recommended regression derived equation(1), the Koc for tetraethylenepentamine can be estimated to be about 3.6(SRC). This Koc value suggests that tetraethylenepentamine will be highly mobile in soil and sediment(4). Based on pKa1, pKa2, pKa3, pKa4, and pKa5 values of 9.68, 9.10, 8.08, 4.72, and 2.98(3), respectively, tetraethylenepentamine will exist primarily as a cation under environmental conditions (pH 5-9); no experimental data are available which suggest whether the cation will adsorb more strongly than its estimated Koc value indicates(SRC).

法規制情報

FDA RequirementsTetraethylenepentamine is an indirect food additive for use only as a component of adhesives.

安全データ

F
21
wgk
2
tsca
TSCA listed
rtecs
KH8585000
ridadr
UN 2320
毒性
LD50 orally in Rabbit: 3990 mg/kg LD50 dermal Rabbit 660 mg/kg

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

Uses · 5 件

Used to make oil and fuel additives, paints, and asphalt adhesives; [INCHEM] Used as an epoxy resin hardener; [Reference #1] Used as a solvent for acid gases, resins, and dyes; Also used as a chemical intermediate and in paper manufacturing; [AIHA]

Pulp and Paper Processing [Category: Industry]

SOLVENT FOR SULFUR, ACID GASES, VARIOUS RESINS & DYES; SAPONIFYING AGENT FOR ACIDIC MATERIALS

CHEM INT FOR LUBRICATING OIL ADDITIVES & SURFACTANTS, CASTOR OIL ADDUCTS USED AS EMULSIFIERS, IMIDAZOLINE COMPOUNDS, VWT-STRENGTH RESINS, & REACTIVE POLYAMIDE HARDENERS IN EPOXY RESINS; COAGULATION AID FOR SYNTHETIC RUBBER LATEXES.

In papermaking

U.S. Exports · 2 件

(1978) 1.96X10+9 GRAMS

(1979) 1.88X10+9 GRAMS

U.S. Production · 3 件

2023: 4,000,000 - <5,500,000 lb

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Industry UsesEmulsifier
Methods of ManufacturingREACTION OF AQUEOUS AMMONIA WITH 1,2-DICHLOROETHANE FOLLOWED BY NEUTRALIZATION (EG, WITH AQUEOUS CAUSTIC SODA) AND FRACTIONAL DISTILLATION
Household ProductsInformation on 10 consumer products that contain Tetraethylenepentamine in the following categories is provided:
応用分野 · 3 件

用途ポリアミド、湿潤紙力増強用アミノ樹脂、ニトロセルロース乳化剤、合成潤滑油等の原料、エポキシ樹脂硬化剤

使用Solvent for sulfur, acid gases, and various resins and dyes; saponifying agent for acidic materials; manufacture of synthetic rubber; dispersant in motor oils; intermediate for oil additives.

一般的な説明A viscous liquid. Slightly less dense than water. Vapors heavier than air. Corrosive to the eyes, skin, mouth, throat and stomach. Vapors irritate the eyes and corrosive to the upper respiratory tract. Vapors may irritate the eyes. Flash point 325°F.

調製方法 · 1 件

純化方法Distil the amine under vacuum. Also purify via its penta hydrochloride, nitrate or sulfate. Jonassen, Frey and Schaafsma [J Phys Chem 61 504 1957] cooled a solution of 150g of the base in 300mL of 95% EtOH, and added dropwise 180mL of conc HCl, keeping the temperature below 20o. The white precipitate was filtered off, crystallised three times from EtOH/water, then washed with diethyl ether and dried by suction. Reilley and Holloway [J Am Chem Soc 80 2917 1958], starting with a similar solution cooled to 0o, added slowly (keeping the temperature below 10o) a solution of 4.5g-moles of HNO3 in 600mL of aqueous 50% EtOH (also cooled to 0o). The precipitate was filtered by suction, recrystallised five times from aqueous 5% HNO3, then washed with acetone and absolute EtOH and dried at 50o. [For purification via the sulfate see Reilley and Vavoulis (Anal Chem 31 243 1959), and for an additional purification step using the Schiff base with benzaldehyde see Jonassen et al. J Am Chem Soc 79 4279 1957]. [Beilstein 4 IV 1244.]

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