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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 78.6
実験および物理化学的性質
Chemical Classes
Nitrogen Compounds -> Amines, Aliphatic
Corrosives
Drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Listed in ZINC15
LogP
log Kow= 1.503
-3.16 (calculated)
Density
0.998 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9980 @ 20 °C/20 °C
Bulk density 8.3 lb/gal
Relative density (water = 1): 0.99
0.998 @25 °C
Viscosity
96.2 cP @ 20 °C
96.9 mm²/s at 20 °C
Color/Form
VISCOUS, HYGROSCOPIC LIQUID
Yellow liquid
Solubility
greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
SOL IN MOST ORGANIC SOLVENTS & WATER
Solubility in water: miscible
Flash Point
325 °F (NTP, 1992)
163 °C
325 °F (163 °C) (OPEN CUP)
163 °C o.c.
Boiling Point
644 °F at 760 mmHg (NTP, 1992)
340.30 °C @ 760 MM HG
320 - 340 °C
333 °C @760 [mm Hg]
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.)
- 闪点
- 365 °F · 365 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 6540 g/リットル · 6540g/リットル
- 外見
- 液体
- 酸解離定数(Pka)
- 1 · pK1:2.98(+5);pK2:4.72(+4);pK3:8.08(+3);pK4:9.10(+2);pK5:9.67(+1) (25°C,)
- 色
- クリア
- PH
- 11.8 · 11.8 (20g/l, H2O, 20℃)
- 臭い (Odor)
- アンモニア臭
- 爆発限界(explosive limit)
- 0.1 · 0.1-15%(V)
- 水溶解度
- 溶ける
- BRN
- 506966 · 506966
- Henry's Law Constant
- 3.3 · 3.3×1014 mol/(m3Pa) at 25℃, HSDB (2015)
- 安定性
- 安定。可燃性。強力な酸化剤、鉱酸、ハロゲン化炭化水素、過酸化水素とは相容れない。
- InChI
- 1S/C8H23N5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h11-13H,1-10H2
- InChIKey
- FAGUFWYHJQFNRV-UHFFFAOYSA-N
- SMILES
- NCCNCCNCCNCCN
- CAS データベース
- 112 · 112-57-2(CAS DataBase Reference)
- NISTの化学物質情報
- Tetraethylenepentamine(112-57-2)
- EPAの化学物質情報
- Tetraethylenepentamine (112-57-2)
安全と法規制
GHS分類
GHS Classification
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
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.)
Fire Hazards
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.
Health Hazards
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.
Hazards Summary
Highly irritating to eyes and skin; [HSDB] May cause skin sensitization and asthma after prolonged contact; [CAMEO] Corrosive to eyes and skin; A skin sensitizer; [CHEMINFO] Inhalation of high concentrations may cause pneumonitis and pulmonary edema; [MSDSonline] Danger of cutaneous absorption; A potential skin sensitizer; Occupational asthma not mentioned under Human Use and Experience; [AIHA]
安全と保護具
Fire Fighting
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Use dry powder, carbon dioxide, water in large amounts, foam.
First Aid Measures
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
· 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
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:
Fire Fighting Procedures
WATER OR FOAM MAY CAUSE FROTHING. "ALCOHOL" FOAM.
If material /is/ involved in /a/ fire use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
Spillage Disposal
Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures
If material /is/ not involved in /a/ fire keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.
Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Avoid bodily contact with material.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Isolation and Evacuation
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Immediate precautionary measure
毒性情報
Environmental Fate
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).
Signs and Symptoms
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.
Soil Adsorption/Mobility
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).
Artificial Pollution Sources
Tetraethylenepentamine's use as a solvent for sulfur, acid gases, various resins and dyes, as a saponifying agent for acidic materials, in the manufacture of synthetic rubber, as a dispersant in motor oils, and as an intermediate for oil additives(1) indicates that it may be released to the environment in waste streams from its production and use(SRC).
Environmental Bioconcentration
Based on an estimated log Kow of -1.503(2), the BCF for tetraethylenepentamine can be estimated to be 4.2(SRC) using a recommended regression derived equation(1). This BCF value suggests that tetraethylenepentamine would not bioconcentrate in aquatic organisms(SRC).
Volatilization from Water/Soil
The Henry's Law constant for tetraethylenepentamine can be estimated to be approximately 3X10-20 atm-cu m/mole at 25 °C using a chemical structure estimation method(1,SRC). This value of Henry's Law constant suggests that tetraethylenepentamine is essentially nonvolatile from water(2).
Non-Human Toxicity Excerpts
FIVE DROPS OF LIQ IN EYES OF RABBITS CAUSES SEVERE BURNS.
Tetraethylenepentamine was found to be positive when tested for mutagenicity using the Salmonella/ microsome preincubation assay, using the standard protocol approved by the National Toxicology Program. Tetraethylenepentamine was tested at doses of 0.033, 0.100, 0.333, 1.000, 3.333, in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.033, 0.100, 0.333, 1.000, 3.333, 6.666, and 10.000 mg/plate. The lowest positive dose tested in any Salmonella typhimurium strain was 0.100 mg/plate in strain TA100 without activation. At this dose the number of revertants per plates approached double the controls. The compound was also positive in TA100 with activation and in TA98 both with and without activation.
Produces intense skin irritation and moderate eye injury in rabbits but not so severe as lower homologues.
Dermal oncogenicity of four ethyleneamines was investigated in male C3H mice. The compounds were diethylenetriamine in high purity and commercial samples, triethylenetetramine, tetraethylenepentamine, and a residue mixture of ten carbon and higher polymeric amines, polyamine-HPA-No-2. Groups of 50 C3H/HeJ mice were treated on their backs, three times a week for their complete life span, with applications of 25 ul of one of the substances. Hair was clipped from the treatment areas once a week. Approximate doses were 1.25 mg for high purity diethylenetriamie, commercial diethylenetriamine, and triethylenetetramine, 6.25 mg for tetraethylenepentamine, and 2.5 mg for HPA-No-2. Mean survival time was 587 to 662 days for the five groups of treated mice and 626 days for water treated controls. No epidermal tumors were seen except for a papilloma on the upper lip of one mouse in the triethylenetetramine group, but this was not considered to be treatment related because of its location. Three other cutaneous or subcutaneous neoplasms (two in treated groups, one in the control group) were considered to be spontaneous. Twenty cases of hyperkeratosis and 13 of epidermal necrosis were observed in the tetraethylenepentamine group, indicating that tetraethylenepentamine induced irritation, but there was no epidermal hyperplasia or dermal fibrosis. Absence of irritation in the other groups probably resulted from the lower doses used. It was concluded that there is no evidence of an oncogenic effect of any member of the tested series of ethyleneamines under the conditions studied.
Environmental Abiotic Degradation
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). The rate constant for the vapor-phase reaction of tetraethylenepentamine with photochemically produced hydroxyl radicals can be estimated to be 3.06X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 1.2 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(2). Amines are potentially susceptible to hydrolysis(4). Therefore, tetraethylenepentamine is expected to hydrolyze; however, no rates were located(SRC).
法規制情報
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
- PRTR法
- 第一種指定化学物質
- hs_code
- 29212900
- risk_code
- 21/22-34-43-51/53
- 化審法
- (2)-162
- 安衛法
- 57,57-2
- 消防法
- 危険物第4類第三石油類(水溶性)
- hazard_code
- C,N
- safety_code
- 26-36/37/39-45-61
- hazard_class
- 8
- packing_group
- III
- 毒劇物取締法
- 劇物
- 自然発火温度
- 610 °F
- 環境リスク評価
- テトラエチレンペンタミン(112-57-2)
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1BSkin Sens. 1
- ストレージクラス
- 8A - Combustible corrosive hazardous materials
- 有毒物質データの
- 112-57-2(Hazardous Substances Data)
化学と産業
薬理情報
用途と製造
Uses
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
(1978) 1.96X10+9 GRAMS
(1979) 1.88X10+9 GRAMS
U.S. Production
2023: 4,000,000 - <5,500,000 lb
(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
General Manufacturing Information
Plastics Material and Resin Manufacturing
1,2-Ethanediamine, N1-(2-aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]-: ACTIVE
応用分野
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
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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