乙二胺

Ethylenediamine

HCID 3301CAS 107-15-3

基本信息

标准SMILES
NCCN
InChIKey
PIICEJLVQHRZGT-UHFFFAOYSA-N
分子式
C2H8N2
平均分子量
60.1 g/mol
单同位素质量
60.06874826

概述

Ethylenediamine appears as a clear colorless liquid with an ammonia-like odor. Flash point of 91 °F and a melting point of 47 °F. Corrosive to tissue. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion. Density 7.5 lb / gal. Used to make other chemicals and as a fungicide.

名称与标识

首选名称
Ethylenediamine
IUPAC
ethane-1,2-diamine
中文名
乙二胺
英文名
Ethylenediamine
分子式
C2H8N2
分子量
60.1

名称与别名

ethylenediamineEthane-1,2-diamine107-15-31,2-Diaminoethane1,2-EthanediamineEthylene diamineEthylendiamineedamineDimethylenediamine1,2-EthylenediamineAethaldiaminAethylenediamin
展开更多名称
乙二胺双酮嗪乙亚胺乙烯二胺乙撑二胺二氨基乙烷2-乙二胺水中乙二胺[伸]乙二胺抗癌-161EDADiaminoethaneH2NCH2CH2NH21,2-Diaminoethan
EthyleendiamineEthylene-diaminebeta-Aminoethylamine1,2-DiaminoaethanAlgicode 106LAmerstat 2741,2-Diamino-ethaan1,2-Diamino-ethano

数据库标识

CAS
107-15-3
PubChem CID
3301
DTXSID
DTXSID5021881
ChEMBL
CHEMBL816
ChEBI
CHEBI:30347
UNII
60V9STC53F
EC Number
203-468-6
Nikkaji
J4.057F

性质

结构计算性质

XLogP
-2
极性表面积
52 Ų
氢键供体
2
氢键受体
2
可旋转键
1
重原子
4

实验与物化性质

Chemical Classes · 2 条

Nitrogen Compounds -> Amines, Aliphatic

Corrosives

DrugsPharmaceuticals -> Listed in ZINC15
pH11.9 @ 25 °C (25% soln)
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 3 条

log Kow = -2.04 @ pH 13

-2.04

-1.2

物理化学性质

熔点
8.5 °C · 8.5 °C (lit.)
沸点
118 °C · 118 °C (lit.)
密度
0.899 g/mL · 0.899 g/mL at 25 °C (lit.)
蒸气密度
2.07 · 2.07 (vs air)
蒸气压
10 mm · 10 mm Hg ( 20 °C)
折射率
20 · n20/D 1.4565(lit.)

化学性质

无色透明的粘稠液体,有氨臭。 能溶于水和乙醇,微溶于乙醚,不溶于苯。

安全与法规

GHS分类

GHS Classification · 6 条

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P342+P316, P362+P364, P363, P370+P378, P403, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2078) of reports.

Danger

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

危害信息

Regulatory Information · 6 条

Chemical: 1,2-Ethanediamine

Hazard Traits - Respiratory Toxicity

Commission Regulation No 844/2012

1,2-Ethanediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Ethanediamine 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: 02-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15765

Substance: Ethylenediamine

Other Safety InformationIMAP assessments - 1,2-Ethanediamine: Environment tier I assessment
DOT LabelCorrosive Flammable Liquid
Fire Hazards · 3 条

Burning rate: 2.2 mm/minute. When exposed to heat or flame, the material has a moderate fire potential. The material can react readily with oxidizing materials. Containers may explode in heat of fire. Material emits nitrogen oxides when burned. Avoid carbon disulfide, silver perchlorate, imines, oxidizing materials. Stable. Hazardous polymerization may not occur. (EPA, 1998)

· Flammable/combustible material.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 34 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2 条

FLAMMABLE LIQUID WHEN EXPOSED TO HEAT, FLAME OR OXIDIZERS.

Contact with ... chlorinated organic cmpd may cause fires ... .

Health Hazards · 2 条

Vapor inhalations at a concentration of 200 ppm for 5 to 10 minutes will lead to nasal irritation and produce a tingling sensation. Inhalation at concentrations of 400 ppm or greater leads to severe nasal irritation. Respiratory irritation may result. Many individuals are hypersensitive to ethylenediamine exposure; therefore, safe threshold limits are difficult to set. (EPA, 1998)

· May cause toxic effects if inhaled or ingested.

安全与防护

Fire Fighting · 2 条

Wear full protective clothing including gloves and boots. If necessary to enter closed area, wear full-faced gas masks with self-contained breathing apparatus. Use water spray, dry chemical, alcohol foam, or carbon dioxide. Do not use water in case of drum or tank fires. If a leak or spill has not ignited, use water spray to reduce the vapors and dilute spills to nonflammable mixtures. Use water to keep fire-exposed containers cool. (EPA, 1998)

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 条

Fresh air, rest. Refer immediately for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention.

Accidental Release Measures · 2 条

· 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 条

Signs and Symptoms of Acute Ethylenediamine Exposure: Acute exposure to ethylenediamine may result in cough, difficulty in breathing, irritation of the lungs, and pneumonia. Nausea, vomiting, and diarrhea are often seen. Contact with ethylenediamine may result in redness, pain, irritation, and burns.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants, acids, chlorinated organic compounds and food and feedstuffs. Cool. Well closed. Store only in original container.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒理信息

Interactions · 2 条

Ethylenediamine (EDA) (31.6-1000 mg/kg, ip) inhibited the convulsive effects of pentylenetetrazol (100 mg/kg, ip) in mice. EDA (100-1000 mg/kg, ip) incr the convulsion threshold to the iv infusion of 3 convulsants in the order pentylenetetrazol > bicuculline > strychnine.

A 37-yr-old pt sensitized to ethylenediamine by topical use of a steroid cream for scaly rash, developed an itchy morbilliform rash affecting the whole body following piperazine citrate therapy for threadworms.

Target OrgansSkin, respiratory system, liver, kidneys
Ecotoxicity Values · 5 条

LC50 Pimephales promelas (fathead minnow) 115.7 mg/l/96 hr @ 22 °C (95% confidence limit 98.6-131.6 mg/l) /Static bioassay/

TLM: ORYZIAS LATIPES 1000 MG/L/24 HR /CONDITIONS OF BIOASSAY NOT SPECIFIED/

Toxicity Threshold (Cell Multiplication Inhibition Test) Uronema parduczi Chatton-Lwoff (protozoa) 52 mg/l /Conditions of bioassay not specified/

Toxicity Threshold (Cell Multiplication Inhibition Test) Scenedesmus quadricauda (green algae) 0.85 mg/l /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for ETHYLENEDIAMINE (9 total), please visit the HSDB record page.

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 4766(2) indicates that ethylenediamine is expected to have slight mobility in soil(SRC). Volatilization of ethylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.73X10-9 atm-cu m/mole(3). The potential for volatilization of ethylenediamine from dry soil surfaces may exist based upon a vapor pressure of 12.1 mm Hg(4). However, adsorption to soil may attenuate volatilization(SRC). Based on screening studies(5-7), biodegradation is expected to be the most important degradation process for this compound but no experimental rates in soil are available. Ethylenediamine may also form stable complexes with metal ions(8) in soil, but again, experimental data are lacking(SRC).

AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 4766(2) indicates that ethylenediamine is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.73X10-9 atm-cu m/mole(4). As ethylenediamine has two primary amine groups, at the pH range found in most environmental waters, it is expected to be partially protonated; the dissociated form will not volatilize. According to a classification scheme(5), an estimated BCF of less than 1(SRC), from its log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Based on screening studies(8-10), biodegradation is expected to be the most important degradation process for this compound but no experimental rates in water are available. Complexation of ethylenediamine with transition metals(11) in the water or reaction with humic materials(12) is possible(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylenediamine, which has a vapor pressure of 12.1 mm Hg at 25 °C(2), is expected to exist solely as a vapor. Vapor-phase ethylenediamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.3x10-11 cu cm/molecule-sec at 25 °C(3) using a structure estimation method(3). As ethylenediamine is miscible in water(4), washout by rain will also be an important removal process(SRC).

Food Survey Values... Amines from decomposing fish ... /Amines/
Adverse EffectsDermatotoxin - Skin burns.

法规信息

FDA RequirementsEthylenediamine is an indirect food additive for use only as a component of adhesives.
Atmospheric Standards · 1 条

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethylenediamine is produced, as an intermediate or a final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 2 条

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Ethylenediamine is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 条

Ethylenediamine is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

DHS Chemicals of Interest (COI) · 4 条

Ethylenediamine

1

20000

Toxic chemical that can be released at a facility.

State Drinking Water Guidelines(FL) FLORIDA 10,000 ug/l

安全数据

F
10-34
wgk
2
tsca
TSCA listed
毒性
LD50 orally in rats: 1.16 g/kg (Smyth)
RTECS号
KH8575000
包装类别
II
毒性防护 · 3 条

急性毒性口服- 大鼠 LD50: 500 毫克/ 公斤; 吸入- 小鼠 LC50: 300 毫克/ 立方米

刺激数据皮肤- 兔子 10 毫克/ 24小时 重度; 眼睛- 兔子 0.75 毫克/ 24小时 重度

职业标准TWA 25毫克/ 立方米; STEL 35 毫克/ 立方米

包装储运 · 4 条

爆炸物危险特性与空气混合可爆

可燃性危险特性遇明火、高温、氧化剂较易燃; 燃烧产生有毒氮氧化物烟雾

储运特性库房通风低温干燥; 与氧化剂、酸类分开存放

灭火剂干粉、二氧化碳、泡沫、1211灭火剂

化学与工业

药理信息

Mechanism of Action · 2 条

Ethylenediamine (EDA) acted as a gamma-aminobutyric acid (GABA) agonist by enhancing (3)H-labeled diazepam binding to well-washed rat forebrain membrane prepn in a bicuculline-sensitive manner, although its potency was 700-800 fold less than that of gamma-aminobutyric acid. Ethylenediamine was more than 3750-fold weaker than gamma-aminobutyric acid as a displacer of (3)H-gamma-aminobutyric acid bound to membrane receptors & was more than 40-fold weaker than gamma-aminobutyric acid at (3)H-gamma-aminobutyric acid uptake sites. Its most potent action was as an inhibitor of beta-alanine uptake into rat cerebral cortex slices.

The release of (3)H gamma-aminobutyric acid (GABA) from Mueller (glial) cells was studied in the rat retina by a double isotope-labeling technique in which Mueller cells are preloaded with (3)H-gamma-aminobutyric acid while a population of neurons is prelabeled with (14)C-labeled glycine. The effects of 2 depolarizing agents, high K+ and veratridine, and the gamma-aminobutyric acid mimetic, ethylenediamine (EDA), on transmitter release from glial cells and neurons were simultaneously determined. Ethylenediamine released (3)H-gamma-aminobutyric acid readily, whereas little (14)C-glycine release was observed.

Biological Half-LifeEthylenediamine has a short half life of ~0.55 hours.
Metabolism/Metabolites · 1 条

Male rats were dosed with (14)C-ethylenediamine (EDA) at 5, 50, or 500 mg/kg by oral, endotracheal, and iv routes. Six to 9% of the admin radioactivity was eliminated via expired air in the form of (14)CO2. n-Acetylethylenediamine, a major metabolite, accounted for approx half of the urinary radioactivity. Depending on the dosage level, 2-49% of the radioactivity was unchanged parent cmpd. The route of admin did not appear to change the metabolic profile.

FDA Pharmacological Classification · 6 条

60V9STC53F

ETHYLENEDIAMINE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

Absorption, Distribution and Excretion · 6 条

After oral administration its bioavailability is about 0.34, due to a substantial first-pass effect.

Renal excretion of the unchanged substance amounts to only about 18% after intravenous and 3% after oral administration.

Vd = 0.133 l/kg

/Diamines/ are absorbed through the skin. /Diamines/

Male rats were dosed with (14)C-ethylenediamine (EDA) at 5, 50, or 500 mg/kg by oral, endotracheal, and iv routes. Urinary excretion was the primary route of elimination accounting for 42 to 65% of the admin radioactivity. Fecal excretion was 5-32%, depending upon the route. Six to 9% was eliminated via expired air in the form of CO2. At 48 hr, 11-21% of radioactivity remained in the various organs & the carcass. Thyroid, bone marrow, liver, and kidney contained relatively higher concn. The route of admin did not appear to change the metabolic profile. As the dosage incr from 5 to 50 to 500 mg/kg, there was a pattern of accumulation of ethylenediamine with a corresponding decr of metabolite formation.

Plasma concn of ethylenediamine (EDA) were examined after oral and iv admin of aminophylline (theophylline and ethylenediamine mixture) to 3 healthy subjects. Ethylenediamine was not detectable after 2 hr.

Tissue LocationsKidney

用途与制造

Uses · 6 条

Used in the manufacture of chelating agents, fungicides, waxes, polyamide resins, and corrosion inhibitors. [ACGIH] Used as an emulsifier, an inhibitor in antifreeze solutions, and an additive to pharmaceuticals and textile lubricants; [Merck Index] Used in photography (color developing baths); [www.ci.tucson.az.us/arthazards/medium.html]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

For Ethylenediamine (USEPA/OPP Pesticide Code: 004205) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Solvent for casein, albumin, shellac, and sulfur; emulsifier; stabilizing rubber latex; as inhibitor in antifreeze solutions; in textile lubricants; pharmaceutic aid (aminophylline injection stabilizer)

In prepn of dyes, synthetic waxes, resins, insecticides and asphalt wetting agents

Use in manuf of weed killers; use in manuf of surfactants, emulsifying agents, wetting agents, dispersants, corrosion inhibitors, detergents, and textile surface treatments

ImpuritiesThe ammonia-dichloroethane reaction yields the entire family of ethyleneamines: EDA, DEDA, DETA, TETA, TEPA, PEHA and AEP. The percent yield of each amine is determined by the ratio of dichloroethene to ammonia.
U.S. Exports · 3 条

(1972) 7.31X10+9 G

(1975) 1.43X10+9 G

(1984) 1.13X10+10 g

U.S. Imports · 3 条

(1972) NEGLIGIBLE

(1975) 2.33X10+8 G

(1984) 1.09X10+9 g

U.S. Production · 4 条

2023: 100,000,000 - <500,000,000 lb

1,2-Diaminoethane is produced in large quantities, 26,509,000 kg in 1993.

(1972) 2.70X10+10 G

(1975) 3.0X10+10 G

Consumption Patterns · 5 条

CHEMICAL PROFILE: Ethylenediamine. Exports (mainly for carbamate fungicides), 45%; chelating agents (mainly EDA tetraacetic acid tetrasodium salt), 25%; oil and gas additives, 5%; polyamides, 5%; aminoethylethanol-amine-based surfactants, 5%; ethylene (bis)stearamide, 5%; others, including urethane additives, 10%.

CHEMICAL PROFILE: Ethylenediamine. Demand: 1987: 75 million lb; 1988: 77 million lb; 1992 /projected/: 85 million lb. (Includes exports, but not imports, totalling 4 to 5 million lb in 1987, or potential demand for the new Air Products facility).

Chemical Profile: Ethylenediamine. Exports (mainly for carbamate fungicides and tetraacetylethylenediamine (TAED)), 45%; chelating agents (mainly ethylenediaminetetraacetic acid (EDTA) and tetrasodium salt), 25%; lube oil and gas additives, 5%; nonreactive polyamide resins, 5%; aminoethylethanolamine-based surfactants, 5%; ethylene(bis)stearamide, 5%; others, including urethane additives, 10%.

Chemical Profile: Ethylenediamine. Demand: 1990: 80 million pounds; 1991: 82 million pounds; 1995: 90 million pounds. (Includes exports, which in 1990 are estimated at about 35 million pounds).

Lube oil additives, 35%; wet strength resins, 12%; chelating agents, 11%; epoxy curing agents, 9%; surfactants, 8%; polyamide resins, 6%; oil field chemicals, 5%; miscellaneous, including ethylene bis(stearamide), 14% /Ethyleneamines including EDA/

应用领域 · 6 条

用途用于医药、农药、染料、塑料、橡胶等工业

用途乙二胺又名1,2-二氨基乙烷,是杀菌剂代森铵、代森锌、代森锰锌的中间体,也是杀虫剂吡虫啉的原料。

用途乙二胺是重要的化工原料,广泛用以制造有机化合物、高分子化合物、药物等,用于生产农药杀菌剂(代森锌、代森铵)、杀虫剂、除草剂、染料、染料固色剂、合成乳化剂、破乳剂、纤维表面活性剂、水质稳定剂、除垢剂、电镀光亮剂、纸的湿润强化剂、粘接剂、金属螯合剂EDTA、环氧树脂固化剂、橡胶硫化促进剂、酸性气体的净化剂、照相显影添加剂、超高压润滑油的稳定剂、焊接助熔剂、氨基树脂、乙二胺脲醛树脂等等。还用于有机溶剂和化学分析试剂,以及用于铍、铈、镧、镁、镍、钍、铀等金属的鉴定,锑、鉍、镉、钴、铜、汞、镍、银和铀的测定等。

用途用于治疗牛皮癣,对恶性淋巴瘤、头颈部肿瘤、软组织肉瘤也有一定的缓解作用

用途用作分析试剂、有机溶剂、抗冻剂和乳化剂

用途用作分析试剂、环氧树脂固化剂,也用于有机合成及制药工业

制备方法 · 2 条

生产方法1.二氯乙烷氨化法将1,2-二氯乙烷和液氨送入反应器中,在120-180℃温度和1.98-2.47MPa压力下,进行热氨解反应,将反应液蒸发一部分水分和过量的氨、然后送入中和器,用30%液碱中和,再经浓缩、脱盐、粗馏得粗乙二胺、粗三胺和多胺混合物,最后再将粗乙二胺在常压下精馏得乙二胺成品,其含量为70%,再加压精馏可得90%的成品。反应过程还副产二乙撑三胺,继续反应还生成三乙撑四胺,四乙撑五胺等多乙撑多胺。2.乙醇胺氨化法将乙醇胺、钴催化剂和水加入反应器,然后往其中通入氨和氢,在20MPa和170-230℃下进行反应,5-10h后,可制得乙二胺,其转化率达69%。反应过程的副反应还生成二乙撑三胺、哌嗪、氨乙基哌嗪、羟乙基哌嗪等。3.环氧乙烷氨化法。此外,从生产医药产品六水哌嗪的母液中,也可分馏得到乙二胺。

生产方法其制备方法有二氯乙烷法和乙醇胺法。(1)二氯乙烷法由二氯乙烷与氨直接合成,在钼钛不锈钢反应管道内进行,反应温度控制在160~190℃,压力为2.452 MPa,反应时间1.5min,反应后的合成液经蒸发一部分水分和过量氨进人中和器,用30%碱液中和,然后经浓缩、脱盐、粗馏得粗乙二胺、粗三胺、粗多胺等混合物,最后再将粗乙二胺在常压精馏得乙二胺成品,其含量70%,在加压下蒸馏可得90%纯度的产品。反应方程式如图:$SClCH2CH2Cl+2NH4OH→HCl·H2NCH2CH2NH2·HCl+2H2O[2NaOH]→NH2CH2CH2NH2+2Nacl(2)乙醇胺法将乙醇胺、氨和循环物料蒸发成气相混合物通入固定床反应器,反应在氢气流中进行,反应温度为300℃,压力为25 MPa,反应生成物部分冷凝后分出气相的氨和氢气,经压缩返回反应器,液相反应物经脱氨后脱水塔后进入精馏塔,从塔顶蒸出乙二胺和哌嗪,进一步分解得乙二胺成品。NH2CH2CH2OH+NH3→NH2CH2CH2NH2+H2O

试剂价格

A12132 · 500ml
乙二胺, 99%Ethylenediamine, 99% — 352元
42726 · 800ml
乙二胺Ethylenediamine, 99+%, AcroSeal™, Thermo Scientific Chemicals — 5030元

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