Grundinformationen
- Standard-SMILES
NCCNCCN- InChIKey
RPNUMPOLZDHAAY-UHFFFAOYSA-N- Summenformel
- C4H13N3
- Durchschnittliche Molmasse
- 103,17 g/mol
- Monoisotopische Masse
- 103,11094742
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Diethylenetriamine
- IUPAC
- N'-(2-aminoethyl)ethane-1,2-diamine
- Lokaler Name
- 3-Azapentan-1,5-diamin
- Englischer Name
- Diethylenetriamine
- Summenformel
- C4H13N3
- Molmasse
- 103.17
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -2,1
- Polarare Oberfläche (TPSA)
- 64,1 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 26,1
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Nitrogen Compounds -> Amines, Aliphatic
Corrosives
LogP
-1.3
-1.3
Odor
AMMONIACAL ODOR
... Strong, ammonia-like odor ...
Density
0.954 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9586 @ 20 °C/20 °C
Relative density (water = 1): 0.96
0.96
0.9586 @ 20°C
0.96
Color/Form
YELLOW LIQUID
Colorless liquid
Colorless to yellow liquid ... [Note: Hygroscopic (i.e., absorbs moisture from the air)].
Solubility
Very soluble (NTP, 1992)
SOL IN ALL PROP IN WATER & ALC; INSOL IN ETHER; SOL IN PETROLEUM ETHER
SOL IN HYDROCARBONS
miscible with water, methanol, acetone, ether, and benzene, but insoluble in heptane
water solubility = 1X10+6 mg/l
1000 mg/mL
Flash Point
215 °F (NTP, 1992)
101 °C
101.7 °C (Open cup)
97 °C c.c., 102 °C o.c.
208 °F
208 °F
Boiling Point
405 °F at 760 mmHg (NTP, 1992)
207 °C @ 760 MM HG
207.00 °C. @ 760.00 mm Hg
207 °C
405 °F
207 °C @760 [mm Hg]
Physikochemische Eigenschaften
- Schmelzpunkt
- -40 °C · -40 °C
- Siedepunkt
- 206 °C · 206 °C
- Dichte
- 0.955 g/mL · 0.955 g/mL at 25 °C(lit.)
- Dampfdichte
- 3.6 · 3.6 (vs air)
- Dampfdruck
- 0.08 mm · 0.08 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.484(lit.)
- Flammpunkt
- 90 °C · 90 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- Chloroform (Soluble), Methanol (Slightly)
- pka
- 1 · pK1:4.42(+3);pK2:9.21(+2);pK3:10.02(+1) (25°C)
- Aggregatzustand
- Liquid
- Farbe
- Clear
- Geruch (Odor)
- Strong ammoniacal; mildly ammoniacal.
- PH
- 12 · >12 (100g/l, H2O, 20℃)
- Explosionsgrenze
- 1 · 1-10%(V)
- Wasserlöslichkeit
- miscible
- Spezifische Wärmekapazität
- 2.46 J/ · Cp(liquid): 2.46 J/(g·K), at 25℃
- BRN
- 605314 · 605314
- Henry's Law Constant
- 9.9 · 9.9×108 mol/(m3Pa) at 25℃, HSDB (2015)
- Stabilität
- Stable, but absorbs carbon dioxide from the air. Incompatible with strong oxidizing agents, copper and its alloys.
- InChI
- 1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2
- InChIKey
- RPNUMPOLZDHAAY-UHFFFAOYSA-N
- SMILES
- NCCNCCN
- LogP
- -1.58 at · -1.58 at 20℃
- CAS Datenbank
- 111 · 111-40-0(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · 1,2-Ethanediamine, N-(2-aminoethyl)-(111-40-0)
- EPA chemische Informationen
- Diethylenetriamine (111-40-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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]
Gefahrenhinweise
Regulatory Information
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.)
Fire Hazards
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.
Health Hazards
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.
Hazards Summary
Corrosive to skin; [Quick CPC] Liquid causes first degree burns on short exposure; [CHRIS] DETA can cause severe corneal injuries and sensitization of the skin and respiratory tract. [ACGIH] Allergic contact dermatitis reported in workers using ultrasonic baths, synthetic lubricants, and carbonless copy paper. [Kanerva, p. 1782] Repeated or prolonged contact may cause skin sensitization or asthma. Inhalation may cause pulmonary edema. [ICSC] Prolonged inhalation can cause asthma. [CAMEO] Danger of skin sensitization; [MAK]
DOT ID and Guide
2079 154
2079 154
TSCA Requirements
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.
Reactivity Profile
DIETHYLENETRIAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Sicherheit und Schutzausrüstung
Fire Fighting
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
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
· 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:
(General first aid procedures)
Fire Fighting Procedures
Use water spray, dry chemical, alcohol foam or carbon dioxide. Discharge is effective for cooling of container, dilution, prevention of spread of the fire.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical.
Wear goggles, self-contained breathing apparatus, and rubber overclothing (including gloves). ... Water or foam may cause frothing.
Disposal Methods
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.
Incinerate in admixture with flammable solvent in furnace equipped with afterburner and scrubber. Recommendable method: Incineration. Peer-review: Mix with excess fuel due to low carbon content and high nitrogen content. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Spillage Disposal
Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Toxikologische Informationen
Environmental Fate
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).
Exposure Routes
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
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
Soil Adsorption/Mobility
The Koc for diethylenetriamine estimated from molecular structure is 88(1). Therefore, it would not be expected to adsorb significantly to soil or sediment. According to a suggested classification scheme(2), this estimated Koc suggests that diethylenetriamine would be highly mobile in soil(SRC).
TSCA Test Submissions
The mutagenicity of diethylenetriamine (DETA) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, DETA, diluted with water, was tested for mutagenicity at concentrations up to 10 ul/plate using the quantitative overlay method. DETA caused a reproducible increase in revertants without activation in bacterial testers strain TA1537 at all concentrations tested ranging from 0.001 - 10 ul/plate and in tester strain TA1538 without activation at 0.01, 1, 5, and 10 ul/plate. No dose related response was obtained. DETA did not cause a reproducible positive response in any of the other bacterial tester strains, either with or without activation, or in strains TA1537 and TA1538 with activation.
The mutagenicity of diethylenetriamine (DETA) was evaluated in Salmonella bacterial tester strains TA98, TA100, TA1535, TA1537 and TA1538, and the yeast Saccharomyces cerevisiae tester strain D4, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, DETA, diluted with DMSO, was tested for mutagenicity at concentrations up to 10 ul/plate using the agar incorporation method. DETA did not cause a positive response in any of the bacterial or yeast tester strains, either with or without metabolic activation.
The ability of diethylenetriamine (DETA) to induce mutations at the HGPRT gene locus in Chinese Hamster Ovary (CHO) cells in vitro was evaluated in the presence and absence of Aroclor-induced rat liver S9 metabolic activation. Based on preliminary toxicity determinations, DETA was tested for mutagenicity at 6 concentrations over the range of 0.0125 - 0.400% (v/v), with cell survival ranging from 80 - 101% without activation and 110 - 135% with activation. There were no significant differences between treated and control cultures with respect to mutation frequencies at any of the concentrations tested, either with or without activation.
The effect of diethylenetriamine (high purity grade) was examined in the rat hepatocyte primary culture/DNA repair assay following administration at concentrations ranging from 1x10E-4 to 0.1% (v/v). The test article induced statistically significant (Duncans MR analysis, p <0.05), but non-dose related increases in the amount of radioactive label bound to isolated nuclear DNA at the 1x10E-4 and 3x10E-3 % levels, and an increase in the amount of radioactive label bound to nuclei at the 1x10E-4 level. In a preliminary cytotoxicity test, all cells died when exposed to 0.4% diethylenetriamine.
For more TSCA Test Submissions (Complete) data for DIETHYLENETRIAMINE (11 total), please visit the HSDB record page.
Human Toxicity Excerpts
Diethylenetriamine is characterized by its capacity to cause severe corneal injury and pulmonary and cutaneous sensitization in humans. Solutions of from 15% to 100% caused lasting corneal damage; 5% only minor injury; and unless properly controlled, the vapor and liquid cause sensitization of the respiratory tract and skin with relatively high frequency. Pulmonary and cutaneous sensitization occur with relatively high frequency unless adequate measures are taken to control all contacts. ... Little exposure is necessary in some cases to induce a high degree of sensitivity.
IT IS A POTENT PRIMARY SKIN IRRITANT, CAUSING EDEMA & SOMETIMES NECROSIS. THE SKIN IRRITATION IS FREQUENTLY COMPLICATED BY A HIGH INCIDENCE OF ALLERGIC SKIN SENSITIZATION. THE MAJORITY OF WORKERS CHRONICALLY EXPOSED TO IT BECOME SENSITIZED.
Symptoms: Conjunctivitis, keratitis (inflammation of the cornea), dermatitis, irritation of respiratory tract; asthmatic breathing, nausea, vomiting.
In addition to being an irritant, the polyamines typified by ... diethylenetriamine ... have been reported to cause dermal and pulmonary sensitization.
For more Human Toxicity Excerpts (Complete) data for DIETHYLENETRIAMINE (6 total), please visit the HSDB record page.
Artificial Pollution Sources
Diethylenetriamine may be released in emissions and wastewater during its manufacture and use as a chemical intermediate in the manufacture of wet strength resins, surfactant-softeners, corrosion inhibitors, gas and lube additives, epoxy curing agents, chelating agents, polyamide resins, and asphalt emulsifiers(1). Spills during transport, storage and use would also result in releases(SRC).
Environmental Biodegradation
Chemicals containing two terminal amino groups on a noncyclic compound are associated with persistance in 5-day BOD tests(4). Diamines, such as diethylenetriamine, in which the 2 nitrogen groups were not separated by at least 3 carbon atoms were recalcitrant and did not support bacterial growth as a sole source of carbon, nitrogen, and energy(6). No degradation of diethylenetriamine was observed in a 5-day BOD test using an acclimated sewage inoculum(4). Diethylenetriamine is listed as resistant to biodegradation according to the biodegradability test of the Japanese Ministry of International Trade and Industry(1). This test utilizes a mixed inoculum containing sewage, soil and surface water. The BOD was 0% of theoretical in 20 days when incubated with sewage(2). However, the BOD increased to 70% theoretical when an inoculum composed of treated petrochemical effluent, sewage and soil was used that had previously been acclimated for 45-60 days(2). In other BOD tests, 55% of the diethylenetriamine in wastewater biodegraded in 6 weeks(3) and 0% degraded in 2 weeks(5).
Regulatorische Informationen
TSCA Requirements
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.
Sicherheitsdaten
- OEB
- B
- OEL
- TWA: 1 ppm (4 mg/m3) [skin]
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 2079
- hs_code
- 29212900
- RTECS-Nr.
- IE1225000
- risk_code
- 21/22-34-43-37-26
- Toxizität
- LD50 orally in Rabbit: 1540 mg/kg
- hazard_code
- C,T+
- safety_code
- 26-36/37/39-45-28
- hazard_class
- 8
- packing_group
- II
- Speicherklasse
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Giftige Stoffe Daten
- 111-40-0(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1Skin Corr. 1BSkin Sens. 1BSTOT SE 3
- Selbstentzündungstemperatur
- 676 °F
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
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
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.
Verwendung und Herstellung
Uses
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
2023: 50,000,000 - <100,000,000 lb
(1972) 1.47X10+10 G
(1974) 1.47X10+10 G (SALES)
(1992) 38,941,000 kgs
General Manufacturing Information
Paper Manufacturing
1,2-Ethanediamine, N1-(2-aminoethyl)-: ACTIVE
Anwendungen
BeschreibungDiethylenetriamine 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.
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