Diethanolamine

HCID 8113CAS 111-42-2

Basic information

Standard SMILES
OCCNCCO
InChIKey
ZBCBWPMODOFKDW-UHFFFAOYSA-N
Molecular formula
C4H11NO2
Average molar mass
105.14 g/mol
Monoisotopic mass
105.07897859

Overview

Diethanolamine can cause cancer according to California Labor Code.

Names & identifiers

Preferred name
Diethanolamine
IUPAC
2-(2-hydroxyethylamino)ethanol
English name
N,N-Diethanolamine
Molecular formula
C4H11NO2
Molecular weight
105.14

Names & synonyms

DIETHANOLAMINE111-42-22,2'-IminodiethanolDiolamineIminodiethanolBis(2-hydroxyethyl)amine2-(2-Hydroxyethylamino)ethanolDiethanolaminDiethylolamine2,2'-DihydroxydiethylamineN,N-DiethanolamineEthanol, 2,2'-iminobis-
Show more names
Di(2-hydroxyethyl)amine2,2'-IminobisethanolN,N'-IminodiethanolNiax DEOA-LFDiaethanolaminBis(hydroxyethyl)amineDabco DEOA-LF2-[(2-hydroxyethyl)amino]ethan-1-ol

Database identifiers

CAS
111-42-2
PubChem CID
8113
DTXSID
DTXSID3021932
ChEMBL
CHEMBL119604
ChEBI
CHEBI:28123
UNII
AZE05TDV2V
EC Number
203-868-0
Nikkaji
J808G

Properties

Computed structural properties

XLogP
-1.4
Topological polar surface area
52.5 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
7

Experimental & physicochemical properties

Chemical Classes · 3 items

Hazardous Air Pollutants (HAPs)

Nitrogen Compounds -> Ethanolamines

Corrosives

PFASPFAS -> Other/unspecified
Cosmetics · 2 items

Cosmetics ingredient -> Buffering/pH Adjusting; Fragrance

Cosmetic ingredients (Diethanolamine) -> CIR (Cosmetic Ingredient Review)

pHStrong base. pH of 0.1 N aqueous solution: 11.0
SpringerMaterials PropertiesBoiling point
LogP · 4 items

log Kow= - 1.43

-1.43

-1.43

-1.43

Physicochemical properties

Melting point
28 °C · 28 °C
Boiling point
217 °C · 217 °C
Density
1.097 g/mL · 1.097 g/mL at 25 °C
vapor density
3.63 · 3.63 (vs air)
vapor pressure
0.01 mm · < 0.01 mm Hg @ 20°C
Flash point
138 °C · 138 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P260, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.5% (17 of 3242) of reports.

Danger

H302 (98.8%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 6 items

Chemical: Ethanol, 2,2'-iminobis-

Hazard Traits - Carcinogenicity; Cardiovascular Toxicity; Hematotoxicity; Respiratory Toxicity

Ethanol, 2,2'-iminobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2,2'-iminobis- 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: 16-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15770

Diethanolamine: 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 - Ethanol, 2,2'-iminobis-: Human health tier III assessment
DOT LabelClass 9
Fire Hazards · 2 items

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

Combustible.

Fire PotentialCombustile, when exposed to heat or flame; can react with oxidizing materials.
Health HazardsIrritation of eyes and skin. Breathing vapors may cause coughing, a smothering sensation, nausea, headache. (USCG, 1999)

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . Rest.

First Aid · 2 items

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 procedures)

Safe StorageSeparated from strong oxidants and acids. Dry.
Exposure Control and Personal Protection1.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting Procedures · 3 items

Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, dry chemical, alcohol foam or carbon dioxide fire extinguishing agent. Use water to keep fire-exposed containers cool, to disperse the vapors, to flush spills away from exposure, to dillute spills to nonflammable mixtures and to prevent the spread of fires.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

Toxicology

Target OrgansEyes, skin, respiratory system
Ecotoxicity Values · 5 items

LC50; Species: Goldfish; Concentration: 800 mg/L for 24 hr at pH 9.6 /Conditions of bioassay not specified/

LC50; Species: Goldfish; Concentration: >5000 mg/L for 24 hr at pH 7 /Conditions of bioassay not specified/

LC50; Species: Xenopus laevis (African Clawed Frog) age 3-4 wk; Conditions: freshwater, static, 20 °C; Concentration: 1174000 ug/L for 48 hr /formulation/

EC50; Species: Ceriodaphnia dubia (Water Flea) age <24 hr neonate; Conditions: freshwater, static, 23 °C; Concentration: 72920 ug/L for 48 hr (95% confidence interval: 61800-86040 ug/L); Effect: intoxication, immobilization /formulation/

For more Ecotoxicity Values (Complete) data for DIETHANOLAMINE (14 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a reported Koc value of 3.97(2), indicates that diethanolamine is expected to have very high mobility in soil(SRC). The pKa of diethanolamine is 8.96(3), indicating that this compound will exist partially in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of diethanolamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-11 atm-cu m/mole(SRC), based upon its vapor pressure, 2.8X10-4 mm Hg(5), and water solubility, 1X10+6 mg/L(5) and its pKa(3). Diethanolamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Diethanolamine is expected to biodegrade in soil; however, studies show the rate of degradation can vary widely depending on the conditions and acclimation of the soil(6).

AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 3.97(2), indicates that diethanolamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral form from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.9X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 2.8X10-4 mm Hg(4), and water solubility, 1X10+6 mg/L(4). A pKa of 8.96(5) indicates diethanolamine will exist partially in the cation form at pH values of 5 to 9 and, therefore, volatilization from water surfaces of the cation form is not expected to be an important fate process(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of -1.43(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethanolamine is expected to biodegrade in water; however, studies show the rate of degradation can vary widely depending on the conditions and acclimation state(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethanolamine, which has a vapor pressure of 2.8X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethanolamine 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 4 hours(SRC), calculated from its rate constant of 9.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diethanolamine does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 items

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

inhalation, ingestion, skin and/or eye contact

Toxicity Summary · 2 items

The CIR Expert Panel concluded that diethanolamine and the 16 related salts listed below are safe in the present practices of use and concentration when formulated to be non-irritating. The Expert Panel cautions that ingredients should not be used in cosmetic products in which N-nitroso compounds can be formed.

Safe for use in cosmetics, with qualifications

Regulatory information

FDA RequirementsDiethanolamine is an indirect food additive for use only as a component of adhesives.
TSCA Requirements · 1 item

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. Diethanolamine is included on this list. Effective date: 4/13/89; Sunset date: 6/30/98.

FIFRA Requirements · 1 item

Residues of diethanolamine are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Stabilizer, inhibitor for formulations used before crop emerges from soil.

Atmospheric Standards · 1 item

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Diethanolamine is included on this list.

CERCLA Reportable Quantities · 1 item

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 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

Safety data

Signal word
Danger
Symbol(GHS)
GHS05,GHS07,GHS08
Hazard statements
H302-H315-H318-H361fd-H373
Autoignition Temperature
365 °C
Precautionary statements
P202-P280-P301+P312-P302+P352-P305+P351+P338-P308+P313

Chemistry & industry

Pharmacology

Mechanism of Action · 4 items

Diethanolamine (DEA) is a widely used ingredient in many consumer products and in a number of industrial applications. It has been previously reported that dermal administration of DEA to mice diminished hepatic stores of choline and altered brain development in the fetus. The aim of this study was to use mouse neural precursor cells in vitro to assess the mechanism underlying the effects of DEA. Cells exposed to DEA treatment (3mM) proliferated less (by 5-bromo-2-deoxyuridine incorporation) at 48 hr (24% of control [CT]), and had increased apoptosis at 72 hr (308% of CT). Uptake of choline into cells was reduced by DEA treatment (to 52% of CT), resulting in diminished intracellular concentrations of choline and phosphocholine (55 and 12% of CT, respectively). When choline concentration in the growth medium was increased threefold (to 210 uM), the effects of DEA exposure on cell proliferation and apoptosis were prevented, however, intracellular phosphocholine concentrations remained low. In choline kinase assays, we observed that DEA can be phosphorylated to phospho-DEA at the expense of choline. Thus, the effects of DEA are likely mediated by inhibition of choline transport into neural precursor cells and by altered metabolism of choline. /This/ study/ suggests that prenatal exposure to DEA may have a detrimental effect on brain development.

Diethanolamine increased the incidence and multiplicity of liver tumors in the mouse following chronic exposure. Diethanolamine is known to inhibit cellular choline uptake. Since choline deficiency produces tumors in rodents, diethanolamine, through choline depletion, may result in tumor development in rodents. The potential for diethanolamine to function through this mode of action in humans is not known. The present studies examined the effect of diethanolamine (0-500 mug/mL) and choline depletion on DNA synthesis and changes in expression of genes involved in cell growth pathways in primary cultures of mouse, rat, and human hepatocytes. In mouse and rat hepatocytes DNA synthesis was increased following treatment with 10 mug/mL diethanolamine and higher (3- to 4-fold over control). In contrast, diethanolamine failed to increase DNA synthesis in human hepatocytes. Incubation of hepatocytes in medium containing reduced choline (1/10 to 1/100 of normal medium; 0.898 to 0.0898 mg/L vs. 8.98 mg/L) increased DNA synthesis (1.6- and 1.8-fold of control in mouse and rat hepatocytes, respectively); however, choline depletion did not induce DNA synthesis in human hepatocytes. Mouse and rat hepatocytes incubated in medium supplemented with 2- to 50-fold excess choline reduced diethanolamine-induced DNA synthesis to control levels or below. Gene expression analysis of mouse and rat hepatocytes following diethanolamine treatment showed increases in genes associated with cell growth and decreases in expression of genes involved in apoptotic pathways. These results support the hypothesis that choline depletion is central to the mode of action for the induction of rodent hepatic neoplasia by diethanolamine. Furthermore, since diethanolamine treatment or choline depletion failed to induce DNA synthesis in human hepatocytes, these results suggest that humans may not be at risk from the carcinogenic effects of diethanolamine.

Diethanolamine which interferes with phospholipid metab produced a loss of mitochondrial integrity after subacute admin to Sprague-Dawley rats.

Diethanolamine inhibited in vitro synthesis of phosphatidyl choline and phosphatidyl ethanolamine in rat liver tissue.

Metabolism/Metabolites · 4 items

Treatment of Wistar or Sherman rats with diethanolamine caused increases in the formation of hepatic phospholipids. In addition, dietary administration led to incorporation of ethanolamine into hepatic phospholipids, and repeated oral administration of diethanolamine in drinking water (one to three wk) at a dose of 320 mg/kg/day was found to reduce the level of incorporation of ethanolamine and choline into hepatic and renal phospholipids in Sprague-Dawley rats.

Dermal absorption of diethanolamine is suggested to occur in rats since N-nitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water.

Diethanolamine is known to be incorporated into membrane phospholipids. It can be O-phosphorylated and N-methylated to metabolites that are incorporated into polar head groups as aberrant membrane phospholipids (phosphoglyceride and sphingomyelin analogues) via the ethanolamine metabolic pathway.

After a single intravenous or oral administration of diethanolamine, rats predomnantly excreted the parent compound in the urine; after repeated oral administration, the parent compound was still the major product excreted in the urine but N-methylated metabolites were also detected. The parent compound also accounted for the majority of radioactivity extracted from the liver and brain of rats administered (14)C-diethanolamine; two minor metabolites identified in tissues were N-methyldiethanolamine and N,N-dimethyldiethanolamine.

Absorption, Distribution and Excretion · 4 items

(14)C-Diethanolamine (7 mg/kg bw) was given orally to male Fischer 344 rats once or by daily repeat dosing for up to eight weeks. Single oral doses (0.7-200 mg/kg bw) were well absorbed but excreted very slowly. About 20-30% of oral and intravenous doses (7 mg/kg bw) was found in urine (mainly as unchanged diethanolamine), with less than 3% in feces and only 0.2% or less was exhaled (CO2) within 48 h. Most of the diethanolamine was retained in tissues at high concentrations. The tissue-to-blood ratios were 150-200 for the liver and kidney, 30-40 for the lung and spleen and 10-20 for the heart, brain and muscle. Tissue radioactivity was found mainly in aqueous extracts (up to 90%) and 5-10% was organic-extractable.

(14)C-Diethanolamine was applied to 19.5 sq cm of the dorsal skin (20 mg/sq cm, 1500 mg/kg bw) and covered for 48 hr (no washing) or for 6 hr before it was removed by washing. Absorbed (14)C-diethanolamine was determined in 48-hr urine and feces and from sampled tissues. Unwashed rats absorbed 1.4% and washed animals 0.64% of the dose, while the majority of (14)C-diethanolamine was recovered in the occlusive wrappings (80%) and in skin of the dose site (3.6%). The radioactivity was found in carcass, liver or kidneys but very little in urine (0.11%), feces or blood

Studies of the penetration of (14)C-diethanolamine from cosmetic formulations (shampoos hair dyes and body lotions) through human skin samples indicated that approximately 0.1% of the applied dose of shampoo and hair dye formulations was absorbed into the receptor fluid after 5-30 minutes; in a 72-hour repeated dose study with a body lotion formulation, nearly 30% of applied diethanolamine accumulated in the skin and approximately 1% was absorbed into the receptor fluid.

Dermal absorption of diethanolamine is suggested to occur in rats since N-nitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water.

Tissue LocationsThyroid Gland
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 6 items

CIR ingredient: Diethanolamine

Diethanolamine is used in cutting oils, soaps, shampoos, cleaners, polishers, cosmetics, and pharmaceuticals. It is also used as an intermediate in the rubber chemicals industry, as a humectant and softening agent, and as an emulsifier and dispersing agent in various agricultural chemicals.

Used as a detergent in paints, cutting oils, and cleaners; also used to make resins and plasticizers; [ACGIH] Used in metalworking fluids for cutting, stamping, and die-casting operations; [HSDB] Used in photography (color developing baths); [www.ci.tucson.az.us/arthazards/medium.html]

Metal Machining [Category: Heat or Machine]

To scrub gases as indicated under ethanolamine. Diethanolamine can be used with cracking gases and coal or oil gases which contain carbonyl sulfide that would react with monoethanolamine. As rubber chemicals intermediate. In the manufacture of surface active agents used in textile specialties, herbicides, petroleum demulsifiers. As emulsifier & dispersing agent in various agricultural chemicals, cosmetics, and pharmaceuticals. In the production of lubricants for the textile industry. As humectant and softening agent. In buffer formulations. In organic synthesis.

Liquid detergents for emulsions of paints, shampoos, cleaners, and polishes; chemical intermediate for resins, plasticizers, etc; solubilizing 2,4-D

U.S. Imports · 3 items

(1972) 6.36X10+7 G (MONO, DI, & TRI)

(1975) 2.03X10+9 G (MONO, DI, & TRI)

(1984) 1.40X10+9 G /MONO, DI, TRIETHANOLAMINE/

U.S. Production · 6 items

2023: 400,000,000 - <550,000,000 lb

(1972) 4.59X10+10 G

(1975) 3.89X10+10 G

(1983) 7.54X10+10 g

Ethanol, 2,2'-iminobis- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

For more U.S. Production (Complete) data for DIETHANOLAMINE (7 total), please visit the HSDB record page.

Consumption Patterns · 2 items

(For mono, di, & triethanolamine) 46% as an int for detergents (including textiles, toilet goods, metals & other specialty surfactant uses); 28% in gas conditioning & petroleum use; 6% as a chem int for morpholine; 20% for misc applications (including emulsion polishes & herbicides) (1975)

Detergents (including textile, toilet goods, metal and other specialty surfactants), 35 percent; gas conditioning and petroleum use, 30 percent; metal working, 15 percent; textiles, 10 percent; miscellaneous (including agricultural intermediates and cement grinding aids) and exports, 10 percent (1984) /ethanolamines/

Consumer UsesLubricating agent
Industry UsesIntermediate

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]

Related reactions

769 records

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