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Diisopropanolamine

HCID 8086
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Basic information

CAS
110-97-4
Standard SMILES
CC(O)CNCC(C)O
InChIKey
LVTYICIALWPMFW-UHFFFAOYSA-N
Molecular formula
C6H15NO2
Average molar mass
133.19 g/mol
Monoisotopic mass
133.11027872

Overview

Diisopropanolamine appears as colorless liquid or white to yellow crystalline solid with an odor of dead fish or ammonia. Liquid floats and mixes with water. Solid sinks and mixes in water. (USCG, 1999)

Names & identifiers

Preferred name
Diisopropanolamine
IUPAC
1-(2-hydroxypropylamino)propan-2-ol
English name
Diisopropanolamine
Molecular formula
C6H15NO2
Molecular weight
133.1888

Names & synonyms

DIISOPROPANOLAMINE110-97-4Bis(2-hydroxypropyl)amineBis(2-propanol)amine1,1'-Iminodi-2-propanol2-Propanol, 1,1'-iminobis-Di-2-propanolaminedi-isopropanolamineDIPA (alcohol)Dipropyl-2,2'-dihydroxy-amineN,N-Bis(2-hydroxypropyl)amine1,1'-Iminobis-2-propanol
Show more names
2-Propanol, 1,1'-iminodi-DTXSID8020179NSC-49630W44HYL8T5DTXCID201791,1'-Iminobis[2-propanol]CHEBI:1432661,1'-IMINOBIS(2-PROPANOL)

Database identifiers

CAS
110-97-4
PubChem CID
8086
DTXSID
DTXSID8020179
ChEMBL
CHEMBL2106303
ChEBI
CHEBI:143266
UNII
0W44HYL8T5
EC Number
203-820-9
Nikkaji
J5.102K

Properties

Computed structural properties

XLogP
-0.8
Topological polar surface area
52.5 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
9
Formal charge
0
Complexity
60.1

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aliphatic
Polymers · 2 items

Plastics -> N.a.

Plastics -> Other stabilisers

CosmeticsCosmetic ingredients (Diisopropanolamine) -> CIR (Cosmetic Ingredient Review)
pHpH of 5% aqueous solution = 11.5
LogP · 2 items

log Kow= -0.82

-0.82

Density · 3 items

0.99 at 107.6 °F (USCG, 1999) - Less dense than water; will float

0.989 at 20 °C/4 °C

Relative density (water = 1): 0.99

Viscosity1.98 cP at 45 °C
Color/FormWhite waxy solid
Solubility · 4 items

Soluble (>=10 mg/ml) (NTP, 1992)

Miscible in alcohol. Slightly soluble in toluene. Insoluble in hydrocarbons.

In water, 8.6X10+5 mg/L at 25 °C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1635) of reports.

Danger

H318 (51.2%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Hazard information

Regulatory Information · 4 items

Chemical: 2-Propanol, 1,1'-iminobis-

2-Propanol, 1,1'-iminobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanol, 1,1'-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: 24-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13889

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

Other Safety InformationIMAP assessments - 2-Propanol, 1,1'-iminobis-: Human health tier I assessment
Fire Hazards · 2 items

This compound is combustible. (NTP, 1992)

Combustible. Finely dispersed particles form explosive mixtures in air.

Fire Potential · 2 items

Combustible when exposed to heat or flame...

Propanolamines burn when exposed to heat, flame, sparks, and powerful oxidizers. /Propanolamines/

Health HazardsVapor concentrations too low to irritate unless exposure is prolonged. Liquid will burn eyes and skin. (USCG, 1999)

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 2 items

19.5 mg/kg (14)C-DIPA in acetone /was applied dermally/ to an area of skin on the shoulder of four female Fisher 344 rats. After evaporation of the solvent /site of application remained covered for 48 hr/. At 48 hr 25% of the substance had penetrated the skin (12% excreted in the urine, 1% excreted in the feces and expired air, 12.5% remaining in the tissue and 73% was recovered from the application site and surroundings.

When 4 female Fischer-344 rats were injected iv with 19 mg (14)C-labelled diisopropanolamine in aqueous solution, more than 70% of the radioactivity was eliminated from the blood during the first 6 hr. About 90% of the dose was recovered from the urine within 12 hours.

Uses & manufacturing

Uses · 6 items

CIR ingredient: Diisopropanolamine

Used as chemical intermediate, emulsifying agent (polishes, textile specialties, leather compounds, insecticides, cold wave permanent hair solutions, and water paints), antimicrobial agent in cutting fluids, and for removal of hydrogen sulfide and carbon dioxide from natural and industrial gases; Also used in adhesives, paper and paperboard, coatings, food packaging, and in prescription drugs; [HSDB]

Metal Machining [Category: Heat or Machine]

Chemical intermediate; agent for removal of hydrogen sulfide from natural gas

Emulsifying agents for polishes, textile specialties, leather compounds, insecticides, cutting oils, and water paints

Emulsifying and neutralizing agent in cosmetics. Removal of hydrogen sulfide and carbon dioxide from natural and industrial gases. Antimicrobial agent in cutting fluids.

Impurities · 1 item

Commercial samples of diisopropanolamine... were found to contain 20-1300 ppb of N-nitrosobis(2-hydroxypropyl)amine, an agent that is absorbed through the skin of hamsters and is a strong carcinogen in hamsters, rats, mice, rabbits, and guinea pigs.

U.S. Exports · 3 items

(1972) No Data

(1975) No Data

(1986) No Data

Related reactions

22 records
New reaction record
HRID 324306 reaction equation
HRID 324306As reactantuspto-grants-2001_04
HRID 379188 reaction equation
HRID 379188As reactantuspto-grants-2001_10
HRID 548491 reaction equation
HRID 548491As reactantuspto-grants-2011_05
HRID 586101 reaction equation
HRID 586101As productAs reactantuspto-grants-2005_08
HRID 728630 reaction equation
HRID 728630As reactantuspto-grants-1991_09
HRID 1016378 reaction equation
HRID 1016378As reactantuspto-grants-2002_11
HRID 1094993 reaction equation
HRID 1094993As reactantuspto-grants-2012_03
HRID 1095002 reaction equation
HRID 1095002As reactantuspto-grants-2012_03
Page 1 of 3

Compound notes

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Solubility in water, g/100ml at 20 °C: 87

Flash Point · 3 items

259 °F (NTP, 1992)

255 °F (127 °C) (open cup)

127 °C o.c.

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 3 items

480.2 °F at 760 mmHg (NTP, 1992)

249 °C

248 °C

Physicochemical properties

Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319
Precautionary statements
305 · P305+P351+P338
Hazards Summary · 1 item

A skin, eye, and nasal irritant; No allergic or photoallergic dermatitis observed in 25 volunteers; Weak skin sensitization reported from occupational exposure; Causes burns to rabbit eyes; Causes severe necrosis to rabbit skin; [HSDB] An eye irritant; [eChemPortal: ESIS] Hypothermia, diarrhea, uncoordinated movements, and seizures observed in lethal-dose animal studies; [IUCLID] No effects on fetal development when administered by gavage to pregnant rats; No data on effects to human pregnancy; [REPROTOX] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Can be absorbed through skin; Inhalation may cause pulmonary edema; [MSDSonline]

Reactive GroupAlcohols and Polyols
EC ClassificationSymbol: Xi; R: 36; S: (2)-26
Special ReportsEuropean Chemicals Bureau; IUCLID Dataset, diisopropanolamine (110-97-4) (2000 CD-ROM edition). Available from the database query page: http://ecb.jrc.it/esis/esis.php?PGM=ein as of September 19, 2005
Reactivity Profile · 1 item

DIISOPROPANOLAMINE is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. This compound may be sensitive to light and air. This compound will react with oxidizing materials. (NTP, 1992)

Chemical DangersDecomposes on heating and on burning. This produces toxic gases of nitrogen oxides. The solution in water is a medium strong base. Reacts with strong acids. Reacts violently with strong oxidants. This generates fire and explosion hazard.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing

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 items

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer 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. Refer for medical attention .

First Aid · 1 item

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.

Safe StorageSeparated from strong oxidants and strong acids. Dry. Keep in the dark. Well closed.
Fire Fighting Procedures · 2 items

To fight fire use alcohol foam, carbon dioxide, /or/ dry chemical.

Fire response: ...Wear goggles, self-contained breathing apparatus, and rubber overclothing (including gloves). ...Water may be ineffective on fire. Cool exposed containers with water.

Storage ConditionsSeparated from strong oxidants, strong acids. Dry. Keep in the dark. Well closed.
Cleanup MethodsSweep spilled substance into containers; if appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water (extra personal protection: A/P2 filter respirator for organic vapour and harmful dust).
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 item

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

Preventive Measures · 2 items

...Remove, and wash contaminated clothing before reuse.

/If inhaled/: Fresh air, rest. Half-upright position. Artificial respiration if indicated. Refer for medical attention. /If contacted with skin/: First rinse with plenty of water, then remove contaminated clothes and rinse again. Refer for medical attention. /If contacted with eyes/: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /If ingested/: Rinse mouth. Do NOT induce vomiting. Refer for medical attention.

Eye PreventionWear safety goggles or eye protection in combination with breathing protection if powder.

Toxicology

Ecotoxicity Values · 5 items

LC50 Carassium auratus (Goldfish) 1100 mg/L/24 hr; static

LC50 Xenopus laevis (Clawed frog) 410 mg/L/48 hr; static /formulated product/

LC50 Brachydanio rerio (Zebra Fish) >1000 -2200 mg/L/ 96 hr; static

LC50 Carassius auratus (Goldfish) 1100 mg/L/ 24 hr; static

For more Ecotoxicity Values (Complete) data for DIISOPROPANOLAMINE (8 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC) from a log Kow of -0.82(2) and a regression derived equation(3) indicates that diisopropanolamine is expected to have very high mobility in soil(SRC). A pKa value of 9.1(4) indicates that the protonated form of diisopropanolamine will be the dominant species in moist soil surfaces and cations adsorb more strongly than neutral species. Batch adsorption experiments indicated that the adsorption mechanism of diisopropanolamine involves ionic interaction at cation exchange sites of soils and clays, and tends to be greatest in materials that have a large cation exchange capacity such as montmorillonite(5). Volatilization of diisopropanolamine from moist soil surfaces will not be an important fate process since cations do not volatilize. Diisopropanolamine is not expected to volatilize from dry soil surfaces(SRC) based upon its extrapolated vapor pressure of 1.25X10-4 mm Hg at 25 °C(6). Screening studies using sewage sludge indicated that diisopropanolamine does not biodegrade readily(4,7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC) from a log Kow of -0.82(2) and a regression derived equation(3) indicates that diisopropanolamine is not expected to adsorb to suspended solids and sediment in water(SRC). A pKa value of 9.1(4) indicates that the protonated form of diisopropanolamine will be the predominant species in water and cations adsorb more strongly to suspended solids and sediment than neutral species. Volatilization from water surfaces will not occur since cations do not volatilize(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Screening studies using sewage sludge indicated that diisopropanolamine does not biodegrade readily(4,7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diisopropanolamine, which has a vapor pressure of 1.25X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diisopropanolamine 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), from its rate constant of 1X10-10 cu cm/molecule-sec at 25 °C, that was derived using a structure estimation method(3). Diisopropanolamine is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Toxicity Summary · 2 items

The Panel concludes that Diisopropanolamine, Triisopropanolamine, Isopropanolamine, and Mixed Isopropanolamines are safe as cosmetic ingredients in the present practices of use and concentration. The isopropanolamines should not be used in products containing N-nitrosating agents.

Safe for use in cosmetics, with qualifications

Signs and Symptoms · 4 items

Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.

Pain. Redness. Blisters. Skin burns.

Pain. Redness. Severe deep burns.

Burning sensation. Abdominal cramps. Shock or collapse.

Soil Adsorption/Mobility · 2 items

Batch equilibrium studies designed to evaluate the adsorption characteristics of diisopropanolamine in subsurface soils were conducted using aquifer material from three natural gas sites in Canada as well as montmorillonite and kaolinite clay materials(1). The adsorption isotherms were non-linear with Freundlich adsorption (Kf) coefficients ranging from 3.5 to 170, with the greatest values observed in the montmorillonite clay materials(1). Since diisopropanolamine has a pKa value of 9.1(1,2) it exists primarily as a cation in solution and a strong correlation between adsorption and the cation exchange capacity (CEC) of the material tested was observed(1). It was also noted that adsorption decreased with increasing solution electrolyte concentration as this resulted in competition for cation exchange sites in the clays and soils(1). Adsorption also decreased with increasing pH since at higher pH, a smaller percentage of diisopropanolamine exists in the protonated form.

The Koc of diisopropanolamine was estimated as 10(SRC), using a log Kow of -0.82(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diisopropanolamine is expected to have very high mobility in soil(SRC). The pKa of diisopropanolamine is 9.1(4) indicating that it exists predominantly in the protonated form in the environment, and protonated species often adsorb strongly to soils and clays through interaction with cation exchange sites(5). In general, diisopropanolamine is expected to possess less mobility in clay soils with a high cation exchange capacity (CEC) than indicated by the estimated Koc value(SRC).

Human Toxicity Excerpts · 5 items

/HUMAN EXPOSURE STUDIES/ Six out of 24 volunteers exhibited irritant responses when patched tested with neat /diisopropanolamine/, but no irritation occurred in a group of 61 volunteers tested with a 1% aqueous solution.

/HUMAN EXPOSURE STUDIES/ In a repeated patch-test, 25 male and female volunteers had 0.2 mL of a 2% aqueous solution of diisopropanolamine applied to the skin on their backs for 24 hr/day on 3 consecutive days/wk for 3 weeks. After treatment, the application sites were irradiated 3 times with a combination of UVA and UVB rays, at a dose which caused minimal erythema. Thereafter, they were treated only with UVA rays for 6 weeks (at a dose that did not cause erythema), and diisopropanolamine was then applied as patches to 2 sites on the back. One patch remained in place for 24 hours and the site was irradiated at patch removal; the other patch was kept on for 48 hours, and the site was examined for signs of contact dermatitis after removal. Diisopropanolamine did not cause allergic or photoallergic dermatitis.

/HUMAN EXPOSURE STUDIES/ ...In 203 volunteers, 0.2 mL of a facial sun-protection cream containing 1% diisopropanolamine was applied to the skin on their backs under occlusive cover for 24 hours. The application site was then examined for irritation. 24 hours later, a further patch was applied for 24 hours and this procedure was repeated for 10 working days. After a 13 day treatment-free interval, a patch was applied for 48 hours to test for sensitization. A second challenge patch was applied 8 days later for 48 hours. During the induction period, 12 volunteers showed irritation of varying degrees of severity. The sun-protection cream induced sensitization in one volunteer. /1% Diisopropanolamine/

/SIGNS AND SYMPTOMS/ Contact dermatitis due to 1,1'-iminodi-2-propanol was observed in occupationally exposed workers. Weak sensitization was observed.

For more Human Toxicity Excerpts (Complete) data for DIISOPROPANOLAMINE (6 total), please visit the HSDB record page.

Artificial Pollution Sources · 1 item

Diisopropanolamine's production and use as an emulsifying and neutralizing agent in cosmetics, antimicrobial agent in cutting fluids, and for the removal of hydrogen sulfide and carbon dioxide from natural gas(1), may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation · 1 item

Diisopropanolamine achieved 39% of its theoretical oxygen demand using a sewage sludge following a 20 day incubation period(1). No biodegradation was observed at day 5 or day 10, suggesting that an acclimation period was required(1). Diisopropanolamine was classified as recalcitrant based on the results of screening studies using acclimated sewage sludge enrichment cultures(2).

Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for diisopropanolamine(SRC), using a log Kow of -0.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

With a pKa of 9.1(1), diisopropanolamine will exist predominantly in its protonated form in the environment and the protonated form of diisopropanolamine will not volatilize from water or moist soil surfaces(2). Diisopropanolamine is not expected to volatilize from dry soil surfaces(SRC) based on its extrapolated vapor pressure of 1.25X10-4 mm Hg at 25 °C(3).

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H319
Precautionary statements
P305+P351+P338
U.S. Imports · 3 items

(1972) No Data

(1975) No Data

(1986) No Data

U.S. Production · 6 items

2023: 10,000,000 - <50,000,000 lb

This chemical is listed as a High Production Volume (HPV) (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).

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1986) No Data

For more U.S. Production (Complete) data for DIISOPROPANOLAMINE (9 total), please visit the HSDB record page.

Consumer UsesHydraulic fluids
Industry UsesHydraulic fluids
Methods of Manufacturing · 2 items

Preperation: J. N. Wickert, US 1988225 (1935 to Carbide and Carbon Chem.)

Reaction of propylene oxide with ammonia.

Formulations/Preparations · 2 items

Diisopropanolamine is 40-45 wt% of sulfinol solvent

Mixed isopropanolamines is a blend of 40-50% diisopropanolamine, 40-50% triisopropanolamine, and 10-15% isopropanolamine. /Mixed isopropanolamines/

Household ProductsInformation on 20 consumer products that contain Diisopropanolamine in the following categories is provided:
Use Classification · 2 items

Plastics -> Other stabilisers

Plastics -> Polymer Type -> N.a.

General Manufacturing Information · 2 items

Paper Manufacturing

2-Propanol, 1,1'-iminobis-: ACTIVE

Additional notes · 1 item

DefinitionChEBI: Diisopropanolamine is a secondary amino compound that is diethanolamine substituted by methyl groups at positions 1 and 1'. It is a versatile chemical used in a variety of personal care, cosmetic and industrial products. It has a role as a surfactant, an emulsifier and a buffer. It is a secondary amino compound, a secondary alcohol and an aminodiol. It is functionally related to a 1-aminopropan-2-ol.