Grundinformationen
- Standard-SMILES
CC(O)CNCC(C)O- InChIKey
LVTYICIALWPMFW-UHFFFAOYSA-N- Summenformel
- C6H15NO2
- Durchschnittliche Molmasse
- 133,19 g/mol
- Monoisotopische Masse
- 133,11027872
Überblick
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)
Namen und Bezeichner
- Bevorzugter Name
- Diisopropanolamine
- IUPAC
- 1-(2-hydroxypropylamino)propan-2-ol
- Englischer Name
- Diisopropanolamine
- Summenformel
- C6H15NO2
- Molmasse
- 133.1888
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
110-97-4- PubChem CID
- 8086
- DTXSID
DTXSID8020179- ChEMBL
CHEMBL2106303- ChEBI
CHEBI:143266- UNII
- 0W44HYL8T5
- EC Number
- 203-820-9
- Nikkaji
- J5.102K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,8
- Polarare Oberfläche (TPSA)
- 52,5 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 60,1
Experimentelle und physikochemische Eigenschaften
Polymers
Plastics -> N.a.
Plastics -> Other stabilisers
LogP
log Kow= -0.82
-0.82
Density
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
Solubility
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
Solubility in water, g/100ml at 20 °C: 87
Flash Point
259 °F (NTP, 1992)
255 °F (127 °C) (open cup)
127 °C o.c.
Boiling Point
480.2 °F at 760 mmHg (NTP, 1992)
249 °C
248 °C
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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]
Gefahrenhinweise
Regulatory Information
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
Fire Hazards
This compound is combustible. (NTP, 1992)
Combustible. Finely dispersed particles form explosive mixtures in air.
Fire Potential
Combustible when exposed to heat or flame...
Propanolamines burn when exposed to heat, flame, sparks, and powerful oxidizers. /Propanolamines/
Hazards Summary
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]
Reactivity Profile
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)
Sicherheit und Schutzausrüstung
Fire Fighting
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
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
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.
Fire Fighting Procedures
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.
Nonfire Spill Response
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
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
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
...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.
Toxikologische Informationen
Ecotoxicity Values
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
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).
Toxicity Summary
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
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
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
/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
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
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
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
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).
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H319
Chemie und Industrie
Pharmakologische Informationen
Absorption, Distribution and Excretion
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.
Verwendung und Herstellung
Uses
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
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
(1972) No Data
(1975) No Data
(1986) No Data
U.S. Imports
(1972) No Data
(1975) No Data
(1986) No Data
U.S. Production
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.
Methods of Manufacturing
Preperation: J. N. Wickert, US 1988225 (1935 to Carbide and Carbon Chem.)
Reaction of propylene oxide with ammonia.
Formulations/Preparations
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/
Use Classification
Plastics -> Other stabilisers
Plastics -> Polymer Type -> N.a.
General Manufacturing Information
Paper Manufacturing
2-Propanol, 1,1'-iminobis-: ACTIVE
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