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Diisopropanolamine

Diisopropanolamine structure

Diisopropanolamine 

structure
  • CAS No:

    110-97-4

  • Formula:

    C6H15NO2

  • Chemical Name:

    Diisopropanolamine

  • Synonyms:

    2-Propanol,1,1′-iminobis-;2-Propanol,1,1′-iminodi-;1,1′-Iminobis[2-propanol];Diisopropanolamine;1,1′-Iminodi-2-propanol;Bis(2-hydroxypropyl)amine;Bis(2-propanol)amine;DIPA;N,N-Bis(2-hydroxypropyl)amine;DIPA (alcohol);Di-2-propanolamine;NSC 4963;N,N-Diisopropanolamine;1-[(2-Hydroxypropyl)amino]propan-2-ol;1-(2-Hydroxypropylamino)propan-2-ol;1335-54-2;1141787-00-9

  • Categories:

    Cosmetic Ingredient  >  Buffering

Description

WHITE HYGROSCOPIC CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR. TURNS YELLOW ON EXPOSURE TO LIGHT AND AIR.


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)|Liquid|WHITE HYGROSCOPIC CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR. TURNS YELLOW ON EXPOSURE TO LIGHT AND AIR.


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)|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 derives from a 1-aminopropan-2-ol.

Diisopropanolamine Basic Attributes

133.19

133.19

605363

203-820-9

0W44HYL8T5

0493

4963

DTXSID8020179

White waxy solid

2922199090

Characteristics

52.5

-0.82

Colorless to light yellow Low Melting Solid

0.989 g/cm3 @ Temp: 20 °C

44.5-45.5 °C

249-250 °C @ Press: 745 Torr

260 °F

1.4615-1.4635

H2O: 870 G/L (20 ºC)

Store below +30°C.

Vapour pressure, Pa at 42°C: 2.67

Relative vapour density (air = 1): 4.6

Oral-Rat LD50: 4765 mg/kg; Abdominal cavity-mouse LD50: 96 mg/kg

Flammable; burning emits toxic nitrogen oxides and ammonia fumes

1.6-8.0%(V)

pH of 5% aqueous solution = 11.5

Henry's Law constant = 2.5X10-11 atm-cu m/mol at 25 °C (est)

pKa = 9.1

CAN REACT WITH OZIDIZING MATERIALS|Hydroxyl radical reaction rate constant = 1X10-10 cu cm/molec-sec at 25 °C (est)

Water soluble.

Alcohols and Polyols

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)

580 °F (USCG, 1999)|374 °C

Dust explosion possible if in powder or granular form, mixed with air.

375 kJ/kg

Safety Information

III

8

3259

1

36

26

UB6600000

Xi

The warehouse is ventilated, low temperature and dry; store it separately from acids.

Hydrolysate ammonia is corrosive to the skin

P264, P280, P305+P351+P338, P33, P313

H319

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.

Can react with oxidizing materials.|/Diisopropanolamine (DIPA)/... can react rapidly with acid to form the corresponding amine salt. DIPA... can react with fatty acid esters to form diisopropanolamides... .

European 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

This compound is combustible. (NTP, 1992)|Combustible. Finely dispersed particles form explosive mixtures in air.

|Warning|H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Danger|H318 (52.81%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, P310, and P337+P313|Aggregated GHS information provided by 1586 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P337+P313, P363, P405, and P501

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. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

Full face mask or amine vapor mask only if required; clean, body-covering clothing, rubber gloves, apron, boots and face shield. (USCG, 1999)|/Wear/ protective gloves, safety goggles, or eye protection in combination with breathing protection if powder.

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

Explosive limits , vol% in air: 1.1-5.4

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.

Sweep 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).

...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.

Irritates eyes, skin, nose

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.

Separated from strong oxidants and strong acids. Dry. Keep in the dark. Well closed.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is corrosive to the eyes, skin and respiratory tract. Inhalation of the aerosol may cause lung oedema. The effects may be delayed. Medical observation is indicated.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves.

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

Toxicity

moderately toxic

LD50 Mouse ip 96 mg/kg|LD50 Rat oral 4765 mg/kg|LD50 Mouse oral 2120 mg/kg|LD50 Rabbit oral 4700 mg/kg|For more Non-Human Toxicity Values (Complete) data for DIISOPROPANOLAMINE (6 total), please visit the HSDB record page.

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).

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).

The rate constant for the vapor-phase reaction of diisopropanolamine with photochemically-produced hydroxyl radicals has been estimated as 1X10-10 cu cm/molecule-sec at 25 °C(SRC), using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diisopropanolamine will exist predominantly in the protonated form in the environment based on a pKa value of 9.1(2). Diisopropanolamine is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(SRC).

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).

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).

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).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 35,237 workers (3,440 of these are female) are potentially exposed to diisopropanolamine in the US(1). Occupational exposure to diisopropanolamine may occur through inhalation and dermal contact with this compound at workplaces where diisopropanolamine is produced or used(SRC). The general population may be exposed to diisopropanolamine dermally through the use of cosmetic products containing this compound(SRC).

Drug Information

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.

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.

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

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

Exposure treatment: Inhalation: if ill effects occur, remove person to fresh air, and get medical help. Ingestion: if swallowed and patient is conscious and not convulsing, promptly give milk or water, then induce vomiting; get medical help. No specific antidote known. Eye and skin: immediately flush with plenty of water for at least 15 min. For eyes, get medical help promptly. Remove, and wash contaminated clothing before reuse.

/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.

bis(2-hydroxypropyl)amine

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

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


Pain. Redness. Blisters. Skin burns.


Pain. Redness. Severe deep burns.

Diisopropanolamine Use and Manufacturing

Methods of Manufacturing

Propylene oxide reacts with ammonia to produce monoisopropanolamine, and continues to react with propylene oxide to produce di- and triisopropanolamine. After mixing propylene oxide and ammonia, it is preheated to the reaction temperature and enters the reactor for reaction. The reaction product is first stripped to remove ammonia and water, and the ammonia is recycled. Then, the crude isopropanolamine is sent to the vacuum rectification system to fractionate monoisopropanolamine, diisopropanolamine and triisopropanolamine into pure products. When there is a large excess of propylene oxide in the raw material ratio, the proportion of triisopropanolamine in the resulting product increases.

Uses

Emulsifying and neutralizing agent in cosmetics.Removal of H2S and CO2 from natural and industrial gases.Antimicrobial agent in cutting fluids.


Dyes


Automotive care products

Production

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.

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/

All other basic organic chemical manufacturing|2-Propanol, 1,1'-iminobis-: ACTIVE|2-Propanol, 1,1'-iminobis-, N-(hydrogenated tallow alkyl) derivs.: INACTIVE

Detection by gas chromatography with flame ionization.

Computed Properties

Molecular Weight:133.19
XLogP3:-0.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:133.110278721
Monoisotopic Mass:133.110278721
Topological Polar Surface Area:52.5
Heavy Atom Count:9
Complexity:60.1
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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