HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,1',1''-Nitrilotripropan-2-ol
TPEA · TRIS(2-HYDROXYPROPYL)AMINE · Tri-2-propanolamine · AMIX TI · Tripropanolamine · NITRILOTRIPROPANOL · Tris(2-hydroxy-1-propyl)amine · Pharmaceutical Intermediate and Research Chemical 122-20-3
Identifikatoren & physikalische Daten
| CAS No. | 122-20-3 |
|---|---|
| Summenformel | C9H21NO3 |
| Durchschnittliche Molmasse | 191,27 g/mol |
| Monoisotopische Masse | 191,15214353 g/mol |
| SMILES | CC(O)CN(CC(C)O)CC(C)O |
| InChIKey | SLINHMUFWFWBMU-UHFFFAOYSA-N |
| PubChem CID | 24730 |
| ChEMBL | CHEMBL1877948 |
| ChEBI | CHEBI:170017 |
| EC No. | 204-528-4 |
| DTXSID | DTXSID5021415 |
| Lokaler Name | 1,1',1''-Nitrilotripropan-2-ol |
Chemische & physikalische Eigenschaften
| XLogP | -0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,9 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 108 |
| Stoffklassen | Nitrogen Compounds -> Amines, Aliphatic |
| Polymers | Plastics -> N.a. |
| Kosmetika | Cosmetic ingredients (Triisopropanolamine) -> CIR (Cosmetic Ingredient Review)Buffering |
| pH | pH = 10.8310.8 (100g/l, H2O, 20℃) |
| LogP (Verteilungskoeffizient) | log Kow = -0.015-1.2 |
| Dichte | 1.02 at 68 °F (USCG, 1999) - Denser than waterwill sink1.0 at 20 °C/4 °CDensity: 0.99 kg/L at 25 °C1.0 g/cm³ |
| Viscosity | 100 cps at 60 °C |
| Color/Form | Crystalline, white solidSolid at 25 °C |
| Löslichkeit | Soluble (NTP, 1992)Soluble in ethanolslightly soluble in chloroformSoluble in oxygenated and aromatic solventsSolubility at 25 °C, g/100g: acetone, 450methanol, >500ethanol, 365water, >500In water, >1000 g/L at 25 °CSolubility in water, g/100ml at 20 °C: 83 (good) |
| Flammpunkt | 320 °F (NTP, 1992)320 °F (160 °C) (Open cup)160 °C o.c. |
| Siedepunkt | 581 °F at 760 mmHg (NTP, 1992)306 °C305 °C190 °C/23 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides and hydrogen cyanide/. |
| Schmelzpunkt | 48-52 °C (lit.) |
| Dampfdruck | 1 hPa (100 °C) |
| Brechungsindex | 1.4200 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystalline Low Melting Solid |
| pKa (Säurekonstante) | 14.37±0.20(Predicted) |
| Farbe | White to slightly yellow |
| Explosionsgrenze | 0.8-5.8%(V) |
| BRN | 1071570 |
| Henry-Konstante | 1.0×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| Kosmetik-Inhaltsstoffe Funktionen | BUFFERING |
| InChI | 1S/C9H21NO3/c1-7(11)4-10(5-8(2)12)6-9(3)13/h7-9,11-13H,4-6H2,1-3H3 |
| InChIKey | SLINHMUFWFWBMU-UHFFFAOYSA-N |
| SMILES | CC(O)CN(CC(C)O)CC(C)O |
| LogP (Verteilungskoeffizient) | -0.015 at 23℃ |
| CAS Datenbank | 122-20-3(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propanol, 1,1',1''-nitrilotris-(122-20-3) |
| EPA chemische Informationen | Triisopropanolamine (122-20-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH319: 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 1735) of reports.H319 (98.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propanol, 1,1',1''-nitrilotris-2-Propanol, 1,1',1''-nitrilotris- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanol, 1,1',1''-nitrilotris- 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: 08-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14594Triisopropanolamine: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Propanol, 1,1',1''-nitrilotris-: Human health tier II assessment |
| Brandgefahren | Special Hazards of Combustion Products: Toxic fumes containing carbon monoxide, and/or carbon dioxide, and oxides of nitrogen.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | Combustible when exposed to heat or flame. |
| Gesundheitsgefahren | Irritation of eyes and skin. May cause slight corneal injury or burn. Repeated contact may cause skin burn. Heated vapor may cause moderate respiratory irritation. Low to moderately toxic by oral routes. (USCG, 1999) |
| Gefahrenübersicht | A skin, respiratory tract, and severe eye irritant[ICSC] A moderate skin and severe eye irritant in rabbitsNo evidence of mutagenicity[HSDB] An eye irritant[eChemPortal: ESIS] |
| FDA-Anforderungen | Triisopropanolamine is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Alcohols and Polyols |
| EG-Einstufung | Symbol: XiR: 36-52/53S: (2)-26-61 |
| UN-Einstufung | UN Hazard Class: 8UN Pack Group: II |
| FIFRA-Anforderungen | Residues of 2-propanol, 1,1',1''-nitrilotris- 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 or to raw agricultural commodities after harvest. Use: neutralizer. Limit: without limitation. |
| Reactivity Profile | TRIISOPROPANOLAMINE neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by combination with strong reducing agents, such as hydrides. |
| Brandbekämpfung | Fire Extinguishing Agents Not to Be Used: Ordinary foam.Use water spray, powder, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Half-upright position. Refer for medical attention.Rinse skin with plenty of water or shower.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. Give one or two glasses of water to drink. |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from strong oxidants, strong acids and food and feedstuffs. Dry. |
| Brandbekämpfungsverfahren | To fight fire, use alcohol foam, water, CO2, dry chemical. |
| Freisetung ohne Brand | Neutralizing Agents for Acids and Caustics: Flush heavily with water. (USCG, 1999) |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Remove all ignition sources. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. Prevent build-up of electrostatic charges (e.g., by grounding). |
| Inhalation Risk | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triisopropanolamine is expected to have very high mobility in soil(SRC). The pKa of triisopropanolamine is 8.06(3), indicating that this compound will partially exist 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 triisopropanolamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.8X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Triisopropanolamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.75X10-6 mm Hg at 25 °C(4). Triisopropanolamine was found to be not readily biodegradable using the Japanese MIT test where triisopropanolamine had only a 3.4% BODT after 4 weeks(5). However, the results of other ready, inherent and simulation tests have indicated that triisopropanolamine is readily susceptible to biodegradation with CO2 the dominant degradation product under aerobic conditions(3). One soil metabolism study found a triisopropanolamine half-life of approximately 2 days(3,4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triisopropanolamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.8X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), a BCF value of <0.57 in carp fish(5) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triisopropanolamine was found to be not readily biodegradable using the Japanese MIT test where triisopropanolamine had only a 3.4% BODT after 4 weeks(6). However, the results of other ready, inherent and simulation tests have indicated that triisopropanolamine is readily susceptible to biodegradation with CO2 the dominant degradation product under aerobic conditions(7). In a lake water-sediment batch study, triisopropanolamine had a half-life of 14.3 days with 62% mineralization to CO2(7). Triisopropanolamine is expected to be stable to aqueous hydrolysis in the environment(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triisopropanolamine, which has a vapor pressure of 9.75X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triisopropanolamine 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 about 3 hours(SRC), calculated from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase triisopropanolamine may be removed from the air by wet or dry deposition(SRC). Triisopropanolamine absorbs light at wavelengths >290 nm(2) and may be susceptible to direct photolysis by sunlight(SRC). |
| Toxizitätsübersicht | 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.Redness.Redness. Pain. Burns.Sore throat. Burning sensation. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of triisopropanolamine can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that triisopropanolamine is expected to have very high mobility in soil. The pKa of triisopropanolamine is 8.06(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). |
| Artificial Pollution Sources | Triisopropanolamine's production and use as a crosslinking agent for coatings, emulsifiers and surfactants, and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Triisopropanolamine, present at 100 mg/L, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L(1). In a biodegradation test, triisopropanolamine reached 0%, 46%, and >46% of its theoretical BOD in 5, 10, and 20 days, respectively, using surface water or sewage treatment inoculum(2). Triisopropanolamine, present at 30 mg/L, reached 3.4% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 100 mg/L in the Japanese MITI test(3). In inherent biodegradability BOD tests (system pre-acclimated to test compound), triisopropanolamine had 51%, 75% and >75% degradation after a 5-day, 10-day and 20-day incubation periods respectively(2). In a soil batch system using an initial triisopropanolamine concentration of 3.3 ppm, triisopropanolamine had a half-life of 2 days with 66-72% mineralization to CO2(2) and complete mineralization at 20 days(4). In a lake water-sediment batch system using an initial triisopropanolamine concentration of 2.3 ppm, triisopropanolamine had a half-life of 14.3 days with 62% mineralization to CO2(2). |
| Environmental Bioconcentration | During a 6 week period using carp fish (Cyprinus carpio), BCF values of <0.06 and <0.57 were measured for triisopropanolamine at respective concentrations of 2.5 and 0.25 mg/L(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for triisopropanolamine is estimated as 9.8X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that triisopropanolamine is expected to be essentially nonvolatile from water surfaces(2). Triisopropanolamine's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Triisopropanolamine acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.75X10-6 mm Hg at 25 °C(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ The initiation potential of N-nitrosobis(2-hydroxypropyl)amine (NDHPA) endogenously synthesized from bis(2-hydroxypropyl)amine (DHPA) or tris(2-hydroxypropyl)amine (THPA) in the presence of sodium nitrite (NaNO2) was investigated in the rat liver by quantitation of hepatocellular foci showing phenotypic expression of glutathione S-transferase placental form (GST-P). The investigation consisted of two experiments. In the first, male Wistar rats were divided into six groups as follows: group 1 was non-treatedgroups 2 & 3 received 0.15% & 0.3% NaNO2, respectivelygroup 4 received 1% DHPAgroups 5 & 6 received 1% DHPA together with 0.15% & 0.3% NaNO2, respectively. In experiment 2, the same protocol was used except that 2% THPA was substituted for 1% DHPA. The treatments were continuous until sacrifice at wk 94 in experiment 1 & wk 104 in experiment 2. As a result putative preneoplastic GST-P-positive foci observed in the liver & incr dose-dependently in rats from groups 5 & 6 which had received DHPA & NaNO2, but not in rats administered THPA & NaNO2. The results indicate that endogenously synthesized NDHPA from DHPA & NaNO2 is capable of initiating neoplastic development in the rat liver./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The objective of this study was to evaluate the maternal and developmental toxicity of Picloram K and /triisopropanolamine/ TIPA salts in rats. Pregnant Sprague-Dawley rats were gavaged with 0, 100, 500 or 1000 mg/kg/day of Picloram K or TIPA salt on days 6 through 15 of gestation. Maternal observations included changes in behavior and demeanor, feed consumption, body weight gain, gross pathologic alterations, liver and kidney weights and various reproductive parameters. On day 20 of gestation, fetuses were removed following cesarean section, weighed and examined for external, visceral and skeletal alterations. Maternal toxicity was noted in high dose females administered Picloram TIPA salt. Dams given 1000 mg/kg/day of Picloram TIPA salt had decreased feed consumption and body weight gain during the exposure period. No adverse maternal effects were observed with Picloram K salt and neither Picloram K or Picloram TIPAsalts were embryo/fetotoxic or teratogenic at any dose level. Thus, the developmental no-observed-effect-levels for Picloram K and TIPA salts were 1000 mg/kg/day/GENOTOXICITY/ Tris-isopropanolamine (TIP) was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. TIP was tested at doses 0, 100, 333, 1000, 3333, and 10,000 ug/plate in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. TIP was negative in these tests and the highest ineffective dose level tested in any Salmonella tester strain was 10,000 ug/plate./OTHER TOXICITY INFORMATION/ Diisopropanolamine, triisopropanolamine, isopropanolamine, & mixed isopropanolamine are used as water-soluble emulsifiers & neutralizers in cosmetic products at concns up to 1%. In animal studies these ingredients were slightly toxic to practically nontoxic to rats & guinea pigs via acute oral admin. Triisopropanolamine was relatively nontoxic to rats in the two subchronic oral studies. These ingredients were moderate skin irritants for rabbits. All four ingredients, when tested at 100% concns, were severe ocular irritants in rabbits. Products containing small amounts (1%) of diisopropanolamine or triisopropanolamine, isopropanolamine were not ocular irritants in rabbits. The triisopropanolamine salt was not mutagenic in Aspergillus nidulans. ... Clinical studies on cosmetic products containing no more than 1% diisopropanolamine or 1.1% triisopropanolamine were minimal skin irritant & contact sensitizers. It is concluded that diisopropanolamine, triisopropanolamine, isopropanolamine, & mixed isopropanolamine are safe as cosmetic ingredients in the present practices of use & concn. ... |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of triisopropanolamine with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Triisopropanolamine is expected to be stable to aqueous hydrolysis in the environment(2). Triisopropanolamine absorbs light at wavelengths >290 nm(3) and may be susceptible to direct photolysis by sunlight(SRC). |
| Probable Routes of Human Exposure | According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of triisopropanolamine is 1 to 99the data may be greatly underestimated(1).NIOSH (NOES Survey 1981-1983) has statistically estimated that 64,304 workers (8,631 of these are female) are potentially exposed to triisopropanolamine in the US(1). The most likely route of occupational exposure to triisopropanolamine is the dermal route, but inhalation exposure to aerosols is also possible(2). Because triisopropanolamine, or triisopropanolamine-derived fatty acid soaps and salts may be used in a wide variety of personal care products, the most likely route of consumer exposure to triisopropanolamine in these products would be via the dermal route(2). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3259 8/PG 2 |
| Zollcode | 2922 19 00 |
| RTECS-Nr. | UB8750000 |
| R-Sätze (R) | 36-52/53 |
| Toxizität | LD50 orally in Rabbit: 4000 mg/kg LD50 dermal Rabbit 10000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-61 |
| Gefahrenklasse | 8Aquatic Chronic 3Eye Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 122-20-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 275 °C |
Anwendungen & Verwendung
Beschreibung
Triisopropanolamine (TIPA), a tertiary alkanolamine, is majorly used as a grinding chemical that reduces agglomeration in the ball milling process and changes the particle distribution of the finished cement.
Verwenden
Triisopropanolamine is an amine used for a variety of industrial applications including as an emulsifier, stabilizer, and chemical intermediate. It is also used to neutralize acidic components of some herbicides. It is majorly used as a grinding chemical that reduces agglomeration in the ball milling process and changes the particle distribution of the finished cement.
Herstellung & Synthese
synthetische
The process involves preparing raw materials with a molar ratio of 1:3.00 to 3.05 using liquefied ammonia (pure ammonia) and propylene oxide. The reactor is decompressed to -0.098Mpa to remove oxygen, then deionized water is added to achieve a 28-60% concentration of ammoniacal liquor. The ammonia and propylene oxide are introduced in two batches: first, half the weight of liquefied ammonia is pumped into the still, followed by half the weight of propylene oxide at 20-50°C, maintaining an internal pressure below 0.5Mpa and a reaction temperature of 20-75°C. After adding propylene oxide, the mixture is kept for 1.0-3.0 hours. Then, under the same conditions, the second half of the liquefied ammonia and propylene oxide are added, and the reaction continues for another 1.0-3.0 hours at 20-120°C. After the reaction, the pressure in the reactor is reduced to remove moisture and low-boiling impurities, resulting in a Triisopropanolamine product with less than 5% water content.