Dabco
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Dabco
structure -
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CAS No:
280-57-9
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Formula:
C6H12N2
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Chemical Name:
Dabco
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Synonyms:
1,4-Diazabicyclo[2.2.2]octane;Bicyclo[2.2.2]-1,4-diazaoctane;N,N′-endo-Ethylenepiperazine;Triethylenediamine;Dabco;1,4-Ethylenepiperazine;Dabco 33LV;D 33LV;Thancat TD 33;TED;TEDA;Texacat TD 100;L 33;Niax A 33;Tegamine 33;Thancat TD 33A;Texacat TD 33;A 33;Dabco L 1202;Minico L 1020;Dabco S 25;TEDA L 33;LC 96003;Toral SM 2;Dabco Crystalline;Toyocat L 33;Dabco 3LV;PC CAT TD 33;NSC 56362;Polycat 33LV;Tego Amine;Jeffcat TD 100;TD 100;Toyocat TEDA L 33;L 33E;33LV;Activator 105E;Dabco Crystal;LV 33;Kaolizer 31;PC-TD;AE 33;Tegoamin 33;S 25;TEDA-L 33B;Dabco A 33;PT 301;PT 301 (catalyst);A 33LV;Catalyst A 33;TEDA 33P;33LSI;Lupragen N 201;Dabco H 1010;Amicure TEDA;S 33;Dabco D 0134;Dabco 33;PUR 812;Dabco 33S;TEDA-L 25B;TEDA 33;23790-33-2;88935-43-7;101484-19-9;150605-01-9;165724-47-0;203072-11-1;309955-09-7;682335-96-2;746642-46-6;903524-95-8;1357848-51-1;2260745-52-4
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CAS No:
Description
Dabco, whose chemical name is 1, 4-diazadicyclic [2.2.2] octane, has CAS number 280-57-9. The chemical formula of this organic heterocyclic compound is. C₆H₁₂N₂. Dabco usually appears as a white crystalline powder, but it can also exist in a variety of forms, such as liquid or large granular crystals, depending on the preparation conditions. Its unique molecular structure, which consists of piperazine rings and ethane-1, 2-digroups forming a bridge between the N1 and N4 atoms, gives Dabco its unique chemical properties and functions. Dabco has a wide range of applications in the chemical industry, where it is commonly used as a catalyst for polymerization reactions. By acting as a catalyst, Dabco is able to significantly increase the rate and efficiency of polymerization reactions, thereby optimizing the production process. In addition to acting as a catalyst, Dabco also acts as a reagent and antioxidant in chemical synthesis, and is able to participate in a variety of chemical reactions and play multiple roles. As a bridging compound and tertiary amino compound, Dabco occupies an important position in the field of saturated organic heterocyclic compounds. Due to its unique chemical properties and good catalytic properties, Dabco is widely used in various industries such as pharmaceuticals, plastics and coatings. In the pharmaceutical industry, Dabco can be used as an intermediate or catalyst to help synthesize complex drug molecules. In the plastics industry, Dabco acts as a catalyst to improve the production efficiency and quality of polymers. In the coatings industry, Dabco's antioxidant properties make it an important additive to improve the stability and durability of coatings. Dabco is favored in industrial applications due to its outstanding performance in materials science and chemical engineering. Its unique chemical structure and versatility make it a key ingredient in many chemical reactions and industrial processes. With the continuous progress of science and technology, Dabco's application areas and potential are still expanding, making important contributions to the development of the chemical industry.
Dabco Basic Attributes
112.17
112.17
103618
205-999-9
X8M57R0JS5
56362
DTXSID0022016
Colorless hygroscopic crystals
29335920
Characteristics
6.5
-0.2
White to pale yellow Hygroscopic Crystals
1.14 g/cm3 @ Temp: 28 °C
158 °C
174 °C
198 °F
1.561
H2O: 46 g/100 mL (26 ºC)
2-8°C
2.9 mm Hg ( 50 °C)
LD50 orally in Rabbit: 700 mg/kg
2.20e-11 cm3/molecule*sec
Henry's Law constant = 4.7X10-9 atm-cu m/mol at 25 °C (est)
pKa1 = 3.0; pKa2 = 8.7
Extremely hygroscopic; sublimes readily at room temperature|Hydroxyl radical reaction rate constant = 2.2X10-11 cu cm/molecule-sec at 25 °C
61.9 kJ/mol (heat of sublimation below 75 °C)
Safety Information
III
8
UN 1325 4.1/PG 2
1
22-36/37/38-52/53-41-36/38-11
26-60-37/39-3-16-36/37-61
HM0354200
Xn,F
Stable, but very hygroscopic. Incompatible with strong oxidizing agents, strong acids. Highly flammable.
P261-P273-P305 + P351 + P338
H315-H319-H335-H412
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.
... In paint manufacture, preliminary small-scale (12 g) tests in which ethyl acetate soln of cellulose nitrate and the other components were mixed in a lagged boiling tube showed large exotherms (which boiled the solvent off) with 1,4-diazabicyclo(2.2.2)octane ... Subsequent test in which small portions of ... undiluted /1,4-diazabicyclo(2.2.2.)octane/ and dried cellulose nitrate linters were contacted (with a little added butyl acetate for the solid phenol) under various condition ... ignition /occurred/ ...|Activated carbon showed an auto-ignition temp in flowing air of 452 to 518 °C. Presence of 5% of ... triethylenediamine adsorbed on the carbon reduced the autoignition temp (AIT) to 230 to 260 °C. At high air flow rates an exotherm was seen at 230 to 260 °C but ignition did not then occur until 500 °C.|A sample of the 1:1 complex /of 1.4-diazabicyclo(2.2.2)octane and hydrogen peroxide/exploded while being dried overnight in a desiccator.
|Danger|H228 (72.15%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, and P501|Aggregated GHS information provided by 796 companies from 39 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P309+P311, P314, P321, P330, P332+P313, P337+P313, P362, P405, and P501
/GUIDE 133: FLAMMABLE SOLIDS/ Fire or Explosion: Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/|/GUIDE 133: FLAMMABLE SOLIDS/ Health: Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/|/GUIDE 133: FLAMMABLE SOLIDS/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/|/GUIDE 133: FLAMMABLE SOLIDS/ Protection Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/|For more DOT Emergency Guidelines (Complete) data for 1,4-DIAZABICYCLO(2.2.2)OCTANE (8 total), please visit the HSDB record page.
Toxicity
LD50 Rat oral 1700 mg/kg|LD50 Rabbit oral 1100 mg/kg|LD50 Guinea pig oral 2250 mg/kg
Triethylenediamine's production and use as a catalyst in the manufacture of urethane foams(1,2) 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 3.4(SRC), determined from a water solubility of 450 g/L(2) and a regression-derived equation(3), indicates that triethylenediamine is expected to have very high mobility in soil(SRC). The pKa1 and pKa2 of triethylenediamine are 3.0 and 8.7, respectively(2), indicating that this compound will primarily exist in cation form in the environment and cations generally have lower mobility in soils than their neutral counterparts(4). Volatilization of triethylenediamine from moist soil surfaces is not expected to be an important fate process, since this compound is expected to primarily exist in the cation form in the environment(SRC). Triethylenediamine is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.742 mm Hg(5). A 0% theoretical BOD in 4 weeks using the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990) (4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000) (5) Yaws CL; Handbook of Vapor Pressure. Volume 2 - C5 to C7 Compounds. Gulf Publishing Co.: Houston, TX, p. 190 (1994) (6) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.4(SRC), determined from a water solubility of 450 g/L(2) and a regression-derived equation(3), indicates that triethylenediamine is not expected to adsorb to suspended solids and sediment(SRC). The pKa1 and pKa2 of triethylenediamine are 3.0 and 8.7, respectively(2), which indicate triethylenediamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), a BCF values of <1.3 and <13(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 0% theoretical BOD in 4 weeks using the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in water(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990) (4) Franke C et al; Chemosphere 29: 1501-14 (1994) (5) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylenediamine, which has a vapor pressure of 0.742 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylenediamine 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 18 hours(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(3). Triethylenediamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).
The rate constant for the vapor-phase reaction of triethylenediamine with photochemically-produced hydroxyl radicals has been reported to be 2.2X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Triethylenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Triethylenediamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3).
BCF values of <1.3 and <13 were measured using carp (Cyprinus carpio) which were exposed over an 6-week period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).[(1) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo
The Koc of triethylenediamine is estimated as 3.4(SRC), using a water solubility of 450 g/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that triethylenediamine is expected to have very high mobility in soil(SRC). The pKa1 and pKa2 values of triethylenediamine are 3.0 and 8.7(1), respectively, indicating that this compound will primarily exist in the cation form in the environment and cations generally have lower mobility in soils than their neutral counterparts(4).
Volatilization from water and moist soil surfaces is not expected to occur since triethylenediamine will exist primarily in the cation form in the environment(SRC), based on its pKa1 and pKa2 values of 3.0 and 8.7, respectively(1). Triethylenediamine is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.742 mm Hg(2).
Occupational exposure to triethylenediamine may occur through inhalation and dermal contact with this compound at workplaces where triethylenediamine is produced or used(SRC). Triethylenediamine concentrations in air in a polyurethane factory ranged from 0.017 to 0.110 ppm(1).
Drug Information
Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)
/SIGNS AND SYMPTOMS/ ...Can cause corneal disturbance in workers exposed to the vapor. It is reported to have induced fine corneal epithelial edema & to have caused people to see haloes around lights several hours after exposure.
1,4-diazabicyclo(2.2.2)octane
Dabco Use and Manufacturing
1, 2-Dichloroethane and ammonia water are fed into the tubular reactor, and are heated and autoclaved at 150-250°C under a pressure of 392 kPa. The reaction solution is neutralized with alkali to obtain mixed free amine, concentrated to remove sodium chloride, then the crude Lv is distilled under reduced pressure, and different fractions are collected for separation. At the same time of obtaining the product, it also produces ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine and polyethylenepolyamine in parallel. This product can be obtained by fractional distillation from the mother liquor producing piperazine hexahydrate, and the first production of 100t piperazine hexahydrate can obtain about 3-4t of triethylenediamine hexahydrate.
Catalyst in making urethane foams.
1,000,000 - 10,000,000 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).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5439]
All other basic organic chemical manufacturing|1,4-Diazabicyclo[2.2.2]octane: ACTIVE|Triethylenediamine is used to impregnate the activated carbon found in respiratory protection against chemical weapon agents.|Certain low-molecular chemical weapon agents such as hydrogen cyanide and cyanogen chloride are poorly absorbed by active carbon. In order to improve protection against these substances, the carbon is impregnated with metallic salts of copper, chromium and sometimes silver. Further impregnation with organic substances also occurs, the most common additive being triethylenediamine.
Gas chromatographic identification & separation of piperazine derivatives were achieved with good reproducibility.|Method: NIOSH 2540, issue 2; Procedure: high performance liquid chromatography with ultraviolet detection; Analyte: naphthylisothiourea derivative of analytes; Matrix: air; Detection Limit: 0.9 ug per sample. /Ethylenediamine/
Computed Properties
Molecular Weight:112.17
XLogP3:-0.2
Hydrogen Bond Acceptor Count:2
Exact Mass:112.100048391
Monoisotopic Mass:112.100048391
Topological Polar Surface Area:6.5
Heavy Atom Count:8
Complexity:61.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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