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Diethylhydroxylamine

Diethylhydroxylamine structure

Diethylhydroxylamine 

structure
  • CAS No:

    3710-84-7

  • Formula:

    C4H11NO

  • Chemical Name:

    Diethylhydroxylamine

  • Synonyms:

    Ethanamine,N-ethyl-N-hydroxy-;N-Ethyl-N-hydroxyethanamine;N,N-Diethylhydroxylamine;N-Hydroxydiethylamine;Diethylhydroxylamine;DEHA

  • Categories:

    Water Treatment Chemical  >  Corrosion Inhibitor

Description

liquid


Liquid

Diethylhydroxylamine Basic Attributes

89.1362

89.14

223-055-4

314I05EDVH

DTXSID2027543

Liquid

2928000090

Characteristics

23.47

0.7174

Light yellow liquid

0.8612 g/cm3 @ Temp: 25 °C

10 °C

133 °C

115 °F

n20/D 1.420(lit.)

H2O: soluble

Flammables area

4 mm Hg ( 0 °C)

3.07 (vs air)

LD50 orally in Rabbit: 2190 mg/kg LD50 dermal Rabbit 1300 mg/kg

1.01e-10 cm3/molecule*sec

Henry's Law constant = 5.9X10-8 atm-cu m/mol at 25 °C (est)

pKa = 5.67 (est)

Hydroxyl radical reaction rate constant = 1.01X10-10 cu cm/molecule-sec at 25 °C

Critical temperature = 567 Kelvin; Critical pressure = 4.13X10+6 Pa

Safety Information

III

3

UN 1993 3/PG 3

1

R10; R20/21; R36/37/38; R40

S36/37-S45-S36/37/39-S26-S16

NC3500000

Xn

Stable. Hygroscopic. Flammable. Incompatible with strong oxidizing agents, strong acids.

P280-P305 + P351 + P338

H226-H312 + H332-H315-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.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from the Database Query page at: http://www.epa.gov/hpv/pubs/hpvrstp.htm on Diethylhydroxylamine as of March 11, 2008.

|Warning|H226 (99.81%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 574 companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P309+P311, P312, P322, P363, P370+P378, P403+P235, P405, and P501

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Combustible

If material on fire or involved in fire: Do not extinguish fire unless flow can be controlled. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with material anticipated, wear appropriate chemical protective clothing.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxicity

LC50 Rat (Sprague Dawley) inhalation 3140 ppm/4 hr|LD50 Rat (WBS/W, male) oral 2190 mg/kg|LD50 Rabbit (albino) dermal 1300 mg/kg

Diethylhydroxylamine's production and use as photographic developer, antioxidant, corrosion inhibitor(1) and as a shortstopping agent in synthetic rubber production(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 74(SRC), determined from a structure estimation method(2), indicates that diethylhydroxylamine is expected to have high mobility in soil(SRC). The estimated pKa of diethylhydroxylamine is 5.7(3), indicating it will partially exist in the protonated form in moist soils. The mobility of diethylhydroxylamine may be overestimated since cations generally adsorb more strongly to soils containing organic carbon and clay than neutral species(4). Volatilization from moist soil surfaces is not expected to be an important fate process(SRC) based upon an estimated Henry's Law constant of 5.9X10-8 atm cu m/mol atm-cu m/mole(SRC), developed using a fragment constant estimation method(5), and the fact that cations do not volatilize. The potential for volatilization of diethylhydroxylamine from dry soil surfaces may exist(SRC) based upon an extrapolated vapor pressure of 3.36 mm Hg at 25 °C(6). Diethylhydroxylamine was biodegraded between 1-9% in the Japanese MITI test(7), suggesting it may be slow to biodegrade in soil.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 74(SRC), determined from a structure estimation method(2), indicates that diethylhydroxylamine is not expected to adsorb to suspended solids and sediment(SRC). The estimated pKa of diethylhydroxylamine is 5.7(3), indicating it will partially exist in the protonated form in water. As a result, diethylhydroxylamine may have greater adsorption to suspended solids and sediment than its estimated Koc value indicates(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 5.9X10-8 atm cu m/mol atm-cu m/mole(SRC), developed using a fragment constant estimation method(5), and the fact that cations do not volatilize. According to a classification scheme(6), an estimated BCF of 3(SRC), from a log Kow of -0.17(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethylhydroxylamine was biodegraded between 1-9% in the Japanese MITI test(7), suggesting it may be slow to biodegrade in water.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylhydroxylamine, which has a vapor pressure of 3.36 mm Hg at 25 °C(2), is expected to exist solely in the vapor phase in the ambient atmosphere. Vapor-phase diethylhydroxylamine 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), calculated from its rate constant of 1.01X10-10 cu cm/molecule-sec at 25 deg(3). Diethylhydroxylamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to undergo direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of diethylhydroxylamine with photochemically-produced hydroxyl radicals has been measured as 1.01X10-10 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 4 hours(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diethylhydroxylamine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Diethylhydroxylamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to undergo direct photolysis by sunlight(2).

An estimated BCF of 3 was calculated in fish for diethylhydroxylamine(SRC), using a log Kow of -0.17(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).

Using an estimation method based on molecular connectivity indices(1), the Koc for diethylhydroxylamine is estimated to be 74(SRC). According to a suggested classification scheme(2), this Koc value suggests that diethylhydroxylamine will have high mobility in soil(SRC). The estimated pKa of diethylhydroxylamine is 5.7(3), indicating it will partially exist in the protonated form in moist soils. As a result, the mobility of diethylhydroxylamine may be overestimated since cations generally adsorb more strongly to soils containing organic carbon and clay than neutral species(4).

Diethylhydroxylamine is a weak base with an estimated pKa of 5.7(1). This estimated pKa indicates diethylhydroxylamine will partially exist in the protonated form in the environment. Volatilization from moist soil and water is not expected since cations do not volatilize and the estimated Henry's Law constant for the neutral species (free base) of diethylhydroxylamine is 5.9X10-8 atm cu m/mol(SRC), using a fragment constant estimation method(2). The potential for volatilization of diethylhydroxylamine from dry soil surfaces may exist(SRC) based upon an extrapolated vapor pressure of 3.36 mm Hg at 25 °C(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 950 workers (14 of these were female) were potentially exposed to diethylhydroxylamine in the US(1). Occupational exposure to diethylhydroxylamine may occur through inhalation and dermal contact with this compound at workplaces where diethylhydroxylamine is produced or used(SRC).

Drug Information

The effects of diethylhydroxylamine (DEHA), a potent free-radical scavenger, on lipid peroxidation of rat liver microsomes were investigated in vitro. DEHA strongly inhibited ascorbate-dependent nonenzymatic microsomal lipid peroxidation. DEHA also completely inhibited nonenzymatic lipid peroxidation of heat-denatured microsomes, indicating that inhibition is protein-independent. DEHA only moderately inhibited NADPH-dependent enzymatic microsomal lipid peroxidation. DEHA has been shown to exhibit antitumorigenic properties. However, it had no significant effect on hepatic glutathione S-transferase, selenium-independent glutathione peroxidase, or selenium-dependent glutathione peroxidase activity in the DEHA-treated CD-1 (lCR) Br male mouse. This suggests that the mode of action of DEHA as an antitumorigenic agent may be different from that of butylated hydroxyanisole, whose antitumor function is attributed to induction of glutathione S-transferase activity.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/CASE REPORTS/ A 39-year-old man committed suicide by ingesting a large quantity of SH792. SH792 is a silicone resin precursor used as a hardener for waterproof paints. It is polymerized in water; this process is then followed by the formation of silicone resin and the release of N,N-diethylhydroxylamine. In this decedent, analysis by infrared spectroscopy showed that polymerized silicone resin was present in the stomach contents. The amount of silica in his tissues was within levels seen in control subjects. N,N-diethylhydroxylamine was detected in the urine (0.7 microliters/mL) but not in the stomach contents ...

diethylhydroxylamine

Diethylhydroxylamine Use and Manufacturing

Methods of Manufacturing

1. Oxidation of the secondary amine with an aqueous hydrogen peroxide solution in the presence of a catalyst cadmium salt (CdCl2.2H2O) or a zinc salt (ZnCl2) or oxidation of a dialkylamine with an aqueous hydrogen peroxide solution in the presence of a titanium silicalite catalyst RRNH) or triethylamine can be prepared this product.
2. In the presence of a titanium silicalite catalyst, the dialkylamine is oxidized with hydrogen peroxide to produce diethylhydroxylamine. Hydrogen peroxide is a 30% aqueous solution. Titanium silicalite catalyst to research into fine powder. The reaction temperature was about 80 ° C. In the operation, the catalyst and the dialkylamine (e.g., diethylamine) are first placed in the reactor, and then the temperature is raised to about 80 ° C, and an aqueous solution of hydrogen peroxide is slowly added to 35MIN under stirring. Yields of up to 87.1%. Dihydroxyhydroxylamine can also be prepared by catalytic oxidation of nitric acid (C2OH16N4).

Uses

1. As a vinyl monomer, used in efficient inhibitor agent of conjugate olefins.
2. In liquid or gas phase, if end gather seed is existed,it can be used as inhibitors of end gather.
3. It's a excellent end agent in process of Emulsion-polymerized styrene butadiene rubber.
4. It's a antioxidants of the unsaturated oil and resin.
5. In the environmental protection,it鈥檚 good photochemical smoke inhibitors.
6. It's used as corrosion inhibitors in the equipment of the boiler feed water and steam heat exchange.
7. It's used as antioxidant in photography screens potions. Pay attention to level, it must be the photography level,and appearance is colorless liquid. Industrial level can not be used here.


3.A.1 - Short-Stopper in rubber production


Floor coverings

Production

1,000,000 - 10,000,000 lb|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#6317]|Ethanamine, N-ethyl-N-hydroxy- is listed as a High Production Volume (HPV) chemical (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).

Grade: 85%

All other chemical product and preparation manufacturing|Ethanamine, N-ethyl-N-hydroxy-: ACTIVE

Computed Properties

Molecular Weight:89.14
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:89.084063974
Monoisotopic Mass:89.084063974
Topological Polar Surface Area:23.5
Heavy Atom Count:6
Complexity:26.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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