Dibutyl phosphate
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Dibutyl phosphate
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CAS No:
107-66-4
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Formula:
C8H19O4P
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Chemical Name:
Dibutyl phosphate
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Synonyms:
Phosphoric acid,dibutyl ester;Butyl phosphate,(BuO)2(HO)PO;Dibutyl phosphate;Dibutyl hydrogen phosphate;Di-n-Butyl phosphate;Dibutyl acid phosphate;DP 4 (coupling agent);HDBP;DP 4;NSC 203039;NSC 22313;DBP;72283-56-8
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CAS No:
Description
Pale-amber, odorless liquid.
Dibutyl phosphate is a pale-amber odorless liquid. Mp: -13°C, bp: 135-138°C. Density: 1.06 g cm-3. Moderately soluble in water (18 g / L at 20°C).|Liquid|COLOURLESS LIQUID.|Pale-amber, odorless liquid.
Dibutyl phosphate is a pale-amber odorless liquid. Mp: -13°C, bp: 135-138°C. Density: 1.06 g cm-3. Moderately soluble in water (18 g / L at 20°C).|Dibutyl phosphate is a dialkyl phosphate.
Dibutyl phosphate Basic Attributes
210.208
210.21
203-509-8
0072NN74TN
1278
289390
1718
DTXSID3040728
Pale-amber liquid or oil
2919900090
Characteristics
65.57000
2.20
Dibutyl phosphate is a pale-amber odorless liquid. Mp: -13°C, bp: 135-138°C. Density: 1.06 g cm-3. Moderately soluble in water (18 g / L at 20°C).
1.06 g/cm3
-13 °C
135 °C
120.3±22.6 °C
1.436
Insoluble
1 mmHg (approx)
Relative vapour density (air = 1): 7.2
Combustible Liquid
Odorless
MODERATELY STRONG MONOBASIC ACID
Henry's Law constant = 4.3X10-9 atm-cu m/mol at 25 °C (est)
pKa = 0.88 (est)
167.54 Ų [M+Na]+
Decomposes >100 °C|Hydroxyl radical reaction rate constant = 5.3X10-11 cu cm/molec-sec at 25 °C (est)
No rapid reaction with air No rapid reaction with water
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
DIBUTYL PHOSPHATE Is non-flammable, but combustible (flash point 188°C). Auto-ignition temperature is 420°C. Emits irritating or toxic fumes in a fire. Is a moderately strong acid obtained by the partial esterification of phosphoric acid. Reacts exothermically and vigorously with bases. Incompatible with strong oxidizing agents, alkali metals, heat, or plastic. Reacts with many metals liberating flammable/explosive hydrogen gas.
420 °C
Combustible Liquid
Safety Information
III
8
3261
1
R34;R38;R41
S26-S39-S45-S36/37/39-S25
TB9605000
C:Corrosive;Xi:Irritant;
Separated from strong oxidants and strong bases.
P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338
H314-H351
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.
Strong oxidizers.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.|Flammable - 2nd degree
|Danger|H314 (97%): 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, P363, P405, and P501|Aggregated GHS information provided by 803 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|Use powder, AFFF, foam, carbon dioxide.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Respirator Recommendations: Up to 10 ppm: (Assigned Protection Factor = 10) Any supplied-air respirator.|Respirator Recommendations: Up to 25 ppm: (Assigned Protection Factor = 25) Any supplied-air respirator operated in a continuous-flow mode.|For more Personal Protective Equipment (PPE) (Complete) data for DIBUTYL PHOSPHATE (8 total), please visit the HSDB record page.|(See protection codes)
Extremely flammable
1. Ventilate area of spill or leak. 2. Collect for reclamation or absorb in vermiculite, dry sand, earth, or a similar material.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.|The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|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.
Dibutyl phosphate may cause irritation of the eyes, nose, throat, & lungs. Repeated or prolonged exposure to dibutyl phosphate may cause irritation of the skin.
Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 1 ppm (5 mg/cu m).|Vacated 1989 OSHA PEL TWA 1 ppm (5 mg/cu m); STEL 2 ppm (10 mg/cu m) is still enforced in some states.
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 1 ppm (5 mg/cu m).|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 2 ppm (10 mg/cu m).
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize spilled liquid. Then wash away with plenty of water.
Separated from strong oxidants and strong bases.
A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
The substance is irritating to the eyes, skin and respiratory tract.
NO open flames.
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves.
Wear safety goggles or face shield.
Toxicity
LD50 Rat oral 3,200 mg/kg
Dibutyl phosphate's production and use as a catalyst, an antifoaming agent, and in metal separation and extraction(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 490(SRC), determined from a water solubility of 1.72X10+4 mg/L(2) and a regression-derived equation(3), indicates that dibutyl phosphate is expected to have moderate mobility in soil(SRC). The pKa of dibutyl phosphate is 0.88(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of dibutyl phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Dibutyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.8X10-5 mm Hg(SRC), determined from a fragment constant method(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 490(SRC), determined from a water solubility of 1.72X10+4 mg/L(2) and a regression-derived equation(3), indicates that dibutyl phosphate is 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 4.3X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa of dibutyl phosphate is 0.88(5), indicating that this compound will primarily exist as an anion in the environment and anions generally do not adsorb more strongly to organic carbon than their neutral counterparts(6). The sorption of organophosphorus compounds in soil depends on both organic matter and clay content of soil and the sorption increases as the pH of soil decreases(7), therefore, adsorption to suspended solids and sediments is expected to be pH dependent. According to a classification scheme(8), an estimated BCF of 66(SRC), from a measured water solubility(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Dibutyl phosphate, present at 4.4 mg/L, reached 12% of its theoretical oxygen demand in 28 days using a municipal sludge inoculum in a closed bottle test(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyl phosphate, which has an estimated vapor pressure of 3.8X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dibutyl phosphate 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 7.3 hours(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dibutyl phosphate may be removed from the air by wet or dry deposition(SRC). Dibutyl phosphate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of dibutyl phosphate with photochemically-produced hydroxyl radicals has been estimated as 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dibutyl phosphate may be susceptible to hydrolysis in the environment due to the presence of functional groups (esters) that hydrolyze under environmental conditions(2). The hydrolysis half-life of the analog dimethyl phosphoric acid in neutral solution at 100 °C was found to be 2.4 days(3). Increasing the carbon chain substituent on phosphoric acid (as in the case of dibutyl phosphate) may not increase the rate of hydrolysis(3). Dibutyl phosphate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 66 was calculated for dibutyl phosphate(SRC), using a water solubility of 1.72X10+4 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).
The Koc of dibutyl phosphate is estimated as 490(SRC), using a water solubility of 1.72X10+4 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dibutyl phosphate is expected to have moderate mobility in soil. The estimated pKa of dibutyl phosphate is 0.88(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5). The sorption of organophosphorus compounds in soil depends on both organic matter and clay content of soil and the sorption increases as the pH of soil decreases(6).
The Henry's Law constant for dibutyl phosphate is estimated as 4.3X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dibutyl phosphate is expected to be essentially nonvolatile from water surfaces(2). Dibutyl phosphate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). Dibutyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.8X10-5 mm Hg(SRC), determined from a fragment constant method(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,321 workers are potentially exposed to dibutyl phosphate in the US(1). Occupational exposure to dibutyl phosphate may occur through the respiratory tract and dermal contact with this compound at workplaces where dibutyl phosphate is produced or used(2).
Drug Information
Tributyl phosphate (20%); Monobutyl phosphate (16%)
Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, respiratory system; headache Target Organs: Eyes, skin, respiratory system (NIOSH, 2016)
Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
/SIGNS AND SYMPTOMS/ Some workers exposed to dibutyl phosphate have complained of respiratory tract irritation and headache.|/SIGNS AND SYMPTOMS/ Dibutyl phosphate may cause irritation of the eyes, nose, throat, and lungs. It may also cause headaches. Repeated or prolonged exposure to dibutyl phosphate may cause irritation of the skin.
di-n-butylphosphoric acid
The substance can be absorbed into the body by inhalation of its aerosol.|inhalation, ingestion, skin and/or eye contact
irritation eyes, skin, respiratory system; headache
Cough. Headache. Sore throat.
Redness. Pain.
Redness. Pain.
Eyes, skin, respiratory system
Dibutyl phosphate Use and Manufacturing
Finishing agents
Lubricants and greases
1,000,000 - 10,000,000 lb|(1986) 10 thousand-500 thousand pounds|(1990) 10 thousand-500 thousand pounds|(1994) 10 thousand-500 thousand pounds|(1998) 10 thousand-500 thousand pounds|(2002) 10 thousand-500 thousand pounds
All other basic organic chemical manufacturing|Phosphoric acid, dibutyl ester: ACTIVE
Method: NIOSH 5017, Issue 2; Procedure: gas chromatography with phosphorus flame photometric detector; Analyte: dibutyl phosphate; Matrix: air; Detection Limit: 0.07 mg/sample.
Fire Hazards -> Flammable - 2nd degree
Computed Properties
Molecular Weight:210.21
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:210.10209608
Monoisotopic Mass:210.10209608
Topological Polar Surface Area:55.8
Heavy Atom Count:13
Complexity:146
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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