기본 정보
- 표준 SMILES
CCCCC(CC)COP(=O)(O)OCC(CC)CCCC- InChIKey
SEGLCEQVOFDUPX-UHFFFAOYSA-N- 분자식
- C16H35O4P
- 평균 분자량
- 322.42 g/mol
- 단동위원소 질량
- 322.22729623
개요
Di-(2-ethylhexyl)phosphoric acid is an odorless light yellow liquid. Floats on water. (USCG, 1999)
이름 및 식별자
- 우선 이름
- Bis(2-ethylhexyl) phosphate
- IUPAC
- bis(2-ethylhexyl) hydrogen phosphate
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
298-07-7- PubChem CID
- 9275
- DTXSID
DTXSID1027134- ChEMBL
CHEMBL1902443- UNII
- 2Z4W0L3H06
- EC Number
- 206-056-4
- Nikkaji
- J34.641A
물성
구조 계산 물성
- XLogP
- 5.2
- 극성 표면적
- 55.8 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 14
- 무거운 원자 수
- 21
- 형식 전하
- 0
- 복잡도
- 259
실험 및 물리화학적 성질
Chemical Classes
Other Classes -> Organophosphates, Other
Corrosives
Organophosphate diesters (OPDE)
Organophosphate
Density
0.977 at 68 °F (USCG, 1999) - Less dense than water; will float
0.975 g/cu cm at 25 deg
Strongly acidic. Bulk density Wt/gal = 8.2 lb
0.96 g/cm³
0.97525 @25 °C
Color/Form
Viscous liquid
Amber liquid
Solubility
Soluble in benzene, hexane, and 4-methyl-2-pentanone
In water, 1.82X10+2 mg/L at 25 °C
Solubility in water, g/100ml at 20 °C: 0.21
Flash Point
385 °F (USCG, 1999)
Flash point equals 385 °F
385 °F (196 °C) (Open cup)
About 198 °C (closed cup)
196 °C o.c.
Boiling Point
155 °C at 0.015 mm Hg
155.015 °C @760 [mm Hg]
Decomposition
When heated to decomposition emits toxic fumes of /phosphorus oxides/.
240 °C. This produces toxic fumes of phosphorus oxides. Attacks many metals. This produces flammable/explosive gas (hydrogen - see ICSC 0001).
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 3.9% (42 of 1068) of reports.
Danger
H302+H312 (41.3%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P332+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1068 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
유해성 정보
Regulatory Information
Chemical: Phosphoric acid, bis(2-ethylhexyl) ester
Phosphoric acid, bis(2-ethylhexyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphoric acid, bis(2-ethylhexyl) ester 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: 17-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5599
Di(2-ethylhexyl)phosphate: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Irritating phosphorus oxides may be released. (USCG, 1999)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Fire Potential
Slight, when exposed to heat or flame.
May form flammable hydrogen gas.
Special Reports
The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environment fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from: http://www.epa.gov/chemrtk/viewsrch.htm on phosphates as of January 19, 2006. /Phosphates/
WHO; Diseases Caused by Phosphorus and Its Toxic Compounds; Early Detection of Occupational Diseases pg 53-62 (1986). Review of diseases and health related effects resulting from exposure to phosphorus or phosphorus cmpd.
TSCA Requirements
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bis(2-ethylhexyl)phosphate is included on this list.
Reactivity Profile
Organophosphates, such as DI-(2-ETHYLHEXYL)PHOSPHORIC ACID, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Mildly corrosive to most metals; may form flammable hydrogen gas (USCG, 1999).
안전 및 보호
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer for medical attention .
Disposal Methods
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.
Spillage Disposal
Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking liquid in covered dry plastic containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures
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.
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.
독성 정보
Ecotoxicity Values
LC50 Danio rerio (Zebra danio) >56 mg/L/96 hr; static /formulated product/
LC50 Daphnia magna (Water flea) >42 mg/L/24 hr; static /formulated product/
LC50 Daphnia magna (Water flea) >42 mg/L/48 hr; static /formulated product/
LC50 Daphnia magna (Water flea) 46.8 mg/L/72 hr (95% confidence limit: 19.8-110.0); static /formulated product/
For more Ecotoxicity Values (Complete) data for BIS(2-ETHYLHEXYL) PHOSPHATE (7 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+4(SRC), determined from a structure estimation method(2), indicates that bis(2-ethylhexyl) phosphate is expected to be immobile in soil(SRC). The estimated pKa of bis(2-ethylhexyl) phosphate is 1.47(3), 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(4). Volatilization of bis(2-ethylhexyl) phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Bis(2-ethylhexyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-8 mm Hg(SRC), determined from a fragment constant method(6). Bis(2-ethylhexyl) phosphate, present at 100 mg/L, reached 0-17% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(7) and therefore this compound may not biodegrade rapidly in terrestrial environments(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+4(SRC), determined from a structure estimation method(2), indicates that bis(2-ethylhexyl) 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 4.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa of bis(2-ethylhexyl) phosphate is 1.47(5), indicating that this compound will primarily exist in anion form 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). In a study on the sorption of bis(2-ethylhexyl) phosphate on kaolinite and amectite, the acidic phosphoric group reacted rapidly and almost irreversibly with the surface cations of the clay mineral structure(7), therefore, adsorption to suspended solids and sediments is expected to be pH dependent. According to a classification scheme(8), measured BCF values of 1-2.4 and 2.7-6.0(9) suggest the potential for bioconcentration in aquatic organisms is low(SRC). Bis(2-ethylhexyl) phosphate, present at 100 mg/L, reached 0-17% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(9) and therefore this compound is not expected to biodegrade rapidly in aquatic environments(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-ethylhexyl) phosphate, which has an estimated vapor pressure of 4.7X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bis(2-ethylhexyl) phosphate may be removed from the air by wet or dry deposition(SRC). Bis(2-ethylhexyl) 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).
Signs and Symptoms
Burning sensation. Cough. Sore throat.
Redness. Burning sensation. Pain. Blisters.
Redness. Pain. Severe burns.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of bis(2-ethylhexyl) phosphate can be estimated to be 1.7X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that bis(2-ethylhexyl) phosphate is expected to be immobile in soil. The estimated pKa of bis(2-ethylhexyl) phosphate is 1.47(3), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon than their neutral counterparts(4). 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(5). In a study on the sorption of bis(2-ethylhexyl) phosphate on kaolinite and amectite, the acidic phosphoric group reacted rapidly and almost irreversibly with the surface cations of the clay mineral structure(5).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Causes smarting of skin and first degree burns on short exposure and may cause second degree burns on long exposure. Irritating to skin and eyes.
/SIGNS AND SYMPTOMS/ Inhalation: Burning sensation. Cough. Sore throat.; Skin: Redness. Burning sensation. Pain. Blisters.; Eyes: Redness. Pain. Severe deep burns.
Artificial Pollution Sources
Bis(2-ethylhexyl) phosphate's production and use as a metal extraction agent, a textile lubricant and antistatic agent, an extreme pressure additive, an intermediate for wetting agents and detergent, and a feedstock for chemical synthesis(1-3) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
AEROBIC: Bis(2-ethylhexyl) phosphate, present at 100 mg/L, reached 0-17% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1); therefore, this compound is not expected to biodegrade rapidly(SRC).
Environmental Bioconcentration
BCF values of 1-2.4 and 2.7-6.0 were measured for bis(2-ethylhexyl) phosphate at concentrations of 1 and 0.1 mg/L, respectively, using carp 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).
Volatilization from Water/Soil
The Henry's Law constant for bis(2-ethylhexyl) phosphate is estimated as 4.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(2-ethylhexyl) phosphate is expected to be essentially nonvolatile from water surfaces(2). Bis(2-ethylhexyl) phosphate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Bis(2-ethylhexyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-8 mm Hg(SRC), determined from a fragment constant method(3).
규제 정보
TSCA Requirements
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bis(2-ethylhexyl)phosphate is included on this list.
화학 및 산업
약리 정보
Metabolism/Metabolites
Plasma & tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric & phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Organophosphorus cmpd/
Absorption, Distribution and Excretion
Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/
Toxicants can be absorbed by inhalation, ingestion, and skin penetration. ...All undergo hydrolytic degradation in liver and other tissues, usually within hours of absorption. Degradation products are of low toxicity, and are excreted in urine and feces. /Organophosphate cholinesterase-inhibiting pesticides/
용도 및 제조
Uses
Used as a lubricant additive, a corrosion inhibitor, and a metal extractant; [HSDB]
Additive to lubrication oils, corrosion inhibitor and antioxidant
... Used as extractant in the hydrometallurgical separation of cobalt and nickel.
Metal extraction and separation, intermediate for wetting agents and detergents.
Basic drugs were quantitatively extracted from aq solution as ion-pair adducts, with di(2-ethylhexyl)phosphate in chloroform.
For more Uses (Complete) data for BIS(2-ETHYLHEXYL) PHOSPHATE (6 total), please visit the HSDB record page.
U.S. Production
2023: 550,000 - <700,000 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 G
(1975) PROBABLY GREATER THAN 4.54X10+5 G
(1986) >1 million-10 million pounds
For more U.S. Production (Complete) data for BIS(2-ETHYLHEXYL) PHOSPHATE (8 total), please visit the HSDB record page.
Methods of Manufacturing
... Produced by chlorinating bis(2-ethylhexyl) phosphonate to give the phosphate diester chloride, followed by hydrolysis, or by saponification of tris(2-ethylhexyl) phosphate
Formerly by reaction of phosphorus oxychloride and 2-ethylhexanol, followed by hydrolysis
General Manufacturing Information
Services
Phosphoric acid, bis(2-ethylhexyl) ester: ACTIVE
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