Bis(2-ethylhexyl) phosphate

HCID 9275

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Basic information

CAS
298-07-7
Standard SMILES
CCCCC(CC)COP(=O)(O)OCC(CC)CCCC
InChIKey
SEGLCEQVOFDUPX-UHFFFAOYSA-N
Molecular formula
C16H35O4P
Average molar mass
322.42 g/mol
Monoisotopic mass
322.22729623

Overview

Di-(2-ethylhexyl)phosphoric acid is an odorless light yellow liquid. Floats on water. (USCG, 1999)

Names & identifiers

Preferred name
Bis(2-ethylhexyl) phosphate
IUPAC
bis(2-ethylhexyl) hydrogen phosphate

Names & synonyms

Bis(2-ethylhexyl) hydrogen phosphate298-07-7BIS(2-ETHYLHEXYL) PHOSPHATEDi(2-ethylhexyl) phosphateBis(2-ethylhexyl)phosphateBis(2-ethylhexyl)phosphoric acidDi-2-ethylhexyl hydrogen phosphateBis(2-ethylhexyl)hydrogen phosphatePhosphoric acid, bis(2-ethylhexyl) esterDi(2-ethylhexyl)orthophosphoric acidHydrogen bis(2-ethylhexyl) phosphate2-Ethyl-1-hexanol hydrogen phosphate
Show more names
Di(2-ethylhexyl) phosphoric acidBis(2-ethylhexyl)orthophosphoric acidHSDB 341Di-2(ethylhexyl)phosphoric acidDTXSID1027134di-(2-ethylhexyl)phosphoric acidDi-(2-ethylhexyl) acid phosphateBis(2-ethylhexyl) phosphoric acid

Database identifiers

CAS
298-07-7
PubChem CID
9275
DTXSID
DTXSID1027134
ChEMBL
CHEMBL1902443
UNII
2Z4W0L3H06
EC Number
206-056-4
Nikkaji
J34.641A

Properties

Computed structural propertiesFilling in

XLogP
5.2
Topological polar surface area
55.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
14
Heavy atoms
21

Experimental & physicochemical properties

Chemical Classes · 4 items

Other Classes -> Organophosphates, Other

Corrosives

Organophosphate diesters (OPDE)

Organophosphate

SpringerMaterials PropertiesChemical diffusion
FragrancesFragrance Ingredient (Phosphoric acid, bis(2-ethylhexyl) ester) -> IFRA transparency List
LogP2.67
OdorODORLESS
Density · 5 items

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 5 items

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.)

DOT LabelCorrosive
Fire Hazards · 2 items

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 · 2 items

Slight, when exposed to heat or flame.

May form flammable hydrogen gas.

Health HazardsContact with liquid irritates eyes and may cause serious injury; consult an eye specialist. Also causes skin irritation on contact. Ingestion produces irritation similar to that caused by strong vinegar. (USCG, 1999)
Hazards SummaryA skin irritant; may cause corneal damage; [CAMEO] May cause second-degree burns after long exposure; [CHRIS]

Safety & protection

Fire Fighting · 2 items

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 · 4 items

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 .

First AidEYES: immediately flush with plenty of water for at least 15 min.; see a physician.
Safe StorageSeparated from metals.
Fire Fighting ProceduresExtinguish with dry chemical, alcohol foam or carbon dioxide; water or foam may cause frothing.
Cleanup MethodsCollect leaking liquid in covered dry, plastic containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place.

Toxicology

Ecotoxicity Values · 5 items

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 · 3 items

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).

Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and through the skin.
Ecotoxicity Excerpts/AQUATIC SPECIES/ The toxicity was studied in Chlorella emersonii (green alga), Salmo gairdneri and bacteria Cellulomonas and Sporocytophaga myxococcoides. Bis(2-ethylhexyl) phosphate inhibited growth at concn in range 0.3-100 mg/L.
Signs and Symptoms · 3 items

Burning sensation. Cough. Sore throat.

Redness. Burning sensation. Pain. Blisters.

Redness. Pain. Severe burns.

ICSC Environmental DataThe substance is harmful to aquatic organisms.

Regulatory information

TSCA Requirements · 2 items

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.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 · 2 items

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/

Uses & manufacturing

Uses · 6 items

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 · 6 items

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.

Consumer UsesChelating agent
Industry UsesSolvent
Methods of Manufacturing · 2 items

... 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

Formulations/PreparationsGrades or purity: 92+%

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]

Related reactions

16 records

Compound notes

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