化工社化工社 化学情報印刷レポート · 研究参考用
りん酸 トリエチル
りん酸 トリエチル · オルトりん酸トリエチル · りん酸トリエチル · りん酸エチル · トリエチル=ホスファート · トリエチルホスフェ-ト · りん酸トリエチル,6N · トリエチルホスフェート
識別子と物理属性
| CAS No. | 78-40-0 |
|---|---|
| 分子式 | C6H15O4P |
| 平均分子量 | 182.15 g/mol |
| 単同位体質量 | 182.07079559 g/mol |
| SMILES | CCOP(=O)(OCC)OCC |
| InChIKey | DQWPFSLDHJDLRL-UHFFFAOYSA-N |
| PubChem CID | 6535 |
| ChEMBL | CHEMBL1236251 |
| ChEBI | CHEBI:45927 |
| EC No. | 201-114-5 |
| DTXSID | DTXSID8026228 |
| 現地名 | りん酸 トリエチル |
化学・物理的性質
| XLogP | 0.8 |
|---|---|
| 極性表面積 | 44.8 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 6 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 113 |
| 物質分類 | Other Classes -> Organophosphates, Other |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| Polymers | Plastics -> PURPlastics -> Flame retardants |
| SpringerMaterials Properties | 31P nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = 0.80 |
| 臭い | MildPleasant smellingマイルドサイダー |
| 密度 | 1.068 (USCG, 1999) - Denser than waterwill sink1.0695 g/cu cm at 20 °CBulk density = 8.90 lb/gal at 20 °C. Combustible.Relative density (water = 1): 1.071.0725 @ 19°C1.072 g/mL at 25 °C (lit.) |
| Flame Retardants | Flame retardantsFlame Retardants -> Organophosphorus flame retardant (OP) |
| Viscosity | 1.46 cSt at 25 °C |
| Color/Form | LiquidColorless, high-boiling liquid |
| 溶解度 | Soluble, slight decomposition (NTP, 1992)Soluble in diethyl ether, benzenevery soluble in ethanolslightly soluble in chloroformSoluble in most organic solvents, alcohol, ether.In water, 5.00X10+5 mg/L at 25 °CSolubility in water: miscible500g/l（遅分解）溶ける |
| 引火点 | 240 °F (NTP, 1992)240 °F (115 °C) (Open cup)116 °C o.c. |
| 融点 | -56 °C |
| 沸点 | 215 °C (lit.) |
| 蒸気密度 | 6.28 (vs air) |
| 蒸気圧 | 1 mm Hg ( 40 °C) |
| 屈折率 | n20/D 1.403(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| 色 | クリア |
| 比重 | 1.072 |
| pH | 7 (H2O, 20℃) |
| 爆発限界 | 1.2-10%(V) |
| Merck | 14,9674 |
| BRN | 1705772 |
| ヘンリー定数 | 2.7×102 mol/(m3Pa) at 25℃, Wolfenden and Williams (1983) |
| 誘電率 | 7.2(20℃) |
| 安定性 | 安定。可燃性。強力な酸化剤、水とは相容れない。 |
| 化粧品成分の機能 | 溶媒 |
| InChI | 1S/C6H15O4P/c1-4-8-11(7,9-5-2)10-6-3/h4-6H2,1-3H3 |
| InChIKey | DQWPFSLDHJDLRL-UHFFFAOYSA-N |
| SMILES | CCOP(=O)(OCC)OCC |
| LogP（分配係数） | 1.11 at 20℃ |
| CAS データベース | 78-40-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Triethyl phosphate(78-40-0) |
| EPAの化学物質情報 | Triethyl phosphate (78-40-0) |
化学的特性
Triethyl Phosphate (TEP) is a colorless, high-boiling liquid and containing 17 wt % phosphorus; mild odor. Very stable at ordinary temperatures, compatible with many gums and resins, soluble in most organic solvents, miscible with water. When mixed with water is quite stable at room temperature, but at elevated temperatures it hydrolyzes slowly. TEP is useful as a solvent in many applications, as a plasticizer for tough, fire-resistant plastics, and as an agricultural chemical as an intermediate in preparing tetraethyl pyrophosphate (TEPP).Like other phosphate esters, Triethyl phosphate damages nerves and is a cholinesterase inhibitor. It is regarded as moderately toxic. Two other alkyl phosphates with toxicities probably similar to that of triethylphosphate are tributylphosphate, (n-C4H9O)3PO, and tris(2-ethylhexyl)-phosphate, (C8H17O)3PO.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Phosphoric acid, triethyl esterPhosphoric acid, triethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphoric acid, triethyl 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: 06-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14738Triethyl phosphate: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Phosphoric acid, triethyl ester: Human health tier I assessment |
| 輸送ラベル（DOT） | Corrosive |
| 火災危険 | Special Hazards of Combustion Products: May produce hazardous decomposition products such as carbon dioxide, carbon monoxide and oxides of phosphorus. (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | Slight when exposed to heat or flame. |
| 健康有害性 | May be harmful by inhalation, ingestion or absorption. May cause irritation. (USCG, 1999) |
| 有害性の概要 | A severe skin, eye, and mucous membrane irritant[CAMEO] The substance is harmful with a narcotic effect and, at high doses, shows certain neurotoxic properties (inhibition of cholinesterase) without indicating delayed neurotoxicity. [eChemPortal: SIDSUNEP] An irritantTargets nerves[MSDSonline] |
| 反応性グループ | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| EC 分類 | Symbol: XnR: 22S: (2)-25 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| TSCA 要件 | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure 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. Phosphoric acid, triethyl ester is included on this list. |
| FIFRA 要件 | Residues of triethyl phosphate are exempted from the requirement of a tolerance when used as a stabilizer for formulations used before crop emerges from soil in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. |
| 消火 | Fire Extinguishing Agents Not to Be Used: Ordinary foam and water may cause frothing.Use powder, alcohol-resistant foam, water spray, carbon dioxide. |
| 応急処置措置 | Fresh air, rest.Rinse skin with plenty of water or shower.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth. Refer for medical attention . |
| 応急処置 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 安全保管 | Separated from strong oxidants and strong bases. Well closed. Ventilation along the floor. |
| 消火手順 | To fight fire, use carbon dioxide, dry chemical, alcohol foam. |
| 保管条件 | In general, materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well-ventilated place, out of direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected... Incompatible materials should be isolated from each other. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 処分方法 | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 漏出処分 | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| 生態毒性値 | LC50 Eisenia foetida /(red wiggler, brandling, or manure worm)/ >1000 mg/kg/14 daysLC50 Leuciscus idus /(Ide)/ 2140 mg/L/48 hr /Conditions of bioassay not specified in source examined/LC50 Daphnia magna /(Water flea)/ 350 mg/L/48 hr /Conditions of bioassay not specified in source examined/LC50 Asellus intermedius (Aquatic sowbug) >100 mg/L/96 hrstatic /formulated product/For more Ecotoxicity Values (Complete) data for TRIETHYL PHOSPHATE (12 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that triethyl phosphate is expected to have high mobility in soil(SRC). Volatilization of triethyl phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.60X10-8 atm-cu m/mole(4). Triethyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.393 mm Hg(5). Triethyl phosphate, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(6) and is therefore not expected to readily biodegrade in the environment.AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that triethyl phosphate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 3.60X10-8 atm-cu m/mole(4). According to a classification scheme(5), measured BCF values ranging from 2.4-22(6) suggests the bioconcentration in aquatic organisms is low(SRC). Triethyl phosphate, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(6) and is therefore not expected to readily biodegrade in aquatic environments.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethyl phosphate, which has a vapor pressure of 0.393 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethyl 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 7.0 hours(SRC), calculated from its rate constant of 5.53X10-11 cu cm/molecule-sec at 25 °C(3). Triethyl phosphate does not absorb light at wavlenghts >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| 有害作用 | Other Poison - Organophosphate |
| 暴露経路 | The substance can be absorbed into the body by ingestion. |
| Average Daily Intake | Air Intake: Insufficient dataWater Intake: (assume 1-20 ug/L in contaminated areas)(1-5) 2-40 ugFood Intake: Insufficient data(SRC). |
| 生態毒性抜粋 | /OTHER TERRESTRIAL SPECIES/ ... Studies were conducted to determine the phytotoxicity of TEP using sorghum-sudangrass (Sorghum bicolor (L.) Moench), tomato (Lycopersicon lycopersicum Mill.), and glossy privet (Ligustrum lucidum Ait.) as test plants grown on Mimbres-Glendale (MG) and Nickel-Tencee (NT) sod associations obtained from White Sands Missile Range. Triethyl phosphate was applied to sod and foliar tissue at rates of 0, 4, 400, and 40 000 mg m-2 sod surface. Triethyl phosphate also was applied in a thickened formulation, as used in missile testing, at an application rate of 40 000 mg m-2 on both soil and foliar tissue. Toxicity was only observed at the highest application rate with pure and thickened TEP. The method of TEP application to soil or foliar tissue did not affect the dry matter weight of tomato or glossy privet growth. There were inconsistent effects of TEP application method on sorghum-sudangrass dry matter weight, depending on soil type. Triethyl phosphate affected the test plants differently with resistance to TEP toxicity increasing in the order: tomato congruent sorghum-sudangrass on NT soil < sorghum-sudangrass on MG soil < glossy privet. A seedling emergence study using sorghum-sudangrass, tomato, and cucumber (Cucumis sativus L.) resulted in similar conclusions from the whole plant studies showing TEP toxicity only at the highest application rate of 40 000 mg m-2. There were indications from sorghum-sudangrass growth and cucumber seedling emergence that TEP toxicity may be less on soil having a higher clay and organic matter content, which may have been due to TEP sorption in soil and decreased TEP bioavailability to plant roots. The absence of phytotoxicity symptoms indicated plants would not be harmed if application rates were at or below 400 mg TEP m-2. |
| Signs and Symptoms | See Ingestion.Redness.Dizziness. Drowsiness. Weakness. Unconsciousness. |
| Effluent Concentrations | Triethyl phosphate was one of a group of six phosphate triesters detected in the leachate from the Osaka North Port Sea-Based Solid Waste Disposal Site in Japan with concentrations ranging from 0.1 to 17.0 ug/L(1). Triethyl phosphate was detected in one of five landfill leachate samples at a concentration of 1-10 ppm collected from five Danish sanitary landfills in February 1983(2). Leachate plumes from two sanitary landfills (Waterloo and North Bay, Ontario) were monitored in 1982 and triethyl phosphate was detected at 10-15 ug/L at the Waterloo site(3). Primary effluent from a wastewater treatment plant was applied to a series of basins on a kame where it was subjected to rapid infiltration treatment(4). Triethyl phosphate was not detected in the initial basin floodwater but was detected at 0.71 ug/L in a down-gradient monitoring well(4). Triethyl phosphate was detected at 0.3 ug/L in a well located in an Oklahoma landfill(5). At unreported concentrations, triethyl phosphate was detected in groundwater from Rocky Mountain Arsenal(6). Triethyl phosphate was detected in 3 samples taken from the leachate in a Swedish municipal landfill(7). Triethyl phosphate was detected in advanced waste treatment concentrates from Lake Tahoe, CA in 1974 and from Blue Plains, Washington DC in 1974(8). |
| Soil Adsorption/Mobility | The Koc of triethyl phosphate is estimated as 65(SRC), using a log Kow of 0.80(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that triethyl phosphate is expected to have high mobility in soil. Leaching through soil may be possible(SRC) as this compound has a very high water solubility of 5.0X10+5 mg/L(4). Triethyl phosphate has been detected in leachates from several landfills(5,6). During rapid infiltration studies, surface water was passed through infiltration terrain consisting of fine-ground dune sand mixed with clay and lens-shaped peat layers. A 70% reduction in the amount of triethyl phosphate initially found in the surface water was found in water which had passed through the dune(7)the loss of triethyl phosphate could be due to biotic and/or abiotic transformations(SRC). In a second rapid infiltration study, triethyl phosphate was detected in a down-gradient monitoring well after primary effluent was placed in basins situated on a kame consisting of poorly graded sands or gravelly sands with interspersed lenses of silty and sandy gravels(8). |
| TSCA Test Submissions | The ability of triethyl phosphate to induce morphological transformation in the BALB/3T3 mouse cell line (Cell Transformation Assay) was evaluated. Based on preliminary toxicity determinations, triethyl phosphate was tested at concentrations of 4, 3, 2.5, 1.5 and 0.3 ul/ml in the complete medium, with cell survival ranging from 97.3% to 12.6%. None of the concentrations tested produced a significant increase in the transformation frequencies (p > 0.10) relative to the complete medium control. |
| Atmospheric Concentrations | URBAN/SUBURBAN: Triethyl phosphate was detected in both Soxhlet extraction and volatile organic analyses as a major component in one of seven carpet samples(1).INDOOR: Indoor air samples taken from new or recently renovated buildings in Switzerland contained a mean triethyl phosphate concentration of 60 ug/cu m(1). Triethyl phosphate was detected in almost all indoor air samples collected from 22 houses (44 rooms) and 11 office buildings (22 offices) in Tokyo, Japan(2).SOURCE DOMINATED: In a laboratory study of vapors (24 liters) emitted from a liquid waste lagoon (uncharacterized), triethyl phosphate was detected(1). |
| Human Toxicity Excerpts | /OTHER TOXICITY INFORMATION/ Some ethyl phosphate derivatives (e.g. parathion) are highly toxic cholinesterase inhibitors. Triethyl phosphate is thought to be weak enzyme inhibitor. |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TC7900000 |
| 毒性 | LD50 orally in Rabbit: 1165 mg/kg |
| 税関コード | 29190090 |
| 危険文句（R） | 22-36 |
| 化審法 | (2)-2000 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xn |
| 安全措置（S） | 25-26 |
| 自然発火温度 | 845 °F |
| 危険等級 | Acute Tox. 4 OralEye Irrit. 2 |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 78-40-0(Hazardous Substances Data) |
| 危険度評価（NFPA 704基準/消防庁データ） | 火災[赤]=1 |
用途
解説
リン酸のエステルであるリン酸トリエチルは無色の液体(沸点216～217℃)で，ニトロセルロースや酢酸セルロースの溶剤として用いられたり，ゴムや合成樹脂の可塑剤として用いられる。また，リン酸エステルは生体内で多く見いだされ，生命現象に重要な役割を果たしている。株式会社平凡社 世界大百科事典 第２版について | 情報
用途
ニトロセルロースなどの溶媒、樹脂安定剤、触媒などに使用 (有機化合物辞典 (1985))
使用
Triethyl phosphate is use as a flame retardant in the manufacture of polyisocyanurate (PIR) and polyurethane (PUR) foam insulation and thermoset plastic products. The chemical compound is also used as a viscosity reducer in plastic resins, and as a catalyst, solvent or intermediate in the production of pesticides, pharmaceuticals, lacquers and other products.As ethylating agent; formation of polyesters which are used as insecticides.
一般的な説明
Triethyl phosphate [78-40-0] is a colorless, corrosive liquid. Combustible. Slowly dissolves in water and sinks in water. Severely irritates skin, eyes and mucous membranes. It is manufactured from diethyl ether and phosphorus pentoxide via a metaphosphate intermediate. Triethyl phosphate has been used commercially as an additive for polyester laminates and in cellulosics. In polyester resins it functions as a viscosity depressant and as a flame retardant. The viscosity-depressant effect of triethyl phosphate in polyester resin permits high loadings of alumina trihydrate,a fire-retardant smoke-suppressant filler. Triethyl phosphate has also been employed as a flame-resistant plasticizer in cellulose acetate.Because of its water solubility the use of triethyl phosphate is limited to situations where weathering resistance is unimportant.The halogenated alkyl phosphates are generally used for applications where lower volatility and greater resistance to leaching are required.
製法・合成法
調製方法
Triethyl phosphate is manufactured from diethyl ether and phosphorus pentoxide via a metaphosphate intermediate.Prepared by the reaction of tetraethyl hypophosphate with ethanol in the presence of aluminum ethoxide or by treating triethyl phosphate with diethyl hydrogen phosphate.