化工社化工社 化学情報印刷レポート · 研究参考用
四りん酸ヘキサエチル
エチルテトラホスファート · 四りん酸ヘキサエチル · ヘキサエチル四リン酸 · ジエチル {[({[(ジエトキシホスホリル)オキシ](エトキシ)ホスホリル}オキシ)(エトキシ)ホスホリル]オキシ}ホスホナート · HTP · HET · Ethyl tetraphosphate · RCRA waste number P-062
識別子と物理属性
| CAS No. | 757-58-4 |
|---|---|
| 分子式 | C12H30O13P4 |
| 平均分子量 | 506.25 g/mol |
| 単同位体質量 | 506.063689 g/mol |
| SMILES | CCOP(=O)(OCC)OP(=O)(OCC)OP(=O)(OCC)OP(=O)(OCC)OCC |
| InChIKey | DAJYZXUXDOSMCG-UHFFFAOYSA-N |
| PubChem CID | 12960 |
| EC No. | 212-057-0 |
| DTXSID | DTXSID80862401 |
| 現地名 | 四りん酸ヘキサエチル |
化学・物理的性質
| XLogP | 0 |
|---|---|
| 極性表面積 | 151 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 13 |
| 回転可能結合数 | 18 |
| 重原子数 | 29 |
| 形式電荷 | 0 |
| 複雑度 | 580 |
| 農薬 | Pesticides -> Organophosphate Insecticides |
| 臭い | Odorless |
| 密度 | 1.26 to 1.28 at 25 °C/4 °C1.292 |
| Color/Form | Yellow liquid |
| 溶解度 | Miscible with water and many organic solvents except keroseneVery soluble in ethanol, acetone and benzene |
| 沸点 | 150 °C (decomposes)150°C (rough estimate) |
| Decomposition | When heated to decomposition it emits toxic fumes of /phosphorous oxides/. |
| 融点 | -40 °C-40°C |
| 蒸気圧 | 0.00000002 [mmHg] |
| 屈折率 | Index of refraction = 1.4273 at 27 °C |
| Physical Description | Hexaethyl tetraphosphate is a yellow liquid which is miscible in water. It is difficult to burn. It is toxic by skin absorption and inhalation. It is a mixture of ethyl phosphates and ethyl pyrophosphate. It decomposes at high temperatures. May be found in the form of a dry mixture where the liquid is absorbed onto a dry carrier.Yellow hygroscopic liquid[Hawley] |
| Stability/Shelf Life | Hydrolyzes rapidly in aq soln |
| 外観・状態 | 液体 |
| ヘンリー定数 | 3.0×1011 mol/(m3Pa) at 25℃, HSDB (2015) |
| EPAの化学物質情報 | Hexaethyl tetraphosphate (757-58-4) |
化学的特性
Hexaethyl tetraphosphate is a yellow liquid which is miscible with water and many organic solvents except kerosene; hydrolyzes in low concentration; hygroscopic. decomposes at high temperatures. It is difficult to burn. It is toxic by skin absorption and inhalation. It is a mixture of ethyl phosphates and ethyl pyrophosphate. It decomposes at high temperatures. May be found in the form of a dry mixture where the liquid is absorbed onto a dry carrier.
安全性と法規制
| 規制情報 | 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.) |
|---|---|
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. |
| 健康有害性 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin. |
| 有害性の概要 | Mixture of ethyl phosphates and ethyl pyrophosphatesA cholinesterase inhibitor[Hawley] A strong cholinesterase inhibitorMiosis not accompanied by other symptoms has been reported by pilots of crop dusters and attributed to plane crashes due to lack of depth perception[HSDB] Severely hazardous by all routes of exposureA cholinesterase inhibitor with symptoms including weakness, diarrhea, blurred vision, muscle twitching, and pin-point pupils[EPA OHM/TADS] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs] |
| 輸送番号・ガイド（DOT） | 1611 151 |
| 反応性グループ | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| RCRA 要件 | P062As stipulated in 40 CFR 261.33, when hexaethyltetraphosphate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)). |
| TSCA 要件 | 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. Tetraphosphoric acid, hexaethyl- is included on this list. |
| FIFRA 要件 | /SRP/: No longer registered as a commercial pesticide product. |
| Reactivity Profile | Organophosphates, such as HEXAETHYL TETRAPHOSPHATE, 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. |
| DOT Emergency Guidelines | /GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Hexaethyl tetraphosphateHexaethyl tetraphosphate, liquidHexaethyl tetraphosphate, solid//GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. /Hexaethyl tetraphosphate/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at lease 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Hexaethyl tetraphosphate/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLYit is not effective in spill situations where direct contact with the substance is possible. /Hexaethyl tetraphosphateFor more DOT Emergency Guidelines (Complete) data for HEXAETHYLTETRAPHOSPHATE (8 total), please visit the HSDB record page. |
| 消火 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| 漏出応急措置 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. |
| 応急処置 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:General First Aid: |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA).Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baselineButylcholinesterase activity in serum or plasma = 60% of individual's baselineSample at end of shift[TLVs and BEIs] |
| 消火手順 | If material is on fire or involved in a fire: Extinguish fire using agent suitable for type surrounding fire. Material itself does not burn or burns with difficulty. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Use foam, carbon dioxide, or dry chemical. /Hexaethyl tetraphosphate, liquid/ |
| 非火災時の漏出対応 | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| 処分方法 | [40 CFR 240-280, 300-306, 702-799 (7/1/2005)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P062, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.Potential candidate for rotary kiln incineration with a temperature range of 820 to 1600 °C and residence times for liquids and gasessecondssolids: hours. Also, a potential candidate for fluidized bed incineration range of 450 to 980 °C and residence times for liquids and gases, secondssolids, longer.Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/ |
| Preventive Measures | If material is 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. Attempt to stop leak if without hazard. Use water spray to knock-down vapors. /Hexaethyltetraphosphate, liquid/Personnel protection: Avoid breathing vapors. Keep upwind. Wear self-contained breathing apparatus. Avoid bodily contact with the material. Wear full protective clothing. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Hexaethyltetraphosphate, liquid/Evacuation: If material leaking (not on fire), downwind evacuation must be considered. /Hexaethyltetraphosphate, liquid/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. |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:/Workers/ must be given overalls made of a tight fabric or polyvinyl chloride, gloves and rubber boots. They must wear a respirator with an activated-carbon gas-filter cartridge ... The eyes should be protected by goggles. The signalmen for aerial dusting operations should be equipped with a hat and cape made of polyvinyl chloride or a fabric impregnated with a water repellent. /Organophosphorus pesticides/Wear self-contained breathing apparatus. ... Wear full protective clothing. /Organophosphorus pesticide, liquid, not otherwise specified, (compounds and preparations, agricultural insecticides, not elsewhere classified, liquid)/ |
| Emergency Response Planning Guidelines | Small Fire |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a structure estimation method(2), indicates that hexaethyl tetraphosphate is expected to have very high mobility in soil(SRC). Volatilization of hexaethyl tetraphosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.3X10-17 atm-cu m/mole(SRC), derived using a fragment constant estimation method(3). Hexaethyl tetraphosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-8 mm Hg(SRC), determined from a fragment constant method(4). No biodegradation data for hexaethyl tetraphosphate was located(SRC, 2006)however, biodegradation is expected to be an important environmental fate process because phosphate esters are generally biodegradable in the environment(5). Hydrolysis in moist soils is likely to occur based on a hydrolysis half-life of 7.5 hours at pH 7(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7(SRC), determined from a structure estimation method(2), indicates that hexaethyl tetraphosphate is not 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 3.3X10-17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.39(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation data for hexaethyl tetraphosphate was located(SRC, 2006)however, biodegradation is expected to be an important environmental fate process because phosphate esters are generally biodegradable in the environment(8). A hydrolysis half-life of 7.5 hours at pH 7 indicates that hydrolysis will be an important environmental fate process for hexaethyl tetraphosphate(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexaethyl tetraphosphate, which has an estimated vapor pressure of 2.1X10-8 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 hexaethyl tetraphosphate is removed from the atmosphere by wet and dry deposition(SRC).ATMOSPHERIC & TERRESTRIAL FATE: A PROPERTY OF /ORGANOPHOSPHORUS PESTICIDES/ ... IS THEIR LOW STABILITY IN THE ENVIRONMENT, IE THEIR RELATIVELY RAPID DECAY IN SOIL, WATER, PLANTS. ... /ORGANOPHOSPHORUS PESTICIDES/ |
| 有害作用 | Other Poison - Organophosphate |
| Medical Surveillance | ... Workers ... must undergo an annual medical exam at the beginning of each agricultural season. Contraindications for work with organophosphorus pesticides are organic diseases of the CNS , mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases and circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of the liver & kidneys, eye diseases (chronic conjunctivitis and keratitis). Blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed ... until /cholinesterase level/ is completely restored. /Organophosphorus pesticides/ |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for hexaethyl tetraphosphate can be estimated to be 7(SRC). According to a classification scheme(2), this estimated Koc value suggests that hexaethyl tetraphosphate is expected to have very high mobility in soil(SRC). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ It is a strong inhibitor of cholinesterase, and in contact with eye or absorbed systemically it causes strong miosis and spasm of accommodation./SIGNS AND SYMPTOMS/ Symptomatology: 1. Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... 2. Headache, giddiness, vertigo and weakness. 3. Rhinorrhea and sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis. ... Tearing, ciliary muscle spasm, loss of accommodation and ocular pain... Mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations and twitching of muscles (particularly of tongue and eyelids, and generalized profound weakness. 7. Mental confusion, disorientation and drowsiness. 8. Difficulty in breathing, excessive secretion of saliva and of respiratory tract mucus, oronasal frothing, cyanosis, pulmonary rales and rhonchi and hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, and coma. 10. Death primarily due to respiratory arrest arising from failure of respiratory center, paralysis of respiratory muscles, intense bronchoconstriction or all three. /Parathion//SIGNS AND SYMPTOMS/ Accumulation of acetylcholine in CNS is believed to be responsible for tension, anxiety, restlessness, insomnia, headache, emotional instability, & neurosis, excessive dreaming and nightmares, apathy, and confusion ... described after organophosphate poisoning. /Organophosphate insecticides//SIGNS AND SYMPTOMS/ Organic alkyl phosphate insecticides such as ... hexaethyltetraphosphate (HETP) inhibit cholinesterase. If absorbed through the skin, the victim may show signs of poisoning long after exposure, particularly if contaminated clothes are worn. Uninhibited acetylcholine accumulation causes vomiting, defecation, urination, miosis, asthma and respiratory failure. Crop dusters have noticed miosis without other symptoms and plane accidents have been attributed to failure to correctly judge distance after inhalation by the pilot of the /applied pesticide/./OTHER TOXICITY INFORMATION/ Highly toxic by ingestion, inhalation, and skin absorption. |
| Artificial Pollution Sources | Hexaethyl tetraphosphate's former production and use as a direct contact insecticide(1) may have resulted in its direct release to the environment(SRC). Hexaethyl tetraphosphate is not registered for use in Canada or the United States(2). |
| Environmental Biodegradation | No biodegradation data were located for hexaethyl tetraphosphate(SRC, 2006). Biodegradation in soil and water is expected to be an important environmental fate process because of the presence of phosphate ester functional groups, which generally are biodegradable(1). |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated for hexaethyl tetraphosphate(SRC), using an estimated log Kow of -0.39(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). |
| Volatilization from Water/Soil | The Henry's Law constant for hexaethyl tetraphosphate is estimated as 3.3X10-17 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that hexaethyl tetraphosphate is expected to be essentially nonvolatile from water and moist soil surfaces(2). Hexaethyl tetraphosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-8 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Muscarinic signs of /organophosphorus compounds/ ... consist of hypersalivation, lacrimation, sweating and nasal discharge. Miosis, dyspnea, vomiting, diarrhea and frequency of urination ... Nicotinic effects consist of fasciculation of muscles, weakness and paralysis. Central nervous system effects include nervousness, apprehension, ataxia, convulsions and coma. Death is due to respiratory failure, or sometimes cardiac arrest. There is little difference between signs produced by different ... compounds, but route of absorption may influence one system more than another. /Organophosphorus compounds/ |
| Populations at Special Risk | Work ... must not be carried out by young persons under 18 yr, expectant or nursing mothers, or persons for whom work with toxic chemicals is contraindicated on account of their state of healththe same applies to alcoholics. Contraindications for work with organophosphorus pesticides are organic diseases of the cns, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases and circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of the liver & kidneys, eye diseases (chronic conjunctivitis and keratitis). /Organophosphorus pesticides/ |
| Environmental Abiotic Degradation | The neutral pH first-order hydrolysis rate constant for hexaethyl tetraphosphate was calculated as 0.093 hr-1, which corresponds to a half-life of 7.5 hours at pH 7(1). |
| CERCLA 報告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| DHS Chemicals of Interest (COI) | Hexaethyl tetraphosphateand compressed gasmixtures33.37500Weapons of Mass Effect chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques. |
| 輸送番号（UN） | UN 1611 |
| 毒性 | LD50 oral in rabbit: 21mg/kg |
| 危険等級 | 6.1 |
| 包装等級 | II |
| 有害物質データ | 757-58-4(Hazardous Substances Data) |
用途
使用
Hexaethyl tetraphosphate is used as an insecticide, in particular, the insecticide Bladan. The Germans commonly used this chemical as an insecticide during World War II, when nicotine-based insecticides were not available.
一般的な説明
Tetraethyl pyrophosphate solid is a solid material on which the phosphate itself is absorbed. The phosphate itself is combustible though Hexaethyl tetraphosphate may take effort to ignite. Hexaethyl tetraphosphate is soluble in water and gradually decomposed by it. Hexaethyl tetraphosphate is toxic by inhalation(dust, etc) and by skin absorption.