化工社化工社 化学情報印刷レポート · 研究参考用
トリメチロールエタン
トリメチロールエタン · 2,2-ビス(ヒドロキシメチル)プロパン-1-オール · 1,1,1-トリメチロールエタン · 2-メチル-2-(ヒドロキシメチル)-1,3-プロパンジオール · エチリジントリメタノール · 2-(ヒドロキシメチル)-2-メチルプロパン-1,3-ジオール · 1,1,1-エタントリイルトリス(メタノール) · 1,1,1-エタントリメタノール
識別子と物理属性
| CAS No. | 77-85-0 |
|---|---|
| 分子式 | C5H12O3 |
| 平均分子量 | 120.15 g/mol |
| 単同位体質量 | 120.07864424 g/mol |
| SMILES | CC(CO)(CO)CO |
| InChIKey | QXJQHYBHAIHNGG-UHFFFAOYSA-N |
| PubChem CID | 6502 |
| EC No. | 201-063-9 |
| DTXSID | DTXSID2026444 |
| 現地名 | トリメチロールエタン |
化学・物理的性質
| XLogP | -1.2 |
|---|---|
| 極性表面積 | 60.7 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 3 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 50.4 |
| Polymers | Other Classes -> Alcohols and Polyols, Other |
| SpringerMaterials Properties | Density |
| 密度 | 1.210 g/cu cm at 20 °C1.0456 (rough estimate) |
| Color/Form | White powder or needles from alcoholColorless crystals |
| 溶解度 | Miscible in water and ethanolinsoluble in diethyl ether and benzenevery soluble in acetic acidSoluble in water and ethanolIn water, 140 g per 100 g at 25 °C溶ける |
| 沸点 | 283 °CBP: 137 °C at 15 mm Hg137°C 15mm |
| 融点 | 204 °C193-195 °C(lit.) |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Dry PowderColorless or white solid[HSDB] |
| Other Experimental Properties | Hygroscopic |
| 屈折率 | 1.4056 (estimate) |
| 引火点 | 160°C |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| pKa（酸解離定数） | 14.03±0.10(Predicted) |
| 外観・状態 | 結晶性粉末、結晶、および/またはチャンク |
| 色 | 白い |
| BRN | 1304452 |
| ヘンリー定数 | 9.0×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C5H12O3/c1-5(2-6,3-7)4-8/h6-8H,2-4H2,1H3 |
| InChIKey | QXJQHYBHAIHNGG-UHFFFAOYSA-N |
| SMILES | CC(CO)(CO)CO |
| CAS データベース | 77-85-0(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,3-Propanediol, 2-(hydroxymethyl)-2-methyl-(77-85-0) |
| EPAの化学物質情報 | 1,3-Propanediol, 2-(hydroxymethyl)-2-methyl- (77-85-0) |
化学的特性
white crystalline powder, crystals and/or chunks
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 90.6% (145 of 160) of all reports.Not ClassifiedAggregated GHS information provided per 160 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: 1,3-Propanediol, 2-(hydroxymethyl)-2-methyl-1,3-Propanediol, 2-(hydroxymethyl)-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2-(hydroxymethyl)-2-methyl- 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: 24-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/223811,3-Propanediol, 2-(hydroxymethyl)-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard |
| 火災の可能性 | Combustible |
| 有害性の概要 | An irritant[MSDSonline] |
| Hazard Classes and Categories | Not Classified |
| 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. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of less than 1(SRC), determined from a structure estimation method(2), indicates that 1,1,1-tris(hydroxymethyl)ethane is expected to have very high mobility in soil(SRC). Volatilization of 1,1,1-tris(hydroxymethyl)ethane from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,1,1-Tris(hydroxymethyl)ethane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-6 mm Hg(SRC), determined from a fragment constant method(4). 1,1,1-Tris(hydroxymethyl)ethane, present at 100 mg/L, reached 4 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(5), suggesting that biodegradation in soil is not an important environmental fate process(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of less than 1(SRC), determined from a structure estimation method(2), indicates that 1,1,1-tris(hydroxymethyl)ethane 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 1.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). 1,1,1-Tris(hydroxymethyl)ethane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -0.30(6)and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. 1,1,1-Tris(hydroxymethyl)ethane, present at 100 mg/L, reached 4 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(8), suggesting that biodegradation in water is not an important environmental fate process(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1,1-tris(hydroxymethyl)ethane, which has an estimated vapor pressure of 1.7X10-6 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 1,1,1-tris(hydroxymethyl)ethane 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 30 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,1,1-tris(hydroxymethyl)ethane may be removed from the air by wet or dry deposition(SRC). 1,1,1-Tris(hydroxymethyl)ethane does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,1,1-tris(hydroxymethyl)ethane can be estimated to be less than 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,1,1-tris(hydroxymethyl)ethane is expected to have very high mobility in soil. |
| Artificial Pollution Sources | 1,1,1-Tris(hydroxymethyl)ethane's production and use in the manufacture of varnishes, alkyd and polyester resins, as a conditioning agent and synthetic drying oils(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: 1,1,1-Tris(hydroxymethyl)ethane, present at 100 mg/L, reached 4 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). In a study using gas chromatography to monitor substrate disappearance, 1,1,1-tris(hydroxymethyl)ethane, at an initial concentration of 50 ppm, did not biodegrade under aerobic conditions(2).ANAEROBIC: In a study using gas chromatography to monitor substrate disappearance, 1,1,1-tris(hydroxymethyl)ethane, at an initial concentration of 50 ppm, did not biodegrade under anaerobic conditions(1). |
| Environmental Bioconcentration | An estimated BCF of 3.2 was calculated for 1,1,1-tris(hydroxymethyl)ethane(SRC), using an estimated log Kow of -0.30(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 1,1,1-tris(hydroxymethyl)ethane is estimated as 1.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,1,1-tris(hydroxymethyl)ethane is expected to be essentially nonvolatile from water surfaces(2). 1,1,1-Tris(hydroxymethyl)ethane's Henry's Law constant indicates that volatilization from moist soil surfaces is unlikely to occur(SRC). 1,1,1-Tris(hydroxymethyl)ethane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-6 mm Hg(SRC), determined from a fragment constant method(3). |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 1,1,1-tris(hydroxymethyl)ethane with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 30 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1,1,1-Tris(hydroxymethyl)ethane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 1,1,1-Tris(hydroxymethyl)ethane does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 1090 workers were potentially exposed to 1,1,1-tris(hydroxymethyl)ethane in the US(1). Occupational exposure to 1,1,1-tris(hydroxymethyl)ethane may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used(SRC). |
| Environmental Fate/Exposure Summary | 1,1,1-Tris(hydroxymethyl)ethane's production and use in the manufacture of varnishes, alkyd and polyester resins, as a conditioning agent and synthetic drying oils may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.7X10-6 mm Hg at 25 °C indicates 1,1,1-tris(hydroxymethyl)ethane will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase 1,1,1-tris(hydroxymethyl)ethane will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 30 hours. Particulate-phase 1,1,1-tris(hydroxymethyl)ethane will be removed from the atmosphere by wet or dry deposition. 1,1,1-Tris(hydroxymethyl)ethane does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, 1,1,1-tris(hydroxymethyl)ethane is expected to have very high mobility based upon an estimated Koc of less than 1. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.1X10-8 atm-cu m/mole. 1,1,1-Tris(hydroxymethyl)ethane is unlikely to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, 1,1,1-tris(hydroxymethyl)ethane is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. 1,1,1-Tris(hydroxymethyl)ethane, present at 100 mg/L, reached 4 percent of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test, suggesting that biodegradation is not an important environmental fate process. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 1,1,1-tris(hydroxymethyl)ethane may occur through inhalation and dermal contact with this compound at workplaces where 1,1,1-tris(hydroxymethyl)ethane is produced or used. (SRC) |
| Antidote and Emergency Treatment | /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/ |
| F | 3 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TY7137500 |
| 税関コード | 29054910 |
| 化審法 | (2)-243 |
| 安全措置（S） | 22-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 77-85-0(Hazardous Substances Data) |
用途
使用
1,1,1-Tris(hydroxymethyl)ethane is an intermediate in the production of alkyd and polyester resins, powder coating resins, synthetic lubricants based on polyol esters, stabilizers for plastics, plasticizers, and pigment coatings. It is used in some phase change materials.
製法・合成法
調製方法
1,1,1-Tris(hydroxymethyl)ethane (2-hydroxymethyl-2-methyl-1,3-propanediol) is made by aldol condensation of propionaldehyde with formaldehyde, followed by reaction of the intermediate 2,2-bis(hydroxymethyl)propanal with excess formaldehyde in the presence of sodium hydroxide or lime as basic component. The resulting aqueous solution is freed from excess formaldehyde by distillation under pressure and further concentrated. The formate byproduct can be separated by extracting the trimethylolethane from the residue with organic solvents such as 2-propanol or by almost complete removal of the water and dissolving the trimethylolethane in acetone or methanol.
純化方法
Dissolve it in hot tetrahydrofuran, filter and precipitate it with hexane. It has also been crystallised from acetone/water (1:1). Dry it in a vacuum. [Beilstein 1 H 520, 1 IV 2780.]