乙二醇醚及其衍生物

R. Boatman, J. Knaak
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引用次数: 19

摘要

目前,美国有七家醚和其他乙二醇(EG)、二甘醇(DEG)和更高级的乙二醇衍生物制造商。其中五位是美国化学理事会(ACC)乙二醇醚小组的成员。工业上最常见的乙二醇醚是无色液体,有轻微的空灵气味。在合适的催化剂存在下,通过环氧乙烷与无水醇反应,以封闭、连续的工艺生产烷基乙二醇醚。根据反应物的摩尔比和其他工艺参数,得到的产品混合物含有不同数量的单-、二-、三-和更高的乙二醇醚。通常,这些混合物中的产物通过分馏分离和纯化。这些醚与水和许多有机溶剂的可混溶性使它们作为油水组合物的溶剂特别有用。它们相对缓慢的蒸发速度也使它们成为油漆中的溶剂和凝聚剂。其他用途包括油墨、清洁剂、化学中间体、工艺溶剂、制动液和除冰剂。高级醇的醚用作液压油。对美国具有代表性的乙二醇醚的生产和使用进行了估计。1995年西欧乙二醇醚的总产量达24.5万吨。职业性接触乙二醇醚可通过皮肤和吸入发生。在工业接触中,摄入不是一个问题,尽管有一些故意摄入含有乙二醇醚的消费品的案例报道。许多分析方法已经发表,适用于检测环境空气样品中的乙二醇醚。乙二醇醚一般具有低急性、单剂量毒性,LD50值一般为1.0 ~ 4.0 g/kg体重。在动物和人类中,高剂量给药(> 350mg /kg)可导致中枢神经系统抑制,尽管许多研究结果显示对神经组织没有特异性损伤。其他可归因于乙二醇醚的毒理学效应与代谢相应的烷氧乙酸有关。在EGME、EGEE和某些其他乙二醇醚衍生物的情况下,显著的生殖、发育、血液学和免疫效应与甲氧基乙酸(MAA)或乙氧基乙酸(EAA)的形成有关。对于丙基、丁基或更高的同系物取代的其他乙二醇醚衍生物,观察到继发于母体毒性的发育效应(无致畸效应),以及血液学效应。乙二醇醚和乙酸酯可能因生产废水和排放物以及在商业产品中使用而进入环境。关键词:乙二醇醚;分析方法;消除;结构与活性关系;血液的影响;乙酸乙二醇酯;蒸汽
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Ethers of Ethylene Glycol and Derivatives
There are currently seven U.S. manufacturers of ethers and other derivatives of ethylene glycol (EG), diethylene glycol (DEG), and higher glycols. Five of them are members of the American Chemistry Council (ACC) Glycol Ethers' Panel. The glycol ethers most commonly encountered industrially are colorless liquids that have mild ethereal odors. Alkyl glycol ethers are manufactured in a closed, continuous process by reacting ethylene oxide with an anhydrous alcohol in the presence of a suitable catalyst. Depending on the molar ratios of the reactants and other process parameters, the product mixtures obtained contain varying amounts of the monoethylene-, diethylene-, triethylene-, and higher glycol ethers. Typically, the products in these mixtures are separated and purified by fractional distillation. The miscibility of most of these ethers with water and with a large number of organic solvents makes them especially useful as solvents in oil–water compositions. Their relatively slow rate of evaporation also makes them useful as solvents and coalescing agents in paints. Other uses include inks, cleaners, chemical intermediates, process solvents, brake fluids, and deicers. The ethers of the higher glycols are used as hydraulic fluids. An estimate of the U.S. production and use of representative ethylene glycol ethers is presented. Production of ethylene glycol ethers (total) in Western Europe amounted to 245 thousand metric tons in 1995. Occupational exposure to glycol ethers occurs dermally and by inhalation. Ingestion is not a concern in industrial exposure, although some cases of intentional ingestion of consumer products containing ethylene glycol ethers have been reported. A number of analytical methods have been published that are suitable for detecting glycol ethers in environmental air samples. Glycol ethers generally have low acute, single-dose toxicity, and LD50 values generally range from 1.0 to 4.0 g/kg of body weight. In animals and humans, high-dose administrations (>350 mg/kg) result in central nervous system depression, although the results from many studies show no specific damage to neural tissues. Other toxicological effects attributable to glycol ethers are associated with metabolism to the corresponding alkoxyacetic acids. In the case of EGME, EGEE, and certain other glycol ether derivatives, significant reproductive, developmental, hematologic, and immunologic effects have been associated with the formation of either methoxyacetic (MAA) or ethoxyacetic acids (EAA). For other glycol ether derivatives substituted with propyl, butyl, or higher homologues, developmental effects secondary to maternal toxicity (without teratogenic effects), as well as hematologic effects, are observed. Ethylene glycol ethers and acetates may enter the environment from manufacturing effluents and emissions and as a result of their use in commercial products. Keywords: Ethylene glycol ethers; Analytical methods; Elimination; Structure-activity relationship; Hematologic effects; Ethylene glycol acetates; Vapors
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