单羧酸和烯基羧酸酯以及单醇和多醇酯

K. Coleman, W. A. Toscano
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This chapter (Chapter 57) reviews \n \n \n \nesters of monocarboxylic acids and mono- and polyalcohols and \n \n \n \n \nesters of alkenyl carboxylic acids and monoalcohols; Chapter 58 reviews \n \n \n \n \nesters of aromatic monocarboxylic acids and monoalcohols, \n \n \n \n \nesters of monocarboxylic acids and di-, tri-, and polyalcohols, \n \n \n \n \ndicarboxylic acid esters, \n \n \n \n \nalkenyl dicarboxylic esters, \n \n \n \n \nesters of aromatic diacids, and \n \n \n \n \ntricarboxylic acid esters; and Chapter 59 covers \n \n \n \n \nesters of carbonic acid and orthocarbonic acid, \n \n \n \n \nesters of organic phosphorous compounds, \n \n \n \n \nesters of monocarboxylic halogenated acids, alkanols, or haloalcohols, and \n \n \n \n \norganic silicon esters. \n \n \n \n \n \n \nThe sequence of the compounds has been organized according to the chemical structure of the major functional metabolites. This involves the ester hydrolyzates, primarily the acid and secondarily the alcohol. The reason for this sequence was the general observation that the degree of toxic effect, in addition to that of the original material, more often was the result of the toxicity of the acid rather than the response of the alcohol. \n \n \n \nEsters are important from an industrial hygiene perspective since exposure can occur during the process of manufacturing esters, the process of manufacturing materials containing or composed of esters, handling and use of products containing or composed of esters, and treatment of wastes containing esters. In turn, exposure to esters is important from a toxicological perspective because of the correlated observations of adverse physiological responses exhibited by laboratory animals and humans. \n \n \n \nOverviews of the physical, chemical, and toxicological (i.e., physiological responses) properties of many subclasses of esters and/or of specific compounds are provided. In addition, summaries of relative manufacturing and use information are included for many compounds. \n \n \n \nChemically, esters are organic compounds commonly formed via the combination of an acid, typically an organic (COOH) mono- or polyacid, and a hydroxyl (OH) group of a mono- or polyalcohol or phenol; water (HOH) is generated as a by-product of the reaction. \n \n \n \nThe esters are widely used in industry and commerce. They can be prepared by the reactions of acids with alcohols by reacting metal salts of acids with alkyl halides, acid halides with alcohols, or acid anhydrides with alcohols by the interchange of radicals between esters. Most esters exist in liquid form at ambient temperatures, but some possess lower boiling points than their original starting materials. They are relatively water insoluble, except for the lower molecular weight members. Their flash points are in the flammable range. The monocarboxylic acid esters have high volatility and pleasant odors, whereas the di- and polyacid esters are relatively nonvolatile and exhibit essentially no odor. The monocarboxylic esters occur frequently in natural products, as, for example, in fruits, to which they lend their pleasant odor and taste. Because of the different properties of esters from the original acids and alcohols, esterification can be used for their isolation or for chemically protecting specific carboxy or hydroxy functions. \n \n \n \nAbsorbed esters and/or metabolites derived from biotransformed esters can initiate toxic effects in some mammalian systems, including humans, and cause adverse physiological responses. Indeed, the underlying causes of physiological responses are due to initial interactions biochemically within a system. Within these chapters, a summary of reviewed literature will reveal that, in general, toxic effects associated with exposure to various esters include primary irritation to ocular, upper and lower respiratory, and dermal systems; depression of the central nervous system (CNS) (e.g., anesthesia and narcosis); dermal hypersensitization; impact to the gastrointestinal, hepatic, and renal systems; abnormal cardiac rhythm; and carcinogenesis. Indeed, these and some additional effects are based predominantly on rodent studies. A review of the literature reported here, however, indicates that the most commonly reported effects in animals and humans are irritation and, to some extent, CNS depression. Data are reported in this chapter for several classes of esters, including formates, acetates, acrylates and methacrylates, propionates, and lactates. \n \n \n \nMost of the aliphatic esters possess some degree of irritation on exposed surfaces. \n \n \n \nPractically all the common aliphatic and aromatic esters, except for some phosphates used as plasticizers, are inert. At the most, minor degrees of irritation may follow inhalation of heated vapors or prolonged skin exposure. Some of the literature also suggests that reported skin sensitization appears more likely in the presence of impurities or side products. Many of the materials are so inert that any LD50 value is impractical to determine. Specific pathology is usually absent even when the materials are fed in massive quantities to the point of nutritional deprivation. Oily or watery excretion products, sometimes observed at high feeding levels, indicate lack of absorption. The apparent nontoxicity may also be a sign of rapid hydrolysis, metabolism, and excretion. The resins are completely inert, unabsorbed in the gastrointestinal tract, and nonirritant at the surface of the skin and pulmonary system. \n \n \nKeywords: \n \nacetates; \nacetoacetals; \nacrylates; \nalkyl carboxylic acids; \nbutyrates; \nformates; \ninhalation; \nlactates; \nmethacrylates; \npropionates; \nsugarcane","PeriodicalId":19820,"journal":{"name":"Patty's Toxicology","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2012-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"7","resultStr":"{\"title\":\"Esters of Mono‐ and Alkenyl Carboxylic Acids and Mono‐ and Polyalcohols\",\"authors\":\"K. Coleman, W. A. Toscano\",\"doi\":\"10.1002/0471435139.TOX079.PUB2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"This volume contains three chapters reviewing 12 classes of organic compounds called esters. 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This involves the ester hydrolyzates, primarily the acid and secondarily the alcohol. The reason for this sequence was the general observation that the degree of toxic effect, in addition to that of the original material, more often was the result of the toxicity of the acid rather than the response of the alcohol. \\n \\n \\n \\nEsters are important from an industrial hygiene perspective since exposure can occur during the process of manufacturing esters, the process of manufacturing materials containing or composed of esters, handling and use of products containing or composed of esters, and treatment of wastes containing esters. 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引用次数: 7

摘要

本卷包含三章回顾12类有机化合物称为酯。本章(第57章)回顾了单羧酸酯、单醇和多醇酯以及烯基羧酸酯和单醇酯;第58章综述了芳香单羧酸酯类和单醇类、单羧酸酯类和二、三、多醇类、二羧酸酯类、烯基二羧酸酯类、芳香二酸酯类和三羧酸酯类;第59章涵盖了碳酸酯和正碳酸酯、有机磷化合物酯、单羧基卤代酸酯、烷醇或卤代醇酯和有机硅酯。这些化合物的序列是根据主要功能代谢物的化学结构来组织的。这涉及酯水解物,首先是酸,其次是醇。这种顺序的原因是一般观察到,除了原始物质的毒性作用外,毒性作用的程度更多地是酸的毒性的结果,而不是酒精的反应。从工业卫生的角度来看,酯类很重要,因为暴露可能发生在制造酯类、制造含有或由酯类组成的材料、处理和使用含有或由酯类组成的产品以及处理含有酯类的废物的过程中。反过来,从毒理学的角度来看,暴露于酯类是很重要的,因为实验动物和人类都表现出了相关的不良生理反应。概述了许多亚类酯和/或特定化合物的物理、化学和毒理学(即生理反应)特性。此外,还包括许多化合物的相关生产和使用信息的摘要。从化学上讲,酯是一种有机化合物,通常是由酸(通常是有机的(COOH)单酸或聚酸)和单醇或多醇或苯酚的羟基(OH)组合而成;水(HOH)是反应的副产物。酯类化合物广泛应用于工业和商业。它们可以由酸与醇的反应制备,通过酸的金属盐与烷基卤化物反应,酸卤化物与醇反应,或酸酸酐与醇反应,通过酯之间的自由基交换。大多数酯在环境温度下以液体形式存在,但有些酯的沸点低于其原始起始物质。除了分子量较低的分子外,它们相对不溶于水。它们的闪点在易燃范围内。单羧酸酯具有高挥发性和令人愉快的气味,而二酸酯和多酸酯相对不挥发,基本上没有气味。单羧酸酯经常出现在天然产物中,例如水果中,它们具有令人愉快的气味和味道。由于酯与原始酸和醇的性质不同,酯化反应可用于分离它们或化学保护特定的羧基或羟基功能。吸收的酯类和/或生物转化酯衍生的代谢物可在包括人类在内的一些哺乳动物系统中引发毒性作用,并引起不良的生理反应。事实上,生理反应的根本原因是由于系统内初始的生物化学相互作用。在这些章节中,综述文献将揭示,一般来说,与暴露于各种酯相关的毒性作用包括对眼部、上、下呼吸和皮肤系统的主要刺激;中枢神经系统(CNS)的抑制(如麻醉和麻醉);真皮hypersensitization;对胃肠道、肝脏和肾脏系统的影响;心律失常;和致癌作用。事实上,这些和一些额外的影响主要是基于啮齿动物的研究。然而,对文献的回顾表明,在动物和人类中最常见的影响是刺激,在某种程度上,中枢神经系统抑郁。本章报告了几种酯类的数据,包括甲酸酯、乙酸酯、丙烯酸酯和甲基丙烯酸酯、丙酸酯和乳酸酯。大多数脂肪族酯对暴露的表面具有一定程度的刺激性。除了一些用作增塑剂的磷酸盐外,几乎所有常见的脂肪族和芳香族酯都是惰性的。在最多的情况下,轻微的刺激可能会随着吸入加热蒸汽或长时间的皮肤暴露。一些文献还表明,报告的皮肤致敏更可能出现在杂质或副产品的存在下。许多材料是惰性的,以致于任何LD50值都无法确定。 即使大量喂食到营养剥夺的程度,通常也不会出现特定的病理现象。在高摄食水平时,有时观察到油状或水样的排泄物,表明缺乏吸收。明显的无毒性也可能是水解、代谢和排泄迅速的标志。树脂是完全惰性的,在胃肠道中不被吸收,在皮肤和肺系统表面无刺激性。关键词:醋酸纤维素;acetoacetals;丙烯酸酯;烷基羧酸;丁酸;整合;吸入;乳酸;丙烯酸甲酯;类;甘蔗
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Esters of Mono‐ and Alkenyl Carboxylic Acids and Mono‐ and Polyalcohols
This volume contains three chapters reviewing 12 classes of organic compounds called esters. This chapter (Chapter 57) reviews esters of monocarboxylic acids and mono- and polyalcohols and esters of alkenyl carboxylic acids and monoalcohols; Chapter 58 reviews esters of aromatic monocarboxylic acids and monoalcohols, esters of monocarboxylic acids and di-, tri-, and polyalcohols, dicarboxylic acid esters, alkenyl dicarboxylic esters, esters of aromatic diacids, and tricarboxylic acid esters; and Chapter 59 covers esters of carbonic acid and orthocarbonic acid, esters of organic phosphorous compounds, esters of monocarboxylic halogenated acids, alkanols, or haloalcohols, and organic silicon esters. The sequence of the compounds has been organized according to the chemical structure of the major functional metabolites. This involves the ester hydrolyzates, primarily the acid and secondarily the alcohol. The reason for this sequence was the general observation that the degree of toxic effect, in addition to that of the original material, more often was the result of the toxicity of the acid rather than the response of the alcohol. Esters are important from an industrial hygiene perspective since exposure can occur during the process of manufacturing esters, the process of manufacturing materials containing or composed of esters, handling and use of products containing or composed of esters, and treatment of wastes containing esters. In turn, exposure to esters is important from a toxicological perspective because of the correlated observations of adverse physiological responses exhibited by laboratory animals and humans. Overviews of the physical, chemical, and toxicological (i.e., physiological responses) properties of many subclasses of esters and/or of specific compounds are provided. In addition, summaries of relative manufacturing and use information are included for many compounds. Chemically, esters are organic compounds commonly formed via the combination of an acid, typically an organic (COOH) mono- or polyacid, and a hydroxyl (OH) group of a mono- or polyalcohol or phenol; water (HOH) is generated as a by-product of the reaction. The esters are widely used in industry and commerce. They can be prepared by the reactions of acids with alcohols by reacting metal salts of acids with alkyl halides, acid halides with alcohols, or acid anhydrides with alcohols by the interchange of radicals between esters. Most esters exist in liquid form at ambient temperatures, but some possess lower boiling points than their original starting materials. They are relatively water insoluble, except for the lower molecular weight members. Their flash points are in the flammable range. The monocarboxylic acid esters have high volatility and pleasant odors, whereas the di- and polyacid esters are relatively nonvolatile and exhibit essentially no odor. The monocarboxylic esters occur frequently in natural products, as, for example, in fruits, to which they lend their pleasant odor and taste. Because of the different properties of esters from the original acids and alcohols, esterification can be used for their isolation or for chemically protecting specific carboxy or hydroxy functions. Absorbed esters and/or metabolites derived from biotransformed esters can initiate toxic effects in some mammalian systems, including humans, and cause adverse physiological responses. Indeed, the underlying causes of physiological responses are due to initial interactions biochemically within a system. Within these chapters, a summary of reviewed literature will reveal that, in general, toxic effects associated with exposure to various esters include primary irritation to ocular, upper and lower respiratory, and dermal systems; depression of the central nervous system (CNS) (e.g., anesthesia and narcosis); dermal hypersensitization; impact to the gastrointestinal, hepatic, and renal systems; abnormal cardiac rhythm; and carcinogenesis. Indeed, these and some additional effects are based predominantly on rodent studies. A review of the literature reported here, however, indicates that the most commonly reported effects in animals and humans are irritation and, to some extent, CNS depression. Data are reported in this chapter for several classes of esters, including formates, acetates, acrylates and methacrylates, propionates, and lactates. Most of the aliphatic esters possess some degree of irritation on exposed surfaces. Practically all the common aliphatic and aromatic esters, except for some phosphates used as plasticizers, are inert. At the most, minor degrees of irritation may follow inhalation of heated vapors or prolonged skin exposure. Some of the literature also suggests that reported skin sensitization appears more likely in the presence of impurities or side products. Many of the materials are so inert that any LD50 value is impractical to determine. Specific pathology is usually absent even when the materials are fed in massive quantities to the point of nutritional deprivation. Oily or watery excretion products, sometimes observed at high feeding levels, indicate lack of absorption. The apparent nontoxicity may also be a sign of rapid hydrolysis, metabolism, and excretion. The resins are completely inert, unabsorbed in the gastrointestinal tract, and nonirritant at the surface of the skin and pulmonary system. Keywords: acetates; acetoacetals; acrylates; alkyl carboxylic acids; butyrates; formates; inhalation; lactates; methacrylates; propionates; sugarcane
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