壬基酚聚氧乙烯醚 | 20427-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 壬基酚聚氧乙烯醚
• 中文别名: 壬基酚二乙氧基酯；壬基酚二乙氧基酯(4-N-NP2EO)；壬基酚聚氧乙烯醚(4-N-NP2EO)
• 英文名称: nonoxynol-9
• 英文别名: 4-n-nonylphenol diethoxylate；4-nonylphenol-di-ethoxylate；4-Nonylphenol diethoxylate；4-nonylphenoldiethoxylate；Nonylphenol diethoxylate；Igepal CO-210；2-[2-(4-Nonylphenoxy)ethoxy]ethanol
• CAS: 20427-84-3
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: BLXVTZPGEOGTGG-UHFFFAOYSA-N

物化性质

• 沸点：
  408.84°C (rough estimate)
• 密度：
  0.9987 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）
• 物理描述：
  Ethoxylated nonylphenol appears as colorless liquid or white solid with a mild odor. May float or sink in water. A low molecular-weight polymer. Used as a non-ionic surfactant, as an emulsifier, or as a metal cleaner, depending on the degree of polymerization.
• 熔点：
  42-43 °C
• 闪点：
  greater than 140 °F (burns with difficulty) (USCG, 1999)
• 分解：
  When heated to decomposition it emits acrid smoke and fumes.

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

毒理性

• 毒性数据

LCLo（大鼠）= 29 毫克/立方米/8小时

LCLo (rat) = 29 mg/m3/8h

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止窒息。保持患者安静，维持正常体温。寻求医疗救助。 /乙二醇、甘油醇及相关化合物/

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Ethylene glycol, glycols, and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在转运过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……。/乙二醇、甘油和相关化合物/

/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 necessary. 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. Administer activated charcoal ... . /Ethylene glycol, glycols, and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）乳酸钠林格液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。如果病人在正常液体量时仍低血压，考虑使用血管加压药。注意液体过载的迹象……。用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/乙二醇、甘油和其他相关化合物/

/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 ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/研究了表面活性剂（单次剂量为50或100 mg/kg）对金属硫蛋白、血红素和血红蛋白含量以及雄性Wistar大鼠肝脏中的血红素加氧酶和药物代谢酶活性的影响，这些大鼠事先用苯巴比妥或β-萘黄酮进行了预处理。测试的表面活性剂包括十二烷基硫酸钠、十二烷基苯磺酸钠和Emulgen-913。注射表面活性剂后，金属硫蛋白含量显著增加。仅苯巴比妥减少了Emulgen-913诱导的金属硫蛋白中锌含量的增加，但对NADPH-细胞色素c-还原酶或DT-二氢酶的活性没有产生显著影响。这些发现表明苯巴比妥增强了体内Emulgen-913的代谢，并可能因此减少肝脏中表面活性剂或其代谢物的含量。仅β-萘黄酮显著增加了DT-二氢酶的活性和金属硫蛋白的含量，但它降低了NADPH-细胞色素c-还原酶的活性。β-萘黄酮引起的金属硫蛋白含量或DT-二氢酶活性的增加被Emulgen-913进一步增强，而NADPH-细胞色素c-还原酶受到抑制。苯巴比妥预处理没有阻止Emulgen-913引起的血红素加氧酶活性的增加，但β-萘黄酮预处理轻微抑制了对Emulgen-913的反应。细胞色素p-450通过苯巴比妥或β-萘黄酮治疗显著增加，但这些增加随后被注射表面活性剂显著抑制。

/LABORATORY ANIMALS: Acute Exposure/ The effects of surfactants (single dose of 50 or 100 mg/kg) were studied on the contents of metallothionein, heme and hemoproteins and on the activities of heme oxygenase and drug metabolizing enzymes in the liver of male Wistar rats pretreated with phenobarbital or beta-naphthoflavone. Surfactants tested included sodium dodecylsulfate, sodium-n-dodecylbenzenesulfonate and Emulgen-913. Metallothionein content was remarkably increased after the injection of surfactants. Phenobarbital alone decreased the Emulgen-913 induced elevation in the contents of zinc of metallothionein, but did not exert any significant effects on the activities of NADPH-cytochrome-c-reductase or DT-diaphorase. These findings suggest that phenobarbital enhances Emulgen-913 metabolism in vivo, and consequently might reduce the contents of surfactant or its metabolites in the liver. Beta-naphthoflavone alone markedly increased the activity of DT-diaphorase and the content of metallothionein but it decreased the activity of NADPH-cytochrome-c-reductase. The increased metallothionein content or DT-diaphorase activity caused by beta-naphthoflavone were further enhanced by Emulgen-913, while NADPH cytochrome-c-reductase was depressed. Phenobarbital pretreatment did not prevent the increase in heme oxygenase activity caused by Emulgen-913, but beta-naphthoflavone pretreatment slightly inhibited the response to Emulgen-913. Cytochrome p-450 was markedly increased by treatment with phenobarbital or beta-naphthoflavone, but these increases were remarkably depressed by subsequent injection of surfactant.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  2,4-二羟二苯甲酮 、 1-氯辛烷 、 disodium;carbonate 、 碘化钾 、 壬基酚聚氧乙烯醚 在 1-氯辛烷 、 水 、 cloudy yellow liquid 、 丙酮 、 Sodium sulfate-III 、 Hg 、 甲醇 作用下， 以 水 为溶剂， 反应 2.33h， 生成 2-羟基-4-正辛氧基二苯甲酮
  参考文献：
  名称：

  Partial alkylation of polyhydroxybenzophenones

  摘要：

  在非水溶剂的存在下，即聚乙二醇或其单烷基或双烷基衍生物中，部分烷基化具有邻-和对-羟基取代基的多羟基苯并酮，以形成邻-羟基，对-烷氧基苯并酮的反应进行，从而在较短的反应时间内获得高产率的烷基化产物。

  公开号：

  US04323710A1
• 作为产物：
  描述：

  2-(2-氯乙氧基)乙酸乙酯 、 对壬基酚 在 sodium methylate 作用下， 以 丙酮 为溶剂， 生成 壬基酚聚氧乙烯醚
  参考文献：
  名称：

  Metabolic fate of 2,4-dichloroaniline, prochloraz and nonylphenol diethoxylate in rainbow trout: a comparative in vivo/in vitro approach

  摘要：

  The metabolism and distribution of 2,4-dichloroaniline (2,4-DCA), prochloraz and 4-n-nonylphenol diethoxylate (NP2EO) were investigated in vivo and in vitro in rainbow trout (Oncorhynchus mykiss). Each compound was administered p.o. (10 mg/kg wet weight) and urine was collected during 48 h (2,4-DCA, prochloraz) or 72 h (NP2EO). Fish were sacrificed, the gall bladder was excised and radioactivity was measured in tissues, viscera and carcasses. Metabolic profiles were performed by radio-HPLC and when possible metabolites were identified by LC/MS. For comparison, the biotransformation of these xenobiotics was also investigated in freshly isolated hepatocytes. The metabolic pathways of 2,4-DCA have been identified leading to the glucuronide conjugate (in vivo) and to the glucuronide conjugate and the hydroxylamine metabolite (in vitro). This difference highlights the usefulness of the hepatocyte system in metabolic studies, since the formation of the hydroxylamine reactive metabolite cannot be demonstrated in vivo. For prochloraz, we observed that residue levels are significantly higher in males than in females for gill, fat, brain and carcasses, however, the reasons for this difference remain unclear. Although, the presence of glucuronide conjugates was detected in vivo and in vitro, the chemical structure of isolated metabolites has to be determined. However, the comparison of the in vivo versus in vitro metabolic profiles indicates that several peaks, probably corresponding to intermediate metabolites, were present only in hepatocyte incubations. Biotransformation of NP2EO occurred in vivo and in vitro in rainbow trout, but did not result in the formation of 4-n-NP. The major metabolite present in bile corresponded to the NP2EO-glucuronide but this metabolite was not found in vitro. It is concluded that hepatocytes may produce a different metabolic pattern than in the whole fish, but may also give evidence of a metabolic pathway difficult to apprehend in vivo. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0166-445x(01)00163-1

文献信息

• 1,1-DI[(ALKYLPHENOXY)ETHOXY]CYCLOHEXANES
  申请人：Bonham James A.

  公开号：US20130197274A1

  公开（公告）日：2013-08-01

  Disclosed is a ketal having the formula: wherein R′ and R″ independently are an alkyl group having from 8 to about 20 carbon atoms; m and n independently are an integer of from 1 to about 200; and r and s independently are an integer of from 1 to 3; and the method for preparing the ketal by transketalization using 1,1-dimethoxycyclohexane or 1,1-diethoxycyclohexane with an (alkoxyphenoxy)ethanol type of surfactant. The ketal is at least partially soluble in water.

  揭示了具有以下化学式的酮醇：其中R′和R″分别为具有8至约20个碳原子的烷基基团；m和n分别为1至约200的整数；r和s分别为1至3的整数；以及通过使用1,1-二甲氧基环己烷或1,1-二乙氧基环己烷与(烷氧基苯氧基)乙醇型表面活性剂进行转酮缩合制备酮醇的方法。该酮醇至少部分可溶于水。
• Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes
  申请人：McDaniel C. Steven

  公开号：US20100210745A1

  公开（公告）日：2010-08-19

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peotide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文公开了一些聚合材料，如涂层、塑料、层压板、复合材料、弹性体、粘合剂或密封剂；一种表面处理，如纺织品涂层或蜡；一种填料，用于这样的聚合材料或表面处理，其中包括一种酶，如酯酶（例如，脂肪水解酶，硫酸酯水解酶，有机磷化合物降解酶），降解细胞壁和/或细胞膜成分的酶（例如，溶菌酶，裂解转糖基酶），生物杀菌或生物静态肽，以及/或肽酶。本文还公开了通过将酶纳入可通过脂肪水解酶、水解酶和/或脲酶的活性交联材料中来改变材料性能，如使用寿命、柔韧性或刚度的方法。
• Polymeric Coatings Incorporating Bioactive Enzymes for Catalytic Function
  申请人：McDaniel C. Steven

  公开号：US20120097194A1

  公开（公告）日：2012-04-26

  Disclosed herein are materials including a polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a coating, a textile finish or a wax; a filler for such a polymeric material or a surface treatment, which includes an enzyme such as an esterase (e.g., a lipolytic enzyme, an organophosphorus compound degradation enzyme), wherein the enzyme decontaminates a chemical from the surface of the material. Also disclosed herein are methods of cleaning a surface of a material that comprises an enzyme.

  本文公开了一种材料，包括聚合物材料，例如涂层、塑料、层压板、复合材料、弹性体、粘合剂或密封剂；表面处理，例如涂层、纺织品处理或蜡；用于上述聚合物材料或表面处理的填料，其中包括酶，例如酯酶（例如脂肪水解酶、有机磷化合物降解酶），其中酶可从材料表面去除化学物质。本文还公开了一种清洁含有酶的材料表面的方法。
• Polymeric Coatings Incorporating Bioactive Enzymes for Cleaning a Surface
  申请人：Wales Melinda

  公开号：US20110240064A1

  公开（公告）日：2011-10-06

  Disclosed herein are a materials such as a coating, such as an architectural coating or a CARC coating, comprising a lipolytic enzyme or organophosphorous compound degrading enzyme. Also disclosed herein are methods of decontaminating a surface comprising such a material from a chemical substrate of an enzyme such as a lipid or an organophosphorus compound.

  本文公开了一种材料，例如涂层，如建筑涂层或CARC涂层，包括脂肪水解酶或有机磷化合物降解酶。本文还公开了一种从酶的化学底物，例如脂质或有机磷化合物，中去除此类材料表面的污染物的方法。
• Visual Assays for Coatings Incorporating Bioactive Enzymes for Catalytic Functions
  申请人：Williams Eric B.

  公开号：US20110250626A1

  公开（公告）日：2011-10-13

  Disclosed herein are materials such as a coating, comprising a lipolytic enzyme or organophosphrous compound degrading enzyme. Also disclosed herein are methods of visually detecting enzyme activity in a coating by contacting the coating with a substrate of an enzyme and a visual indicator that changes appearance upon production of a product of enzyme activity on a tack-free coating surface.

  本文公开了一种涂层材料，包括脂肪水解酶或有机磷化合物降解酶。本文还公开了一种方法，通过将涂层与酶底物和视觉指示剂接触，以在无粘涂层表面产生酶活性产物时改变外观来检测酶活性的方法。

表征谱图