1,2-双(四溴邻苯二甲酰亚胺)乙烷 | 32588-76-4

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 1,2-双(四溴邻苯二甲酰亚胺)乙烷
• 中文别名: 阻燃剂BT-93W；乙撑双(四溴邻苯二甲酰胺)；乙撑双四溴邻苯二甲酰亚胺
• 英文名称: N,N'-ethylenebis(3,4,5,6-tetrabromophthalimide)
• 英文别名: N,N'-ethylene-bis(tetrabromophthalimide)；1,2-bis(tetrabromophthalimido)ethane；N,N',-1,2-ethylene-bis-(tetrabromophthalimide)；N,N'-(1,2,-ethylene)-bis[3,4,5,6-tetrabromophthalimide]；ethylene bis-(tetrabromophthalimide)；N,N-Ethylene-bis(tetrabromophthalimide)；4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione
• CAS: 32588-76-4
• 化学式: C₁₈H₄Br₈N₂O₄
• mdl: MFCD00467117
• 分子量: 951.473
• InChiKey: DYIZJUDNMOIZQO-UHFFFAOYSA-N

物化性质

• 熔点：
  446°C
• 沸点：
  827.9±65.0 °C(Predicted)
• 密度：
  2.67
• LogP：
  9.797
• 物理描述：
  N,n-ethylene-bis(tetrabromophthalimide) is a yellow powder. (NTP, 1992)
• 颜色/状态：
  Off-white powder
• 溶解度：
  Solubility (weight % at 25 °C): <0.01 in water, acetone, methanol, toluene
• 蒸汽压力：
  2.5X10-22 mm Hg at 25 °C /Estimated/
• 折光率：
  Index of refraction = 1.77

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

毒理性

• 毒性数据

大鼠(吸入) > 203,000 毫克/立方米/小时

LC (rat) > 203,000 mg/m3/1h

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

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，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……。预见并处理癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。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……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于无意识、严重肺水肿或呼吸停止的患者，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。监测心率和必要时治疗心律失常。 ... 开始静脉输液，使用D5W/SRP：“保持开放”，最低流量/。如果出现低血容量的迹象，使用乳酸钠林格氏液。注意液体过载的迹象。考虑使用药物治疗肺水肿。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象。用地西泮（安定）治疗癫痫。使用丙美卡因氢氯化物协助眼部冲洗。/毒药A和B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

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/ 测试物质（0.5克）被涂抹在6只白兔的完好和磨损皮肤上。测试物质被覆盖上封闭敷料，并保持接触24小时。在涂抹后24小时和72小时进行皮肤读数。所有兔在这两次读数中红斑、焦痂和水肿形成的评分均为0。

/LABORATORY ANIMALS: Acute Exposure/ The test material (0.5 g) was applied to intact and abraded skin of 6 white rabbits. The test material was covered with an occlusive dressing and remained in contact for 24 hr. Skin readings were made at 24 and 72 hr post-application. All rabbits at both readings scored 0 for erythema, eschar, and edema formation.

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/ 测试物品被滴入6只新西兰白兔的右眼。在处理后1小时、24小时、48小时、72小时以及第7天记录观察结果。在滴入后1小时，5只动物的结膜出现红肿，得分为1，24小时时，1只动物的得分为2。分泌物（得分为1）在2只动物中观察到。所有6只动物对于 chemosis（结膜水肿）的检查结果为阴性。所有6只动物的角膜病变和虹膜效应得分为0。其他时间点的所有得分均为阴性。

/LABORATORY ANIMALS: Acute Exposure/ The test article was instilled in the right eye of 6 New Zealand white rabbits. Observations were recorded at 1, 24, 48, and 72 hr and on Day 7 following treatment. At 1 hr after instillation, conjunctival redness was detected in 5 animals with a score of 1 and in 1 animal with a score of 2 at 24 hours. Discharge (score = 1) was noted in 2 animals. All 6 animals were negative for chemosis. All 6 animals scored 0 for corneal lesions and iris effects. All scores at other time points were negative.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

14C标记的BT93通过口服灌胃的方式给予5只雌性Sprague-Dawley大鼠，连续给药14天。在最后一次给药后24小时处死两只大鼠；其余大鼠在最后一次给药后7、14和30天处死。每次处死时收集肝脏、肾脏、大脑、腿部肌肉和体脂。在最后一次给药后24小时收集尿液、粪便和呼出气体。该化合物主要通过粪便排出（约占总剂量的65%）。约15%的总剂量在尿液中找到。呼出气体中排出的放射性标记物数量可以忽略不计。在组织中暂时检测到少量14C标记物；任何组织中的残留物都小于0.5 ppm。在撤药期间处死的动物组织中，残留物水平在30天撤药期内全部消散。肾脏水平从最后一次给药后24小时的0.32 ppm降至第30天的0.043 ppm；肝脏从最后一次给药后24小时的0.424 ppm降至第30天的0.024 ppm。

14C-labelled BT93 was administered orally by gavage in corn oil to 5 female Sprague-Dawley rats for 14 consecutive days. Two rats were sacrificed 24 hr after the last dose; remainder sacrificed 7, 14, and 30 days after the last dose. Liver, kidney, brain, leg muscle and body fat were collected at each sacrifice. Urine, feces and expired air was collected 24 hr after the last dose. The compound was excreted mainly in the feces (approximately 65% of the total dose). Approximately 15% of the total dose was found in the urine. The amount of the radiolabel excreted in expired air was negligible. A minor trace amount of 14C-label was temporarily detected in tissues; residues were <0.5 ppm in any tissue. Tissues from animals sacrificed during the withdrawal period showed a dissipation of residue levels in all tissues within the 30 withdrawal period. Kidney level went from 0.32 ppm 24 hr after the last dose to 0.043 ppm at day 30 post dosing; liver went from 0.424 ppm 24 hr after the last dose to 0.024 ppm at day 30 post dosing.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• WGK Germany：
  3
• 海关编码：
  2925190090

制备方法与用途

化学性质
这是一种浅黄色、流动性良好的粉末。其熔点为450℃，分解温度则高于450℃。相对密度为2.66，含溴量达到66%。在不同溶剂中的溶解度（单位：克/100克溶剂，在25℃下）分别为：丙酮、苯、邻二氯苯和二甲酰胺中的溶解度均低于0.05；棉子油中为0.015；而在水中则仅为0.002。

用途
本产品是国外近期研发的一种添加型阻燃剂，具有优良的光热稳定性。它不挥发、无臭味且不会析出，同时也不会影响制品的电性能。该阻燃剂适用于高抗冲聚苯乙烯、聚丙烯、聚乙烯、热塑性聚酯、尼龙、乙丙共聚物及聚碳酸酯等多种高分子材料。

生产方法
该产品的合成采用四溴苯酐、甲醇和乙二胺为原料，经过两步反应制成。首先，在甲醇中加热回流四溴苯酐，得到四溴邻苯二甲酸单甲酯；随后，加入乙二胺的甲醇溶液并继续进行回流反应。待反应完成，冷却后过滤、干燥，便得到白色结晶状的乙撑二铵双（四溴邻苯二甲酸单甲酯）。最后，在真空条件下于136℃下加热较长时间，即可获得所需的乙撑双（四溴邻苯二甲酰胺）产物。

反应信息

• 作为产物：
  描述：

  四溴苯酐 、 乙二胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以91 %的产率得到1,2-双(四溴邻苯二甲酰亚胺)乙烷
  参考文献：
  名称：

  CN117050553

  摘要：

  公开号：

文献信息

• [EN] STERICALLY HINDERED AMINE STABILIZERS<br/>[FR] STABILISANTS D'AMINES À ENCOMBREMENT STÉRIQUE
  申请人：BASF SE

  公开号：WO2010142572A1

  公开（公告）日：2010-12-16

  The instant invention pertains to hindered amine compounds having at least two nitrogen atoms with different basicity. One part is substituted on the N-atom by alkoxy moieties and the other part is substituted on the N-atom by a hydroxy-alkyl moiety. These materials are particularly effective in stabilizing polymers, especially thermoplastic polyolefins, against the deleterious effects of oxidative, thermal and actinic radiation. The compounds are also particularly effective in stabilizing acid catalyzed and ambient cured coatings systems.

  这项瞬时发明涉及具有至少两个氮原子且碱度不同的受阻胺化合物。其中一部分在N原子上被烷氧基团取代，另一部分在N原子上被一个羟基-烷基基团取代。这些材料在稳定聚合物方面特别有效，尤其是热塑性聚烯烃，可以抵御氧化、热和光辐射的有害影响。这些化合物在稳定酸催化和环境固化的涂层系统方面也特别有效。
• SULFENAMIDES AS FLAME RETARDANTS
  申请人：SONGWON INTERNATIONAL AG

  公开号：US20160289566A1

  公开（公告）日：2016-10-06

  The present invention is in the field of flame retardants and relates to use of sulfenamides as flame retardants, in particular in polymeric substrates.

  本发明属于阻燃剂领域，涉及将硫代酰胺用作阻燃剂，特别是在聚合物基材中的使用。
• USE OF PHOSPHOROUS-CONTAINING ORGANIC OXYIMIDES AS FLAME RETARDANTS AND/OR AS STABILIZERS FOR PLASTICS, FLAME-RETARDANT AND/OR STABILIZED PLASTIC COMPOSITIONS, METHOD FOR THE PRODUCTION THEREOF, MOULDED PART, PAINT AND COATINGS
  申请人：FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E.V.

  公开号：US20170260366A1

  公开（公告）日：2017-09-14

  The present invention relates to the use of phosphorous-containing organic oxyimides according to the general formula (I) as flame retardant for plastic materials, as radical generators in plastic materials and/or stabilisers for plastics. In addition, the present invention relates to a flame-retardant plastic material moulding compound in which the previously described phosphorous-containing organic oxyimides are integrated, and also to a method for the production of the previously mentioned plastic material composition. Furthermore, the present invention relates to a moulded article, a paint or a coating from the previously mentioned flame-retardant plastic material composition.

  本发明涉及根据一般式(I)的含磷有机氧亚胺化合物作为塑料材料的阻燃剂，作为塑料材料中的自由基发生剂和/或塑料的稳定剂。此外，本发明涉及一种阻燃塑料材料成型复合物，其中集成了前述的含磷有机氧亚胺化合物，并且涉及一种用于制备前述塑料材料组合物的方法。此外，本发明涉及一种从前述阻燃塑料材料组合物制成的成型制品、涂料或涂层。
• [EN] PHOSPHO-SUBSTITUTED ALKOXYAMINE COMPOUNDS<br/>[FR] COMPOSÉS ALCOXYAMINE SUBSTITUÉS PAR DES GROUPES PHOSPHO
  申请人：BASF SE

  公开号：WO2011086114A1

  公开（公告）日：2011-07-21

  The invention relates to compounds of the group of so-called sterically hindered amines (HALS) which are substituted by phospho groups. The invention also relates to flame retardant compositions wherein these compounds are added to the polymer substrate.

  该发明涉及一类所谓的受空间位阻影响的胺化合物（HALS），这些化合物被磷基取代。该发明还涉及阻燃组合物，其中这些化合物被添加到聚合物基质中。
• Benzotriazoles containing phenyl groups substituted by heteroatoms and compositions stabilized therewith
  申请人：——

  公开号：US20030004235A1

  公开（公告）日：2003-01-02

  2H-Benzotriazole UV absorbers substituted at the 3-position and/or the 5-position of the phenyl ring by a phenyl moiety which is substituted by a heteroatom are particularly photostable in automotive coatings, and are of low color and exhibit low volatility in thermoplastic compositions.

  3-位和/或5-位被苯基环上的苯基取代的2H-苯并三唑紫外线吸收剂，其被异原子取代的苯基特别在汽车涂料中具有光稳定性，并且在热塑性复合材料中具有低色度和低挥发性。