3,4,5,6-四溴-1,2-苯二羧酸双(2-乙基己基)酯 | 26040-51-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4,5,6-四溴-1,2-苯二羧酸双(2-乙基己基)酯
• 中文别名: 四溴苯酐二辛酯；2,3,4,5-四溴-苯二羧酸双(2-乙基己基)酯(TBPH)；四溴邻苯二甲酸双(2-乙基己基)酯；二-2-乙基己基四溴邻苯二甲酸酯
• 英文名称: bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate
• 英文别名: bis(2-ethylhexyl) 3,4,5,6-tetrabromophthalate；bis(2-ethylhexyl) tetrabromophthalate；di(2-ethylhexyl)tetrabromophthalate；TBPDO；bis(2-ethyl-1-hexyl) tetrabromophthalate；bis (2-ethylhexyl)tetrabromophthalate；bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate
• CAS: 26040-51-7
• 化学式: C₂₄H₃₄Br₄O₄
• 分子量: 706.148
• InChiKey: UUEDINPOVKWVAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  584.8±45.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  10.2 at 25℃
• 物理描述：
  Liquid
• 颜色/状态：
  Liquid
• 蒸汽压力：
  1.7X10-11 mm Hg at 25 °C (est)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

由于多溴联苯醚（PBDE）阻燃剂的逐步淘汰，一些新的化学品，如2-乙基己基-2,3,4,5-四溴苯甲酸酯（TBB）和双（2-乙基己基）2,3,4,5-四溴酞酸酯（TBPH），已被用作某些商业阻燃剂混合物的替代品。这两种化学品在室内尘埃中的浓度接近PBDEs的浓度；然而，关于它们的命运、代谢或毒性知之甚少。本研究的目标是通过进行体外实验，利用肝脏和肠子亚细胞组分来调查这两种溴化阻燃剂在人和大鼠组织中的潜在代谢。在所有实验中，TBB一致通过切断2-乙基己基链代谢为2,3,4,5-四溴苯甲酸（TBBA），而不需要任何添加的辅因子。TBBA也在纯化的猪羧酸酯酶中形成，但速率要快得多，为6.29 +/- 0.58 nmol/min mg/蛋白。估算的人微体中TBB代谢的K(m)和V(max)值分别为11.1 +/- 3.9 uM和0.644 +/- 0.144 nmol/min mg/蛋白。猪羧酸酯酶计算出类似的K(m)为9.3 +/- 2.2 uM，表明相似的酶特异性。TBBA的快速形成可能减少TBB在哺乳动物中的生物累积潜力，并可能作为TBB暴露的生物标志物有用，但这种溴化苯甲酸的毒性是未知的，并且可能因其与其他有毒污染物的结构相似性而引起关注。与TBB相比，TBPH的人或大鼠亚细胞组分中没有检测到代谢物。然而，TBPH的代谢产物，单（2-乙基己基）四溴酞酸酯（TBMEHP），在纯化的猪羧酸酯酶中以大约1.08 pmol/min mg/蛋白的速率形成。没有观察到TBBA或TBMEHP的二期代谢物。需要更多的研究来理解这些化合物在体内的毒动学和健康影响，考虑到它们目前在大多数美国家庭中的普遍存在以及由此导致的慢性暴露的可能性，特别是对幼儿。

Due to the phaseout of polybrominated diphenyl ether (PBDE) flame retardants, new chemicals, such as 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate (TBPH), have been used as replacements in some commercial flame retardant mixtures. Both chemicals have been detected in indoor dust at concentrations approaching the concentrations of PBDEs; however, little is known about their fate, metabolism, or toxicity. The goal of this study was to investigate the potential metabolism of these two brominated flame retardants in human and rat tissues by conducting in vitro experiments with liver and intestinal subcellular fractions. In all the experiments, TBB was consistently metabolized to 2,3,4,5-tetrabromobenzoic acid (TBBA) via cleavage of the 2-ethylhexyl chain without requiring any added cofactors. TBBA was also formed in purified porcine carboxylesterase but at a much faster rate of 6.29 +/- 0.58 nmol/min mg/protein. The estimated K(m) and V(max) values for TBB metabolism in human microsomes were 11.1 +/- 3.9 uM and 0.644 +/- 0.144 nmol/min mg/protein, respectively. A similar K(m) of 9.3 +/- 2.2 uM was calculated for porcine carboxylesterase, indicating similar enzyme specificity. While the rapid formation of TBBA may reduce the bioaccumulation potential of TBB in mammals and may be useful as a biomarker of TBB exposure, the toxicity of this brominated benzoic acid is unknown and may be a concern based on its structural similarity to other toxic pollutants. In contrast to TBB, no metabolites of TBPH were detected in human or rat subcellular fractions. However, a metabolic product of TBPH, mono(2-ethylhexyl) tetrabromophthalate (TBMEHP), was formed in purified porcine carboxylesterase at an approximate rate of 1.08 pmol/min mg/protein. No phase II metabolites of TBBA or TBMEHP were observed. More research is needed to understand the in vivo toxicokinetics and health effects of these compounds given their current ubiquitous presence in most US households and the resulting probability of chronic exposure, particularly to young children.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：双（2-乙基己基）四溴酞酸酯（TBPH）是一种含溴量为45%的阻燃增塑剂，主要用于PVC涂层。人类暴露和毒性：在人类血浆和母乳样本中发现了TBPH。在人类或大鼠亚细胞组分中没有检测到TBPH的代谢物。动物研究：TBPH存在于室内环境的灰尘中（意味着人类暴露），并且可以被猪酯酶代谢为单（2-乙基己基）四溴酞酸酯（TBMEHP），在大鼠模型中，TBMEHP引起了母体甲状腺毒性和肝脏毒性，并诱导了胎儿睾丸中的单核生殖细胞。生态毒性研究：新型溴化阻燃剂具有在体内生物累积和持久性的潜力。

IDENTIFICATION AND USE: Bis(2-ethyhexyl) tetrabromophthalate (TBPH) is a Flame-retardant plasticizer (45% bromine) that finds its main application in PVC coatings. HUMAN EXPOSURE AND TOXICITY: It is found in samples of human plasma and breast milk. No metabolites of TBPH were detected in human or rat subcellular fractions. ANIMAL STUDIES: TBPH is present in dust from indoor environments (implying human exposure) and can be metabolized by porcine esterases to Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP), which elicited maternal thyrotoxic and hepatotoxic effects and induced mononuclear gonocytes in the fetal testes in a rat model. ECOTOXICITY STUDIES: Novel brominated flame retardants have the potential to be bioaccumulative and persistent in vivo.

来源:Hazardous Substances Data Bank (HSDB)

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、球囊阀面罩设备或口袋面罩，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。如果患者呕吐，让患者向前倾或将其置于左侧（如果可能的话，头部向下），以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗救助。 /毒物A和B/

/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/

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，如有需要，辅助通气。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。在运输过程中，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，则用温水冲洗口腔，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/

/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/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、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……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W TKO /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（LR）。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……。/毒物A和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 TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：发育或生殖毒性/ 双-(2-乙基己基)四溴酞酸酯(TBPH)广泛用作商业阻燃混合物中聚溴联苯醚(PBDEs)的替代品，如Firemaster 550。它也用于一种名为DP 45的商业混合物中。单-(2-乙基己基)四溴酞酸酯(TBMEHP)是一种潜在的毒性代谢物。……利用体外和啮齿动物体内模型来评估人类对TBPH的暴露以及TBPH的潜在代谢和毒性。/使用了/从家庭、办公室和汽车收集的灰尘中的TBPH通过气相色谱随后质谱进行测量。妊娠大鼠在妊娠第18和19天通过胃管给予TBMEHP（200或500毫克/千克）或玉米油，并对母体和胎儿进行组织学毒性评估。/该研究/评估了TBMEHP对大鼠肝微粒体脱碘酶抑制以及对小鼠FAO细胞和NIH 3T3 L1细胞中过氧化物酶体增殖激活受体（PPAR）alpha和gamma激活的影响。办公大楼灰尘中的TBPH浓度（中位数，410 ng/g）高于家庭主要生活区域（中位数，150 ng/g）。TBPH通过纯化的猪酯酶代谢为TBMEHP。在大鼠中，两天TBMEHP暴露导致母体甲状腺功能减退，血清T3（3,3',5-三碘-l-甲状腺原氨酸）显著降低，母体肝毒性增加，胎儿睾丸中多核生殖细胞（MNGs）增加，但没有抗雄激素作用。在体外，TBMEHP抑制了脱碘酶活性，诱导了NIH 3T3 L1细胞的脂肪细胞分化，并在NIH 3T3 L1细胞和FAO细胞中分别激活了PPAR(alpha)-和PPAR(gamma)-介导的基因转录。TBPH存在于室内环境（暗示人类暴露）的灰尘中，并且可以通过猪酯酶代谢为TBMEHP，在大鼠模型中引起了母体甲状腺毒性和肝毒性以及胎儿睾丸中MNGs的增加。在小鼠NIH 3T3 L1前脂肪细胞中，TBMEHP抑制了大鼠肝微粒体脱碘酶活性，并在小鼠FAO和NIH 3T3 L1细胞中作为PPAR的激动剂。/双-(2-乙基己基)四溴酞酸酯(TBPH)及其代谢物单-(2-乙基己基)四溴酞酸酯(TBMEHP)/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Bis-(2-ethylhexyl) tetrabromophthalate (TBPH) is widely used as a replacement for polybrominated diphenyl ethers (PBDEs) in commercial flame retardant mixtures such as Firemaster 550. It is also used in a commercial mixture called DP 45. Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP) is a potentially toxic metabolite. ... In vitro and rodent in vivo models to evaluate human exposure and the potential metabolism and toxicity of TBPH /were used/. Dust collected from homes, offices, and cars was measured for TBPH by gas chromatography followed by mass spectrometry. Pregnant rats were gavaged with TBMEHP (200 or 500 mg/kg) or corn oil on gestational days 18 and 19, and dams and fetuses were evaluated histologically for toxicity. /The study/ assessed TBMEHP for deiodinase inhibition using rat liver microsomes and for peroxisome proliferator-activated receptor (PPAR) alpha and gamma activation using murine FAO cells and NIH 3T3 L1 cells. TBPH concentrations in dust from office buildings (median, 410 ng/g) were higher than in main living areas in homes (median, 150 ng/g). TBPH was metabolized by purified porcine esterases to TBMEHP. Two days of TBMEHP exposure in the rat produced maternal hypothyroidism with markedly decreased serum T3 (3,3',5-triiodo-l-thyronine), maternal hepatotoxicity, and increased multinucleated germ cells (MNGs) in fetal testes without antiandrogenic effects. In vitro, TBMEHP inhibited deiodinase activity, induced adipocyte differentiation in NIH 3T3 L1 cells, and activated PPAR(alpha)- and PPAR(gamma)-mediated gene transcription in NIH 3T3 L1 cells and FAO cells, respectively. TBPH is present in dust from indoor environments (implying human exposure) and can be metabolized by porcine esterases to TBMEHP, which elicited maternal thyrotoxic and hepatotoxic effects and induced MNGs in the fetal testes in a rat model. In mouse NIH 3T3 L1 preadipocyte cells, TBMEHP inhibited rat hepatic microsome deiodinase activity and was an agonist for PPARs in murine FAO and NIH 3T3 L1 cells. /Bis-(2-ethylhexyl) tetrabromophthalate (TBPH) and metabolite Mono-(2-ethyhexyl) tetrabromophthalate (TBMEHP)/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

作者评估了3种非多溴联苯醚（PBDE）溴化阻燃剂的生物累积潜力：1,2-双(2,4,6-三溴苯氧基)乙烷（BTBPE），四溴双酚A双(2,3-二溴丙基醚)（TBBPA-BDBPE），以及BZ-54，是双(2-乙基己基)四溴酞酸酯)（BEH-TEBP）和2-乙基己基-2,3,4,5-四溴苯甲酸酯（EH-TBB）的混合物。复制的户外水体模拟系统单独处理，设计的浓度使得沉积物上层5厘米内的阻燃剂负荷达到最大500 ng/g。每个模拟系统中引入了笼养的胖头鱼（Pimephales promelas，每个重复24条鱼），并在暴露前适应了10天。暴露期为42天，随后转移到控制模拟系统中进行28天的排毒，在此期间检查了物理、生殖和生化终点。取组织样本以测量NBFRs的积累、排毒和生物转化。观察到胖头鱼在生长调整后积累了BTBPE（16-4203 ng/g脂质）和TBBPA-BDBPE（>1000 ng/g脂质），但EH-TBB和BEH-TEBP没有观察到一致的积累。然而，监测到的物理、生殖和生化参数没有显示出有生物学意义或一致性的响应。每个处理组的胖头鱼表现出几种溴化转化产物。该研究得出结论，这些NBFRs具有体内生物累积和持久性，因此，需要进一步研究与其慢性、亚致死响应相关的生理效应。

The authors assessed the bioaccumulation potential of 3 non-PBDE brominated flame retardants: 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE), tetrabromobisphenol A bis(2,3-dibromopropylether) (TBBPA-BDBPE), and BZ-54, a mixture of bis(2-ethylhexyl)tetrabromophthalate) (BEH-TEBP) and 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (EH-TBB). Replicate outdoor aquatic mesocosms were treated individually at concentrations designed to give a maximum load of 500 ng/g of flame retardant in the upper 5 cm of the sediment. Caged fathead minnows (Pimephales promelas, 24 fish per replicate) were introduced to each mesocosm and acclimated for 10 days prior to exposure. The exposure period was 42 days, followed by 28 days of depuration after transfer to a control mesocosm, during which physical, reproductive, and biochemical end points were examined. Tissue samples were taken to measure the accumulation, depuration, and biotransformation of NBFRs. Fathead minnows were observed to accumulate, after growth adjustment, BTBPE (16-4203 ng/g lipid) and TBBPA-BDBPE (>1000 ng/g lipid) but with a lack of consistent accumulation observed for EH-TBB and BEH-TEBP. However, limited biologically meaningful or consistent responses were observed in the monitored physical, reproductive, and biochemical parameters. Fathead minnows from each treatment exhibited several brominated transformation products. The /study concludes/ that these NBFRs have the potential to be bioaccumulative and persistent in vivo and, therefore, warrant further study of physiological effects linked to chronic, sublethal responses.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H227,H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

反应信息

• 作为产物：
  描述：

  2-乙基己醇 、 四溴苯酐 在 titanium(IV) 2-ethylhexoxide 作用下， 反应 6.0h， 以692 g的产率得到3,4,5,6-四溴-1,2-苯二羧酸双(2-乙基己基)酯
  参考文献：
  名称：

  Plasticized polyvinyl chloride compound

  摘要：

  一种高阻燃的增塑聚氯乙烯化合物（PVC）包括二烷基四氯邻苯二甲酸酯和二烷基四溴邻苯二甲酸酯的混合物，并且具有无脆性和在低温下具有所需的PVC成型夹克和导线电缆绝缘材料的显著柔韧性。

  公开号：

  US06369264B2

文献信息

• [EN] PROCESS FOR PRODUCING TETRABROMOBENZOATE ESTERS<br/>[FR] PROCEDE DE PRODUCTION D'ESTERS DE TETRABROMOBENZOATE
  申请人：PABU SERVICES INC

  公开号：WO2005016863A1

  公开（公告）日：2005-02-24

  A method for preparing tetrabromobenzoate ester from a tetrabromophthalic anhydride including the steps of reacting the tetrabromophthalic anhydride with a catalyst and an alcohol at a temperature that favors partial esterification over complete esterification of the tetrabromophthalic anhydride to form a tetrabromophthalate half-ester reaction mixture; and feeding the half-ester reaction mixture to at least one reactor having and maintaining a temperature that favors decarboxylation over esterification to produce a tetrabromobenzoate ester-containing product. The temperature favoring partial esterification of the tetrabromophthalic anhydride is between about 70°C and 130°C. The temperature favoring decarboxylation over esterification is between about 190°C and 205°C. The tetrabromobenzoate ester-containing product comprises at least about 85% tetrabromobensoate ester. The at least one reactor may include two or more reactors connected to one another in series.

  一种从四溴邻苯二甲酸酐制备四溴苯甲酸酯的方法，包括以下步骤：将四溴邻苯二甲酸酐与催化剂和醇在有利于部分酯化而非完全酯化的温度下反应，形成四溴邻苯酸半酯反应混合物；将半酯反应混合物送入至少一个反应器中，并保持有利于脱羧而非酯化的温度，以生成含有四溴苯甲酸酯的产物。有利于四溴邻苯二甲酸酐部分酯化的温度在约70°C至130°C之间。有利于脱羧而非酯化的温度在约190°C至205°C之间。四溴苯甲酸酯含有产物至少约85％的四溴苯甲酸酯。至少一个反应器可以包括连接在一起的两个或更多个连续反应器。
• 一种四溴邻苯二甲酸双（2-乙基己基）酯的合成方法
  申请人：山东润科化工股份有限公司

  公开号：CN109776317A

  公开（公告）日：2019-05-21

  本发明涉及一种四溴邻苯二甲酸双(2‑乙基己基)酯的合成方法，解决了现有技术具有合成成本高，合成步骤繁琐、所得产品纯度低、着色深的技术问题。本发明提供一种四溴邻苯二甲酸双(2‑乙基己基)酯的合成方法，包括以下步骤：将四溴邻苯二甲酸酐与2‑乙基己醇按比例加入反应容器中，加入中和剂a除去体系内的无机酸残留，通入惰性保护气，加入催化剂b后升温反应，通过水分离器将体系生成的水分离，反应完成后，除去催化剂b，通过水蒸气蒸馏汽提出过量的2‑乙基己醇，粗品加入过氧化物及复合脱色剂脱除深色副产物，得到具有较浅着色的四溴邻苯二甲酸双(2‑乙基己基)酯产品。本发明广泛应用于阻燃剂合成技术领域。
• Process for producing tetrabromobenzoate esters
  申请人：Bartley W. David

  公开号：US20050027139A1

  公开（公告）日：2005-02-03

  A method for preparing tetrabromobenzoate ester from a tetrabromophthalic anhydride including the steps of reacting the tetrabromophthalic anhydride with a catalyst and an alcohol at a temperature that favors partial esterification over complete esterification of the tetrabromophthalic anhydride to form a tetrabromophthalate half-ester reaction mixture; and feeding the half-ester reaction mixture to at least one reactor having and maintaining a temperature that favors decarboxylation over esterification to produce a tetrabromobenzoate ester-containing product. The temperature favoring partial esterification of the tetrabromophthalic anhydride is between about 70° C. and 130° C. The temperature favoring decarboxylation over esterification is between about 190° C. and 205° C. The tetrabromobenzoate ester-containing product comprises at least about 85% tetrabromobenzoate ester. The at least one reactor may include two or more reactors connected to one another in series.

  从四溴邻苯二甲酸酐制备四溴苯甲酸酯的方法，包括以下步骤：在偏向于部分酯化而非完全酯化四溴邻苯二甲酸酐的温度下，将四溴邻苯二甲酸酐与催化剂和醇反应，形成四溴邻苯酸酯半酯反应混合物；将半酯反应混合物送入至少一个反应器，并保持偏向于脱羧而非酯化的温度，以产生含有四溴苯甲酸酯的产品。偏向于部分酯化四溴邻苯二甲酸酐的温度在约70°C至130°C之间。偏向于脱羧而非酯化的温度在约190°C至205°C之间。四溴苯甲酸酯含有产品至少含有约85%的四溴苯甲酸酯。至少一个反应器可能包括连接在串联中的两个或更多反应器。
• Efficient methods for making tetrahalophthalate esters having excellent
  申请人：Great Lakes Chemical Corporation

  公开号：US06150552A1

  公开（公告）日：2000-11-21

  Provided are methods for the preparation and purification of alkyl tetrahalophthalate esters by the reaction of a tetrahalophthalic compound with an alkanol in the presence of a titanate catalyst. More particularly, improved methods are provided for making and recovering an ester with little contamination by catalytic metal components and color bodies, and with little acidity, in a high yield from the esterification reaction by pretreating the starting materials to reduce the acidity thereof, reacting the starting materials in the presence of a titanate catalyst, stripping excess alcohol, hydrolyzing the catalyst, and filtering out solids to yield a high purity tetrahalophthalate ester product.

  提供了一种通过四卤基邻苯二酸化合物在乙醇存在下与烷醇反应制备和纯化烷基四卤基邻苯二酸酯的方法，其中使用钛酸盐催化剂。更具体地，提供了改进的方法，通过预处理起始材料以减少酸度，使用钛酸盐催化剂反应起始材料，蒸馏过量的醇，水解催化剂，并过滤固体以获得高纯度的四卤基邻苯二酸酯产物，从而制备和回收少量含有催化金属成分和色体的酯，并且收率高。
• Process for preparing alkyl tetrabromophthalates
  申请人：Great Lakes Chemical Corporation

  公开号：US04754053A1

  公开（公告）日：1988-06-28

  Bis(2-ethyl-1-hexyl) tetrabromophthalate produced by the reaction of tetrabromophthalic anhydride with 2-ethyl-1-hexanol in the presence of titanium isopropoxide catalyst may be purified by contacting the reaction mixture with sodium carbonate decahydrate with agitation for a time and at a temperature sufficient to enhance product quality, followed by isolation of bis(2-ethyl-1-hexyl) tetrabromophthalate.

  在钛异丙醇催化剂的存在下，四溴邻苯二甲酸酐与2-乙基-1-己醇反应生成的双(2-乙基-1-己基)四溴邻苯二甲酸酯，可通过将反应混合物与十水合碳酸钠接触并在足够的时间和温度下搅拌以提高产品质量，然后分离双(2-乙基-1-己基)四溴邻苯二甲酸酯来纯化。