氯化链烷烃 | 63449-39-8

• 物质功能分类: 催化剂及助剂 - 塑料橡胶助剂 - 增塑剂
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 氯化链烷烃
• 中文别名: 氯化石蜡；氯代烷烃
• 英文名称: Cereclor
• 英文别名: 4,8,11,14,17,21-hexachlorotetracosane
• CAS: 63449-39-8
• 化学式: C₂₄H₄₄Cl₆
• 分子量: 545.3
• InChiKey: QKUNKVYPGIOQNP-UHFFFAOYSA-N

物化性质

• 熔点：
  95-110
• 沸点：
  413-508℃
• 密度：
  1.387 g/mL at 20 °C(lit.)
• 闪点：
  392
• 溶解度：
  溶于四氢呋喃，溶解度为0.1g/mL，澄清
• LogP：
  5.88-12.83 at 18.7-20℃ and pH6-7
• 物理描述：
  Chlorowax 40 appears as clear to light amber or yellow viscous liquid with a slightly pungent odor. Compound flows only very slowly. (NTP, 1992)
• 颜色/状态：
  Generally they are viscous liquids.
• 气味：
  Usually odorless. However, those with high chlorine content (65% or over) have an odor.
• 蒸汽压力：
  Nonvolatile (NTP, 1992)
• 稳定性/保质期：
  Stable in air

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

/已经证明/细胞色素P-450（CYP）的诱导剂和抑制剂影响暴露于C57Bl小鼠的含68.5%（CP-SH）、55.9%（CP-SH）和17.4%Cl（CP-SL）的（14）C标记的多氯代十二烷（C12）降解为（14）CO2的速率。抑制剂胡椒基丁氧提前处理减少了形成的（14）CO2量，且随着氯化度的增加，这种减少更为明显。抑制剂美替拉酮减少了（14）CO2的呼出量，但只在暴露于C12;68.5%Cl的小鼠中进行了研究。细胞色素P-450（CYP2B1; CYP2B2）诱导剂，苯巴比妥，适度增加了含68%Cl氯化石蜡形成（14）CO2的速率，而P-448（CYP1A1; CYP1A2）诱导剂，3-甲基胆蒽，并未影响降解速率，这表明氯代十二烷通过细胞色素P-450依赖性代谢产生（14）CO2。/短链氯化石蜡/

/It was/ demonstrated that inducers and inhibitors of cytochrome P-450 (CYP) affect the rate of degradation of (14)C-labeled polychlorinated dodecanes (C12) containing 68.5% (CP-SH), 55.9% (CP-SH) and 17.4% Cl (CP-SL) to (14)CO2 in exposed C57Bl mice. Pretreatment with the inhibitor piperonyl butoxide decreased the amount of (14)CO2 formed, and the decrease was more pronounced with increasing degree of chlorination. The inhibitor metyrapone decreased the exhalation of (14)CO2 but was only investigated in mice exposed to C12;68.5% Cl. The cytochrome P-450 (CYP2B1; CYP2B2) inducer, phenobarbital, moderately increased the rate of (14)CO2 formation from chlorinated paraffin with 68% Cl, whereas the P-448 (CYP1A1; CYP1A2) inducer, 3-methylcholanthrene, did not affect the degradation rate, indicating a cytochrome P-450-dependent metabolism of chlorinated dodecanes yielding (14)CO2. /Short chain length chlorinated paraffin/

来源:Hazardous Substances Data Bank (HSDB)

代谢

Sprague-Dawley雌性大鼠，每组四只，静脉注射5-6 mg/kg体重的(14)C标记的多氯代十六烷（C16;65% Cl, CP-MH）。胆汁中不到3%的放射性是由于未改变的母化合物。胆汁中的代谢物似乎是N-乙酰半胱氨酸（巯基尿酸）和谷胱甘肽的共轭物。/中等链长氯化石蜡/

Female Sprague-Dawley rats in groups of four were exposed intravenously to 5-6 mg/kg body weight of (14)C-labeled poly-chlorinated hexadecane (C16;65% Cl, CP-MH). Less than 3% of the radioactivity in the bile was due to unchanged parent compound. The metabolites in the bile appeared to be conjugates of N-acetylcysteine (mercapturic acid) and glutathione. /Intermediate chain length chlorinated paraffin/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：有充分证据表明，在实验动物中，平均碳链长度为C12、平均氯含量为60%的商业氯化石蜡产品具有致癌性。对于平均碳链长度为C23、平均氯含量为43%的商业氯化石蜡产品在实验动物中的致癌性，证据有限。关于氯化石蜡在人类中的致癌性，没有来自人体研究的数据。总体评估：平均碳链长度为C12、平均氯含量大约为60%的氯化石蜡可能对人类具有致癌性（2B组）。

Evaluation: There is sufficient evidence for the carcinogenicity of a commercial chlorinated paraffin product of average carbon-chain length C12 and average degree of chlorination 60% in experimental animals. There is limited evidence for the carcinogenicity of a commercial chlorinated paraffin product of average carbon-chain length C23 and average degree of chlorination 43% in experimental animals. No data were available from studies in humans on the carcinogenicity of chlorinated paraffins. Overall evaluation: Chlorinated paraffins of average carbon-chain length C12 and average degree of chlorination approximately 60% are possibly carcinogenic to humans (Group 2B).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

氯化烷基: 有合理预期对人来说是致癌物。/氯化烷基 (C12, 60% 氯)/

Chlorinated Paraffins: reasonably anticipated to be human carcinogens. /Chlorinated Paraffins (C12, 60% Chlorine)/

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，让患者身体前倾或将其置于左侧（如果可能，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……。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 /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）或乳酸林格氏液。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……。使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……。 /Poisons A and 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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)

吸收、分配和排泄

氯化烷基链缓慢通过Sprague-Dawley大鼠的皮肤途径被吸收。两种标记有(14)C的氯化烷基链，C18;50-53% Cl (CP-LH) 和 C28;47% Cl (CP-LL)，以66 mg/平方厘米的浓度涂抹在大鼠皮肤上（每种性别5-7只动物），大约相当于2000 mg/kg体重。96小时后，仅吸收了0.7%（雄性）和0.6%（雌性）的C18剂量。C28剂量在雄性中仅吸收了0.02%，而在雌性中水平无法检测。这表明随着链长增加，渗透性降低。吸收的C18剂量中，40%以(14)C标记的CO2形式呼出，20%通过尿液排出，20%通过粪便排出。/长链氯化烷基链/

Chlorinated paraffins are slowly absorbed by the dermal route in Sprague-Dawley rats. Two (14)C-labeled chlorinated paraffins, C18;50-53% Cl (CP-LH) and C28;47% Cl (CP-LL), were applied to rat skin (5-7 animals of each sex) at a concentration of 66 mg/sq cm, approximately equivalent to 2000 mg/kg body weight. Only 0.7% (males) and 0.6% (females) of the C18 dose was absorbed after 96 hr. Only 0.02% of the C28 dose was absorbed in males whereas in females the level was not detectable. This indicates that increasing chain length leads to decreased permeability. Of the absorbed C18 dose, 40% was exhaled as (14)C-labeled CO2, and 20% was excreted in urine and 20% in feces. /Long chain length chlorinated paraffins/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

两种氯代石蜡通过人体皮肤的吸收已经在体外进行了研究。在将Cereclor S52（C14-19; 52% Cl, CP-MH）涂抹在表皮膜表面并使用五种不同的受体介质的情况下，经过54小时的涂抹后没有发现吸收。同样，使用Cereclor 56L（C10-13; 56% Cl, CP-SH; 在典型切削油中18.5% w/w的溶液）在7小时内也没有检测到吸收，但在23小时后检测到了缓慢但稳定的吸收速率（例如，0.05 +/- 0.01微克/平方厘米每小时 +/- 标准误；n = 6；受体介质为盐水中的PEG-20油酸酯），这种吸收速率在实验期间（56小时）保持不变。由于预计吸收率较低，Cereclor S52和56L的氯代石蜡样品分别用[(14)C]正十五烷和[(14)C]正十一烷进行了标记，以便于检测吸收的物质。测量(14)C-烷烃的量被作为氯代石蜡的替代指标，基于它们的吸收率相似的假设。

The absorption of two chlorinated paraffins through human skin has been studied in vitro. There was no absorption of Cereclor S52 (C14-19;52% Cl, CP-MH) following a 54-hr application to the surface of the epidermal membranes using five different receptor media. Similarly, using Cereclor 56L (C10-13; 56% Cl, CP-SH; 18.5% w/w solution in a typical cutting oil) no absorption was detected for 7 hr, but after 23 hr a slow but steady rate of absorption was detected (e.g., 0.05 +/- 0.01 ug/sq cm per hr +/- SEM; n = 6; receptor medium PEG-20 oleyl ether in saline), which was maintained for the duration of the experiment (56 hr). Owing to the anticipated low rate of absorption, the chlorinated paraffin samples were spiked with [(14)C] n-pentadecane and [(14)C] n-undecane for Cereclor S52 and 56L, respectively, in order to facilitate detection of the absorbed material. Measurement of the (14)C-alkanes was taken as a surrogate for the chlorinated paraffins, on the assumption that their rates of absorption were similar.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

C57Bl雌性小鼠通过灌胃或静脉注射给予不同氯含量（17.5%[CP-SL]，55.9%[CP-SH]和68.5%[CP-SH]）的(14)C标记的氯代十二烷（C12），剂量为12.5 MBq/kg体重（340 uCi）（用于放射自显影）或1.25 MBq/kg体重（34 uCi）（用于测定放射性活性）。通过放射自显影发现，放射性活性的摄取在细胞转换率高/代谢活性高的组织中最高，例如，肠粘膜、骨髓、唾液腺、胸腺和肝脏。含氯量最低的氯化石蜡实现了最高的放射性活性。研究发现，口服给药后，肝脏和脂肪中未代谢物质的庚烷溶性放射性活性的长时间滞留随着氯化程度的增加而增加。在这项研究中还发现，注射C12;17.5% Cl和C12;55.9% Cl后30至60天，中枢神经系统中有显著的放射性活性滞留。暴露于晚期妊娠的小鼠显示放射性活性通过胎盘传递，(14)C标记主要在胎儿的肝脏、棕色脂肪和肠中观察到。/短链氯化石蜡/

Female C57Bl mice were administered 12.5 MBq/kg body weight (340 uCi) (for autoradiography) or 1.25 MBq/kg body weight (34 uCi) (for determination of radioactivity) of (14)C-labeled chlorododecanes (C12) with different chlorine contents (17.5% [CP-SL], 55.9% [CP-SH] and 68.5% [CP-SH]) either by gavage or intravenous injection. Uptake of radioactivity was found by autoradiography to be highest in tissues with high cell turnover/high metabolic activity, e.g., intestinal mucosa, bone marrow, salivary glands, thymus and liver. The highest radioactivity was achieved with the chlorinated paraffin that had the lowest chlorine content. It was found that the long period of retention of heptane-soluble radioactivity, which indicated unmetabolized substance, in liver and fat after oral dosing increased with degree of chlorination. In this study it was also found that 30 to 60 days after injection of C12;17.5% Cl and C12;55.9% Cl a considerable retention of radioactivity was seen in the central nervous system. Exposure of late gestation mice showed a transplacental passage of radioactivity, and (14)C-labeling was primarily noted in the liver, brown fat and intestine of the fetuses. /short chain length chlorinated paraffin/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C标记的[1-(14)C]多氯十六烷（C16; 34.1% Cl, CP-ML）以370 kBq/动物（10 uCi）（相当于0.44 umol的氯化蜡）的放射性水平通过灌胃（雌性）或静脉注射（两性）给予C57Bl小鼠。口服和静脉给药途径之间的分布模式没有差异。通过自动放射性显影分析后发现，在细胞更新率较高和/或代谢活动较高的组织中放射性活性较高，而在白色脂肪库中可以观察到较低的水平。静脉注射后24小时，在肝脏、肾脏、脾脏、骨髓、棕色脂肪、肠粘膜、胰腺、唾液腺和哈德氏腺中观察到高水平的放射性活性。12天后，在肾上腺皮质、腹部脂肪和胆汁中观察到高水平的放射性活性。注射后较晚（30天），在大脑中发现了显著的放射性标记，其水平与肝脏相当。还向怀孕小鼠静脉注射了氯化蜡，并观察到胎儿对放射性的摄取。当小鼠在怀孕第10天给药时，没有发现特定组织的定位，但在晚期怀孕（第17天）给药后6小时的分布模式与成年小鼠给药24小时后的分布模式相似。/中间链长氯化蜡/

(14)C-Labeled [1-(14)C]polychlorohexadecane (C16;34.1% Cl, CP-ML) was given to C57Bl mice either by gavage (females) or intravenously (both sexes) at a radioactivity level of 370 kBq/animal (10 uCi) (corresponding to 0.44 umol of the chlorinated paraffin). No difference in the distribution patterns was found between the oral and intravenous administration routes. After analysis by autoradiography a high level of radioactivity was found in tissues with a high cell turnover rate and/or high metabolic activity, and lower levels could be seen in the white fat depots. High levels of radioactivity were observed in the liver, kidneys, spleen, bone marrow, brown fat, intestinal mucosa, pancreas, salivary gland and the Harderian gland 24 hr after intravenous injection. After 12 days high levels of radioactivity were seen in the adrenal cortex, abdominal fat and in the bile. Later after injection (30 days), prominent radiolabeling of the brain was found which was as high as in the liver. The chlorinated paraffin was also administered intravenously to pregnant mice, and uptake of radioactivity in the fetuses was observed. When the mice were administered on day 10 of pregnancy no tissue-specific localization was found, but after administration in late pregnancy (day 17) the distribution pattern after 6 hr was similar to that of adult mice when examined 24 hr after administration. /Intermediate chain length chlorinated paraffin/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  TSCA listed

制备方法与用途

根据上述信息，悬浮法生产氯化石蜡70的主要步骤如下：

1. 将石蜡深度氯化而制得氯化石蜡。
2. 预氯化为40%左右的氯化石蜡加入水相溶液。
3. 在100～180℃温度下进行氯化反应。
4. 反应液经过冷却、固化、研磨、洗涤、过滤、干燥得成品。

具体的化学反应方程式为： [ C_nH_{2n+2}（石蜡） + mCl_2（液氯） \rightarrow C_nH_{2n+2-mCl_m}（氯化石蜡） + mHCl（氯化氢气体） ]

图2展示的是悬浮法生产氯化石蜡70的工艺流程图。

此外，该生产方法需要以下原料：

• 石蜡：1吨
• 液氯：约1.44吨

值得注意的是，该过程在较高温度下进行，并且会产生副产物HCl气体。因此，在实际操作中需要注意反应条件控制以及废气处理等问题。

文献信息

• ANTI-GRAFFITI EMULSIONS HAVING A MOISTURE BARRIER PROPERTY
  申请人：Repsol Lubricantes y Especialidades, S.A.

  公开号：EP2565239A2

  公开（公告）日：2013-03-06

  The invention relates to anti-graffiti emulsions comprising at least one type of wax, oil, additives and at least one carrier or excipient. In addition, the invention relates to a method for preparing said anti-graffiti emulsion, a method for applying same and a method for cleaning and recovering the protective effect of graffitied surfaces. Finally, the invention relates to the use of the anti-graffiti emulsions to protect all types of surfaces against graffiti and posters.

  本发明涉及由至少一种蜡、油、添加剂和至少一种载体或赋形剂组成的防涂鸦乳液。此外，本发明还涉及制备所述防涂鸦乳液的方法、涂抹方法以及清洁和恢复涂鸦表面保护效果的方法。最后，本发明还涉及使用防涂鸦乳液来保护各类表面免受涂鸦和海报的侵害。
• Lithium-based grease and preparation method thereof
  申请人：Guangxi LiuGong Machinery Co., Ltd.

  公开号：US11518953B2

  公开（公告）日：2022-12-06

  A lithium-based grease and the preparation method thereof are provided. The raw materials for preparing the lithium-based grease include in parts by weight: 75-88 parts of base oil, 0.5-2.5 parts of antiwear agent, 0.1-1.5 parts of antirust agent, 0.1-1.5 parts of antioxidant, 5-25 parts of lubricant, 5-15 parts of thickening agent, and 0.6-2.0 parts of saponifying agent. The raw materials also include hydroxyl compound-containing modified graphene containing quaternary ammonium salt or aromatic ring. The grease has good colloid stability and mechanical stability, can greatly improve the antiwear property. More than that, the grease has excellent oxidation resistance, and can significantly shorten the reaction time of the saponification, reduce the reaction temperature of the saponification.

  本发明提供了一种锂基润滑脂及其制备方法。制备锂基润滑脂的原料按重量份数包括：基础油 75-88 份、抗磨剂 0.5-2.5 份、防锈剂 0.1-1.5 份、抗氧化剂 0.1-1.5 份、润滑剂 5-25 份、增稠剂 5-15 份和皂化剂 0.6-2.0 份。原材料还包括含有季铵盐或芳香环的羟基化合物改性石墨烯。该润滑脂具有良好的胶体稳定性和机械稳定性，能大大提高抗磨损性能。此外，该润滑脂还具有优异的抗氧化性，并能显著缩短皂化反应时间，降低皂化反应温度。
• ENVIRONMENTALLY FRIENDLY HIGH PRESSURE LUBRICANT ADDITIVE
  申请人：Sloan, Clifford Reginald

  公开号：EP3294848A1

  公开（公告）日：2018-03-21
• LITHIUM-BASED GREASE AND PREPARATION METHOD THEREOF
  申请人：Guangxi LiuGong Machinery Co., Ltd.

  公开号：EP3931289A1

  公开（公告）日：2022-01-05
• ANTI-GRAFFITI EMULSIONS WITH ANTI-HUMIDITY BARRIER CHARACTERISTIC
  申请人：Dabrio Ramos Javier

  公开号：US20130095249A1

  公开（公告）日：2013-04-18

  The present invention relates to anti-graffiti emulsions comprising at least one type of wax, oil, additives and at least one medium or carrier. Additionally, the present invention relates to a process for preparing an anti-graffiti emulsion, a method for application thereof and a method for cleaning and recovering the protective effect of graffiti-painted surfaces. Finally, the invention relates to the use of the anti-graffiti emulsion for any type of surface against graffiti and sticking of posters.

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