苯并[ghi]苝 | 191-24-2

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 苯并[ghi]苝
• 中文别名: 1,12-苯并芘；苯并[ghi]二萘嵌苯；1,12-苯并苝；苯并［g,h,i］芘；苯并(G,H,I)苝
• 英文名称: Benzo[ghi]perylene
• 英文别名: hexacyclo[12.8.0.02,11.03,8.04,21.017,22]docosa-1(14),2(11),3(8),4,6,9,12,15,17(22),18,20-undecaene
• CAS: 191-24-2
• 化学式: C₂₂H₁₂
• 分子量: 276.337
• InChiKey: GYFAGKUZYNFMBN-UHFFFAOYSA-N

物化性质

• 熔点：
  277-279 °C(lit.)
• 沸点：
  >500 °C(lit.)
• 密度：
  1.1847 (estimate)
• 闪点：
  -18 °C
• 溶解度：
  可溶于大多数溶剂 (US EPA, 1985)，包括苯、二氯甲烷和丙酮。
• 物理描述：
  Benzo[ghi]perylene is a colorless to white crystalline solid. Water insoluble.
• 颜色/状态：
  Yellow-green fluorescent leaflets from benzene
• 蒸汽压力：
  1.0X10-10 mm Hg at 25 °C
• 亨利常数：
  3.31e-07 atm-m3/mole
• 稳定性/保质期：
  - 存在于烟气中。 - IARC致癌性评估显示证据不充分，但具有协同致癌活性。
• 分解：
  Hazardous decomposition products formed under fire conditions - Carbon oxides.[Sigma-Aldrich; Safety Data Sheet for Benzo
• 汽化热：
  96.1 kJ/mol (323-473 K)
• 相对蒸发率：
  Evaporation at 20 °C is negligible
• 碰撞截面：
  154 Ų [M*]+; 155.5 Ų [M+H]+
• 保留指数：
  3144;3124;3115;3122;3124;3137;3185;3185;3124;3144;3185;3140.8;3173.9;501.3;501.3;502.9;502.8;503.1;501.5

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

使用最近开发的代谢毒性筛选阵列和生物胶体反应器-液相色谱-串联质谱（LC-MS/MS）方法，两者都采用DNA和人类代谢酶的薄膜，我们证明了代谢激活的苯并[ghi]苝（B[ghi]P）对DNA的相对低反应性。电光学毒性筛选阵列显示，B[ghi]P代谢物对DNA的损伤速率比苯并[a]芘（B[a]P）低3倍，后者的代谢物对DNA损伤有强烈的、已被充分理解的趋势。使用96孔板中涂有微囊酶的磁珠生物胶体反应器进行的代谢研究显示，细胞色素P450 1A1和1B1对B[ghi]P和B[a]P转化提供了高活性。与已发布的结果一致，B[ghi]P的主要代谢涉及3,4和11,12位的氧化，导致形成B[ghi]P 3,4-氧化物和B[ghi]P 3,4,11,12-双氧化物。合成了B[ghi]P 3,4-氧化物，并与脱氧腺苷的N6和N7位以及脱氧鸟苷的N2位发生反应。B[ghi]P 3,4-氧化物在水解上不稳定，会转化为3,4-二醇或转化为3-或4-羟基B[ghi]P。对涂有DNA和人类酶的磁珠生物胶体反应器颗粒的反应产物进行LC-MS/MS分析，首次揭示了主要的DNA加合物是由B[ghi]P 3,4,11,12-双氧化物和脱氧鸟苷之间的反应产生的。结果还表明，与B[a]P相比，B[ghi]P代谢物的主要DNA加合物的形成速率降低了5倍。总的来说，电光学阵列和生物胶体反应器-LC-MS/MS的结果一致表明，B[ghi]P的人类遗传毒性风险低于B[a]P。

... Using recently developed metabolic toxicity screening arrays and a biocolloid reactor-LC-MS/MS approach, both featuring films of DNA and human metabolic enzymes, we demonstrated the relatively low reactivity of metabolically activated benzo[ghi]perylene (B[ghi]P) toward DNA. Electro-optical toxicity screening arrays showed that B[ghi]P metabolites damage DNA at a 3-fold lower rate than benzo[a]pyrene (B[a]P), whose metabolites have a strong and well-understood propensity for DNA damage. Metabolic studies using magnetic bead biocolloid reactors coated with microsomal enzymes in 96-well plates showed that cyt P450s 1A1 and 1B1 provide high activity for B[ghi]P and B[a]P conversion. Consistent with published results, the major metabolism of B[ghi]P involved oxidations at 3,4 and 11,12 positions, leading to the formation of B[ghi]P 3,4-oxide and B[ghi]P 3,4,11,12-bisoxide. B[ghi]P 3,4-oxide was synthesized and reacted with deoxyadenosine at N6 and N7 positions and with deoxyguanosine at the N2 position. B[ghi]P 3,4-oxide is hydrolytically unstable and transforms into the 3,4-diol or converts to 3- or 4-hydroxy B[ghi]P. LC-MS/MS of reaction products from the magnetic biocolloid reactor particles coated with DNA and human enzymes revealed for the first time that a major DNA adduct results from the reaction between B[ghi]P 3,4,11,12-bisoxide and deoxyguanosine. Results also demonstrated 5-fold lower formation rates of the major DNA adduct for B[ghi]P metabolites compared to B[a]P. Overall, results from both the electro-optical array and biocolloid reactor-LC-MS/MS consistently suggest a lower human genotoxicity profile of B[ghi]P than B[a]P.

来源:Hazardous Substances Data Bank (HSDB)

代谢

致瘤多环芳烃（PAH），例如苯并[a]芘（BaP），含有一个包括一个并苯环的湾区。苯并[ghi]苝（BghiP）代表了不含这种“经典”湾区的一组PAH，因此不能像BaP那样代谢转化为湾区二氢二醇环氧化合物，后者被认为是PAH的最终诱变和致瘤代谢物。BghiP在经过3-甲基胆蒽处理的CD大鼠的微粒体后肝部分代谢激活后，在鼠伤寒沙门氏菌的TA98（1.3 his(+)-回复突变菌落/nmol）和TA100（4.3 his(+)-回复突变菌落/nmol）菌株中表现出细菌诱变性。用1,1,1-三氯-2-丙烯氧化物抑制微粒体环氧化酶（mEH）几乎使BghiP在TA98中的细菌诱变性增加了4倍，表明芳环氧化物是最终的诱变剂。为了证实这一假设，对BghiP的生物转化进行了阐明。将BghiP与经Aroclor 1254处理的CD大鼠的肝微粒体一起孵化，产生了17种可被乙酸乙酯提取的代谢产物。通过色谱、光谱和生化方法的结合，确定了12种代谢物。BghiP的微粒体生物转化通过两条途径进行：途径I从7-位的单加氧酶攻击开始，形成7-酚，然后转化为7,8-和7,10-二酚，再氧化为7,8-和7,10-醌。在途径II中，BghiP的K区域依次转化为芳环氧化物，产生间接识别的3,4-氧化物和3,4,11,12-双氧化物。3,4-氧化物的酶促水解导致形成反式-3,4-二氢二醇，后者被氧化为3,4-醌。同样，反式-3,4-反式-11,12-双二氢二醇和反式-3,4-二氢二醇11,12-醌是由3,4,11,12-双氧化物产生的。反式-3,4-二氢二醇和反式-3,4-反式-11,12-双二氢二醇分别优先形成R,R和R,R,R,R对映体。3,4,11,12-双氧化物的内在细菌诱变性相当低，几乎无法解释mEH抑制后BghiP的细菌诱变性显著增加。因此，我们认为3,4-氧化物作为BghiP的最终诱变代谢物更为重要。

Carcinogenic polycyclic aromatic hydrocarbons (PAH), e.g., benzo[a]pyrene (BaP), possess a bay region comprising an ortho-fused benzene ring. Benzo[ghi]perylene (BghiP) represents the group of PAHs lacking such a "classic" bay region and hence cannot be metabolically converted like BaP to bay region dihydrodiol epoxides considered as ultimate mutagenic and carcinogenic metabolites of PAH. BghiP exhibits bacterial mutagenicity in strains TA98 (1.3 his(+)-revertant colonies/nmol) and TA100 (4.3 his(+)-revertant colonies/nmol) of Salmonella typhimurium after metabolic activation by the postmitochondrial hepatic fraction of CD rats treated with 3-methylcholanthrene. Inhibition of microsomal epoxide hydrolase (mEH) with 1,1,1-trichloro-2-propene oxide raised the bacterial mutagenicity of BghiP in TA98 almost 4-fold indicating arene oxides as ultimate mutagens. To confirm this assumption, the biotransformation of BghiP was elucidated. Incubation of BghiP with liver microsomes of CD rats treated with Aroclor 1254 yielded 17 ethyl acetate extractable metabolic products. Twelve metabolites were identified by a combination of chromatographic, spectroscopic, and biochemical methods. The microsomal biotransformation of BghiP proceeds by two pathways: Pathway I starts with the monooxygenase attack at the 7-position leading to the 7-phenol, which is transformed to the 7,8- and 7,10-diphenols followed by oxidation to the 7,8- and 7,10-quinones. On pathway II, the K regions of BghiP are successively converted to arene oxides yielding the indirectly identified 3,4-oxide and the 3,4,11,12-bisoxides. Enzymatic hydrolysis of the 3,4-oxide leads to the trans-3,4-dihydrodiol, which is oxidized to the 3,4-quinone. Similarly, the trans-3,4-trans-11,12-bisdihydrodiols and the trans-3,4-dihydrodiol 11,12-quinone are generated from the 3,4,11,12-bisoxides. The trans-3,4-dihydrodiol and the trans-3,4-trans-11,12-bisdihydrodiols are preferentially formed as R,R and R,R,R,R enantiomers, respectively. The intrinsic bacterial mutagenicity of the 3,4,11,12-bisoxides is rather low and hardly explains the strong increase in bacterial mutagenicity of BghiP after inhibition of mEH. Thus, we believe that the 3,4-oxide plays a more important role as the ultimate mutagenic metabolite of BghiP.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在用未经处理的大鼠肝微粒体进行孵化后，未发现来自苯并(ghi)芘的代谢物。

After incubation with liver microsomes from nonpretreated rats, no metabolites were found from benzo(ghi)perylene.

来源:Hazardous Substances Data Bank (HSDB)

代谢

15种多环芳烃的遗传毒性通过使用中国仓鼠V79肺成纤维细胞作为靶细胞，采用碱性彗星试验进行了测定。这些细胞缺乏将多环芳烃转化为DNA结合代谢物的酶。在没有外部代谢激活的情况下，11种多环芳烃，即苯并[a]芘（BaP）、苯并[a]蒽、7,12-二甲基苯并[a]蒽、3-甲基胆蒽、荧蒽、安丹特、11H-苯并[b]荧烷、二苯并[a,h]蒽、芘、苯并[ghi]苝和苯并[e]芘引起了DNA链断裂，而萘、蒽、菲和萘嵌苯则没有活性。当彗星试验在黑暗中进行，或者使用黄色荧光灯照明时，这11种多环芳烃的DNA损伤效果消失了。白色荧光灯在334.1、365.0、404.7和435.8 nm处表现出汞光谱线的发射最大值。在黄色荧光灯的情况下，这些发射消失了。显然，在标准实验室照明下，许多多环芳烃被光激活，产生DNA损伤物种。在利用这些化合物引发皮肤癌时，应考虑到多环芳烃的这一特性。

The genotoxicity of 15 polycyclic aromatic hydrocarbons was determined with the alkaline version of the comet assay employing V79 lung fibroblasts of the Chinese hamster as target cells. These cells lack the enzymes necessary to convert PAHs to DNA-binding metabolites. ... 11 PAHs, i.e., benzo[a]pyrene (BaP), benz[a]anthracene, 7,12-dimethylbenz[a]anthracene, 3-methylcholanthrene, fluoranthene, anthanthrene, 11H-benzo[b]fluorene, dibenz[a,h]anthracene, pyrene, benzo[ghi]perylene and benzo[e]pyrene caused DNA strand breaks even without external metabolic activation, while naphthalene, anthracene, phenanthrene and naphthacene were inactive. When the comet assay was performed in the dark or when yellow fluorescent lamps were used for illumination the DNA-damaging effect of the 11 PAHs disappeared. White fluorescent lamps exhibit emission maxima at 334.1, 365.0, 404.7, and 435.8 nm representing spectral lines of mercury. In the case of yellow fluorescent lamps these emissions were absent. Obviously, under standard laboratory illumination many PAHs are photo-activated, resulting in DNA-damaging species. This feature of PAHs should be taken into account when these compounds are employed for the initiation of skin cancer. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

多环芳烃（PAHs）的代谢发生在所有组织中，通常通过细胞色素P-450及其相关酶进行。多环芳烃被代谢成反应性中间体，其中包括环氧中间体、二氢二醇、酚、醌以及它们的各种组合。酚、醌和二氢二醇都可以与葡萄糖苷酸和硫酸酯结合；醌还可以形成谷胱甘肽结合物。

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

鉴定和使用：苯并(ghi)芘（BghiP）是一种固体。它以小量用于科学研究。多环芳烃（PAHs）是一组在煤炭、石油、天然气、木材、垃圾或其他有机物质（如烟草和炭烤肉）不完全燃烧时形成的化学物质。人类暴露和毒性：在人类细胞中，BghiP可以激活芳基烃受体（AhR）和细胞色素CYP4B1的过度表达，而这些效果可以通过AhR受体拮抗剂来减轻。BghiP代表了一组缺乏“经典”湾区结构的多环芳烃，因此它不能被代谢转化为被认为是多环芳烃最终诱变和致癌代谢物的湾区二氢二醇环氧化物。实验结果表明，B[ghi]P的人类遗传毒性特征低于苯并[a]芘。动物研究：当给予大鼠5毫克的剂量时，苯并(ghi)芘在呼吸道中未表现出致癌效果。分析了BghiP对新生大鼠皮肤和肝脏芳基烃羟化酶以及7-乙氧基香豆素-O-脱乙基酶活性的诱导作用。单次局部应用导致肝脏酶的诱导，而未对皮肤酶产生效果。BghiP在经过代谢激活后在鼠伤寒沙门氏菌的TA98和TA100菌株中表现出细菌诱变性。生态毒性研究：BghiP导致幼年银鸥（Larus argentatus）生长迟缓和肾上腺及鼻腺重量增加。

IDENTIFICATION AND USE: Benzo(ghi)perylene (BghiP) is a solid. It is used in small amounts for scientific research. Polycyclic aromatic hydrocarbons (PAHs) are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. HUMAN EXPOSURE AND TOXICITY: In human cells BghiP can activate the overexpression of aryl hydrocarbon receptor (AhR) and cytochrome CYP4B1, and the effects are abated by the AhR receptor antagonist. BghiP represents the group of PAHs lacking a "classic" bay region and hence it cannot be metabolically converted to bay region dihydrodiol epoxides considered as ultimate mutagenic and carcinogenic metabolites of PAH. Experimental results demonstrate lower human genotoxicity profile of B[ghi]P than for benzo[a]pyrene. ANIMAL STUDIES: Benzo(ghi)perylene showed no tumorigenic effect in the respiratory tracts of rats when given at doses of 5 mg. BghiP was analyzed for induction effect on skin and liver aryl hydrocarbon hydroxylase and 7-ethoxycoumarin o-deethylase activities in neonatal rats. A single topical application caused induction of liver enzymes without producing effects on skin enzymes. BghiP exhibits bacterial mutagenicity in strains TA98 and TA100 of Salmonella typhimurium after metabolic activation. ECOTOXICITY STUDIES: BghiP was responsible for retardation of growth and increases in adrenal and nasal gland weight in nestling herring gulls (Larus argentatus).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

多环芳烃（PAHs）能够与血液中的蛋白质，如白蛋白结合，从而在体内进行传输。许多多环芳烃通过与芳烃受体或甘氨酸N-甲基转移酶蛋白结合，诱导细胞色素P450酶的表达，尤其是CYP1A1、CYP1A2和CYP1B1。这些酶将多环芳烃代谢成其有毒的中间产物。多环芳烃的反应性代谢物（环氧化物中间体、二氢二醇、酚、醌及其各种组合）与DNA和其他细胞大分子共价结合，启动突变和致癌过程。

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

分类：D；无法归类为人类致癌性。分类依据：基于没有人类数据和来自肺植入、皮肤涂敷和皮下注射生物检测的不充分动物数据。人类致癌性数据：无。动物致癌性数据：不充分。

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Based on no human data and inadequate animal data from lung implant, skin-painting and subcutaneous injection bioassays. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Inadequate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

总评：第3组：该物质对人类致癌性无法分类。

OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：苯并[ghi]苝

IARC Carcinogenic Agent:Benzo[ghi]perylene

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

描述了一种分析程序，包括提取多环芳烃（PAH），包括苯并（ghi）苝，以及从尿液中提取多环芳烃代谢物，将代谢物还原为原始的多环芳烃，随后通过高效液相色谱（HPLC）进行分析。非吸烟者尿液中11种多环芳烃总和的平均值为1.1微克/摩尔肌酐。吸烟者尿液中多环芳烃的总和显著更高。在铝还原工人的尿液中发现了多环芳烃水平的升高。

An analytical procedure is described which includes extraction of polycyclic aromatic hydrocarbons (PAH), including benzo(ghi)perylene, and polycyclic aromatic hydrocarbons metabolites from urine, reduction of metabolites to the original polycyclic aromatic hydrocarbons and subsequent analysis by HPLC. The mean value of the sum of the 11 polycyclic aromatic hydrocarbons in non smoker's urine was 1.1 ug/mmol creatinine. The sum of polycyclic aromatic hydrocarbons in smoker's urine was significantly higher. Increased levels of PAH were found in the urine of aluminum reduction workers.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

芘（ghi）被胃肠道和肺部迅速吸收。一般来说，多环芳烃的脂溶性很高，能够穿越上皮细胞膜。

... Benzo(ghi)perylene is absorbed readily from the gastrointestinal tract and lung. In general, polycyclic aromatic hydrocarbons are highly lipid soluble and can pass across epithelial membranes.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  9
• 危险品标志：
  Xn,F,N
• 安全说明：
  S36/37,S45
• 危险类别码：
  R40
• WGK Germany：
  2,3
• 海关编码：
  2902909090
• 危险品运输编号：
  UN 3077 9/PG 3
• RTECS号：
  DI6200500
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P501,P273,P260,P270,P264,P280,P391,P314,P337+P313,P305+P351+P338,P301+P312+P330
• 危险性描述：
  H302,H319,H372,H410
• 储存条件：
  本品应密封保存。

SDS

国标编号:
ＣＡＳ:	191-24-2
中文名称:	苯并[ghi]苝
英文名称:	Benzo[ghi]Pyrene；BPR
别 名:	多环芳烃(PAH)；稠环芳烃
分子式:	C 22 H 12
分子量:	276
熔 点:	222～223℃
密 度:	1.35
蒸汽压:
溶解性:	不溶于水，表面活性剂可增加其水中溶解度
稳定性:
外观与性状:	苯中析出叶状晶体，呈鲜艳黄绿色荧光
危险标记:
用 途:	本品在工业上无生产和使用价值，一般只作为生产过程中形成的副产物随废气排放

2.对环境的影响
毒性毒理：人们对环境中多环芳烃的毒性的全面研究还比较少。在环境中很少遇到单一的多环芳烃(PAH)，而PAH混合物中可能发生很多相互作用。PAH化合物中有不少是致癌物质，但并非直接致癌物，必须经细胞微粒中的混合功能氧化酶激活后才具有致癌性。第一步为氧化和羟化作用，产生的环氧化物或酚类可能再以解毒反应生成葡萄糖苷、硫酸盐或谷胱甘肽结合物，但某些环氧化物可能代谢成二氢二醇，它依次通过结合而生成可溶性的解毒产物或氧化成二醇-环氧化物，这后一类化合物被认为是引起癌症的终致癌物。PAH的化学结构与致癌活性有关，分子结构的改变，常引起致癌活性显著变化。在苯环骈合类的多环芳烃中有致癌活性的只是4至6环的环芳烃中的一部分。苯并[ghi]北的相对致癌性较强。

代谢、降解、蓄积：PAH具有高度的脂溶性，易于经哺乳动物的内脏和肺吸收，能迅速地从血液和肝脏中被清除，并广泛分布于各种组织中，特别倾向于分布在体脂中。虽然PAG有高度的脂溶性，但是在动物或人的脂肪中几乎无生物蓄积作用的倾向，主要因为PAH能迅速和广泛地被代谢，代谢产物主要以水溶性化合物从尿和粪中排泄。在环境大气和水体中的PAH受到足够能量的阳光中紫外线的照射时会发生光解作用，土壤中的某些微生物可以使PAH降解，但分子量较大的苯并[ghi]北的光解、水解和生物降解是很微弱的。

迁移、转化：环境中的PAH主要来源于煤和石油的燃烧，也可来自垃圾焚烧或森林大火。其生成量同燃烧设备和燃烧温度等因素有关，如大型锅炉生成量很低，家用煤炉生成量很高。柴油和汽油机的排气中，以及炼油厂、煤焦油加工厂和沥青加工厂等排出的废气和废水中都含有PAH。PAH还存在于熏制的食物和香烟烟雾中。PAH大多吸附在大气和水中的微小颗粒物上，大气中的PAH为通过沉降和降水而污染土壤和地面水，研究表明，除了工业排污外，大气降水是径流排水中PAH的主要来源。由于PAH的水中溶解度低和亲脂性较强，因此该类化合物易于从不中分配到沉积物、有机质及生物体内，其结果使水中PAH的浓度较低，而在沉积物中残留浓度较高。

3.现场应急监测方法


4.实验室监测方法
高效液相色谱法(GB13198-91，水质)
气相色谱法《空气中有害物质的测定方法》(第二版)，杭士平编
气相色谱法《固体废弃物试验分析评价手册》中国环境监测总站等译

5.环境标准
欧洲共同体(1975)饮用水 0.0001mg/L(PAH)

6.应急处理处置方法
处置：由于PAH与悬浮固体紧密结合，所以可以通过采用水处理措施降低浊度来保证PAH含量降至最低水平。

预防措施：由于PAH污染人类环境的范围很广，产生污染的具体原因很多，所以预防措施涉及的工艺操作过程，废水废气的综合利用和处理，自来水的净化和消毒，改进汽油燃烧过程，改良食品烟熏剂，提供间接烘烤，养成个人卫生习惯(不吸烟或少吸烟)等。

制备方法与用途

化学反应

苯并(G,H,I)苝与溴在铁的存在下于二氯甲烷中反应，可以得到3,8-二溴苯并[G,H,I]苝。

制备

苯并(G,H,I)苝可通过将苝和硝基乙烯在175 °C的1,2-二氯苯中反应制得。

用途

n沟道有机半导体。

类别

有毒物品

可燃性危险特性

可燃；燃烧会产生刺激烟雾

储运特性

通风、低温干燥

灭火剂

干粉、泡沫、沙土、二氧化碳、雾状水

反应信息

• 作为反应物：
  描述：

  苯并[ghi]苝 在 copper(l) chloride 氧气 、 甲烷 作用下， 反应 2.0h， 生成 1,3,5,8-四氯萘
  参考文献：
  名称：

  De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes

  摘要：

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

  DOI：

  10.1021/es980857k
• 作为产物：
  描述：

  benzo[ghi]perylene-1,2-dicarboxylic anhydride 在 铜 作用下， 以 喹啉 为溶剂， 反应 5.0h， 生成 苯并[ghi]苝
  参考文献：
  名称：

  Fluorescent coronene monoimide gels via H-bonding induced frustrated dipolar assembly

  摘要：

  据报道，基于新型冠烯单亚胺（CMI）凝胶的两阶段自组装可使聚集状态下的单体发射重现。这一过程归因于氢键作用下的受挫头顶双极组装。

  DOI：

  10.1039/c1cc14990c

文献信息

• Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes
  作者：Harish R. Talele、Anju R. Chaudhary、Parthiv R. Patel、Ashutosh V. Bedekar

  DOI：10.3998/ark.5550190.0012.902

  日期：——

  developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number

  已开发出一种用于合成菲和螺旋烯的二苯乙烯光脱氢环化的改进程序。该过程涉及使用 THF 作为碘介导的光脱氢环化过程中产生的氢碘酸的清除剂。由于与环氧丙烷相比，THF的沸点更高、成本更低且易于获得，因此使用THF是有利的。该方法用于合成多种菲和螺旋。
• 유기 화합물 및 이를 사용하여 형성된 3차원 유기 구조체
  申请人：IUCF-HYU (Industry-University Cooperation Foundation Hanyang University) 한양대학교 산학협력단(220040114276) BRN ▼206-82-07306

  公开号：KR20180043221A

  公开（公告）日：2018-04-27

  3차원 유기 구조체를 제공한다. 상기 유기 구조체는 비공유 결합에 의해 자기조립된 다수 개의 유기 분자들을 포함한다. 각 유기 분자는 방향족 고리와 상기 방향족 고리의 치환가능한 위치들 중 바로 인접한 위치들에 각각 결합된 치환기들의 제1 쌍과 나머지 치환가능한 위치들 중 바로 인접한 위치들에 각각 결합된 치환기들의 제2 쌍을 구비한다. 상기 유기 분자들은 상기 치환기들의 제1 쌍과 제2 쌍 사이의 반 데르 발스(Van Der Waals) 상호작용, 런던 분산력(London dispersion interaction) 또는 수소 결합(hydrogen bonding)과 방향족 고리들 사이의 파이-파이 상호작용에 의해 자기 조립된다.

  提供三维有机结构。 该有机结构包括通过非共价键合自组装而成的多个有机分子。 每个有机分子都具有第一对取代基和第二对取代基，它们分别与芳香环和相邻的取代位点上的取代基结合。 这些有机分子通过取代基之间的范德华力、伦敦分散作用或氢键以及芳香环之间的π-π相互作用进行自组装。
• ORGANIC COMPOUND, THREE-DIMENSIONAL ORGANIC FRAMEWORK FORMED BY USING ORGANIC COMPOUND, SEPARATION SIEVE AND OPTICAL LAYER, WHICH COMPRISE ORGANIC FRAMEWORK, AND OPTICAL DEVICE COMPRISING OPTICAL LAYER AS OPTICAL AMPLIFICATION LAYER
  申请人：INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY

  公开号：US20190031586A1

  公开（公告）日：2019-01-31

  An organic compound, a three-dimensional organic structure formed by using the organic compound, a separation sieve and an optical layer having the organic structure, and an optical device having the optical layer as an optical amplification layer are provided. The organic structure includes a plurality of organic molecules self-assembled by non-covalent bonding. Each of the unit organic molecules has an aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of remaining substitutable positions of the aromatic ring. The unit organic molecules are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding between the first and the second pairs of the substituents and by pi-pi interactions between the aromatic rings.

  提供一种有机化合物，通过使用该有机化合物形成的三维有机结构、分离筛和具有该有机结构的光学层，以及具有光学层作为光学放大层的光学器件。该有机结构包括通过非共价键自组装的多个有机分子。每个单元有机分子具有芳香环，第一对取代基连接到芳香环的可取代位置的相邻位置，第二对取代基连接到芳香环的剩余可取代位置的相邻位置。单元有机分子通过范德华力相互作用、伦敦分散相互作用或氢键作用于第一和第二对取代基之间的π-π相互作用而自组装。
• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• Synthesis of Derivatives of Phenanthrene and Helicene by Improved Procedures of Photocyclization of Stilbenes
  作者：Harish R. Talele、Monik J. Gohil、Ashutosh V. Bedekar

  DOI：10.1246/bcsj.82.1182

  日期：2009.9.15

  An improved method has been developed for photocyclization of stilbene to construct phenanthrenes and benzo[c]phenanthrenes. This reaction is promoted by iodine while tetrahydrofuran is used as an ...

  已经开发了一种改进的方法，用于二苯乙烯的光环化以构建菲和苯并 [c] 菲。该反应由碘促进，而四氢呋喃用作...

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