全氢化芴 | 5744-03-6

• 物质功能分类: 无机化工 - 无机盐 - 氢化物、氮化物、叠氮化物
• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 中文名称: 全氢化芴
• 中文别名: 全氢芴；十二氢芴(异构体混合物)；十二氢芴
• 英文名称: dodecahydrofluorene
• 英文别名: Perhydrofluoren；perhydrofluorene；2,3,4,4a,4b,5,6,7,8,8a,9,9a-dodecahydro-1H-fluorene
• CAS: 5744-03-6
• 化学式: C₁₃H₂₂
• mdl: MFCD00001161
• 分子量: 178.318
• InChiKey: OLWAZOBRCQWWDB-UHFFFAOYSA-N

物化性质

• 熔点：
  15°C(lit.)
• 沸点：
  253 °C(lit.)
• 密度：
  0.92 g/mL at 25 °C(lit.)
• 闪点：
  148 °F
• 介电常数：
  2.3100000000000001
• 保留指数：
  1466;1489;1430;1455;1442;1464;1447
• 稳定性/保质期：
  <b> <p> </p> </b>

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• 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

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Perhydrofluorene
CAS-No. : 5744-03-6

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Eye irritation (Category 2)
Chronic aquatic toxicity (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
Causes serious eye irritation.
May cause long lasting harmful effects to aquatic life.
Precautionary statement(s)
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Dodecahydrofluorene
Formula : C13H22
Molecular Weight : 178,31 g/mol
Component Concentration
Perhydrofluoren
CAS-No. 5744-03-6 -
EC-No. 227-268-3

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Beware of vapours accumulating to form explosive concentrations.
Vapours can accumulate in low areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 253 °C - lit.
boiling range
g) Flash point 64 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,92 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 6,12
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
Prolonged or repeated exposure may cause allergic reactions in certain sensitive individuals.
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes Causes eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  全氢化芴 在 5%-palladium/activated carbon 作用下， 以 萘烷 为溶剂， 169.84 ℃ 、101.0 kPa 条件下， 反应 19.0h， 生成 芴
  参考文献：
  名称：

  The effect of the N atom on the dehydrogenation of heterocycles used for hydrogen storage

  摘要：

  The effect of the N atom on the hydrogen release rate from heterocyclic compounds was studied by comparing the dehydrogenation rate of dodecahydro-N-ethylcarbazole, dodecahydrocarbazole and dodecahydrofluorene. Over a 5 wt% Pd/C catalyst, hydrogen recovery was fastest (TOF 60 min(-1) at 443 K and 101 kPa) from dodecahydro-N-ethylcarbazole and similar to 3 times faster than that of dodecahydrocarbazole. Dodecahydrofluorene dehydrogenation was the slowest among the compounds examined, with less than 1 wt% H-2 recovered after more than 20 h at 443 K, although selectivity to the completely dehydrogenated product was 95%. Despite catalyst poisoning by the N in dodecahydrocarbazole and its dehydrogenated product, the presence of the N in the heterocycle increased the dehydrogenation reaction rate compared to dodecahydrofluorene, demonstrating that heterocycles are better candidates for H-2 storage than polycycles. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2012.01.013
• 作为产物：
  描述：

  芴 在 10% Pt/activated carbon 、 异丙醇 作用下， 以 水 为溶剂， 反应 24.0h， 以92%的产率得到全氢化芴
  参考文献：
  名称：

  用碳和2-丙醇上的铂结合氢自足芳烃还原成环己烷衍生物

  摘要：

  在不添加易燃氢气的情况下，使用2-碳丙醇-水混合溶剂中的碳载铂在不添加易燃氢气的情况下，将各种芳烃进行了氢化，得到了相应的环己烷衍生物。2-丙醇在碳催化脱氢的基础上，起着基于铂的高效氢源的作用。

  DOI：

  10.1002/adsc.201500263
• 作为试剂：
  描述：

  1-溴-3,5,7-三甲基金刚烷 在 全氢化芴 作用下， 生成 1,3,5-三甲基金刚烷
  参考文献：
  名称：

  Bott,K., Chemische Berichte, 1970, vol. 103, p. 3850 - 3861

  摘要：

  DOI：

文献信息

• Titanium(III)-Oxo Clusters in a Metal–Organic Framework Support Single-Site Co(II)-Hydride Catalysts for Arene Hydrogenation
  作者：Pengfei Ji、Yang Song、Tasha Drake、Samuel S. Veroneau、Zekai Lin、Xiandao Pan、Wenbin Lin

  DOI：10.1021/jacs.7b11241

  日期：2018.1.10

  clusters for supporting single-site catalysts. Herein we report that the Ti8(μ2-O)8(μ2-OH)4 node of the Ti-BDC MOF (MIL-125) provides a single-site model of the classical TiO2 support to enable CoII-hydride-catalyzed arene hydrogenation. The catalytic activity of the supported CoII-hydride is strongly dependent on the reduction of the Ti-oxo cluster, definitively proving the pivotal role of TiIII in the performance

  二氧化钛 (TiO2) 因其独特的强金属-载体相互作用而在化学工业中广泛用作有效的催化剂载体。已经提出了许多建议在宏观水平上合理化这种影响，但由于 TiO2 表面上存在多种催化物质，潜在的分子机制尚不清楚。这一挑战可以通过金属有机框架 (MOF) 来解决，该框架具有明确定义的金属氧/羟基团簇，用于支持单中心催化剂。在此，我们报告了 Ti-BDC MOF (MIL-125) 的 Ti8(μ2-O)8(μ2-OH)4 节点提供了经典 TiO2 载体的单中心模型，以实现 CoII-氢化物催化的芳烃氢化. 负载型 CoII-氢化物的催化活性强烈依赖于 Ti-oxo 簇的还原，最终证明了 TiIII 在负载型催化剂性能中的关键作用。因此，这项工作提供了 Ti-oxo 簇的分子精确模型，用于低估 TiO2 负载的多相催化剂的强金属-载体相互作用。
• Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions
  作者：Tomohiro Maegawa、Akira Akashi、Kiichiro Yaguchi、Yohei Iwasaki、Masahiro Shigetsura、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/chem.200900361

  日期：2009.7.13

  An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H2 pressures (<10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are

  已经开发了基于使用异质铂族催化剂的有效和实用的芳烃加氢方法。Rh / C是最有效的芳环加氢催化剂，可以在中性条件下，在常压至中等H 2压力（<10 atm）下在i PrOH中进行。将各种芳烃（如烷基苯，苯甲酸，吡啶，呋喃）以良好或极好的收率氢化成相应的环己基和杂环化合物。Ru / C的使用比Rh / C便宜，它为氢化包括苯酚在内的芳烃提供了一种有效而实用的方法。在简单过滤后，两种催化剂都可以重复使用数次，而催化活性没有任何重大损失。
• The standard molar enthalpies of formation of some alkyladamantanes
  作者：S.V. Melkhanova,、S.M. Pimenova,、V.P. Kolesov,、A.A. Pimerzin,、V.S. Sarkisova

  DOI：10.1006/jcht.2000.0691

  日期：2000.10

  energies of combustion of three alkyl-derivative of adamantane were measured atT = 298.15 K by static-bomb combustion calorimetry. The standard molar enthalpies of formation in the liquid and gaseous states were obtained from these data. The enthalpies of some reactions of isomerization were calculated from the equilibrium study and compared with the results of calorimetric measurements.

  摘要 采用静弹燃烧量热法在T = 298.15 K时测定了金刚烷的三个烷​​基衍生物的标准燃烧质量能。从这些数据获得液态和气态的标准摩尔生成焓。一些异构化反应的焓是从平衡研究中计算出来的，并与量热测量的结果进行比较。
• Hydrogen Self-Sufficient Arene Reduction to Cyclohexane Derivatives Using a Combination of Platinum on Carbon and 2-Propanol
  作者：Yoshinari Sawama、Misato Mori、Tsuyoshi Yamada、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/adsc.201500263

  日期：2015.11.16

  Various arenes have been hydrogenated using platinum on carbon in a 2-propanol-aqueous mixed solvent at 100 °C without the addition of flammable hydrogen gas to give the corresponding cyclohexane derivatives. 2-Propanol plays a role as an efficient hydrogen source based on the platinum on carbon-catalyzed dehydrogenation.

  在不添加易燃氢气的情况下，使用2-碳丙醇-水混合溶剂中的碳载铂在不添加易燃氢气的情况下，将各种芳烃进行了氢化，得到了相应的环己烷衍生物。2-丙醇在碳催化脱氢的基础上，起着基于铂的高效氢源的作用。
• Acenaphthene and fluorene hydrogenation on industrial aluminum oxide catalysts in a flow system
  作者：E. I. Bagrii、M. V. Tsodikov

  DOI：10.1134/s0965544114020029

  日期：2014.3

  Hydrogenation of the tricyclic aromatic hydrocarbons acenaphthene and fluorene on industrial aluminum oxide catalysts in a flow system has been studied. It has been found that total these hydrocarbons are exhaustively hydrogenated in the presence of a nickel-chromium catalyst at 200°C and a pressure of 100 atm to give isomer mixtures of the corresponding perhydroaromatic hydrocarbons decahydroacenaphthene

  研究了在流动系统中工业氧化铝催化剂上三环芳烃和芴的加氢反应。已经发现，在镍铬催化剂的存在下，在200℃和100atm的压力下，将全部这些烃彻底氢化，得到相应的全氢芳族烃十氢ac和十二氢芴的异构体混合物。所获得的液体产物作为具有增加的密度的烃类燃料的组分可能是令人感兴趣的。已经考虑了获得的立体异构体的某些构象特征。假定十氢ac的一些空间异构体在船形中具有六元环。

表征谱图