Methylcyclohexane – Wikipedia

Methylcyclohexane
Identification
UICPA name	methylcyclohexane
N O CAS	108-87-2
N O Echa	100.003.296
N O THIS	203-624-3
Pubchem	7962
SMILES
Inches	Inches: 3D view Inchi = 1S/C7H14/C1-7-5-3-2-4-6-7/H7H, 2-6H2,1H3
Chemicals
Formula	C 7 H 14 [Isomers]
Molar mass [ first ]	98,186 1 ± 0.006 6 g/mol C 85,63 %, H 14,37 %,
Physical properties
T° fusion	−126,55 °C [ 2 ]
T° boiling	100.85 °C [ 2 ]
Solubility parameter Δ	7.8 cal 1/2 · cm -3/2 ( 25 °C ) [ 3 ]
Critical point	299.85 °C , 34.8 bar , 0.369 l · mol -first [ 2 ]
Thermochimie
S 0 liquid, 1 bar	247.9 J · K -first · mol -first [ 2 ]
D f H 0 liquid	−190,2 kJ · mol -first [ 2 ]
D fus H°	6,750 5 kJ · mol -first To −126,57 °C [ 2 ]
D vap H°	35 kJ · mol -first [ 2 ]
C p	184,38 J · K -first · mol -first To 25 °C [ 2 ] after-content-x4 equation [ 4 ] : ${displaystyle C_{P}=(4.296)+(4.2716E-1)times T+(2.1058E-4)times T^{2}+(-3.9987E-7)times T^{3}+(1.3121E-10)times T^{4}}$ Thermal capacity of gas in J · Mol -first ·K -first and Kelvin temperature, from 200 to 1,500 K. Calculated values: 140,812 J · mol -first ·K -first at 25 ° C. T (K) T (°C) Cp ${displaystyle ({tfrac {J}{kmoltimes K}})}$ Cp ${displaystyle ({tfrac {J}{kgtimes K}})}$ 200 −73,15 95 162 969 286 12,85 135 212 1 377 330 56,85 155 377 1 582 373 99,85 174 713 1 779 416 142,85 193 579 1 972 460 186,85 212 301 2 162 503 229,85 229 946 2 342 546 272,85 246 876 2 514 590 316,85 263 398 2 683 633 359,85 278 710 2 839 676 402,85 293 160 2 986 720 446,85 307 026 3 127 763 489,85 319 662 3 256 806 532,85 331 387 3 375 850 576,85 342 448 3 488 T (K) T (°C) Cp after-content-x4 ${displaystyle ({tfrac {J}{kmoltimes K}})}$ Cp ${displaystyle ({tfrac {J}{kgtimes K}})}$ 893 619,85 352 360 3 589 936 662,85 361 412 3 681 980 706,85 369 823 3 767 1 023 749,85 377 262 3 842 1 066 792,85 383 990 3 911 1 110 836,85 390 211 3 974 1 153 879,85 395 725 4 030 1 196 922,85 400 775 4 082 1 240 966,85 405 569 4 131 1 283 1 009,85 410 005 4 176 1 326 1 052,85 414 322 4 220 1 370 1 096,85 418 756 4 265 1 413 1 139,85 423 257 4 311 1 456 1 182,85 428 082 4 360 1 500 1 226,85 433 530 4 415
PCI	−4 565,29 kJ · mol -first [ 2 ]
Precautions
Simdut [ 5 ]
B2,
NFPA 704 [ 6 ]
Directive 67/548/EEC [ 7 ]
Index number : 601-018-00-7 Classification : F; R11 – Xn; R65 – Xi; R38 – R67 – N; R51-53 Symbols : Xn : Harmful F : Easily flammable N : Dangerous for the environment Phrases R : R11 : Easily flammable. R38 : Irritating for the skin. R65 : Harmful: can cause damage to the lungs in case of ingestion. R67 : The inhalation of vapours can cause tiredness and dizziness. R51 / 53 : Toxic to aquatic organizations, can cause long -term harmful effects for the aquatic environment. Phrases S : S2 : Keep children out of reach. S9 : Keep the recipient in a well ventilated place. S16 : Keep away from any flame or source of sparks – Do not smoke. S33 : Avoid the accumulation of electrostatic charges. S61 : Avoid release into the environment. Consult special instructions/security data sheet. S62 : In case of ingestion, do not make vomit. Consult a doctor immediately and show him the packaging or label.
Transport [ 8 ]
Code Kemler : 33 : very flammable liquid (ignition point lower than 23 °C ) UN number: 2296 : Methylcyclohexane Class: 3 Label : 3 : Flammable liquids Packaging : Packaging group II : moderately dangerous materials;
IS units and CNTP , unless otherwise stated.
modifier

The methylcyclohexane is a cyclic hydrocarbon, a brute formula cycloalcan C ₇ H _{14 . Il se présente comme un liquide incolore dégageant une faible odeur de benzène.}

It is an ecotoxic product when it is spread in the environment ^{[ 9 ]}

It can be obtained in particular by hydrogen of toluene.

Methylcyclohexane is

• A base for organic synthesis
• A solvent of cellulose ethers.
• A fuel component for aviation
• A correction fluid component.

The methylcyclohexan monosubstituted has a methyl substitute for a carbon atom of the cyclohexane cycle.

Like all substituted cyclohexans, its shape can quickly switch between two conformations. However, a methylcyclohexan monosubstituted with a methyl group in the equatorial position (more stable) is the form almost exclusively present, rather than anxial (unstable).

This molecule (methylcyclohexane) is part of a group of fuels that have recently been used as mixtures components that can be substituted for conventional kerosenes ^{[ ten ]} . The chemical analysis of jet A (jet plane fuel) shows a high cycloparaffin content; Methylcyclohexane is one of the hydrocarbons used as a jet a to imitate this strong presence of cycloparaffins and the chemical behavior of the fuel.

Its degree of toxicity is still imperfectly known (it causes drowsiness ^{[ 11 ]} and dizziness ^{[ 11 ]} and can be fatal in case of ingestion (it attacks the lungs ^{[ 11 ]} ) or penetration in the respiratory tract ^{[ 11 ]} , but various studies have also focused on:

• Its possibly reprotoxic character for workers exposed to it was evaluated by a study in rats ^{[ twelfth ]}
• The subchronistic effects of an exhibition (from sprague-Dawley rats) by inhalation and exposure of the whole body to methylcyclohexan vapor 6 hours per day, 5 days/week for 13 weeks ^{[ 13 ]} . The clinical effects were an abnormal salivation and friction behavior (pruritus?) Observed in both sexes exposed to 5870 ppm, with an increase in the weight of the liver (in both sexes) and kidneys (in females only), by report to a control group. The observed harmful effect concentration was in this case of 1300 ppm/6 h/day (in rats).
• Its metabolization by the kidney after absorption by food has been studied in laboratory rat; According to the histopathological examination, it degrades the kidney tissues relatively little (to the dosage of the experience) ^{[ 14 ]} . We also searched what his metabolites in human urine were workers of a shoe factory exposed to this product and other solvents ^{[ 15 ]} .

Ecotoxicologie [ modifier | Modifier and code ]

It is classified dangerous for the aquatic environment ^{[ 11 ]} ; very toxic for fish ^{[ 11 ]} and toxic to other aquatic organizations ^{[ 11 ]} .

In early 2014, a leak of about 19 000 L of methylcyclohexan which occurred in the factories of “Freedom Industries” polluted the Elk river, upstream (more than 1.5 km ) of the pumping place of the Compagnie des Eaux which serves several counties deprived of around 300,000 inhabitants of Charleston (Virginie-Western, United States), for more than 5 days (they were asked not to drink tap water neither cook nor even brush your teeth with it) ^{[ 16 ]} . This product was in this case used to treat coal ^{[ 16 ]} And “Contaminated water has a smell of licorice or anise” ^{[ 16 ]} .

Bibliography [ modifier | Modifier and code ]

• (in) Beckett, C. W., Pitzer, K. S., & Spitzer, R. (1947). The Thermodynamic Properties and Molecular Structure of Cyclohexane, Methylcyclohexane, Ethylcyclohexane and the Seven Dimethylcyclohexanes1. Journal of the American Chemical Society, 69(10), 2488-2495 ( résumé ).
• (in) Dobashi, T., Nakata, M., & Kaneko, M. (1980). Coexistence curve of polystyrene in methylcyclohexane. I. Range of simple scaling and critical exponents. The Journal of Chemical Physics, 72, 6685 ( résumé ).
• (in) Rao, M. V. P., & Naidu, P. R. (1974). Excess volumes of binary mixtures of alcohols in methylcyclohexane. Canadian Journal of Chemistry, 52(5), 788-790 ( résumé )
• (in) Ribeiro, F. H., Dalla Betta, R. A., Boudart, M., Baumgartner, J., & Iglesia, E. (1991). Reactions of neopentane, methylcyclohexane, and 3, 3-dimethylpentane on tungsten carbides: The effect of surface oxygen on reaction pathways. Journal of Catalysis, 130(1), 86-105 ( http://www.sciencedirect.com/science/article/pii/002195179190094k résumé]).
• (in) Anet, F. A., Bradley, C. H., & Buchanan, G. W. (1971). Direct detection of the axial conformer of methylcyclohexane by 63.1 MHz carbon-13 nuclear magnetic resonance at low temperatures. Journal of the American Chemical Society, 93(1), 258-259 ( résumé )
• (in) Jonas, J. D. S. G., Hasha, D., & Huang, S. G. (1979). Self‐diffusion and viscosity of methylcyclohexane in the dense liquid region. The Journal of Chemical Physics, 71, 3996 ( résumé )
• (in) Pitz, W., Naik, C. V., Mhaoldúin, T. N., Westbrook, C. K., Curran, H. J., Orme, J. P., & Simie, J. M. (2007). Modeling and Experimental Investigation of Mehylcyclohexane Iignation in A Rapid Compression Machine. Proceedings of the Combustion Institute, 31(1), 267-275 ([PITZ, W. J., NAIK, C. V., mhaoldúin, T. N., Westbrook, C. K., Curran, H. J., Orme, J. P. (2007). Modeling and experimental investigation of methylcyclohexane ignition in a rapid compression machine . Proceedings of the Combustion Institute, 31(1), 267-275. ( résumé )
• (in) Orme, J. P., Curran, H. J., & Simmie, J. M. (2006). Experimental and modeling study of methyl cyclohexane pyrolysis and oxidation. The Journal of Physical Chemistry A, 110(1), 114-131. (| http://pubs.acs.org/doi/abs/10.1021/jp0543678 résumé])
• (in) Nakamura, T., Makino, T., Sugahara, T., & Ohgaki, K. (2003). Stability boundaries of gas hydrates helped by methane—structure-H hydrates of methylcyclohexane and cis -1, 2-dimethylcyclohexane. Chemical engineering science, 58(2), 269-273 ( résumé )
• (in) Wang, Y., Shah, N., & Huffman, G. P. (2004). Pure hydrogen production by partial dehydrogenation of cyclohexane and methylcyclohexane over nanotube-supported Pt and Pd catalysts. Energy & Fuels, 18(5), 1429-1433 ( résumé ).
• (in) I. Graça, J.-D. Comparot, S. Laforge, P. Magnoux, J.M. Lopes, M.F. Ribeiro, F. Ramôa Ribeiro (2009), Effect of phenol addition on the performances of H–Y zeolite during methylcyclohexane transformation ; Applied Catalysis A: General, Volume 353, Issue 1, 31 January 2009, Pages 123-129 ( résumé )
• (in) Amel Djeddi, Ioana Fechete, Ovidiu Ersen, François Garin (2013), Electron-deficient adduct site in the ring opening of methylcyclopentane (MCP) on tungsten-oxide-supported Pt, Ir and Pt–Ir catalysts Original Research Article

Chemistry reports, volume 16, Issue 5, May 2013, pages 433-441 ( résumé )

• (in) Yi yang, andré l. Boehman (2010), Oxidation chemistry of cyclic hydrocarbons in a motored engine: Methylcyclopentane, tetralin, and decalin  ; Combustion and Flame, Volume 157, Issue 3, March 2010, Pages 495-505 ;
• (in) Wei-guo LIN, Zhi-xian GAO (2008) Hydroconversion of methylcyclopentane over Pt/HZSM-5 catalyst: I. Effects of reaction parameters on ring enlargement reaction ; Journal of Fuel Chemistry and Technology, Volume 36, Issue 4, August 2008, Pages 449-454
• (in) B. González, A. Domínguez, J. Tojo (2006), Physical properties of the binary systems methylcyclopentane with ketones (acetone, butanone and 2-pentanone) at T = (293.15, 298.15, and 303.15) K. New UNIFAC-VISCO interaction parameters ; The Journal of Chemical Thermodynamics, Volume 38, Issue 6, June 2006, Pages 707-716
• (in) T. Zaharescu, E. Feraru, C. Podina, S. Jipa (2005), High energy radiation processing of EPDM in a hydrocarbon environment. Part 1. Methylcyclopentane ; Polymer Degradation and Stability, Volume 89, Issue 2, August 2005, Pages 373-381 ( résumé )
• Y. Zhuang, A. Frennet (1996), Methylcyclopentane hydrogenolysis on EuroPt-1 (Pt/SiO2), EuroPt-3 (Pt/Al2O3) and EuroPt-4 (PtRe/Al2O3) catalysts ; Applied Catalysis A: General, Volume 134, Issue 1, 4 January 1996, Pages 37-52