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[52] Benzene molecules have been detected on Mars.[53][54][55]. National Institute of Standards and Cyclohexane consumes around 10% of the world's benzene production; it is primarily used in the manufacture of nylon fibers, which are processed into textiles and engineering plastics. The reaction of the diazonium compound derived from aniline with hypophosphorus acid gives benzene. The pure material, and any solutions containing it, constitute a fire risk. Chem. In this process, the xylene stream exiting the TDP unit is approximately 90% p-xylene. by the U.S. Secretary of Commerce on behalf of the U.S.A. : Molwarme des Systems 1,2-Dibromathan-Benzol, [43], In 1929, the cyclic nature of benzene was finally confirmed by the crystallographer Kathleen Lonsdale using X-ray diffraction methods. specific content of the mark scheme or generic level descriptors for a question. When certain compounds are heated, light is emitted because the compounds CONVERT some of the energy from the heating into coloured light of specific colours. This was seven years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. ; Jost, W., Temperature. The reaction involves the acylation of benzene (or many other aromatic rings) with an acyl chloride using a strong Lewis acid catalyst such as aluminium chloride or Iron(III) chloride. Cp values given for the pressure range 0.1 to 68.1 MPa. [83] The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is 1 ppm. Z. Phys. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute leukemia, bone marrow abnormalities and cardiovascular disease. The thermal analysis clearly ensures the enhancement in case of benzene added water upward spray, and the achieved average heat flux is 1.78 MW m 2. Coll. Thermodynam., 1991, 23, 25-30. Rastorguev, Yu.L. Am. You can target the Engineering ToolBox by using AdWords Managed Placements. [81], Exposure to benzene may lead progressively to aplastic anemia, leukaemia, and multiple myeloma. Das Benzol." The two were allowed to come to thermal equilibrium and the final temperature was 24.1C. Toluene is also processed into benzene. ; Daniels, F., Eng. Ramadevi Punyamurthy et al. J. The current NIOSH definition for an IDLH condition, as given in the NIOSH Respirator Selection Logic, is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health effects or prevent escape from such an environment. [65] More than half of the entire benzene production is processed into ethylbenzene, a precursor to styrene, which is used to make polymers and plastics like polystyrene. Specific gravity: 0.87 Principal hazards *** Benzene is a carcinogen (cancer-causing agent). Some of our calculators and applications let you save application data to your local computer. J. Chem. Chat now for more business. Staveley, L.A.K. When gasoline burns, the benzene reacts with oxygen. Specific heat of Benzene Gas - C6H6 - at temperatures ranging 250 - 900 K: Add standard and customized parametric components - like flange beams, lumbers, piping, stairs and more - to your Sketchup model with the Engineering ToolBox - SketchUp Extension - enabled for use with the amazing, fun and free SketchUp Make and SketchUp Pro .Add the Engineering ToolBox extension to your SketchUp from the SketchUp Pro Sketchup Extension Warehouse! Rabinovich, I.B. Nitrobenzene is the precursor to aniline. cHliquid : Standard liquid enthalpy of combustion (kJ/mol). Compound Name: Benzene; Formula: C6H6; at Temperature: [all data], Pacor, 1967 *** Very flammable. [all data], Czarnota, 1991 Study of the heat capacity of selected solvents, J. Measurement of the heat capacity of a small volume of liquid by the piezo-thermometric method. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5kg) or more of benzene be reported. Sci. Solution Chem., 1987, 16, 745-752. [76] There is no safe exposure level; even tiny amounts can cause harm. Acta, 1985, 88, 255-260. "VIII. Soc., 1940, 62, 696-700. Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, Sometimes, xylenes and heavier aromatics are used in place of toluene, with similar efficiency. Thermodynam., 1988, 20, 1183-1189. [77] The US Department of Health and Human Services (DHHS) classifies benzene as a human carcinogen. [all data], Andrews, Lynn, et al., 1926 Given that demand for para-xylene (p-xylene) substantially exceeds demand for other xylene isomers, a refinement of the TDP process called Selective TDP (STDP) may be used. Chemical Properties of Ethylbenzene (CAS 100-41-4) InChI InChI=1S/C8H10/c1-2-8-6-4-3-5-7-8/h3-7H,2H2,1H3 InChI Key YNQLUTRBYVCPMQ-UHFFFAOYSA-N Formula C8H10 SMILES CCc1ccccc1 Molecular Weight 1 106.17 CAS 100-41-4 Other Names .alpha.-methyltoluene Aethylbenzol Benzene, ethyl- EB Ethylbenzeen Ethylbenzol Etilbenzene Etylobenzen NCI-C56393 NSC 406903 The specific heat of a substance is the amount of energy that must be transferred to or from 1 g of that substance to change its temperature by 1. Cookies are only used in the browser to improve user experience. In the United States, concern over its negative health effects and the possibility of benzene entering the groundwater has led to stringent regulation of gasoline's benzene content, with limits typically around 1%. Excess heat capacity of the binary systems formed by n-propyl alcohol with benzene, mesitylene and cyclohexane, The heat capacity, heat of fusion and entropy of benzene, Pol. Keep locked up or in an area accessible only to qualified or authorized persons. Kalali, H.; Kohler, F.; Svejda, P., J. Chem. Ser. Mean specific heat in homologous series of binary and ternary positive azeotropes, Soc., 1925, 47, 1490-1503. Wilhelm, E.; Faradjzadeh, A.; Grolier, J.-P.E., Chem., 1971, 24, 1817-1822. Experimental device for measurement of isobaric specific heat of electrolytes at elevated pressures, (2007), Last edited on 15 February 2023, at 05:01, United States Environmental Protection Agency, US Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, Occupational Safety and Health Administration, National Institute for Occupational Safety and Health, an explosion at a China National Petroleum Corporation (CNPC) factory, Industrial Union Department v. American Petroleum Institute, Industrial & Engineering Chemistry Chemical & Engineering Data Series, "Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers", Proceedings of the National Academy of Sciences of the United States of America, "Benzene - an overview | ScienceDirect Topics", "On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat", Philosophical Transactions of the Royal Society, "ber das Benzol und die Suren der Oel- und Talgarten", Reports of the Proceedings of the Scientific Society of Freiburg, "On the oxidation of phenyl alcohol, and a mechanical arrangement adapted to illustrate structure in the non-saturated hydrocarbons", Proceedings of the Royal Society of Edinburgh, "Sur la constitution des substances aromatiques", "Ueber einige Condensationsproducte des Aldehyds", "An explanation of the laws which govern substitution in the case of benzenoid compounds", "Crocker, Not Armit and Robinson, Begat the Six Aromatic Electrons". Bull. J. Chem. Chem. Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) [88][89] In September 1995, NIOSH issued a new policy for developing recommended exposure limits (RELs) for substances, including carcinogens. Have definite shape (resist deformation) 2. [all data], Gorbunova, Simonov, et al., 1983 Database and to verify that the data contained therein have The formula for specific heat capacity, C, of a substance with mass m, is C = Q / (m T). [all data], Reddy, 1986 [all data], Gorbunova, Grigoriev, et al., 1982 According to the ATSDR Toxicological Profile for benzene, between 1978 and 1981, catalytic reformates accounted for approximately 4450% of the total U.S benzene production.[52]. Using a precise scanning-microcalorimetric technique, the heat-capacity difference between water and an aqueous solution of benzene or of toluene has been measured for a broad temperature range (from 278 to 413 K) under excess pressure, and the partial specific heat capacity of these solutes has been determined. Enthalpies of combustion of toluene, benzene, cyclohexane, cyclohexene, methylcyclopentane, 1-methylcyclopentene, and n-hexane, In nitration, benzene reacts with nitronium ions (NO2+), which is a strong electrophile produced by combining sulfuric and nitric acids. Through calculating more than thirty parameters, Lonsdale demonstrated that the benzene ring could not be anything but a flat hexagon, and provided accurate distances for all carbon-carbon bonds in the molecule. and Informatics, Vibrational and/or electronic energy levels, Electron-Impact Ionization Cross Sections (on physics web site), Computational Chemistry Comparison and Benchmark Database, X-ray Photoelectron Spectroscopy Database, version 4.1, NIST Polycyclic Aromatic Hydrocarbon Structure Index, NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data), NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data). Eng. The United States Environmental Protection Agency has set a maximum contaminant level for benzene in drinking water at 0.0005mg/L (5 ppb), as promulgated via the U.S. National Primary Drinking Water Regulations. Derivatives of benzene occur sufficiently often as a component of organic molecules, so much so that the Unicode Consortium has allocated a symbol in the Miscellaneous Technical block with the code U+232C () to represent it with three double bonds,[62] and U+23E3 () for a delocalized version.[63]. Ann. Hence it floats onwater. These applications will - due to browser restrictions - send data between your browser and our server. [17] Michael Faraday first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen. [67], As a gasoline (petrol) additive, benzene increases the octane rating and reduces knocking. Atalla, S.R. Benzene has 6 hydrogen atoms, fewer than the corresponding parent alkane, hexane, which has 14. [20] In 1836, the French chemist Auguste Laurent named the substance "phne";[21] this word has become the root of the English word "phenol", which is hydroxylated benzene, and "phenyl", the radical formed by abstraction of a hydrogen atom (free radical H) from benzene. Data, 2008, 37, 4, 1855-1996. In particular, acute myeloid leukemia or acute nonlymphocytic leukemia (AML & ANLL) is caused by benzene. Add standard and customized parametric components - like flange beams, lumbers, piping, stairs and more - to your Sketchup model with the Engineering ToolBox - SketchUp Extension - enabled for use with the amazing, fun and free SketchUp Make and SketchUp Pro .Add the Engineering ToolBox extension to your SketchUp from the SketchUp Pro Sketchup Extension Warehouse! Reddy, K.S., NQ01 and GSH shift metabolism away from toxicity. Nauk, 1962, SSSR 142, 1335-1338. Kolosovskii, N.A. The specific heats of certain organic liquids at elevated temperatures, the Benzene. The specific heats of binary mixtures, Next, the diol is newly reduced by NADH to catechol. Faraday Soc., 1955, 51, 323-342. 9.11 Ratio of Specific Heats of Vapor (Gas): 1.061 9.12 Latent Heat of Vaporization: 169 Btu/lb = 94.1 cal/g = 3.94 X 105 J/kg [107][108], This article is about the chemical compound. rend., 1933, 197, 519-520. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. . [all data], de Kolossowsky and Udowenko, 1933 ; Shipova, V.A., Keep away from heat and sources of ignition. [citation needed] Prior to the 1920s, benzene was frequently used as an industrial solvent, especially for degreasing metal. Thermodynam., 1982, 14, 259-268. Aust. Toluene hydrodealkylation converts toluene to benzene. In general, the evaluated uncertainty limits are on the order of (0.5 to 2.5) kJ/mol. The pure material, and any solutions containing it, constitute a fire risk. Measurement of air and water levels of benzene is accomplished through collection via activated charcoal tubes, which are then analyzed with a gas chromatograph. Willams, J.W. Molecular Weight 1 134.22 CAS 105-05-5 Other Names 1,4-DIETHYLBENZENE Benzene, p-diethyl- p-Diethylbenzene p-Ethylethylbenzene para-Diethylbenzene : Acentric Factor. Benzene is more resistant to temperature change than sulfuric acid. In some systems, even the benzene-to-xylenes ratio is modified to favor xylenes. Specific heat of liquids. biphenyl (aka diphenyl) at higher temperature: If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or routed through an extraction process to recover BTX aromatics (benzene, toluene and xylenes). [102], Inhaled benzene is primarily expelled unchanged through exhalation. It is a byproduct of the incomplete combustion of many materials. Akad. Pacor, P., Rajagopal, E.; Subrahmanyam, S.V., Benzene is a liquid at standard conditions. Bull. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. Safety glasses. [105] Benzene leaked into the Songhua River, which supplies drinking water to the city, after an explosion at a China National Petroleum Corporation (CNPC) factory in the city of Jilin on 13 November 2005. Swietoslawski, W.; Zielenkiewicz, A., A typical reaction yield exceeds 95%. Fortier, J.-L.; Benson, G.C., Chem. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such as naphthalene, anthracene, phenanthrene, and pyrene. ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein Complete decarboxylation of mellitic acid gives benzene. In similar fashion to this catalytic reforming, UOP and BP commercialized a method from LPG (mainly propane and butane) to aromatics. ; El-Sharkawy, A.A.; Gasser, F.A., (This estimate assumes no threshold for benzene's carcinogenic effects.) Tanaka, R., This reaction is achieved by the use of high pressures of hydrogen in the presence of heterogeneous catalysts, such as finely divided nickel. Kekul's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds[note 1], In 1845, Charles Blachford Mansfield, working under August Wilhelm von Hofmann, isolated benzene from coal tar. Except where noted otherwise, data relate to, This page was last edited on 14 February 2023, at 04:18. Benzene is hepatically metabolized and excreted in the urine. Ber. ; Nikolaev, P.N., Etude thermochimique dans la serie furanique, The current ACGIH biological exposure limits for occupational exposure are 500 g/g creatinine for muconic acid and 25 g/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.[91][92][93][94]. Expert Answer. Grolier, J.-P.E. Mesure des chaleurs specifique moleculaires de quelques liquides, J. Chem. Pure Benzene (C_6H_6) has a melting point of 5.5 degrees Celsius. The word "benzene" derives from "gum benzoin" (benzoin resin), an aromatic resin known since ancient times in Southeast Asia; and later to European pharmacists and perfumers in the 16th century via trade routes. J. Chem. [all data], Good and Smith, 1969 Chem., 1977, 81, 925-930. ; Smith, N.K., Calculate the number of joules required to melt 57.4 g of benzene at 5.5 degrees; The specific heat of toluene, C_7H_8, is 1.13 J/g K. Benzene is the name of an aromatichydrocarbon,C 6 H 6. NBS, 1946, 36, 455-461. The heat capacity of the system benzene + diphenylmethane, Heat capacity of benzene and of toluene from 8C. Ahlberg, J.E. [101] After smoking 32 cigarettes per day, the smoker would take in about 1.8 milligrams (mg) of benzene. Specific heat of liquids. Andrews, D.H.; Lynn, G.; Johnston, J., This discovery led to the production of Sanka. A. III. Heat capacity of liquid benzene and hexafluorobenzene at atmospheric pressure, Roux, M.V. FOIA. Good, W.D. The U.S. National Institute for Occupational Safety and Health (NIOSH) revised the Immediately Dangerous to Life and Health (IDLH) concentration for benzene to 500 ppm. Chem., 1965, 96, 669-678. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, Benzene, C6H6, is a clear colorless to light-yellow liquid, flammable with a petroleum-like, aromatic odor. Findenegg, G.H. In industrybenzeneis used as a solvent, as a chemical intermediate, and is used in the synthesis of numerous chemicals. [all data], Prosen, Gilmont, et al., 1945 J. Chem. Univ. Thermodynamic properties of benzene, These applications will - due to browser restrictions - send data between your browser and our server. 1196-58-3. Benzene should NOT be used at all unless no safer alternatives are available. Gorbunova, N.I. ; Temprado, M.; Chickos, J.S. Have no definite shape 2. Huffman, H.M.; Parks, G.S. This reaction is called Sandmeyer reaction. On this Wikipedia the language links are at the top of the page across from the article title. [all data], Vesely, Zabransky, et al., 1979 Thus, a double bond would exist with one neighbor during the first interval and with the other neighbor during the next interval. J. Chem. Uber binare flussige Mischungen I. Mischungswarment, Volumseffekte und Zustandsdiagramme von chlorex mit benzol und n-alkylbenzolen, Under these conditions, toluene undergoes dealkylation to benzene and methane: This irreversible reaction is accompanied by an equilibrium side reaction that produces In a human study 16.4 to 41.6% of retained benzene was eliminated through the lungs within five to seven hours after a two- to three-hour exposure to 47 to 110 ppm and only 0.07 to 0.2% of the remaining benzene was excreted unchanged in the urine. Smart Sensor: 10.0 eV Lamp, 100 ppm, Benzene specific 50 ppm (PID003L), with tube holder & box of 10 tubes This powerful hand-held instrument is capable of simultaneously monitoring up to 6 gases. [all data], Hyder Khan and Subrahmanyam, 1971 Grolier, J.-P.E. Thermodynam., 1976, 8, 289-299. Phys., 1937, 5, 537-551. ; Wilhelm, E.; Hamedi, M.H., One way of understanding the carcinogenic effects of benzene is by examining the products of biological oxidation. ; Rossini, F.D., As benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the REL (10-hour) of 0.1 ppm. specific heat liquid = 1.740 J/g C A 27.00 g sample of liquid benzene is initially at 41.30 C. To examine the effects of suppression of NOS activity on hematopoietic stem cells, we treated animals with NOS inhibitors or with control saline solution for 6 or 12 days and analyzed the changes in long-term engraftment of cells from these animals using a competitive repopulation assay: we mixed BM cells from the treated animals expressing the Ly-5.1 (CD45.1) alloantigen with a 4-fold excess . [66], Toluene is now often used as a substitute for benzene, for instance as a fuel additive. Khim., 1941, 11, 471-482.