Gasoline contains 5% to 7% toluene by weighty making toluene a common airborne contaminant in industrialized countries. Us2704295a us298474a us29847452a us2704295a us 2704295 a us2704295 a us 2704295a us 298474 a us298474 a us 298474a us 29847452 a us29847452 a us 29847452a us 2704295 a us2704295 a us 2704295a authority us united states prior art keywords benzene sulfur trioxide weight reaction parts prior art date 19520711 legal status the legal status is an assumption and is not a. In 1991, 3,104,000 megagrams 944 million gallons of toluene were recovered. Reaction conditions of toluene sulfonation with gaseous so 3 were studied in order to establish optimum conditions. Nearly all functional groups which present a problem in gas chromatogaphic separation hydroxyl, carboxylic acid, amine, thiol, phosphate can be derivatized by silylation reagents. Sulfonation of benzene benzene will react with sulfur trioxide, and in the presence of an acid, aryl sulfonic acids are produced. It is a member of toluenes and an arenesulfonic acid.
Exposure to p toluene sulfonic acid can irritate the nose, throat and lungs causing burning, dryness and coughing. Environmental alert toluenes use is increasing partially because of its popularity as a solvent replacement for benzene. If your well water has high levels of toluene, contact your local or state health agency or the centers for disease control and prevention cdc for information on how to reduce your exposure. This is of particular value in the petrochemical industry to manufacture pxylene, styrene, and other aromatic compounds. Determination of the density of toluene in the range from. The amount of toluene in mainstream smoke from an unfiltered cigarette was estimated to range from 100 to 200 g with a sidestreammainstream smoke ratio of 1. Having nitrogen present in a ring is very useful because it can be used as a directing group as well as a masked amino group. Formation and biodegradation of toluene in the anaerobic sludge digestion process article pdf available in water environment research 773. The following table provides volume correction factors in metric units based at 15 c for a 95 to 100 percent mixture of toluene and with density ranges of 869 to 873 kgm3 at 15 c. A hydrostatic balance densitometer with a magnetic suspension coupling has been used to measure the density of liquid toluene in the range from 293 to 373 k and pressures up to 30 mpa. Toluene is a major component of tobacco smoke and concentrations can vary greatly. Silylation is the most widely used derivatization technique. If you want this mechanism explained to you in detail, there is a link at the bottom of the page.
Nitration and sulfonation of benzene chemistry libretexts. It is routinely added to gasoline as an additive along with benzene and xylene to increase the octane. Toluene is a manmade aromatic hydrocarbon produced mostly from petroleum. Hazards identification potential acute health effects. Heat benzene under reflux with concentrated sulfuric acid for several hours. Toluene alternative names include methylbenzene, toluol, anisen, phenyl methane.
Gc experimental method o the solvent samples were directly analyzed without dilution. The cooled reaction mixture was stirred with an equal volume of water, then with an aqueous suspension of 5. Reactions of aromatic compounds rutgers university. Preparation of toluene and desulfonation in detail youtube. Common impurities include benzenesulfonic acid and sulfuric acid. Process for the sulphonation of toluene allied chem. The source is also providing more information like the publication year, authors and more. Last revised 09232005 the rfd is an estimate of an oral exposure, for a given duration, to the human population including susceptible subgroups that is likely to be without an appreciable risk of adverse health effects over a lifetime. It comprises 1520 percent of coaltar light oil and is a minor constituent of petroleum. Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution.
Transalkylation is a chemical reaction involving the transfer of an alkyl group from one organic compound to another. Find more compounds similar to 3aminop toluene sulfonic acid. Patents and patent applications class 56298 filed with the uspto. So3 is an aggressive electrophilic reagent that rapidly reacts with any organic compound containing an electron donor group.
Unit specification limits 1 appearance astm d 4176 visual clear liquid free of sediments or haze 2 colour astm d 1209 ptco 10 max. Toluene silent 24h 70 90 toluene 4 sulfonic acid toluene 45min 76 100 toluene 4 sulfonic acid. Chemical product and company identification product name. The sulfonic acids are among the most important of the organosulfur compounds.
Sulfonation of benzene in organic chemistry duration. Other reactions of benzene and methylbenzene chemistry. It is first isolated in 1837 by distillation of pine oil by a polish chemist named filip walter. It is colorless, waterinsoluble and has a smell associated with paint thinners.
Toluene sulfonic acid, liquid, with more than 5% free sulfuric acid appears as colorless to black. Pdf treatment of toluene and its byproducts using an. Alibaba manufacturer directory suppliers, manufacturers. Commission regulation eu no 2015830 of 28 may 2015. Study on the sulfonation of toluene with so3 in microreactor. The benzene to toluene activity coefficient ratio is slightly greater than unity. Formulating with toluene sulfonamide promotes resistance to oils, greases, and solvents. Greener methods for batch sulfonation presented by anuja a. New results of measurements of the density of toluene in the compressed liquid region are presented and compared with literature data. Toluene 4 sulfonic acid is an arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group. Toluene is used as a feedstock for a number of chemical syntheses including production of tda, tdi, dnt, tnt, benzene and xylene. Monohydrate ptsa contains crystalline water as well as water as impurity. Aryl sulfonic acids are used as detergents, dye, and drugs. Important sulfonation procedures include the reaction of aromatic hydrocarbons with sulfuric acid, sulfur trioxide, or chlorosulfuric acid.
Toluene wt, % min 99,2 benzene wt, % max 0,02 sulphur wt, % 0,25 section 3. Sulfonation of toluene sulfonation agent used mainly with ptoluene sulfonic acid with sulfuric acid, sulfur trioxide, chlorosulfonic acid. Therefore, in chemical process industry, excess sulfonic acid is used in order to increase the reaction yield. Most toluene produced is derived from petroleum fractions. Preliminary study of sulfonation of polystyrene by. Toluene is produced during the process of making gasoline and other fuels from crude oil, in making coke from coal, and as a byproduct in the manufacture of styrene. It deals with the combustion, hydrogenation and sulphonation of benzene and methylbenzene toluene, and with the oxidation of side chains attached to benzene rings. Organic lecture series 16 friedelcrafts alkylation friedelcrafts alkylation forms a new cc bond between an aromatic ring and an. The solubility of benzene and toluene in aqueous sulfuric acid 75 wt.
It was used to label twentysix fatty acids c5c30 successfully in the presence of k 2co 3 catalyst in n,ndimethylformamide solvent. So3 is an aggressive electrophilic reagent that rapidly reacts with any organic compound containing an. Sulfonation of benzene benzene will react with sulfur trioxide, and in the presence of an acid, aryl sulfonic. Dissolution in water or dilution of concentrated solutions with water may generate significant heat. Take the time to validate and double check the source of the data. Exposure to toluene may occur from breathing ambient or indoor air affected by such sources. Material safety data sheet section 1 chemical product and company identification msds name. Toluene sulfonamide is used as highperformance plasticizer for paints, adhesives, nitrocellulose, and plastics. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Product identifier product name ptoluenesulfonic acid product number ft11451. Toluene can also be used as a recreational inhalant sometimes, and it also has the potential of causing severe neurological harm. It is an aromatic hydrocarbon, and occurs both naturally and due to human activity. Tsoh is prepared on an industrial scale by the sulfonation of toluene. In contrast to the usual interpretations, the results provide clear evidence that in nonpolar media and in the absence of catalysts the mechanism of aromatic sulfonation with a single so3 is concerted and does not.
It is used as antistatic agents and as gloss enhancers in plastic film preparations. The reactions can generate dangerously large amounts of heat in small spaces. May 2017 product overview toluene is a clear, colorless, flammable liquid with a scent similar to paint thinner. This msds summarizes at the date of issue our best knowledge of the health, safety and environmental hazard information related. Toluene, aromatic hydrocarbon used extensively as starting material for the manufacture of industrial chemicals. Chemical and physical properties of p toluene sulfonic acid. The ortho isomer is produced as the main impurity following that the methyl group of toluene is orthopara directing and must be removed. Toluene cas 108883 market research report 20192025 toluene cas 108883 report studies the global market size of it, especially focuses on the key regions like united states, european union, china, and other regions japan, korea, india and southeast asia. Toluene is also called as toluol, is an aromatic hydrocarbon.
Relevant identified uses of the substance or mixture and uses advised against recommended use laboratory chemicals. Granted application number us11906,307 other versions us7709693b2 en inventor benjamin f. Chemical properties of p toluene sulfonic acid cas 104154 download as pdf file download as excel file download as 2d mole file. Pdf formation and biodegradation of toluene in the. Search for sulfonation utilizing sulfur trioxide or oleum e. Occupational health and safety act act 85 of 1993 16 other information notice to reader.
Specifications determined for this separation are an achievement of 99. In section 6, major conclusions in the characterization of hazard and dose response. Naturallyoccurring toluene was first isolated from a. The central nervous system cns is the primary target organ for toluene toxicity in both humans and animals for acute shortterm and chronic longterm exposures. Toluene 4sulfonamide is a sulfonamide that is benzenesulfonamide bearing a methyl group at position 4. The sulfonation of toluene to produce p toluene sulfonic acid ptsa is strongly limited by chemical equilibrium.
The solubility of toluene and benzene in concentrated. Procedure rbf was placed at the center of ultrasonic bath. Pdf scientific advances in sulfuric acid free toluene. The vials were sealed and exposed to uv light at 365 nm and power of 100 w for 5s, 5min, 30min and 60min. Hazardous in case of skin contact irritant, of eye contact irritant, of ingestion, of inhalation. Preliminary study of sulfonation of polystyrene by homogeneous and heterogeneous reaction f. Sulfonic acid, sulfonic also spelled sulphonic, any of a class of organic acids containing sulfur and having the general formula rso 3 h, in which r is an organic combining group. Specifications for toluene parameter value molecular formula c7h8 mol wt 92. Abbreviated tscl or toscl, it is a derivative of toluene and contains a sulfonyl chloride. Volume correction factors to 15 c for toluene temperature c volume correction factor. Pocket guide to chemical hazards material type value toluene cas 108883 stel 560 mgm3 150 ppm twa 375 mgm3 100 ppm biological limit values acgih biological exposure indices material value determinant specimen sampling time 0. Toluene is an aromatic hydrocarbon a methylsubstituted benzene derivative, which occurs as a clear colorless volatile liquid and possesses a pungent, benzenelike odor. Treatment of toluene and its byproducts using an electron beamultra fine bubble hybrid system article pdf available in radiation physics and chemistry september 2017 with 6 reads.
The nitronium ion reacts with benzene to form the sigma complex, which then loses a proton to generate the aromatic product. Toluene is water insoluble but is miscible with other organic solvents. Us2697117a us235672a us23567251a us2697117a us 2697117 a us2697117 a us 2697117a us 235672 a us235672 a us 235672a us 23567251 a us23567251 a us 23567251a us 2697117 a us2697117 a us 2697117a authority us united states prior art keywords benzene reaction product sulfonation water prior art date 19510707 legal status the legal status is an assumption and is not. Identification of the substancemixture and of the companyundertaking 1.
This table has been developed from astm d 155568a in british units. Toluene sulfonic acid, liquid, with more than 5% free sulfuric acid reacts exothermically with chemical bases for example. A system of local andor general exhaust is recommended to keep employee exposures as low as possible. The uncertainty of the present density data is estimated to be within 0. Many organic solvents have great addictive potential. Unlike other electrophilic substitution reactions, sulphonation is unique in the. Four 20 ml glass vials were each charged with 10 ml of a toluene solution of sbs 10 gl, 1. The concentration per cigarette in sidestream smoke is typically higher than in mainstream smoke. Safety data sheet ptoluenesulfonic acid according to regulation ec no 19072006, annex ii, as amended. The reaction is used for the transfer of methyl and ethyl groups between benzene rings. However others, such as sulfamic acid sulfation, cannot be used to make sulfonic acids. Toluene maximum concentration 500 ppm na osha z2 toluene twa 200 ppm na osha z2 toluene twa 20 ppm na acgih note.
Toluene is added to gasoline, used to produce benzene, and used as a solvent. Ppt toluene powerpoint presentation free to download id. Sulfonation of aromatic compounds in presence of sio 2 khso 4 catalyst substrate product conventional microwave entry r. You have clicked a page that seems to be very popular. This page gives details of some reactions of benzene and methylbenzene toluene not covered elsewhere in this section.
Nitration is used to add nitrogen to a benzene ring, which can be used further in substitution reactions. Toluene is also used as a component of solvents in paint and lacquer industry and as an octane enhancing component of gasoline. In this video, i make ptoluenesulfonic acid by sulfonating toluene. Distillate stream is cooled down using a total condenser and partially returned to maintain reflux. Sulfonation, also spelled sulphonation, in chemistry, any of several methods by which sulfonic acids are prepared.
This white, malodorous solid is a reagent widely used in organic synthesis. Toluene specifications reliance industries limited. Both sources provide toluene for commercial use, but larger amounts are made by catalytic r. Mar 21, 2017 we take a look at the chemistry of sulfonates and prepare toluene from paratoluenesulfonic acid. Sulphuric acid generates sulfur trioxide which acts as the electrophilic species. Alfredo campo, in selection of polymeric materials, 2008. Sulfonation of anisole, phenol, toluene and related alkyl. This study presents the toluene cas 108883 production, revenue, market share. It is not intended to be a comprehensive treatise on the chemical or toxicological nature of toluene. Toluene is an aromatic hydrocarbon solvent and natural sources of toluene include crude oil and small quantities it is found in tolu tree. The label must carry the following additional information. It was shown that reaction temperature, concentration of so 3 and water quantity. Having nitrogen present in a ring is very useful because it can be used as a. Introduction sulphonation of toluene yields paratoluenesulphonic acid as the main product.
Safety data sheet paratoluene sulfonic acid date prepared. There are two equivalent ways of sulfonating benzene. Page 6 of 16 msds toluene engineering controls the level of protection and types of controls necessary will vary depending. Product identifier product name toluene product number toen reach registration number 012119471051xxxx cas number 108883 eu index number 601021003 ec number 2036259 1. Application specific toluene toluene histological, fisher chemical cas. Toluene structure, properties, preparation and reactions. May 31, 2017 keep toluene containing products tightly covered when not in use to prevent evaporation.
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