It is based on observations during laboratory scale preparation of. If your institution is not listed, please contact your librarian. Your new online msds binder is a place for you to store the material safety data sheets you need to deploy. Thank you for visiting our website you are exiting the department of labors web server. However, this dielsalder reaction is reversible by cracking dicyclopentadiene using slow distillation and keeping the cyclopentadiene cold.
When pure cyclopentadiene is stored it also undergoes a dielsalder cycloaddition reaction and forms. Cyclopentadiene and dicyclopentadiene cheung major. Dicyclopentadiene is both extremely flammable and toxic. Gas phase cracking of dicyclopentadiene to produce. Large quantities are coproduced in the steam cracking of naphtha and gas oils to ethylene. Experimental procedure cracking of dicyclopentadiene before the beginning of lab the cyclopentadiene was prepared by a lab technician by cracking it. Cracking of dicyclopentadiene before the beginning of lab the cyclopentadiene was prepared by a lab technician by cracking it. Also, when cooling a piece of equipment that contains the hot bottoms from the distillation or cracking of dicyclopentadiene, care should be taken to exclude air. Cyclopentadiene was prepared by cracking dicyclopentadiene org. Liquidphase cracking of dicyclopentadiene by reactive distillation. Undergoes a spontaneous dimerization at room temperature to give dicyclopentadiene c10h12, cas no. Experimental procedure part a cracking of dicyclopentadiene. Code of federal regulations title 49 section 172 shipping regulations and proper shipping name.
Safety data sheet crude dicyclopentadiene version 2. In the third step, the crude dicyclopentadiene is monomerized, either in the liquid phase at 170 200 c or in the gas phase at 300 400 c in the presence of diluents such as steam, hydrogen, nitrogen, or methane, to give cyclopentadiene in ca. Indication of any immediate medical attention and special treatment needed. Identification of the substancemixture and of the companyundertaking. The distillation andor cracking of dicyclopentadiene should be carried out in an inert atmosphere to. May 01, 2015 video shows what dicyclopentadiene means. Show this material safety data sheet to the doctor in attendance. An unsaturated tricyclic hydrocarbon 3a,4,7,7atetrahydro4,7methano1hindene produced in the cracking of naphtha. Catalytic enantioselective 1,4iodofunctionalizations of conjugated dienes. Dielsalder and melting point chem217labsfall07 openstax cnx.
Safety data sheet northwest missouri state university. Cracking of dicyclopentadiene chemistry stack exchange. We have tried to make it as accurate and useful as possible, but can take no responsibility for its use, misuse, or accuracy. Solar driven uphill conversion of dicyclopentadiene to. If the polymerization takes place inside a container, the container may violently rupture. Place 2 g of maleic anhydride in a 50ml erlenmeyer flask and dissolve it in 8 ml of ethyl acetate by warming on a hot plate. Dicyclopentadiene may react vigorously with oxidizing agents. Cyclopentadiene is a colorless liquid with an irritating, terpenelike odor. It also has a very unpleasant odorkeep it in the hood as much as possible. This is achieved by using the fractional distillation set up shown in the photo. A meta description is an html tag in the html code of your website, which allows you to customize a section of text that describes the page itself. Solventfree dielsalder reactions of in situ generated.
Department of transportation, the emergency response guidebook erg or safety materials. I recently did a distillation of dicyclopentadiene bp 166 c to get cyclopentadiene bp 40 c. Because of its reactivity, cyclopentadiene is normally available only in the stable dimer form. Preparation of cisnorbornene2,3endodicarboxylic anhydride introduction. Other companies are charging thousands of dollars to set up accounts and give you access to their msds online database. Cyclopentadiene dimer chemical reference number cas. An uncontrolled cracking of dcpd reverse diels alder reaction with subsequent. These are compounds containing a nonaromatic closed ring of carbon atoms in which at least 2 atoms are connected by a double bond. Dicyclopentadiene should never be distilled to dryness since there is danger of explosion if peroxides are present. Material safety data sheet dicyclopentadiene, 95%, stabilized. In the autoclave reactor, reaction temperature, reaction time, diluent, and inhibitors are investigated to study the effect of inhibiting oligomerization reactions. Can undergo exothermic polymierization reactions in the presence of various catalysts such as acids or initiators, if subjected to heat for prolonged periods, or if contaminated.
Cyclopentadiene can be further purified by sequential dimerizations under carefully controlled slow heat soaking and subsequent monomerizations. The dicyclopentadiene dimer is cracked to the monomeric cyclopentadiene by. Cyclopentadiene dimer, 4,7 methano 3a,4,7,7a tetrahydroindene, dicyclopentadiene. Hexanes petroleum ether and ethyl acetate are flammable. Material may produce a serious, potentially fatal pneumonia if swallowed or vomited. First rinse with plenty of water for several minutes remove contact lenses if easily possible, then refer for medical attention. This information was last updated on march 23, 2005. Cyclopentadiene belongs to the class of organic compounds known as cycloalkenes. The distillation andor cracking of dicyclopentadiene should be carried out in an inert atmosphere to prevent the formation of peroxides.
State key laboratory of chemical engineering, east china university of. Figure one demonstrates the fractional distillation set up which was used to crack dicyclopentadiene. The dow chemical company dow encourages customers and potential users of their. It will dissolve in water and evaporates quickly from water and soil surfaces. Usually it is obtained by cracking of dicyclopentadiene and is used. The dicyclopentadiene will be cracked for you by your t. At room temperature, it is a clear light yellow color liquid with an acrid odor. It plays a role in how your page is seen by search engine crawlers, and how it appears in serps. The appearance of crystals white crystalline powder c. Dicyclopentadiene safety data sheet 08022016 en english us sds id. The setup as instructed by my supervisor consisted of a simple watercooled liebig condenser. At the boiling point of dicyclopentadiene, equilibration with the. Usdot 2008 emergency response guidebook initial response information.
Add 8 ml of hexane or petroleum ether, and then cool the solution in an ice bath. Be careful when injecting the cyclopentadiene into the test tube and. Dicyclopentadiene appears as a liquid with an acrid odor. Theoretical melting point of cisnorbornene5,6endodicarboxylic anhydride 165c d. When pure cyclopentadiene is stored it also undergoes a dielsalder cycloaddition reaction and forms dicyclopentadiene. Procedure for preparing cyclopentadiene from its dimer. Every student must wear a laboratory coat, safety goggles, and face protection. In order to be of any use, the dimer must be cracked and distilled. In the cracking of dicyclopentadiene, why is it necessary to distill the product very slowly. The apparatus for the cracking of dicyclopentadiene to cyclopentadiene will be set up in the hood and will be used to prepare all of the cyclopentadiene needed for the dielsalder reaction and for the preparation of ferrocene. The department of labor does not endorse, takes no responsibility for, and exercises no control over the linked organization or its views, or contents, nor does it vouch for the accuracy or accessibility of the information contained on the destination server.
The vapors are irritating to the eyes and respiratory system. Osha occupational chemical database occupational safety and. In 1921, otto diels and kurt alder discovered that certain alkenes and alkynes can undergo a 1,4addition with conjugated dienes to give substituted cyclohexenes or 1,4cyclohexadienes. Dicyclopentadiene is manufacturered from high temperature cracking of petroleum fractions in an ethylene manufacturing process. In the autoclave reactor, reaction temperature, reaction time, diluent, and. May react exothermically with reducing agents to release hydrogen gas. Its a colorless, waxy, flammable solid or liquid, with a camphorlike odor. The process of producing highpurity cyclopentadiene cpd has been investigated, including a gas phase thermal cracking process of dicyclopentadiene dcpd in the presence of h2 on a continuous. Safety dicyclopentadiene is both extremely flammable and toxic. Dicyclopentadiene wisconsin department of health services. Preparation of cyclopentadiene from its dimer journal of. Cp, in turn, is obtained from endodicyclopentadiene 5 through a retro dielsalder.
The dicyclopentadiene dimer c 10 h 12 is broken down cracked to the monomer c 5 h 6 cp. This colorless liquid has a strong and unpleasant odor. This page contains information on the chemical dicyclopentadiene including. Experiment 49, the dielsalder reaction of cyclopentadiene with. Dicyclopentadiene, 77736, laboratory chemicals, c10h12 by loba chemie, india. Subject to polymerization if subjected to heat for prolonged periods or if contaminated. A reactive distillation process was developed for cracking dicyclopentadiene dcpd to produce cyclopentadiene cpd. Sigmaaldrich 3050 spruce street saint louis mo 63103 usa telephone. If distillation occurs at a faster rate, then it would be harder to handle. Dielsalder reaction is reversible by cracking dicyclopentadiene using slow distillation and. Dicyclopentadiene is classified as moderately toxic. Type part of your institution name for a list of matches.
Dicyclopentadiene, 95%, stabilized with 100200 ppm ptertbutylcatechol catalog numbers. As dicyclopentadiene enters the air, it breaks down quickly into simpler, lesstoxic chemicals. Cyclopentadiene is an organic compound with the formula c 5 h 6. Dielsalder reaction synthesis of cisnorbornene2,3endodicarboxylic anhydride introduction. Start program and collect fresh cracked cyclopentadiene in round bottom. Dicyclopentadiene is primarily used in unsaturated polyester resins and also used in inks, adhesives, and paints. It is used in the manufacturer of some pesticides, as a grass growth regulator and, in some instances, as a mammal repellent. Characterization of the proteins from vigna unguiculata seeds. If you have any questions or comments, please contact an epichem representative. Dicyclopentadiene, abbreviated dcpd, is a chemical compound with formula c 10 h 12. No workplace exposure level could be found in the literature but dicyclopentadiene is used as an intermediate for cyclodiene pesticides. Conversion under photochemical conditions in the laboratory using artificial light. The first step in the synthesis of cpru pph 3 2 cl is to crack the dicyclopentadiene dimer. However, it can stay unchanged for a long time in soil and in.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene. Liquidphase cracking of dicyclopentadiene by reactive. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a dielsalder reaction. The reaction is strongly exothermic hazardous chemicals desk reference, p. S expected from the cracking of one molecule of 5 into two molecules of cp.
Nov 30, 1990 dicyclopentadiene is obtained by cracking the dicyclopentadiene in the crude stream, separating the lowboiling cyclopentadiene by distillation, and allowing the concentrated cyclopentadiene to dimerize under controlled conditions kirkothmer, 1979. This new compound must be separated before the desired compound can be used. Ened0760 dicyclopentadiene dicyclopentadiene safety data sheet ened0760 date of issue. Information contained in this material safety data sheet is offered without charge for use by technically qualified personnel at their discretion and risk. Dicyclopentadiene is a peroxide forming chemical pfc. Cdc niosh pocket guide to chemical hazards cyclopentadiene. The purpose of this lab is to introduce the concept of the melting point of an. You have selected the maximum number of product attributes 3 to compare. Als environmental is a laboratory testing network and is not affiliated with the u. Dielsalder reaction of cyclopentadiene with maleic anhydride.
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