Cracking of dicyclopentadiene chemistry stack exchange. Chinese universities 2008,242, 17579 article id 10059040200802l7505 dielsalder addition of dicyclopentadiene with cyclopentadiene in polar solvents zhang xiangwen, jiang. In the cracking of dicyclopentadiene, why is it necessary to distill the product very. It will dissolve in water and evaporates quickly from water and soil surfaces. Diels alder reactions of cyclopentadiene brainmass. Cracking the dicyclopentadiene is a retrodielsalder reaction and a schematic of this reaction is shown on page. Pdf the first step on the dielsalder reaction between cyclopentadiene and maleic anhydride is actually a retro dielsalder. Procedure 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. Dicyclopentadiene is coproduced in large quantities in the steam cracking of.
In organic chemistry, the dielsalder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile also spelled dieneophile, to form a substituted. Preparation of cyclopentadiene from its dimer journal of. Please let a resonable explanation pertaining to dielsalder reactions. For example, dicyclopentadiene can be cracked to form 1,3cyclopentadiene by thermal dissociation. The rest of it forms oligomers, which require considerably higher temperature for cracking. At room temperature, it is a clear light yellow color liquid with an acrid odor. Cyclopentadiene and dicyclopentadiene researchgate. Solventfree dielsalder reactions were carried out by heating a mixture of a volatile diene, such as 1,3butadiene, isoprene, or 2,3dimethyl1,3butadiene, and a dienophile, such as methyl vinyl. Dicyclopentadiene should never be distilled to dryness since there is danger of explosion if peroxides are present. If the dielsalder reaction between dimethylmaleic anhydride and furan had worked, would cantharidin have been. The cracking of dicyclopentadiene to two moles of 1,3.
At room temperature, this cyclic diene dimerizes over the course of hours to give. Abstract the objective of this experiment was to crack dicyclopentadiene to create two molecules of cyclopentadiene, and then perform a dielsalder reaction by reacting the diene with maleic anhydride. Dicyclopentadiene, abbreviated dcpd, is a chemical compound with formula c 10h12. Cyclopentadiene and dicyclopentadiene cheung major. Cracking apparatus the dielsalder reaction of cyclopentadiene with maleic anhydride. The dimerizationmonomerization of cpd and dcpd is a direct and reverse dielsalder reaction. Gas phase cracking of dicyclopentadiene to produce. Experiment 2 organic chemistry ii pahlavancherif diels. Dicyclopentadiene wikimili, the best wikipedia reader.
In the cracking of dicyclopentadiene, why is it ne. Experiment 14 the dielsalder cycloaddition reaction pg. The dielsalder reaction that you will be performing between cyclopentadiene and maleic anhydride occurs rapidly at. We started with dicyclopentadiene which had to be cracked into cyclopentadiene. Cyclopentadiene and dicyclopentadiene, which occur as byproducts in the steam cracking process in ethylene plants, are the major ingredients in the production of hydrocarbon resins, unsaturated. Cyclopentadiene is an organic compound with the formula c5h6. Prior to running the dielsalder reaction in lab, the cyclopentadiene was cracked. Define the terms diene and dienophile as they apply to the dielsalder reaction. The reaction kinetics of cyclopentadiene dimerization. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a.
A solventfree dielsalder reaction was carried out by heating a mixture of dicyclopentadiene and a dienophile. The cracking of dicyclopentadiene to two moles of 1,3cyclopentadiene eq. Organic chemistryintroduction to reactionsdielsalder. Dicyclopentadiene is coproduced with ethylene from the c5 fraction in the steam cracking of naphtha and gas oils. This colorless liquid has a strong and unpleasant odor. Chemistry stack exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. Dicyclopentadiene, abbreviated dcpd, is a chemical compound with formula c 10 h 12. Cracking apparatus the dielsalder reaction of cyclopentadiene with maleic anhydride the dielsalder reaction that you will be. Cyclopentadiene cpd and dicyclopentadiene dcpd, which occur as byproducts in the steam cracking process in ethylene plants, are the major ingredients in the production of hydrocarbon resins. Also, when cooling a piece of equipment that contains the hot bottoms from the distillation or. The objective of this experiment was to crack dicyclopentadiene into two molecules of cyclopentadiene and mix cyclopentadiene with maleic anhydride to synthesize cisnorbornene5,6. Cyclopentadiene cpd and dicyclopentadiene dcpd are two important products obtained from oil cracking, which are interconvertable through a dielsalder reaction. Cyclopentadiene acts as the diene for the reaction. Moreover, only about 23 of dicyclopentadiene can be cracked.
Dielsalder reaction of cyclopentadiene with maleic anhydride. In a dielsalder reaction with cyclopentadiene and maleic. In the cracking of dicyclopentadiene, why is it necessary to distill the product very slowly. Cracking of dicyclopentadiene before the beginning of lab the cyclopentadiene was prepared by a lab technician by cracking it. Above 150 c, dicyclopentadiene undergoes a retrodielsalder reaction at. Dielsalder reactions chemical and biomolecular engineering. Kinetic and thermodynamic control in the dielsalder reaction. Dielsalder reactions can sometimes reverse themselves through retrodielsalder reactions. The largest consumption of dicyclopentadiene is linked to the production of resins. Cracking of dicyclopentadiene was my simple liebig condenser. However, this dielsalder reaction is reversible by cracking dicyclopentadiene using slow distillation and keeping the. When pure cyclopentadiene is stored it also undergoes a dielsalder. In a typical experiment the imine and cyclopentadiene were suspended in a mixture of hexanetoluene 3.
896 480 695 674 284 391 1294 861 1050 1113 222 123 752 563 279 1331 1521 1066 417 1025 1106 712 1181 974 335 1471 549 1410 31 326 983 1260 882 470 1449 1441 637 1457 924