Mar 02, 1999 various dicyclopentadiene cracking methods are known. At room temperature, it is a clear light yellow color liquid with an acrid odor. Additional information about the chemicals will be found in appendix a. Dcpd products originate from high temperature cracking of petroleum fractions and are best characterized as highly reactive intermediates used for a. The sensitivity is determined by the slope of the calibration curve see figure 3. The first step on the dielsalder reaction between cyclopentadiene and. One object of the invention is to provide a process of the foregoing type which is. However, this dielsalder reaction is reversible by cracking dicyclopentadiene using slow distillation and keeping the cyclopentadiene cold. Expired lifetime application number us433091a inventor alger l ward. The dicyclopentadiene separated from liquid products of hydrocarbon thermal cracking was used as a feedstock for complex and monomeration experiments. As obtained above, the product has a refractive index of about 1. Increasing the antiknock quality of gasoline fuels can enable higher efficiency in spark ignition engines. Standard operating procedures sop policies and procedures manual templates save time. The process for the production of cyclopentadiene by the substantially quantitative splitting or monomerizing of a dicyclopentadiene concentrate containing thermally stable dimers of isoprene and.
The appearance of crystals white crystalline powder c. The dicyclopentadiene dimer c 10 h 12 is broken down cracked to the monomer c 5 h 6 cp. Cyclopentadiene was prepared by cracking dicyclopentadiene org. 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. Dicyclopentadiene osha z 1 a twa 5 ppm, 30 mgm3 acgih twa urt irr0. Cyclopentadiene dimer, 4,7methano3a,4,7,7atetrahydroindene, dicyclopentadiene cas number 77736. Its low cost, high reactivity, and tendency to form. In the autoclave reactor, reaction temperature, reaction time, diluent, and. Subject to polymerization if subjected to heat for prolonged periods or if contaminated. Dcpd is a cyclic hydrocarbon that appears as colorless crystals, soluble in ethanol, diethyl ether, and acetic acid. Diels alder reactions of cyclopentadiene brainmass. In this study, the blending antiknock quality of dicyclopentadiene dcpd, a byproduct of ethylene production from naphtha cracking. May react exothermically with reducing agents to release hydrogen gas.
Dicyclopentadiene may react vigorously with oxidizing agents. Us2372237a us433091a us43309142a us2372237a us 2372237 a us2372237 a us 2372237a us 433091 a us433091 a us 433091a us 43309142 a us43309142 a us 43309142a us 2372237 a us2372237 a us 2372237a authority us united states prior art keywords cyclopentadiene dicyclopentadiene. Two streams of resin are injected into the mold simultaneously, along with a catalyst such as molybdenum or tungsten to set off the proper chemical reaction. Optimum embodiments of the invention provide for about 98100% conversion of dicyclopentadiene to monomer at about 97100% purity.
Cyclopentadiene is an organic compound with the formula c 5 h 6. Cycloaddition of cyclopentadiene and dicyclopentadiene on. As dicyclopentadiene enters the air, it breaks down quickly into simpler, lesstoxic chemicals. The objective of this experiment was to crack dicyclopentadiene into two molecules of cyclopentadiene and mix cyclopentadiene with maleic anhydride to synthesize cisnorbornene5,6endodicarboxylic anhydride. Therefore, a procedure that allows use of dicyclopentadiene directly would have important practical advantages. The thermodynamic parameters of this process have been measured. Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene. Its low cost, high reactivity, and tendency to form tough, highly crosslinked materials have made it a good choice for reaction injection molding rim. However, it can stay unchanged for a long time in soil and in. Cyclopentadiene, a reagent commonly used in organic synthesis, is known to. The organic liquids used in quantity in this experiment. It utilizes a closed mold and a lowmoisture lowoxygen environment. Solventfree dielsalder reactions of in situ generated.
The present invention relates to a vaporphase thermal cracking process of dicyclopentadiene which can achieve a superior cracking rate and can be operated in a stable manner for a long period of time, and to a simple and industrial process for manufacturing high purity dicyclopentadine suitable as a raw material for the reaction. This procedure largely avoids the codimerization of cyclopentadiene with residual unsaturated c5 impurities, allowing the latter to be removed from dicyclopentadiene by stripping. Abstract cyclopentadiene and dicyclopentadiene, which occur as byproducts in the steam cracking process in ethylene. 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. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Dicyclopentadiene dcpd, a dimer of cyclopentadiene, is a white crystalline chemical compound with camphorlike odor. Dicyclopentadiene appears as a liquid with an acrid odor. Dicyclopentadiene, abbreviated dcpd, is a chemical compound with formula c 10h12. The first step in the synthesis of cpru pph 3 2 cl is to crack the dicyclopentadiene dimer. Experimental procedure part a cracking of dicyclopentadiene. Its a colorless, waxy, flammable solid or liquid, with a camphorlike odor. This colorless liquid has a strong and unpleasant odor.
The sensitivity of the analytical procedure over a concentration range of 0. Us3719718a process for the production of cyclopentadiene. Use sop best practices to save hundreds of hours researching polices and writing procedures. Kommerziell erhaltliches dicyclopentadien iupacname. Dicyclopentadiene wisconsin department of health services. The first use of a chemical is designated in the procedure with an asterisk. 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 cyclopentadiene needed for the dielsalder reaction and for the preparation of ferrocene. The dissociation to the monomer is a monomolecular reaction. The potential hazards from cyclopentadiene storage and use on kilogram scale are studied under adiabatic conditions.
Process and system for making cyclopentadiene andor dicyclopentadiene. In the past few decades, dicyclopentadiene dcp has received significant attention as a monomer for ring opening metathesis polymerization romp. The flask containing dicyclopentadiene is now heated by means of an electric heating mantle or oil bath to approximately 160, or until cyclopentadiene distils smoothly at 3846 and a little dicyclopentadiene refluxes from the coldfinger friedrichs condenser. The experimental procedure of obtaining cyclopentadiene followed the work from magnusson and eastwood and coworkers. Tricyclopentadiene tcpd, or cyclopentadiene trimer, is a raw material used to produce tetrahydrotricyclopentadiene thtcpd, which is the fully hydrogenated form of tcpd. Dicyclopentadiene, abbreviated dcpd, is a chemical compound with formula c10h12. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a dielsalder reaction. Dicyclopentadiene is a peroxide forming chemical pfc. Dicyclopentadiene stabilised for synthesis synonym. Us20090112033a1 process for production of dicyclopentadiene. Large quantities are coproduced in the steam cracking of naphtha and gas oils to ethylene. In this study, the blending antiknock quality of dicyclopentadiene dcpd, a byproduct of ethylene production from naphtha cracking, with various gasoline fuels is explored.
The reaction kinetics of cyclopentadiene dimerization. Procedure for preparing cyclopentadiene from its dimer. The rate of monomer formation cracking becomes reasonable at temperatures above 150 c and approaching the boiling point of the dimer. Gas phase cracking of dicyclopentadiene to produce. The setup as instructed by my supervisor consisted of a simple watercooled liebig condenser. Results show that the optimal cracking conditions of dcpd are cracking.
Dicyclopentadiene cracking process boulder scientific. As steam cracking processes shift to using lighter feed e. Download easily editable ms word policy and procedures template files customize them for your company. Dicyclopentadiene is coproduced in large quantities in the steam cracking of. This is achieved by using the fractional distillation set up shown in the photo. 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. Aldrich 454338 page 1 of 7 sigmaaldrich material safety data sheet version 4. A process for the preparation of dicyclopentadiene dcpd modified. Synthesis of cyclopentadiene trimer tricyclopentadiene over. The beam must be straight and the crack edges must be aligned before repairing the crack.
To crack the dicyclopentadiene, we used fractional distillation, which involves boiling the mixture to remove a certain compound by recondensing it. Us2372237a process for converting dicyclopentadiene to. The objective of this experiment was to crack dicyclopentadiene into two molecules of cyclopentadiene and mix cyclopentadiene with maleic anhydride to synthesize. Thus, when cyclopentadiene is obtained by cracking of dicyclopentadiene, one can expect, at best, an overall 6570% reaction yield with respect to dicyclopentadiene.
Experimental procedure cracking dicyclopentadiene to obtain cyclopentadiene as discussed in the introduction, cyclopentadiene must be obtained by cracking dicyclopentadiene. When pure cyclopentadiene is stored it also undergoes a dielsalder. Cyclopentadiene, which will be used in this experiment cannot be purchased commercially, and must be prepare in the lab by thermally cracking dicyclopentadiene. Liquidphase cracking of dicyclopentadiene by reactive. Dcpd products originate from high temperature cracking.
Preparation of cyclopentadiene from its dimer journal of. I recently did a distillation of dicyclopentadiene bp 166 c to get cyclopentadiene bp 40 c. The present invention relates to a vaporphase thermal cracking process of dicyclopentadiene which can achieve a superior cracking. Theoretical melting point of cisnorbornene5,6endodicarboxylic anhydride 165c d. It is produced in bulk quantities through steam cracking of c5 petroleum products such as gas oils, naphtha, and crude oil. Dcpd reaction injection molding is a process for quickly, efficiently creating large parts using dicyclopentadiene resin. Preparation of cyclopentadiene from dicyclopentadiene. Cracking of dicyclopentadiene before the beginning of lab the cyclopentadiene was prepared by a lab technician by cracking it. Synthesis of cyclopentadiene trimer tricyclopentadiene. Dicyclopentadiene, abbreviated dcpd, is a chemical compound with formula c 10 h 12. When pure cyclopentadiene is stored it also undergoes a dielsalder cycloaddition reaction and forms. And also state whether they will be racemix, and draw its 3d configuration.
The dicyclopentadiene pilot plant production in chemopetrol company is based on dicyclopentadiene separation from the mixture of liquid products obtained by the hydrocarbon thermal cracking. Dielsalder reactions chemical and biomolecular engineering. Evaluation of antiknock quality of dicyclopentadiene gasoline blends 2017010804 increasing the antiknock quality of gasoline fuels can enable higher efficiency in spark ignition engines. Solution a process for the production of dicyclopentadiene is. Tack weld the runoff tab to the backing plate and clamp this assembly to the flange at the crack location. Dicyclopentadiene is primarily used in unsaturated polyester resins and also used in inks, adhesives, and paints. Dicyclopentadiene products a guide to product handling and use disclaimer the information, specification, procedures, methods and recomme ndations herein are presented in good faith, are. Dicyclopentadiene is coproduced in large quantities in the steam cracking.
The reaction kinetics of cyclopentadiene dimerization using. Figure one demonstrates the fractional distillation set up which was used to crack dicyclopentadiene. After twothirds of the dicyclopentadiene has been pyrolyzed during the course of 45 hours, the residue in the flask may. Dcpd dicyclopentadiene reaction injection molding romeo rim. Cyclopentadiene and dicyclopentadiene cheung major. It consists predominantly of hydrocarbons having carbon numbers of c5 and dicyclopentadiene. The process for the production of cyclopentadiene by the substantially quantitative splitting or monomerizing of a dicyclopentadiene concentrate containing thermally stable dimers of isoprene and codimers of cyclopentadiene, isoprene and piperylene and having been obtained by the heat treatment of a c5 fraction of a pyrolysis petrol and its subsequent enrichment by fractional distillation. Cyclopentadiene dimerization and cracking dicyclopentadiene b. An uncontrolled cracking of dcpd reverse diels alder reaction with subsequent. The invention also includes a dicyclopentadiene cracking apparatus or system. In other words, in the cracking of dicyclopentadiene, why is it necessary to distill the product very slowly. Process for producing cyclopentadiene and its homologues. In addition to the thermodynamics research center trc data available from this site, much more physical and chemical property data is available from the following trc products.
Cracking of dicyclopentadiene chemistry stack exchange. Sop policies and procedures manual templates bizmanualz. Working with hazardous chemicals organic syntheses. Dicyclopentadiene dcpd is typically a clear liquid with a fragrant strong musty odor. If the polymerization takes place inside a container, the container may violently rupture. A complex combination of hydrocarbons obtained by distillation of the products from a steam cracking process. All procedures involving benzene should be carried out in a wellventilated. The vapors are irritating to the eyes and respiratory system. Following the general procedure of example 1, but wherein the steam was also utilized.
The process of producing highpurity cyclopentadiene cpd has been investigated. Evaluation of antiknock quality of dicyclopentadiene. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene. Cyclopentadiene trimer tricyclopentadiene is an important raw material during the synthesis of highenergydensity fuel. The cracking can be accomplished by distilling dicyclopentadiene under atmospheric pressure. This procedure largely avoids the codimerization of cyclopentadiene with residual unsaturated c5 impurities, allowing the latter to be removed from dicyclopentadiene.
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. Dielsalder reaction of cyclopentadiene with maleic anhydride. A reactive distillation process was developed for cracking dicyclopentadiene dcpd to produce cyclopentadiene cpd. Cyclopentadiene dimerizes rapidly at room temperature and should be used immediately note 5 or stored at dry ice temperatures. Subject to polymerization if subjected to heat for prolonged periods or if. Us6515071b1 process for the preparation of dicyclopentadiene. Dicyclopentadiene dcpd 3a,4,7,7atetrahydo4,7methano1hindene c10h12 general dicyclopentadiene or dcpd is the dimer of cyclopentadiene cpd formed by a dielsalder addition reaction. If you were to attempt to distill the monomer from the dimer at say 60 c it would probably take a very long time due to the slow rate of monomer formation at that. Dicyclopentadiene products a guide to product handling and use disclaimer the information, specification, procedures, methods and recomme ndations herein are presented in good faith, are believed to be accurate and reliable, but may well be incomplete andor not applicable to all conditions or situations that may exist or occur. For example, the reaction converting c5 hydrocarbons to cpd is extremely. For example, in the presence of sulfuric acid, water adds to dcpd to form the exo secondary alcohol.
494 1135 123 1154 962 504 889 766 1478 237 584 552 163 1332 1228 1137 1394 447 756 164 1474 1059 326 851 473 738 656 1 629 505 945 992 1454 991 1233 1269 1361 1104 1179 183 1021 625 1187 317 528 122