Patent Description:
Dicyclopentadiene is used as a highly reactive intermediate for producing resins such as unsaturated polyesters and aromatic hydrocarbons. Generally, dicyclopentadiene is formed by dimerization of cyclopentadiene, which is a component of pygas generated from steam cracking of naphtha. In a conventional process of cyclopentadiene dimerization, a tubular reactor is used to provide a relatively long residence time that is sufficient to achieve a high conversion rate. The tubular reactor is typically surrounded by a large heat sink medium because the cyclopentadiene dimerization is highly exothermic. However, the long residence time can only be achieved with very long tubular reactor. Another instance is to use a large tank with one or more impellers to quickly mix the liquid and dissipate the heat generated during the dimerization reaction.

However, the economic feasibility of the conventional cyclopentadiene dimerization process is relatively limited. First of all, for the conventional method to achieve a cyclopentadiene conversion rate of above <NUM>%, the energy demand is relatively high as the reactor has to be kept at an elevated reaction temperature for an extended period to achieve the required long residence time. Additionally, impellers in the tank reactors also demand a lot of energy. Thus, overall, the energy consumption of the conventional dimerization method is high. Moreover, impellers cannot sufficiently mix the liquid in the reactor, and such mixing forms hot spots in the liquid in the cyclopentadiene dimerization reactor. These hot spots not only limit the conversion rate of cyclopentadiene, but also induce side reactions for cyclopentadiene to form higher polymers other than dimers. Therefore, improvements in this field are desired. <CIT> discloses a production method of a highly pure dicyclopentadiene usable in the production of resins and nornbomene derivatives from C5-fraction of hydrocarbon pyrolysis which comprises the steps of: dimerization of cyclopentadiene contained in C5-fractions by heating at the temperature of <NUM>-<NUM> to <NUM> % conversion to form a dimerized mixture; separating said dimerized mixture into a pure dicyclopentadiene by fractionation; monomerization of the said a pure dicyclopentadiene in the presence of a high-boiling solvent and a polymerization inhibitor at the temperature of <NUM>-<NUM> to form a monomerized mixture; separating said monomerized mixture into a pure cyclopentadiene by fractionation; dimerization of said a pure cyclopentadiene by heating at the temperature of <NUM>-<NUM> to <NUM>-<NUM> % conversion to form a dicyclopentadiene-enriched effluent; separating said dicyclopentadiene-enriched effluent into a highly pure dicyclopentadiene by fractionation, wherein a highly pure dicyclopentadiene has a purity of at least about <NUM> %. <CIT> discloses a process wherein cyclopentadiene is removed from a hydrocarbon stream also containing isoprene and/or piperylene by dimerization in a reaction zone in which the stream is maintained at its boiling point, the pressure being such that said boiling point is about <NUM>-<NUM>, and the residence time being <NUM>-<NUM> hours.

The invention relates to a method of producing dicyclopentadiene (C<NUM>H<NUM>) according to claim <NUM>. Specific embodiments are described in dependent claims and this specification. A method has been discovered for dimerizing cyclopentadiene to form dicyclopentadiene. By using a jet mixer to inject a C<NUM> hydrocarbon mixture comprising cyclopentadiene into a C<NUM> hydrocarbon liquid in a tank, a dimerization reaction can be included. During the injecting, the exothermic heat generated by the dimerization reaction can be quickly dissipated with low energy consumption, thereby reducing the operating costs. Furthermore, the C<NUM> hydrocarbon liquid in the tank can be used as the heat sink medium without need of extra cooling structures (e.g. cooling jacket and cooling coil), thereby reducing capital expenditure and operating costs.

The method includes flowing a C<NUM> hydrocarbon mixture stream that comprises cyclopentadiene (C<NUM>H<NUM>) to a tank. The method further includes injecting the C<NUM> hydrocarbon mixture stream as a jet stream into C<NUM> hydrocarbon liquid in the tank at a velocity in a range of <NUM>/s to <NUM>/s and under reaction conditions sufficient to dimerize the cyclopentadiene to form dicyclopentadiene. The reaction conditions include a reaction temperature of between <NUM> to <NUM>. The injecting causes mixing of the C<NUM> hydrocarbon mixture stream and the C<NUM> hydrocarbon liquid.

The terms "wt. %" or "mol. %" refer to a weight, volume, or molar percentage of a component, respectively, based on the total weight, the total volume, or the total moles of material that includes the component. In a non-limiting example, <NUM> moles of component in <NUM> moles of the material is <NUM> mol. % of component.

The term "primarily," as that term is used in the specification and/or claims, means greater than any of <NUM> wt. %, <NUM> mol. %, or <NUM> vol. For example, "primarily" may include <NUM> wt. % to <NUM> wt. % and all values and ranges there between, <NUM> mol. % to <NUM> mol. % and all values and ranges there between, or <NUM> vol. % to <NUM> vol. % and all values and ranges there between.

The terms "inhibiting" or "reducing" or "preventing" or "avoiding" or any variation of these terms, when used in the claims and/or the specification, include any measurable decrease or complete inhibition to achieve a desired result.

The term "vertical angle," as that term is used in the specification and/or claims means an angle between a direction of injection and a horizontal plane.

The term "horizontal angle," as that term is used in the specification and/or claims means an angle, in a horizontal plane, between a direction of injection and a bisector of an angle that is formed by the left limit and right limit of the injection direction for the jet mixer.

Other objects, features and advantages of the present invention will become apparent from the following figures, detailed description, and examples. It should be understood, however, that the figures, detailed description, and examples, while indicating specific embodiments of the invention, are given by way of illustration only and are not meant to be limiting. Additionally, it is contemplated that changes and modifications within the scope of the claims will become apparent to those skilled in the art from this detailed description.

A method has been discovered for producing dicyclopentadiene from cyclopentadiene. The method uses a jet mixer in a reactor tank configured to inject C<NUM> hydrocarbon mixture comprising cyclopentadiene into a C<NUM> hydrocarbon liquid. The efficiency of mixing of the C<NUM> hydrocarbon mixture and the C<NUM> hydrocarbon liquid improves compared to mixing with an impeller. Furthermore, overheating of C<NUM> hydrocarbon mixture is avoided by using the jet mixer. Moreover, the jet mixer reduces large amounts of energy consumption for mixing the C<NUM> hydrocarbon mixture and the C<NUM> hydrocarbon liquid compared to mixing by an impeller, thereby reducing the operating costs.

With reference to <FIG>, a schematic diagram is shown of jet mixing system <NUM> for dimerizing cyclopentadiene to form dicyclopentadiene, according to embodiments of the invention. Jet mixing system <NUM> may include reactor tank <NUM> as a container for holding liquid. In embodiments of the invention, the liquid is a C<NUM> hydrocarbon liquid. The C<NUM> hydrocarbon liquid may include C<NUM> linear hydrocarbons, C<NUM> linear hydrocarbons, C<NUM> cyclo hydrocarbons, C<NUM> linear hydrocarbons, C<NUM> cyclo hydrocarbons, or combinations thereof, preferably C<NUM> linear hydrocarbons, C<NUM> linear hydrocarbons and C<NUM> cyclo hydrocarbons. In embodiments of the invention, reactor tank <NUM> may be in a shape that is substantially a horizontal cylinder, a vertical cylinder, a rectangle tank, a horizontal oval, a vertical oval, a horizontal capsule, or a vertical capsule. In embodiments of the invention, reactor tank <NUM> may be cylindrical or spherical.

According to embodiments of the invention, reactor tank <NUM> may include liquid inlet <NUM> adapted to receive the C<NUM> hydrocarbon liquid into reactor tank <NUM>. In some instances, this flow of C<NUM> hydrocarbon liquid into the reactor tank may not be needed. In embodiments of the invention, jet mixing system <NUM> may further include first heat exchanger <NUM> in fluid communication with liquid inlet <NUM>. According to embodiments of the invention, first heat exchanger <NUM> may be configured to heat or cool C<NUM> hydrocarbon liquid stream <NUM> such that C<NUM> hydrocarbon liquid stream <NUM> is in a temperature range of <NUM> to <NUM> and all ranges and values there between including ranges of <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, and <NUM> to <NUM>. In embodiments of the invention, jet mixing system <NUM> may further include a temperature control system that comprises temperature transmitter <NUM> and temperature controller <NUM>. Temperature transmitter <NUM> may be adapted to measure a temperature in reactor tank <NUM>. Temperature controller may be adapted to adjust first heat exchanger <NUM> based on a temperature measurement from temperature transmitter <NUM> such that the temperature in reactor tank <NUM> is in a range of <NUM> to <NUM> and all ranges and values there between. When C<NUM> hydrocarbon liquid is not needed, the control system <NUM> and <NUM> can be connected to heat exchanger <NUM> instead.

Jet mixing system <NUM> may further include jet inlet <NUM> disposed in tank <NUM>. Jet inlet <NUM> may be adapted to inject a liquid to reactor tank <NUM>. In embodiments of the invention, as shown in a side view of reactor tank <NUM> in <FIG>, jet inlet <NUM> may be adapted to inject a liquid at a vertical angle, which means an angle between a horizontal plane and a direction of injection, in a range of -<NUM>° to <NUM>° and all ranges and values there between including ranges of -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to - <NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, and <NUM>° to <NUM>°. According to embodiments of the invention, as shown in a top view of reactor tank <NUM> in <FIG>, jet inlet <NUM> may be adapted to inject a liquid at a horizontal angle (<NUM> in <FIG>) in a range of -<NUM>° to <NUM>° and all ranges and values there between, including ranges of -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to -<NUM>°, -<NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, <NUM>° to <NUM>°, and <NUM>° to <NUM>°.

According to embodiments of the invention, jet inlet <NUM> may be adapted to inject a liquid at a velocity in a range of <NUM>/s to <NUM>/s and all ranges and values there between including <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, and <NUM>/s. In embodiments of the invention, jet inlet <NUM> may be adapted to inject a liquid at a flow rate such that a residence time for a jet stream from jet inlet <NUM> is in a range of <NUM> to <NUM> hours and all ranges and values there between including <NUM> to <NUM> hours, <NUM> to <NUM> hours, <NUM> to <NUM> hours, <NUM> to <NUM> hours, <NUM> to <NUM> hours, <NUM> to <NUM> hours, <NUM> to <NUM> hours, <NUM> to <NUM> hours, and <NUM> to <NUM> hours. In embodiments of the invention, a flow rate of the jet stream from jet inlet <NUM> may be in a range of <NUM> to <NUM><NUM>·hr-<NUM> and all ranges and values there between including <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, and <NUM> to <NUM><NUM>·hr-<NUM>. A volume of the C<NUM> hydrocarbon liquid in reactor tank <NUM> may be in a range of <NUM> to <NUM><NUM> and all ranges and values there between including <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, <NUM> to <NUM><NUM>, and <NUM> to <NUM><NUM>. According to embodiments of the invention, the C<NUM> hydrocarbon liquid in reactor tank <NUM> may have a vertical height L and a diameter/width D such that a ratio of L to D is in a range of <NUM> to <NUM> and all ranges and values there between including <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, and <NUM>.

In embodiments of the invention, jet inlet <NUM> may be in fluid communication with feed inlet <NUM> configured to flow C<NUM> hydrocarbon mixture that comprises cyclopentadiene through jet inlet <NUM>. In embodiments of the invention, jet mixing system <NUM> may further include second heat exchanger <NUM> adapted to heat and/or cool stream <NUM> of the C<NUM> hydrocarbon mixture flowing through jet inlet <NUM> such that a jet stream of C<NUM> hydrocarbon mixture injected from jet inlet <NUM> is at a temperature of <NUM> to <NUM> and all ranges and values there between, including ranges of <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, and <NUM> to <NUM>.

In embodiments of the invention, jet mixing system <NUM> may include outlet <NUM>, which leads from the inside to the outside of reactor tank <NUM>. Outlet <NUM> may be adapted to flow effluent stream <NUM> from reactor tank <NUM>. According to embodiments of the invention, jet mixing system <NUM> may be in fluid communication with separation and recovery unit <NUM>. Separation and recovery unit <NUM> may be adapted to separate effluent stream <NUM> into product stream <NUM> that comprises primarily dicylopentadiene, first recycle stream <NUM> that comprises unreacted cyclopentadiene, and second recycle stream <NUM> that comprises the C<NUM> hydrocarbon liquid. According to embodiments of the invention, first recycle stream <NUM> may be flowed into stream <NUM> of the C<NUM> hydrocarbon mixture. Second recycle stream <NUM> may be flowed into liquid stream <NUM> of the C<NUM> hydrocarbon liquid. If C<NUM> hydrocarbon liquid is not used, recycle stream <NUM> can be connected to C<NUM> hydrocarbon mixture.

<FIG> shows method <NUM> for producing dicyclopentadiene from cyclopentadiene. Method <NUM> may be implemented by jet mixing system <NUM> as shown in <FIG>. Method <NUM> includes flowing a C<NUM> hydrocarbon mixture stream (stream <NUM>) that comprises cyclopentadiene (C<NUM>H<NUM>) to reactor tank <NUM>, as shown in block <NUM>. In embodiments of the invention, a typical composition of the C<NUM> hydrocarbon mixture stream may be <NUM> to <NUM> wt. % cyclopentadiene, <NUM> to <NUM> wt. % C<NUM> linear hydrocarbons, <NUM> to <NUM> wt. % C<NUM> linear and cyclo hydrocarbons and <NUM> to <NUM> wt. % C<NUM> linear and cyclo hydrocarbons. In embodiments of the invention, the C<NUM> hydrocarbon mixture may flow through second heat exchanger <NUM>, then into reactor tank <NUM>. The C<NUM> hydrocarbon mixture stream (stream <NUM>) may be heated by second heat exchanger <NUM> to a temperature in a range of <NUM> to <NUM> and all ranges and values there between, including <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, and <NUM> to <NUM>.

The method <NUM> includes injecting the C<NUM> hydrocarbon mixture stream as a jet stream into C<NUM> hydrocarbon liquid in reactor tank <NUM> under reaction conditions sufficient to dimerize the cyclopentadiene to form dicyclopentadiene, as shown in block <NUM>. The jet stream is injected at a velocity of <NUM>/s to <NUM>/s, and all ranges and values there between including <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, <NUM>/s, and <NUM>/s may be applied. As described above, the jet stream may be injected into reactor tank <NUM> at a vertical angle in a range of -<NUM>° to <NUM>° and a horizontal angle in a range of -<NUM>° to <NUM>°.

The reaction conditions include a reaction temperature of <NUM> to <NUM>, and all ranges and values thereof may be applied, including ranges of <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, and <NUM> to <NUM>. Preferably, the reaction temperature may be in a range of <NUM> to <NUM>. In embodiments of the invention, the jet stream from jet inlet <NUM> may have a temperature in a range of <NUM> to <NUM>, and all ranges and values there between including <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, and <NUM> to <NUM>. According to embodiments of the invention, the temperature of the C<NUM> hydrocarbon liquid may be at least <NUM> to <NUM> above the temperature of the jet stream. In embodiments of the invention, the jet stream may have a flowrate in a range of <NUM> to <NUM><NUM>·hr-<NUM>, and all ranges and values there between including <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, <NUM> to <NUM><NUM>·hr-<NUM>, and <NUM> to <NUM><NUM>·hr-<NUM>. C<NUM> hydrocarbon mixture may have a residence time in reactor tank <NUM> in a range of <NUM> to <NUM> minutes and all ranges and values there between including <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, <NUM> to <NUM> minutes, and <NUM> to <NUM> minutes. In embodiments of the invention, at blocks <NUM> and <NUM>, jet mixing system <NUM> may be operated as a continuous system, a batch system, or a semi-batch system.

In embodiments of the invention, the injecting causes mixing of the C<NUM> hydrocarbon mixture stream from jet inlet <NUM> and the C<NUM> hydrocarbon liquid in reactor tank <NUM>. The mixing process in the injecting may substantially follow a mixing process of an ideal continuous stirred-tank reactor. In embodiments of the invention, a mixing time for mixing the C<NUM> hydrocarbon mixture stream and the C<NUM> hydrocarbon liquid may be less than <NUM> minutes. According to embodiments of the invention, the C<NUM> hydrocarbon liquid in reactor tank <NUM> may be a heat sink liquid adapted to absorb heat generated by dimerizing cyclopentadiene. In embodiments of the invention, in the injecting step, substantially no C<NUM> hydrocarbon mixture or C<NUM> hydrocarbon liquid is overheated, thereby minimizing side reactions of polymerizing cyclopentadiene. The cyclopentadiene may have a conversion rate in a range of <NUM> to <NUM>% and all ranges and values there between, including ranges of <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, <NUM> to <NUM>%, and <NUM> to <NUM>%.

In embodiments of the invention, effluent stream <NUM> may be flowed to separation and recovery unit <NUM>. According to embodiments of the invention, as shown at block <NUM>, method <NUM> may further include separating effluent stream <NUM> into product stream <NUM> that comprises primarily dicylopentadiene, first recycle stream <NUM> that comprises unreacted cyclopentadiene, and second recycle stream <NUM> that comprises the C<NUM> hydrocarbon liquid. In embodiments of the invention, as shown in block <NUM>, method <NUM> may further include flowing first recycle stream <NUM> into stream <NUM> and flowing second recycle stream <NUM> into liquid stream <NUM> such that C<NUM> hydrocarbon liquid from effluent stream <NUM> and unreacted cyclopentadiene from effluent stream <NUM> can be recycled to reactor tank <NUM>.

In summary, embodiments of the invention involve a method of producing dicyclopentadiene from cyclopentadiene. By using a jet mixer to inject a C<NUM> hydrocarbon mixture comprising cyclopentadiene into a C<NUM> hydrocarbon liquid, the energy consumption for the mixing process is significantly less than using conventional methods, thereby reducing operating costs of cyclopentadiene dimerization. Furthermore, the mixing by jet mixer can avoid the formation of any overheating spots in the C<NUM> hydrocarbon liquid and C<NUM> hydrocarbon mixture, thereby minimizing unwanted side reactions.

Although embodiments of the present invention have been described with reference to blocks of <FIG>, it should be appreciated that operation of the present invention is not limited to the particular blocks and/or the particular order of the blocks illustrated in <FIG>. Accordingly, embodiments of the invention may provide functionality as described herein using various blocks in a sequence different than that of <FIG>.

As part of the disclosure of the present invention, specific examples are included below. The examples are for illustrative purposes only and are not intended to limit the invention. Those of ordinary skill in the art will readily recognize parameters that can be changed or modified to yield essentially the same results.

Computational Fluid Dynamics (CFD) simulations were run on liquid mixing process using a jet mixer in commercial CFD software ANSYS® FLUENT <NUM> platform. Tracer injections were simulated under a non-reacting isothermal condition. The tank size used for simulation was <NUM><NUM>. The viscosity and density of the fluid was <NUM> cp and <NUM>/m<NUM>, respectively. The tracer was pulse-injected through the jet mixer to the tank in all the simulations. As shown in <FIG>, the simulation results indicate that the tracer concentration at the tank outlet substantially followed the mixing curve of an ideal continuous stirred-tank reactor (CSTR). Therefore, the jet mixer is highly efficient for mixing of liquid in a reactor tank. Furthermore, the mixing time in all the simulation runs was significantly shorter than the expected global residence time. In all the simulation runs, mixing time was calculated from the injection of the tracer until the time when the percentage deviation of the tracer concentration throughout the tank is less than <NUM>% from the mean tracer concentration in the tank. Moreover, in all the simulation runs, the power consumption of the jet mixer was calculated. The results showed that the power for the jet mixer needed for mixing a liquid at a flowrate of <NUM><NUM>/hr and jet stream velocity of <NUM>/s in a <NUM> liter tank was less than <NUM>,<NUM> kilowatt (<NUM> horsepower), which is significantly lower than using impellers to mix the liquid at comparable efficiency.

Computational Fluid Dynamics (CFD) model was constructed in commercial CFD software ANSYS® FLUENT <NUM> platform. The reversible reaction of dimerizing cyclopentadiene to form dicyclopentadiene was included in the model. The reaction conditions for the simulation included a reaction temperature of <NUM>, jet stream flowrate of <NUM> to <NUM><NUM>/hr, jet stream velocity of <NUM> to <NUM>/s, and a tank volume of <NUM><NUM>. The simulation results showed that the temperature in the reactor tank was substantially uniform with deviation of temperature less than <NUM> from the mean temperature. The maximum temperature difference throughout the reactor tank is about <NUM>. <FIG> shows dimensionless temperature contour in the reactor tank at two vertical planes, indicating substantially uniform temperature distribution in the reactor tank. In all simulation runs, no overheating spot (hot spot) was formed in the reactor tanks, thereby minimizing undesirable side reactions. The temperature throughout the reactor tank was within the limit to avoid undesirable reactions, which occur above <NUM>. Furthermore, the simulation results show that the conversion rate of cyclopentadiene to dicyclopentadiene was more than <NUM>%, which is significantly higher than the conversion rate of using conventional methods. Overall, the simulation results demonstrated that a jet mixing based method according to embodiments of the invention is superior to conventional methods that uses impellers for mixing the liquid in the reactor tank mainly due to short mixing time, avoidance of hot-spot formation, and high conversion rate.

Claim 1:
A method of producing dicyclopentadiene (C<NUM>H<NUM>), the method comprising:
flowing a C<NUM> hydrocarbon mixture stream that comprises cyclopentadiene (C<NUM>H<NUM>) to a tank; and
injecting the C<NUM> hydrocarbon mixture stream as a jet stream into C<NUM> hydrocarbon liquid in the tank at a velocity in a range from <NUM>/s to <NUM>/s and under reaction conditions sufficient to dimerize the cyclopentadiene to form dicyclopentadiene,
wherein the injecting causes mixing of the C<NUM> hydrocarbon mixture stream and the C<NUM> hydrocarbon liquid, wherein reaction conditions include a reaction temperature of between <NUM> to <NUM>.