CN105062579A - Method for preparing high-density mixed hydrocarbon liquid jet fuel from dicyclopentadiene - Google Patents
Method for preparing high-density mixed hydrocarbon liquid jet fuel from dicyclopentadiene Download PDFInfo
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- CN105062579A CN105062579A CN201510563807.0A CN201510563807A CN105062579A CN 105062579 A CN105062579 A CN 105062579A CN 201510563807 A CN201510563807 A CN 201510563807A CN 105062579 A CN105062579 A CN 105062579A
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Abstract
The invention relates to a preparation method of a mixed hydrocarbon liquid jet fuel, which comprises the following steps: (1) adding bridged or suspended dicyclopentadiene and a nickel catalyst into a reaction kettle, carrying out polymerization reaction to obtain a first mixture containing tricyclopentadiene and bridged or suspended dicyclopentadiene; (2) carrying out hydrogenation reaction on the first mixture to obtain a second mixture containing bridged or suspended tetrahydrodicyclopentadiene and multiple tetrahydrotricyclopentadiene isomers; (3) when the raw material is the bridged dicyclopentadiene, adding an AlCl3 catalyst into the second mixture, and reacting at 30-150 DEG C for 1-40 hours to obtain a third mixture containing suspended tetrahydrodicyclopentadiene and multiple tetrahydrotricyclopentadiene isomers; and (4) removing the catalyst to obtain the mixed hydrocarbon liquid jet fuel. The method greatly optimizes the preparation technique of the mixed fuel, enhances the yield, greatly lowers the preparation cost, and is easier for large-scale production.
Description
Technical field
The invention belongs to high-density hydrocarbon mixture liquid rocket engine fuel preparation method technical field, be specifically related to a kind of method being prepared high-density hydrocarbon mixture liquid rocket engine fuel by dicyclopentadiene.
Background technology
The aircraft such as liquid rocket engine fuel is supersonic fighterplane, strategy and tactics guided missile, rocket provide motivational guarantee; High density liquid rocket engine fuel has the volume energy higher than conventional aviation kerosene, can provide more promotion energy, significantly improve the speed of a ship or plane of aircraft, load and voyage for aircraft.
The synthetic method of high density liquid rocket engine fuel is related in the published Chinese patent CN200710057328.7 of US Patent No. 3701812, US4086286, US4401837 and applicant, it is raw material by cyclopentadiene and bridge dicyclopentadiene, prepare the tetrahydrochysene three cyclopentadiene product containing several isomers by polymerization, hydrogenation, isomery and refining technique successively, its density is 1.037g/cm
3, freezing point is lower than-40 DEG C, and volume calorific value is 44.1MJ/L, can be used as rocket engine fuel and directly to use or as the high energy additive of other fuel.
The synthetic method of liquid rocket engine fuel hanging type tetrahydrochysene dicyclopentadiene (JP-10) is disclosed in published Chinese patent CN200710057329.1 and CN200610015341.1 of applicant, it is that raw material prepares highly purified hanging type tetrahydrochysene dicyclopentadiene product by bridge dicyclopentadiene or hanging dicyclopentadiene, and its density is 0.935g/cm
3, freezing point is-78 DEG C, and volume calorific value is 39.6MJ/L, can be used as rocket engine fuel and directly uses, and also can be used as the composite component of other composite rocket engine fuels.
Synthesize JP-10 or tetrahydrochysene three cyclopentadiene in above-mentioned patent respectively, wherein the low-temperature performance of JP-10 is good, but volume calorific value is on the low side; The volume calorific value of tetrahydrochysene three cyclopentadiene is higher, but low-temperature performance is poor, particularly low temperature viscosity is high, and flowing property is not good enough at low temperatures, higher to engine calls, therefore in use more as high energy component and the composite rear use of JP-10 fuel when directly using as rocket engine fuel.Therefore existing High-Density Jet in actual use, and how by JP-10 and the composite use of tetrahydrochysene three cyclopentadiene, compound proportion scope is: the mass ratio 10: 90 ~ 80: 20 of tetrahydrochysene three cyclopentadiene and JP-10.Applicant " density be greater than 1 high density liquid hydrocarbon fuel synthesis and composition research ", energetic material, studied in great detail in 2009,17:157-160. paper the rocket engine fuel different ratios such as JP-10 and tetrahydrochysene three cyclopentadiene composite after performance.
Meanwhile, both JP-10 and tetrahydrochysene three cyclopentadiene are in independent building-up process, and all need by hydrogenation, isomery and the operation such as refining, yield is relatively low, and production cost is higher.In the prior art in the hydrogenation prepared of disclosed tetrahydrochysene three cyclopentadiene and isomerization processes process, need to use a large amount of organic solvents; Use the consumption of catalyzer very large in isomerization processes, and major part cannot reclaim and reuse simultaneously; Containing a large amount of solvent and catalyzer, later separation process for refining difficulty is increased in the product that reaction generates, yield reduces, and production cost is high.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of high-density hydrocarbon mixture rocket engine fuel, the present invention directly regulates both JP-10 and tetrahydrochysene three cyclopentadiene component concentration to replace preparing JP-10 and tetrahydrochysene three cyclopentadiene respectively in advance in prior art in preparation of fuel process, then by method composite for two kinds of fuel physical.Method of the present invention makes the preparation technology of hydrocarbon mixture rocket engine fuel greatly optimize, and makes that yield improves, preparation cost significantly reduces simultaneously, and hydrogenation catalyst can reuse, and is easier to scale production.
First aspect present invention relates to a kind of preparation method of hydrocarbon mixture liquid rocket engine fuel, and it comprises the following steps:
(1) bridge dicyclopentadiene and nickel catalyzator are added in reactor, polyreaction 6-68h under 0.1 ~ 3Mpa nitrogen, the condition of 140 ~ 250 DEG C, obtain the first mixture containing three cyclopentadiene and bridge dicyclopentadiene;
(2) by above-mentioned first mixture hydrogenation reaction 10-35h under 2 ~ 6MPa hydrogen, the condition of 100 ~ 250 DEG C, the second mixture containing bridge-type tetrahydro-dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers is obtained;
(3) in above-mentioned second mixture, AlCl is added
3catalyzer, reacts the 3rd mixture obtained for 1 ~ 40 hour containing hanging type tetrahydrochysene dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers at 30 DEG C ~ 150 DEG C temperature;
(4) remove the catalyzer in above-mentioned 3rd mixture, obtain described hydrocarbon mixture liquid rocket engine fuel.
Wherein said catalyzer can be removed by the mode of filtering.Preferably, the step of product being washed purifying is also comprised in step (4).In product, add water, stratification after washing, retain supernatant liquid, be target product hydrocarbon mixture liquid rocket engine fuel.
In a preferred embodiment of the present invention, the addition of described nickel catalyzator is 3% ~ 15% of bridge dicyclopentadiene weight.
In a preferred embodiment of the present invention, described AlCl
3the addition of catalyzer is 2% ~ 25% of described second mixture weight.
In a preferred embodiment of the present invention, by the polymerization time in set-up procedure (1), the mass ratio of hanging type tetrahydrochysene dicyclopentadiene described in product and described multiple tetrahydrochysene three cyclopentadiene isomers is controlled 10: 90 ~ 91: 9.Wherein, in the course of the polymerization process, raw material dicyclopentadiene experiences the process of first open loop repolymerization.
In a preferred embodiment of the present invention, after its described hydrogenation reaction be also included in step (2) terminates, by the step that the nickel catalyzator in reactant is removed.
Second aspect present invention relates to the preparation method of another kind of hydrocarbon mixture liquid rocket engine fuel, and it adds before the described nickel catalyzator added in step (1) in the preparation method described in first aspect present invention being changed into the described hydrogenation reaction in step (2).
Third aspect present invention relates to the preparation method of another kind of hydrocarbon mixture liquid rocket engine fuel, and it comprises the following steps:
(1) hanging dicyclopentadiene and nickel catalyzator are added in reactor, polyreaction 6-68h under 0.1 ~ 3Mpa nitrogen, the condition of 140 ~ 250 DEG C, obtain the primary mixes containing three cyclopentadiene and hanging dicyclopentadiene;
(2) by above-mentioned primary mixes hydrogenation reaction 10-35h under 2 ~ 6MPa hydrogen, the condition of 100 ~ 250 DEG C, the two-stage mixture containing hanging type tetrahydrochysene dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers is obtained;
(3) remove the catalyzer in above-mentioned two-stage mixture, obtain described hydrocarbon mixture liquid rocket engine fuel.
In a preferred embodiment of the present invention, the addition of described nickel catalyzator is 3% ~ 15% of hanging dicyclopentadiene weight.
In a preferred embodiment of the present invention, by the polymerization time in set-up procedure (1), the mass ratio of hanging type tetrahydrochysene dicyclopentadiene described in product and described multiple tetrahydrochysene three cyclopentadiene isomers is controlled 10: 90 ~ 91: 9.
Fourth aspect present invention relates to the preparation method of another kind of hydrocarbon mixture liquid rocket engine fuel, and it adds before the described nickel catalyzator added in step (1) in the preparation method described in third aspect present invention being changed into the described hydrogenation reaction in step (2).
The invention has the advantages that:
1, the present invention's direct obtained JP-10 and tetrahydrochysene three cyclopentadiene hydrocarbon mixture simultaneously in rocket engine fuel preparation process obtains high-density hydrocarbon mixture liquid rocket engine fuel, by changing both preparation condition (such as controlling polymerization time) direct adjustment JP-10 and tetrahydrochysene three cyclopentadiene proportion of composing in preparation process.JP-10 and tetrahydrochysene three cyclopentadiene is prepared respectively in advance relative in prior art, again by the method for two kinds of fuel in required ratio physical compounding, method of the present invention makes the preparation technology of propellant combination greatly optimize, make that yield improves, preparation cost significantly reduces simultaneously, hydrogenation catalyst can reuse, and is easier to scale production.Prepare in the performance of the high-density hydrocarbon mixture liquid rocket engine fuel obtained by the present invention and prior art after JP-10 and tetrahydrochysene three cyclopentadiene that the composite composite fuel obtained is suitable in proportion more respectively, directly can use as rocket engine fuel.
2, need to use a large amount of organic solvent in the hydrogenation in the cyclopentadiene of tetrahydrochysene three disclosed in prior art preparation method and isomerization processes process and in isomerization processes, use the consumption of catalyzer very large, cause containing a large amount of solvent and catalyzer in reaction product thereupon, later separation process for refining difficulty is increased.Without the need to using solvent in preparation method of the present invention, than the method more environmental protection of physical compounding, cost is cheaper.
Accompanying drawing explanation
Nothing.
Embodiment
Below in conjunction with specific embodiment in detail the present invention is described in detail, but should be understood that embodiment is only illustrative, and not restrictive.
Embodiment 1
It is in the reactor of 1000mL that 800g bridge dicyclopentadiene and 20g nickel catalyzator are added volume, stir speed (S.S.) wherein in reactor is 400rpm, and under the condition of 0.1MPa nitrogen, temperature 165 DEG C, polyreaction obtains the mixture of polymerisate bridge dicyclopentadiene and three cyclopentadiene for 10 hours;
Then by the mixture of described bridge dicyclopentadiene and three cyclopentadiene hydrogen pressure be 3.0MPa, temperature be the condition of 120 DEG C under reaction 5 hours; Under continuing to be warmed up to the condition of 165 DEG C, reaction is cooled to 25 DEG C to filter the mixtures obtaining hydrogenation rear axle type tetrahydro-dicyclopentadienes and multiple tetrahydrochysene three cyclopentadiene isomers for 10 hours;
The mixture of described bridge-type tetrahydro-dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers is moved among the glass flask of 1000ml, adds the AlCl of this mixture quality than 3% wherein
3powder, stirring reaction 14 hours under 135 DEG C of conditions, reaction terminates rear stratification, and get supernatant liquid and be separated after standing separation through washing, obtained light yellow transparent liquid rocket engine fuel 744g, rocket engine fuel total mass yield is 94.0%.
Through gas chromatographic analysis, this hydrocarbon mixture liquid rocket engine fuel is the mixture be made up of hanging type tetrahydrochysene dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers, wherein the mass percent of hanging type tetrahydrochysene dicyclopentadiene (JP-10) component is 67.6%, and the mass percent of tetrahydrochysene three cyclopentadiene component is 32.4%.Method according to GB GB2540-81 " petroleum products densitometry " measures, and the density of the hydrocarbon rocket engine fuel of this hydrocarbon mixture liquid at 20 DEG C is 0.966g/cm
3method according to GB GB2430-81 " jet fuel freeze assay method " measures, this liquid jet fuel freeze is-68 DEG C, and the method according to GB GB384-81 " petroleum products heating-value determination method " measures, and the volume calorific value of this liquid rocket engine fuel is 40.95MJ/L.
Embodiment 2-8
In embodiment 2-8, the preparation process of each embodiment is with embodiment 1, unlike the processing condition changed wherein, such as polymerization times etc., to obtain the high-density hydrocarbon mixture hydrocarbon liquid rocket engine fuel with different JP-10 and tetrahydrochysene three cyclopentadiene proportion of composing.Each embodiment processing condition are as shown in table 1:
Table 1: processing condition in embodiment 2-8
Above-described embodiment directly obtains JP-10 in rocket engine fuel preparation process simultaneously and tetrahydrochysene three cyclopentadiene hydrocarbon mixture obtains high-density hydrocarbon mixture liquid rocket engine fuel, in preparation process, directly can regulate JP-10 and the proportion of composing both tetrahydrochysene three cyclopentadiene by changing preparation condition (such as controlling polymerization time).Prepare in the performance of the high-density hydrocarbon mixture liquid rocket engine fuel obtained by the present invention and prior art after JP-10 and tetrahydrochysene three cyclopentadiene that the composite composite fuel obtained is suitable in proportion more respectively, directly can use as rocket engine fuel.
Claims (10)
1. a preparation method for hydrocarbon mixture liquid rocket engine fuel, is characterized in that, it comprises the following steps:
(1) bridge dicyclopentadiene and nickel catalyzator are added in reactor, polyreaction 6-68h under 0.1 ~ 3Mpa nitrogen, the condition of 140 ~ 250 DEG C, obtain the first mixture containing three cyclopentadiene and bridge dicyclopentadiene;
(2) by above-mentioned first mixture hydrogenation reaction 10-35h under 2 ~ 6MPa hydrogen, the condition of 100 ~ 250 DEG C, the second mixture containing bridge-type tetrahydro-dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers is obtained;
(3) in above-mentioned second mixture, add AlCl3 catalyzer, at 30 DEG C ~ 150 DEG C temperature, react the 3rd mixture obtained for 1 ~ 40 hour containing hanging type tetrahydrochysene dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers;
(4) remove the catalyzer in above-mentioned 3rd mixture, obtain described hydrocarbon mixture liquid rocket engine fuel.
2. preparation method according to claim 1, is characterized in that, the addition of described nickel catalyzator is 3% ~ 15% of bridge dicyclopentadiene weight.
3. preparation method according to claim 1, is characterized in that, the addition of described AlCl3 catalyzer is 2% ~ 25% of described second mixture weight.
4. preparation method according to claim 1, it is characterized in that, by the polymerization time in set-up procedure (1), the mass ratio of hanging type tetrahydrochysene dicyclopentadiene described in product and described multiple tetrahydrochysene three cyclopentadiene isomers is controlled 10: 90 ~ 91: 9.
5. preparation method according to claim 1, is characterized in that, after its described hydrogenation reaction be also included in step (2) terminates, by the step that the nickel catalyzator in reactant is removed.
6. the preparation method of a hydrocarbon mixture liquid rocket engine fuel, it is characterized in that, add before the described nickel catalyzator added being changed into the described hydrogenation reaction in step (2) in step (1) in the preparation method according to any one of claim 1-5.
7. a preparation method for hydrocarbon mixture liquid rocket engine fuel, is characterized in that, it comprises the following steps:
(1) hanging dicyclopentadiene and nickel catalyzator are added in reactor, polyreaction 6-68h under 0.1 ~ 3Mpa nitrogen, the condition of 140 ~ 250 DEG C, obtain the primary mixes containing three cyclopentadiene and hanging dicyclopentadiene;
(2) by above-mentioned primary mixes hydrogenation reaction 10-35h under 2 ~ 6MPa hydrogen, the condition of 100 ~ 250 DEG C, the two-stage mixture containing hanging type tetrahydrochysene dicyclopentadiene and multiple tetrahydrochysene three cyclopentadiene isomers is obtained;
(3) remove the catalyzer in above-mentioned two-stage mixture, obtain described hydrocarbon mixture liquid rocket engine fuel.
8. preparation method according to claim 7, is characterized in that, the addition of described nickel catalyzator is 3% ~ 15% of hanging dicyclopentadiene weight.
9. preparation method according to claim 7, it is characterized in that, by the polymerization time in set-up procedure (1), the mass ratio of hanging type tetrahydrochysene dicyclopentadiene described in product and described multiple tetrahydrochysene three cyclopentadiene isomers is controlled 10: 90 ~ 91: 9.
10. the preparation method of a hydrocarbon mixture liquid rocket engine fuel, it is characterized in that, add before the described nickel catalyzator added being changed into the described hydrogenation reaction in step (2) in step (1) in the preparation method according to any one of claim 7-9.
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Cited By (7)
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| CN106190354A (en) * | 2016-08-18 | 2016-12-07 | 天津大学 | A kind of complete synthesis type aviation fuel and preparation method thereof |
| CN106336920A (en) * | 2016-10-10 | 2017-01-18 | 天津大学 | High-density diesel oil and preparation method thereof |
| CN107057779A (en) * | 2016-12-27 | 2017-08-18 | 内蒙古晟源科技有限公司 | A kind of High-Density Jet |
| CN107057781A (en) * | 2016-12-27 | 2017-08-18 | 内蒙古晟源科技有限公司 | A kind of high density, high heating value jet fuel |
| CN107057780A (en) * | 2016-12-27 | 2017-08-18 | 内蒙古晟源科技有限公司 | A kind of standard diesel oil of super state VI |
| CN107879872A (en) * | 2017-11-09 | 2018-04-06 | 湖北航天化学技术研究所 | Density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method |
| CN109797015A (en) * | 2019-01-29 | 2019-05-24 | 天津大学 | Fuel containing alkyl decahydronaphthalene and alkyl diamondoid, preparation method and application thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106190354A (en) * | 2016-08-18 | 2016-12-07 | 天津大学 | A kind of complete synthesis type aviation fuel and preparation method thereof |
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| CN106336920A (en) * | 2016-10-10 | 2017-01-18 | 天津大学 | High-density diesel oil and preparation method thereof |
| CN106336920B (en) * | 2016-10-10 | 2017-12-22 | 天津大学 | A kind of high density diesel oil and preparation method thereof |
| CN107057779A (en) * | 2016-12-27 | 2017-08-18 | 内蒙古晟源科技有限公司 | A kind of High-Density Jet |
| CN107057781A (en) * | 2016-12-27 | 2017-08-18 | 内蒙古晟源科技有限公司 | A kind of high density, high heating value jet fuel |
| CN107057780A (en) * | 2016-12-27 | 2017-08-18 | 内蒙古晟源科技有限公司 | A kind of standard diesel oil of super state VI |
| CN107057780B (en) * | 2016-12-27 | 2018-09-28 | 内蒙古晟源科技有限公司 | A kind of VI standard diesel oil of super state |
| CN107879872A (en) * | 2017-11-09 | 2018-04-06 | 湖北航天化学技术研究所 | Density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method |
| CN109797015A (en) * | 2019-01-29 | 2019-05-24 | 天津大学 | Fuel containing alkyl decahydronaphthalene and alkyl diamondoid, preparation method and application thereof |
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