CN101058751A - Hanging method for preparing JP-10 jet fuel by hydrogenation of dicyclopentadiene - Google Patents
Hanging method for preparing JP-10 jet fuel by hydrogenation of dicyclopentadiene Download PDFInfo
- Publication number
- CN101058751A CN101058751A CN 200710057329 CN200710057329A CN101058751A CN 101058751 A CN101058751 A CN 101058751A CN 200710057329 CN200710057329 CN 200710057329 CN 200710057329 A CN200710057329 A CN 200710057329A CN 101058751 A CN101058751 A CN 101058751A
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- Prior art keywords
- dicyclopentadiene
- hydrogenation
- hanging
- temperature
- jet fuel
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 29
- LPSXSORODABQKT-FIRGSJFUSA-N exo-trimethylenenorbornane Chemical compound C([C@@H]1C2)C[C@@H]2[C@@H]2[C@H]1CCC2 LPSXSORODABQKT-FIRGSJFUSA-N 0.000 title claims abstract description 25
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 27
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims 2
- 239000000446 fuel Substances 0.000 abstract description 23
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 241000282326 Felis catus Species 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 230000003292 diminished effect Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000000326 densiometry Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种挂式双环戊二烯加氢制备JP－10喷气燃料的方法，属于喷气燃料的制备技术。该方法过程包括：以挂式双环戊二烯为原料，加入与原料的质量比为3％～15％的镍或钯的加氢催化剂，在氢气压力为0.5～5MPa、温度为100～160℃的条件下加氢反应5～20小时得到产物，得到的产物在压力为5～10kPa、塔釜温度为110～140℃的条件下精馏，塔顶采出50～70℃的组分，为纯度达98.5％的JP－10喷气燃料。本发明的优点在于：制备成本低、过程环保，易于大规模生产。
The invention discloses a hanging-type dicyclopentadiene hydrogenation method for preparing JP-10 jet fuel, which belongs to the preparation technology of jet fuel. The process of the method comprises: using hanging dicyclopentadiene as a raw material, adding a nickel or palladium hydrogenation catalyst with a mass ratio of 3% to 15% to the raw material, at a hydrogen pressure of 0.5 to 5MPa and a temperature of 100 to 160°C The hydrogenation reaction under the conditions of 5 to 20 hours to obtain the product, the obtained product is rectified under the conditions of the pressure of 5 to 10kPa and the temperature of the tower bottom of 110 to 140°C, and the components at 50 to 70°C are extracted from the top of the tower, which is JP-10 jet fuel with a purity of 98.5%. The invention has the advantages of low preparation cost, environment-friendly process and easy large-scale production.
Description
Technical field
The present invention relates to a kind of method of hanging dicyclopentadiene hydrogenation preparing JP-10 rocket engine fuel, belong to the technology of preparing of rocket engine fuel.
Background technology
The density of the rocket engine fuel JP-10 of Military specification MIL-P-87107C-1989 regulation is 0.935g/cm
3(16 ℃), freezing point are-78 ℃, and combustion heat value is 42.1MJ/kg, have the energy density higher than conventional hydrocarbon fuel, are a kind of rocket engine fuels of excellent performance, can be applicable to aircraft such as supersonic fighterplane, cruise missile, rocket.JP-10 is the monergol that is made of hanging type tetrahydrochysene dicyclopentadiene, and purity reaches 98.5%.Present JP-10 synthetic route is: with the bridge dicyclopentadiene is raw material, and hydrogenation becomes bridge-type tetrahydro-dicyclopentadiene, then at AlCl
3, H
2SO
4Become hanging type tetrahydrochysene dicyclopentadiene Deng isomery under the catalysis of catalyzer.The weak point of this method is: each go on foot byproduct of reaction more, need complex separation process; Acid catalysis isomery step environmental pollution is serious, and yield is low.
The applicant discloses a kind of method (CN1907927A) that is prepared hanging dicyclopentadiene by bridge dicyclopentadiene.According to aforesaid method, can prepare hanging dicyclopentadiene by bridge dicyclopentadiene on a large scale, the present invention discloses a kind of by hanging dicyclopentadiene hydrogenation preparing hanging type tetrahydrochysene dicyclopentadiene, the i.e. method of JP-10 rocket engine fuel.
Summary of the invention
The object of the present invention is to provide a kind of method of hanging dicyclopentadiene hydrogenation preparing JP-10 rocket engine fuel, this method is environmentally friendly, yield is high.
The present invention is realized by following technical proposals: a kind of method of hanging dicyclopentadiene hydrogenation preparing JP-10 rocket engine fuel is characterized in that comprising following process:
(1) with the hanging dicyclopentadiene being raw material, adding mass percent with raw material and be 3%～15% the nickel or the hydrogenation catalyst of palladium, is that 0.5～5MPa, temperature are that hydrogenation reaction obtained product in 5～20 hours under 100～160 ℃ the condition at hydrogen pressure; Described nickel catalyzator is a raney nickel catalyst or nickel catalyst carried, and wherein nickel catalyst carried carrier is γ-Al
2O
3Or SiO
2, the quality percentage composition of nickel is 10%～20%; Described palladium catalyst is a load type palladium catalyst, and its carrier is γ-Al
2O
3Or SiO
2Or activated carbon, the quality percentage composition of palladium is 0.3%～5.0%.
(2) product that step (1) is obtained carries out rectification under vacuum and purifies, and is that 5～10kPa, tower still temperature are that 110～140 ℃, tower top temperature are under 50～70 ℃ the condition at pressure, is reached 98.5% JP-10 rocket engine fuel by cat head extraction purity.
The invention has the advantages that: preparation cost is low, the process environmental protection, is easy to scale operation.Fuel purity reaches 98.5%.
Description of drawings
Fig. 1 is the gas chromatogram of 1 synthetic JP-10 of the invention process rocket engine fuel
Embodiment
The following examples have embodied the process that the present invention describes, but the present invention is not limited to these embodiment.
Embodiment 1
Step 1: the 1000g bridge dicyclopentadiene is joined in the 5000g phenylcarbinol, adding mass content in this solution is 2 of 20ppm, the 6-ditertbutylparacresol, in temperature is that 150 ℃, pressure are reaction 30 minutes under the condition of 0.9MPa, 175 ℃ of fractionation by distillation of normal pressure, obtain the quality percentage composition and the be 97% hanging dicyclopentadiene 548g of (all the other 3% be bridge dicyclopentadiene).
Step 2: with the 548g hanging dicyclopentadiene and the 64g Ni/ γ-Al of step 1 preparation
2O
3It is in the stirred autoclave of 1000mL that catalyzer adds volume, and wherein the quality percentage composition of nickel is 20% in the catalyzer, and stir speed (S.S.) is 750rpm, is that 3MPa, temperature are hydrogenation reaction 20 hours under 130 ℃ the condition at hydrogen pressure; With above-mentioned reactant filtration under diminished pressure, filtrate is added in the rectifying still, be that 10kPa, tower still temperature are rectifying under 140 ℃ the condition at pressure, by the component 490g of 65～70 ℃ of cat head extraction, purity is 98.6% JP-10 rocket engine fuel.
Method according to GB GB2540-81 " petroleum products densitometry " is measured, and the density of JP-10 rocket engine fuel is 0.935g/cm
3(16 ℃); Method according to GB GB2430-81 " rocket engine fuel kryoscopy " is measured, JP-10 rocket engine fuel freezing point is-78 ℃, method according to GB GB384-81 " petroleum products heating-value determination method " is measured, the JP-10 calorific value is 42.1MJ/kg, reaches the standard of Military specification MIL-P-87107C-1989 about the JP-10 rocket engine fuel.
Embodiment 2
Adopt the method identical to prepare hanging dicyclopentadiene with the step 1 of embodiment 1.
With hanging dicyclopentadiene 548g and 82g Ni/SiO
2It is in the stirred autoclave of 1000mL that catalyzer adds volume, and wherein the quality percentage composition of nickel is 10% in the catalyzer, and stir speed (S.S.) 800rpm is that 5MPa, temperature are hydrogenation reaction 16 hours under 160 ℃ the condition at hydrogen pressure; The reactant that obtains adds filtrate in the rectifying still through filtration under diminished pressure, is that 5kPa, tower still temperature are rectification and purification under 110 ℃ of conditions at pressure, and by the component 460g of 50～55 ℃ of cat head extraction, purity is 98.9% JP-10 rocket engine fuel.
Embodiment 3
Adopt the method identical to prepare hanging dicyclopentadiene with the step 1 of embodiment 1.
It is in the stirred autoclave of 1000mL that hanging dicyclopentadiene 548g and 54g raney nickel catalyst are added volume, and stir speed (S.S.) 950rpm is that 2.5MPa, temperature are hydrogenation reaction 11 hours under 140 ℃ the condition at hydrogen pressure; With above-mentioned reactant filtration under diminished pressure, filtrate is added in the rectifying still, be that 8kPa, tower still temperature are rectification and purification under 130 ℃ of conditions at pressure, by the component 478g of 60～65 ℃ of cat head extraction, purity is 98.5% JP-10 rocket engine fuel.
Embodiment 4
Adopt the method identical to prepare hanging dicyclopentadiene with the step 1 of embodiment 1.
With hanging dicyclopentadiene 548g and 27.4g Pd/ γ-Al
2O
3It is in the stirred autoclave of 1000mL that catalyzer adds volume, and wherein the quality percentage composition of palladium is 0.3% in the catalyzer, and stir speed (S.S.) 950rpm is that 4MPa, temperature are hydrogenation reaction 8 hours under 110 ℃ the condition at hydrogen pressure; With above-mentioned reactant filtration under diminished pressure, filtrate is added in the rectifying still, be that 7kPa, tower still temperature are rectification and purification under 125 ℃ of conditions at pressure, by the component 491g of 55～60 ℃ of cat head extraction, purity is 98.7% JP-10 rocket engine fuel.
Embodiment 5
Adopt the method identical to prepare hanging dicyclopentadiene with the step 1 of embodiment 1.
With hanging dicyclopentadiene 548g and 22g Pd/SiO
2It is in the stirred autoclave of 1000mL that catalyzer adds volume, and wherein palladium quality percentage composition is 2% in the catalyzer, and stir speed (S.S.) 950rpm is that 3MPa, temperature are hydrogenation reaction 10 hours under 100 ℃ the condition at hydrogen pressure; With above-mentioned reactant filtration under diminished pressure, filtrate is added in the rectifying still, be that 10kPa, tower still temperature are rectification and purification under 140 ℃ the condition at pressure, by the component 481g of 65～70 ℃ of cat head extraction, purity is 98.6% JP-10 rocket engine fuel.
Embodiment 6
Adopt the method identical to prepare hanging dicyclopentadiene with the step 1 of embodiment 1.
With hanging dicyclopentadiene 548g and 16.4g Pd/ activated carbon catalyst adding volume is in the stirred autoclave of 1000mL, wherein the quality percentage composition of palladium is 5% in the catalyzer, stir speed (S.S.) 750rpm is that 1.5MPa, temperature are hydrogenation reaction 5 hours under 150 ℃ the condition at hydrogen pressure; With above-mentioned reactant filtration under diminished pressure, filtrate is added in the rectifying still, be that 10kPa, tower still temperature are rectification and purification under 140 ℃ the condition at pressure, by the component 501g of 65～70 ℃ of cat head extraction, purity is 98.7% JP-10 rocket engine fuel.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100573291A CN100509717C (en) | 2007-05-14 | 2007-05-14 | Method of preparing JP-10 jet fuel by hydrogenating hanging dicyclopentadiene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100573291A CN100509717C (en) | 2007-05-14 | 2007-05-14 | Method of preparing JP-10 jet fuel by hydrogenating hanging dicyclopentadiene |
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| Publication Number | Publication Date |
|---|---|
| CN101058751A true CN101058751A (en) | 2007-10-24 |
| CN100509717C CN100509717C (en) | 2009-07-08 |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101406839B (en) * | 2008-12-08 | 2012-06-27 | 西安近代化学研究所 | Nickel catalyst for catalytic hydrogenation of dicyclopentadiene |
| CN105062579A (en) * | 2015-09-08 | 2015-11-18 | 天津大学 | Method for preparing high-density mixed hydrocarbon liquid jet fuel from dicyclopentadiene |
| CN106866345A (en) * | 2015-12-12 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method that JP-10 aviation fuel is prepared by furfuryl alcohol |
| CN110923023A (en) * | 2019-12-03 | 2020-03-27 | 西安近代化学研究所 | High-density fuel |
| CN111217663A (en) * | 2020-02-19 | 2020-06-02 | 濮阳市瑞森石油树脂有限公司 | Method for preparing tetrahydrodicyclopentadiene from dicyclopentadiene |
| CN113527031A (en) * | 2020-04-14 | 2021-10-22 | 中国石油化工股份有限公司 | Preparation method of tetrahydrodicyclopentadiene |
| CN113527028A (en) * | 2020-04-14 | 2021-10-22 | 中国石油化工股份有限公司 | Preparation method of tetrahydrodicyclopentadiene |
| CN118084604A (en) * | 2024-01-23 | 2024-05-28 | 中国人民解放军军事科学院系统工程研究院 | A method for separating and purifying hanging tetrahydrodicyclopentadiene |
-
2007
- 2007-05-14 CN CNB2007100573291A patent/CN100509717C/en active Active
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101406839B (en) * | 2008-12-08 | 2012-06-27 | 西安近代化学研究所 | Nickel catalyst for catalytic hydrogenation of dicyclopentadiene |
| CN105062579A (en) * | 2015-09-08 | 2015-11-18 | 天津大学 | Method for preparing high-density mixed hydrocarbon liquid jet fuel from dicyclopentadiene |
| CN106866345A (en) * | 2015-12-12 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method that JP-10 aviation fuel is prepared by furfuryl alcohol |
| CN106866345B (en) * | 2015-12-12 | 2020-06-02 | 中国科学院大连化学物理研究所 | Method for preparing JP-10 aviation fuel from furfuryl alcohol |
| CN110923023B (en) * | 2019-12-03 | 2021-11-23 | 西安近代化学研究所 | High-density fuel |
| CN110923023A (en) * | 2019-12-03 | 2020-03-27 | 西安近代化学研究所 | High-density fuel |
| CN111217663A (en) * | 2020-02-19 | 2020-06-02 | 濮阳市瑞森石油树脂有限公司 | Method for preparing tetrahydrodicyclopentadiene from dicyclopentadiene |
| CN113527031A (en) * | 2020-04-14 | 2021-10-22 | 中国石油化工股份有限公司 | Preparation method of tetrahydrodicyclopentadiene |
| CN113527028A (en) * | 2020-04-14 | 2021-10-22 | 中国石油化工股份有限公司 | Preparation method of tetrahydrodicyclopentadiene |
| CN113527028B (en) * | 2020-04-14 | 2023-10-10 | 中国石油化工股份有限公司 | Preparation method of tetrahydrodicyclopentadiene |
| CN113527031B (en) * | 2020-04-14 | 2024-02-20 | 中国石油化工股份有限公司 | Preparation method of tetrahydrodicyclopentadiene |
| CN118084604A (en) * | 2024-01-23 | 2024-05-28 | 中国人民解放军军事科学院系统工程研究院 | A method for separating and purifying hanging tetrahydrodicyclopentadiene |
| CN118084604B (en) * | 2024-01-23 | 2024-12-31 | 中国人民解放军军事科学院系统工程研究院 | Method for separating and purifying hanging tetrahydrodicyclopentadiene |
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| Publication number | Publication date |
|---|---|
| CN100509717C (en) | 2009-07-08 |
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