CN107879872A - Density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method - Google Patents

Density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method Download PDF

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CN107879872A
CN107879872A CN201711097127.XA CN201711097127A CN107879872A CN 107879872 A CN107879872 A CN 107879872A CN 201711097127 A CN201711097127 A CN 201711097127A CN 107879872 A CN107879872 A CN 107879872A
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reaction
cyclopentadiene
hydrocarbon fuel
density
liquid hydrocarbon
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CN107879872B (en
Inventor
邱贤平
朱朝阳
庞爱民
韦伟
杜利
陈克海
金凤
鲁统洁
王宏志
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Hubei Institute of Aerospace Chemical Technology
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Hubei Institute of Aerospace Chemical Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
    • C07C5/2226—Catalytic processes not covered by C07C5/23 - C07C5/31 with inorganic acids; with salt or anhydrides of acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/50—Diels-Alder conversion
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A kind of density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method, Diels-Alder addition reactions：Raw material are cyclopentadiene, 170 DEG C ~ 185 DEG C of reaction temperature, 6 ~ 24 hours reaction time；Catalytic hydrogenating reduction reacts：Hydrogenation catalyst is added, Hydrogen Vapor Pressure is 2MPa ~ 5MPa, 150 DEG C ~ 220 DEG C of reaction temperature, 8 ~ 24 hours reaction time；Molecular structure isomerization reaction：The material of self-catalysis in future hydrogenation reduction process adds solvent, AlCl3Catalyst, 25 DEG C ~ 70 DEG C of reaction temperature, 12 ~ 24 hours reaction time.The Diels-Alder addition reactions of the present invention are without the use of catalyst, and by regulating and controlling Diels-Alder reaction time and reaction temperature, can adjust the proportion of composing of such high density liquid hydrocarbon fuel component.The synthetic method craft route of the present invention is simple, and preparation cost is low, is easy to large-scale production.

Description

Density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method
Technical field
The present invention relates to a kind of density to be more than 1g/cm3High density liquid hydrocarbon fuel synthetic method, belong to new boat The technology of preparing of its aviation fuel.
Background technology
With the development of modern aerospace technology, a series of flights such as the voyages of various aircraft, the speed of a ship or plane, payload Performance is greatly improved, and this requires its used fuel to have more excellent propulsion capability.The hydrocarbon combustion of high density Material than general hydrocarbon fuel has bigger mass density and volume calorific value, is to ensure the high speed of a ship or plane of course of new aircraft, big load, far The basic fuel of the requirements such as range, high flexibility.High-density hydrocarbons generally refer to density and are more than 0.8g/cm3, composition can be with It is the mixture of pure component or a variety of hydro carbons.It is domestic since developing high density carbon hydrogen species fuel since the sixties in last century The external field achieves notable achievement, patent US [P] 4086284, US [P] 3701812, ZL 200710057328.7, ZL2013610231820.7 etc. reports hanging type tetrahydrochysene dicyclopentadiene（JP-10）, the cyclopentadiene of tetrahydrochysene three, tetrahydrochysene Fourth Ring penta The synthetic method of the high-density hydrocarbons such as diene, its synthetic route are typically added by Diels-Alder addition reactions, catalysis The techniques such as separating-purifying are carried out after hydrogen reaction, molecular structure isomerization reaction to obtain, wherein hanging type tetrahydrochysene dicyclopentadiene（JP-10, Density 0.935g/cm3）For conventional high-density hydrocarbons, U.S.'s Tomahawk cruise missile is successfully applied to.The ring penta of tetrahydrochysene three Diene, the density of tetrahydrochysene tetracyclopentadiene are high, but cryogenic property is bad, can be used as fuel complex additive.Fuel is answered With one of effective means for being improvement high-density hydrocarbons performance, document（Energy & Fuels, 1999, 13, 641 – 649) report that the new generation of high density hydrocarbon fuel RJ-7 of U.S.'s exploitation is added by the cyclopentadiene of tetrahydrochysene three, hydrogenated cyclopentadiene/indenes Compound to obtain into three kinds of thing, hanging type tetrahydrochysene dicyclopentadiene components.Domestic Zhang Xiangwen seminars are in document（Energetic material, 2009, 17(2): 157 – 160）Report using hanging type tetrahydrochysene dicyclopentadiene after purification, the cyclopentadiene of tetrahydrochysene three, tetrahydrochysene Fourth Ring Pentadiene compounded in varing proportions after fuel performance, such compounding fuel each component need be respectively synthesized, purify, lead It is caused to prepare with high costs.The present invention uses cyclopentadiene disposably to prepare a kind of density for raw material to be more than 1g/cm3Contain extension Formula tetrahydro-dicyclopentadiene, the cyclopentadiene of tetrahydrochysene three, the high density liquid hydrocarbon fuel of tetrahydrochysene tetracyclopentadiene component, are avoided Purification, molecular structure isomery when each component is prepared respectively etc. operate, synthetic route is simple, raw material be easy to get to, and Diels-Alder addition reactions are without the use of catalyst, and the solvent used can reclaim reuse, therefore such high density The preparation cost of hydrocarbon fuel is low, is easy to scale amplification.
The content of the invention
It is an object of the invention to provide a kind of density to be more than 1g/cm3High density liquid hydrocarbon fuel synthetic method.
Technical scheme includes following process：(A) Diels-Alder addition reactions：Raw material are ring penta 2 Alkene, cyclopentadiene is dissolved in into reaction dissolvent, 170 DEG C ~ 185 DEG C of reaction temperature, 6 ~ 24 hours reaction time；(B) catalytic hydrogenation is also Original reaction：Hydrogenation catalyst is added, Hydrogen Vapor Pressure is 2MPa ~ 5MPa, and 150 DEG C ~ 220 DEG C of reaction temperature, the reaction time 8 ~ 24 is small When；(C) molecular structure isomerization reaction：The material that process (B) will be come from adds solvent, AlCl3Catalyst, 25 DEG C of reaction temperature ~ 70 DEG C, 12 ~ 24 hours reaction time.
The solvent of Diels-Alder addition reactions of the present invention is one kind in n-hexane, normal heptane, normal octane, hexamethylene Or it is several, it is 0.8 that agent and the mass ratio of reaction raw materials cyclopentadiene are held in the reaction:1~3:1.
Hydrogenation catalyst is that palladium carbon hydrogenation catalyst or Raney's nickel are hydrogenated with catalytic hydrogenating reduction reaction of the present invention Catalyst, the dosage of hydrogenation catalyst are the 1% ~ 15% of raw material cyclopentadiene quality.
The catalyst of molecular structure isomerization reaction of the present invention is AlCl3, catalyst AlCl3Dosage be raw material ring penta 2 The 5% ~ 25% of alkene quality.
The solvent of molecular structure isomerization reaction of the present invention is dichloromethane or dichloroethanes, and agent and reaction are held in the reaction The mass ratio of raw material cyclopentadiene is 1:1~3:1.
The present invention is reacted and divided by Diels-Alder addition reactions, catalytic hydrogenating reduction using cyclopentadiene as raw material Minor structure isomerization reaction, which is disposably made, contains hanging type tetrahydrochysene dicyclopentadiene, the cyclopentadiene of tetrahydrochysene three and tetrahydrochysene tetracyclopentadiene The high density liquid hydrocarbon fuel of component, Diels-Alder addition reactions of the invention are without the use of catalyst, pass through control The high density liquid hydrocarbon fuel that the reaction time of Diels-Alder addition reactions and reaction temperature can regulate and control synthesis is each The proportion of composing of component.
The first step cyclopentadiene of the present invention carries out Diels-Alder addition reactions, and product is undersaturated bicyclic penta 2 Alkene, three cyclopentadiene and tetracyclopentadiene mixture；Cyclopentadiene polymer mixture is subjected to hydrogenation catalyst reaction, added The mixture of the cyclopentadiene polymer mixture of hydrogen saturation；The cyclopentadiene polymer mixture for being hydrogenated with saturation is subjected to molecule Structured catalysis isomerization reaction, obtain containing hanging type tetrahydrochysene dicyclopentadiene, the cyclopentadiene of tetrahydrochysene three and tetrahydrochysene tetracyclopentadiene component High density liquid hydrocarbon fuel.
The advantage of the invention is that：(1) raw material cyclopentadiene wide material sources, reaction dissolvent can recycle and reuse, The preparation cost of product is low, is easy to large-scale production；(2) Diels-Alder addition reactions and the experiment of the step of catalytic hydrogenation reaction two It is simple to operate in the same dicyandiamide solution reaction of same autoclave, it is easy to scale amplification；(3) this method can pass through control Reaction time of Diels-Alder addition reactions and reaction temperature regulate and control each component of the high-density hydrocarbons of synthesis Proportion of composing；(4) the synthetically prepared a kind of density of is more than 1g/cm3High density liquid hydrocarbon fuel, meet re-entry space vehicle Demand of the engine to high-density hydrocarbons.
Embodiment
Embodiment 1:
Take 100 grams of cyclopentadiene to be dissolved in 80 grams of n-hexanes and add 1L autoclaves, lead in nitrogen displacement kettle air three times, 600 revs/min, react under 170 DEG C of temperature conditionss 6 hours, reaction system is then down to room temperature, it is 10% to add 1 gram of palladium content （Mass fraction）Palladium carbon hydrogenation catalyst, air is passed through hydrogen, Hydrogen Vapor Pressure 2MPa, 800 afterwards three times in nitrogen displacement kettle Rev/min, react 20 hours under the conditions of 160 DEG C after stop being passed through hydrogen, be filtered to remove hydrogenation catalyst after being cooled to room temperature, steam Solvent hexane is removed in distillation, obtains being hydrogenated with the cyclopentadiene polymer mixture of saturation, methylene chloride 100g, molecule isomery Catalysts AlCl35 grams, 25 DEG C are reacted 24 hours, are stopped reaction and are filtered to remove solvent, obtain 96 grams of product, and product is carried out MS-HPLC analysis and characterizations, product contain hanging type tetrahydrochysene dicyclopentadiene 19%, the cyclopentadiene 57% of tetrahydrochysene three and tetrahydrochysene Fourth Ring penta 2 Alkene 24%, density during 25 DEG C of the hydrocarbon fuel is 1.002g/cm3。
Embodiment 2:
Take 100 grams of cyclopentadiene to be dissolved in 150 grams of hexamethylenes and add 1L autoclaves, lead in nitrogen displacement kettle air three times, 600 revs/min, react under 175 DEG C of temperature conditionss 12 hours, reaction system is then down to room temperature, it is 5% to add 5 grams of palladium contents （Mass fraction）Palladium carbon hydrogenation catalyst, air is passed through hydrogen, Hydrogen Vapor Pressure 3MPa, 800 afterwards three times in nitrogen displacement kettle Rev/min, react 12 hours under the conditions of 180 DEG C after stop being passed through hydrogen, be filtered to remove hydrogenation catalyst after being cooled to room temperature, steam Solvent hexamethylene is removed in distillation, obtains being hydrogenated with the cyclopentadiene polymer mixture of saturation, methylene chloride 150g, molecule isomery Catalysts AlCl315 grams, 35 DEG C are reacted 18 hours, are stopped reaction and are filtered to remove solvent, obtain 95 grams of product, and product is carried out MS-HPLC analysis and characterizations, product contain hanging type tetrahydrochysene dicyclopentadiene 16%, the cyclopentadiene 47% of tetrahydrochysene three and tetrahydrochysene Fourth Ring penta 2 Alkene 37%, density during 25 DEG C of the hydrocarbon fuel is 1.02g/cm3。
Embodiment 3:
Take 100 grams of cyclopentadiene to be dissolved in 300 grams of normal octanes and add 1L autoclaves, lead in nitrogen displacement kettle air three times, 600 revs/min, react under 185 DEG C of temperature conditionss 10 hours, reaction system is then down to room temperature, 15 grams of Raney's nickels is added and adds Hydrogen catalyst, air is passed through hydrogen, Hydrogen Vapor Pressure 5MPa, under the conditions of 800 revs/min, 170 DEG C afterwards three times in nitrogen displacement kettle Reaction stops being passed through hydrogen after 8 hours, is filtered to remove hydrogenation catalyst after being cooled to room temperature, solvent normal octane is distilled off, obtains To the cyclopentadiene polymer mixture of hydrogenation saturation, solvent dichloroethanes 300g, molecule isomerization reaction catalyst AlCl325 Gram, 70 DEG C are reacted 12 hours, are stopped reaction and are filtered to remove solvent, obtain 96 grams of product, and product carries out MS-HPLC analysis and characterizations, Product contains hanging type tetrahydrochysene dicyclopentadiene 15%, the cyclopentadiene 51% of tetrahydrochysene three and tetrahydrochysene tetracyclopentadiene 34%, the hydrocarbon fuel Density at 25 DEG C is 1.01g/cm3。
Embodiment 4:
Take 100 grams of cyclopentadiene to be dissolved in 200 grams of n-hexanes and add 1L autoclaves, lead in nitrogen displacement kettle air three times, 600 revs/min, react under 180 DEG C of temperature conditionss 24 hours, reaction system is then down to room temperature, 10 grams of Raney's nickels is added and adds Hydrogen catalyst, air is passed through hydrogen, Hydrogen Vapor Pressure 4MPa, under the conditions of 800 revs/min, 220 DEG C afterwards three times in nitrogen displacement kettle Reaction stops being passed through hydrogen after 18 hours, is filtered to remove hydrogenation catalyst after being cooled to room temperature, solvent hexane is distilled off, obtain To the cyclopentadiene polymer mixture of hydrogenation saturation, solvent dichloroethanes 200g, molecule isomerization reaction catalyst AlCl315 Gram, 55 DEG C are reacted 18 hours, are stopped reaction and are filtered to remove solvent, obtain 95 grams of product, and product carries out MS-HPLC analysis and characterizations, Product contains hanging type tetrahydrochysene dicyclopentadiene 14%, the cyclopentadiene 48% of tetrahydrochysene three and tetrahydrochysene tetracyclopentadiene 38%, the hydrocarbon fuel Density at 25 DEG C is 1.03g/cm3。
Embodiment 5:
Take 100 grams of cyclopentadiene to be dissolved in 150 grams of normal heptanes and add 1L autoclaves, lead in nitrogen displacement kettle air three times, 600 revs/min, react under 175 DEG C of temperature conditionss 22 hours, reaction system is then down to room temperature, adding 3 grams of palladium contents is 10%（Mass fraction）Palladium carbon hydrogenation catalyst, air is passed through hydrogen afterwards three times in nitrogen displacement kettle, Hydrogen Vapor Pressure 3MPa, Stop being passed through hydrogen after reacting 20 hours under the conditions of 800 revs/min, 200 DEG C, hydrogenation catalyst is filtered to remove after being cooled to room temperature Agent, solvent n-heptane is distilled off, obtains being hydrogenated with the cyclopentadiene polymer mixture of saturation, methylene chloride 150g, divide Sub- isomerization reaction catalyst AlCl310 grams, 30 DEG C are reacted 24 hours, are stopped reaction and are filtered to remove solvent, obtain 96 grams of product, produce Thing carries out MS-HPLC analysis and characterizations, and product contains hanging type tetrahydrochysene dicyclopentadiene 18%, the cyclopentadiene 48% of tetrahydrochysene three and tetrahydrochysene four Cyclopentadiene 34%, density during 25 DEG C of the hydrocarbon fuel is 1.01g/cm3。

Claims (7)

1. a kind of density is more than 1g/cm3High density liquid hydrocarbon fuel synthetic method, it is characterised in that including following process： (A) Diels-Alder addition reactions：Raw material are cyclopentadiene, and cyclopentadiene is dissolved in into reaction dissolvent, 170 DEG C of reaction temperature ~ 185 DEG C, 6 ~ 24 hours reaction time；(B) catalytic hydrogenating reduction reacts：Add hydrogenation catalyst, Hydrogen Vapor Pressure be 2MPa ~ 5MPa, 150 DEG C ~ 220 DEG C of reaction temperature, 8 ~ 24 hours reaction time；(C) molecular structure isomerization reaction：Process (B) will be come from Material adds solvent, AlCl3Catalyst, 25 DEG C ~ 70 DEG C of reaction temperature, 12 ~ 24 hours reaction time.
2. density is more than 1g/cm according to claim 13High density liquid hydrocarbon fuel synthetic method, it is characterised in that： Process (A) Diels-Alder addition reactions reaction dissolvent is n-hexane, normal heptane, normal octane, one kind in hexamethylene or several Kind, it is 0.8 that agent and the mass ratio of reaction raw materials cyclopentadiene are held in reaction:1~3:1.
3. density is more than 1g/cm according to claim 13High density liquid hydrocarbon fuel synthetic method, it is characterised in that： Process (B) hydrogenation catalyst is palladium carbon hydrogenation catalyst and Raney's nickel hydrogenation catalyst, and the dosage of hydrogenation catalyst is raw material The 1% ~ 15% of cyclopentadiene quality.
4. density is more than 1g/cm according to claim 13High density liquid hydrocarbon fuel synthetic method, it is characterised in that： The AlCl of process (C) molecular structure isomerization reaction3The dosage of catalyst is the 5% ~ 25% of raw material cyclopentadiene weight.
5. density is more than 1g/cm according to claim 13High density liquid hydrocarbon fuel synthetic method, it is characterised in that： The solvent of process (C) molecular structure isomerization reaction is dichloromethane, dichloroethanes, and agent and reaction raw materials cyclopentadiene are held in reaction Mass ratio is 1:1~3:1.
6. density is more than 1g/cm according to claim 13High density liquid hydrocarbon fuel synthetic method, it is characterised in that： Lead in nitrogen displacement kettle air in process (A), before Diels-Alder addition reactions three times.
7. density is more than 1g/cm according to claim 13High density liquid hydrocarbon fuel synthetic method, it is characterised in that： Air is three times before being passed through hydrogen in process (B), in nitrogen displacement kettle.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4086284A (en) * 1976-09-03 1978-04-25 Suntech, Inc. Isomerization of endo-tetrahydrodicyclopentadiene to a missile fuel diluent
CN104230631A (en) * 2013-06-13 2014-12-24 湖北航天化学技术研究所 Synthetic method of tetrahydrotetracyclopentadiene
CN104449818A (en) * 2013-09-22 2015-03-25 湖北航天化学技术研究所 Cyclopentadiene high-density liquid hydrocarbon fuel and synthetic method thereof
CN105062579A (en) * 2015-09-08 2015-11-18 天津大学 Method for preparing high-density mixed hydrocarbon liquid jet fuel from dicyclopentadiene

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4086284A (en) * 1976-09-03 1978-04-25 Suntech, Inc. Isomerization of endo-tetrahydrodicyclopentadiene to a missile fuel diluent
CN104230631A (en) * 2013-06-13 2014-12-24 湖北航天化学技术研究所 Synthetic method of tetrahydrotetracyclopentadiene
CN104449818A (en) * 2013-09-22 2015-03-25 湖北航天化学技术研究所 Cyclopentadiene high-density liquid hydrocarbon fuel and synthetic method thereof
CN105062579A (en) * 2015-09-08 2015-11-18 天津大学 Method for preparing high-density mixed hydrocarbon liquid jet fuel from dicyclopentadiene

Non-Patent Citations (1)

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Title
密度大于1的高密度液体碳氢燃料合成及复配研究: "王磊等", 《含能材料》 *

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