CN107353944B - A kind of high density cage modle heat absorbing type liquid carbon hydrogen fuel and preparation method thereof - Google Patents
A kind of high density cage modle heat absorbing type liquid carbon hydrogen fuel and preparation method thereof Download PDFInfo
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- CN107353944B CN107353944B CN201610553357.1A CN201610553357A CN107353944B CN 107353944 B CN107353944 B CN 107353944B CN 201610553357 A CN201610553357 A CN 201610553357A CN 107353944 B CN107353944 B CN 107353944B
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2072—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by condensation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
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- 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
- C10L2270/00—Specifically adapted fuels
- C10L2270/02—Specifically adapted fuels for internal combustion engines
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Abstract
A kind of high density cage modle heat absorbing type liquid carbon hydrogen fuel and preparation method thereof, using Buddha's warrior attendant alkanone and cyclopropane methyl ketone as starting material, using carbonyl reduction coupling method, one-step synthesis is obtained.The main component of the fuel is the mixture of 2- (2- cyclopropyl-vinyl)-adamantane and adamantane dimerizing olefins body.The fuel freezing point is lower than -20 DEG C, and density is 0.98 ~ 1.01 g/cm3Between, it is a kind of cage modle heat absorbing type liquid carbon hydrogen fuel of function admirable that calorific value, which is 42.7 ~ 45.0 MJ/kg,.The fuel can be used as liquid ducted rocket propulsion system or hypersonic rocket engine Endothermic Hydrocarbon Fuel or high-energy fuel additive.
Description
Technical field
The invention belongs to liquid carbon hydrogen fuel preparation technical fields, are related to a kind of novel high-density cage modle heat absorbing type liquid carbon
Hydrogen hydrocarbon fuel and its preparation, the fuel have special cagelike structure, highly dense except having when using as liquid carbon hydrogen fuel
Spend (0.98 ~ 1.01 g/cm3) and calorific value outside, also have good heat absorption capacity.
Background technique
Endothermic Hydrocarbon Fuel (Endothermic Hydrocarbon Fuel, abbreviation EHF) is a kind of novel fuel,
It can also issue biochemical reaction in gas phase condition using it other than being conducive to the physics heat sink (sensible heat and latent heat) of itself
Heat (chemistry is heat sink) is absorbed, i.e., is cracked into small molecule product before entering into the combustion chamber, cracking process absorbs heat, thus its
Cooling capacity greatly enhances.Therefore Endothermic Hydrocarbon Fuel is not only a kind of fuel of function admirable, and can satisfy high Supersonic
The cooling of fast aircraft requires, and cooling and the theory of combustion are: macromolecular hydrocarbon fuel absorbs flight system before entering combustion chamber
The heat that system generates gasifies, is cracked into small molecule again, and product enters combustion chambers burn and releases the heat of absorption, thus right
System improves the utilization rate of the energy while cooling, reduce the load of hypersonic vehicle, meet combustion chamber wall surface
With body temperature control etc. require.Since energy needed for flying is transformed by fuel, fuel energy density is bigger, then carries
Propellant gross energy just the more；If identical gross energy need to be carried, propellant energy density is big, fuel tank volume reduces, drop
The low load of aircraft, therefore, the fuel that the fixed aircraft requirements of volume use must possess higher density and volume
Calorific value, to provide more energy for aircraft.Therefore, high density Endothermic Hydrocarbon Fuel has become the heat of various countries' research and development
Point.The preparation of some polycyclic class high-density hydrocarbons of the patent reports such as patent CN101099123B, US74401837 [P],
All high density and high heating value of Special attention will be given to.Existing deficiency is that preparation process some need adds hydrogen, and synthesis cost is high, operation danger
Danger；Some need isomery, synthesis process are complex.
Summary of the invention
The purpose of the present invention is to provide a kind of high density heat absorbing type liquid carbon hydrogen fuel with special cagelike structure,
The fuel also has good heat absorption capacity, can meet the needs of punching engine is to fuel in addition to high density and calorific value.
The object of the invention is also to provide the preparation methods of above-specified high density cage modle heat absorbing type liquid carbon hydrogen fuel.
Solution of the invention is: using Buddha's warrior attendant alkanone and cyclopropane methyl ketone as starting material, using carbonyl reduction idol
Linked method is introduced into cagelike structure in liquid carbon hydrogen fuel, and one-step synthesis obtains a kind of high density cage modle liquid carbon hydrogen fuel,
Make the hydrocarbon fuel of preparation that not only there is high density and high heating value, also there is highly endothermic ability.
High density cage modle liquid carbon hydrogen fuel main component of the present invention is 2- (2- cyclopropyl-vinyl)-adamantane
Contain with the quality of the mixture of two kinds of cage compounds of adamantane dimerizing olefins body, 2- (2- cyclopropyl-vinyl)-adamantane
Amount 65 ~ 85%, the mass content 15 ~ 35% of adamantane dimerizing olefins body.
The general structure of 2- (2- cyclopropyl-vinyl)-adamantane of the present invention is C15H22, molecular weight 202；
Preparation method of the present invention, including following process: using dry tetrahydrofuran as solvent, first adding in a solvent
Entering reducing agent, reducing agent is the product Low-valent Titanium that titanium tetrachloride and zinc powder react, to titanium tetrachloride and zinc powder end of reaction, then plus
Enter pyridine, the tetrahydrofuran solution of cyclopropane methyl ketone and the tetrahydrofuran solution of Buddha's warrior attendant alkanone is then added dropwise, after being added dropwise,
Stirring 0.5 ~ 2 hour controls 80 ~ 95 DEG C of reaction temperature, is heated to reflux 12 ~ 24 hours, is then cooled to 10 DEG C hereinafter, matter is added dropwise
The solution of potassium carbonate that score is 5 ~ 20% is measured, stirring, vacuum distillation removes tetrahydrofuran；Organic extractant is added, filters, filtrate
It is washed respectively with dilute hydrochloric acid solution, distilled water, saturated brine, it is dry with anhydrous magnesium sulfate, extractant is removed, is obtained a kind of colourless
Transparent product liquid.
The tetrahydrofuran solution of cyclopropane methyl ketone of the present invention is cyclopropane methyl ketone: the mass ratio of tetrahydrofuran is 1:
0.5 ~ 1.0, the tetrahydrofuran solution of Buddha's warrior attendant alkanone is Buddha's warrior attendant alkanone: tetrahydrofuran mass ratio 1:1.2 ~ 2.0.
Reducing agent of the present invention is the product Low-valent Titanium that titanium tetrachloride and zinc powder react, and solvent is tetrahydrofuran；Reaction used
The ratio between amount of substance of object and titanium tetrachloride and zinc powder is 1:1.1:2.2；Reactant is cyclopropane methyl ketone and Buddha's warrior attendant alkanone object
The sum of the amount of matter.
Organic extractant of the present invention is one of pentane, n-hexane, hexamethylene, ether, methylene chloride.It is preferred that
Pentane.
The present invention has the advantages that
(1) synthetic method is simple, is coupled single step reaction by carbonyl reduction and obtains high density cage modle liquid carbon hydrogen fuel, no
It needs to be suitble to amplification production by hydrogenation catalyst or molecule isomery；(2) raw material used by is large chemicals, from a wealth of sources,
It is easily obtained；(3) the high density calorific value heat absorbing type liquid carbon hydrogen fuel obtained using this method, main component are 2- (2- cyclopropyl
Base-vinyl)-adamantane and adamantane dimerizing olefins body mixture, density be 0.98 ~ 1.01g/cm3Between, freezing point is low
In -20 DEG C, calorific value is 42.7 ~ 45.0 MJ/kg, and has heat absorptivity more better than general ring-type liquid hydrocarbonaceous fuel, Ke Yiman
Demand of the sufficient punching engine to fuel is a kind of cage modle liquid Endothermic Hydrocarbon Fuel of function admirable.The fuel can be used as
Liquid ducted rocket propulsion system or hypersonic rocket engine Endothermic Hydrocarbon Fuel or high-energy fuel additive.
Specific embodiment
Embodiment 1:
The mixture of tetrahydrofuran and 25 grams of zinc powders after 50 mL drying is added in the three-necked flask of 250 mL, dimension
Temperature is held at 0 DEG C hereinafter, 20 mL titanium tetrachlorides are added dropwise in 10 minutes with constant pressure funnel, is quickly stirred；After stirring 30 minutes
Then the pyridine of 5 mL is added dropwise；After being added dropwise, cooling device is removed, reflux 30 is reheated after being stirred at room temperature 30 minutes
Minute.After reflux, 0 DEG C is cooled to again, and the tetrahydrofuran that 20 grams and 38 grams Buddha's warrior attendant alkanones of cyclopropane methyl ketone are added dropwise is molten
Liquid, be added dropwise during maintain temperature 5 DEG C hereinafter, being followed by stirring for 1 hour after, remove cooling device, be heated to reflux 20 hours.Instead
After answering, heating device is removed, is cooled to 10 DEG C, it is 10% solution of potassium carbonate 150 that the mass fraction newly prepared, which is added dropwise,
Then solution is transferred to flask and carries out vacuum rotary steam, removes tetrahydrofuran by mL.100 mL are added into remaining solution again
Pentane extraction, filters, and removes solid, and filtrate uses 10% hydrochloric acid solution respectively；Distilled water；Saturated brine washing, organic phase are used
Anhydrous sodium sulfate is dry, and vacuum distillation removes pentane, obtains 13.2 grams of colorless and transparent liquid carbon hydrogen fuel.By infrared light
Spectrum test, fuel sample is in 1680 ~ 1720 m-1Between do not contain raw material carbonyl peak, in 3440 m-1Without hydroxyl hydrogen, show to fire
Expect all hydrocarbon compositions.Product carries out MS-HPLC analysis, and product is golden containing 84% 2- (2- cyclopropyl-vinyl)-
Rigid alkane (MS:m/e:202) and 15.4% adamantane dimerizing olefins body (MS:m/e 268).By test, liquid carbon hydrogen fuel
Density be 0.989 g/cm3, for freezing point lower than -20 DEG C, calorific value is 43.50 MJ/kg.
Embodiment 2:
The mixture of tetrahydrofuran and 50 grams of zinc powders after 250 mL drying is added in the three-necked flask of 500 mL, dimension
Temperature is held at 0 DEG C hereinafter, 45 mL titanium tetrachlorides are added dropwise in 50 minutes with constant pressure funnel, is quickly stirred；After stirring 30 minutes
Then the pyridine of 10 mL is added dropwise；After being added dropwise, cooling device is removed, reflux 30 is reheated after being stirred at room temperature 30 minutes
Minute.After reflux, 0 DEG C is cooled to again, and the tetrahydrofuran that 40 grams and 80 grams Buddha's warrior attendant alkanones of cyclopropane methyl ketone are added dropwise is molten
Liquid, be added dropwise during maintain temperature 5 DEG C hereinafter, being followed by stirring for 1 hour after, remove cooling device, be heated to reflux 24 hours.Instead
After answering, heating device is removed, is cooled to 10 DEG C, it is 10% solution of potassium carbonate 300 that new mass fraction of preparing, which is added dropwise,
Then solution is transferred to flask and carries out vacuum rotary steam, removes tetrahydrofuran by mL.250 mL are added into remaining solution again
Ether extraction, filters, and removes solid, and filtrate uses 10% hydrochloric acid solution respectively；Distilled water；Saturated brine washing, organic phase nothing
Aqueous sodium persulfate is dry, and vacuum distillation removes ether, obtains 25 grams of colorless and transparent liquid carbon hydrogen fuel.It is surveyed by infrared spectroscopy
Examination, fuel sample is in 1680 ~ 1720 m-1Between do not contain raw material carbonyl peak, in 3440 m-1Without hydroxyl hydrogen, show that fuel is complete
Portion is hydrocarbon composition.Product carries out MS-HPLC analysis, and product contains 76% 2- (2- cyclopropyl-vinyl)-adamantane
(MS:m/e 202) and 23.1% adamantane dimerizing olefins body (MS:m/e 268).By test, liquid carbon hydrogen fuel it is close
Degree is 0.997 g/cm3, for freezing point lower than -20 DEG C, calorific value is 43.80 MJ/kg.
Embodiment 3:
The mixture of tetrahydrofuran and 100 grams of zinc powders after 500 mL drying is added in the three-necked flask of 1L, maintains
Temperature hereinafter, 100mL titanium tetrachloride is added dropwise in 90 minutes with constant pressure funnel, is quickly stirred at 0 DEG C；Stirring is followed by for 60 minutes
Be added dropwise 30 mL pyridine；After being added dropwise, cooling device is removed, 30 points of reflux is reheated after being stirred at room temperature 30 minutes
Clock.After reflux, 10 DEG C are cooled to again, and the tetrahydrofuran that 80 grams and 150 grams Buddha's warrior attendant alkanones of cyclopropane methyl ketone are added dropwise is molten
Liquid, be added dropwise during maintain temperature 5 DEG C hereinafter, being followed by stirring for 1 hour after, remove cooling device, be heated to reflux 18 hours.Instead
After answering, heating device is removed, is cooled to 10 DEG C, it is 10% solution of potassium carbonate 600 that the mass fraction newly prepared, which is added dropwise,
Then solution is transferred to flask and carries out vacuum rotary steam, removes tetrahydrofuran by mL.500mL bis- is added into remaining solution again
Chloromethanes extraction, filters, and removes solid, and filtrate uses 10% hydrochloric acid solution respectively；Distilled water；Saturated brine washing, organic phase are used
Anhydrous sodium sulfate is dry, and vacuum distillation removes methylene chloride, obtains 48 grams of colorless and transparent liquid carbon hydrogen fuel.By infrared light
Spectrum test, fuel sample is in 1680 ~ 1720 m-1Between do not contain raw material carbonyl peak, in 3440 m-1Without hydroxyl hydrogen, show to fire
Expect all hydrocarbon compositions.Product carries out MS-HPLC analysis, and product is golden containing 67% 2- (2- cyclopropyl-vinyl)-
Rigid alkane (MS:m/e 202) and 29.8% adamantane dimerizing olefins body (MS:m/e 268).By test, liquid carbon hydrogen fuel
Density be 1.03 g/cm3, for freezing point lower than -20 DEG C, calorific value is 44.7 MJ/kg.
Claims (5)
1. a kind of high density cage modle heat absorbing type liquid carbon hydrogen fuel is adopted using Buddha's warrior attendant alkanone and cyclopropane methyl ketone as starting material
The method being coupled with carbonyl reduction, one-step synthesis obtain high density cage modle heat absorbing type liquid carbon hydrogen fuel；
The high density cage modle heat absorbing type liquid carbon hydrogen fuel main component is 2- (2- cyclopropyl-vinyl)-adamantane and gold
The mixture of two kinds of cage compounds of rigid alkane dimerizing olefins body, the mass content 65 of 2- (2- cyclopropyl-vinyl)-adamantane
~85%, the mass content 15~35% of adamantane dimerizing olefins body；
The general structure of 2- (2- cyclopropyl-the vinyl)-adamantane is C15H22, molecular weight 202；
2. the preparation method of high density cage modle heat absorbing type liquid carbon hydrogen fuel according to claim 1, including following process: with
Dry tetrahydrofuran is solvent, and reducing agent is first added in a solvent, adds pyridine, is then added dropwise the four of cyclopropane methyl ketone
The tetrahydrofuran solution of hydrogen tetrahydrofuran solution and Buddha's warrior attendant alkanone after being added dropwise, stirs 0.5~2 hour, and control reaction temperature 80~
95 DEG C, be heated to reflux 12~24 hours, be then cooled to 10 DEG C hereinafter, be added dropwise mass fraction be 5~20% solution of potassium carbonate,
Stirring, vacuum distillation remove tetrahydrofuran；Organic extractant is added, filters, filtrate uses dilute hydrochloric acid solution respectively, distilled water, satisfies
It is dry with anhydrous magnesium sulfate with salt water washing, extractant is removed, a kind of colorless and transparent product is obtained.
3. the preparation method of high density cage modle heat absorbing type liquid carbon hydrogen fuel according to claim 2, cyclopropane methyl ketone
Tetrahydrofuran solution is cyclopropane methyl ketone: the mass ratio of tetrahydrofuran is 1:0.5~1.0, and the tetrahydrofuran of Buddha's warrior attendant alkanone is molten
Liquid is Buddha's warrior attendant alkanone: tetrahydrofuran mass ratio 1:1.2~2.0.
4. the preparation method of high density cage modle heat absorbing type liquid carbon hydrogen fuel according to claim 2, the reducing agent is four
The product Low-valent Titanium of titanium chloride and zinc powder reaction, the ratio between amount of substance of reactant and titanium tetrachloride and zinc powder used are 1:1.1:
2.2；Reactant is the sum of the amount of cyclopropane methyl ketone and Buddha's warrior attendant alkanone substance.
5. the preparation method of high density cage modle heat absorbing type liquid carbon hydrogen fuel according to claim 2, the organic extractant
For one of pentane, n-hexane, hexamethylene, ether, methylene chloride.
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| RU2756770C1 (en) * | 2020-10-19 | 2021-10-05 | Акционерное Общество «Кемико» | Depressor-dispersing additive for diesel fuels and method for production thereof |
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| US10710941B1 (en) * | 2018-11-01 | 2020-07-14 | The United States Of America, As Represented By The Secretary Of The Navy | Diamondoid fuels |
| CN114437837B (en) * | 2020-10-30 | 2023-11-10 | 中国石油化工股份有限公司 | Fuel composition and application thereof |
| WO2023240380A1 (en) * | 2022-06-13 | 2023-12-21 | 天津大学滨海工业研究院有限公司 | Endothermic liquid hydrocarbon fuel and preparation method therefor |
| CN115287107B (en) * | 2022-08-31 | 2023-05-12 | 成都理工大学 | Bicycloadamantane fuel and preparation method thereof |
| WO2024071250A1 (en) * | 2022-09-27 | 2024-04-04 | 国立大学法人東海国立大学機構 | Diamondoid compound and method for producing same |
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