CN111088088A - Condensed ring high-density hydrocarbon fuel and preparation method thereof - Google Patents
Condensed ring high-density hydrocarbon fuel and preparation method thereof Download PDFInfo
- Publication number
- CN111088088A CN111088088A CN201911349573.4A CN201911349573A CN111088088A CN 111088088 A CN111088088 A CN 111088088A CN 201911349573 A CN201911349573 A CN 201911349573A CN 111088088 A CN111088088 A CN 111088088A
- Authority
- CN
- China
- Prior art keywords
- hydrocarbon fuel
- condensed ring
- ring high
- density hydrocarbon
- high density
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- 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
- C10L5/00—Solid fuels
- C10L5/40—Solid fuels essentially based on materials of non-mineral origin
-
- 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
- C10L2270/04—Specifically adapted fuels for turbines, planes, power generation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a condensed ring high-density hydrocarbon fuel and a preparation method thereof, wherein the hydrocarbon fuel is 9,9‘Mixtures of bisanthracene with anthracene, 9‘The weight percentage content of the bianthracene is 85-98%, the weight percentage content of the anthracene is 2-15%, the invention selects a proper solvent and is assisted by an acid regulator, and a condensed ring high-density hydrocarbon fuel is obtained by one-step reaction through a method of hydrocarbon carbonyl reduction and reduction coupling, wherein the density of the hydrocarbon fuel is 1.20-1.25g/cm3The calorific value is 46.0-49.5 MJ/kg, the high-density high-calorific-value high-stability high-temperature-resistant high.
Description
Technical Field
The invention relates to a condensed ring high-density hydrocarbon fuel and a preparation method thereof, belonging to the technical field of preparation of high-density hydrocarbon fuels.
Background
The high-density hydrocarbon fuel has good application prospect in fuel-rich solid propulsion. When used in solid propellant, it is hoped that the high density hydrocarbon fuel is cheap and easy to prepare, and has the advantages of good heat stability, high combustion efficiency and less residue. However, most of the solid high-density hydrocarbon fuels at present have the defects of multiple synthesis steps, high cost and easy sublimation. Patent 200910085439.8 and patent 200910085440.0 propose a method for synthesizing 9,9 '-bianthracene by using anthraquinone and zinc powder, but the method is mainly used for preparing 9, 9' -bianthracene as a blue light material or an intermediate of the blue light material, and the charging ratio of acetic acid and anthraquinone is too large, so that the method has the defects of high yield of unit volume reaction and low reaction efficiency, and is not suitable for industrial amplification.
Disclosure of Invention
The invention aims to overcome the defects in the prior art, and provides a preparation method of a condensed ring high-density hydrocarbon fuel, which has the advantages of high density, high heat value, high stability, simple synthesis, less solvent, high synthesis efficiency, high batch yield, low cost, mild conditions and simple treatment, and can meet the requirements of a solid hydrocarbon fuel-rich propellant on high-quality and low-cost hydrocarbon fuels.
It is another object of the present invention to provide a fused ring high density hydrocarbon fuel.
The above purpose of the invention is mainly realized by the following technical scheme:
a condensed ring high-density hydrocarbon fuel is a mixture of 9,9 '-bianthracene and anthracene, wherein the mass percentage content of the 9, 9' -bianthracene is 85-98%, and the mass percentage content of the anthracene is 2-15%.
Anthraquinone is used as a starting material, zinc is used as a reducing agent in a solution containing acid, and the fused ring high-density hydrocarbon fuel is obtained through carbonyl reduction and reduction coupling and one-step reaction.
A preparation method of a condensed ring high-density hydrocarbon fuel comprises the following steps:
adding a solvent, an acidity regulator, anthraquinone and zinc powder into a reaction vessel, adding an acid solution in batches under the reflux condition, and then stirring for 1-2 hours; and then cooling to below 5 ℃, carrying out suction filtration, removing filtrate, washing and drying the filtrate to obtain solid, namely the condensed ring high-density hydrocarbon fuel.
In the preparation method of the condensed ring high-density hydrocarbon fuel, the solvent is one or a mixture of two or more of heavy aromatic solvent oil, toluene or trimethylbenzene.
In the preparation method of the condensed ring high-density hydrocarbon fuel, the acidity regulator is acetic acid or acetic anhydride.
In the preparation method of the condensed ring high-density hydrocarbon fuel, the mesh number of the zinc powder is 50-500 meshes.
In the preparation method of the condensed ring high-density hydrocarbon fuel, the added acid solution is hydrochloric acid, and the mass concentration is 30-35%; the acid solution is added in 3-5 batches, and the adding amount is 20-30% of the total mass each time.
In the preparation method of the condensed ring high-density hydrocarbon fuel, the mass ratio of the anthraquinone to the zinc powder to the hydrochloric acid is as follows: 1: 4-6: 4 to 16.
In the preparation method of the condensed ring high-density hydrocarbon fuel, the mass ratio of the solvent, the acidity regulator, the anthraquinone and the zinc powder is as follows: 5-10: 15-25: 1: 4 to 6.
In the above method for producing a condensed ring high-density hydrocarbon fuel, either: the temperature is reduced to-15-5 ℃; the filtrate is washed with distilled water to a pH of 7.0-7.2.
A condensed ring high-density hydrocarbon fuel is prepared by the preparation method.
Compared with the prior art, the invention has the following beneficial effects:
(1) the condensed ring high-density hydrocarbon fuel is obtained through one-step reaction by selecting a proper solvent, assisting with an acid regulator and adopting a hydrocarbon carbonyl reduction and reduction coupling method, and the prepared hydrocarbon fuel not only has the advantages of high density and high calorific value and good heat stability, but also has the advantages of simple preparation, high reaction inventory and efficiency, low cost, mild reaction conditions and short reaction time, and is suitable for industrial amplification production.
(2) An aromatic hydrocarbon solvent is preferably introduced into the condensed ring high-density hydrocarbon fuel system, so that on one hand, the dispersion effect of anthraquinone is increased, the reaction efficiency is improved, and the single-batch yield is increased; on the other hand, the aromatic hydrocarbon solvent also has the function of adjusting the granularity of the product, and the granularity of the obtained fuel can be changed through the content of the solvent, so that the requirement of a propellant can be better met; the aromatic hydrocarbon solvent can be recycled.
(3) The preparation method of the invention needs less acid regulator, and reduces cost and environmental pollution.
(4) The condensed ring high-density hydrocarbon fuel obtained by the method has the advantages of high density and high calorific value, and the density is 1.20-1.25g/cm3The heat value is 46.0-49.5 MJ/kg, and in addition, the fuel has good thermal stability and excellent thermal stability which are not possessed by other high-density hydrocarbon fuels, can meet the requirements of a solid ramjet engine or high supersonic speed flying on the fuel, and is a condensed ring high-density hydrocarbon fuel with excellent performance.
(5) The synthetic method is simple, the condensed ring high-density hydrocarbon fuel is obtained through one-step reaction of carbonyl reduction and reduction coupling, the raw material source is wide, the cost is low, the operation is simple, the condition is mild, and the method is suitable for industrial amplification production; when the fuel is used in a solid ramjet rocket engine or a hypersonic rocket engine, the fuel has the advantages of high combustion efficiency and less residues.
Drawings
FIG. 1 is a DSC of a fused ring hydrocarbon fuel prepared in accordance with example 1 of the present invention;
FIG. 2 is a DSC of a fused ring hydrocarbon fuel prepared in example 2 of the present invention.
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
the invention provides a condensed ring high-density hydrocarbon fuel, which is prepared by taking anthraquinone as a starting material, taking zinc as a reducing agent in a solution containing acid, and carrying out carbonyl reduction and reduction coupling through one-step reaction. The anthracene compound is a mixture of 9,9 '-bianthracene and anthracene, wherein the mass percentage content of the 9, 9' -bianthracene is 85-98%, and the mass percentage content of the anthracene is 2-15%.
The invention provides a preparation method of a condensed ring high-density hydrocarbon fuel, which comprises the following steps:
adding solvent, acidity regulator, anthraquinone and zinc into a reaction kettle, adding acid solution in batches under the condition of reflux, and stirring for 1-2 hours after the acid is added. Then cooling to below 5 ℃, carrying out suction filtration, removing filtrate, washing the filtrate with distilled water until the pH value is 7.0-7.2, and drying to obtain solid, namely the condensed ring high-density hydrocarbon fuel.
In an optional embodiment of the present invention, the solvent is one or a mixture of two or more of heavy aromatic solvent oil, toluene or trimethylbenzene.
In an alternative embodiment of the present invention, the acidity regulator is acetic acid or acetic anhydride.
In an optional embodiment of the present invention, the mesh number of zinc is 50 to 500 meshes.
In an optional embodiment of the invention, the added acid solution is a hydrochloric acid solution, and the mass concentration is 30-35%; the hydrochloric acid solution is added in 3-5 batches, and the addition amount is 20-30% of the total mass each time.
In an optional embodiment of the invention, the mass ratio of the anthraquinone to the zinc powder to the hydrochloric acid is as follows: 1: 4-6: 4 to 16.
In an optional embodiment of the invention, the mass ratio of the solvent, the acidity regulator, the anthraquinone and the zinc powder is as follows: 5-10: 15-25: 1: 4 to 6.
In an optional embodiment of the invention, the temperature is reduced to-15 to 5 ℃; the filtrate is washed to neutrality by distilled water, and the pH value is 7.0-7.2.
Example 1
In a 100L reaction kettle, adding 15L of toluene and trimethylbenzene as solvents, 20.0L of acetic acid for adjusting acidity, 4.16 kg of anthraquinone and 5.2 kg of zinc powder (200 meshes), heating and refluxing, adding 16.0L of concentrated hydrochloric acid in 2 batches for refluxing (the concentration is 35 percent), stirring for 1 hour after the hydrochloric acid is added, cooling to-5 ℃ and filtering. The filtrate was washed with distilled water to pH 7.1 and dried to give 2.8 kg of a solid (yield 79.1%).
Through infrared spectrum test, the fuel sample is 1680-1720 m-1Does not contain carbonyl peak of raw material and is in 3440m-1The absence of hydroxyl hydrogen indicates that the fuel is entirely composed of hydrocarbons. The product was analyzed for liquid mass, and the product contained 94% of 9, 9' -bianthracene (MS:354) and 6% of anthracene (MS: 178). Thermogravimetric analysis showed that endothermic peaks typical of the melting points of anthracene and 9, 9' -bianthracene appeared at 224.0 ℃ and 311.4 ℃ (fig. 1 shows a DSC chart of the condensed ring hydrocarbon fuel prepared in example 1 of the present invention). The density of the fused ring hydrocarbon fuel is 1.24g/cm after being tested3The calorific value is 48.3 MJ/kg.
Example 2
In a 100L reaction kettle, 15L of toluene solvent, 25.0L of acid-regulated acetic acid, 8.32 kg of anthraquinone and 10.4 kg of zinc powder (40 meshes) are added, heated and refluxed, 34.0L of concentrated hydrochloric acid (the concentration is 30 percent) is added in 3 batches, after the hydrochloric acid is added, the mixture is stirred for 1.5 hours, cooled to 0 ℃ and filtered. The filtrate was washed with distilled water to pH 7.2 and dried to give 5.38 kg of a solid (yield 76%).
Through infrared spectrum test, the fuel sample is 1680-1720 m-1Does not contain carbonyl peak of raw material and is in 3440m-1The absence of hydroxyl hydrogen indicates that the fuel is entirely composed of hydrocarbons. Thermogravimetric analysis showed that endothermic peaks typical of the melting points of anthracene and 9, 9' -bianthracene appeared at 215.6 ℃ and 309.6 ℃ (fig. 2 shows a DSC chart of the condensed ring hydrocarbon fuel prepared in example 1 of the present invention). The product was analyzed for liquid mass, and contained 91% of 9, 9' -bianthracene (MS:354) and 9%Anthracene (MS: 178). The density of the condensed ring hydrocarbon fuel is 1.21g/cm after being tested3The calorific value was 47.9 MJ/kg.
Example 3
15L of toluene, 25.0L of acetic acid for acid adjustment, 8.32 kg of anthraquinone and 13 kg of zinc powder (200 mesh) are added into a 100L reaction kettle, heated and refluxed, and 45.0L of concentrated hydrochloric acid (the concentration is 35 percent) is added in 5 batches, stirred for 1.0 hour after the hydrochloric acid is added, cooled to-5 ℃ and filtered. The filtrate was washed with distilled water to pH 7.2 and dried to give 5.7 kg of a solid (yield 80.5%).
Through infrared spectrum test, the fuel sample is 1680-1720 m-1Does not contain carbonyl peak of raw material and is in 3440m-1The absence of hydroxyl hydrogen indicates that the fuel is entirely composed of hydrocarbons. The product was analyzed for liquid mass, and contained 93% of 9, 9' -bianthracene (MS:354) and 7% of anthracene (MS: 178). The density of the fused ring hydrocarbon fuel is 1.227g/cm after being tested3The calorific value was 48.1 MJ/kg.
The above description is only for the best mode of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Those skilled in the art will appreciate that the invention may be practiced without these specific details.
Claims (11)
1. A fused ring high density hydrocarbon fuel, characterized by: the hydrocarbon fuel is 9,9‘Mixtures of bisanthracene with anthracene, 9‘The mass percent of the-dianthracene is 85-98%, and the mass percent of the anthracene is 2-15%.
2. The process for producing a condensed ring high density hydrocarbon fuel as claimed in claim 1, wherein: anthraquinone is used as a starting material, zinc is used as a reducing agent in a solution containing acid, and the fused ring high-density hydrocarbon fuel is obtained through carbonyl reduction and reduction coupling through one-step reaction.
3. A preparation method of a condensed ring high-density hydrocarbon fuel is characterized by comprising the following steps: the method comprises the following steps:
adding a solvent, an acidity regulator, anthraquinone and zinc powder into a reaction vessel, adding an acid solution in batches under the reflux condition, and then stirring for 1-2 hours; and then cooling to below 5 ℃, carrying out suction filtration, removing filtrate, washing and drying the filtrate to obtain solid, namely the condensed ring high-density hydrocarbon fuel.
4. The method for producing a condensed ring high density hydrocarbon fuel according to claim 3, characterized in that: the solvent is one or a mixture of two or more of heavy aromatic solvent oil, toluene or trimethylbenzene.
5. The method for producing a condensed ring high density hydrocarbon fuel according to claim 3, characterized in that: the acidity regulator is acetic acid or acetic anhydride.
6. The method for producing a condensed ring high density hydrocarbon fuel according to claim 3, characterized in that: the mesh number of the zinc powder is 50-500 meshes.
7. The method for producing a condensed ring high density hydrocarbon fuel according to claim 3, characterized in that: the added acid solution is hydrochloric acid, and the mass concentration is 30-35%; the acid solution is added in 3-5 batches, and the adding amount is 20-30% of the total mass each time.
8. The method for producing a condensed ring high density hydrocarbon fuel according to claim 7, characterized in that: the mass ratio of the anthraquinone to the zinc powder to the hydrochloric acid is as follows: 1: 4-6: 4 to 16.
9. The method for producing a condensed ring high density hydrocarbon fuel according to claim 3, characterized in that: the mass ratio of the solvent, the acidity regulator, the anthraquinone and the zinc powder is as follows: 5-10: 15-25: 1: 4 to 6.
10. The method for producing a condensed ring high density hydrocarbon fuel according to claim 3, characterized in that: the temperature is reduced to-15-5 ℃; the filtrate is washed with distilled water to a pH of 7.0-7.2.
11. A fused ring high density hydrocarbon fuel, characterized by: the preparation method of any one of claims 3 to 10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911349573.4A CN111088088A (en) | 2019-12-24 | 2019-12-24 | Condensed ring high-density hydrocarbon fuel and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911349573.4A CN111088088A (en) | 2019-12-24 | 2019-12-24 | Condensed ring high-density hydrocarbon fuel and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111088088A true CN111088088A (en) | 2020-05-01 |
Family
ID=70398084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911349573.4A Pending CN111088088A (en) | 2019-12-24 | 2019-12-24 | Condensed ring high-density hydrocarbon fuel and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111088088A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101560137A (en) * | 2009-05-22 | 2009-10-21 | 北京阿格蕾雅科技发展有限公司 | Method for synthesizing 9,9'-bianthracene |
| JP2018115256A (en) * | 2017-01-18 | 2018-07-26 | 川崎化成工業株式会社 | Photopolymerization sensitizer having migration resistance |
| CN109384636A (en) * | 2018-12-26 | 2019-02-26 | 湖北航天化学技术研究所 | A kind of hydrocarbon fuel-rich propellant and preparation method thereof |
-
2019
- 2019-12-24 CN CN201911349573.4A patent/CN111088088A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101560137A (en) * | 2009-05-22 | 2009-10-21 | 北京阿格蕾雅科技发展有限公司 | Method for synthesizing 9,9'-bianthracene |
| JP2018115256A (en) * | 2017-01-18 | 2018-07-26 | 川崎化成工業株式会社 | Photopolymerization sensitizer having migration resistance |
| CN109384636A (en) * | 2018-12-26 | 2019-02-26 | 湖北航天化学技术研究所 | A kind of hydrocarbon fuel-rich propellant and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| 人民教育出版社高教用书编辑部: "《有机化学（下册）》", 31 January 1962, 人民教育出版社 * |
| 姚汝华等: "《微生物工程工艺原理》", 31 May 2013, 华南理工大学出版社 * |
| 库尔特.海姆等: "《化学玛奇朵》", 31 May 2011, 上海科技教育出版社 * |
| 朱洪法等: "《精细化工常用原材料手册》", 31 December 2003, 金盾出版社 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ITBO950017A1 (en) | PROCESS FOR THE PREPARATION OF BIS (2-HYDROXYETHYL) TERAPHTHALATE | |
| CN110041952B (en) | Mesophase pitch and preparation method thereof | |
| CN107163969B (en) | Method for preparing mesophase pitch from medium-temperature coal pitch | |
| CN103275754A (en) | Method for separating liquefied heavy oil and asphalt substrate from direct coal liquefaction residues | |
| CN114349674B (en) | Thiourea compound and preparation method thereof | |
| CN110041951B (en) | Needle coke and preparation method thereof | |
| CN1116386C (en) | Copolycondensation preparation of intermediate phase carbon microsphere | |
| CN111088088A (en) | Condensed ring high-density hydrocarbon fuel and preparation method thereof | |
| CN103254933A (en) | Method for separating liquefied heavy oil and asphalt substances from direct coal liquefaction residues | |
| CN111533743B (en) | Method for synthesizing trinitrobenzo [4,5] imidazo [2,1-c ] [1,2,4] triazine-4-ketone | |
| Miller et al. | The Reactivity of the Methyl Group in 2-Methyl-3-nitronaphthalene1 | |
| WO2023039940A1 (en) | Method for preparing n,n,n-tripivaloyl-1,3,5-triaminobenzene | |
| CN112079737B (en) | Preparation method of 1,4,5, 8-tetra (4-n-butylphenylamino) anthraquinone | |
| CN110092751B (en) | Synthesis method of 2-alkyl quinoline | |
| CN111018866B (en) | Cheap and efficient preparation method of benzene triacyl imide and derivatives thereof | |
| CN109503473B (en) | Synthesis method of 2-methoxy-3-amino-5-pyridine boronic acid pinacol ester and intermediate thereof | |
| KR860001855B1 (en) | A process for preparing 2-hydroxynaphthalene-3-carboxylic acid | |
| CN113292407A (en) | Production method for synthesizing anthracene-associated anthrone by solid superacid catalysis | |
| CN102924396B (en) | Method for crystal transformation from alpha-HMX to beta-HMX | |
| CN105669371A (en) | Production method of trimethylolethane | |
| CN111470935B (en) | Method for separating phenanthrene and fluorene | |
| CN1034719A (en) | A kind of method of producing sulfapyrimidine | |
| CN102993171B (en) | Method for synthesizing quinaphthalone yellow | |
| CN114591192B (en) | Preparation method of N-cyclopropylmethyl aniline compound | |
| CN113201004B (en) | Method for rapidly preparing cyclopropane derivatives based on microchannel reaction technology |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200501 |
|
| RJ01 | Rejection of invention patent application after publication |