CN103923680B - A kind of method adopting acidic ion liquid pre-treatment to improve brown coal pyrolytic tar productive rate and quality - Google Patents
A kind of method adopting acidic ion liquid pre-treatment to improve brown coal pyrolytic tar productive rate and quality Download PDFInfo
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- 239000007788 liquid Substances 0.000 title claims abstract description 57
- 238000002203 pretreatment Methods 0.000 title claims abstract description 49
- 230000002378 acidificating effect Effects 0.000 title claims abstract description 45
- 239000003077 lignite Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000197 pyrolysis Methods 0.000 claims abstract description 15
- 150000002500 ions Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012153 distilled water Substances 0.000 claims description 14
- 239000002608 ionic liquid Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 12
- 230000008020 evaporation Effects 0.000 claims description 12
- YYLLBXMSPPCVRK-UHFFFAOYSA-N 2-butyl-1-methylimidazole fluoroform Chemical compound C(F)(F)F.C(CCC)C1=NC=CN1C YYLLBXMSPPCVRK-UHFFFAOYSA-N 0.000 claims description 11
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003245 coal Substances 0.000 abstract description 59
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000000843 powder Substances 0.000 abstract 1
- 239000011269 tar Substances 0.000 description 28
- 238000005406 washing Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000012263 liquid product Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 239000000446 fuel Substances 0.000 description 5
- 239000009671 shengli Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention discloses a kind of utilize acidic ion liquid in a mild condition pre-treatment brown coal to improve its pyrolytic tar productive rate and to improve the method for oil quality, belong to brown coal technical field of comprehensive utilization.Brown coal powder and acidic ion liquid, by selecting the acidic ion liquid that efficiently can destroy weak bonding structure in brown coal, add in reactor, in a mild condition pre-treatment by the present invention; Then after utilizing water or organic solvent to be washed out by acidic ion liquid, coal sample is dry, organic solvent and acidic ion liquid reclaim Posterior circle and use.Pretreated brown coal carry out pyrolysis, and tar quality high compared to brown coal pyrolytic tar yield after the pre-treatment of raw coal acidic ion liquid significantly improves.The method technique is simple, process is clean, tar yield is high, and acidic ion liquid consumption is few and be easy to recycle.
Description
Technical field
The invention belongs to brown coal technical field of comprehensive utilization, relate in particular to a kind of acidic ion liquid pre-treatment brown coal to improve brown coal pyrolysis gained tar yield and to improve the method for tar quality.
Background technology
Low-rank coal aboundresources in China, especially the explored retained reserve of brown coal reaches 1,303 hundred million t.Coal obtaining portion can divide liquid fuel and chemical through pyrolysis, and brown coal pyrolysis not only can obtain the tar of high added value simultaneously can to brown coal upgrading; But pyrolytic process all encounters the problems such as tar yield and quality is poor, system easily blocks, following process difficulty at present.
The pre-treatment of coal is by the hydrogen richness in increase coal and improves the approach such as coal texture to reach the object improving pyrolytic process tar yield.Miura etc. adopt hydrogen supply dissolvent coal to be carried out to the method for swelling pretreatment, make pyrolysis of coal tar yield add 23%.(Energy&Fuels,1991，5(2):340-346)。The long chain alkane such as Ofosu-Asante carries out alkylation to coal, make-OH the functional group in alkyl replacement texture of coal, after finding alkylation, in pyrolysis of coal process, volatile producibility and tar yield increase (Fuel, 1989,68 (5): 567-572).Miura etc. carry out heat pre-treatment at 150-200 DEG C to coal, then carry out Pyrolysis Experiment, find to significantly improve (Energy & Fuels, 1987,1 (1): 84-88) because thermal treatment makes the tar yield of pyrolysis of coal.The hydropyrolysis to Lingwu, Ningxia coal such as Chen Haokan can make tar yield compare inert atmosphere to improve 2 times, and the yield of BTX and PCX increases by 4 times and 2 times (chemistry of fuel journal, 1997,25 (1): 49-54) respectively.The essence of pyrolysis of coal process is that the reaction (comprising polycondensation) that covalent linkage dissociating and recombinating in thermal field, the covalent linkage forming texture of coal dissociates between the free radical that produces forms dissimilar product (gas, liquid, solid) process, in coal the kind of weak covalent linkage, quantity and distribution and pyrolytical condition determine Kinds of Free Radicals that pyrolysis produces, quantity and between reaction, and the reaction between these free radicals determines the productive rate of pyrolytic tar, quality and stability thereof.Patent (application number 201310489900.2) discloses a kind of ionic liquid pretreatment to improve the method for pyrolysis of coal tar yield, this method ionic liquid used consumption causes greatly process economics poor, does not importantly show ionic liquid physical efficiency used and improves tar quality.
Summary of the invention
For overcoming the deficiencies in the prior art, the object of this invention is to provide a kind of method of acidic ion liquid pre-treatment brown coal, also improving the quality of tar to improving brown coal pyrolysis gained tar yield simultaneously.
To achieve these goals, the present invention is achieved by the following technical programs.
The invention provides a kind of method utilizing acidic ion liquid pre-treatment to improve brown coal pyrolytic tar productive rate and quality, the method concrete steps are as follows:
(1) acidic ion liquid that efficiently can destroy weak bonding structure in brown coal is selected, brown coal and ionic liquid are joined reactor, wherein the mass ratio of ionic liquid and brown coal is 1:1 ~ 50, and described acidic ion liquid is 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate bonding structure weak in brown coal to better destructiveness;
(2) the mixture heating brown coal of step (1) and acidic ion liquid formed, temperature control in room temperature ~ 300 DEG C, and pre-treatment 0.5 ~ 5h, naturally cools to room temperature after pre-treatment terminates;
(3) the acidic ion liquid solvent in step (2) reaction gained mixture is washed out, then by evaporation solvent-recoverable and ionic liquid, ionic liquid and solvent can be recycled, and described solvent is distilled water, methyl alcohol, ethanol or acetone;
(4) brown coal drying after step (3) being processed, in order to pyrolysis.
As one optimization, the ionic liquid in described step (1) and the mass ratio of brown coal are 1:40, the pre-treatment 4h at 250 DEG C of the mixture in described step (2).
Compared with prior art, the method that under mild conditions provided by the invention, brown coal improve brown coal pyrolytic process tar yield and quality through acidic ion liquid pre-treatment has the following advantages:
1, present method acidic ion liquid used not only can dissolve coal, have katalysis can the pyrolysis of catalysis coal simultaneously, therefore not only can improve pyrolytic tar yield with a small amount of acidic ion liquid pre-treatment brown coal, and significantly can improve the quality (can high yield obtain tar light oil) of pyrolytic tar;
2, present method pretreatment temperature low (room temperature ~ 300 DEG C), process stabilizing, be easy to control and simple to operate;
3, the acidic ion liquid in the present invention, water and organic solvent can be recycled, therefore effectively improve the economy of process.
Embodiment
Below in conjunction with specific embodiment in detail the present invention is described in detail, but the present invention is not limited to following embodiment.
Embodiment 1
The cylinder lattice of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate and 3g that take 3g to strangle after brown coal mixing pre-treatment 30min at 200 DEG C, remove acidic ion liquid with distilled water wash after end, distilled water and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 75% compared to raw coal, each component productivity ratio raw coal improve 80%, 65%, 35% respectively.
Embodiment 2
The cylinder lattice of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate and 90g that take 3g to strangle after brown coal mixing pre-treatment 120min at temperature 200 DEG C, remove acidic ion liquid by methanol wash after end, methyl alcohol and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 75% compared to raw coal, each component productivity ratio raw coal improve 90%, 80%, 55% respectively.
Embodiment 3
To take after the Shengli Brown mixing of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate of 3g and 3g pre-treatment 90min at temperature 100 DEG C, remove acidic ion liquid by washing with alcohol after end, ethanol and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 45% compared to raw coal, each component productivity ratio raw coal improve 50%, 45%, 35% respectively.
Embodiment 4
The cylinder lattice of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate and 30g that take 3g to strangle after brown coal mixing pre-treatment 60min at temperature 150 DEG C, remove acidic ion liquid with distilled water wash after end, distilled water and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 55% compared to raw coal, each component productivity ratio raw coal improve 65%, 60%, 50% respectively.
Embodiment 5
At temperature 200 DEG C, 180min is extracted after taking the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate of 3g and the Shengli Brown mixing of 30g, remove acidic ion liquid with distilled water wash after end, distilled water and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 80% compared to raw coal, each component productivity ratio raw coal improve 70%, 85%, 70% respectively.
Embodiment 6
To take after the Shengli Brown mixing of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate of 3g and 120g pre-treatment 240min at temperature 250 DEG C, remove acidic ion liquid with distilled water wash after end, distilled water and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 115% compared to raw coal, each component productivity ratio raw coal improve 90%, 100%, 90% respectively.
Embodiment 7
The cylinder lattice of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate and 30g that take 3g to strangle after brown coal mixing pre-treatment 60min under room temperature, remove acidic ion liquid with distilled water wash after end, distilled water and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 30% compared to raw coal, each component productivity ratio raw coal improve 30%, 20%, 40% respectively.
Embodiment 8
To take after the Shengli Brown mixing of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate of 3g and 15g pre-treatment 150min at temperature 180 DEG C, remove acidic ion liquid with distilled water wash after end, distilled water and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 70% compared to raw coal, each component productivity ratio raw coal improve 70%, 75%, 60% respectively.
Embodiment 9
The cylinder lattice of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate and 30g that take 3g to strangle after brown coal mixing pre-treatment 60min under temperature 50 C, remove acidic ion liquid with washing with acetone after end, acetone and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 45% compared to raw coal, each component productivity ratio raw coal improve 50%, 50%, 40% respectively.
Embodiment 10
To take after the Shengli Brown mixing of the 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate of 3g and 150g pre-treatment 90min at temperature 280 DEG C, remove acidic ion liquid by washing with alcohol after end, ethanol and acidic ion liquid mixture be can be recycled by evaporation recovery.Repeatedly washing after by coal sample after pre-treatment in drying for standby.After taking pre-treatment, coal sample 3g is placed in fixed-bed reactor.Pyrolytical condition is nitrogen atmosphere, and flow velocity is 100ml/min, is heated to 800 DEG C by room temperature, and temperature rise rate is 10 DEG C/min, collects product liquid with cold-trap.The tar collected obtains aliphatic hydrocarbon, aromatic hydrocarbon, phenolic component respectively by column chromatography for separation.Find liquid product yield improve 95% compared to raw coal, each component productivity ratio raw coal improve 70%, 85%, 55% respectively.
Claims (2)
1. adopt acidic ion liquid pre-treatment to improve a method for brown coal pyrolytic tar productive rate and quality, it is characterized in that, the method concrete steps are as follows:
(1) brown coal and ionic liquid are joined reactor, wherein the mass ratio of ionic liquid and brown coal is 1:1 ~ 50, and described acidic ion liquid is 1-sulfonic acid butyl-3-Methylimidazole fluoroform sulphonate;
(2) the mixture heating brown coal of step (1) and acidic ion liquid formed, temperature control in room temperature ~ 300 DEG C, and pre-treatment 0.5 ~ 5h, naturally cools to room temperature after pre-treatment terminates;
(3) the acidic ion liquid solvent in step (2) reaction gained mixture is washed out, then by evaporation solvent-recoverable and ionic liquid, ionic liquid and solvent can be recycled, and described solvent is distilled water, methyl alcohol, ethanol or acetone;
(4) brown coal drying after step (3) being processed, in order to pyrolysis.
2. a kind of method adopting acidic ion liquid pre-treatment to improve brown coal pyrolytic tar productive rate and quality as claimed in claim 1, it is characterized in that, ionic liquid in described step (1) and the mass ratio of brown coal are 1:40, the pre-treatment 4h at 250 DEG C of the mixture in described step (2).
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| CN105368468B (en) * | 2015-12-07 | 2017-09-15 | 安徽工业大学 | A kind of method that acidic ion liquid pretreatment improves lignin pyrolytic tar yield and quality |
| WO2017132900A1 (en) | 2016-02-03 | 2017-08-10 | 太原理工大学 | Composite catalyst for coal pyrolysis and using method therefor |
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| CN102134502A (en) * | 2011-01-22 | 2011-07-27 | 安徽工业大学 | Method for depolymerizing lignite by using ionic liquid |
| CN103525500A (en) * | 2013-10-28 | 2014-01-22 | 安徽工业大学 | Method for depolymerization of low-middle rank coal by cosolvent |
| CN103525443A (en) * | 2013-10-18 | 2014-01-22 | 安徽工业大学 | Method for improving lignite pyrolysis tar yield by use of ionic liquid pretreatment |
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| CN102134502A (en) * | 2011-01-22 | 2011-07-27 | 安徽工业大学 | Method for depolymerizing lignite by using ionic liquid |
| CN103525443A (en) * | 2013-10-18 | 2014-01-22 | 安徽工业大学 | Method for improving lignite pyrolysis tar yield by use of ionic liquid pretreatment |
| CN103525500A (en) * | 2013-10-28 | 2014-01-22 | 安徽工业大学 | Method for depolymerization of low-middle rank coal by cosolvent |
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| 提高加氢热解焦油产量的途径分析;廖洪强等;《化工进展》;19961231(第6期);第19-23页 * |
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