CN103289718A - Method for preparing dephenolized oil and phenolic resin through medium and low temperature coal tar oil - Google Patents
Method for preparing dephenolized oil and phenolic resin through medium and low temperature coal tar oil Download PDFInfo
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- CN103289718A CN103289718A CN2013102715606A CN201310271560A CN103289718A CN 103289718 A CN103289718 A CN 103289718A CN 2013102715606 A CN2013102715606 A CN 2013102715606A CN 201310271560 A CN201310271560 A CN 201310271560A CN 103289718 A CN103289718 A CN 103289718A
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Abstract
The invention discloses a method for preparing dephenolized oil and phenolic resin through medium and low temperature coal tar oil. The method comprises the following steps of: performing a phenolic aldehyde polymerization reaction on the coal tar oil and an aldehydes material under the catalysis of acid or alkali; washing the reaction product through benzene or methylbenzene; centrifuging to obtain supernate and precipitate; separating the supernate in a distilling way to obtain dephenolized oil of the coal tar oil and benzene or methylbenzene; and performing pressure-reduced distillation and dehydrating to obtain phenolic resin. According to the method, the medium and low temperature coal tar oil is adopted and used as a raw material for further reacting to remove a phenolic substance and gain the phenolic resin at the same time; and the method is simple in process, low in production and operation cost and remarkable in economic benefit.
Description
Technical field
The present invention relates to coal tar separation and reprocessing technical field, specifically, is the method that a kind of middle coalite tar prepares dephenolize oil and resol.
Background technology
Along with the fast development of Chinese national economy, oil reduces day by day as a kind of non-renewable natural resources, and oil has become one of key factor of restriction China Economic development.
Middle coalite tar is resulting a kind of product liquid in the middle low-temperature coal carbonization process, the complicated organic mixture that it mainly is made up of alkane, phenols (30 ~ 40%), aromatic hydrocarbon, colloid and pitch.In coalite tar similar to the oil outward appearance, all be the black thick liquid, but the composition of coal tar many than the oil complexity.
In recent years, middle coalite tar hydrogenation of total effluent made fuel oil and delayed coking-some pilot projects such as hydrogenation made fuel oil have appearred in succession, but some technical problems that these projects occur in process of construction have to be solved, particularly do not consider the phenolic compound effective elimination with relative enrichment in the middle coalite tar, existence just because of phenolic compound, not only make hydrogenation process hydrogen consumption high, and the stability of hydrogenation oil product had certain influence, make that oil product carbon residue amount increases behind the hydrogenation, flavor is smelly, variable color, to have corrodibility and a combustion case bad etc.Just remove the method for phenolic compound in the coal tar, most widely used with " acid-alkali washing method " at present.
The described method of Chinese patent CN1676583A do not utilize the phenolic compound in the raw material, but with phenols as hydrogenating materials, thereby aggravated the thermal condensation reaction of raw material in hydrogenation process; It is cost with consumption hydrogen that phenols enters hydrogenation process, finally be converted into the hydration hydrocarbon, so the phenols hydroconversion process is the depreciation process; Simultaneously just because the water-content height of the organic oxygen level height of raw material, product, in order to reduce the dividing potential drop of hydrogenation process water, be forced to adopt excessive hydrogen/stock oil volume ratio, this also makes refining and cracking process should not adopt the one-stage serial flow process, thereby has increased construction investment greatly.
Though will being rich in the cut of phenol before coal tar hydrogenating, the described method of Chinese patent CN 101037616A deviates from, the dephenolize surplus oil is carried out hydrogenation again, the phenolic compound in the coal tar is not removed fully (the organic oxygen-containing amount of deoxidation cut is 2.1%), moreover adopt the method for distillation to cut the cut that is rich in aldehydes matter, energy consumption is higher, will certainly increase construction investment greatly.
The described method of Chinese patent CN101475817A adopts the technology of " acid-alkali washing method " that the phenolic compound in the coal tar is removed, but no matter adopt alkali cleaning several times, phenolic compound in the coal tar all can have residual, and this technological process complex procedures, required equipment is various, not only increased cost of investment greatly, also can produce a large amount of trade effluents, environment has been polluted.
In sum, the method of present preparing fuel oil by coal tar hydrogenation, do not have deep the removing fully of phenolic compound of considering, the more existing phenolic compound method that removes at present, for example " acid-alkali washing method " can not remove the phenolic compound in the coal tar fully.
Summary of the invention
The object of the present invention is to provide a kind of technology middle coalite tar simple, with low cost to prepare the method for dephenolize oil and resol, the aldehydes matter that contains in the coalite tar in the utilization and the reaction of aldehyde compound generation phenol formaldehyde condensation, further isolate dephenolize oil and resol, by single step reaction, obtain dephenolize oil and resol when removing the aldehydes matter in the middle coalite tar.
The objective of the invention is to be achieved through the following technical solutions.
Coalite tar prepares the method for dephenolize oil and resol in a kind of, may further comprise the steps: at 40 ~ 180 ℃, middle coalite tar and aldehyde material are carried out the phenol formaldehyde condensation reaction in the presence of catalyzer, leave standstill after having reacted, cool off, add the extraction of benzene or toluene, solid-liquid separation obtains solid phase resol, liquid phase obtains dephenolize oil through distillation, described catalyzer is selected from organic acid, mineral acid, organic bases and mineral alkali, and described aldehyde material is selected from formaldehyde, furfural, tertiary butyl formaldehyde, phenyl aldehyde, trioxymethylene and Paraformaldehyde 96.
According to the boiling point difference of different aldehyde materials, take following two kinds of reinforced order:
1, earlier middle coalite tar and aldehyde material are mixed, heat temperature raising to 40 ~ 100 ℃ add catalyzer again and carry out the phenol formaldehyde condensation reaction, and described aldehyde material is selected from formaldehyde, furfural and tertiary butyl formaldehyde, and reaction is preferably under the protection of inert gas to be carried out.
2, earlier with middle coalite tar and catalyst mix, heat temperature raising to 110 ~ 180 ℃ add aldehyde material again and carry out the phenol formaldehyde condensation reaction, and described aldehyde material is selected from phenyl aldehyde, trioxymethylene and Paraformaldehyde 96, and reaction is preferably under the protection of inert gas to be carried out.
The mass ratio of coalite tar and aldehyde material is 1:0.3 ~ 1.2 in above-mentioned;
Above-mentioned catalyzer is selected from sulfuric acid, oxalic acid, Phenylsulfonic acid and hydrochloric acid, or is selected from sodium hydroxide, potassium hydroxide, ammoniacal liquor, zinc acetate and triethylamine, and catalyst quality is 0.5 ~ 20% of middle coalite tar consumption.
Coalite tar is the product liquid that obtains in the middle low-temperature coal carbonization process in above-mentioned, or the distillation fraction of middle coalite tar, extraction cut, column chromatography eluting fraction.
Distillation condition is 50 ~ 120 ℃, 0.001 ~ 1 MPa.
Advantage of the present invention and positively effect: coalite tar initial gross separation and reprocessing technology in the present invention relates to, the pretreatment technology of coalite tar hydrogenation made fuel oil in can be used as; The dephenolize oil purity height that the inventive method is produced, directly hydrogenation is produced oil fuel or is directly offered oil refinery factory and produces gasoline, diesel oil and kerosene etc., can reduce the hydrogen consumption in the hydrogenation process greatly, simultaneously also prevent the corrosion of raw material to equipment, avoided the shortcoming of oil quality difference behind the dephenolize coal tar hydrogenating not; The present invention is that the raw material single step reaction obtains resol when removing aldehydes matter with middle coalite tar, and technology is simple, the production run cost is low, remarkable in economical benefits.
Description of drawings
Fig. 1 is the total ions chromatogram of middle coalite tar heavy oil;
Fig. 2 is the total ions chromatogram of middle coalite tar heavy oil dephenolize oil;
Fig. 3 is the phenolic resin gel color atlas of middle coalite tar heavy oil and formaldehyde reaction preparation;
Fig. 4 is middle coalite tar heavy oil〉total ions chromatogram of 300 ℃ of cuts;
Fig. 5 is middle coalite tar heavy oil〉total ions chromatogram of 300 ℃ of distillate dephenolizing oil;
Coalite tar among Fig. 6〉300 ℃ of cuts and formaldehyde reaction preparation and the FTIR spectrogram of resol;
The total ions chromatogram of coalite tar heavy oil dephenolize oil among Fig. 7;
Coalite tar among Fig. 8〉the resol FTIR spectrogram of 300 ℃ of cuts and phenyl aldehyde prepared in reaction.
Embodiment
Further illustrate content of the present invention below in conjunction with example.
Adopt the method for phenolic aldehyde polymerization, serve as to react for phenol raw material and aldehyde material with middle coalite tar or its distillation fraction, adopting benzene or toluene is the separated from solvent reaction product, obtains dephenolize oil and resol, thereby reaches the purpose for preparing dephenolize oil and resol with middle coalite tar.In order to illustrate that the present invention is the actual effect of feedstock production dephenolize oil and resol with middle coalite tar, adopt gas chromatograph-mass spectrometer centering coalite tar and dephenolize oil to carry out compound mensuration, adopt gel chromatograph that its molecular weight is measured or adopt infrared spectrometer to carry out characteristic group's analysis for the resol that obtains.
Experimental raw is to take from the middle coalite tar heavy oil of Fugu County, northern Shensi blue charcoal factory, and the essential property that heavy oil (tar settling pond subsurface layer oil) is measured by GB sees Table 1.
Embodiment 1
The middle coalite tar 30g that takes by weighing places reactor and adds an amount of zeolite, adds the 1mL vitriol oil, and coal tar and the vitriol oil are mixed, be warming up to 80 ~ 90 ℃ then, constantly stir the formaldehyde solution that drips 27mL 37-40% down, reacted 2 ~ 3 hours, leave standstill cooling 30 minutes.Be solvent repetitive scrubbing reaction mixture with toluene, soluble part is at 90 ℃, and distillation obtains dephenolize oil under 0.01 MPa, and insoluble part obtains resol after 80 ~ 90 ℃ of underpressure distillation desolventizings; Adopt gas chromatograph-mass spectrometer that dephenolize oil is carried out compositional analysis, adopt gel chromatograph that resol is carried out molecular weight determination.
In conjunction with Fig. 1,2 and found that of table 2, be rich in phenolic compound in the northern Shensi in the coalite tar, by with formaldehyde reaction after, in dephenolize oil, do not find phenolic compound, the phenolic compound in can removing by simple phenolic aldehyde polyreaction in the coalite tar; Be found that by Fig. 3 the resol molecular weight maximum that the reaction back generates reaches 8KDa.
Embodiment 2
Coalite tar among the 500g is placed matrass and adds an amount of zeolite, slowly heat up, collect boiling range＜170 ℃, 170 ~ 210 ℃, 210 ~ 230 ℃, 230 ~ 300 ℃,
300 ℃ of cuts that each boiling range is interior.
Take by weighing 10g
300 ℃ of cuts and 7.5mL NaOH(40wt%) place flask, add 27mL formaldehyde solution (37wt%), temperature is increased to 80 ~ 90 ℃ of reaction 1.5h, obtains above oil reservoir (dephenolize oil) and the reaction mixture under water (resol and part dephenolize oil) of water in the reactor.Be solvent repetitive scrubbing reaction mixture with toluene, soluble part is incorporated dephenolize oil into, and insoluble part obtains resol after 80 ~ 90 ℃ of underpressure distillation desolventizings; Adopt gas chromatograph-mass spectrometer that dephenolize oil is carried out compositional analysis, adopt infrared spectra that resol is analyzed.
In conjunction with found that of Fig. 4, Fig. 5 and table 3, in coalite tar heavy oil behind 300 ℃ of cuts and the formaldehyde reaction, in dephenolize oil, do not find phenolic compound, coalite tar heavy oil in can removing by simple phenolic aldehyde polyreaction〉phenolic compound in 300 ℃ of cuts, and can be to heavy oil 300 ℃ of cuts play the effect of separation; Be found that middle coalite tar heavy oil by Fig. 6〉300 ℃ of cut and formaldehyde reactions, and possess the diffuse reflectance infrared spectroscopy peak of resol by the material that obtains of separated from solvent.
Embodiment 3
Take by weighing the 10g that embodiment 2 distillations obtain
300 ℃ of cuts and 5g phenyl aldehyde place flask, at N
2Protection is stirred and is warming up to 140 ℃ down, slowly adds the 1g tosic acid, reaction 4h; And then being warming up to 180 ℃ of reaction 2h, cooling obtains post reaction mixture (resol and dephenolize oil).Be solvent repetitive scrubbing reaction mixture with toluene, soluble part is incorporated dephenolize oil into, and insoluble part obtains resol after 80 ~ 90 ℃ of underpressure distillation desolventizings; Adopt gas chromatograph-mass spectrometer that dephenolize oil is carried out compositional analysis, adopt infrared spectra that resol is analyzed.
In conjunction with found that of Fig. 7, table 3 and table 4, middle coalite tar heavy oil〉after 300 ℃ of cuts and the phenyl aldehyde reaction, in dephenolize oil, do not find phenolic compound.This shows, coalite tar heavy oil in can removing by so simple phenolic aldehyde polyreaction〉phenolic compound in 300 ℃ of cuts, and can be to heavy oil 300 ℃ of cuts play the effect of separation; Be found that middle coalite tar heavy oil by Fig. 8〉300 ℃ of cuts and phenyl aldehyde reaction, and possess the diffuse reflectance infrared spectroscopy peak of resol by the material that obtains of separated from solvent.
Formaldehyde in embodiment 1 and 2 is replaced with furfural or tertiary butyl formaldehyde, the phenyl aldehyde among the embodiment 3 is replaced with Paraformaldehyde 96 or trioxymethylene, all can obtain resol and dephenolize oil.
Claims (10)
1. coalite tar prepares the method for dephenolize oil and resol in one kind, it is characterized in that: at 40 ~ 180 ℃, middle coalite tar and aldehyde material are carried out the phenol formaldehyde condensation reaction in the presence of catalyzer, leave standstill after having reacted, cool off, add the extraction of benzene or toluene, solid-liquid separation obtains solid phase resol, liquid phase obtains dephenolize oil through distillation, described catalyzer is selected from organic acid, mineral acid, organic bases and mineral alkali, and described aldehyde material is selected from formaldehyde, furfural, tertiary butyl formaldehyde, phenyl aldehyde, trioxymethylene and Paraformaldehyde 96.
2. middle coalite tar according to claim 1 prepares the method for dephenolize oil and resol, it is characterized in that: earlier middle coalite tar and aldehyde material are mixed, heat temperature raising to 40 ~ 100 ℃, add catalyzer again and carry out the phenol formaldehyde condensation reaction, described aldehyde material is selected from formaldehyde, furfural and tertiary butyl formaldehyde.
3. middle coalite tar according to claim 2 prepares the method for dephenolize oil and resol, it is characterized in that: be reflected under the protection of inert gas and carry out.
4. middle coalite tar according to claim 1 prepares the method for dephenolize oil and resol, it is characterized in that: earlier with middle coalite tar and catalyst mix, heat temperature raising to 110 ~ 180 ℃, add aldehyde material again and carry out the phenol formaldehyde condensation reaction, described aldehyde material is selected from phenyl aldehyde, trioxymethylene and Paraformaldehyde 96.
5. middle coalite tar according to claim 4 prepares the method for dephenolize oil and resol, it is characterized in that: be reflected under the protection of inert gas and carry out.
According to claim 1 to 5 one of any described in coalite tar prepare the method for dephenolize oil and resol, it is characterized in that: the mass ratio of middle coalite tar and aldehyde material is 1:0.3 ~ 1.2.
7. middle coalite tar according to claim 1 prepares the method for dephenolize oil and resol, it is characterized in that: described catalyzer is selected from sulfuric acid, oxalic acid, Phenylsulfonic acid and hydrochloric acid, or is selected from sodium hydroxide, potassium hydroxide, ammoniacal liquor, zinc acetate and triethylamine.
8. middle coalite tar according to claim 7 prepares the method for dephenolize oil and resol, and it is characterized in that: catalyst quality is 0.5 ~ 20% of middle coalite tar consumption.
9. middle coalite tar according to claim 1 prepares the method for dephenolize oil and resol, it is characterized in that: coalite tar is the product liquid that obtains in the middle low-temperature coal carbonization process in described, or the distillation fraction of middle coalite tar, extraction cut, column chromatography eluting fraction.
10. middle coalite tar according to claim 1 prepares the method for dephenolize oil and resol, and it is characterized in that: distillation condition is 50 ~ 120 ℃, 0.001 ~ 1 MPa.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755904A (en) * | 2013-12-31 | 2014-04-30 | 陕西师范大学 | Asphalt resin binder |
| CN105602596A (en) * | 2016-03-03 | 2016-05-25 | 西北大学 | Method for separating coal tar step by step based on selective reaction and solvent |
| CN106543389A (en) * | 2016-12-07 | 2017-03-29 | 西北大学 | A kind of coal tar prepares the technique and device of phenolic resin |
| CN106635129A (en) * | 2016-09-14 | 2017-05-10 | 煤炭科学技术研究院有限公司 | Three-oil mixture phenol removing method and device |
| CN106630297A (en) * | 2017-01-18 | 2017-05-10 | 上海应用技术大学 | Wet-method catalytic oxidation treatment method of vanillin production wastewater |
| CN115259133A (en) * | 2022-08-03 | 2022-11-01 | 安徽工业大学 | Preparation and application of coal tar-based phenolic carbon aerogel |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1047945A1 (en) * | 1982-02-01 | 1983-10-15 | Центральное Проектно-Конструкторское И Технологическое Бюро Министерства Автодорог Казсср | Method of producing phenophormolites |
| CN102558468A (en) * | 2011-12-29 | 2012-07-11 | 浙江省林业科学研究院 | Bamboo/wood tar-furfural thermosetting resin and preparation method thereof |
| CN102899087A (en) * | 2012-09-19 | 2013-01-30 | 王小英 | Deep processing method for medium and low temperature coal tar |
-
2013
- 2013-07-02 CN CN201310271560.6A patent/CN103289718B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1047945A1 (en) * | 1982-02-01 | 1983-10-15 | Центральное Проектно-Конструкторское И Технологическое Бюро Министерства Автодорог Казсср | Method of producing phenophormolites |
| CN102558468A (en) * | 2011-12-29 | 2012-07-11 | 浙江省林业科学研究院 | Bamboo/wood tar-furfural thermosetting resin and preparation method thereof |
| CN102899087A (en) * | 2012-09-19 | 2013-01-30 | 王小英 | Deep processing method for medium and low temperature coal tar |
Non-Patent Citations (3)
| Title |
|---|
| 北京石油学院炼制系塑料组: "低温干馏煤焦油馏分加醛直接缩合的研究", 《化工学报》 * |
| 水恒福等: "《煤焦油分离与精制》", 31 January 2007 * |
| 王立斌: "《焦化技术》", 31 May 2011 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755904A (en) * | 2013-12-31 | 2014-04-30 | 陕西师范大学 | Asphalt resin binder |
| CN103755904B (en) * | 2013-12-31 | 2015-08-19 | 陕西师范大学 | A kind of Asphalt resin binder |
| CN105602596A (en) * | 2016-03-03 | 2016-05-25 | 西北大学 | Method for separating coal tar step by step based on selective reaction and solvent |
| CN105602596B (en) * | 2016-03-03 | 2018-08-03 | 西北大学 | A method of coal tar is detached based on selective reaction-solvent step |
| CN106635129A (en) * | 2016-09-14 | 2017-05-10 | 煤炭科学技术研究院有限公司 | Three-oil mixture phenol removing method and device |
| CN106543389A (en) * | 2016-12-07 | 2017-03-29 | 西北大学 | A kind of coal tar prepares the technique and device of phenolic resin |
| CN106630297A (en) * | 2017-01-18 | 2017-05-10 | 上海应用技术大学 | Wet-method catalytic oxidation treatment method of vanillin production wastewater |
| CN115259133A (en) * | 2022-08-03 | 2022-11-01 | 安徽工业大学 | Preparation and application of coal tar-based phenolic carbon aerogel |
| CN115259133B (en) * | 2022-08-03 | 2023-12-26 | 安徽工业大学 | Preparation and application of coal tar-based phenolic carbon aerogel |
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