CN113896903A - Catalytic diesel oil crosslinking agent and application thereof - Google Patents
Catalytic diesel oil crosslinking agent and application thereof Download PDFInfo
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- CN113896903A CN113896903A CN202111273711.2A CN202111273711A CN113896903A CN 113896903 A CN113896903 A CN 113896903A CN 202111273711 A CN202111273711 A CN 202111273711A CN 113896903 A CN113896903 A CN 113896903A
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- 239000002283 diesel fuel Substances 0.000 title claims abstract description 119
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 80
- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 63
- 229920005989 resin Polymers 0.000 claims abstract description 55
- 239000011347 resin Substances 0.000 claims abstract description 55
- 239000003377 acid catalyst Substances 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 17
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 alcohol compound Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 17
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 15
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 10
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 229940067107 phenylethyl alcohol Drugs 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 25
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 7
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 239000003245 coal Substances 0.000 description 5
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 5
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000010426 asphalt Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种催化柴油交联剂及其应用。包括90‑98重量份的高分子醇类化合物、1‑5重量份的质子酸催化剂、1‑5重量份的小分子醇类化合物；所述的小分子醇类化合物为乙醇、丙醇和丁醇其中的一种或几种的混合。一方面充分利用了催化柴油生产COPNA树脂，另一方面提升了催化柴油的十六烷值，提高了催化柴油的利用率和附加值，使用本发明的催化柴油交联剂获得的COPNA树脂的的收率也较普通氧化交联剂高。The invention discloses a catalytic diesel crosslinking agent and its application. It includes 90-98 parts by weight of high molecular alcohol compounds, 1-5 parts by weight of protic acid catalysts, and 1-5 parts by weight of small molecular alcohol compounds; the small molecular alcohol compounds are ethanol, propanol and butanol One or a combination of them. On the one hand, the catalytic diesel oil is fully utilized to produce the COPNA resin; The yield is also higher than that of common oxidative crosslinking agents.
Description
Technical Field
The invention belongs to the technical field of cross-linking agents, and particularly relates to a catalytic diesel oil cross-linking agent and application thereof.
Background
Condensed polynuclear aromatic resins (COPNA) are thermosetting high molecular materials which are widely regarded by people and are formed by heating and condensing aromatic compounds such as naphthalene, naphthol, pyrene, anthracene and the like under the action of a cross-linking agent and a protonic acid catalyst and under the protection of nitrogen gas, however, in the prior art, heavy oil or FCC oil slurry extraction isolate, coal liquefaction high-temperature pitch, coal tar, petroleum residue and the like are mostly used for providing polycyclic aromatic hydrocarbons, and the oxidation cross-linking agents applicable to the oil products are different.
In the prior art, patent document No. 201410021186.9 discloses condensed polynuclear polycyclic aromatic hydrocarbon resins and a method for preparing the same. The method comprises the steps of deashing coal direct liquefaction residues to obtain coal direct liquefaction high-temperature asphalt, adding a cross-linking agent and a catalyst into the coal direct liquefaction high-temperature asphalt, and carrying out cross-linking polymerization reaction to obtain the condensed polynuclear polycyclic aromatic hydrocarbon resin. The cross-linking agent is one or more of terephthalyl alcohol, benzaldehyde and paraformaldehyde, and the protonic acid catalyst is p-toluenesulfonic acid and/or sulfuric acid. However, the raw material for preparing the COPNA resin is coal directly liquefied high-temperature asphalt.
In addition, along with the increasing of crude oil heaviness and deterioration and the increasing of global demand for light oil products, the technology for petroleum lighteness has received more attention, wherein the catalytic cracking process is one of the core processes for modifying residual oil and performing secondary processing on oil products in the oil refining industry, and the catalytic diesel oil is one of the main products of the catalytic cracking process, the occupation ratio in the diesel pool in China is up to 30%, the content of polycyclic aromatic hydrocarbon in the catalytic diesel oil is higher, the cetane number is lower, the light aromatic hydrocarbon is generally prepared by hydrotreating blend fuel oil or using the blend fuel oil as a raw material, but the hydrogen consumption is high, the operating conditions are harsh, and the high-content aromatic hydrocarbon component in the catalytic diesel oil cannot be effectively utilized. Therefore, there is a need to provide a low cost way to utilize catalytic diesel.
As a mode of utilizing catalytic diesel oil at low cost needs to be provided, the technical scheme of utilizing catalytic diesel oil to prepare COPNA does not appear in the prior art, and a cross-linking agent applicable to the preparation of COPNA resin by utilizing catalytic diesel oil does not exist, a corresponding solution needs to be provided.
Disclosure of Invention
In order to solve the problems in the background art, the invention provides a cross-linking agent suitable for catalyzing diesel oil to prepare COPNA resin.
A catalytic diesel oil cross-linking agent comprises 90-98 parts by weight of high molecular alcohol compounds, 1-5 parts by weight of protonic acid catalysts and 1-5 parts by weight of small molecular alcohol compounds; the small molecular alcohol compound is one or a mixture of ethanol, propanol and butanol. The high molecular alcohol compound is alcohol with carbon atom number not less than 4.
Preferably, 96-90 parts by weight of macromolecular alcohol compound, 2-5 parts by weight of protonic acid catalyst and 2-5 parts by weight of small molecular alcohol compound.
Preferably, the catalyst comprises 94-90 parts by weight of high molecular alcohol compounds, 3-5 parts by weight of protonic acid catalysts and 3-5 parts by weight of small molecular alcohol compounds.
Preferably, the catalyst comprises 94-92 parts by weight of high molecular alcohol compounds, 3-4 parts by weight of protonic acid catalysts and 3-4 parts by weight of small molecular alcohol compounds.
Preferably, the high molecular alcohol compound is one or a mixture of more of benzyl alcohol, phenethyl alcohol and terephthalyl alcohol.
Preferably, the protonic acid catalyst is one or a mixture of p-toluenesulfonic acid and lignosulfonic acid.
Preferably, the small molecular alcohol compound is one or a mixture of ethanol, propanol and butanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of (30-40) to (70-60).
Compared with the prior art, the invention has the beneficial effects that: on one hand, the catalytic diesel oil is fully utilized to produce the COPNA resin, on the other hand, the cetane number of the catalytic diesel oil is improved, the utilization rate and the additional value of the catalytic diesel oil are improved, and the yield of the COPNA resin obtained by using the catalytic diesel oil crosslinking agent is higher than that of the common oxidation crosslinking agent.
Detailed Description
The present invention is explained, but not limited to, and the technical solutions obtained in the light of the idea of the present invention should be included in the scope of protection of the present patent. It should be noted that the density of the catalytic diesel used in the examples was 870.3kg/m30.6 percent of sulfur content, and the composition comprises: 12.0% paraffin, 3.8% monocycloparaffins, 1.3% bicycloalkane, 0.7% tricycloalkane, 20.2% monocyclic aromatic hydrocarbon, 61.9% polycyclic aromatic hydrocarbon.
Example 1
A catalytic diesel oil cross-linking agent comprises 98 parts by weight of high molecular alcohol compounds, 1 part by weight of protonic acid catalysts and 1 part by weight of small molecular alcohol compounds.
Preferably, the high molecular alcohol compound is terephthalyl alcohol.
Preferably, the protic acid catalyst is p-toluenesulfonic acid.
Preferably, the small molecule alcohol compound is butanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 30: 70.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 30:70, adding the mixture into a reactor, and keeping the pressure of the reactor at 0.5MPaG, the temperature at 180 ℃ and the reaction time at 3 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 2
A catalytic diesel oil cross-linking agent comprises 96 parts by weight of high molecular alcohol compounds, 2 parts by weight of protonic acid catalysts and 1 part by weight of small molecular alcohol compounds.
Preferably, the polymer alcohol compound is benzyl alcohol.
Preferably, the protic acid catalyst is p-toluenesulfonic acid.
Preferably, the small molecule alcohol compound is propanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing a catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 33: 67.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 33:67, adding the mixture into a reactor, keeping the pressure of the reactor at 0.8MPaG, the temperature at 200 ℃ and the reaction time at 4 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 3
A catalytic diesel oil cross-linking agent comprises 94 parts by weight of high molecular alcohol compounds, 3 parts by weight of protonic acid catalysts and 3 parts by weight of small molecular alcohol compounds.
Preferably, the high molecular alcohol compound is phenethyl alcohol.
Preferably, the protic acid catalyst is p-toluenesulfonic acid.
Preferably, the small molecule alcohol compound is ethanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing a catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 35: 65.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 35:65, adding the mixture into a reactor, and keeping the pressure of the reactor at 1.2MPaG, the temperature at 220 ℃ and the reaction time at 5 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 4
A catalytic diesel oil cross-linking agent comprises 92 parts by weight of high molecular alcohol compounds, 4 parts by weight of protonic acid catalysts and 4 parts by weight of small molecular alcohol compounds.
Preferably, the polymer alcohol compound is benzyl alcohol.
Preferably, the protic acid catalyst is lignosulfonic acid.
Preferably, the small molecule alcohol compound is propanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 37: 63.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 37:63, adding the mixture into a reactor, and keeping the pressure of the reactor at 1.6MPaG, the temperature at 240 ℃ and the reaction time at 6 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 5
A catalytic diesel oil cross-linking agent comprises 90 parts by weight of high molecular alcohol compounds, 5 parts by weight of protonic acid catalysts and 5 parts by weight of small molecular alcohol compounds.
Preferably, the high molecular alcohol compound is terephthalyl alcohol.
Preferably, the protic acid catalyst is lignosulfonic acid.
Preferably, the small molecule alcohol compound is butanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 40: 60.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 40:60, adding the mixture into a reactor, keeping the pressure of the reactor at 2.0MPaG, the temperature at 260 ℃ and the reaction time at 7 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 6
A catalytic diesel oil cross-linking agent comprises 90 parts by weight of high molecular alcohol compounds, 5 parts by weight of protonic acid catalysts and 5 parts by weight of small molecular alcohol compounds.
Preferably, the polymer alcohol compound is 40 parts by weight of benzyl alcohol and 50 parts by weight of terephthalyl alcohol.
Preferably, the protonic acid catalyst is 2 parts by weight of p-methylbenzenesulfonic acid and 3 parts by weight of lignin benzenesulfonic acid.
Preferably, the small molecular alcohol compound is 1 part by weight of ethanol, 2 parts by weight of propanol and 2 parts by weight of butanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 40: 60.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 40:60, adding the mixture into a reactor, keeping the pressure of the reactor at 2.0MPaG, the temperature at 260 ℃ and the reaction time at 7 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 7
A catalytic diesel oil cross-linking agent comprises 98 parts by weight of high molecular alcohol compounds, 1 part by weight of protonic acid catalysts and 1 part by weight of small molecular alcohol compounds.
Preferably, the polymer alcohol compound is 50 parts by weight of benzyl alcohol and 48 parts by weight of phenethyl alcohol.
Preferably, the protonic acid catalyst is 0.5 parts by weight of p-toluenesulfonic acid and 0.5 parts by weight of lignosulfonic acid.
Preferably, the small molecular alcohol compound is 0.5 part by weight of ethanol and 0.5 part by weight of propanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 30: 70.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 30:70, adding the mixture into a reactor, and keeping the pressure of the reactor at 0.5MPaG, the temperature at 180 ℃ and the reaction time at 3 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Example 8
A catalytic diesel oil cross-linking agent comprises 96 parts by weight of high molecular alcohol compounds, 2 parts by weight of protonic acid catalysts and 1 part by weight of small molecular alcohol compounds.
Preferably, the high molecular alcohol compound is 26 parts by weight of benzyl alcohol, 38 parts by weight of phenethyl alcohol and 32 parts by weight of terephthalyl alcohol.
Preferably, the protonic acid catalyst is 1 part by weight of p-toluenesulfonic acid and 1 part by weight of lignosulfonic acid.
Preferably, the small molecular alcohol compound is 0.6 weight part of ethanol and 0.4 weight part of butanol.
An application of a catalytic diesel oil cross-linking agent in the process of preparing COPNA resin by catalytic diesel oil.
Preferably, the COPNA resin is prepared by mixing a catalytic diesel oil cross-linking agent and catalytic diesel oil according to the mass ratio of 33: 67.
In the process of preparing COPNA resin by catalyzing diesel oil, firstly heating the catalyzing diesel oil to 50-60 ℃, uniformly mixing a high molecular alcohol compound, a protonic acid catalyst and a small molecular alcohol compound, mixing the catalyzing diesel oil and the catalyzing diesel oil crosslinking agent prepared by the embodiment with the catalyzing diesel oil according to the agent-oil ratio of 33:67, adding the mixture into a reactor, keeping the pressure of the reactor at 0.8MPaG, the temperature at 200 ℃ and the reaction time at 4 h.
And then, leading the product out of the reactor, sending the product into a first-stage flash tower for flash evaporation treatment, separating the catalytic diesel oil from the COPNA resin under the conditions of 240 ℃ and 96kPa of vacuum degree, then washing, centrifuging, and carrying out flash evaporation treatment again to finally obtain the COPNA resin.
Comparative example 1
This comparative example, which is a comparison of example 3, uses 94 parts by weight of benzyl alcohol as a crosslinking agent, and also includes 3 parts by weight of p-toluenesulfonic acid as a protonic acid catalyst, and then prepares COPNA resin with catalytic diesel under the same process flow and process conditions.
Comparative example 2
This comparative example, which is a comparison of example 4, uses 92 parts by weight of terephthalyl alcohol as a crosslinking agent, and further includes 4 parts by weight of lignosulfonic acid as a protonic acid catalyst, and then prepares COPNA resin with catalytic diesel under the same process flow and process conditions.
The crosslinking agent components and the weight parts of the examples 1 to 8 and the comparative examples 1 and 2 are shown in Table 1, and the parameters and the yields of the COPNA resins produced by using the crosslinking agent in the examples 1 to 8 and the comparative examples 1 and 2 are shown in Table 2.
TABLE 1 Components and parts by weight
TABLE 2 relevant parameters and yields
Claims (9)
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| US20060076265A1 (en) * | 2004-10-07 | 2006-04-13 | Roberto Galiasso | Oxygen-containing diesel fuel, process and catalyst for producing same |
| CN102453227A (en) * | 2010-10-26 | 2012-05-16 | 武汉保华石化新材料开发有限公司 | Method for preparing polycyclic aromatic hydrocarbon resin |
| CN103755926A (en) * | 2014-01-16 | 2014-04-30 | 神华集团有限责任公司 | Condensed polynuclear polycyclic aromatic hydrocarbon resin and preparation method thereof |
| CN110283341A (en) * | 2019-07-02 | 2019-09-27 | 中国石油大学(华东) | Petroleum base copna resin and its preparation method and application |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060076265A1 (en) * | 2004-10-07 | 2006-04-13 | Roberto Galiasso | Oxygen-containing diesel fuel, process and catalyst for producing same |
| CN102453227A (en) * | 2010-10-26 | 2012-05-16 | 武汉保华石化新材料开发有限公司 | Method for preparing polycyclic aromatic hydrocarbon resin |
| CN103755926A (en) * | 2014-01-16 | 2014-04-30 | 神华集团有限责任公司 | Condensed polynuclear polycyclic aromatic hydrocarbon resin and preparation method thereof |
| CN110283341A (en) * | 2019-07-02 | 2019-09-27 | 中国石油大学(华东) | Petroleum base copna resin and its preparation method and application |
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