CN105367714A - Method for preparing hydrogenated DCPD resin - Google Patents

Method for preparing hydrogenated DCPD resin Download PDF

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CN105367714A
CN105367714A CN201510885167.5A CN201510885167A CN105367714A CN 105367714 A CN105367714 A CN 105367714A CN 201510885167 A CN201510885167 A CN 201510885167A CN 105367714 A CN105367714 A CN 105367714A
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catalyst
resin
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hydrogenation
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CN105367714B (en
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梁长海
李闯
邸鑫
殷东东
张亮亮
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Dalian University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/04—Reduction, e.g. hydrogenation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The present invention discloses a method for preparing hydrogenated DCPD resin, and belongs to the technical field of resin hydrogenation. With a loaded Ni/ZnO-SiO2 catalyst as a pre-hydrogenating catalyst and an eggshell-type Pd catalyst as a hydrogenating and decolorizing catalyst, a two-stage fixed bed continuous hydrotreating way is used to perform a hydrogenating reaction on the resin. For the prepared hydrogenated DCPD resin, resin hue is improved to water white and the resin has good thermal stability. The method provided by the invention has a simple process, high catalyst activity and good stability, improves the chromaticity of the resin, improves the thermal stability thereof and reduces a softening point slightly, so that the method has good economic benefits and industrial application prospects.

Description

A kind of method preparing drogenated DCPD resin
Technical field
The invention belongs to Hydrogenation Technology of Petroleum Resin field, relate to the method for a kind of Hydrogenation for the high-grade resin of colorless and odorless good thermal stability, be specifically related to a kind of method preparing drogenated DCPD resin.
Background technology
Conventional resins is micro-Huang or brown due to outward appearance, greatly limit its application.And its degree of unsaturation reduces greatly after hydrogenation modification, resin becomes colourless, without special odor, the performance such as binding property, stability all increases, and has widened its Application Areas further.Compare in recent years it is emphasised that produce weather-proof resin, low viscosity resin, the copolymer resin of high softening-point, what stress in particular is the hydrogenated resin that look shallow.Hydrogenation modification is petroleum resin modified important method.DCPD resin can be used for producing high-grade bronze, silver ink, ink vehicles and link agent etc.For petroleum resin, the DCPD petroleum resin molecular weight especially with ring texture is large, and polymer molecule stretches at catalyst surface, defines high steric hindrance, and its molecular structure determines that hydrogenation of petroleum resin difficulty is large.The operational condition of Petroleum Resin Hydrogenation Process design is general harsher, and its technology category has difference according to the difference of industrial scale and product requirement.The representative of current foreign oil adding hydrogen into resin modification has the companies such as american exxon, Yi Siman, Japanese waste river and Japanese bright dipping.Petroleum resin after current hydrogenation modification are more and more subject to market and welcome, and compared with can only selling for the situation of 7000-8000 yuan/ton with the low side resin of domestic production, the contour quality product of hydrogenated petroleum resin has sold for 18000 yuan/ton.Catalyzer is the key of hydrogenated petroleum resin technology, external use palladium series catalyst and nickel catalyst mostly, the developing direction of hydrogenation catalyst improves the activity of catalyzer, stability, extending catalyst life-span, minimizing side reaction and suitably reduces manufacturing cost from now on.China should accelerate the research of hydrogenation of petroleum resin catalyzer and the paces of hydrogenation catalyst production domesticization, promotes the popularization of hydrogenated petroleum resin technology and the reduction of product cost further.
For abundant resin recycling problem, we successfully develop with loading type Ni/ZnO-SiO 2catalyzer is as catalyst for pre-hydrogenation, eggshell type Pd catalyst to decolour catalyzer as hydrogenation, and adopt two sections of fixed bed continuous hydrogenation modes to carry out hydrogenation reaction to resin, obtained drogenated DCPD resin form and aspect are improved to water-white, and there is good thermostability, softening temperature reduces seldom.Following known technology, all comes with some shortcomings:
Chinese patent, publication number: CN1189493C, introduces the hydrogenation catalyst for the preparation of dicyclopentadiene hydrogenated petroleum resin, add Pt in catalyzer, expensive, the softening temperature of the product obtained reduces serious, and carry out in a kettle., catalyzer difficulty is separated, and has catalyst residue in resin.
Chinese patent, publication number: CN1189494C, describes a kind of method of dicyclopentadiene hydrogenated petroleum resin, and it is tank reactor, and catalyzer difficulty is separated, and have catalyst residue in resin, catalyzer price is high.
Chinese patent, publication number: CN103360547B, introduces dicyclopentadiene hydrogenated petroleum resin production system and method, although describe whole adding hydrogen into resin process, but still is still reaction, and catalyzer difficulty is separated, and has catalyst residue in resin.
Chinese patent, publication number: CN101157029A, introduces a kind of dicyclopentadiene hydrogenation special-purpose catalyzer and preparation method thereof, adds Pt in catalyzer, expensive.
Chinese patent, publication number: CN102558444B, introduces a kind of method preparing dicyclopentadiene hydrogenated petroleum resin, and reaction process is still reaction, and catalyzer difficulty is separated, and has catalyst residue in resin.
Summary of the invention
The invention provides a kind of method preparing drogenated DCPD resin, the product specification solved in resin transfer process is low, the problems such as catalyzer easy in inactivation and deficiency in economic performance.Wide scope of material of the present invention, with high-grade drogenated DCPD resin for target product, improve resin colourity, improve thermostability, and resin softening point rate slightly reduces, product yield significantly improves.
Technical scheme of the present invention is as follows:
The method is using Ni/ZnO catalyzer as hydrogenation adsorption desulfurize catalyst, eggshell type Pd catalyst to decolour catalyzer as hydrogenation, adopts two sections of fixed bed hydrogenation modes to carry out hydrogenation reaction to resin, obtained hydrogenated resin, resin form and aspect are improved to water-white, and softening temperature slightly reduces.Step is as follows:
Prepare a method for drogenated DCPD resin, dissolved in dissolving tower by DCPD resin with solvent, wherein, the mass percent of DCPD resin is 15%-40%; Enter again and be equipped with in the removal of impurities reactor of sorbent material, removing colloid; Then mix the pre-hydrotreating reaction tower injecting and hydrogenation adsorption desulfurize catalyst is housed with hydrogen, hydrogenation adsorption desulfurize catalyst removes sulphur, chlorine/fluorine and diene in DCPD resin, temperature of reaction 200-260 DEG C, hydrogen partial pressure 2-8MPa, volume space velocity 1-4h -1, hydrogen and DCPD resin solution volume ratio 100-300:1, obtain the DCPD resin solution after pre-hydrogenation; DCPD resin solution after pre-hydrogenation enters knockout drum, hydrogen enters water wash column, and the hydrogen after washing enters pre-hydrotreating reaction tower again, and liquid directly enters bleaching tower, carry out hydrogenation decolouring, temperature of reaction 240-320 DEG C, hydrogen partial pressure 8-18MPa, volume space velocity 0.4-1.6h -1, hydrogen and DCPD resin solution volume ratio 200-600:1; The hydrogenation catalyzer used that decolours is eggshell type Pd catalyst; Resin solution after hydrogenation decolouring injects desolventizing tower, and through air distillation, the product solvent cycle that tower top distills out dissolves petroleum resin again, and bottom product enters volatilization tower; Volatilization tower negative-pressure operation, volatilization tower tower top goes out the high boiling point organic compound that the resin cracking of hydrogenation decolorization PetroChina Company Limited. produces, and go out hydrogenation resin at the bottom of volatilization tower tower, resin form and aspect are improved to water white.
Described solvent is one or more mixing in hexanaphthene, normal heptane, n-decane, methylcyclohexane, dimethyl cyclohexane, trimethyl-cyclohexane, perhydronaphthalene.
Described sorbent material is the Al of central hole structure 2o 3, mesopore volume accounts for more than 80% of total pore volume, and its pore size distribution is at 30-50nm.
Described hydrogenation adsorption desulfurize catalyst is Ni/ZnO-SiO 2catalyzer, wherein Ni content is Ni/ZnO-SiO 220% ~ 40% of catalyst quality, ZnO content is Ni/ZnO-SiO 215% ~ 25%, SiO of catalyst quality 2content is Ni/ZnO-SiO 235% ~ 65% of catalyst quality.
The carrier of described eggshell type Pd catalyst is SiO 2, Al 2o 3, Al 2o 3-TiO 2or SiO 2-Al 2o 3, Pd content is 0.3% ~ 1.0% of eggshell type Pd catalyst quality.
Beneficial effect of the present invention: the adsorption-edulcoration that the present invention relates to, pre-hydrogenation, gas washing, hydrogenation decolouring, desolventizing and devolatilization operate continuously.Owing to using two-stage hydrogenation method in method provided by the invention, improve reactive behavior and selectivity and anti-impurity ability, the inventive method is for the wide adaptability of DCPD resin raw material, adopt the DCPD resin that thermopolymerization or catalyzed polymerization obtain, no matter foreign matter content height in resin solution, especially in resin solution sulphur or fluorine/cl content higher time, method provided by the invention all can be adopted to carry out two step hydrotreatments, obtain high performance drogenated DCPD resin.By one section of pre-hydrogenation, hydrogenation adsorption desulfurize catalyst removes sulphur, chlorine/fluorine and diene in resin, and effectively protect the precious metals pd catalyzer of secondary hydrogenation, catalyst life is greatly improved.Thus the present invention has technique simply, and catalyst activity is high, good stability, improves resin colourity, improves resin thermostability, and its softening temperature slightly reduces, and has good economic benefit and prospects for commercial application.
Accompanying drawing explanation
Accompanying drawing is process flow diagram of the present invention.
In figure: 1 dissolves tower; 2 removal of impurities reaction towers; 3 pre-hydrotreating reaction towers; 4 knockout drums;
5 water wash columns; 6 bleaching towers; 7 desolventizing towers; 8 volatilization towers.
Embodiment
Below in conjunction with accompanying drawing and technical scheme, further illustrate the specific embodiment of the present invention.
Embodiment 1: with zinc nitrate and nickelous nitrate for precursor, mesopore SiO 2for carrier, coprecipitation method is adopted to prepare the NiO/ZnO-SiO of different Ni loading 2, the loading of ZnO is 15%, NiO/ZnO-SiO 2at 350 DEG C of reductase 12 h, prepare Ni/ZnO catalyzer.See the following form 1 feedstock property and different Ni loading hydrogenation adsorption desulfurize effect, and reaction conditions is feeding temperature 240 DEG C, hydrogen partial pressure 4MPa, volume space velocity 1h -1, hydrogen to oil volume ratio 200:1, resin concentration is 20%.See the following form resin properties after 1 resin raw material and hydrogenation adsorption desulfurize.
Colour measurement is toluene solution and the standard Fe-Co color solution colorimetric that resin is made into 50wt%.
As shown in Table 1, with Ni/ZnO-SiO 2for hydrogenation adsorption desulfurize catalyst, sweetening effectiveness and olefin saturated successful, remove most sulphur and alkene in resin.After desulfurization, resin form and aspect are substantially constant, and softening temperature slightly reduces, and bromine valency declines, and proves Ni/ZnO-SiO 2have good hydrogenation effect, Ni loading is increased to 40% from 20%, and sweetening effectiveness increases little, and therefore we select the loading of Ni to be 20%.
Embodiment 2: with 20%Ni loading Ni/ZnO-SiO 2for hydrogenation adsorption desulfurize catalyst, investigate the impact of reaction conditions on sweetening effectiveness and olefin saturated effect.See the following form resin properties after 2 pre-hydrogenation.
Embodiment 3: with 20%Ni loading Ni/ZnO for hydrogenation adsorption desulfurize catalyst, reaction conditions is feeding temperature 40 DEG C, hydrogen partial pressure 4MPa, volume space velocity 1h -1, hydrogen to oil volume ratio 200:1, resin concentration is 20%.The product property that following table 3 obtains after seeing operation in 500 hours.
The experimental result of 500 hours as shown in Table 3, at Ni/ZnO-SiO 2on reactive adsorption desulfurization catalyst in sulphur and bromine valency with start compared with test substantially constant, show that this technology has satisfactory stability.Run by the upper time, Catalyst Adsorption sulfur capacity reaches 20% of catalyst weight.
Embodiment 4: take eggshell type Pd catalyst as decolouring catalyzer; Carrier is Al 2o 3, Pd content 1%.At 15MPa and 260 DEG C, air speed 0.6h on the basis of embodiment 3 -1carry out hydrogenation decolorization experiment.The hydrogenated resin product property that following table 4 is shown in reaction process condition and finally obtains.
Thermostability: resin sample thermal treatment 5 hours at 180 DEG C, surveys its Fe-Co form and aspect.
As shown in Table 4, eggshell type Pd catalyst is that hydrogenation decolouring catalyzer shows good hydrogenation decolorizing effect, product Heat stability is good.
Embodiment 5: take eggshell type Pd catalyst as decolouring catalyzer; Relatively different carriers is on the impact of hydrogenation decolorizing effect.Reaction conditions is 15MPa and 260 DEG C, air speed 0.6h -1, hydrogen-oil ratio 400.The hydrogenated resin product property that following table 5 is shown in reaction process condition and finally obtains.
As shown in Table 5, eggshell type Pd catalyst is hydrogenation decolouring catalyzer, and carrier is not obvious on the impact of hydrogenation decolorizing effect.Load SiO 2type Pd catalyzer shows best hydrogenation effect, and gained hydrogenated resin stability is the highest.Embodiment 6: with PtPd loaded catalyst for hydrogenation decolours catalyzer, Al 2o 3for carrier, investigate reaction conditions to the impact of sweetening effectiveness.See the following form the rear hydrogenated resin character of 6 hydrogenation decolouring.
As shown in Table 6 with Ni/ZnO-SiO 2for reactive adsorption desulfurization catalyst, eggshell type Pd catalyst is hydrogenation decolouring catalyzer, adopts two sections of fixed bed hydrogenation modes to carry out hydrogenation reaction to resin, obtained drogenated DCPD resin, resin form and aspect are improved to water-white, and softening temperature slightly reduces and has good thermostability.Reaction conditions has certain influence to obtained hydrogenated resin character.
Embodiment 7: be that hydrogenation decolours catalyzer with eggshell type Pd catalyst, SiO 2for carrier.On the basis of embodiment 3 and embodiment 5, reaction conditions is: feeding temperature 260 DEG C, hydrogen partial pressure 15MPa, volume space velocity 0.6h -1, hydrogen to oil volume ratio 400:1, resin concentration is 20%.Following table 7 is shown in the rear hydrogenated resin character of 500 hydrogenation decolouring.
The experimental result of this process operation 500h as shown in Table 7, with Ni/ZnO-SiO 2for reactive adsorption desulfurization catalyst, eggshell type Pd catalyst is hydrogenation decolouring catalyzer, adopts two sections of fixed bed hydrogenation modes to carry out hydrogenation reaction to resin, and obtained hydrogenated resin, resin form and aspect are improved to water-white, and softening temperature slightly reduces and has good thermostability.The above results shows that technology of the present invention has satisfactory stability, catalyzer long service life.

Claims (8)

1. prepare a method for drogenated DCPD resin, it is characterized in that, dissolved in dissolving tower by DCPD resin with solvent, wherein, the mass percent of DCPD resin is 15%-40%; Enter again and be equipped with in the removal of impurities reactor of sorbent material, removing colloid; Then mix the pre-hydrotreating reaction tower injecting and hydrogenation adsorption desulfurize catalyst is housed with hydrogen, hydrogenation adsorption desulfurize catalyst removes sulphur, chlorine/fluorine and diene in DCPD resin, temperature of reaction 200-260 DEG C, hydrogen partial pressure 2-8MPa, volume space velocity 1-4h -1, hydrogen and DCPD resin solution volume ratio 100-300:1, obtain the DCPD resin solution after pre-hydrogenation; DCPD resin solution after pre-hydrogenation enters knockout drum, hydrogen enters water wash column, and the hydrogen after washing enters pre-hydrotreating reaction tower again, and liquid directly enters bleaching tower, carry out hydrogenation decolouring, temperature of reaction 240-320 DEG C, hydrogen partial pressure 8-18MPa, volume space velocity 0.4-1.6h -1, hydrogen and DCPD resin solution volume ratio 200-600:1; The hydrogenation catalyzer used that decolours is eggshell type Pd catalyst; Resin solution after hydrogenation decolouring injects desolventizing tower, and through air distillation, the product solvent cycle that tower top distills out dissolves petroleum resin again, and bottom product enters volatilization tower; Volatilization tower negative-pressure operation, volatilization tower tower top goes out the high boiling point organic compound that the resin cracking of hydrogenation decolorization PetroChina Company Limited. produces, and go out hydrogenation resin at the bottom of volatilization tower tower, resin form and aspect are improved to water white.
2. method according to claim 1, is characterized in that, described solvent is one or more mixing in hexanaphthene, normal heptane, n-decane, methylcyclohexane, dimethyl cyclohexane, trimethyl-cyclohexane, perhydronaphthalene.
3. method according to claim 1 and 2, is characterized in that, described sorbent material is the Al of central hole structure 2o 3, mesopore volume accounts for more than 80% of total pore volume, and its pore size distribution is at 30-50nm.
4. method according to claim 1 and 2, is characterized in that, described hydrogenation adsorption desulfurize catalyst is Ni/ZnO-SiO 2catalyzer, wherein Ni content is Ni/ZnO-SiO 220% ~ 40% of catalyst quality, ZnO content is Ni/ZnO-SiO 215% ~ 25%, SiO of catalyst quality 2content is Ni/ZnO-SiO 235% ~ 65% of catalyst quality.
5. method according to claim 3, is characterized in that, described hydrogenation adsorption desulfurize catalyst is Ni/ZnO-SiO 2catalyzer, wherein Ni content is Ni/ZnO-SiO 220% ~ 40% of catalyst quality, ZnO content is Ni/ZnO-SiO 215% ~ 25%, SiO of catalyst quality 2content is Ni/ZnO-SiO 235% ~ 65% of catalyst quality.
6. the method according to claim 1,2 or 5, is characterized in that, the carrier of described eggshell type Pd catalyst is SiO 2, Al 2o 3, Al 2o 3-TiO 2or SiO 2-Al 2o 3, Pd content is 0.3% ~ 1.0% of eggshell type Pd catalyst quality.
7. method according to claim 3, is characterized in that, the carrier of described eggshell type Pd catalyst is SiO 2, Al 2o 3, Al 2o 3-TiO 2or SiO 2-Al 2o 3, Pd content is 0.3% ~ 1.0% of eggshell type Pd catalyst quality.
8. method according to claim 4, is characterized in that, the carrier of described eggshell type Pd catalyst is SiO 2, Al 2o 3, Al 2o 3-TiO 2or SiO 2-Al 2o 3, Pd content is 0.3% ~ 1.0% of eggshell type Pd catalyst quality.
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CN113880969A (en) * 2021-11-08 2022-01-04 大连理工大学 Method for preparing hydrogenated petroleum resin by hydrogenation of cold-polymerized petroleum resin
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Publication number Priority date Publication date Assignee Title
CN111097412A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Liquid phase hydrogenation method of poly DCPD petroleum resin based on modified palladium supported catalyst
CN111097418A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Liquid-phase hydrofining method of poly DCPD petroleum resin based on modified nickel-based supported catalyst
CN111574645A (en) * 2020-05-27 2020-08-25 大连理工大学 Hydrogenation method for high-sulfur petroleum resin
CN111574645B (en) * 2020-05-27 2021-04-20 大连理工大学 Hydrogenation method for high-sulfur petroleum resin
WO2022036838A1 (en) * 2020-08-18 2022-02-24 南京延长反应技术研究院有限公司 Micro-interface reaction system and method for hydrogenation of petroleum resin
WO2022036837A1 (en) * 2020-08-18 2022-02-24 南京延长反应技术研究院有限公司 Reaction system and method for hydrogenation of petroleum resin
CN113880969A (en) * 2021-11-08 2022-01-04 大连理工大学 Method for preparing hydrogenated petroleum resin by hydrogenation of cold-polymerized petroleum resin

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