CN103724544B - The preparation method of hydrogenation dcpd resin - Google Patents
The preparation method of hydrogenation dcpd resin Download PDFInfo
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- CN103724544B CN103724544B CN201310724186.0A CN201310724186A CN103724544B CN 103724544 B CN103724544 B CN 103724544B CN 201310724186 A CN201310724186 A CN 201310724186A CN 103724544 B CN103724544 B CN 103724544B
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Abstract
Hydrogenation dcpd resin disclosed by the invention belongs to resin technology field, in order to improve the quality product of dicyclopentadiene petroleum resin, production efficiency and minimizing " three wastes " discharge, labour intensity, propose a kind of thermal polymerization method and produce dicyclopentadiene petroleum resin liquid, and adopt directly resin liquid is fixed continuously a two-stage hydrogenation explained hereafter white, the two good hydrogenation dicyclopentadiene petroleum resin of resistance to light thermal property.Polymerization does not use catalyzer, can improve rosin products quality on the one hand, can reduce " three wastes " discharge on the other hand.Directly the crude resin liquid after polymerization is carried out continuous fixed bed secondary hydrogenation substantially increase production efficiency and reduce labour intensity.
Description
Technical field
The present invention relates to a kind of preparation method of petroleum resin, more particularly, the present invention relates to a kind of take C5 fraction as the preparation method that the dcpd resin of hydrogenation prepared by raw material.
Background technology
In ethylene cracker, the amount of by product C 5 fraction is about 15% ~ 20% of ethylene yield, and the summation of the cyclopentadiene that C 5 fraction contains (CPD) and dicyclopentadiene (DCPD) has 20% ~ 30%.C 5 fraction separating technology has become ripe, but how the DCPD after being separated utilizes, and has become a new problem.The ethylene unit of a set of 300,000 tons, the potential resources of its DCPD is 7 ~ 9kt/a, and at present, China has stepped into the large ethene epoch, domestic building, newly-built ethylene project scale is all 800,000 tons of \ years or more.Along with being constructed and put into operation of a collection of large ethylene projects such as Daqing petrochemical, Fushun petrochemical industry, wuhan petrochemical industry and Huizhou ethene second phase, expect 2015, China's ethene aggregated capacity will reach 2500 ~ 27,000,000 tons every year.At present, there is part producer to utilize DCPD to produce diamantane, agrochemical product although domestic, but so many DCPD can not be consumed, therefore, utilizing DCPD to produce petroleum resin is a kind of approach utilizing DCPD in a large number, but DCPD petroleum resin are due to the nonsaturation of dicyclopentadiene, all can react with other compounds when being polymerized and after polymerization, forming reactions petroleum resin, oxidative stability is bad, and color is yellow, second-rate, purposes is narrow, and price is low, so must improve its quality by hydrogenation to expand purposes.
At present, industrial employing with 95% dicyclopentadiene be raw material, with BF
3-phenol complexes is Catalyst Production dicyclo resin, catalyst levels is 0.72%, the benzene adding raw material half makes solvent, polyase 13 hour at 30 DEG C, after reaction mass Removal of catalyst, again 230 DEG C, underpressure distillation under 2.6kpa condition, except desolventizing and unreacted part, at the bottom of still, obtain dicyclopentadiene petroleum resin.Certain company domestic produces DCPD resin in built annual 2500 tons of C5 Resin Industry exemplary device, have employed thermal polymerization method technique, but quality product is poor, color is darker when producing DCPD resin.Although catalysis method reaction conditions is gentleer, removing of catalyzer is very crucial, removes only, will have a strong impact on quality and the application of resin.Catalyst removal mainly contains alcohol wash method, WATER-WASHING METHOD, liquefied ammonia neutralisation, and the common drawback of this several method is that " three wastes " are seriously polluted, and labour intensity is large, and unstable product quality, product yield is low.
Non-hydrogenation dicyclo petroleum resin, wherein all contain a large amount of unsaturated double-bonds, and have the reactivity of height, oxidative stability is bad.By hydrogenation, the double bond in resin can be made saturated, remove the halogen element that resin remains in the course of the polymerization process, improve quality product, that obtain white, that resistance to light thermal property is good hydrogenated resin, can be used as hot-melt adhesive or pressure sensitive adhesives, thus expands range of application.At present, domestic industry does not also have producer carry out hydrogenation to DCPD resin.
That the dicyclopentadiene in C5 raw material is removed in Chinese patent CN200710179778.3, then the C 5 fraction after decylization being separated take metal halide as catalyzer to diolefin wherein carry out low temperature cationic poly-after, adopt monoolefine to add polymerization system as polymeric modifier simultaneously; The resin obtained after polymerization produces C5 hydrogenated resin through hydrogenation unit again.Though this technique has carried out hydrogenation but separation process is complicated, and the cyclopentadiene in C5 raw material is not fully used.
In sum, prior art does not also solve the various problems of dcpd resin.
Summary of the invention
In order to improve the quality product of dicyclopentadiene petroleum resin, production efficiency and minimizing " three wastes " discharge, labour intensity, contriver is through repetition test and further investigation, develop a kind of thermal polymerization method and produce dicyclopentadiene petroleum resin liquid, and resin liquid is directly fixed a two-stage hydrogenation explained hereafter hydrogenation dicyclopentadiene petroleum resin by employing continuously.
Concrete technical scheme is as follows:
Hot polymerization of the present invention and hydrogenation method prepare the method for hydrogenation dicyclopentadiene petroleum resin mainly by dicyclopentadiene and a certain proportion of solvent, under certain temperature, pressure and the condition of time, application radical polymerization principle, reaction generates dicyclopentadiene petroleum resin liquid; Then dcpd resin liquid is directly sent into fixed bed and carry out hydrogenation; The high-quality hydrogenation dicyclopentadiene petroleum resin of white is obtained again by stripping tower stripping.Concrete grammar comprises the following steps:
(1) preparation of raw material: by mass content be 85% ~ 95% dicyclopentadiene and solvent mix by weight 1: 1.5 ~ 2.0;
(2) polyreaction: preheater preheats to 180 ~ 220 DEG C sent into by raw material step (1) prepared, then send into polymerization reactor, 8 ~ 12 hours thermopolymerization time under temperature of reaction 250 ~ 260 DEG C and pressure 2.1Mpa, obtains crude resin liquid;
(3) one-stage hydrogenation: crude resin liquid is heated through process furnace, is then mixed into the section low-voltage hydrogenation reactor that one section of catalyzer is housed by crude resin liquid and hydrogen, at reaction pressure 2.0 ~ 3.5Mpa, temperature 260 ~ 300 DEG C, air speed 0.2 ~ 2.0h
-1carry out one-stage hydrogenation with under the condition of hydrogen to oil volume ratio 100 ~ 400: 1, described one section of catalyzer is the catalyzer of alumina load tungsten nickel;
(4) secondary hydrogenation: the material after one-stage hydrogenation is after cooling and isolate gas, two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed are mixed into, at reaction pressure 3.5 ~ 40Mpa, temperature 260 ~ 300 DEG C, air speed 0.2 ~ 2.0h again through heating and hydrogen
-1carry out secondary hydrogenation with under the condition of hydrogen to oil volume ratio 100 ~ 400: 1, described two sections of catalyzer are the catalyzer of the carrier loaded amorphous alloy nickel NiB of sepiolite;
(5) stripping: send after the material cooling after secondary hydrogenation also divided gas flow into stripping tower, stripping bottom temperature controls at 240 ~ 260 DEG C, and solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin out delivers to tablets press, granulation through cooling, packaging.
In step (1), selecting of described solvent can be determined specification of quality such as product softening temperatures or adjust according to client with ratio, and preferably, the solvent described in step (1) is hexanaphthene, normal hexane or pyrolysis C 5.
One section of described catalyzer has 150 ~ 350m
2the specific surface area of/g and the pore volume of 0.35 ~ 0.8ml/g.Dipping method can be adopted to prepare.The aluminum oxide that alumina supporter can use Beijing Chemical Research Institute to produce, the trade mark is BCA-31.With the quality of catalyzer and mass percent, one section of catalyzer contains the tungsten of 3 ~ 5% and the nickel of 10 ~ 25%.The water-soluble salt of tungsten and nickel is dissolved in water respectively or simultaneously, adopts step impregnation or total immersion method by tungsten and Ni on the alumina support, then dry Sum decomposition, then through reduction, obtain operable one section of catalyzer.
Two sections of described catalyzer are the catalyzer of the carrier loaded amorphous alloy nickel NiB of sepiolite, and preparation method can adopt dipping method, and with the quality of catalyzer and mass percent, nickel content is 10 ~ 25%.Such as, the catalyzer XL002 of two sections of catalyzer use Lanzhou Xin Lan chemical companies production.
After the stripping of step (5), the solvent that stripping tower top is extracted out is refined through distillation tower, and the solvent after refining can loop back step (1) and use.
Dicyclopentadiene petroleum resin liquid contains a large amount of unsaturated double-bonds, and have the reactivity of height, oxidation stability is bad.By preparation method's hydrogenation of the present invention, make the double bond in resin liquid saturated, remove resin sulphur halogen impurity residual in polymerization process, obtain white, the two good hydrogenated resin of resistance to light thermal property.
Polymerization process of the present invention uses thermal polymerization method, does not use catalyzer, can improve rosin products quality on the one hand, can reduce " three wastes " discharge on the other hand.
Preparation method of the present invention adopts and directly the crude resin liquid after polymerization is carried out continuous fixed bed secondary hydrogenation production hydrogenated resin, and superiority is obvious, substantially increases production efficiency and reduces labour intensity.Relative to hydrogenation in autoclave, autoclave hydrogenation exists that hydrogenation time is long, efficiency is low, catalyzer needs filtered and recycled, and exists and remove unclean phenomenon, is unfavorable for that industrialness is produced.Common resin finished product repeated hydrogenation method adopts first synthetic resins, after then solid resin being put into a certain proportion of dissolution with solvents, adds catalyzer and carry out hydrogenation, this process energy consumption is high, long flow path, uneconomical.Relative to this usual method, the preparation method that the feature that the present invention is directed to dcpd resin proposes has the advantage of economical and efficient.
Embodiment
Explain further below in conjunction with embodiment and method of the present invention is described.
(1) preparation of raw material: by mass content be 85% ~ 95% dicyclopentadiene and solvent mix through static mixer by weight 1: 1.5 ~ 2.0;
(2) polyreaction: preheater preheats to 180 ~ 220 DEG C sent into by raw material step (1) prepared, send into polymerization reactor again, with the residual air in nitrogen replacement reactor, then reaction mass heated and start stirring, 8 ~ 12 hours thermopolymerization time under temperature of reaction 250 ~ 260 DEG C and pressure 2.1Mpa, obtain crude resin liquid, send into thick product storage tank stand-by;
(3) one-stage hydrogenation: crude resin liquid is heated through process furnace, is then mixed into one section of low-voltage hydrogenation reactor that one section of catalyzer is housed by crude resin liquid and hydrogen, at reaction pressure 2.0 ~ 3.5Mpa, temperature 260 ~ 300 DEG C, air speed 0.2 ~ 2.0h
-1, hydrogen to oil volume ratio 100 ~ 400: 1 condition under carry out one-stage hydrogenation, described one section of catalyzer is the catalyzer of alumina load tungsten nickel; After hydrogenation, material is through refrigerated separation gas, separator pressure 0.18MPa, temperature 45 C, and separate hydrogen and light hydrocarbon gas, liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation is after cooling is opened and isolated gas, two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed are mixed into, at reaction pressure 2.0 ~ 40Mpa, temperature 260 ~ 300 DEG C, air speed 0.2 ~ 2.0h again through heating and hydrogen
-1carry out secondary hydrogenation with under the condition of hydrogen to oil volume ratio 100 ~ 400: 1, described two sections of catalyzer are the catalyzer of the carrier loaded amorphous alloy nickel NiB of sepiolite; After hydrogenation, material enters basin through refrigerated separation;
(5) stripping: send after the feed separation gas after secondary hydrogenation into stripping tower, stripping bottom temperature controls at 240 ~ 260 DEG C, and solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin out delivers to tablets press, granulation through cooling, packaging.
Embodiment 1
(1) preparation of raw material: be that the dicyclopentadiene of 85% ~ 95% and the cracked C 5 fraction of Lanzhou Petrochemical Company production mix by weight 1: 1.8 through static mixer by the mass content that Lanzhou Xin Lan chemical company produces;
(2) polyreaction: preheater preheats to 200 DEG C sent into by raw material step (1) prepared, send into polymerization reactor again, with the residual air in nitrogen replacement reactor, then reaction mass heated and start stirring, the 10 hours thermopolymerization time under temperature of reaction 250 ~ 260 DEG C, pressure 2.1Mpa, obtain crude resin liquid, send into thick product storage tank stand-by;
(3) one-stage hydrogenation: be heated to 240 DEG C through process furnace by defeated for crude resin liquid, then crude resin liquid and hydrogen are mixed into one section of low-voltage hydrogenation reactor that one section of catalyzer is housed, at reaction pressure 3.0Mpa, temperature 270 DEG C, air speed 1.0h
-1, hydrogen to oil volume ratio 200: 1 condition under carry out one-stage hydrogenation, described one section of catalyzer is the catalyzer of alumina load tungsten nickel, alumina supporter use Beijing Chemical Research Institute produce aluminum oxide, the trade mark is BCA-31.With the quality of catalyzer and mass percent, one section of catalyzer contains the tungsten of 5% and the nickel of 25%, has 300m
2the specific surface area of/g and the pore volume of 0.7ml/g; After hydrogenation, material is through refrigerated separation gas, separator pressure 0.18MPa, temperature 45 C, and separate hydrogen and light hydrocarbon gas, liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation after cooling and isolating gas, then through being heated to 240 DEG C, is mixed into hydrogen two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed, at reaction pressure 30Mpa, temperature 270 DEG C, air speed 1.0h
-1, hydrogen to oil volume ratio 200: 1 condition under carry out secondary hydrogenation, described two sections of catalyzer are the catalyzer of the carrier loaded amorphous alloy nickel NiB of sepiolite, and nickel content is 15%; After hydrogenation, material enters basin through refrigerated separation;
(5) stripping: send after the feed separation gas after secondary hydrogenation into stripping tower, stripping bottom temperature controls at 250 DEG C, and solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin out delivers to granulator granulation packaging through cooling.
Embodiment 2
(1) preparation of raw material: by the mass content that Lanzhou Xin Lan chemical company produces be 85% ~ 95% dicyclopentadiene and hexanaphthene mix by weight 1: 1.5;
(2) polyreaction: preheater preheats to 210 DEG C sent into by raw material step (1) prepared, then sends into polymerization reactor, the 12 hours thermopolymerization time under temperature of reaction 250 ~ 260 DEG C and pressure 2.1Mpa, obtains crude resin liquid;
(3) one-stage hydrogenation: crude resin liquid is heated through process furnace, is then mixed into one section of low-voltage hydrogenation reactor that one section of catalyzer is housed by crude resin liquid and hydrogen, at reaction pressure 2.2Mpa, temperature 300 DEG C, air speed 1.5h
-1carry out one-stage hydrogenation with under the condition of hydrogen to oil volume ratio 300: 1, described one section of catalyzer is the catalyzer of alumina load tungsten nickel; With the quality of catalyzer and mass percent, one section of catalyzer contains the tungsten of 3% and the nickel of 15%, has 180m
2the specific surface area of/g and the pore volume of 0.4ml/g; After hydrogenation, material is through refrigerated separation gas, separator pressure 0.18MPa, temperature 45 C, and separate hydrogen and light hydrocarbon gas, liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation after cooling and isolate gas, then is mixed into two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed, at reaction pressure 10Mpa, temperature 290 DEG C, air speed 1.4h through heating and hydrogen
-1carry out secondary hydrogenation with under the condition of hydrogen to oil volume ratio 300: 1, described two sections of catalyzer are the catalyzer XL002 of the carrier loaded amorphous alloy nickel NiB of sepiolite that Lanzhou Xin Lan chemical company produces;
(5) stripping: send after the material cooling after secondary hydrogenation also divided gas flow into stripping tower, stripping bottom temperature controls at 255 DEG C, and solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin out delivers to tablets press, granulation through cooling, packaging.
Embodiment 3
(1) preparation of raw material: by mass content be 85% ~ 95% dicyclopentadiene and pentamethylene mix by weight 1: 2.0;
(2) polyreaction: preheater preheats to 210 DEG C sent into by raw material step (1) prepared, then sends into polymerization reactor, the 9 hours thermopolymerization time under temperature of reaction 250 ~ 260 DEG C and pressure 2.1Mpa, obtains crude resin liquid;
(3) one-stage hydrogenation: crude resin liquid is heated through process furnace, is then mixed into one section of low-voltage hydrogenation reactor that one section of catalyzer is housed by crude resin liquid and hydrogen, at reaction pressure 2.8Mpa, temperature 260 DEG C, air speed 0.5h
-1carry out one-stage hydrogenation with under the condition of hydrogen to oil volume ratio 150: 1, described one section of catalyzer is the catalyzer of alumina load tungsten nickel, the aluminum oxide that alumina supporter uses Beijing Chemical Research Institute to produce, and the trade mark is BCA-31.With the quality of catalyzer and mass percent, one section of catalyzer contains the tungsten of 5% and the nickel of 25%, has 300m
2the specific surface area of/g and the pore volume of 0.7ml/g; After hydrogenation, material is through refrigerated separation gas, separator pressure 0.18MPa, temperature 45 C, and separate hydrogen and light hydrocarbon gas, liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation after cooling and isolate gas, then is mixed into two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed, at reaction pressure 25Mpa, temperature 275 DEG C, air speed 0.5h through heating and hydrogen
-1carry out secondary hydrogenation with under the condition of hydrogen to oil volume ratio 150: 1, described two sections of catalyzer are the catalyzer XL002 of the carrier loaded amorphous alloy nickel NiB of sepiolite that Lanzhou Xin Lan chemical company produces;
(5) stripping: send after the material cooling after secondary hydrogenation also divided gas flow into stripping tower, stripping bottom temperature controls at 260 DEG C, and solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin out delivers to tablets press, granulation through cooling, packaging.
Compared with the dcpd resin of non-hydrogenation, the double bond content of the hydrogenation dcpd resin that embodiment 1-3 produces is low, and bromine number is low, and whiteness is high, and resistance to light thermal property is high, good stability during long-term placement, nondiscoloration.
Claims (6)
1. hot polymerization and hydrogenation method prepare a method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that said method comprising the steps of:
(1) preparation of raw material: by mass content be 85% ~ 95% dicyclopentadiene and solvent mix by weight 1: 1.5 ~ 2.0;
(2) polyreaction: preheater preheats to 180 ~ 220 DEG C sent into by raw material step (1) prepared, then send into polymerization reactor, 8 ~ 12 hours thermopolymerization time under temperature of reaction 250 ~ 260 DEG C and pressure 2.1Mpa, obtains crude resin liquid;
(3) one-stage hydrogenation: crude resin liquid is heated through process furnace, is then mixed into one section of low-voltage hydrogenation reactor that one section of catalyzer is housed by crude resin liquid and hydrogen, at reaction pressure 2.0 ~ 3.5Mpa, temperature 260 ~ 300 DEG C, air speed 0.2 ~ 2.0h
-1carry out one-stage hydrogenation with under the condition of hydrogen to oil volume ratio 100 ~ 400: 1, described one section of catalyzer is the catalyzer of alumina load tungsten and nickel;
(4) secondary hydrogenation: the material after one-stage hydrogenation is after cooling and isolate gas, two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed are mixed into, at reaction pressure 3.5 ~ 40Mpa, temperature 260 ~ 300 DEG C, air speed 0.2 ~ 2.0h again through heating and hydrogen
-1carry out secondary hydrogenation with under the condition of hydrogen to oil volume ratio 100 ~ 400: 1, described two sections of catalyzer are the catalyzer of the carrier loaded amorphous alloy nickel NiB of sepiolite;
(5) stripping: send after the material cooling after secondary hydrogenation also divided gas flow into stripping tower, stripping bottom temperature controls at 240 ~ 260 DEG C, and solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin out delivers to tablets press, granulation through cooling, packaging.
2. hot polymerization as claimed in claim 1 and hydrogenation method prepare the method for hydrogenation dicyclopentadiene petroleum resin, and it is characterized in that, in step (1), described solvent is hexanaphthene, normal hexane or cracked C 5 fraction.
3. hot polymerization as claimed in claim 1 and hydrogenation method prepare the method for hydrogenation dicyclopentadiene petroleum resin, and it is characterized in that, one section of described catalyzer has 150 ~ 350m
2the specific surface area of/g and the pore volume of 0.35 ~ 0.8ml/g.
4. hot polymerization as claimed in claim 1 and hydrogenation method prepare the method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that, the alumina supporter of one section of described catalyzer uses the aluminum oxide of Beijing Chemical Research Institute's production, the trade mark is BCA-31, with the quality of catalyzer and mass percent, one section of catalyzer contains the tungsten of 3 ~ 5% and the nickel of 10 ~ 25%.
5. hot polymerization as claimed in claim 1 and hydrogenation method prepare the method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that, two sections of described catalyzer are the catalyzer of the carrier loaded amorphous alloy nickel NiB of sepiolite, and with the quality of catalyzer and mass percent, nickel content is 10 ~ 25%.
6. hot polymerization as claimed in claim 1 and hydrogenation method prepare the method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that, after the stripping of step (5), the solvent that stripping tower top is extracted out is refined through distillation tower, and the solvent cycle after refining is returned step (1) and used.
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105585666B (en) * | 2014-10-22 | 2019-01-04 | 中国石油化工股份有限公司 | A kind of preparation method of dicyclopentadiene hydrogenated petroleum resin |
| CN105367714B (en) * | 2015-12-03 | 2018-04-27 | 大连理工大学 | A kind of method for preparing drogenated DCPD resin |
| CN105601815B (en) * | 2015-12-31 | 2017-12-29 | 庆阳永欣石油化工有限公司 | A kind of manufacturing technique and its hydrogenation reaction kettle for hydrogenating dicyclopentadiene petroleum resin |
| CN105646786A (en) * | 2016-02-29 | 2016-06-08 | 山东玉皇化工有限公司 | Method for preparing dicyclopentadiene hydrogenated petroleum resin from dicyclopentadiene directly |
| CN106008820B (en) * | 2016-07-27 | 2018-02-16 | 朗盈科技（北京）有限公司 | Low colourity light dydrocarbon carbon nine is copolymerized the production system and method for hydrogenation resin |
| KR102327050B1 (en) | 2017-12-29 | 2021-11-15 | 한화솔루션 주식회사 | Method for selective hydrogenation |
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