CN103724544A - Preparation method of hydrogenated dicyclopentadiene resin - Google Patents
Preparation method of hydrogenated dicyclopentadiene resin Download PDFInfo
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Abstract
The invention discloses a hydrogenated dicyclopentadiene resin, belonging to the technical field of resins. In order to enhance the product quality and production efficiency of the dicyclopentadiene petroleum resin and reduce the three-waste emission and labor intensity, the invention provides a white high-light/heat-resistance hydrogenated dicyclopentadiene petroleum resin which is prepared by the following steps: producing a dicyclopentadiene petroleum resin liquid by a hot polymerization process, and directly continuously carrying out a fixed bed two-section hydrogenation technique on the resin liquid. No catalyst is used in the polymerization process, thereby enhancing the quality of the resin product and reducing the three-waste emission. The polymerized crude resin liquid is directly continuously subjected to fixed bed two-section hydrogenation, thereby greatly enhancing the production efficiency and lowering the labor 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 preparation method who prepares the dcpd resin of hydrogenation take C5 fraction as 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%.It is ripe that C 5 fraction separating technology has become, but how DCPD after separating to utilize, and become a new problem.The ethylene unit of a set of 300,000 tons, the potential resources of its DCPD is 7～9kt/a, at present, China has stepped into the large ethene epoch, domestic building, newly-built ethylene project scale all 800,000 tons year or more than.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, although domestic, there is part producer to utilize DCPD to produce diamantane, agrochemical product, but can not consume so many DCPD, therefore, utilizing DCPD to produce petroleum resin is a kind of approach that utilize in a large number DCPD, but DCPD petroleum resin are due to the nonsaturation of dicyclopentadiene, when polymerization and after polymerization, all can react with other compounds, form reactive petroleum resin, oxidative stability is bad, color Huang, second-rate, purposes is narrow, and price is low, so must improve its quality by hydrogenation, expands purposes.
At present, the dicyclopentadiene of industrial employing take 95% is as raw material, with BF
3-phenol complexes is Catalyst Production dicyclo resin, catalyst levels is 0.72%, add the benzene of raw material half to make solvent, polyase 13 hour at 30 ℃, after reaction mass Removal of catalyst, underpressure distillation under 230 ℃, 2.6kpa condition again, except desolventizing and unreacted part, obtains dicyclopentadiene petroleum resin at the bottom of still.Domestic certain company has produced DCPD resin in built annual 2500 tons of C5 Resin Industry exemplary device, adopted 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 shortcoming of this several method is that " three wastes " are seriously polluted, and labour intensity is large, unstable product quality, and product yield is low.
Non-hydrogenation dicyclo petroleum resin, wherein all contain a large amount of unsaturated double-bonds, have the reactivity of height, and oxidative stability is bad.By hydrogenation, can make the two keys in resin saturated, remove resin residual halogen element in polymerization process, improved quality product, obtain white, the good hydrogenated resin of fast light thermal characteristics, can be used as hot-melt adhesive or pressure sensitive adhesives, thereby expanded range of application.At present, in domestic industry, also do not have producer to carry out hydrogenation to DCPD resin.
In Chinese patent CN200710179778.3, be that the dicyclopentadiene in C5 raw material is removed, then the C 5 fraction after decylization being separated take metal halide as catalyzer to diolefin wherein carry out low temperature positively charged ion poly-after, adopt monoolefine to add polymerization system as polymeric modifier simultaneously; The resin obtaining after polymerization is produced C5 hydrogenated resin through hydrogenation unit again.The separation process complexity though this technique has been carried out hydrogenation, and cyclopentadiene in C5 raw material is not fully used.
In sum, prior art does not also solve the variety of issue of dcpd resin.
Summary of the invention
In order to improve quality product, production efficiency and minimizing " three wastes " discharge, the labour intensity of dicyclopentadiene petroleum resin, contriver is through repetition test and further investigation, developed a kind of thermal polymerization method and produced dicyclopentadiene petroleum resin liquid, and employing is directly fixed resin liquid a two-stage hydrogenation explained hereafter hydrogenation dicyclopentadiene petroleum resin continuously.
Concrete technical scheme is as follows:
The method that hot polymerization of the present invention and hydrogenation method are prepared hydrogenation dicyclopentadiene petroleum resin is mainly by dicyclopentadiene and a certain proportion of solvent, under the condition of certain temperature, pressure and 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; By stripping tower stripping, obtain white high-quality hydrogenation dicyclopentadiene petroleum resin again.Concrete grammar comprises the following steps:
(1) preparation of raw material: the dicyclopentadiene that is 85%～95% by mass content and solvent mix by weight 1: 1.5～2.0;
(2) polyreaction: the raw material of step (1) preparation is sent into preheater and be preheated to 180～220 ℃, then send into polymerization reactor, 8～12 hours thermopolymerization time under 250～260 ℃ of temperature of reaction and pressure 2.1Mpa, obtain crude resin liquid;
(3) one-stage hydrogenation: make crude resin liquid through process furnace heating, then crude resin liquid and hydrogen are mixed into the section low-voltage hydrogenation reactor that one section of catalyzer is housed, at reaction pressure 2.0～3.5Mpa, 260～300 ℃ of temperature, air speed 0.2～2.0h
-1with hydrogen to oil volume ratio 100～400: under 1 condition, carry out one-stage hydrogenation, described one section of catalyzer that catalyzer is alumina load tungsten nickel;
(4) secondary hydrogenation: the material after one-stage hydrogenation is through cooling and isolate after gas, through heating and hydrogen, be mixed into two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed again, at reaction pressure 3.5～40Mpa, 260～300 ℃ of temperature, air speed 0.2～2.0h
-1with hydrogen to oil volume ratio 100～400: under 1 condition, carry out secondary hydrogenation, described two sections of catalyzer that catalyzer is the carrier loaded amorphous alloy nickel NiB of sepiolite;
(5) stripping: will send into stripping tower after cooling the material after secondary hydrogenation and divided gas flow, stripping tower reactor temperature is controlled at 240～260 ℃, solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin is out through the cooling tablets press of delivering to, and granulation, packs.
In step (1), selecting with ratio of described solvent can determine or adjust specification of quality such as product softening temperatures according to client, 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.Can adopt dipping method preparation.The aluminum oxide that alumina supporter can be used Beijing Chemical Research Institute to produce, the trade mark is BCA-31.In quality and the mass percent of catalyzer, one section of catalyzer contains 3～5% tungsten and 10～25% nickel.The water-soluble salt of tungsten and nickel is dissolved in water respectively or simultaneously, adopt step impregnation or total immersion method by tungsten and Ni on alumina supporter, then dry and decompose, then through reduction, obtain operable one section of catalyzer.
Two sections of described catalyzer that catalyzer is the carrier loaded amorphous alloy nickel NiB of sepiolite, preparation method can adopt dipping method, and in quality and the mass percent of catalyzer, nickel content is 10～25%.For example, two sections of catalyzer XL002 that catalyzer is used Lanzhou Xin Lan chemical company to produce.
After the stripping of step (5), the solvent that extract out on stripping tower top is refining 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, has the reactivity of height, and oxidation stability is bad.By preparation method's hydrogenation of the present invention, make two keys in resin liquid saturated, remove resin residual sulphur halogen impurity in polymerization process, obtain white, the two good hydrogenated resins of fast light thermal characteristics.
Polymerization process of the present invention is used thermal polymerization method, does not use catalyzer, can improve rosin products quality on the one hand, can reduce on the other hand " three wastes " discharge.
Preparation method of the present invention adopts and directly the crude resin liquid after polymerization is carried out to continuous fixed bed secondary hydrogenation production hydrogenated resin, and superiority is obvious, has greatly improved production efficiency and has reduced labour intensity.With respect 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 produces.Common resin finished product repeated hydrogenation method is to adopt first synthetic resins, then solid resin is put into after a certain proportion of dissolution with solvents, is added catalyzer to carry out hydrogenation, and this process energy consumption is high, long flow path, uneconomical.With respect to this usual method, the preparation method who the present invention is directed to the feature proposition of dcpd resin has advantages of economical and efficient.
Embodiment
Below in conjunction with embodiment, further explain and illustrate method of the present invention.
(1) preparation of raw material: the dicyclopentadiene that is 85%～95% by mass content and solvent mix through static mixer by weight 1: 1.5～2.0;
(2) polyreaction: the raw material of step (1) preparation is sent into preheater and be preheated to 180～220 ℃, send into again polymerization reactor, with the residual air in nitrogen replacement reactor, then reaction mass heated and start stirring, 8～12 hours thermopolymerization time under 250～260 ℃ of temperature of reaction and pressure 2.1Mpa, obtain crude resin liquid, send into thick product storage tank stand-by;
(3) one-stage hydrogenation: make crude resin liquid through process furnace heating, 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 2.0～3.5Mpa, 260～300 ℃ of temperature, 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 that catalyzer is alumina load tungsten nickel; After hydrogenation, material is through refrigerated separation gas, and separator pressure 0.18MPa, temperature 45 C, separate hydrogen and light hydrocarbon gas, and liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation is isolated after gas through cooling opening, through heating and hydrogen, be mixed into two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed again, at reaction pressure 2.0～40Mpa, 260～300 ℃ of temperature, air speed 0.2～2.0h
-1with hydrogen to oil volume ratio 100～400: under 1 condition, carry out secondary hydrogenation, described two sections of catalyzer that catalyzer is the carrier loaded amorphous alloy nickel NiB of sepiolite; After hydrogenation, material enters basin through refrigerated separation;
(5) stripping: will send into stripping tower after the feed separation gas after secondary hydrogenation, stripping tower reactor temperature is controlled at 240～260 ℃, solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin is out through the cooling tablets press of delivering to, and granulation, packs.
Embodiment 1
(1) preparation of raw material: the cracked C 5 fraction that the dicyclopentadiene that the mass content that Lanzhou Xin Lan chemical company is produced is 85%～95% and Lanzhou Petrochemical Company are produced is by weight through static mixer mixing at 1: 1.8;
(2) polyreaction: the raw material of step (1) preparation is sent into preheater and be preheated to 200 ℃, send into again polymerization reactor, with the residual air in nitrogen replacement reactor, then reaction mass heated and start stirring, the 10 hours thermopolymerization time under 250～260 ℃ of temperature of reaction, pressure 2.1Mpa, obtain crude resin liquid, send into thick product storage tank stand-by;
(3) one-stage hydrogenation: be heated to 240 ℃ by defeated crude resin liquid through process furnace, 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, 270 ℃ of temperature, air speed 1.0h
-1, carry out one-stage hydrogenation under the hydrogen to oil volume ratio condition of 200: 1, described one section of catalyzer that catalyzer is alumina load tungsten nickel, the aluminum oxide that alumina supporter is used Beijing Chemical Research Institute to produce, the trade mark is BCA-31.In quality and the mass percent of catalyzer, one section of catalyzer contains 5% tungsten and 25% nickel, has 300m
2the specific surface area of/g and the pore volume of 0.7ml/g; After hydrogenation, material is through refrigerated separation gas, and separator pressure 0.18MPa, temperature 45 C, separate hydrogen and light hydrocarbon gas, and liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation, after cooling and isolating gas, then through being heated to 240 ℃, is mixed into hydrogen two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed, at reaction pressure 30Mpa, 270 ℃ of temperature, air speed 1.0h
-1, carry out secondary hydrogenation under the hydrogen to oil volume ratio condition of 200: 1, described two sections of catalyzer that catalyzer is the carrier loaded amorphous alloy nickel NiB of sepiolite, nickel content is 15%; After hydrogenation, material enters basin through refrigerated separation;
(5) stripping: will send into stripping tower after the feed separation gas after secondary hydrogenation, stripping tower reactor temperature is controlled at 250 ℃, solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin is out through the cooling granulator granulation packing of delivering to.
Embodiment 2
(1) preparation of raw material: the dicyclopentadiene that the mass content that Lanzhou Xin Lan chemical company is produced is 85%～95% and hexanaphthene are by weight mixing at 1: 1.5;
(2) polyreaction: the raw material of step (1) preparation is sent into preheater and be preheated to 210 ℃, then send into polymerization reactor, the 12 hours thermopolymerization time under 250～260 ℃ of temperature of reaction and pressure 2.1Mpa, obtain crude resin liquid;
(3) one-stage hydrogenation: make crude resin liquid through process furnace heating, 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 2.2Mpa, 300 ℃ of temperature, air speed 1.5h
-1with under the hydrogen to oil volume ratio condition of 300: 1, carry out one-stage hydrogenation, described one section of catalyzer that catalyzer is alumina load tungsten nickel; In quality and the mass percent of catalyzer, one section of catalyzer contains 3% tungsten and 15% nickel, has 180m
2the specific surface area of/g and the pore volume of 0.4ml/g; After hydrogenation, material is through refrigerated separation gas, and separator pressure 0.18MPa, temperature 45 C, separate hydrogen and light hydrocarbon gas, and liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation is through cooling and isolate after gas, then be mixed into through heating and hydrogen two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed, at reaction pressure 10Mpa, 290 ℃ of temperature, air speed 1.4h
-1with under the hydrogen to oil volume ratio condition of 300: 1, carry out secondary hydrogenation, 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: will send into stripping tower after cooling the material after secondary hydrogenation and divided gas flow, stripping tower reactor temperature is controlled at 255 ℃, solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin is out through the cooling tablets press of delivering to, and granulation, packs.
Embodiment 3
(1) preparation of raw material: the dicyclopentadiene that is 85%～95% by mass content and pentamethylene are by weight mixing at 1: 2.0;
(2) polyreaction: the raw material of step (1) preparation is sent into preheater and be preheated to 210 ℃, then send into polymerization reactor, the 9 hours thermopolymerization time under 250～260 ℃ of temperature of reaction and pressure 2.1Mpa, obtain crude resin liquid;
(3) one-stage hydrogenation: make crude resin liquid through process furnace heating, 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 2.8Mpa, 260 ℃ of temperature, air speed 0.5h
-1with under the hydrogen to oil volume ratio condition of 150: 1, carry out one-stage hydrogenation, described one section of catalyzer that catalyzer is alumina load tungsten nickel, alumina supporter use Beijing Chemical Research Institute produce aluminum oxide, the trade mark is BCA-31.In quality and the mass percent of catalyzer, one section of catalyzer contains 5% tungsten and 25% nickel, has 300m
2the specific surface area of/g and the pore volume of 0.7ml/g; After hydrogenation, material is through refrigerated separation gas, and separator pressure 0.18MPa, temperature 45 C, separate hydrogen and light hydrocarbon gas, and liquid material enters basin;
(4) secondary hydrogenation: the material after one-stage hydrogenation is through cooling and isolate after gas, then be mixed into through heating and hydrogen two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed, at reaction pressure 25Mpa, 275 ℃ of temperature, air speed 0.5h
-1with under the hydrogen to oil volume ratio condition of 150: 1, carry out secondary hydrogenation, 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: will send into stripping tower after cooling the material after secondary hydrogenation and divided gas flow, stripping tower reactor temperature is controlled at 260 ℃, solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin is out through the cooling tablets press of delivering to, and granulation, packs.
Compared with the dcpd resin of hydrogenation not, 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 fast light thermal characteristics is high, good stability while placing for a long time, nondiscoloration.
Claims (6)
1. hot polymerization and hydrogenation method are prepared a method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that said method comprising the steps of:
(1) preparation of raw material: the dicyclopentadiene that is 85%～95% by mass content and solvent mix by weight 1: 1.5～2.0;
(2) polyreaction: the raw material of step (1) preparation is sent into preheater and be preheated to 180～220 ℃, then send into polymerization reactor, 8～12 hours thermopolymerization time under 250～260 ℃ of temperature of reaction and pressure 2.1Mpa, obtain crude resin liquid;
(3) one-stage hydrogenation: make crude resin liquid through process furnace heating, 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 2.0～3.5Mpa, 260～300 ℃ of temperature, air speed 0.2～2.0h
-1with hydrogen to oil volume ratio 100～400: under 1 condition, carry out one-stage hydrogenation, described one section of catalyzer that catalyzer is alumina load tungsten and nickel;
(4) secondary hydrogenation: the material after one-stage hydrogenation is through cooling and isolate after gas, through heating and hydrogen, be mixed into two sections of high-pressure hydrogenation reactors that two sections of catalyzer are housed again, at reaction pressure 3.5～40Mpa, 260～300 ℃ of temperature, air speed 0.2～2.0h
-1with hydrogen to oil volume ratio 100～400: under 1 condition, carry out secondary hydrogenation, described two sections of catalyzer that catalyzer is the carrier loaded amorphous alloy nickel NiB of sepiolite;
(5) stripping: will send into stripping tower after cooling the material after secondary hydrogenation and divided gas flow, stripping tower reactor temperature is controlled at 240～260 ℃, solvent is extracted on stripping tower top out, and stripping tower bottom hydrogenation resin is out through the cooling tablets press of delivering to, and granulation, packs.
2. hot polymerization as claimed in claim 1 and hydrogenation method are prepared the method for hydrogenation dicyclopentadiene petroleum resin, 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 are prepared the method for hydrogenation dicyclopentadiene petroleum resin, 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 are prepared the method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that, the aluminum oxide that the alumina supporter of one section of described catalyzer is used Beijing Chemical Research Institute to produce, the trade mark is BCA-31, in quality and the mass percent of catalyzer, one section of catalyzer contains 3～5% tungsten and 10～25% nickel.
5. hot polymerization as claimed in claim 1 and hydrogenation method are prepared the method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that, two sections of described catalyzer that catalyzer is the carrier loaded amorphous alloy nickel NiB of sepiolite, in quality and the mass percent of catalyzer, nickel content is 10～25%.
6. hot polymerization as claimed in claim 1 and hydrogenation method are prepared the method for hydrogenation dicyclopentadiene petroleum resin, it is characterized in that, after the stripping of step (5), the solvent that extract out on stripping tower top is refining through distillation tower, and the solvent after refining can loop back step (1) and use.
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| 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 |
| CN106008820A (en) * | 2016-07-27 | 2016-10-12 | 朗盈科技（北京）有限公司 | Production system of low-chromaticity C5/C9 copolymerization hydrogenation resin and method |
| US11447581B2 (en) | 2017-12-29 | 2022-09-20 | Hanwha Solutions Corporation | Method for selective hydrogenation |
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| CN105585666A (en) * | 2014-10-22 | 2016-05-18 | 中国石油化工股份有限公司 | A preparing method of dicyclopentadiene hydrogenated petroleum resin |
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| CN105367714A (en) * | 2015-12-03 | 2016-03-02 | 大连理工大学 | Method for preparing hydrogenated DCPD resin |
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| CN105601815A (en) * | 2015-12-31 | 2016-05-25 | 庆阳永欣石油化工有限公司 | Preparing process and device for hydrogenated dicyclopentadiene petroleum resin and hydrogenation reaction kettle thereof |
| 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 |
| CN106008820A (en) * | 2016-07-27 | 2016-10-12 | 朗盈科技（北京）有限公司 | Production system of low-chromaticity C5/C9 copolymerization hydrogenation resin and method |
| US11447581B2 (en) | 2017-12-29 | 2022-09-20 | Hanwha Solutions Corporation | Method for selective hydrogenation |
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