CN102558444A - Method for preparing dicyclopentadiene hydrogenated petroleum resin - Google Patents
Method for preparing dicyclopentadiene hydrogenated petroleum resin Download PDFInfo
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Abstract
The invention relates to a method for preparing dicyclopentadiene hydrogenated petroleum resin. Dicyclopentadiene petroleum resin is used as a raw material and hydrogenated under the action of a catalyst to prepare the dicyclopentadiene hydrogenated petroleum resin, wherein the weight ratio of the dicyclopentadiene petroleum resin to the catalyst is 100: (3-6), the hydrogenating temperature is 170 to 215 DEG C, the pressure of the reaction hydrogen is 3.0 to 5.5MPa, and the reaction time is 4 to 8 hours; a silicon-aluminum composite oxide is used as a carrier in the catalyst, the active ingredient of the catalyst is Pd, the weight of the Pd is 0.1 to 1.0 percent of the weight of the catalyst, the specific surface of the catalyst is 350 to 420 m<2>/g, and the pore volume is 0.6 to 0.7ml/g; and according to the dicyclopentadiene hydrogenated petroleum resin product prepared by the method, the bromine number is less than or equal to 2.0gBr/100g, the chromaticity (Gardner) is less than or equal to 1, and the softening point is 110 to 120 DEG C.
Description
Technical field
The present invention relates to a kind of method of dicyclopentadiene petroleum resin hydrogenation preparing dicyclopentadiene hydrogenated petroleum resin.
Background technology
Dicyclopentadiene petroleum resin is to utilize the higher NSC 7352 of petroleum cracking system ethylene by-product article moderate purity to make through thermopolymerization; It is the relatively low thermoplastic hydrocarbon resin of a kind of number-average molecular weight; This resinoid has that form and aspect are dark, the unsaturated hydrocarbons linkage content high, thermostability and defective such as oxidative stability is low, cohesive force is relatively poor, with a lot of resinous substrates can not be compatible well, relatively poor as the tackifier result of use; Directly use seldom, need prepare high-grade petroleum resin through modification.
The simplest modification is exactly an adding hydrogen into resin; Petroleum resin degree of unsaturation behind the hydrogenation reduces greatly, form and aspect are shallow, no special odor; Remove and be used for aspects such as sticker, hot melt adhesive, Pressuresensitive Tape, ink printing and rubber; Be specially adapted to make and require that color is pure, the hot melt traffic paint of Heat stability is good, light footwear tackiness agent and food product pack articles for use, disposable paper diaper and sanitary napkin etc. are made the extraordinary tackiness agent of usefulness.
The hydrogenation technique that petroleum resin adopt can reduce substantially: slurry attitude hydrogenation, spray-type hydrogenation, fixed bed hydrogenation.Slurry attitude hydrogenation generally is an intermittent type, and is more suitable for less industrial scale or the evaluation of laboratory initial stage, but complex operation, catalyst loss is big; And the suitable mass-producing continuous production of fixed bed hydrogenation is more prone to middle-pressure process one-stage hydrogenation technology at present in the world.
The key of hydrogenation of petroleum resin technology is the exploitation of catalyzer; Patent US4384080 and US4540480 have described the hydrogenation of petroleum resin method of doing hydrogenation catalyst with precious metals such as nickel, palladium, platinum, rhenium, rutheniums; Adopting the compound of single-component metal or metal is active ingredient, and carrier adopts aluminum oxide and zeyssatite usually, adopts salt solution impregnation method prepared; Hydrogenated petroleum resin iodine number≤the 60g/100g that uses this catalyzer to obtain, Gardner colourity≤1.
The catalyzer that patent JP 07216019 describes is palladium/aluminum oxide, aperture>=0.7cm
3/ g, the thick polymers of resin continuous hydrogenation in fixed bed, temperature is 295～305 ℃, pressure is 90kg/cm
2, air speed 0.25h
-1, the hydrogenation resin yield that obtains is about 98%, 125 ℃ of softening temperatures, Gardner colourity≤5.
CN1485352 and CN1485353 have introduced the hydrogenation catalyst of dicyclopentadiene petroleum resin, and this catalyst activity component is Pd and Pt, and the content of Pd is 0.1～1.0wt%, and the content of Pt is 0.05～0.5wt%, and support of the catalyst is γ-Al
2O
3, its specific surface is 150～250m
2/ g, pore volume are 0.5～0.9ml/g.Adopt this change agent to carry out hydrogenation reaction, temperature is 220～320 ℃, and hydrogen pressure is 6.0～12.0MPa; Reaction times is 2～6 hours, and the hydrogenation resin unsaturated hydrocarbons linkage content that makes obviously reduces, and the resin form and aspect are improved to water white; Product bromine number≤5gBr/100g, 100～110 ℃ of softening temperatures.
CN101157029 has described a kind of dicyclopentadiene hydrogenation special-purpose catalyzer and preparation method thereof; The catalyst activity component is selected from a kind of among Pd or the Pt; Its weight percentage can be Pd0.3～1.3% or Pt0.5～1.2%, and carrier can be porous inorganic materials such as aluminum oxide, silicon oxide, molecular sieve, kaolin.Catalyzer is used for the relatively poor dicyclopentadiene petroleum resin hydrogenation of C5 fraction form and aspect, and temperature is 150～280 ℃, and hydrogen pressure is 6.0～10.0MPa, and air speed is 0.5～4.0h
-1, hydrogen-oil ratio is 100: 1～500: 1, product bromine number 1.5gBr/100g, 101～107 ℃ of softening temperatures, Gardner colourity≤2.
Common C5 fraction by cracking ethylene by-product separates in the NSC 7352 that obtains and contains more impurity; General purity has only about 80%; Other impurity that contain comprise isoprene, vinyl NSC 7352, methyl bicycle pentadiene, oxa-Fourth Ring hendecene, three cyclopentadiene, benzene and toluene etc.; The dicyclopentadiene petroleum resin that makes not only unsaturated hydrocarbons linkage content is high, and form and aspect are dark, and smell is heavy.After using existing catalyst hydrogenation, can not obtain form and aspect ideal hydrogenation resin, and hydrogenation temperature and pressure are higher, are unfavorable for suitability for industrialized production.
Summary of the invention
The method that the purpose of this invention is to provide a kind of dicyclopentadiene petroleum resin hydrogenation preparing dicyclopentadiene hydrogenated petroleum resin.The catalyst activity height that present method is used; Can reduce use temperature and working pressure; Facility investment and working cost are reduced, and the hydrogenated petroleum resin unsaturated double-bond content that makes is low, thermostability and oxidative stability are good, and form and aspect are also improved completely.
The method for preparing dicyclopentadiene hydrogenated petroleum resin of the present invention, catalyst system therefor is a carrier with the sial composite oxides, and active ingredient is Pd, and Pd weight is 0.1～1.0%, and Pd the best is 0.3～0.7%, its specific surface is 350～420m
2/ g, pore volume are 0.6～0.7ml/g, and support shapes can be bar shaped or other special-shaped outward appearances that helps transmitting.
Preparation of Catalyst adopts pickling process well known to those skilled in the art, at first prepares carrier, and load P d is dried behind the mixture ageing then, after high-temperature roasting, just makes finished catalyst.
The preparation of carrier: with water, water glass, HNO
3By weight (40～50): (1.5～2): 1 adds in the there-necked flask, and control pH value is 8.0～8.4, is warmed up to 45～55 ℃, and drip to add volume ratio be 1.2～1.8 15% AlCl
3With 10%～12% NH
3H
2O solution, control pH value 8.5～8.7 dropwises, and 60 ℃ of aging 30min filter; Filter cake is put into autoclave, and add NH
4HCO
3Solution, heat temperature raising to 130 ℃ crystallization 3hr cools to 60 ℃ of aging 30min again, filters, and filter cake obtains the sial macroporous oxide through washing, filtration, oven dry, pulverizing; Get sieve and silica-sesquioxide and Al
2O
3, mixed by weight 1.5: 1, add volume ratio again and be 6: 5: 1 3%HNO
3, 2.5% Hydrocerol A, 0.5% urotropine mixing solutions, it is kneaded and formed to put into kneader, 120 ℃ of dry 10hr; 970 ℃ of roasting 4hr.
Pd carrying method: take by weighing PdCl in proportion
2, be dissolved among rare HCl, and be diluted in the carrier equal-volume; The carrier that has prepared is put into steeping vat, pour above-mentioned PdCl into
2Solution is in 50 ℃ of dipping 60min; Reduce with Hydrazine Hydrate 80, wash twice then to no chlorine, filter cake was in 120～150 ℃ of oven dry 8～10 hours; Calcined 6 hours for 500～550 ℃, it is subsequent use to obtain finished catalyst.
Evaluating catalyst: at first catalyzer reduces; Then dicyclopentadiene petroleum resin is carried out hydrogenation reaction in organic solvent in the presence of catalyzer, the weight ratio of dicyclopentadiene petroleum resin and catalyzer 100: 3～6, temperature of reaction are 170～215 ℃; The reaction hydrogen pressure is 3.0～5.5MPa; Reaction times is 4～8h, hydrogenation products through filter, often reduce pressure desolventizing and low-boiling-point substance, cooling forming obtains the hydrogenated petroleum resin product.Above-mentioned organic solvent can be selected any in normal hexane, hexanaphthene, methylcyclohexane, the sherwood oil usually for use.
Advantages such as key of the present invention has been to select suitable sial composite oxide carrier, and it is abundant to have pore structure, and pore volume, specific surface area are big.Find that through experiment this catalyzer is used for the dicyclopentadiene petroleum resin hydrogenation technique, can significantly reduce hydrogenation pressure, hydrogenation pressure is 3.0～5.5MPa, is 6.0～10.0MPa and use other catalyzer pressure; Demonstrate beyond thought effect to improving dicyclopentadiene petroleum resin form and aspect aspect, can make form and aspect is to be improved as form and aspect behind Gardner's 10～No. 12 the adding hydrogen into resin to be Gardner No. 1.
Method provided by the present invention compared with prior art has following advantage:
(1) this catalyzer has been selected suitable sial composite oxide carrier; Precious metals pd is an active ingredient, and on carrier, is the nanometer distribution, has the pore structure of enriching; The active ingredient dispersity is high, specific surface area is big, can obtain the new catalyst of high reactivity, high thermal stability.
(2) adopt catalyzer of the present invention through a hydrogenation, the resin unsaturated link(age) obviously reduces, and form and aspect are improved to water white, product bromine number≤2.0gBr/100g, colourity (Gardner)≤1,110～120 ℃ of softening temperatures.
(3) catalyst activity of the present invention is high, can significantly reduce hydrogenation temperature and hydrogenation pressure, can omit the secondary hydrogenation technique, and facility investment and working cost are reduced, and helps industrializing implementation.
Embodiment
In an embodiment, the testing method of each index is following:
Softening temperature: ring and ball method (GB4507-1999)
Form and aspect: color of transparent liquids measuring method (Gardner's colourity) (GB22295-2008)
Bromine number: Ka Erfeixiu potentiometric titration (GB11135-2008)
Dicyclopentadiene petroleum resin raw material index:
Softening temperature (℃) 120
Bromine number (gBr/100g) 88
Colourity (Gardner) 10
Embodiment 1:
(1) Preparation of catalysts
(1) preparation of carrier
Take by weighing water 2000ml, 26% water glass 342g, 25% HNO
3145ml adds in the there-necked flask, and the control pH value is 8.0～8.4, be warmed up to 45～55 ℃, and drip adds 15%AlCl
3Solution 3000ml and 11% NH
3H
2O solution 2150ml, control pH value 8.5～8.7, control AlCl
3Flow 90ml/min dropwises, and 60 ℃ of aging 30min filter; Filter cake is put into autoclave, and add 87% NH
4HCO
3Solution 175g, heat temperature raising to 130 ℃ crystallization 3hr cools to 60 ℃ of aging 30min again.Add 5000ml water in the filter cake, stir 30min down, filter in 60 ℃; 150 ℃ of oven dry of filter cake 10h pulverizes and obtains sial macroporous oxide 342g.
Get sieve and silica-sesquioxide 300g, Al
2O
3200g, adding 3%HNO
3, 0.5% urotropine, 2.5% Hydrocerol A mixing solutions 500ml, put into kneader and mediate, extruded moulding is in 120 ℃ of dry 10hr; 970 ℃ of roasting 4hr obtain support of the catalyst.
(2) Pd carrying method
Get 0.58gPdCl
2, add 0.25%HCl60ml, heated and boiled 30min, the dissolving postcooling makes PdCl
2Solution; Get the 70g carrier and put into steeping vat, pour above-mentioned PdCl into
2Solution is in 50 ℃ of dipping 60min; Add 5% Hydrazine Hydrate 80 100ml, reduction 1h under 50 ℃; Use 200ml water washing twice then, filter cake was in 120～150 ℃ of oven dry 8～10 hours; Calcined 6 hours for 500～550 ℃, obtain finished catalyst, the weight content of palladium is 0.5% in the catalyzer.
(2) hydrogenation evaluation
In the 2L autoclave that band stirs, add catalyzer; Through nitrogen replacement, hydrogen reducing, add then with the good dicyclopentadiene petroleum resin of hexanaphthene dissolving, solvent: the weight ratio of portions of resin catalyzer is 200: 100: 3; With hydrogen the air in the still is fully replaced; Then hydrogen pressure is charged to 3.0MPa, begins to heat up, start and stir.Control reaction temperature is 200 ℃, and the reaction times is 5h.Hydrogenation products through filter, often reduce pressure desolventizing and low-boiling-point substance, cooling forming obtains hydrogenated petroleum resin, 115 ℃ of product softening temperatures, bromine number 1.2gBr/100g, colourity is Gardner No. 1.
Embodiment 2:
Preparing carriers is with embodiment 1.Get 0.82gPdCl
2, add 0.25%HCl60ml, heated and boiled 30min, the dissolving postcooling makes PdCl
2Solution; Get the 70g carrier and put into steeping vat, pour above-mentioned PdCl into
2Solution is in 50 ℃ of dipping 60min; Add 5% Hydrazine Hydrate 80 100ml, reduction 1h under 50 ℃; Use 200ml water washing twice then, filter cake was in 120～150 ℃ of oven dry 8～10 hours; Calcined 6 hours for 500～550 ℃, obtain finished catalyst, the weight content of palladium is 0.7% in the catalyzer.
In the 2L autoclave that band stirs, add catalyzer; Through nitrogen replacement, hydrogen reducing, add then with the good dicyclopentadiene petroleum resin of hexanaphthene dissolving, solvent: the weight ratio of portions of resin catalyzer is 200: 100: 5; With hydrogen the air in the still is fully replaced; Then hydrogen pressure is charged to 3.5MPa, begins to heat up, start and stir.Control reaction temperature is 180 ℃, and the reaction times is 6h.Hydrogenation products through filter, often reduce pressure desolventizing and low-boiling-point substance, cooling forming obtains hydrogenated petroleum resin, 118 ℃ of product softening temperatures, bromine number 1.0gBr/100g, colourity is Gardner No. 1.
Embodiment 3:
Preparing carriers is with embodiment 1.Get 0.35gPdCl
2, add 0.25%HCl60ml, heated and boiled 30min, the dissolving postcooling makes PdCl
2Solution; Get the 70g carrier and put into steeping vat, pour above-mentioned PdCl into
2Solution is in 50 ℃ of dipping 60min; Add 5% Hydrazine Hydrate 80 100ml, reduction 1h under 50 ℃; Use 200ml water washing twice then, filter cake was in 120～150 ℃ of oven dry 8～10 hours; Calcined 6 hours for 500～550 ℃, obtain finished catalyst, the weight content of palladium is 0.3% in the catalyzer.
In the 2L autoclave that band stirs, add catalyzer; Through nitrogen replacement, hydrogen reducing, add then with the good dicyclopentadiene petroleum resin of hexanaphthene dissolving, solvent: the weight ratio of portions of resin catalyzer is 200: 100: 6; With hydrogen the air in the still is fully replaced; Then hydrogen pressure is charged to 5.5MPa, begins to heat up, start and stir.Control reaction temperature is 215 ℃, and the reaction times is 4h.Hydrogenation products through filter, often reduce pressure desolventizing and low-boiling-point substance, cooling forming obtains hydrogenated petroleum resin, 114 ℃ of product softening temperatures, bromine number 1.7gBr/100g, colourity is Gardner No. 1.
Embodiment 4:
Preparing carriers is with embodiment 1.Get 1.16gPdCl
2, add 0.25%HCl60ml, heated and boiled 30min, the dissolving postcooling makes PdCl
2Solution; Get the 70g carrier and put into steeping vat, pour above-mentioned PdCl into
2Solution is in 50 ℃ of dipping 60min; Add 5% Hydrazine Hydrate 80 120ml, reduction 1h under 50 ℃; Use 200ml water washing twice then, filter cake was in 120～150 ℃ of oven dry 8～10 hours; Calcined 6 hours for 500～550 ℃, obtain finished catalyst, the weight content of palladium is 1.0% in the catalyzer.
In the 2L autoclave that band stirs, add catalyzer; Through nitrogen replacement, hydrogen reducing, add then with the good dicyclopentadiene petroleum resin of hexanaphthene dissolving, solvent: the weight ratio of portions of resin catalyzer is 200: 100: 3; With hydrogen the air in the still is fully replaced; Then hydrogen pressure is charged to 4.5MPa, begins to heat up, start and stir.Control reaction temperature is 170 ℃, and the reaction times is 8h.Hydrogenation products through filter, often reduce pressure desolventizing and low-boiling-point substance, cooling forming obtains hydrogenated petroleum resin, 116 ℃ of product softening temperatures, bromine number 0.8gBr/100g, colourity is Gardner No. 1.
Embodiment 5:
Carrier and Preparation of Catalyst are with embodiment 1, and the weight content of palladium is 0.5% in the catalyzer.
In the 2L autoclave that band stirs, add catalyzer; Through nitrogen replacement, hydrogen reducing, add then with the good dicyclopentadiene petroleum resin of hexanaphthene dissolving, solvent: the weight ratio of portions of resin catalyzer is 200: 100: 5; With hydrogen the air in the still is fully replaced; Then hydrogen pressure is charged to 3.0MPa, begins to heat up, start and stir.Control reaction temperature is 190 ℃, and the reaction times is 6h.Hydrogenation products through filter, often reduce pressure desolventizing and low-boiling-point substance, cooling forming obtains hydrogenated petroleum resin, 118 ℃ of product softening temperatures, bromine number 0.6gBr/100g, colourity is Gardner No. 1.
Claims (2)
1. method for preparing dicyclopentadiene hydrogenated petroleum resin; It is characterized in that: be raw material with the dicyclopentadiene petroleum resin; Hydrogenation preparing dicyclopentadiene hydrogenated petroleum resin under catalyst action, the weight ratio of dicyclopentadiene petroleum resin and catalyzer 100: 3～6, hydrogenation temperature is 170～215 ℃; The reaction hydrogen pressure is 3.0～5.5MPa, and the reaction times is 4～8h;
Catalyzer is a carrier with the sial composite oxides, and active ingredient is Pd, and Pd weight is 0.1～1.0% of catalyst weight, its specific surface 350～420m
2/ g, pore volume 0.6～0.7ml/g;
Preparation of catalysts:
With water, water glass, HNO
3By weight (40～50): (1.5～2): 1 adds in the there-necked flask, and control pH value is 8.0～8.4, is warmed up to 45～55 ℃, and drip to add volume ratio be 1.2～1.8 15% AlCl
3With 10%～12% NH
3H
2O solution, control pH value 8.5～8.7 dropwises, and 60 ℃ of aging 30min filter; Filter cake is put into autoclave, and add NH
4HCO
3Solution, heat temperature raising to 130 ℃ crystallization 3hr cools to 60 ℃ of aging 30min again, filters, and filter cake obtains the sial macroporous oxide through washing, filtration, oven dry, pulverizing; Get sieve and silica-sesquioxide and Al
2O
3, mixed by weight 1.5: 1, add volume ratio again and be 6: 5: 1 3%HNO
3, 2.5% Hydrocerol A, 0.5% urotropine mixing solutions, it is kneaded and formed to put into kneader, 120 ℃ of dry 10hr; 970 ℃ of roasting 4hr.
2. hydrogenation catalyst according to claim 1, the content the best that it is characterized in that described catalyst activity component Pd is 0.3～0.7wt%.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360547A (en) * | 2013-06-25 | 2013-10-23 | 朗盈科技（北京）有限公司 | System and method for producing dicyclopentadiene hydrogenated petroleum resin |
| CN103724544A (en) * | 2013-12-25 | 2014-04-16 | 陈国兴 | Preparation method of hydrogenated dicyclopentadiene resin |
| 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 |
| 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 |
| CN108329429A (en) * | 2018-03-07 | 2018-07-27 | 宁波金海晨光化学股份有限公司 | A kind of continuous method for preparing light dicyclopentadiene petroleum resin |
| CN111234056A (en) * | 2020-01-20 | 2020-06-05 | 恒河材料科技股份有限公司 | Catalyst for hydrogenation of hydrocarbon-containing petroleum resin |
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| US20030100809A1 (en) * | 2001-09-29 | 2003-05-29 | Baoliang Tian | Process for separating C5 cuts obtained from a petroleum cracking process |
| CN1485352A (en) * | 2002-09-24 | 2004-03-31 | 中国石化上海石油化工股份有限公司 | Hydrogenation catalyst for preparing dicyclopentadiene hydrogenated petroleum resin |
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2010
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030100809A1 (en) * | 2001-09-29 | 2003-05-29 | Baoliang Tian | Process for separating C5 cuts obtained from a petroleum cracking process |
| CN1485352A (en) * | 2002-09-24 | 2004-03-31 | 中国石化上海石油化工股份有限公司 | Hydrogenation catalyst for preparing dicyclopentadiene hydrogenated petroleum resin |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360547A (en) * | 2013-06-25 | 2013-10-23 | 朗盈科技（北京）有限公司 | System and method for producing dicyclopentadiene hydrogenated petroleum resin |
| CN103724544A (en) * | 2013-12-25 | 2014-04-16 | 陈国兴 | Preparation method of hydrogenated dicyclopentadiene resin |
| CN103724544B (en) * | 2013-12-25 | 2016-03-09 | 陈国兴 | The preparation method of hydrogenation dcpd resin |
| 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 |
| 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 |
| 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 |
| CN108329429A (en) * | 2018-03-07 | 2018-07-27 | 宁波金海晨光化学股份有限公司 | A kind of continuous method for preparing light dicyclopentadiene petroleum resin |
| CN108329429B (en) * | 2018-03-07 | 2020-08-21 | 宁波金海晨光化学股份有限公司 | Method for continuously preparing light-colored dicyclopentadiene petroleum resin |
| CN111234056A (en) * | 2020-01-20 | 2020-06-05 | 恒河材料科技股份有限公司 | Catalyst for hydrogenation of hydrocarbon-containing petroleum resin |
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