CN105273134B - A kind of preparation method and application of alkalinity rosin polymer catalyst - Google Patents
A kind of preparation method and application of alkalinity rosin polymer catalyst Download PDFInfo
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Abstract
The present invention relates to a kind of organic solid base catalysts, more particularly to a kind of preparation method and application for the alkaline rosin polymer catalyst for being used to synthesize cinnamic acid, the alkalinity rosin polymer catalyst is using levopimaric acid, acrylic acid and hydroxy-ethyl acrylate as raw material, and synthesis obtains monomer 1；Using 2 aminopyridines and acryloyl chloride monomer 2 is obtained as Material synthesis；Then the suspension polymerisation of oil-in-water type is used, adds in what polyethylene of dispersing agent alcohol, monomer 1, monomer 2 and initiator azo-bis-isobutyl cyanide polymerisation obtained；The alkaline rosin polymer catalyst that the present invention is prepared has high catalytic activity and reusable, for synthesizing cinnamic acid, can effectively be catalyzed benzaldehyde and acetaldehyde reaction generation cinnamic acid, excellent catalytic effect, and the yield that cinnamic acid is obtained by the reaction is also higher.
Description
Technical field
The present invention relates to a kind of organic solid base catalysts, and in particular to a kind of to gather for synthesizing the alkaline rosin of cinnamic acid
The preparation method and application of mixture catalyst.
Background technology
Cinnamic acid, scientific name cinnamaldehyde, cinnamic aldehyde are pale yellow oily liquids, have strong green meat perfume.Fusing point-
7.5 DEG C, 253 DEG C of boiling point.Cinnamic acid is important fragrance, is mainly used for modulating the daily essences such as Su Xin, the lily of the valley, rose.Together
When also have extensive biological function, if any antibacterial, it is antiviral and antitumor the effects that；There is health-care effect to humans and animals；It is right
Food acts on, and have corrosion-resistanting fresh-keeping effect with the existing flavouring of feed product.As antibiotic and artificial synthesized antibacterials are raised
Feed additives will likely be stopped due to its toxic side effect（Prohibit）With cinnamic acid will likely be got over as a kind of novel feed addictive
Carry out more extensive use.
The synthetic method of cinnamic acid routine is using benzaldehyde and acetaldehyde as raw material, and in alcohol solution, NaOH catalysis is lower to contract
It closes and is made.Since benzaldehyde is not soluble in water under room temperature, building-up process generally requires strong mixing so that reactant is abundant with catalyst
Contact or using phase transfer catalyst, needs to neutralize, is inevitably generated salt waste, therefore after NaOH catalyst reactions
Existing synthesis technology blowdown flow rate is big, and environmental pollution is serious.
Invention content
The purpose of the present invention is to provide a kind of for synthesizing the preparation side of the alkaline rosin polymer catalyst of cinnamic acid
Method and its application, which, which has high catalytic activity, can simultaneously recycle, for catalyzing and synthesizing cinnamic acid, catalytic effect
It is good.
To achieve these goals, the present invention is realized by following technology case：
A kind of preparation method of alkalinity rosin polymer catalyst, step are as follows：
（1）The synthesis of monomeric compound 1：
It is first added in levopimaric acid at 175-185 DEG C, reacts 30 minutes or more by polymerization inhibitor of hydroquinone,
Then acrylic acid is added in, at 230-240 DEG C, 3-5h is reacted, obtains rosin acrylic acid, then by rosin acrylic acid and acrylic acid
Hydroxyl ethyl ester is raw material, back flow reaction 3.5-6h, synthon compound 1；
（2）The synthesis of monomeric compound 2：
2-aminopyridine is dissolved with dichloromethane, under ice bath, acryloyl chloride reaction 0.5-1 h is added in, adds and tie up acid
Agent, after reacting 10-20min, heating reflux reaction 4-5.5 h, synthon compound 2；
（3）The preparation of catalyst：
Using azo-bis-isobutyl cyanide as initiator, polyvinyl alcohol is dispersant, by azo-bis-isobutyl cyanide, polyvinyl alcohol and molten
Solution has monomeric compound 1 and the oil-dissolving solvent of monomeric compound 2 to be reacted, and in the case where temperature is 65-70 DEG C, reacts 2-4h,
Alkalinity rosin polymer catalyst is made.
In the preparation method of above-mentioned alkalinity rosin polymer catalyst, the step（1）The synthesis of monomeric compound 1
Concrete operation step is：
According to weight ratio levopimaric acid：Hydroquinone is 165-175:1 ratio is by levopimaric acid and hydroquinone
It is placed in reaction kettle, is warming up to 175-185 DEG C, isomerization reaction 30 minutes or more after separating water, adds in acrylic acid, acrylic acid
Addition is 0.2-0.4 times that levopimaric acid adds in quality, is warming up to 230-240 DEG C, reacts 3-5h, obtains propylene Korean pine
Acid takes rosin acrylic acid to be placed in reaction kettle, adds in the thionyl chloride of 95-100 times of propylene Korean pine weight, heating reflux reaction 5-7
After h, thionyl chloride excessive in reaction kettle is removed, adds in thiacyclohexane and propylene that rosin acrylic acid adds in 18-23 times of weight
Pimaric acid adds in the hydroxy-ethyl acrylate of 1-1.4 times of weight, after back flow reaction 3.5-6h, monomer chemical combination will be obtained after purification of products
Object 1.
In the preparation method of above-mentioned alkalinity rosin polymer catalyst, the step（2）The synthesis of monomeric compound 2
Concrete operation step is：
Quantitative 2-aminopyridine is dissolved in dichloromethane, under ice bath, adds in 1-2 times of 2-aminopyridine weight
Acryloyl chloride after reacting 0.5-1 h, adds in the acid binding agent of 4.8-5.5 times of 2-aminopyridine weight, after reacting 10-20min, adds
Hot back flow reaction 4-5.5 h, obtain reaction product；Monomeric compound 2 will be obtained after purification of products.
Step（2）In the synthesis of monomeric compound 2, the acid binding agent be organic base or inorganic base, including triethylamine,
Pyridine, sodium carbonate, potassium carbonate.
In the preparation method of above-mentioned alkalinity rosin polymer catalyst, the step（3）The preparation of catalyst it is specific
Operating procedure is：
By the reacting dose of polyvinyl alcohol, monomeric compound 1, monomeric compound 2 and azo-bis-isobutyl cyanide according to by weight
Than polyvinyl alcohol：Monomeric compound 1：Monomeric compound 2：Azo-bis-isobutyl cyanide is 0.1-0.5：1.5-7.5：1.1-6：0.1-
0.5 ratio is reacted, and first polyvinyl alcohol is dissolved in the water, and then, adds in azo-bis-isobutyl cyanide and dissolved with monomer
The oil-dissolving solvent of compound 1 and monomeric compound 2 is heated with stirring to 65-70 DEG C of temperature, after reacting 2-4h, is cooled to room
Temperature after product is filtered, washed and dried, obtains alkaline rosin polymer catalyst.
Step（3）In the preparation of catalyst, the oil-dissolving solvent includes petroleum ether, hexamethylene, benzene, toluene and diformazan
Benzene.
It is applied in cinnamic acid is synthesized the alkaline rosin polymer catalyst that the present invention is prepared, the behaviour of concrete application
As：Benzaldehyde in molar ratio：Acetaldehyde is 1：The ratio of 1-1.2 mixes benzaldehyde with acetaldehyde, and adds in benzaldehyde weight 4-
Reaction 3-9 hours is stirred at room temperature in 6% alkaline rosin polymer catalyst, obtains product after separation is distilled, yield is
33%-67%。
Beneficial effects of the present invention are：
1st, the present invention provides a kind of preparation method and applications of alkaline rosin polymer catalyst, preparation method behaviour
Make simplicity, the catalyst being prepared is a kind of organic solid base catalyst, for catalyzing and synthesizing cinnamic acid, can recycle and follow
Ring uses, and cinnamic acid is synthesized and pollution on the environment relative to conventional use of NaOH catalyst, uses present invention system
Standby obtained alkaline rosin polymer catalyst not can cause environmental pollution, but also reusable to synthesize cinnamic acid,
Repeat performance is good.
2nd, the alkaline rosin polymer catalyst that the present invention is prepared, has high catalytic activity, in synthesis cinnamic acid
In reaction, it can effectively be catalyzed benzaldehyde and acetaldehyde reacts and generates cinnamic acid, excellent catalytic effect, the yield of cinnamic acid is obtained by the reaction
Also it is higher.
Description of the drawings
Fig. 1 is the structural formula of alkaline rosin polymer catalyst that the present invention is prepared.
Specific embodiment
Embodiment 1
A kind of preparation method of alkalinity rosin polymer catalyst, step are as follows：
（1）The synthesis of monomeric compound 1：
According to weight ratio levopimaric acid：Hydroquinone is 165:Levopimaric acid and hydroquinone are placed in by 1 ratio
In reaction kettle, it is warming up to 175 DEG C, isomerization reaction 30 minutes or more after separating water, adds in acrylic acid, acrylic acid addition is
Levopimaric acid adds in 0.2 times of quality, is warming up to 230 DEG C, reacts 3h, obtains rosin acrylic acid, rosin acrylic acid is taken to be placed in
Reaction kettle, adds in the thionyl chloride of 95 times of propylene Korean pine weight, after heating reflux reaction 5h, removes dichloro excessive in reaction kettle
Sulfoxide adds in the acrylic acid hydroxyl second that rosin acrylic acid adds in the thiacyclohexane of 18 times of weight and rosin acrylic acid adds in 1 times of weight
Ester after back flow reaction 3.5h, will obtain monomeric compound 1 after purification of products；
（2）The synthesis of monomeric compound 2：
Quantitative 2-aminopyridine is dissolved in dichloromethane, under ice bath, adds in the third of 1 times of 2-aminopyridine weight
Alkene acyl chlorides after reacting 0.5h, adds in the acid binding agent triethylamine of 4.8 times of 2-aminopyridine weight, after reacting 10min, is heated to reflux
4h is reacted, obtains reaction product；Monomeric compound 2 will be obtained after purification of products；
（3）The preparation of catalyst：
By the reacting dose of polyvinyl alcohol, monomeric compound 1, monomeric compound 2 and azo-bis-isobutyl cyanide according to by weight
Than polyvinyl alcohol：Monomeric compound 1：Monomeric compound 2：Azo-bis-isobutyl cyanide is 0.1：1.5：1.1：0.1 ratio carries out anti-
Should, first polyvinyl alcohol is dissolved in the water, then, adds in azo-bis-isobutyl cyanide and dissolved with monomeric compound 1 and singulation
The oil-dissolving solvent petroleum ether of object 2 is closed, is heated with stirring to 65 DEG C of temperature, after reacting 4h, is cooled to room temperature, product is filtered, washed
After drying, alkaline rosin polymer catalyst is obtained.
Embodiment 2
A kind of preparation method of alkalinity rosin polymer catalyst, step are as follows：
（1）The synthesis of monomeric compound 1：
According to weight ratio levopimaric acid：Hydroquinone is 168:Levopimaric acid and hydroquinone are placed in by 1 ratio
In reaction kettle, it is warming up to 180 DEG C, isomerization reaction 30 minutes or more after separating water, adds in acrylic acid, acrylic acid addition is
Levopimaric acid adds in 0.27 times of quality, is warming up to 233 DEG C, reacts 4h, obtains rosin acrylic acid, rosin acrylic acid is taken to put
In reaction kettle, the thionyl chloride of 96 times of propylene Korean pine weight is added in, after heating reflux reaction 6h, remove excessive two in reaction kettle
Chlorine sulfoxide adds in the acrylic acid that rosin acrylic acid adds in the thiacyclohexane of 20 times of weight and rosin acrylic acid adds in 1.2 times of weight
Hydroxyl ethyl ester after back flow reaction 4.5h, will obtain monomeric compound 1 after purification of products；
（2）The synthesis of monomeric compound 2：
Quantitative 2-aminopyridine is dissolved in dichloromethane, under ice bath, adds in 1.3 times of 2-aminopyridine weight
Acryloyl chloride after reacting 0.7 h, adds in the acid binding agent pyridine of 5.0 times of 2-aminopyridine weight, after reacting 14min, is heated to reflux
4.5 h are reacted, obtain reaction product；Monomeric compound 2 will be obtained after purification of products；
（3）The preparation of catalyst：
By the reacting dose of polyvinyl alcohol, monomeric compound 1, monomeric compound 2 and azo-bis-isobutyl cyanide according to by weight
Than polyvinyl alcohol：Monomeric compound 1：Monomeric compound 2：Azo-bis-isobutyl cyanide is 0.3：3.5：3：0.3 ratio carries out anti-
Should, first polyvinyl alcohol is dissolved in the water, then, adds in azo-bis-isobutyl cyanide and dissolved with monomeric compound 1 and singulation
The oil-dissolving solvent hexamethylene of object 2 is closed, is heated with stirring to 65-70 DEG C of temperature, after reacting 3h, is cooled to room temperature, product filtering,
After washing and drying, alkaline rosin polymer catalyst is obtained.
Embodiment 3
A kind of preparation method of alkalinity rosin polymer catalyst, step are as follows：
（1）The synthesis of monomeric compound 1：
According to weight ratio levopimaric acid：Hydroquinone is 171:Levopimaric acid and hydroquinone are placed in by 1 ratio
In reaction kettle, it is warming up to 182 DEG C, isomerization reaction 30 minutes or more after separating water, adds in acrylic acid, acrylic acid addition is
Levopimaric acid adds in 0.32 times of quality, is warming up to 236 DEG C, reacts 4.5h, obtains rosin acrylic acid, rosin acrylic acid is taken to put
In reaction kettle, the thionyl chloride of 98 times of propylene Korean pine weight is added in, after heating reflux reaction 6.5h, remove excessive in reaction kettle
Thionyl chloride adds in the propylene that rosin acrylic acid adds in the thiacyclohexane of 22 times of weight and rosin acrylic acid adds in 1.3 times of weight
Sour hydroxyl ethyl ester after back flow reaction 5.5h, will obtain monomeric compound 1 after purification of products；
（2）The synthesis of monomeric compound 2：
Quantitative 2-aminopyridine is dissolved in dichloromethane, under ice bath, adds in 1.6 times of 2-aminopyridine weight
Acryloyl chloride after reacting 0.8 h, adds in the acid binding agent sodium carbonate of 5.3 times of 2-aminopyridine weight, after reacting 18min, heats back
Stream reaction 5.0h, obtains reaction product；Monomeric compound 2 will be obtained after purification of products；
（3）The preparation of catalyst：
By the reacting dose of polyvinyl alcohol, monomeric compound 1, monomeric compound 2 and azo-bis-isobutyl cyanide according to by weight
Than polyvinyl alcohol：Monomeric compound 1：Monomeric compound 2：Azo-bis-isobutyl cyanide is 0.4：6：4.3：0.4 ratio carries out anti-
Should, first polyvinyl alcohol is dissolved in the water, then, adds in azo-bis-isobutyl cyanide and dissolved with monomeric compound 1 and singulation
Close the oil-dissolving solvent benzene of object 2, be heated with stirring to 68 DEG C of temperature, after reacting 3.5h, be cooled to room temperature, product be filtered, washed and
After drying, alkaline rosin polymer catalyst is obtained.
Embodiment 4
A kind of preparation method of alkalinity rosin polymer catalyst, step are as follows：
（1）The synthesis of monomeric compound 1：
According to weight ratio levopimaric acid：Hydroquinone is 175:Levopimaric acid and hydroquinone are placed in by 1 ratio
In reaction kettle, it is warming up to 185 DEG C, isomerization reaction 30 minutes or more after separating water, adds in acrylic acid, acrylic acid addition is
Levopimaric acid adds in 0.4 times of quality, is warming up to 240 DEG C, reacts 5h, obtains rosin acrylic acid, rosin acrylic acid is taken to be placed in
Reaction kettle, adds in the thionyl chloride of 100 times of propylene Korean pine weight, after heating reflux reaction 7h, removes excessive two in reaction kettle
Chlorine sulfoxide adds in the acrylic acid that rosin acrylic acid adds in the thiacyclohexane of 23 times of weight and rosin acrylic acid adds in 1.4 times of weight
Hydroxyl ethyl ester after back flow reaction 6h, will obtain monomeric compound 1 after purification of products；
（2）The synthesis of monomeric compound 2：
Quantitative 2-aminopyridine is dissolved in dichloromethane, under ice bath, adds in the third of 2 times of 2-aminopyridine weight
Alkene acyl chlorides after reacting 1 h, adds in the acid binding agent potassium carbonate of 5.5 times of 2-aminopyridine weight, after reacting 20min, is heated to reflux anti-
5.5h is answered, obtains reaction product；Monomeric compound 2 will be obtained after purification of products；
（3）The preparation of catalyst：
By the reacting dose of polyvinyl alcohol, monomeric compound 1, monomeric compound 2 and azo-bis-isobutyl cyanide according to by weight
Than polyvinyl alcohol：Monomeric compound 1：Monomeric compound 2：Azo-bis-isobutyl cyanide is 0.5：7.5：6：0.5 ratio carries out anti-
Should, first polyvinyl alcohol is dissolved in the water, then, adds in azo-bis-isobutyl cyanide and dissolved with monomeric compound 1 and singulation
The oil-dissolving solvent toluene or dimethylbenzene of object 2 are closed, is heated with stirring to 70 DEG C of temperature, after reacting 2h, is cooled to room temperature, product mistake
After filter, washing and drying, alkaline rosin polymer catalyst is obtained.
Application Example 1
By the alkaline rosin polymer catalyst being prepared in embodiment 1 for synthesizing cinnamic acid, concrete operations are：It presses
Molar ratio benzaldehyde：Acetaldehyde is 1：1 ratio mixes benzaldehyde with acetaldehyde, and the alkaline rosin for adding in benzaldehyde weight 4% gathers
Reaction 3 hours is stirred at room temperature in mixture catalyst, and product is obtained after separation is distilled, and yield is 33 %.
Application Example 2
By the alkaline rosin polymer catalyst being prepared in embodiment 2 for synthesizing cinnamic acid, concrete operations are：It presses
Molar ratio benzaldehyde：Acetaldehyde is 1：1.1 ratio mixes benzaldehyde with acetaldehyde, and adds in the alkaline rosin of benzaldehyde weight 5%
Reaction 5 hours is stirred at room temperature in polyalcohol catalyst, and product, yield 50% are obtained after separation is distilled.
Application Example 3
By the alkaline rosin polymer catalyst being prepared in embodiment 3 for synthesizing cinnamic acid, concrete operations are：It presses
Molar ratio benzaldehyde：Acetaldehyde is 1：1.2 ratio mixes benzaldehyde with acetaldehyde, and adds in the alkaline rosin of benzaldehyde weight 6%
Reaction 8 hours is stirred at room temperature in polyalcohol catalyst, and product, yield 67% are obtained after separation is distilled.
Application Example 4
By the alkaline rosin polymer catalyst being prepared in embodiment 4 for synthesizing cinnamic acid, concrete operations are：It presses
Molar ratio benzaldehyde：Acetaldehyde is 1：1.2 ratio mixes benzaldehyde with acetaldehyde, and adds in the alkaline rosin of benzaldehyde weight 5%
Reaction 9 hours is stirred at room temperature in polyalcohol catalyst, and product, yield 59% are obtained after separation is distilled.
It can be seen that from Application Example：The alkaline rosin polymer catalyst that the present invention is prepared, for synthesizing
Cinnamic acid, can effectively be catalyzed benzaldehyde and acetaldehyde reacts and generates cinnamic acid, excellent catalytic effect, and the yield of cinnamic acid is obtained by the reaction
Also it is higher.
Claims (2)
1. a kind of preparation method of alkalinity rosin polymer catalyst, which is characterized in that step is as follows：
（1）The synthesis of monomeric compound 1：
It is first added in levopimaric acid at 175-185 DEG C by polymerization inhibitor of hydroquinone, reaction 30 minutes or more, then
Acrylic acid is added in, at 230-240 DEG C, 3-5h is reacted, obtains rosin acrylic acid, then by rosin acrylic acid and acrylic acid hydroxyl second
Ester is raw material, back flow reaction 3.5-6h, synthon compound 1；
（2）The synthesis of monomeric compound 2：
2-aminopyridine is dissolved with dichloromethane, under ice bath, acryloyl chloride reaction 0.5-1 h is added in, adds acid binding agent, instead
After answering 10-20min, heating reflux reaction 4-5.5 h, synthon compound 2；
（3）The preparation of catalyst：
Using azo-bis-isobutyl cyanide as initiator, polyvinyl alcohol is dispersant, by azo-bis-isobutyl cyanide, polyvinyl alcohol and is dissolved with
The oil-dissolving solvent of monomeric compound 1 and monomeric compound 2 is reacted, and in the case where temperature is 65-70 DEG C, is reacted 2-4h, is made
Alkaline rosin polymer catalyst；
The step（1）The concrete operation step of the synthesis of monomeric compound 1 is：
According to weight ratio levopimaric acid：Hydroquinone is 165-175:Levopimaric acid and hydroquinone are placed in by 1 ratio
In reaction kettle, it is warming up to 175-185 DEG C, isomerization reaction 30 minutes or more after separating water, adds in acrylic acid, acrylic acid adds in
Amount is 0.2-0.4 times that levopimaric acid adds in quality, is warming up to 230-240 DEG C, reacts 3-5h, obtains rosin acrylic acid, take
Rosin acrylic acid is placed in reaction kettle, adds in the thionyl chloride of 95-100 times of rosin acrylic acid weight, heating reflux reaction 5-7 h
Afterwards, thionyl chloride excessive in reaction kettle is removed, rosin acrylic acid is added in and adds in the thiacyclohexane of 18-23 times of weight and propylene sea
Loose acid adds in the hydroxy-ethyl acrylate of 1-1.4 times of weight, after back flow reaction 3.5-6h, will obtain monomeric compound after purification of products
1；
The step（2）The concrete operation step of the synthesis of monomeric compound 2 is：
Quantitative 2-aminopyridine is dissolved in dichloromethane, under ice bath, adds in the propylene of 1-2 times of 2-aminopyridine weight
Acyl chlorides after reacting 0.5-1 h, adds in the acid binding agent of 4.8-5.5 times of 2-aminopyridine weight, after reacting 10-20min, heats back
Stream reaction 4-5.5 h, obtain reaction product；Monomeric compound 2 will be obtained after purification of products；The acid binding agent for organic base or
Person's inorganic base, including triethylamine, pyridine, sodium carbonate, potassium carbonate；
The step（3）The concrete operation step of the preparation of catalyst is：
By the reacting dose of polyvinyl alcohol, monomeric compound 1, monomeric compound 2 and azo-bis-isobutyl cyanide according to by weight, gather
Vinyl alcohol：Monomeric compound 1：Monomeric compound 2：Azo-bis-isobutyl cyanide is 0.1-0.5：1.5-7.5：1.1-6：0.1-0.5's
Ratio is reacted, and first polyvinyl alcohol is dissolved in the water, and then, adds in azo-bis-isobutyl cyanide and dissolved with monomeric compound
1 and the oil-dissolving solvent of monomeric compound 2,65-70 DEG C of temperature is heated with stirring to, after reacting 2-4h, is cooled to room temperature, product
After being filtered, washed and dried, alkaline rosin polymer catalyst is obtained；The oil-dissolving solvent include petroleum ether, hexamethylene,
Benzene, toluene and dimethylbenzene.
2. the preparation method of alkalinity rosin polymer catalyst as described in claim 1, which is characterized in that alkalinity pine obtained
Application of the fragrant polyalcohol catalyst in cinnamic acid is synthesized, the operation of concrete application are：Benzaldehyde in molar ratio：Acetaldehyde is 1：1-
1.2 ratio mixes benzaldehyde with acetaldehyde, and adds in the alkaline rosin polymer catalyst of benzaldehyde weight 4-6%, in room temperature
It is stirred to react 3-9 hours, product, yield 33%-67% is obtained after separation is distilled.
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| CN101319036A (en) * | 2008-06-18 | 2008-12-10 | 广西民族大学 | Colophony based functional polymer and preparation method thereof |
| CN103232349A (en) * | 2013-03-28 | 2013-08-07 | 中国林业科学研究院林产化学工业研究所 | Rosin or rosin derivative long chain flexible monomer preparation method |
| CN105013533A (en) * | 2015-07-13 | 2015-11-04 | 天津师范大学 | Cross-linked sulfonated poly-aromatic (sulfur) ether solid acid catalyst and preparation method and application thereof |
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| CN101319036A (en) * | 2008-06-18 | 2008-12-10 | 广西民族大学 | Colophony based functional polymer and preparation method thereof |
| CN103232349A (en) * | 2013-03-28 | 2013-08-07 | 中国林业科学研究院林产化学工业研究所 | Rosin or rosin derivative long chain flexible monomer preparation method |
| CN105013533A (en) * | 2015-07-13 | 2015-11-04 | 天津师范大学 | Cross-linked sulfonated poly-aromatic (sulfur) ether solid acid catalyst and preparation method and application thereof |
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Application publication date: 20160127 Assignee: GUANGXI DINGHONG RESIN CO.,LTD. Assignor: GUANGXI UNIVERSITY FOR NATIONALITIES Contract record no.: X2022450000427 Denomination of invention: Preparation and application of a basic rosin polymer catalyst Granted publication date: 20180706 License type: Exclusive License Record date: 20221227 |