CN107286006A - A kind of method that catalyzed alcoholysis lignin prepares Acetovanillone and acetosyringone - Google Patents
A kind of method that catalyzed alcoholysis lignin prepares Acetovanillone and acetosyringone Download PDFInfo
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- CN107286006A CN107286006A CN201710429859.8A CN201710429859A CN107286006A CN 107286006 A CN107286006 A CN 107286006A CN 201710429859 A CN201710429859 A CN 201710429859A CN 107286006 A CN107286006 A CN 107286006A
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- lignin
- acetovanillone
- acetosyringone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—Cobalt
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/83—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with rare earths or actinides
Abstract
The invention discloses a kind of method that catalyzed alcoholysis lignin prepares Acetovanillone and acetosyringone, this method is using lignin as raw material, the microwave alcoholysis in the alcohols solvent containing load type metal catalyst, through supercooling, filtering and washing, the product liquid based on Acetovanillone and acetosyringone is obtained, described load type metal catalyst is made up of activated centre Co and carrier；The present invention is improved by the method to conventional wooden element degraded, it is proposed that a kind of environment-friendly, cheap load type metal catalyst, under microwave heating condition, is realized lignin efficient degradation, is prepared two class compounds of higher yields：Acetovanillone and acetosyringone；This method reaction condition is gentle, the heat time is shorter, and reaction efficiency is higher.
Description
Technical field
Acetovanillone is prepared the present invention relates to the utilization technical field of lignin, more particularly to a kind of catalyzed alcoholysis lignin
With the method for acetosyringone.
Background technology
Now, the problems such as crisis of world energy sources consumption, environment are by severe contamination is of increasing concern.The mankind largely use
The fossil fuels such as coal, not only cause the situation that the energy faces exhaustion, its also serious pollution environment of waste gas waste water discharged.
Biomass energy as a kind of preferable emerging energy of development prospect, it be solar energy with chemical energy form be stored in plant can
The renewable sources of energy, are described as optimal regenerative resource.
Biomass is mainly made up of cellulose, hemicellulose and lignin.Lignin is natural organic polymer
Compound, is quantitatively only second to cellulose, estimates that the annual whole world can produce 150,000,000,000 tons of lignin by plant growth.It is used as wood
The accessory substance of material Hydrolysis Industry and paper industry, due to being not fully utilized, becomes environmental contaminants, seriously pollutes
Environment.Although so Liginon Resource very abundant, needs reasonable utilization badly.
Catalytic liquefaction lignin is because its reaction condition is relatively mild, energy consumption of reaction is relatively low and turns into lignin degradation
A kind of important method.Solvent and catalyst play an important role in lignin normal pressure catalytic liquefaction, can not only improve
Lignin conversion rate, can also heighten selectivity of product.
Chinese patent（CN 102295547 A）Oxidant and lignin are reacted in alkaline solution, reaction is anti-after terminating
Answer liquid it is acidified, extracting, concentration and again rectifying obtain Acetovanillone and acetosyringone, through gas chromatographic analysis understand its purity
Respectively 97.3% and 98.2%.Through investigation, it is also important that Acetovanillone and acetosyringone, which are not only widely used in perfume industry,
Organic synthesis raw material, medically available for synthetic drug, there is important value.The transition metal such as cobalt, copper, iron, zinc are urged
Agent is good oxidation reduction catalyst, therefore selects suitable load type metal catalyst, improves selectivity of product and production
Rate is most important.
The content of the invention
For above-mentioned problem, present invention aims at one kind is provided under Microwave-assisted firing, using alcohols to be molten
Agent, Acetovanillone and acetosyringone are prepared under load type metal catalyst effect.
In order to achieve the above object, the technical solution adopted by the present invention is as follows：A kind of catalyzed alcoholysis lignin prepares vanilla
The method of ethyl ketone and acetosyringone, described method is using lignin as raw material, in the alcohols containing load type metal catalyst
Microwave alcoholysis in solvent, through supercooling, filtering and washing obtain the product liquid based on Acetovanillone and acetosyringone,
Described load type metal catalyst is made up of activated centre Co and carrier.
Fe is introduced in load type metal catalyst of the present invention as auxiliary agent, described carrier is Al2O3、CeO2、
ZrO2, one kind in MgO.Fe can provide more electron holes as catalyst promoter, can lift Co catalysis
Activity, and then promote the fracture of lignin C-H or C-C key, improve target product yield.These four effect of acidity and basicity are not
Together, depolymerization effect can be contrasted.
Alcohols solvent of the present invention is isopropanol.Alcohols solvent is because its dissolving, hydrogen supply effect are more used in lignin
In degraded application.
The operating procedure for the method that catalyzed alcoholysis lignin of the present invention prepares Acetovanillone and acetosyringone is as follows：
1）Load type metal catalyst is prepared using infusion process；
2）The lignin and alcohols solvent of certain mass are weighed, retort mixing is added, then adds the support type of certain mass
Metallic catalyst is mixed, and retort is put into microwave reactor, is 100~180 DEG C in temperature, microwave power is 600 W bar
5~60 min are reacted under part；
3）Reaction is finished, and takes out retort natural cooling, product is filtered and washed with solvent, is obtained with Acetovanillone
With the product liquid based on acetosyringone.
Step 2 of the present invention）The mass ratio of middle lignin and load type metal catalyst is 1:0.3~1；Can from experimental result
Know：When the mass ratio of catalyst is in 0.3~1, curvilinear motion is presented in the yields of final products, thus the consumption of catalyst with
The yield of final products has a direct impact；When the consumption of catalyst is less than 0.3, final products are under yield can occur substantially
Drop, when catalyst amount is higher than 0.8, obvious decline also occurs for the yield of product.
In the present invention infusion process prepare load type metal catalyst method it is as follows：
1）Weigh Co (NO3)2·6H2O is put in beaker, solution is fully diluted to deionized water, incipient impregnation is in carrier
On, stirring at room temperature impregnates 24 h；
2）It is put into drying box 85°C is dried 12 h and obtained in catalyst precarsor, air atmosphere, to catalyst precarsor in Muffle furnace
Carry out 500°C, 4 h calcination；
3）By the catalyst after calcining 90 mL/min H21.5 h are reduced under atmosphere, reduction temperature is 550°C, is produced negative
Carry Co metallic catalyst.
Co load capacity is 5% in the load type metal catalyst of the present invention, and Co's and Fe rubs in load type metal catalyst
You are than being 1:0.3~0.8, it was found from experimental result：In the present invention in load type metal catalyst Co and Fe mol ratio 1:0.3
When, the yield of its final products reaches peak value, and when more than 0.3 or less than 0.3, the yield of final products can all decline.
The advantage of the invention is that：The present invention is improved by the method to conventional wooden element degraded, it is proposed that a kind of
Environment-friendly, cheap load type metal catalyst, under microwave heating condition, realizes lignin efficient degradation, prepares
Two class compounds of higher yields：Acetovanillone and acetosyringone；This method has that reaction condition is gentle, the heat time is shorter
With reaction efficiency it is higher the advantages of.
Brief description of the drawings
Fig. 1 efficiently prepares Acetovanillone and second for different carriers catalyst in 3-5 of the embodiment of the present invention to lignin alcoholysis
The influence of acyl syringone distribution；
Fig. 2 efficiently prepares Acetovanillone and acetyl cloves for Co/Fe mol ratios in 6-8 of the embodiment of the present invention to lignin alcoholysis
The influence of ketone distribution；
Fig. 3 efficiently prepares Acetovanillone and acetosyringone for catalyst amount in 9-11 of the embodiment of the present invention to lignin alcoholysis
The influence of distribution；
Fig. 4 efficiently prepares Acetovanillone and acetosyringone for reaction temperature in 12-16 of the embodiment of the present invention to lignin alcoholysis
The influence of distribution；
Fig. 5 efficiently prepares Acetovanillone and acetosyringone for the reaction time in 17-20 of the embodiment of the present invention to lignin alcoholysis
The influence of distribution.
Embodiment
The present invention is described in further detail with embodiment for explanation below in conjunction with the accompanying drawings.
Embodiment 1：Weigh 1 g lignin, the mixing of 16 mL isopropanols and add retort, retort is put into microwave anti-
Device is answered, setting microwave power is 600 W, and 30 min are reacted under the conditions of certain 120 °C of reaction temperature.Reaction is finished, and is taken out
Counteracting tank, natural cooling.Product is filtered and cleaned with solvent isopropanol, the product liquid obtained after filtering is unified
20 mL, liquid to be detected product are dissolved to isopropanol.
Embodiment 2
A. 2.47 g Co (NO are weighed3)2·6H2O is placed in beaker, and solution, incipient impregnation are fully diluted to deionized water
In 10 g Al2O3On carrier, stirring at room temperature impregnates 24 h.It is then placed in drying box 85°C is dried 12 h and obtained before catalyst
In body, air atmosphere, 500 are carried out to catalyst precarsor in Muffle furnace°C, 4 h calcination.Finally by the catalyst after calcining
In 90 mL/min H21.5 h are reduced under atmosphere, reduction temperature is 550°C, you can obtain the Co/Al of catalyst 5%2O3。
B. 1 g lignin, the mixing of 16 mL isopropanols is weighed to add retort, and add 0.5 g catalyst 5%
Co/Al2O3It is mixed together in retort, retort is put into microwave reactor, setting microwave power is 600 W, certain
30 min are reacted under the conditions of 120 °C of reaction temperature.Reaction is finished, and takes out counteracting tank, natural cooling.Product is filtered simultaneously
And cleaned with solvent isopropanol, the product liquid obtained after filtering unification is dissolved to 20 mL, liquid to be detected production with isopropanol
Thing.
Embodiment 3 ~ 5
a. 5% Co/ZrO2、5% Co/CeO2, 5% Co/MgO catalyst preparation process use a steps in embodiment 2, it is different
Be respectively use different carrier ZrO2、CeO2Catalyst is prepared with MgO.
B. lignin uses the b step in embodiment 2 with degradation step of the catalyst in isopropanol solvent, different
It is that the catalyst type added is 5% Co/ZrO respectively2、5% Co/CeO2、5% Co/MgO。
Product liquid uses GC/MS qualitative detections, directly obtains two kinds of higher products of yield in product liquid（Acetovanillone
And acetosyringone）Peak area relation.Different catalysts are shown in Fig. 1 to the influence result that lignin alcoholysis product is distributed.
Embodiment 6
A. 2.47 g Co (NO are weighed3)2·6H2O is placed in beaker, then weighs 1.80 g Fe (NO3)3·9H2O places beaker
In, solution is fully diluted to deionized water, incipient impregnation is in 10 g Al2O3On carrier, stirring at room temperature impregnates 24 h.
It is then placed in drying box 85°C is dried 12 h and obtained in catalyst precarsor, air atmosphere, and catalyst precarsor is entered in Muffle furnace
Row 500°C, 4 h calcination.Finally by the catalyst after calcining 90 mL/min H21.5 h, reduction temperature are reduced under atmosphere
Spend for 550°C, you can obtain Co-Fe/Al2O3Bimetallic catalyst, wherein Co load capacity are that 5%, Co/Fe mol ratios are 1:
0.5。
B. 1 g lignin, the mixing of 16 mL isopropanols is weighed to add retort, and add 0.5 g bimetallic catalytic
Agent Co-Fe/Al2O3It is mixed together in retort, retort is put into microwave reactor, setting microwave power is 600 W,
30 min are reacted under the conditions of certain 120 °C of reaction temperature.Reaction is finished, and takes out counteracting tank, natural cooling.Product was carried out
Filter and cleaned with solvent isopropanol, the product liquid obtained after filtering unification is dissolved to 20 mL, liquid to be detected with isopropanol
Body product.
Embodiment 7 ~ 8：
A. Co load capacity is that 5%, Co/Fe mol ratios are 1:0.3、1:0.8 bimetallic catalyst Co-Fe/Al2O3Prepared
A steps in Cheng Caiyong embodiments 6, the difference is that weighing 1.08 g, 2.89 g Fe (NO respectively3)3·9H2O and 2.47 g Co
(NO3)2·6H2O salting liquids are mixed with catalyst.
B. lignin uses the b step in embodiment 2 with degradation step of the catalyst in isopropanol solvent, different
It is that the catalyst type added is that Co load capacity is that 5%, Co/Fe mol ratios are 1 respectively:0.3、1:0.8 bimetallic catalyst
Co-Fe/Al2O3。
Product liquid uses GC/MS qualitative detections, directly obtains two kinds of higher products of yield in product liquid（Acetovanillone
And acetosyringone）Peak area relation.Different catalysts are shown in Fig. 2 to the influence result that lignin alcoholysis product is distributed.
Embodiment 9：1 g lignin, the mixing of 16 mL isopropanols is weighed to add retort, and add Co load capacity：5%,
Co/Fe mol ratios：1:0.3 bimetallic catalyst Co-Fe/Al2O3It is mixed together in retort, catalyst amount is
0.3g.Retort is put into microwave reactor, setting microwave power is 600 W, anti-under the conditions of certain 120 °C of reaction temperature
Answer 30 min.Reaction is finished, and takes out counteracting tank, natural cooling.Product is filtered and cleaned with solvent isopropanol, incited somebody to action
The product liquid unification obtained after filter is dissolved to 20 mL, liquid to be detected product with isopropanol.
Embodiment 10 ~ 11：Lignin uses the step in embodiment 9 with degradation step of the catalyst in isopropanol solvent
Suddenly, the consumption of the catalyst added unlike is respectively 0.8 g and 1 g.
Product liquid uses GC/MS qualitative detections, directly obtains two kinds of higher products of yield in product liquid（Acetovanillone
And acetosyringone）Peak area relation.Different catalysts are shown in Fig. 3 to the influence result that lignin alcoholysis product is distributed.
Embodiment 12：1 g lignin, the mixing of 16 mL isopropanols is weighed to add retort, and add Co load capacity：5%,
Co/Fe mol ratios：1:0.3 bimetallic catalyst Co-Fe/Al2O3It is mixed together in retort, catalyst amount is 0.8
g.Retort is put into microwave reactor, setting microwave power is 600 W, and 30 are reacted under the conditions of certain 100 °C of reaction temperature
min.Reaction is finished, and takes out counteracting tank, natural cooling.Product is filtered and cleaned with solvent isopropanol, after filtering
Obtained product liquid unification is dissolved to 20 mL, liquid to be detected product with isopropanol.
Embodiment 13 ~ 16：Lignin uses the step in embodiment 12 with degradation step of the catalyst in isopropanol solvent
Suddenly, reaction temperature unlike is respectively 120 °C, 140 °C, 160 °C, 170 °C.
Product liquid uses GC/MS qualitative detections, directly obtains two kinds of higher products of yield in product liquid（Acetovanillone
And acetosyringone）Peak area relation.Different catalysts are shown in Fig. 4 to the influence result that lignin alcoholysis product is distributed.
Embodiment 17：1 g lignin, the mixing of 16 mL isopropanols is weighed to add retort, and add Co load capacity：5%,
Co/Fe mol ratios：1:0.3 bimetallic catalyst Co-Fe/Al2O3It is mixed together in retort, catalyst amount is 0.8
g.Retort is put into microwave reactor, setting microwave power is 600 W, and 5 are reacted under the conditions of certain 140 °C of reaction temperature
min.Reaction is finished, and takes out counteracting tank, natural cooling.Product is filtered and cleaned with solvent isopropanol, after filtering
Obtained product liquid unification is dissolved to 20 mL, liquid to be detected product with isopropanol.
Embodiment 18 ~ 20：Lignin uses the step in embodiment 17 with degradation step of the catalyst in isopropanol solvent
Suddenly, the reaction time unlike is respectively 15 min, 45 min, 60 min.
Product liquid uses GC/MS qualitative detections, directly obtains two kinds of higher products of yield in product liquid（Acetovanillone
And acetosyringone）Peak area relation.Different catalysts are shown in Fig. 5 to the influence result that lignin alcoholysis product is distributed.
It should be noted that it is above-mentioned be only presently preferred embodiments of the present invention, not for limit the present invention protection model
Enclose, any combination or equivalents made on the basis of above-described embodiment belong to protection scope of the present invention.
Claims (7)
1. a kind of method that catalyzed alcoholysis lignin prepares Acetovanillone and acetosyringone, it is characterised in that described method
Using lignin as raw material, the microwave alcoholysis in the alcohols solvent containing load type metal catalyst, through supercooling, is filtered and washed
Wash, obtain the product liquid based on Acetovanillone and acetosyringone, described load type metal catalyst is by activated centre
Co and carrier are constituted.
2. the method that catalyzed alcoholysis lignin as claimed in claim 1 prepares Acetovanillone and acetosyringone, its feature exists
In introducing Fe is as auxiliary agent in described load type metal catalyst, and described carrier is Al2O3、CeO2、ZrO2, in MgO
It is a kind of.
3. the method that catalyzed alcoholysis lignin as claimed in claim 1 prepares Acetovanillone and acetosyringone, its feature exists
In described alcohols solvent is isopropanol.
4. the method that the catalyzed alcoholysis lignin as described in claim 1 or 2 or 3 prepares Acetovanillone and acetosyringone, its
It is characterised by, the operating procedure of described method is as follows：
1）Load type metal catalyst is prepared using infusion process；
2）The lignin and alcohols solvent of certain mass are weighed, retort mixing is added, then adds the support type of certain mass
Metallic catalyst is mixed, and retort is put into microwave reactor, is 100~180 DEG C in temperature, microwave power is 600 W bar
5~60 min are reacted under part；
3）Reaction is finished, and takes out retort natural cooling, product is filtered and washed with solvent, is obtained with Acetovanillone
With the product liquid based on acetosyringone.
5. the method that catalyzed alcoholysis lignin as claimed in claim 1 prepares Acetovanillone and acetosyringone, its feature exists
In described step 2）The mass ratio of middle lignin and load type metal catalyst is 1:0.3~1.
6. the method that catalyzed alcoholysis lignin as claimed in claim 2 prepares Acetovanillone and acetosyringone, its feature exists
In the mol ratio that Co load capacity is Co and Fe in 5%, load type metal catalyst in described load type metal catalyst is
1:0.3~0.8.
7. the method that catalyzed alcoholysis lignin as claimed in claim 4 prepares Acetovanillone and acetosyringone, its feature exists
In described step 1）The method that middle infusion process prepares load type metal catalyst is as follows：
1）Weigh Co (NO3)2·6H2O is put in beaker, solution is fully diluted to deionized water, incipient impregnation is in carrier
On, stirring at room temperature impregnates 24 h；
2）It is put into drying box 85°C is dried 12 h and obtained in catalyst precarsor, air atmosphere, to catalyst precarsor in Muffle furnace
Carry out 500°C, 4 h calcination；
3）By the catalyst after calcining 90 mL/min H21.5 h are reduced under atmosphere, reduction temperature is 550°C, is produced negative
Carry Co metallic catalyst.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824497A (en) * | 2019-03-06 | 2019-05-31 | 华南理工大学 | A kind of method that microwave cooperating catalysis of metalloporphyrin oxidative degradation alkali lignin prepares single benzene ring compound |
| CN110639604A (en) * | 2019-09-09 | 2020-01-03 | 华南理工大学 | Black liquor lignin hydrogenolysis catalyst and preparation method and application thereof |
| CN111302910A (en) * | 2020-03-13 | 2020-06-19 | 中国科学院广州能源研究所 | Method for producing acetophenone and acetic acid by biomass directional catalysis |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875343A (en) * | 2012-10-31 | 2013-01-16 | 南京林业大学 | Method for preparing aromatic aldehyde compound by catalyzing and degrading lignin with loaded solid acid |
| CN103508857A (en) * | 2012-06-29 | 2014-01-15 | 中国科学院大连化学物理研究所 | Method for depolymerizing lignin into aromatic compounds under conditions of no additional hydrogen |
| CN103724189A (en) * | 2013-10-10 | 2014-04-16 | 华南理工大学 | Method for preparing monophenol compound by liquefying and degrading lignin through microwave concerted catalysis |
| CN105503540A (en) * | 2014-09-24 | 2016-04-20 | 中国科学院大连化学物理研究所 | Method for preparation of benzene ring phenol compound from alkali lignin |
| CN106565435A (en) * | 2016-10-27 | 2017-04-19 | 华南理工大学 | Method of selectively preparing aromatic aldehydes and aromatic methyl esters by degrading lignin with microwave assistance |
-
2017
- 2017-06-09 CN CN201710429859.8A patent/CN107286006B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103508857A (en) * | 2012-06-29 | 2014-01-15 | 中国科学院大连化学物理研究所 | Method for depolymerizing lignin into aromatic compounds under conditions of no additional hydrogen |
| CN102875343A (en) * | 2012-10-31 | 2013-01-16 | 南京林业大学 | Method for preparing aromatic aldehyde compound by catalyzing and degrading lignin with loaded solid acid |
| CN103724189A (en) * | 2013-10-10 | 2014-04-16 | 华南理工大学 | Method for preparing monophenol compound by liquefying and degrading lignin through microwave concerted catalysis |
| CN105503540A (en) * | 2014-09-24 | 2016-04-20 | 中国科学院大连化学物理研究所 | Method for preparation of benzene ring phenol compound from alkali lignin |
| CN106565435A (en) * | 2016-10-27 | 2017-04-19 | 华南理工大学 | Method of selectively preparing aromatic aldehydes and aromatic methyl esters by degrading lignin with microwave assistance |
Non-Patent Citations (4)
| Title |
|---|
| JECHAN L. ET AL: ""Stabilizing cobalt catalysts for aqueous-phase reactions by strong metal-support interaction"", 《JOURNAL OF CATALYSIS》 * |
| 储伟: "《催化剂工程》", 30 September 2006, 四川大学出版社 * |
| 刘娜娜等: ""微波辅助木质素醇解制备芳香化合物"", 《东南大学学报（自然科学版）》 * |
| 周强等: ""微波辅助木质素催化酸解机理研究"", 《太阳能学报》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824497A (en) * | 2019-03-06 | 2019-05-31 | 华南理工大学 | A kind of method that microwave cooperating catalysis of metalloporphyrin oxidative degradation alkali lignin prepares single benzene ring compound |
| CN110639604A (en) * | 2019-09-09 | 2020-01-03 | 华南理工大学 | Black liquor lignin hydrogenolysis catalyst and preparation method and application thereof |
| CN110639604B (en) * | 2019-09-09 | 2022-04-22 | 华南理工大学 | Black liquor lignin hydrogenolysis catalyst and preparation method and application thereof |
| CN111302910A (en) * | 2020-03-13 | 2020-06-19 | 中国科学院广州能源研究所 | Method for producing acetophenone and acetic acid by biomass directional catalysis |
| CN111302910B (en) * | 2020-03-13 | 2023-01-13 | 中国科学院广州能源研究所 | Method for producing acetophenone and acetic acid by biomass directional catalysis |
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