CN106824267A - A kind of Suzuki coupling reactions palladium-carbon catalyst and preparation method thereof - Google Patents
A kind of Suzuki coupling reactions palladium-carbon catalyst and preparation method thereof Download PDFInfo
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- CN106824267A CN106824267A CN201710056692.5A CN201710056692A CN106824267A CN 106824267 A CN106824267 A CN 106824267A CN 201710056692 A CN201710056692 A CN 201710056692A CN 106824267 A CN106824267 A CN 106824267A
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- carbon catalyst
- suzuki coupling
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
- B01J2231/4227—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group with Y= Cl
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The present invention discloses a kind of preparation method of Suzuki coupling reactions palladium-carbon catalyst, comprises the following steps：Cocoanut active charcoal is boiled activation by S1 through 5% 10% dust technologies, and then deionized water is washed to neutrality, drying；S2 meterings are added in the alcoholic solution containing phosphorus part and are impregnated through the cocoanut active charcoal after step S1 treatment, and wherein dipping temperature control removes solvent afterwards at 50 60 DEG C, obtain loading the activated carbon of triphenylphosphine；The activated carbon of S3 load triphenylphosphines is beaten with the ammonia palladium of bicarbonate four with water, ethanol or ethylene glycol；S4 controls temperature at 80 100 DEG C, is passed through the 4h of hydrogen reducing 3, you can obtain palladium-carbon catalyst.Preparation method of the invention is selected and technology controlling and process by the material for optimizing, particularly wherein fit applications of phosphorus part so that its simple and reliable process, the palladium-carbon catalyst reactivity of preparation is high, selectivity is high, have the advantage of homogeneous heterogeneous catalysis concurrently, be easy to the recovery of follow-up heavy metal.
Description
Technical field
The invention belongs to loaded noble metal catalyst preparing technical field, and in particular to a kind of Suzuki coupling reactions are used
Palladium-carbon catalyst and preparation method thereof.
Background technology
Palladium-carbon catalyst is a kind of conventional hydrogenation catalyst and coupling catalyst, anti-in organic synthesis Suzuki couplings
Should, in Heck reactions and Sonogashira reactions using wider.For a long time, suzuki coupling reactions are matched somebody with somebody using homogeneous phosphorus
Body catalyst, though homogeneous catalyst, with higher active and selective, after use, noble metal cannot be reclaimed, and cause ring
Pollute and the wasting of resources in border.In recent years, in Suzuki coupling reactions, researcher begins to use load type palladium catalyst for example
Palladium carbon, as catalyst synthesis of coupling.But substrate varies, the need for single palladium carbon can not meet reaction, therefore, need
Palladium carbon is modified, to strengthen its activity.
Patent CN104689832A discloses a kind of preparation method of Suzuki coupling reactions with modified palladium carbon catalyst, should
Catalyst is made up of activated carbon and the palladium being carried on activated carbon and nickel, and wherein the weight/mass percentage composition of palladium is 5%~10%, nickel
Weight/mass percentage composition be 0.5%~3%.The palladium carbon catalyst preparation method is comprised the following steps：First, nano nickel is prepared molten
Glue；2nd, absorbent charcoal carrier is prepared；3rd, nickeliferous slurries are prepared；4th, palladium-containing solution is prepared；5th, palladium-containing solution is added drop-wise to nickeliferous
In slurries, filtered after insulation dipping, obtain filter cake；6th, reduction treatment is carried out, modified palladium carbon catalyst is obtained after washing.The palladium
Pd/carbon catalyst reactivity is high, selectivity high, but its preparation method technique is cumbersome, particularly heavy metal palladium in subsequent recovery not
Easily, energy consumption and pollution are larger.
The content of the invention
For the disadvantages described above or Improvement requirement of prior art, the invention provides a kind of Suzuki coupling reactions palladium carbon
Catalyst and preparation method thereof, wherein being selected and technology controlling and process by the material for optimizing, particularly wherein the cooperation of phosphorus part should
With so that its simple and reliable process, the palladium-carbon catalyst reactivity of preparation is high, selective high, and is subsequently easy to heavy metal
Recovery.
To achieve the above object, it is proposed, according to the invention, a kind of preparation side of Suzuki coupling reactions palladium-carbon catalyst is provided
Method, it is characterised in that comprise the following steps：
Cocoanut active charcoal is boiled activation by S1 through 5%-10% dust technologies, and then deionized water is washed to neutrality, drying；
S2 meterings are added in the alcoholic solution containing phosphorus part and are impregnated through the cocoanut active charcoal after step S1 treatment,
Wherein dipping temperature control removes solvent afterwards at 50-60 DEG C, obtains loading the activated carbon of triphenylphosphine；
The activated carbon of S3 load triphenylphosphines is beaten with the ammonia palladium of bicarbonate four with water, ethanol or ethylene glycol；
S4 controls temperature at 80-100 DEG C, is passed through hydrogen reducing 3-4h, you can obtain palladium-carbon catalyst.
In such scheme, cocoanut active charcoal boils activation through nitric acid, and by first loading phosphorus part, with the ammonia palladium of bicarbonate four
Phosphorus part therein and activated carbon can play support peptizaiton to palladium particle after being beaten, by controlling reduction temperature
Hydrogen reducing is carried out with the time, can be played with the effect of effective guarantee palladium activated centre.
Used as present invention further optimization, the Phosphine ligands have following structural formula, wherein R1, R2, R3 at least
Individual is phenyl or substituted benzene phenyl, and R1, R2, R3 can be with identical, can also be different.
Used as present invention further optimization, wherein phosphorus part is triphenyl phasphine or three (substituted-phenyl) phosphines, wherein on phenyl ring
Substitution base can be with identical, can also be different.
Used as present invention further optimization, the phosphorus part is triphenylphosphine, three (o-methyl-phenyl) phosphines, three (m- sulphurs
Acidic group phenyl) phosphine, diphenyl (2- hydroxy phenyls) phosphine, three (1,3,5- trimethylphenyls) phosphines or three (p-methylphenyl) phosphines.
Used as present invention further optimization, alcoholic solution used is methyl alcohol, ethanol, isopropanol or ethylene glycol.
It is another aspect of this invention to provide that providing a kind of Suzuki coupling reactions prepared using above-mentioned preparation method
Use palladium-carbon catalyst.
In general, by the contemplated above technical scheme of the present invention compared with prior art, with following beneficial effect
Really：
1) in preparation method of the invention, by the selection of load phosphorus part and specific phosphorus part in advance so that with carbon
Phosphorus part therein and activated carbon can play support peptizaiton to palladium particle after the ammonia palladium of sour hydrogen four is beaten, its process
Control reduction temperature and time carry out hydrogen reducing, can be played with the effect of effective guarantee palladium activated centre；
2) in preparation method of the invention, selected and technology controlling and process by the material for optimizing, particularly wherein phosphorus part
Fit applications so that its simple and reliable process, the palladium-carbon catalyst reactivity of preparation is high, selective high, has concurrently homogeneous non-equal
The advantage of phase catalyst, and subsequently it is easy to the recovery of heavy metal.
Specific embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, below in conjunction with specific embodiment, to this
Invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, not
For limiting the present invention.As long as additionally, technical characteristic involved in invention described below each implementation method that
Conflict is not constituted between this can be just mutually combined.
A kind of preparation method of Suzuki coupling reactions palladium-carbon catalyst of the embodiment of the present invention, its catalyst for preparing
The characteristics of having concurrently homogeneously and divide homogeneous catalyst.The preparation method is comprised the following steps that：
Cocoanut active charcoal is boiled activation by S1 through 5%-10% dust technologies, and then deionized water is washed to neutrality, drying；
S2 meterings are added in the alcoholic solution containing phosphorus part and are impregnated through the cocoanut active charcoal after step S1 treatment,
Wherein dipping temperature control removes solvent afterwards at 50-60 DEG C, obtains loading the activated carbon of triphenylphosphine；
S3 carries out the activated carbon for loading triphenylphosphine with the ammonia palladium of bicarbonate four with water, deionized water, ethanol or ethylene glycol
Mashing；
S4 controls temperature at 80-100 DEG C, is passed through hydrogen reducing 3-4h, you can obtain palladium-carbon catalyst.
Specifically, the detailed process of this preparation method is described in detail below in conjunction with specific embodiment.
Embodiment 1
1) cocoanut active charcoal 16g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) dry activated carbon is contributed to, in the methanol solution containing 2g triphenylphosphines, 50 DEG C of timings of impregnation one
Between, such as 3h removes solvent, obtains loading the activated carbon of triphenylphosphine；
3) activated carbon of the load triphenylphosphine that will be obtained is beaten with 2.46g bicarbonate tetramino palladium 300mL deionized waters
Slurry；
4) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Embodiment 2
1) cocoanut active charcoal 16g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) dry activated carbon is contributed to, in the methanol solution containing 2g tri- (o-methyl-phenyl) phosphine, 55 DEG C of dippings are anti-
3h is answered, solvent is removed, obtains loading the activated carbon of triphenylphosphine；
3) activated carbon of the load triphenylphosphine that will be obtained is beaten with 2.46g bicarbonate tetramino palladium 300mL water；
4) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Embodiment 3
1) cocoanut active charcoal 16g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) dry activated carbon is contributed to, in the methanol solution containing 2g tri- (m- sulfonic group phenyl) phosphine, 60 DEG C of dippings
Reaction 3h, removes solvent, obtains loading the activated carbon of triphenylphosphine；
3) activated carbon of the load triphenylphosphine that will be obtained is beaten with 2.46g bicarbonate tetramino palladium 300mL ethanol；
4) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Embodiment 4
1) cocoanut active charcoal 16g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) dry activated carbon is contributed to, in the methanol solution containing 2g diphenyl (2- hydroxy phenyls) phosphine, 50 DEG C of leachings
Stain reacts 3h, removes solvent, obtains loading the activated carbon of triphenylphosphine；
3) activated carbon of the load triphenylphosphine that will be obtained is beaten with 2.46g bicarbonate tetramino palladium 300mL ethylene glycol；
4) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Embodiment 5
1) cocoanut active charcoal 16g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) dry activated carbon is contributed to, in the methanol solution containing 2g tri- (1,3,5- trimethylphenyl) phosphine, 55 DEG C
Impregnation 3h, removes solvent, obtains loading the activated carbon of triphenylphosphine；
3) activated carbon of the load triphenylphosphine that will be obtained is beaten with 2.46g bicarbonate tetramino palladium 300mL water；
4) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Embodiment 6
1) cocoanut active charcoal 16g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) dry activated carbon is contributed to, in the methanol solution containing 2g tri- (p-methylphenyl) phosphine, 60 DEG C of impregnations
3h, removes solvent, obtains loading the activated carbon of triphenylphosphine；
3) activated carbon of the load triphenylphosphine that will be obtained is beaten with 2.46g bicarbonate tetramino palladium 300mL ethylene glycol；
4) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Comparative example 7
1) cocoanut active charcoal 19g is weighed, activation is boiled with 5%-10% nitric acid, filtering is washed to neutrality, drying to constant weight；
2) activated carbon and 2.46g bicarbonate tetramino palladiums are beaten with 300mL water；
3) 80-100 DEG C of temperature is controlled, hydrogen reducing 3-4h is passed through, palladium-carbon catalyst is obtained.
Performance evaluation is carried out to the catalyst that embodiment of the present invention 1-6 and comparative example 7 are obtained, equipped with bubbler, condensation
Pipe, there-necked flask in add 2mmol halogeno-benzenes and 2.2mmol substituted boracic acids, 4mmol alkali, and the catalysis containing palladium 0.01mol
Agent, DMF and water ratio are 1:9, vacuum, nitrogen displacement three times, 80 DEG C of reactions, liquid phase tracking is until substrate disappears substantially.
The coupling of naphthalene boronic acids and o-chloronitrobenzene
It should be noted that in the various embodiments described above, activated carbon is preferably cocoanut active charcoal in step S1, its quality is only
Above-mentioned numerical value is not limited to for illustrating, in technical scheme；Phosphorus in step S2 is also not necessarily limited to weight
Numerical value shown in embodiment, actually its be not limited to the quality proportioning of activated carbon involved specific in embodiment
Value, its can carry out according to the actual requirements it is specifically chosen, such as 1:2,1:1,2:1 or other suitable ratios.In addition, step S2
In preferably 50-60 DEG C of dipping temperature when being impregnated, dipping is actually not limited to 3h, actually activated carbon supported phosphorus part
Dipping effect it is relevant with activated carbon types, dipping temperature and time, in this programme by dipping temperature control at 50-60 DEG C,
Such as 50 DEG C, 55 DEG C or 60 DEG C, the actual control of dipping can cause that dipping effect is optimal in 2-4h, phosphorus is loaded on activated carbon and is matched somebody with somebody
The effect of body is best.
Bicarbonate tetramino palladium in step S3 is not limited to the quality in above-described embodiment, and it can be according to actual conditions
Carry out specifically chosen, it can according to the actual requirements be adjusted or select with the mass ratio of the activated carbon of load triphenylphosphine,
Concrete numerical value in above-described embodiment is not intended to limit the present invention.Wherein with the activated carbon of load triphenylphosphine mix and beat
The liquid of slurry is not limited to the type listed in above-described embodiment, for example can be water, deionized water, ethanol or ethylene glycol, its
Volume is also not necessarily limited to be 300ml that it can be carried out according to the amount of the activated carbon of load triphenylphosphine and bicarbonate tetramino palladium
It is specifically chosen.
In addition, in step S4, when carrying out hydrogen reducing, its reduction temperature is preferably controlled in 80-100 DEG C, such as can be
80 DEG C, 90 DEG C or 100 DEG C, the recovery time is preferably controlled in 3-4h, for example, can be 3h, 3.5h or 4h.By controlling reduction anti-
The time answered matches with temperature so that its activated carbon bicarbonate tetramino palladium that can fully adapt to load triphenylphosphine it is mixed
Liquid is closed, with optimal reduction reaction effect.
In a word, each group classifying type and parameter are only for preferably explaining technical scheme in above-described embodiment,
The more crucially core group therein of the technical scheme being not intended to limit the present invention, actually technical solution of the present invention
Divide and using the specific preparation technology of phosphorus part, it is hereby achieved that the palladium-carbon catalyst of function admirable.
As it will be easily appreciated by one skilled in the art that the foregoing is only presently preferred embodiments of the present invention, it is not used to
The limitation present invention, all any modification, equivalent and improvement made within the spirit and principles in the present invention etc., all should include
Within protection scope of the present invention.
Claims (6)
1. a kind of preparation method of Suzuki coupling reactions palladium-carbon catalyst, it is characterised in that comprise the following steps：
Cocoanut active charcoal is boiled activation by S1 through 5%-10% dust technologies, and then deionized water is washed to neutrality, drying；
S2 meterings are added in the alcoholic solution containing phosphorus part and are impregnated through the cocoanut active charcoal after step S1 treatment, wherein
Dipping temperature is controlled at 50-60 DEG C, and solvent is removed afterwards, obtains loading the activated carbon of triphenylphosphine；
The activated carbon of S3 load triphenylphosphines is beaten with the ammonia palladium of bicarbonate four with water, ethanol or ethylene glycol；
S4 controls temperature at 80-100 DEG C, is passed through hydrogen reducing 3-4h, you can obtain palladium-carbon catalyst.
2. the preparation method of a kind of Suzuki coupling reactions palladium-carbon catalyst according to claim 1, wherein, the phosphine
Part has a following structural formula, wherein R1, R2, R3 at least one be phenyl or substituted benzene phenyl, R1, R2, R3 can with identical,
Can also be different.
3. the preparation method of a kind of Suzuki coupling reactions palladium-carbon catalyst according to claim 1 and 2, wherein, institute
Phosphorus part is stated for triphenyl phasphine or three (substituted-phenyl) phosphines, wherein benzene ring substituents can be with identical, can also be different.
4. the preparation method of a kind of Suzuki coupling reactions palladium-carbon catalyst according to any one of claim 1 to 3,
Wherein, the phosphorus part is triphenylphosphine, three (o-methyl-phenyl) phosphines, three (m- sulfonic group phenyl) phosphines, diphenyl (2- hydroxyls
Phenyl) phosphine, three (1,3,5- trimethylphenyls) phosphines or three (p-methylphenyl) phosphines.
5. the preparation method of a kind of Suzuki coupling reactions palladium-carbon catalyst according to any one of claim 1 to 4,
Wherein, alcoholic solution used is methyl alcohol, ethanol, isopropanol or ethylene glycol.
6. the Suzuki coupling reaction palladiums that the preparation method any one of a kind of utilization claim 1 to 5 is prepared
C catalyst.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110180587A (en) * | 2019-06-28 | 2019-08-30 | 江西省汉高新材料有限公司 | The preparation method and applications of functionalized silicon nanometer sheet loaded palladium catalyst |
| CN110755992A (en) * | 2018-07-27 | 2020-02-07 | 中国石油化工股份有限公司 | Modified adsorbent and preparation method thereof |
| CN110756161A (en) * | 2018-07-27 | 2020-02-07 | 中国石油化工股份有限公司 | Process method for treating octanol waste gas pollution |
| CN114904585A (en) * | 2022-05-20 | 2022-08-16 | 浙江南郊化学有限公司 | Preparation method of palladium-carbon catalyst for Suzuki coupling reaction |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101941981A (en) * | 2009-07-03 | 2011-01-12 | 湖南华纳大药厂有限公司 | Catalyst composition and method for preparing faropenem sodium |
| CN105175217A (en) * | 2015-10-21 | 2015-12-23 | 山东盛华电子新材料有限公司 | Method for synthesizing polycyclic aromatic hydrocarbon by directly coupling Grignard reagent of halogenated compounds with halogenated compound by recyclable modified palladium on carbon |
| CN105237461A (en) * | 2015-10-21 | 2016-01-13 | 山东盛华电子新材料有限公司 | Method for utilizing recyclable modified palladium-charcoal to synthesize heterocyclic compound by directly coupling halogenated compound Grignard reagent to halogenated compound |
| CN105348037A (en) * | 2015-10-21 | 2016-02-24 | 山东盛华电子新材料有限公司 | Synthetic method of directly coupling aryl halide by aromatic hydrocarbon Grignard reagent in the presence of recycled modified palladium-charcoal |
-
2017
- 2017-01-25 CN CN201710056692.5A patent/CN106824267A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101941981A (en) * | 2009-07-03 | 2011-01-12 | 湖南华纳大药厂有限公司 | Catalyst composition and method for preparing faropenem sodium |
| CN105175217A (en) * | 2015-10-21 | 2015-12-23 | 山东盛华电子新材料有限公司 | Method for synthesizing polycyclic aromatic hydrocarbon by directly coupling Grignard reagent of halogenated compounds with halogenated compound by recyclable modified palladium on carbon |
| CN105237461A (en) * | 2015-10-21 | 2016-01-13 | 山东盛华电子新材料有限公司 | Method for utilizing recyclable modified palladium-charcoal to synthesize heterocyclic compound by directly coupling halogenated compound Grignard reagent to halogenated compound |
| CN105348037A (en) * | 2015-10-21 | 2016-02-24 | 山东盛华电子新材料有限公司 | Synthetic method of directly coupling aryl halide by aromatic hydrocarbon Grignard reagent in the presence of recycled modified palladium-charcoal |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110755992A (en) * | 2018-07-27 | 2020-02-07 | 中国石油化工股份有限公司 | Modified adsorbent and preparation method thereof |
| CN110756161A (en) * | 2018-07-27 | 2020-02-07 | 中国石油化工股份有限公司 | Process method for treating octanol waste gas pollution |
| CN110755992B (en) * | 2018-07-27 | 2022-04-08 | 中国石油化工股份有限公司 | Modified adsorbent and preparation method thereof |
| CN110756161B (en) * | 2018-07-27 | 2022-04-08 | 中国石油化工股份有限公司 | Process method for treating octanol waste gas pollution |
| CN110180587A (en) * | 2019-06-28 | 2019-08-30 | 江西省汉高新材料有限公司 | The preparation method and applications of functionalized silicon nanometer sheet loaded palladium catalyst |
| CN114904585A (en) * | 2022-05-20 | 2022-08-16 | 浙江南郊化学有限公司 | Preparation method of palladium-carbon catalyst for Suzuki coupling reaction |
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Application publication date: 20170613 |