CN107008329A - Partial hydrogenation prepares method and the application of the copper nickel-base catalyst of high-purity oleic acid - Google Patents
Partial hydrogenation prepares method and the application of the copper nickel-base catalyst of high-purity oleic acid Download PDFInfo
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- CN107008329A CN107008329A CN201710222541.2A CN201710222541A CN107008329A CN 107008329 A CN107008329 A CN 107008329A CN 201710222541 A CN201710222541 A CN 201710222541A CN 107008329 A CN107008329 A CN 107008329A
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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
- B01J23/755—Nickel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The preparation method and application of the copper nickel-base catalyst of high-purity oleic acid, the preparation process comprising catalyst are prepared the invention discloses a kind of partial hydrogenation：Add Cu (NO3)2With Ni (NO3)2, stir and ammoniacal liquor be added dropwise to solution to suitable pH, add a certain amount of SiO2Continue to stir a period of time, through aging, filtering, washing, vacuum drying with obtaining copper nickel-base catalyst through hydrogen reducing again after roasting, and wrapped up with fixed oil, then industrial oleic acid and copper nickel-base catalyst are added in reactor, hydrogenation products are obtained after reacted, product is filtered, gained filtrate produces high-purity oleic acid by distillation.The catalyst has catalytic activity high and the good characteristic of selectivity, partial hydrogenation is carried out using this catalyst and prepares high-purity elaidin reaction flow simply, course of reaction is gentle, and product purity is high, cost is lower in manufacturing process, it is expected to the cleaning procedure route as great competitiveness.
Description
Technical field
The preparation method and the catalyst of copper-nickel-base catalyst of high-purity oleic acid are prepared the present invention relates to a kind of partial hydrogenation
Application, belong to correlative technology field prepared by high-purity oleic acid.
Background technology
Oleic acid is a kind of important natural products, is primarily present in animal and plant body grease, and its fine chemical product is extensive
Applied to fields such as chemical industry, medicine, food.But the purity of general industry oleic acid is less than 50%, and complicated component, causes oleic acid
Using being very limited, when oleic acid content reaches 70% above is can be referred to as high-purity oleic acid.
High-purity oleic acid is the liquid of colorless and odorless, is important fine chemicals raw material, and its product safety is non-stimulated, stably
Property is good, therefore, using it by the chemical products that raw material is developed and is generated, with hypotoxicity, be readily biodegradable, human body compatibility
And the features such as good environmental adaptability.In recent years, with the fast development and the improvement of people's living standards of China's economy, society is right
Food, light industrial goods and chemical products propose higher requirement in terms of application characteristic and performance, for example, nutrition is special
Property, security and biological degradability etc., extract obtained biological active matter from the oleic acid of high-purity and its byproduct of processing
Matter and using the oleic acid of high-purity by the product that raw material is developed and is produced, can preferably meet these demands.Therefore, it is high-purity
Oleic acid market demand gradually increases, while having attracted more researchers and enterpriser to bound oneself to it, it is intended to explore one kind
Efficiently, inexpensive high-purity oleic acid preparation method.
Usually, impurity main in industrial oleic acid is linoleic acid plus linolenic acid, and according to the characteristics of partial hydrogenation, industry
The partial hydrogenation of each material substantially divides three phases in oleic acid：(1) the preferential hydrogenating reduction of leukotrienes is linoleic acid, (2) linoleic acid
Hydrogenating reduction is oleic acid, and (3) oleic acid hydrogenating reduction is stearic acid, but under certain conditions, can be reduction reaction control the
(2) stage, the purity of oleic acid is only improved, and stearic content reaches the effect for preparing high-purity oleic acid without substantially increasing.
Traditional oil hydrogenation catalyst more select import nickel-base catalyst, but in view of the high activity of nickel-base catalyst and
The characteristics of low selectivity, the limit hydrogenation of grease is generally used for, is not suitable for the field of partial hydrogenation.In recent years, it is copper-based to urge
Agent research turns into focus, and its catalyst has a high selectivity and the characteristics of low activity, can also generate a certain amount of antiform oleic acid,
Have a strong impact on the quality and performance of high-purity oleic acid product.Therefore, it is necessary to develop a kind of portion with high activity and high selectivity
Divide Hydrogenation for the catalyst and preparation method of high-purity oleic acid.
The content of the invention
To solve the deficiencies in the prior art, it is an object of the invention to provide a kind of catalytic activity is high, the good copper of selectivity-
The preparation method of nickel-base catalyst and using application of the catalyst member Hydrogenation for high-purity oleic acid.
In order to realize above-mentioned target, the present invention is adopted the following technical scheme that：
The method that partial hydrogenation prepares copper-nickel-base catalyst of high-purity oleic acid, comprises the following steps：
S1, the addition Cu (NO in reaction vessel3)2With Ni (NO3)2Mixed solution, ammoniacal liquor is slowly added dropwise and stirs, adjust
The pH value of whole mixed solution is 8.0~10.0, is continuously stirred at room temperature, obtains suspension；During ammoniacal liquor is added dropwise, just
When starting to be added dropwise, precipitate metal hydroxides are initially formed, with the increase of ammoniacal liquor, when pH reaches setting range, precipitation disappears,
Metal ion and ammonium ion formation complex compound, so form suspension.
S2, pretreated SiO is added into suspension2, continue to stir 10~60min, then suspension is placed in into frozen water
- 5~5 DEG C are cooled in mixture, a certain amount of deionized water is slowly dropped in suspension, occurs hydrolysis, is continued
Stirring terminates to hydrolysis, and suspension is filtered by vacuum, and is then repeatedly washed with deionized colourless to cleaning solution, obtains
Copper-nickel hydroxide solid mixture Cu (OH)2-Ni(OH)2@SiO2；It should be noted that the SiO in the present invention2It is conduct
Carrier, the implication representated by@is load, as addition SiO2After carrier, complex compound is adsorbed in SiO2Carrier, is now added dropwise deionization
Water, can hydrolyze complex compound, form metal hydroxides, be adsorbed in SiO2On carrier.
S3, by solid mixture Cu (OH)2-Ni(OH)2@SiO2It is put into vacuum drying chamber and dries, is taken out after drying, then
Muffle kiln roasting is put into, copper-nickel oxide mixture C uO-NiO SiO are obtained2；
S4, by copper-nickel oxide mixture C uO-NiO@SiO2It is placed in tube furnace and carries out reducing instead under hydrogen environment
Should, obtain copper-nickel-base catalyst Cu-Ni@SiO2, then catalyst is wrapped in fixed oil.
Preferably, in abovementioned steps S1, Cu (NO3)2Solution concentration be 0.1~2.0mol/L, Ni (NO3)2Solution concentration
For 0.1~2.0mol/L, Cu (NO3)2With Ni (NO3)2Mol ratio be 100:1~600:1.
It is highly preferred that rotating speed is 390rpm in abovementioned steps S1, rotating speed is 480rpm in step S2.
More preferably, in abovementioned steps S2, SiO2Preprocess method be：Use the preceding drying process in 100 DEG C of baking ovens
10h, the volume of deionized water is 200~600mL, and time for adding should be 1~5h.
It is further preferred that in abovementioned steps S3, vacuum drying chamber temperature is 80~150 DEG C, drying time is 8~24h.
It is further preferred that in abovementioned steps S3, muffle furnace is 200~600 DEG C, roasting time is 1~6h.
Still further preferably, in abovementioned steps S4, hydrogen reducing temperature be 150~400 DEG C, heating rate be 5 DEG C/
Min, soaking time is 1~4h, is finally cooled to room temperature.
In addition, the present invention also disclosed the method that partial hydrogenation prepares high-purity oleic acid, step is as follows：Industrial oleic acid is added
In reactor, obtained copper-nickel-base catalyst before adding, in the case where reaction temperature is 135~195 DEG C, logical hydrogen makes reaction
Pressure is 0.5~1.3Mpa in kettle, reacts 1~3h under the conditions of stir speed (S.S.) is 200~500rpm, obtains hydrogenation products；It is right
Hydrogenation products are filtered, and continue to recycle after the solid catalyst roasting reduction treatment filtered out, gained filtrate is carried out
High-purity oleic acid is produced after distillation.
Preferably, the consumption of foregoing copper-nickel-base catalyst is the 0.5~2.5% of industrial oleic acid gross mass.
It is highly preferred that foregoing distillation mode is vacuum distillation.
The present invention is advantageous in that：The Cu-Ni@SiO that the preparation method of the present invention is obtained2There is catalyst catalysis to live
Property the high and good characteristic of selectivity, using Cu-Ni@SiO2The reaction process that catalyst partial hydrogenation prepares oleic acid is simple,
Course of reaction is gentle, and product purity is high, C18 in oleic acid:1 content reaches more than 70%, is a kind of high-purity oleic acid of high-quality, and this
It is lower that the method for invention prepares cost, it is expected to the cleaning procedure route as great competitiveness.
Embodiment
Make specific introduce to the present invention below in conjunction with specific embodiment.
Without specified otherwise in the present invention, all raw materials are purchased in market.
Embodiment 1
The partial hydrogenation of the present embodiment prepares copper-nickel-base catalyst of high-purity oleic acid, and specific preparation process is as follows：
S1, measure 24mL concentration be 0.25mol/L Cu (NO3)2It is 0.5mol/L Ni (NO with 0.04mL concentration3)2,
Pour at room temperature in beaker mix, with pH meter measure mixed solution pH value, while be slowly added dropwise ammonia spirit and stir make it is molten
Liquid pH value is 8.0, and rotating speed is maintained at 390rpm, obtains suspension.
S2, pretreated 4g SiO are added into suspension2, adjustment rotating speed is that 480rpm continues to stir 10~60min,
Suspension is placed in mixture of ice and water again and is cooled to 0 DEG C, 300mL deionized waters are slowly dropped to suspension in 3.5h
In, occur hydrolysis, continue to stir and terminate to hydrolysis, suspension is filtered by vacuum, is then repeatedly washed with deionized water
Wash colourless to cleaning solution, obtain copper-nickel hydroxide solid mixture Cu (OH)2-Ni(OH)2@SiO2；In this step, SiO2
Preprocess method be：Use the preceding drying process 10h in 100 DEG C of baking ovens.
S3, by solid mixture Cu (OH)2-Ni(OH)2@SiO2It is put into vacuum drying chamber and dries, 110 DEG C of drying process
12h, takes out, places into 400 DEG C of Muffle kiln roasting 3h, obtain copper-nickel oxide mixture C uO-NiO SiO2。
S4, by copper-nickel oxide mixture C uO-NiO@SiO2It is placed in tube furnace and carries out reducing instead under hydrogen environment
Should, temperature is adjusted to 250 DEG C, and heating rate is 5 DEG C/min, and soaking time is 2h, is cooled to room temperature, obtains copper-nickel-base catalyst
Cu-Ni@SiO2, then catalyst is wrapped in fixed oil.
Wherein, fixed oil parcel catalyst can prevent catalyst from occurring oxidation reaction, and implementation is substantially：Will hardening
Mixed after oil fusing with catalyst, cooling.Specific packaging method referring to the applicant earlier application
201620402788.3, therefore do not repeated in the application.
Embodiment 2- embodiments 5
The operating procedure of embodiment 2- embodiments 5 is identical with embodiment 1, and difference is the parameter in each step, tool
Body refers to table 1.
The embodiment 1-5 of table 1 parameter and experiment condition list
Embodiment 6
The present embodiment is the application of copper-nickel-base catalyst, specially using copper-nickel-base catalyst system made from embodiment 1
Standby high-purity oleic acid, step is as follows：
60g industrial oleic acids are added in reactor, copper-nickel-base catalyst as made from embodiment 1, catalyst matter is added
Measure as the 2% of industrial oleic acid gross mass, be that at 165 DEG C, logical hydrogen makes reacting kettle inner pressure be 0.8Mpa, is stirring in reaction temperature
Speed is mixed to react 2h under the conditions of 300rpm, hydrogenation products are obtained；Hydrogenation products are filtered, the solid catalyst warp filtered out
Continue to recycle after roasting reduction processing, to gained filtrate through vacuum distillation, collect low boiler cut, as high-purity oleic acid.
Embodiment 7
The present embodiment is the application of copper-nickel-base catalyst, specially using copper-nickel-base catalyst system made from embodiment 2
Standby high-purity oleic acid, step is as follows：
60g industrial oleic acids are added in reactor, copper-nickel-base catalyst as made from embodiment 2, catalyst matter is added
Measure as the 0.5% of industrial oleic acid gross mass, be that at 135 DEG C, logical hydrogen makes reacting kettle inner pressure be 0.8Mpa in reaction temperature,
Stir speed (S.S.) obtains hydrogenation products to react 1h under the conditions of 500rpm；Hydrogenation products are filtered, the solid catalyst filtered out
Continue to recycle after roasting reduction treatment, to gained filtrate through vacuum distillation, collect low boiler cut, as high-purity oil
Acid.
Embodiment 8
The present embodiment is the application of copper-nickel-base catalyst, specially using copper-nickel-base catalyst system made from embodiment 3
Standby high-purity oleic acid, step is as follows：
60g industrial oleic acids are added in reactor, copper-nickel-base catalyst as made from embodiment 3, catalyst matter is added
Measure as the 2.5% of industrial oleic acid gross mass, be that at 135 DEG C, logical hydrogen makes reacting kettle inner pressure be 0.5Mpa in reaction temperature,
Stir speed (S.S.) obtains hydrogenation products to react 3h under the conditions of 200rpm；Hydrogenation products are filtered, the solid catalyst filtered out
Continue to recycle after roasting reduction treatment, to gained filtrate through vacuum distillation, collect low boiler cut, as high-purity oil
Acid.
Embodiment 9
The present embodiment is the application of copper-nickel-base catalyst, specially using copper-nickel-base catalyst system made from embodiment 4
Standby high-purity oleic acid, step is as follows：
60g industrial oleic acids are added in reactor, copper-nickel-base catalyst as made from embodiment 4, catalyst matter is added
Measure as the 2% of industrial oleic acid gross mass, be that at 195 DEG C, logical hydrogen makes reacting kettle inner pressure be 1.3Mpa, is stirring in reaction temperature
Speed is mixed to react 3h under the conditions of 500rpm, hydrogenation products are obtained；Hydrogenation products are filtered, the solid catalyst warp filtered out
Continue to recycle after roasting reduction processing, to gained filtrate through vacuum distillation, collect low boiler cut, as high-purity oleic acid.
Embodiment 10
The present embodiment is the application of copper-nickel-base catalyst, specially using copper-nickel-base catalyst system made from embodiment 5
Standby high-purity oleic acid, step is as follows：
60g industrial oleic acids are added in reactor, copper-nickel-base catalyst as made from embodiment 5, catalyst matter is added
Measure as the 1% of industrial oleic acid gross mass, be that at 135 DEG C, logical hydrogen makes reacting kettle inner pressure be 0.8Mpa, is stirring in reaction temperature
Speed is mixed to react 2h under the conditions of 300rpm, hydrogenation products are obtained；Hydrogenation products are filtered, the solid catalyst warp filtered out
Continue to recycle after roasting reduction processing, to gained filtrate through vacuum distillation, collect low boiler cut, as high-purity oleic acid.
In order to preferably illustrate obtained Cu-Ni@SiO of the invention2Effect of the catalyst in high-purity oleic acid preparation process,
Examination index is generally turned to aliphatic acid composition change, show that copper-nickel-base catalyst shown in table 2 prepares high-purity oleic acid by experiment
Catalytic performance table.
2 bronze medals of table-nickel-base catalyst prepares the catalytic performance of high-purity oleic acid
aThe modified Cu-Ni@SiO of parcel2Contain a small amount of palmitic acid in the fixed oil of catalyst, therefore compare palm fibre in raw material, product
The increase of palmitic acid acid content.
From table 2 we can see that：High-purity oleic acid prepared by embodiment 6-10 and aliphatic acid in industrial oleic acid raw material
C16:0、C18:0、C18:1、C18:2 and C18:3 content all has differences, wherein C18:1 be evaluate oleic acid high-quality whether
Important criterion, general C18:Oleic acid of 1 content more than 70% is referred to as C18 in high-purity oleic acid, industrial oleic acid raw material:1 content
For 36.6%, pass through C18 in oleic acid made from copper-nickel-base catalyst:1 content reaches more than 70%, reaches high-purity oleic acid
Standard, wherein embodiment 6 are C18 in optimum embodiment, oleic acid:1 content has exceeded 80%, therefore, and the present invention has significant
Catalytic performance.
In summary, modification Cu-Ni@SiO of the invention2Catalyst has catalytic activity high and the good characteristic of selectivity,
Good effect, and catalyst preparation process and partial hydrogenation reaction have also been reached using high-purity oleic acid of this catalyst preparation
Mild condition, product purity is high, and cost is relatively low, it is expected to the cleaning procedure route as great competitiveness.
The basic principles, principal features and advantages of the present invention have been shown and described above.The technical staff of the industry should
Understand, the invention is not limited in any way for above-described embodiment, it is all to be obtained by the way of equivalent substitution or equivalent transformation
Technical scheme, all falls within protection scope of the present invention.
Claims (10)
1. the method that partial hydrogenation prepares copper-nickel-base catalyst of high-purity oleic acid, it is characterised in that comprise the following steps：
S1, the addition Cu (NO in reaction vessel3)2With Ni (NO3)2Mixed solution, ammoniacal liquor is slowly added dropwise and stirs, adjustment mixing
The pH value of solution is 8.0 ~ 10.0, is continuously stirred at room temperature, obtains suspension；
S2, pretreated SiO is added into suspension2, continue to stir 10 ~ 60 min, then suspension is placed in into mixture of ice and water
In be cooled to -5 ~ 5 DEG C, a certain amount of deionized water is slowly dropped in suspension, occur hydrolysis, continue stir extremely
Hydrolysis terminates, and suspension is filtered by vacuum, and is then repeatedly washed with deionized colourless to cleaning solution, obtains copper-ni-mh
Oxide solid mixture C u (OH)2-Ni(OH)2@SiO2；
S3, by solid mixture Cu (OH)2-Ni(OH)2@SiO2It is put into vacuum drying chamber and dries, takes out, place into after drying
Muffle kiln roasting, obtains copper-nickel oxide mixture C uO-NiO SiO2；
S4, by copper-nickel oxide mixture C uO-NiO@SiO2It is placed in tube furnace under hydrogen environment and carries out reduction reaction, obtains
To copper-nickel-base catalyst Cu-Ni@SiO2, then catalyst is wrapped in fixed oil.
2. the method that partial hydrogenation according to claim 1 prepares copper-nickel-base catalyst of high-purity oleic acid, its feature exists
In, in the step S1, Cu (NO3)2Solution concentration be 0.1 ~ 2.0 mol/L, Ni (NO3)2Solution concentration be 0.1 ~
2.0mol/L, Cu (NO3)2With Ni (NO3)2Mol ratio be 100:1~600:1.
3. the method that partial hydrogenation according to claim 1 prepares copper-nickel-base catalyst of high-purity oleic acid, its feature exists
In rotating speed is 390 rpm in the step S1, and rotating speed is 480 rpm in step S2.
4. the method that partial hydrogenation according to claim 1 prepares copper-nickel-base catalyst of high-purity oleic acid, its feature exists
In, in the step S2, SiO2Preprocess method be：Use the preceding h of drying process 10, deionized water in 100 DEG C of baking ovens
Volume be 200 ~ 600 mL, time for adding should be 1 ~ 5 h.
5. the method that partial hydrogenation according to claim 1 prepares copper-nickel-base catalyst of high-purity oleic acid, its feature exists
In in the step S3, vacuum drying chamber temperature is 80 ~ 150 DEG C, and drying time is 8 ~ 24 h.
6. the method that partial hydrogenation according to claim 1 prepares copper-nickel-base catalyst of high-purity oleic acid, its feature exists
In in the step S3, muffle furnace is 200 ~ 600 DEG C, and roasting time is 1 ~ 6 h.
7. the method that partial hydrogenation according to claim 1 prepares copper-nickel-base catalyst of high-purity oleic acid, its feature exists
In, in the step S4, hydrogen reducing temperature is 150 ~ 400 DEG C, and heating rate is 5 DEG C/min, and soaking time is 1 ~ 4 h,
It is finally cooled to room temperature.
8. the method that partial hydrogenation prepares high-purity oleic acid, it is characterised in that step is as follows：Industrial oleic acid is added in reactor,
Copper-nickel-base catalyst as made from claim any one of 1-7 is added, in the case where reaction temperature is 135 ~ 195 DEG C, leads to hydrogen
Gas makes reacting kettle inner pressure be 0.5 ~ 1.3 Mpa, reacts 1 ~ 3 h under the conditions of stir speed (S.S.) is 200 ~ 500 rpm, is added
Hydrogen product；Hydrogenation products are filtered, continue to recycle after the solid catalyst roasting reduction treatment filtered out, to gained
Filtrate produces high-purity oleic acid after being distilled.
9. the method that partial hydrogenation according to claim 8 prepares high-purity oleic acid, it is characterised in that the copper-Ni-based is urged
The consumption of agent is 0.5 ~ 2.5 % of industrial oleic acid gross mass.
10. the method that partial hydrogenation according to claim 8 prepares high-purity oleic acid, it is characterised in that the distillation mode
For vacuum distillation.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115069253A (en) * | 2022-07-14 | 2022-09-20 | 西安交通大学 | Antioxidant organic coated nickel-based catalyst and preparation method and application thereof |
| CN114405533B (en) * | 2021-11-19 | 2023-09-22 | 郑州大学 | Preparation method of catalyst for preparing furfuryl alcohol by hydrogenation of furfural |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7491820B2 (en) * | 2005-04-26 | 2009-02-17 | Archer-Daniels-Midland Company | Hydrogenation with copper compositions catalyst |
| CN103275815A (en) * | 2013-06-28 | 2013-09-04 | 如皋市双马化工有限公司 | Palmitoleic acid hydrogenation technology |
| CN105854951A (en) * | 2016-05-06 | 2016-08-17 | 江苏金马油脂科技发展有限公司 | Methods for preparing and applying antioxidant nanometer copper-based catalysts |
-
2017
- 2017-04-07 CN CN201710222541.2A patent/CN107008329A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7491820B2 (en) * | 2005-04-26 | 2009-02-17 | Archer-Daniels-Midland Company | Hydrogenation with copper compositions catalyst |
| CN103275815A (en) * | 2013-06-28 | 2013-09-04 | 如皋市双马化工有限公司 | Palmitoleic acid hydrogenation technology |
| CN105854951A (en) * | 2016-05-06 | 2016-08-17 | 江苏金马油脂科技发展有限公司 | Methods for preparing and applying antioxidant nanometer copper-based catalysts |
Non-Patent Citations (3)
| Title |
|---|
| 周长春编: "《铝土矿及其浮选技术》", 30 November 2011, 中国矿业大学出版社 * |
| 潘保凯等: "高选择性脂肪酸甲酯加氢催化剂的制备", 《中国油脂》 * |
| 解振兵等: "混合脂肪酸选择性加氢制高纯度油酸", 《日用化学品科学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114405533B (en) * | 2021-11-19 | 2023-09-22 | 郑州大学 | Preparation method of catalyst for preparing furfuryl alcohol by hydrogenation of furfural |
| CN115069253A (en) * | 2022-07-14 | 2022-09-20 | 西安交通大学 | Antioxidant organic coated nickel-based catalyst and preparation method and application thereof |
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