CN107513004A - A kind of method and its catalyst of α firpenes selective hydrogenation synthesizing cis pinane - Google Patents
A kind of method and its catalyst of α firpenes selective hydrogenation synthesizing cis pinane Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
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- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J23/6525—Molybdenum
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Abstract
The invention discloses a kind of catalyst for α pinene hydrogenation synthesizing cis pinanes and preparation method thereof, the catalyst is Ru/Al2O3/MoO3, wherein Ru and Al2O3/MoO3Mass ratio be 3~10:100.The invention also discloses a kind of method of α firpenes selective hydrogenation synthesizing cis pinane, Ru/Al2O3/MoO3The mass ratio of ternary complex catalyst and α firpenes is 0.1~1:100, the two mixing, reaction temperature is 100 DEG C~140 DEG C, and Hydrogen Vapor Pressure is 2~5MPa, and the reaction time is that cis-pinane is prepared under 4~8h.Ru/Al prepared by the present invention2O3/MoO3Ternary complex catalyst category heterogeneous catalysis, preparation technology is simple, easily recovery, and at low temperature with regard to energy efficient catalytic α pinene hydrogenation synthesizing cis pinanes, high conversion rate, selectivity is high, better than similar heterogeneous catalysis.
Description
Technical field
The present invention relates to a kind of method of australene high-selective and hydrogenating synthesizing cis pinane, more particularly to a kind of Ru/
Al2O3/MoO3Ternary complex catalyst catalytic hydrogenation prepares the preparation method of cis-pinane, further relates to a kind of australene selectivity
The Ru/Al of hydrogenation synthesis cis-pinane2O3/MoO3The preparation method of ternary complex catalyst, such catalyst can be in lower temperatures
Very high conversion ratio and selectivity are shown in lower catalysis australene hydrogenation synthesis cis-pinane reaction.
Background technology
Firpene is terebinthine main component, and its content can change in the range of 60-99%.The pinane produced by pinene hydrogenation
Alkane is to synthesize the raw material of large spices and the raw materials of synthesising complex E such as linalool, dihydromyrcenol, bergamio, because
This, firpene catalytic hydroconversion be pinane be a technical process for having significant application value, wherein cis-pinane have compared with
High reactivity, it is the key for ensureing synthesis downstream product quality.
At present, prepared by firpene catalytic hydrogenation is occupied in the reaction of cis-pinane with Pd/C and Raney Ni heterogeneous catalysis
More, remaining dogface waits (research [J] the Guangzhou chemistry of modified Pd/C catalytic hydrogenation firpenes, 1999,24 (2):23-27.) research modification
Pd/C catalysts hydrogenate firpene pinane, as a result show with CuCl2The Pd/C catalyst of modification is to australene conversion ratio
63.3%, cis-pinane selectivity 93.1%.Han Huan et al. (Ni/TiO2-Al2O3The preparation of catalyst and its turpentine oil be catalyzed
Application [J] chemistry of forest product and industry in hydrogenation reaction, 2016,1:TiO 92-98.) is prepared with sol-gal process2-Al2O3It is multiple
For conversion ratio up to 97.27%, the selectivity of product cis pinane is 96.15% when closing carrier catalysis australene hydrogenation reaction.These
Catalyst generally existing cis-pinane is selectively relatively low, it is necessary to which being reacted under a variety of auxiliary agents causes the complex grade of preparation section not
Foot.Patent CN105418355A, which is disclosed, is catalyzed australene Hydrogenation for the method for cis-pinane, the technology in a kind of aqueous medium
By the way that using PVA as stabilizer, water is medium, the ruthenium nano particle hydrosol is prepared by hydrogenating reduction method, in gentle technique
Under the conditions of, the high conversion rate of australene is up to 99.6%, and the selectivity of cis-pinane is up to more than 99.1%.But the homogeneous catalysis
Agent has the shortcomings that repeat performance is bad, and therefore, research and development novel environmental is friendly and the good selectivity of catalytic performance adds
Hydrogen heterogeneous catalysis has highly important application value.
The content of the invention
The purpose of the present invention is to propose to one kind is environment-friendly, catalytic performance is outstanding, to cis-pinane conversion ratio and selectivity
High Ru/Al2O3/MoO3Ternary complex catalyst, this Ru/Al2O3/MoO3Ternary complex catalyst catalysis australene hydrogenation closes
Into cis-pinane, so as to provide a kind of side of the australene high-selective and hydrogenating synthesizing cis pinane of high conversion and selectivity
Method.
The present invention is realized by following technical proposals.
A kind of catalyst for australene hydrogenation synthesis cis-pinane, the catalyst are Ru/Al2O3/MoO3, wherein Ru
With Al2O3/MoO3Mass ratio be 3~10:100.More particularly, Al2O3With MoO3Mass ratio be 1：1.
A kind of preparation method of catalyst for australene hydrogenation synthesis cis-pinane, it is characterized in that:In mass ratio 1:1
By Al2O3And MoO3Add in reaction vessel, add deionized water and ultrasonic disperse, then adjust pH=9-10；According to Ru with
Al2O3/MoO3Mass ratio be 3~10:100 add RuCl3, normal temperature, which is stood, reacts a period of time, then heats up and adds appropriate
Sodium borohydride solution, after reaction, room temperature is cooled to, centrifuge, be dried to obtain Ru/Al2O3/MoO3Ternary complex catalyst.
More specifically, a kind of preparation method of catalyst for australene hydrogenation synthesis cis-pinane, step are as follows：
1. weigh 0.05g Al2O3With 0.05g MoO3Add in conical flask, add 250ml deionized water thereto,
Ultrasonic 1h；
After 2. ultrasound terminates, Na is added into conical flask2CO3Solution, adjust the pH=9-10 in conical flask；
3. 35 DEG C are heated to, according to Ru and Al2O3/MoO3Mass ratio be 3~10:100 add 0.03mmol-0.1mmol
RuCl3, 3h is kept at 35 DEG C；
4. after keeping 3h to terminate at 35 DEG C, 95 DEG C are warming up to, adds 0.2-2ml 300mM sodium borohydride solution, then
0.5h is kept at 95 DEG C；
5. 4. room temperature will be cooled to gained liquid, centrifuge 3-4 times, centrifugation products therefrom is then dried into 10- at 60 DEG C
15h, obtain Ru/Al2O3/MoO3Ternary complex catalyst.
Present invention also offers a kind of method of australene selective hydrogenation synthesizing cis pinane, Ru/Al2O3/MoO3Ternary
The mass ratio of composite catalyst and australene is 0.1~1:100, the two mixing, reaction temperature is 100 DEG C~140 DEG C, hydrogen pressure
Power is 2~5MPa, and the reaction time is that cis-pinane is prepared under 4~8h, and catalytic activity is high, and catalyst is environment-friendly, rear place
Reason is simple, reusable edible.
Detailed step is as follows：
It is 0.1~1 according to the mass ratio of catalyst and australene 1. taking 50g australenes to add in reactor:100 add
The Ru/Al made2O3/MoO3Ternary complex catalyst 0.05-0.5g, closes reactor；
2. being replaced three to four times with hydrogen under gauge pressure 2.5-3.5MPa, leak detection, confirm that reactor sealing is intact；
3. opening hydrogen gas valve, it is 2-5MPa to adjust pressure in kettle, reactor heating controller is opened, in 100-140
DEG C, react 4-8h under mixing speed 500r/min.
Ru/Al prepared by the present invention2O3/MoO3Ternary complex catalyst category heterogeneous catalysis, preparation technology is simple,
Easily recovery, at low temperature with regard to energy efficient catalytic australene hydrogenation synthesis cis-pinane, heating stirring 5h, is filled with 100 DEG C
3.0MPa hydrogen, Ru/Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) it is catalyzed australene hydrogenation reaction
Conversion ratio is 100%, and the selectivity of cis-pinane is 97.75%.Better than similar heterogeneous catalysis.
Embodiment
The method of the present invention is described further with reference to embodiment, is not limitation of the invention.
Embodiment 1Ru and Al2O3/MoO3Mass ratio be 3:100 Ru/Al2O3/MoO3Ternary complex catalyst
1. weigh 0.05g Al2O3With 0.05g MoO3Add in conical flask, add 250ml deionized water thereto,
Ultrasonic 1h；
After 2. ultrasound terminates, Na is added into conical flask2CO3Solution, adjust the pH=9-10 in conical flask；
3. being heated to 35 DEG C, 0.03mmol RuCl is added3, 3h is kept at 35 DEG C；
4. after keeping 3h to terminate at 35 DEG C, 95 DEG C are warming up to, adds 0.2-2ml 300mM sodium borohydride solution, then
0.5h is kept at 95 DEG C；
5. 4. room temperature will be cooled to gained liquid, centrifuge 3-4 times, centrifugation products therefrom is then dried into 10- at 60 DEG C
15h, obtain Ru/Al2O3/MoO3Ternary complex catalyst.
Embodiment 2Ru and Al2O3/MoO3Mass ratio be 5:100 Ru/Al2O3/MoO3Ternary complex catalyst
1. weigh 0.05g Al2O3With 0.05g MoO3Add in conical flask, add 250ml deionized water thereto,
Ultrasonic 1h；
After 2. ultrasound terminates, Na is added into conical flask2CO3Solution, adjust the pH=9-10 in conical flask；
3. being heated to 35 DEG C, 0.05mmol RuCl is added3, 3h is kept at 35 DEG C；
4. after keeping 3h to terminate at 35 DEG C, 95 DEG C are warming up to, adds 0.2-2ml 300mM sodium borohydride solution, then
0.5h is kept at 95 DEG C；
5. 4. room temperature will be cooled to gained liquid, centrifuge 3-4 times, centrifugation products therefrom is then dried into 10- at 60 DEG C
15h, obtain Ru/Al2O3/MoO3Ternary complex catalyst.
Embodiment 3Ru and Al2O3/MoO3Mass ratio be 10:100 Ru/Al2O3/MoO3Ternary complex catalyst
1. weigh 0.05g Al2O3With 0.05g MoO3Add in conical flask, add 250ml deionized water thereto,
Ultrasonic 1h；
After 2. ultrasound terminates, Na is added into conical flask2CO3Solution, adjust the pH=9-10 in conical flask；
3. being heated to 35 DEG C, 0.1mmol RuCl is added3, 3h is kept at 35 DEG C；
4. after keeping 3h to terminate at 35 DEG C, 95 DEG C are warming up to, adds 0.2-2ml 300mM sodium borohydride solution, then
0.5h is kept at 95 DEG C；
5. 4. room temperature will be cooled to gained liquid, centrifuge 3-4 times, centrifugation products therefrom is then dried into 10- at 60 DEG C
15h, obtain Ru/Al2O3/MoO3Ternary complex catalyst.
Australene selective hydrogenation synthesizing cis pinane
Embodiment 4：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 3:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 120 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 96.39%.
Embodiment 5：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 120 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 96.91%.
Embodiment 6：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 10:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 120 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 93.1%.
Embodiment 7：It is 0.5 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.25gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 120 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 96.44%.
Embodiment 8：It is 1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.5g Ru/Al2O3/
MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, using in hydrogen displacement kettle
3.0MPa hydrogen is filled with after air 4 times, the heating stirring 5h at 120 DEG C, standing is cooled to room temperature.The conversion ratio of australene is
100%, the selectivity of cis-pinane is 96.6%.
Embodiment 9：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 100 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 97.75%.
Embodiment 10：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 110 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 96.98%.
Embodiment 11：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 4h at 120 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 97.36%, and the selectivity of cis-pinane is 94.58%.
Embodiment 12：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
2.0MPa hydrogen is filled with after changing in kettle air 3 times, the heating stirring 8h at 140 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 97.16%, and the selectivity of cis-pinane is 95.47%.
Embodiment 13：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
5.0MPa hydrogen is filled with after changing in kettle air 3 times, the heating stirring 8h at 130 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 98.31%, and the selectivity of cis-pinane is 96.52%.
Embodiment 14：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 3h at 120 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 93.94%, and the selectivity of cis-pinane is 95.33%.
Embodiment 15：It is 0.1 according to the mass ratio of catalyst and australene:100, by 50g australenes and 0.05gRu/
Al2O3/MoO3(wherein Ru and Al2O3/MoO3Mass ratio be 5:100) add in ptfe autoclave, put using hydrogen
3.0MPa hydrogen is filled with after changing in kettle air 4 times, the heating stirring 5h at 130 DEG C, standing is cooled to room temperature.The conversion of australene
Rate is 100%, and the selectivity of cis-pinane is 95.74%.
Embodiment described above is a kind of preferable scheme of the present invention, not the present invention is made any formal
Limitation, there are other variants and remodeling on the premise of without departing from the technical scheme described in claim.
Claims (6)
1. a kind of catalyst for australene hydrogenation synthesis cis-pinane, it is characterized in that：The catalyst is Ru/Al2O3/MoO3,
Wherein Ru and Al2O3/MoO3Mass ratio be 3~10:100.
2. a kind of catalyst for australene hydrogenation synthesis cis-pinane according to claim 1, it is characterized in that：Al2O3
With MoO3Mass ratio be 1：1.
3. a kind of preparation method of catalyst for australene hydrogenation synthesis cis-pinane, it is characterized in that:In mass ratio 1:1 will
Al2O3And MoO3Add in reaction vessel, add deionized water and ultrasonic disperse, then adjust pH=9-10；According to Ru with
Al2O3/MoO3Mass ratio be 3~10:100 add RuCl3, normal temperature, which is stood, reacts a period of time, then heats up and adds appropriate
Sodium borohydride solution, after reaction, room temperature is cooled to, centrifuge, be dried to obtain Ru/Al2O3/MoO3Ternary complex catalyst.
4. a kind of preparation method of catalyst for australene hydrogenation synthesis cis-pinane according to claim 3, its
It is characterized in：Step is as follows：
1. weigh 0.05g Al2O3With 0.05g MoO3Add in conical flask, add 250ml deionized water, ultrasound thereto
1h；
After 2. ultrasound terminates, Na is added into conical flask2CO3Solution, adjust the pH=9-10 in conical flask；
3. 35 DEG C are heated to, according to Ru and Al2O3/MoO3Mass ratio be 3~10:100 add 0.03mmol-0.1mmol's
RuCl3, 3h is kept at 35 DEG C；
4. after keeping 3h to terminate at 35 DEG C, 95 DEG C are warming up to, 0.2-2ml 300mM sodium borohydride solution is added, then 95
0.5h is kept at DEG C；
5. 4. room temperature will be cooled to gained liquid, centrifuge, then centrifugation products therefrom is dried, obtains Ru/Al2O3/MoO3Ternary
Composite catalyst.
5. a kind of method of australene selective hydrogenation synthesizing cis pinane, it is characterized in that：Ru/Al2O3/MoO3Tri compound is urged
The mass ratio of agent and australene is 0.1~1:100, the two mixing, reaction temperature is 100 DEG C~140 DEG C, Hydrogen Vapor Pressure 2
~5MPa, reaction time are that cis-pinane is prepared under 4~8h.
6. a kind of method of australene selective hydrogenation synthesizing cis pinane according to claim 5, it is characterized in that：Step
It is as follows：
It is 0.1~1 according to the mass ratio of catalyst and australene 1. weighing 50g australenes to add in reactor:100 add system
Good Ru/Al2O3/MoO3Ternary complex catalyst 0.05-0.5g, closes reactor；
2. being replaced three to four times with hydrogen under gauge pressure 2.5-3.5MPa, leak detection, confirm that reactor sealing is intact；
3. open hydrogen gas valve, adjust kettle in pressure be 2-5MPa, open reactor heat up controller, in 100-140 DEG C, stir
Mix and react 4-8h under speed 500r/min.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110256185A (en) * | 2019-07-18 | 2019-09-20 | 青岛科技大学 | A kind of australene method of hydrotreating based on biomass-based catalyst |
| CN112980501A (en) * | 2021-02-24 | 2021-06-18 | 青岛科技大学 | One-pot preparation method of turpentine-based biomass high-energy-density fuel |
| CN113735677A (en) * | 2021-09-30 | 2021-12-03 | 江西省科学院应用化学研究所 | Method for preparing cis-pinane by catalyzing hydrogenation of alpha-pinene with L-malic acid intercalation magnalium hydrotalcite loaded ruthenium catalyst |
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| CN110256185B (en) * | 2019-07-18 | 2022-02-08 | 青岛科技大学 | Biomass-based catalyst-based alpha-pinene hydrogenation method |
| CN112980501A (en) * | 2021-02-24 | 2021-06-18 | 青岛科技大学 | One-pot preparation method of turpentine-based biomass high-energy-density fuel |
| CN113735677A (en) * | 2021-09-30 | 2021-12-03 | 江西省科学院应用化学研究所 | Method for preparing cis-pinane by catalyzing hydrogenation of alpha-pinene with L-malic acid intercalation magnalium hydrotalcite loaded ruthenium catalyst |
| CN113735677B (en) * | 2021-09-30 | 2024-02-27 | 江西省科学院应用化学研究所 | Method for preparing cis-pinane by catalyzing alpha-pinene hydrogenation through L-malic acid intercalated magnesium-aluminum hydrotalcite supported ruthenium catalyst |
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