CN108164383A - A kind of method for preparing cis-pinane - Google Patents
A kind of method for preparing cis-pinane Download PDFInfo
- Publication number
- CN108164383A CN108164383A CN201810191288.3A CN201810191288A CN108164383A CN 108164383 A CN108164383 A CN 108164383A CN 201810191288 A CN201810191288 A CN 201810191288A CN 108164383 A CN108164383 A CN 108164383A
- Authority
- CN
- China
- Prior art keywords
- pinane
- catalyst
- cis
- nickel
- phosphorus alloy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane of uncertain configuration Natural products CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 title claims abstract description 51
- XOKSLPVRUOBDEW-DJLDLDEBSA-N (1r,4s,5r)-4,6,6-trimethylbicyclo[3.1.1]heptane Chemical compound C[C@H]1CC[C@H]2C(C)(C)[C@@H]1C2 XOKSLPVRUOBDEW-DJLDLDEBSA-N 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- OFNHPGDEEMZPFG-UHFFFAOYSA-N phosphanylidynenickel Chemical compound [P].[Ni] OFNHPGDEEMZPFG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910001096 P alloy Inorganic materials 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 238000012805 post-processing Methods 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 abstract 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 abstract 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010970 precious metal Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 229910000808 amorphous metal alloy Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910000521 B alloy Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- OXDMBACWGSVZRR-UHFFFAOYSA-L ethanol nickel(2+) diacetate Chemical compound C(C)O.C(C)(=O)[O-].[Ni+2].C(C)(=O)[O-] OXDMBACWGSVZRR-UHFFFAOYSA-L 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- -1 phosphorous acids sodium-hydrates Chemical class 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 235000011091 sodium acetates Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A kind of method for preparing cis-pinane, i.e. a kind of mesoporous carbon-based nickel-loaded phosphorus alloy of nitridation is the method that catalyst α pinene hydrogenations prepare cis-pinane, it is 50 in the mass ratio of α firpenes and catalyst it is characterized in that using the nickel-phosphorus alloy being supported on mesoporous carbonitride as catalyst:1‑500:1st, the mass ratio of nickel-phosphorus alloy load capacity and carrier carbonitride is 1:50‑1:1st, it reacts 0.5 10h at 0.2 5MPa of Hydrogen Vapor Pressure, 70 200 DEG C of reaction temperature and prepares cis-pinane, and recycle and reuse catalyst.Compared with prior art：1. catalyst activity is high, reaction speed is fast, firpene high conversion rate, cis-pinane high selectivity；2. product postprocessing is simple；3. used catalyst facilitates recycling, and repeat performance is good.
Description
Technical field
The present invention relates to a kind of methods for preparing cis-pinane, that is, are related to a kind of mesoporous nitridation carbon load nickel phosphorus alloy to urge
Agent is catalyzed method of the australene Hydrogenation for cis-pinane.
Background technology
Cis-pinane also known as (1 α, 2 β, 5 α) -2,6,6- trimethyl bicyclics [3.1.1] heptane, in medicine, pesticide, perfume etc.
Aspect tool has been widely used.The method of production cis-pinane mainly has precious metal catalyst hydrogenation method and Non-precious Metal Catalysts at present
Hydrogenation method.Non-precious Metal Catalysts hydrogenation method has the advantages that catalyst is at low cost, but there are catalyst activity is poor, substrate turns
The shortcomings of rate is low, selectivity of product is poor.Precious metal catalyst hydrogenation method has high catalyst activity, substrate conversion efficiency and product choosing
But there is expensive catalyst in the advantages that selecting property is high.The application is born using nickel-phosphorus amorphous alloy cheap and easy to get as a result,
Supported catalyst is catalyzed australene Hydrogenation for cis-pinane.
Invention content
The purpose of the present invention is the traditional cis-pinane production technology of substitution, and exploitation australene is under mild reaction conditions through urging
The highly selective orientation Hydrogenation of agent catalysis is for cis-pinane.
Based on as described above, the present invention relates to a kind of method for preparing cis-pinane, i.e., a kind of mesoporous carbon-based load of nitridation
Nickel-phosphorus alloy is catalyst australene Hydrogenation for the method for cis-pinane, it is characterised in that uses and is supported on mesoporous nitridation
Nickel-phosphorus alloy on carbon is catalyst, is 50 in the mass ratio of australene and catalyst:1-500:1st, nickel-phosphorus alloy load capacity with
The mass ratio of carrier carbonitride is 1:50-1:1st, 0.5-10h systems are reacted at Hydrogen Vapor Pressure 0.2-5MPa, 70-200 DEG C of reaction temperature
Standby cis-pinane, and recycle and reuse catalyst.
The invention is characterised in that the reaction condition is using the mass ratio of australene and catalyst as 20:1-200:1st, nickel phosphorus
The mass ratio of alloy load capacity and carrier carbonitride is 1:20-1:10th, Hydrogen Vapor Pressure 3-4MPa, 100-160 DEG C of reaction temperature, anti-
3-4h is preferred between seasonable.
The present invention solves this technical problem by the following technical programs：
Load-type nickel phosphorus alloy catalyst is prepared using dipping-chemical reduction method, detailed process is：By 10mL 0.5mol/
Nickel acetate ethanol solution, 30m ethyl alcohol and the 4.5g carbonitrides of L is stirred overnight at room temperature, 80 DEG C of vacuum drying, 250 DEG C of helium-atmospheres
Lower roasting 2h is enclosed, obtains the intermediate of carbonitride load nickel acetate；By intermediate add in 2.76g ortho phosphorous acids sodium-hydrates,
The mixture of 2.4g sodium acetates and 50mL deionized waters, is vigorously stirred, and pH is adjusted with the sodium hydroxide solution that mass fraction is 5%
Be worth be 11 after, be added dropwise and be to slowly warm up to flow back, when back flow reaction to no gas generates, by gained reaction mixture mistake
Filter, deionized water are washed filter cake to neutral, absolute ethyl alcohol and are washed 5 times, be dried in vacuo to get nickel-phosphorus amorphous alloy load capacity with
Carrier carbonitride mass ratio is 1:The 10 base amorphous nickel-phosphorus alloy catalyst of carbonitride.
It is 1 by australene 50g, catalyst 0.5g, nickel boron alloy load capacity and carrier carbonitride mass ratio:10th, hydrogen pressure
4h is reacted at power 4MPa, 140 DEG C of reaction temperature and prepares cis-pinane.After reaction by gained mixture slow cooling, be filtered to remove
Catalyst obtains product cis pinane, is tested through gas chromatographic analysis, australene conversion ratio 100%, cis-pinane selectivity
99.1%.
The present invention with tradition react compared with, its main feature is that：
1. catalyst activity is high, reaction speed is fast, firpene high conversion rate, cis-pinane high selectivity.
2. product postprocessing is simple.
3. used catalyst facilitates recycling, and repeat performance is good.
Specific implementation method
The method of the present invention is described further with reference to embodiment, is not limitation of the invention.
Embodiment 1：It is 1 by australene 50g, catalyst 0.5g, nickel-phosphorus alloy load capacity and carrier carbonitride mass ratio:
10th, 4h is reacted at Hydrogen Vapor Pressure 4MPa, 140 DEG C of reaction temperature and prepares cis-pinane.After reaction by gained mixture be down to room temperature,
Kettle, filtering reaction mixture removing catalyst are opened in pressure release, are obtained product cis pinane, are tested through gas chromatographic analysis, australene
Conversion ratio 100%, cis-pinane selectivity 99.1%.
Comparative example 1：It will be anti-at australene 50g, Pd/C catalyst 0.5g, Hydrogen Vapor Pressure 4MPa, 140 DEG C of reaction temperature
4h is answered to prepare cis-pinane.Gained mixture is down to room temperature, pressure release after reaction, opens kettle, filtering reaction mixture removing catalysis
Agent obtains product cis pinane, is tested through gas chromatographic analysis, australene conversion ratio 77.3%, cis-pinane selectivity
86.5%.
Comparative example 2：It will be at australene 50g, Raney's nickel catalyst 0.5g, Hydrogen Vapor Pressure 4MPa, 140 DEG C of reaction temperature
Reaction 4h prepares cis-pinane.After reaction by gained mixture be down to room temperature, pressure release, open kettle, filtering reaction mixture removing urge
Agent obtains product cis pinane, is tested through gas chromatographic analysis, australene conversion ratio 69.6%, cis-pinane selectivity
94.9%.
Comparative example 3：4h will be reacted at australene 50g, carbonitride 0.5g, Hydrogen Vapor Pressure 4MPa, 140 DEG C of reaction temperature
Prepare cis-pinane.Gained mixture is down to room temperature, pressure release after reaction, opens kettle, filtering reaction mixture removing catalyst, is obtained
It to product cis pinane, is tested through gas chromatographic analysis, australene conversion ratio 69.6%, cis-pinane selectivity 94.9%.
Comparative example 4：Australene 50g, the carbon-based Raney nickel 0.5g of nitridation, catalyst nickel loading and carrier are nitrogenized
Carbon mass ratio is 1:10th, 4h is reacted at Hydrogen Vapor Pressure 4MPa, 140 DEG C of reaction temperature and prepares cis-pinane.Gained is mixed after reaction
It closes object to be down to room temperature, pressure release, open kettle, filtering reaction mixture removing catalyst, product cis pinane is obtained, through gas-chromatography point
Analysis test, australene conversion ratio 86.6%, cis-pinane selectivity 95.9%.
Embodiment 2：It is 1 by australene 50g, catalyst 0.5g, nickel-phosphorus alloy load capacity and carrier carbonitride mass ratio:
10th, 10h is reacted at Hydrogen Vapor Pressure 0.2MPa, 200 DEG C of reaction temperature and prepares cis-pinane.Gained mixture is down to room after reaction
Kettle, filtering reaction mixture removing catalyst are opened in temperature, pressure release, are obtained product cis pinane, are tested through gas chromatographic analysis, and α-
Firpene conversion ratio 98.4%, cis-pinane selectivity 97.7%.
Embodiment 3：It is 1 by australene 50g, catalyst 0.1g, nickel-phosphorus alloy load capacity and carrier carbonitride mass ratio:1、
0.5h is reacted at Hydrogen Vapor Pressure 5MPa, 70 DEG C of reaction temperature and prepares cis-pinane.Gained mixture is down to room temperature after reaction, is let out
It presses, open kettle, filtering reaction mixture removing catalyst, obtain product cis pinane, tested through gas chromatographic analysis, australene turns
Rate 99.0%, cis-pinane selectivity 97.6%.
Embodiment 4：It is 1 by australene 50g, catalyst 0.3g, nickel-phosphorus alloy load capacity and carrier carbonitride mass ratio:
15th, 3h is reacted at Hydrogen Vapor Pressure 4MPa, 150 DEG C of reaction temperature and prepares cis-pinane.After reaction by gained mixture be down to room temperature,
Kettle, filtering reaction mixture removing catalyst are opened in pressure release, are obtained product cis pinane, are tested through gas chromatographic analysis, australene
Conversion ratio 100%, cis-pinane selectivity 99.3%.
Embodiment 5：Australene 50g, embodiment 1 are filtered into gained catalyst, other reaction conditions are same as Example 1
Under the conditions of reaction prepare cis-pinane, tested through gas chromatographic analysis, australene conversion ratio 100%, cis-pinane selectivity
98.9%.And gained catalyst is filtered to the embodiment and is reused under identical experiment condition 10 times, 10 reuses
Australene conversion ratio is tested more than 98%, the selectivity for pinane of taking advantage of a situation is also above 98%.
Claims (2)
1. a kind of method for preparing cis-pinane, i.e., a kind of mesoporous carbon-based nickel-loaded phosphorus alloy of nitridation is catalyst australene
Hydrogenation for cis-pinane method, it is characterised in that use the nickel-phosphorus alloy being supported on mesoporous carbonitride as catalyst,
The mass ratio of australene and catalyst is 50:1-500:1st, the mass ratio of nickel-phosphorus alloy load capacity and carrier carbonitride is 1:50-
1:1st, 0.5-10h is reacted at Hydrogen Vapor Pressure 0.2-5MPa, 70-200 DEG C of reaction temperature and prepares cis-pinane, and recycle and reuse
Catalyst.
2. preparation method as described in claim 1, it is characterised in that the reaction condition is with the matter of australene and catalyst
Amount is than being 20:1-200:1st, the mass ratio of nickel-phosphorus alloy load capacity and carrier carbonitride is 1:20-1:10th, Hydrogen Vapor Pressure 3-
4MPa, 100-160 DEG C of reaction temperature, reaction time 3-4h are preferred.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810191288.3A CN108164383A (en) | 2018-03-08 | 2018-03-08 | A kind of method for preparing cis-pinane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810191288.3A CN108164383A (en) | 2018-03-08 | 2018-03-08 | A kind of method for preparing cis-pinane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108164383A true CN108164383A (en) | 2018-06-15 |
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ID=62511091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810191288.3A Withdrawn CN108164383A (en) | 2018-03-08 | 2018-03-08 | A kind of method for preparing cis-pinane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108164383A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180415A (en) * | 2018-10-12 | 2019-01-11 | 青岛科技大学 | A method of it nitrogenizing carbon-based witch culture ni-b alloy catalysis australene and hydrogen is added to prepare cis-pinane |
| CN109331834A (en) * | 2018-10-12 | 2019-02-15 | 青岛科技大学 | A kind of method that ternary alloy catalyst catalysis australene adds hydrogen to prepare cis-pinane |
-
2018
- 2018-03-08 CN CN201810191288.3A patent/CN108164383A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180415A (en) * | 2018-10-12 | 2019-01-11 | 青岛科技大学 | A method of it nitrogenizing carbon-based witch culture ni-b alloy catalysis australene and hydrogen is added to prepare cis-pinane |
| CN109331834A (en) * | 2018-10-12 | 2019-02-15 | 青岛科技大学 | A kind of method that ternary alloy catalyst catalysis australene adds hydrogen to prepare cis-pinane |
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| PB01 | Publication | ||
| WW01 | Invention patent application withdrawn after publication | ||
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Application publication date: 20180615 |