CN105481633A - Method for preparing cis-pinane through selective hydrogenation of alpha-pinene - Google Patents
Method for preparing cis-pinane through selective hydrogenation of alpha-pinene Download PDFInfo
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- CN105481633A CN105481633A CN201510493684.8A CN201510493684A CN105481633A CN 105481633 A CN105481633 A CN 105481633A CN 201510493684 A CN201510493684 A CN 201510493684A CN 105481633 A CN105481633 A CN 105481633A
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- Prior art keywords
- pinane
- pinene
- catalyzer
- cis
- catalyst
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- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 title claims abstract description 63
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane of uncertain configuration Natural products CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 title claims abstract description 40
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 title claims abstract description 36
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 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 28
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 13
- 230000005291 magnetic effect Effects 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 230000035484 reaction time Effects 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000003368 amide group Chemical group 0.000 claims description 10
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006555 catalytic reaction Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 3
- 229910003321 CoFe Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 230000009466 transformation Effects 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 229930006728 pinane Natural products 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002122 magnetic nanoparticle Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000011943 nanocatalyst Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for preparing cis-pinane through selective hydrogenation of alpha-pinene is disclosed. According to the method, the mass ratio of alpha-pinene to a magnetic catalyst is 50:1-3, the reaction temperature is 140-180 DEG C, the hydrogenation pressure is 3.0-7.0 MPa, and the reaction time is 3.0-7.0 h, and thus cis-pinane is prepared. After the reaction is finished, the catalyst phase and the product phase are respectively recovered by utilizing an applied magnetic field. The catalyst phase can be directly reused without being processed. Under the technological conditions, the conversion rate of cis-pinane is larger than 96%, and the selectivity of cis-pinane is larger than 94%.
Description
Technical field
The present invention relates to the method that cis-pinane is prepared in the selective hydrogenation of a kind of catalysis α-pinene, namely relate to the method that cis-pinane is prepared in the selective hydrogenation of a kind of magnetic catalyst catalysis α-pinene.
Technical background
Pinane is a kind of transparent oily liquid with the breath of gentle pine needle sample, and can derive twenty or thirty kind terpenes spices, be the important intermediate of the spices such as synthesizing dihydromyrcenol, phantol.The main path of current industrial production pinane obtains with terebinthine main component α-pinene shortening.The highest with cis-pinane reactive behavior again in pinane, think and ensure the quality of derived product, α-pinene shortening prepare the purity of cis-pinane in the process of pinane and selectivity just extremely important, this is just very high to the performance requriements of catalyzer.At present, catalyzer for catalysis α-pinene hydrogenation synthesis pinane mainly contain Raney-Ni (Nanjing forest product industry institute. natural resin process technology [M]. Beijing: China Forestry Publishing House, 1982.284.), Pd/C (Wang Biyu etc., palladium carbon catalyst is used for the research [J] that α-pinene atmospheric hydrogenation prepares pinane. Fujian chemical industry, 1997,4:14-15) etc. metal catalyst.The problem that the selectivity of these catalyzer ubiquities to cis-pinane is low.Research finds to use Ru/Al
2o
3during for catalyzer, the deficiency of traditional catalyst can be overcome, 96% is reached to cis-pinane selectivity, but this poor catalyst stability, very fast inactivation (MarkSP, LawrencevilieNJ.Hydrogenationofpinenetosic-pinane [P] .US:4310714,1982-12-10).Therefore, research and develop the good selective hydrogenation catalyst of New Cycle use properties and become an important and problem demanding prompt solution.
In recent years, the research of magnetic nano-catalyst achieves larger progress, and magnetic Nano material supporting catalytic active component obtains deeply to be inquired into widely.The advantage of magnetic catalyst mainly comprises: 1, heat energy is high, good mechanical stability, is applicable to scale operation; 2, unique paramagnetic properties, most of organic solvent is insoluble to, can Separation and Recovery effectively by externally-applied magnetic field, achieve the recycling of catalyzer; 3, in simple, the preparation process of preparation method, refuse generation is few, has fully demonstrated principle and the thought of Green Chemistry; 4, modify after magnetic nano-particle can be stable be dispersed in the middle of catalyst system.The present invention proposes to adopt the selective hydrogenation of magnetic catalyst catalysis α-pinene to prepare the novel method of cis-pinane thus.
Summary of the invention
Cis-pinane is prepared in the environmentally friendly catalyst α-pinene selective hydrogenation that the object of the invention is to propose a kind of catalytic performance excellent, effectively can improve the selectivity of cis-pinane, and the recovery repeat performance of catalyzer is better.
The present invention relates to the method that cis-pinane is prepared in the selective hydrogenation of a kind of catalysis α-pinene, it is characterized in that α-pinene is 50: 1 ~ 3 with catalyst quality ratio, temperature of reaction 140 ~ 180 DEG C, react 3.0 ~ 7.0h under the condition of hydrogen pressure 3.0 ~ 7.0MPa and prepare cis-pinane, after reaction terminates, utilize externally-applied magnetic field to reclaim catalyzer phase and product phase respectively.Catalyzer without the need to process, direct reuse.
The present invention is characterized in that described magnetic catalyst is M-NH
2-Ru type catalyzer, wherein M-NH
2in-Ru, Ru massfraction is 5% ~ 10%, M is Fe
3o
4, Fe
2o
3, ZnFe
2o
4, MnFe
2o
4, CoFe
2o
4in one, the amido of the fixing Ru adopted is Putriscine, 1,6-hexanediamine, 1,8-octamethylenediamine, 1,10-certain herbaceous plants with big flowers diamines, the one in 1,12-dodecamethylene diamine.
Concrete steps are:
(1) α-pinene is prepared as to the typical case of cis-pinane and magnetic catalyst mass ratio is 50: 1 ~ 3, put in the autoclave with mechanical stirring, thermocouple thermometer, be filled with 3.0 ~ 7.0MPa hydrogen, heated and stirred reaction 3.0 ~ 7.0h at temperature of reaction 140 ~ 180 DEG C.Be cooled to room temperature after reaction terminates, under the effect of externally-applied magnetic field, realize being separated of product and catalyzer.Obtain product cis pinane.
(2) catalyzer that uses of method of the present invention is reusable, because catalyzer has magnetic response characteristic, after reaction terminates, being separated of product and catalyzer phase directly can be completed in a kettle. under the effect of externally-applied magnetic field, namely catalyzer can be used for next step catalytic hydrogenation reaction without the need to any process, reuse 5 times, catalytic performance has no obvious decline.
The present invention, compared with conventional catalyst technique, is characterized in:
(1) catalyzer has efficient catalytic activity and selectivity.
(2) product postprocessing is simple, and gained by product is few.
(3) externally-applied magnetic field is utilized simply efficiently and product separation, namely can be used for reaction next time without any process, and catalytic performance can to have no reduction, recycles performance good after catalyst reaction.
Specific implementation method
Being described further method of the present invention below in conjunction with embodiment, is not limitation of the invention.
Embodiment 1: by 2.5g α-pinene and 0.1gFe
3o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,6-hexanediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be separated mutually direct to product and catalyzer in still, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 98.1%, and the selectivity of cis-pinane is 95.6%.
Embodiment 2: by 2.5g α-pinene and 0.08gFe
3o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,6-hexanediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be separated mutually direct to product and catalyzer in still, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 96.6%, and the selectivity of cis-pinane is 94.7%.
Embodiment 3: by 2.5g α-pinene and 0.1gFe
3o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,6-hexanediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 170 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be directly separated in still by product with catalyzer, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 98.3%, and the selectivity of cis-pinane is 94.1%.
Embodiment 4: by 2.5g α-pinene and 0.1gZnFe
2o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,6-hexanediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be directly separated in still by product with catalyzer, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 97.3%, and the selectivity of cis-pinane is 94.1%.
Embodiment 5: by 2.5g α-pinene and 0.1gZnFe
2o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,8-octamethylenediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be directly separated in still by product with catalyzer, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 97.9%, and the selectivity of cis-pinane is 95.2%.
Embodiment 6: by 2.5g α-pinene and 0.1gZnFe
2o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by Putriscine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be directly separated in still by product with catalyzer, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 96.4%, and the selectivity of cis-pinane is 94.3%.
Embodiment 7: by 2.5g α-pinene and 0.1gFe
3o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,6-hexanediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 6.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be directly separated in still by product with catalyzer, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 98.1%, and the selectivity of cis-pinane is 95.0%.
Embodiment 8: by 2.5g α-pinene and 0.1gFe
3o
4-NH
2-Ru (wherein the massfraction of Ru is 8%, and amido is provided by 1,6-hexanediamine) adds in stainless steel autoclave, and air in hydrogen exchange still, is then filled with 5.0MPa hydrogen, heated and stirred 5h at 160 DEG C, leaves standstill and is cooled to room temperature.Under the effect of externally-applied magnetic field, be directly separated in still by product with catalyzer, the catalyzer after separation can be directly used in lower secondary response.α-pinene transformation efficiency is 96.1%, and the selectivity of cis-pinane is 94.8%.
Embodiment 9-14: catalyzer, with embodiment 1, is just changed into the catalyzer reclaimed in embodiment 1 by experiment condition and step, carry out repeating reuse experiment for five times, reuse the results are shown in Table 1.
The repetition reuse result of table 1 catalyzer
| Reuse number of times | 1 | 2 | 3 | 4 | 5 |
| Transformation efficiency/% | 98.1 | 98.3 | 97.9 | 97.6 | 98.0 |
| Selectivity/% | 95.6 | 95.1 | 95.3 | 94.8 | 95.2 |
[0027]
Claims (1)
1. the method for cis-pinane is prepared in catalysis α-pinene selective hydrogenation, it is characterized in that m (α-pinene): m (catalyzer)=50: 1 ~ 3, temperature of reaction 140 ~ 180 DEG C, hydrogen pressure 3.0 ~ 7.0MPa, reaction times 3.0 ~ 7.0h; Wherein catalyzer is the magnetic catalyst of carried noble metal Ru, and structure is M-NH
2the massfraction of-Ru, Ru is 5% ~ 10%, M is Fe
3o
4, Fe
2o
3, ZnFe
2o
4, MnFe
2o
4, CoFe
2o
4in one, the amido of the fixing Ru adopted is Putriscine, 1,6-hexanediamine, 1,8-octamethylenediamine, 1,10-certain herbaceous plants with big flowers diamines, the one in 1,12-dodecamethylene diamine; Reaction terminate after utilize externally-applied magnetic field to reclaim catalyzer phase and product phase respectively, catalyzer without the need to process, direct reuse.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510493684.8A CN105481633A (en) | 2015-08-12 | 2015-08-12 | Method for preparing cis-pinane through selective hydrogenation of alpha-pinene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510493684.8A CN105481633A (en) | 2015-08-12 | 2015-08-12 | Method for preparing cis-pinane through selective hydrogenation of alpha-pinene |
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| Publication Number | Publication Date |
|---|---|
| CN105481633A true CN105481633A (en) | 2016-04-13 |
Family
ID=55668958
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|---|---|---|---|
| CN201510493684.8A Pending CN105481633A (en) | 2015-08-12 | 2015-08-12 | Method for preparing cis-pinane through selective hydrogenation of alpha-pinene |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107649147A (en) * | 2017-10-23 | 2018-02-02 | 湖南长岭石化科技开发有限公司 | Hydrogenation catalyst, its application and the method for preparing cis-pinane using its catalysis α pinene hydrogenation |
| CN109912374A (en) * | 2019-04-10 | 2019-06-21 | 青岛科技大学 | A kind of method that australene adds hydrogen to prepare cis-pinane |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4310714A (en) * | 1980-12-10 | 1982-01-12 | Union Camp Corporation | Hydrogenation of α-pinene to cis-pinane |
| US5132270A (en) * | 1990-08-30 | 1992-07-21 | Huels Aktiengesellschaft | Ultrasound method of reactivating deactivated hydrogenation catalyts |
| CN102205245A (en) * | 2011-04-11 | 2011-10-05 | 天津市安凯特催化剂有限公司 | Method for improving selectivity of cis pinane prepared by alpha-pinene hydrogenation |
-
2015
- 2015-08-12 CN CN201510493684.8A patent/CN105481633A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4310714A (en) * | 1980-12-10 | 1982-01-12 | Union Camp Corporation | Hydrogenation of α-pinene to cis-pinane |
| US5132270A (en) * | 1990-08-30 | 1992-07-21 | Huels Aktiengesellschaft | Ultrasound method of reactivating deactivated hydrogenation catalyts |
| CN102205245A (en) * | 2011-04-11 | 2011-10-05 | 天津市安凯特催化剂有限公司 | Method for improving selectivity of cis pinane prepared by alpha-pinene hydrogenation |
Non-Patent Citations (1)
| Title |
|---|
| 王海群: "乙二胺协助的磁性Pd/Fe3O4球的控制制备及其性能研究", 《中国优秀硕士学位论文全文数据库（电子期刊）工程科技I辑》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107649147A (en) * | 2017-10-23 | 2018-02-02 | 湖南长岭石化科技开发有限公司 | Hydrogenation catalyst, its application and the method for preparing cis-pinane using its catalysis α pinene hydrogenation |
| CN107649147B (en) * | 2017-10-23 | 2020-08-07 | 湖南长岭石化科技开发有限公司 | Hydrogenation catalyst, application thereof and method for preparing cis-pinane by catalyzing α -pinene hydrogenation by using hydrogenation catalyst |
| CN109912374A (en) * | 2019-04-10 | 2019-06-21 | 青岛科技大学 | A kind of method that australene adds hydrogen to prepare cis-pinane |
| CN109912374B (en) * | 2019-04-10 | 2022-01-18 | 青岛科技大学 | Method for preparing cis-pinane by hydrogenating alpha-pinene |
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Application publication date: 20160413 |