CN102408291B - Method for reducing aromatic hydrocarbon by indirect hydrogen transfer - Google Patents
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- CN102408291B CN102408291B CN2011103066469A CN201110306646A CN102408291B CN 102408291 B CN102408291 B CN 102408291B CN 2011103066469 A CN2011103066469 A CN 2011103066469A CN 201110306646 A CN201110306646 A CN 201110306646A CN 102408291 B CN102408291 B CN 102408291B
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- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 48
- 239000001257 hydrogen Substances 0.000 title claims abstract description 48
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 title 1
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006722 reduction reaction Methods 0.000 claims abstract description 19
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 26
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 24
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 24
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 20
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 18
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 16
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 claims description 15
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 10
- GVJFFQYXVOJXFI-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a,9,9a,10,10a-tetradecahydroanthracene Chemical compound C1C2CCCCC2CC2C1CCCC2 GVJFFQYXVOJXFI-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 230000009467 reduction Effects 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 230000006872 improvement Effects 0.000 description 4
- 238000004523 catalytic cracking Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for reducing aromatic hydrocarbon by indirect hydrogen transfer. The aromatic hydrocarbon is reduced into hydrocarbon alkyl in the presence of catalyst, hydrogen transfer medium and hydrogen; and the reduction reaction conditions are as follows: dose ratio of the catalyst to the aromatic hydrocarbon is 0.11-1g/0.05mol; dose ratio of the hydrogen transfer medium to the aromatic hydrocarbon is 0.005-0.05mol/0.05mol; hydrogen is filled to 0.2-0.4MPa; reaction temperature is 50-180 degrees centigrade; and the reaction time is 1-7h. The method for reducing aromatic hydrocarbon disclosed by the invention is convenient to operate and high-efficiency.
Description
Technical field
The present invention relates to a kind of method of reducing aromatic hydrocarbon by indirect hydrogen transfer.
Background technology
Aromatic hydrocarbons is the major ingredient that forms catalytic cracking (FCC) externally extracting oil, the a large amount of externally extracting oil of the annual generation of China's catalytic cracking unit, at present the utilization of FCC externally extracting oil there is number of ways, and with its hydro-reduction, be that to be reused for catalytic cracking after stable hydrocarbon be a kind of approach that utilizes comparatively efficiently again.The reduction of aromatic hydrocarbons at present is to be hydrogenated to the master, and report is arranged, and (Carbon 49 (4): 1326-1322), have and report is once arranged take loading type Ni as catalyst naphthalene hydrogenation (CN101602644) take Ru-NP/CDG as the catalyst benzene hydrogenation.The hydrogenating reduction relative difficult that contains the aromatic hydrocarbons of a plurality of phenyl ring, report also less, once had the report take Rh as catalyst anthracene hydrogenation (Journal ofPhysical Chemistry C, 113 (46), 19782-19788).The aromatic ring method of hydrotreating of above report all can obtain higher transformation efficiency, but also exist total defect: the solubleness due to hydrogen in aromatic hydrocarbon is poor, the condition that makes hydrogenation is harsh (pressure or temperature are higher, and perhaps the reaction times is longer) comparatively, and speed of response is slower.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of easy to operate and reduce efficiently the method for aromatic hydrocarbon.
In order to solve the problems of the technologies described above, the invention provides a kind of method of reducing aromatic hydrocarbon by indirect hydrogen transfer, under the condition that catalyzer, hydrogen transference medium and hydrogen exist, aromatic hydrocarbon is reduced to alkane;
Reduction reaction conditions is as follows:
The amount ratio of catalyzer and aromatic hydrocarbon is: 0.11～1g catalyzer/0.05mol aromatic hydrocarbon;
The amount ratio of hydrogen transference medium and aromatic hydrocarbon is: 0.005～0.05mol hydrogen transference medium/0.05mol aromatic hydrocarbon;
Fill hydrogen to 0.2～4MPa, temperature of reaction is 50～180 ℃, and the reaction times is 1～7 hour.
As the improvement of the method for reducing aromatic hydrocarbon by indirect hydrogen transfer of the present invention, reduction reaction conditions is as follows:
The amount ratio of catalyzer and aromatic hydrocarbon is: 0.11～0.5g catalyzer/0.05mol aromatic hydrocarbon;
Hydrogen transference medium and aromatic hydrocarbon amount ratio be: 0.005～0.015mol hydrogen transference medium/0.05mol aromatic hydrocarbon;
Fill hydrogen to 0.2～3MPa; Temperature of reaction is 50～150 ℃, and the reaction times is 1～5 hour.
Further improvements in methods as reducing aromatic hydrocarbon by indirect hydrogen transfer of the present invention: aromatic hydrocarbon is at least a in benzene, toluene, ethylbenzene, dimethylbenzene, naphthalene, anthracene and biphenyl;
The alkane that benzene is reduced rear generation is hexanaphthene, the alkane that toluene is reduced rear generation is methylcyclohexane, the alkane that ethylbenzene is reduced rear generation is ethylcyclohexane, the alkane that dimethylbenzene is reduced rear generation is dimethyl cyclohexane, the alkane that naphthalene is reduced rear generation is perhydronaphthalene, the alkane that anthracene is reduced rear generation is perhydroanthracene, and the alkane that biphenyl is reduced rear generation is bicyclohexane.
Further improvements in methods as reducing aromatic hydrocarbon by indirect hydrogen transfer of the present invention: catalyzer is Pt/C (5%wt, the weight content that is Pt in Pt/C is 5%), Pd/C (5%wt, namely in Pd/C, the weight content of Pd is 5%), Ru, Rh or Raney's nickel.
Further improvements in methods as reducing aromatic hydrocarbon by indirect hydrogen transfer of the present invention: the hydrogen transference medium is carbazole or N-ethyl carbazole.
The method of reducing aromatic hydrocarbon by indirect hydrogen transfer of the present invention, use nontoxic carbazole or N-ethyl carbazole as the hydrogen transference medium, improves hydrogenation reaction speed, and the hydrogenation conditions milder, makes the more efficient and safety of hydrogenation process.
Embodiment
Embodiment 1: the reduction of benzene
Add benzene 3.9g (0.05mol), N-ethyl carbazole 2.5g (0.013mol) and Ru 0.2g in autoclave, fill hydrogen to pressure 0.4MPa, temperature is risen to 50 ℃, stirring reaction finished in 3 hours, cooling is driven still by distillation, obtains product hexanaphthene 4.1g, and yield is 98%.
N-ethyl carbazole 2.5g in Comparative Examples 1, cancellation embodiment 1, all the other obtain product hexanaphthene 2.7g fully with embodiment 1, and yield is 64%.
Embodiment 2: the reduction of toluene
Add toluene 4.6g (0.05mol), carbazole 2g (0.012mol) and Ru 0.2g in autoclave, fill hydrogen to pressure 0.2MPa, 75 ℃ of temperature of reaction, stirring reaction finished in 5 hours, cooling is driven still by distillation, and product methylcyclohexane 2.5g, yield are 51%.
Carbazole 2g in Comparative Examples 2, cancellation embodiment 2, all the other obtain product methylcyclohexane 0.8g fully with embodiment 2, and yield is 16%.
Embodiment 3: the reduction of toluene
Add toluene 4.6g (0.05mol), carbazole 2g (0.012mol) and Rh 0.2g in autoclave, fill hydrogen to pressure 1MPa, 60 ℃ of temperature of reaction, stirring reaction finished in 2 hours, cooling is driven still by distillation, and product methylcyclohexane 4.7g, yield are 96%.
Carbazole 2g in Comparative Examples 3, cancellation embodiment 3, all the other obtain product methylcyclohexane 3.4g fully with embodiment 3, and yield is 69%.
Embodiment 4: the reduction of ethylbenzene
Add ethylbenzene 5.3g (0.05mol), carbazole 2g (0.012mol) and Rh 0.2g in autoclave, fill hydrogen to pressure 1MPa, 60 ℃ of temperature of reaction, stirring reaction finished in 2 hours, cooling is driven still by distillation, and product ethylcyclohexane 5.4g, yield are 96%.
Carbazole 2g in Comparative Examples 4, cancellation embodiment 4, all the other obtain product ethylcyclohexane 3.0g fully with embodiment 4, and yield is 54%.
Embodiment 5: the reduction of naphthalene
Add naphthalene 6.4g (0.05mol), N-ethyl carbazole 2.5g (0.013mol) and Raney's nickel 0.3g in autoclave, fill hydrogen to pressure 2MPa, 120 ℃ of temperature of reaction, stirring reaction finished in 1.5 hours, cooling is driven still by underpressure distillation, and product perhydronaphthalene 6.7g, yield are 97%.
N-ethyl carbazole 2.5g in Comparative Examples 5, cancellation embodiment 5, all the other obtain product perhydronaphthalene 4.7g fully with embodiment 5, and yield is 68%.
Embodiment 6: the reduction of anthracene
Add anthracene 9.0g (0.05mol), N-ethyl carbazole 2.0g (0.01mol) and Rh 0.3g in autoclave, fill hydrogen to pressure 0.4MPa, 75 ℃ of temperature of reaction, stirring reaction finished in 5 hours, cooling is driven still by underpressure distillation, and product perhydroanthracene 9.2g, yield are 99%.
N-ethyl carbazole 2.0g in Comparative Examples 6, cancellation embodiment 6, all the other obtain product perhydroanthracene 6.8g fully with embodiment 6, and yield is 71%.
Embodiment 7: the reduction of biphenyl
Add biphenyl 7.7g (0.05mol), carbazole 2.0g (0.012mol) and Rh 0.3g in autoclave, fill hydrogen to pressure 1MPa, 75 ℃ of temperature of reaction, stirring reaction finished in 3 hours, cooling is driven still by underpressure distillation, and product bicyclohexane 7.6g, yield are 92%.
Carbazole 2.0g in Comparative Examples 7, cancellation embodiment 7, all the other obtain product bicyclohexane 5.6g fully with embodiment 7, and yield is 67%.
Embodiment 8: the reduction of BTX aromatics
Add benzene 3.9g (0.05mol), toluene 4.6g (0.05mol), naphthalene 6.4g (0.05mol), anthracene 9.0g (0.05mol), N-ethyl carbazole 4.0g (0.02mol) and Rh 0.5g in autoclave, fill hydrogen to pressure 2MPa, 150 ℃ of temperature of reaction, stirring reaction finished in 4 hours, cooling is driven still by underpressure distillation, product hexanaphthene 4.2g, yield are 99%; Methylcyclohexane 4.9g, yield are 99%; Perhydronaphthalene 6.8g, yield are 98%; Perhydroanthracene 9.5g, yield are 99%.
N-ethyl carbazole 4.0g in Comparative Examples 8, cancellation embodiment 8, all the other obtain product hexanaphthene 3.3g fully with embodiment 8, and yield is 78%; Methylcyclohexane 3.3g, yield are 68%; Perhydronaphthalene 5.2g, yield are 75%; Perhydroanthracene 6.7g, yield are 70%.
Embodiment 9: the reduction of BTX aromatics
Add benzene 3.9g (0.05mol), toluene 4.6g (0.05mol), naphthalene 6.4g (0.05mol), anthracene 9.0g (0.05mol), N-ethyl carbazole 4.0g (0.02mol) and Ru 0.5g in autoclave, fill hydrogen to pressure 3MPa, 80 ℃ of temperature of reaction, stirring reaction finished in 4 hours, cooling is driven still by underpressure distillation, product hexanaphthene 3.4g, yield are 80%; Methylcyclohexane 3.8g, yield are 78%; Perhydronaphthalene 5.0g, yield are 72%; Perhydroanthracene 7.9g, yield are 82%.
N-ethyl carbazole 4.0g in Comparative Examples 9, cancellation embodiment 9, all the other obtain product hexanaphthene 2.1g fully with embodiment 9, and yield is 50%; Methylcyclohexane 2.2g, yield are 45%; Perhydronaphthalene 3.9g, yield are 56%; Perhydroanthracene 5.2g, yield are 54%.
Embodiment 10: the reduction of naphthalene
Add naphthalene 6.4g (0.05mol), carbazole 2g (0.012mol) and Pt/C 0.5g (in this Pt/C, the weight content of Pt is 5%) in autoclave, fill hydrogen to pressure 2MPa, 120 ℃ of temperature of reaction, stirring reaction finished in 3 hours, cooling is driven still by underpressure distillation, product perhydronaphthalene 6.2g, yield are 90%.
Carbazole 2g in Comparative Examples 10, cancellation embodiment 10, all the other obtain product perhydronaphthalene 4.8g fully with embodiment 10, and yield is 70%.
The reduction of embodiment 11, naphthalene
Add naphthalene 6.4g (0.05mol), N-ethyl carbazole 2.5g (0.013mol) and Pd/C 0.5g (in this Pd/C, the weight content of Pd is 5%) in autoclave, fill hydrogen to pressure 2MPa, 120 ℃ of temperature of reaction, stirring reaction finished in 2.5 hours, cooling is driven still by underpressure distillation, product perhydronaphthalene 6.3g, yield are 92%.
N-ethyl carbazole 2.5g in Comparative Examples 11, cancellation embodiment 11, all the other obtain product perhydronaphthalene 4.5g fully with embodiment 11, and yield is 65%.
Finally, it is also to be noted that, what more than enumerate is only several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention, all should think protection scope of the present invention.
Claims (3)
1. the method for reducing aromatic hydrocarbon by indirect hydrogen transfer is characterized by: under the condition that catalyzer, hydrogen transference medium and hydrogen exist, aromatic hydrocarbon is reduced to alkane;
Described reduction reaction conditions is as follows:
The amount ratio of catalyzer and aromatic hydrocarbon is: 0.11 ~ 1g catalyzer/0.05mol aromatic hydrocarbon;
The amount ratio of hydrogen transference medium and aromatic hydrocarbon is: 0.005 ~ 0.05 mol hydrogen transference medium/0.05mol aromatic hydrocarbon;
Fill hydrogen to 0.2 ~ 4MPa, temperature of reaction is 50 ~ 180 ℃, and the reaction times is 1 ~ 7 hour;
Described catalyzer is Pt/C, Pd/C, Ru, Rh or Raney's nickel; In described Pt/C, the weight content of Pt is that the weight content of Pd in 5%, Pd/C is 5%;
Described hydrogen transference medium is carbazole or N-ethyl carbazole.
2. the method for reducing aromatic hydrocarbon by indirect hydrogen transfer according to claim 1 is characterized in that:
Described reduction reaction conditions is as follows:
The amount ratio of catalyzer and aromatic hydrocarbon is: 0.11 ~ 0.5g catalyzer/0.05mol aromatic hydrocarbon;
Hydrogen transference medium and aromatic hydrocarbon amount ratio be: 0.005 ~ 0.015 mol hydrogen transference medium/0.05mol aromatic hydrocarbon;
Fill hydrogen to 0.2 ~ 3MPa; Temperature of reaction is 50 ~ 150 ℃, and the reaction times is 1 ~ 5 hour.
3. the method for reducing aromatic hydrocarbon by indirect hydrogen transfer according to claim 1 and 2 is characterized in that:
Described aromatic hydrocarbon is at least a in benzene, toluene, ethylbenzene, dimethylbenzene, naphthalene, anthracene and biphenyl;
The alkane that benzene is reduced rear generation is hexanaphthene, the alkane that toluene is reduced rear generation is methylcyclohexane, the alkane that ethylbenzene is reduced rear generation is ethylcyclohexane, the alkane that dimethylbenzene is reduced rear generation is dimethyl cyclohexane, the alkane that naphthalene is reduced rear generation is perhydronaphthalene, the alkane that anthracene is reduced rear generation is perhydroanthracene, and the alkane that biphenyl is reduced rear generation is bicyclohexane.
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| CN102408291B true CN102408291B (en) | 2013-11-20 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3841698A1 (en) * | 1988-03-25 | 1989-10-12 | Henkel Kgaa | Hydrogenation catalyst and use thereof |
| CN1546442A (en) * | 2003-12-09 | 2004-11-17 | 南化集团研究院 | Method for synthesizing decahydronaphthalene |
| CN101575257A (en) * | 2009-06-16 | 2009-11-11 | 华东师范大学 | Catalytic hydrogenation method by taking toluene as hydrogen storing agent |
| CN101602644A (en) * | 2009-07-16 | 2009-12-16 | 厦门大学 | A kind of synthetic method of perhydronaphthalene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10050711A1 (en) * | 2000-10-13 | 2002-04-25 | Basf Ag | Hydrogenation of aromatic compounds to the corresponding cycloaliphatic comprises feeding reactants over fixed catalyst and removal of cycloaliphatic from side take off and/or column sump |
| US7101530B2 (en) * | 2003-05-06 | 2006-09-05 | Air Products And Chemicals, Inc. | Hydrogen storage by reversible hydrogenation of pi-conjugated substrates |
-
2011
- 2011-10-11 CN CN2011103066469A patent/CN102408291B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3841698A1 (en) * | 1988-03-25 | 1989-10-12 | Henkel Kgaa | Hydrogenation catalyst and use thereof |
| CN1546442A (en) * | 2003-12-09 | 2004-11-17 | 南化集团研究院 | Method for synthesizing decahydronaphthalene |
| CN101575257A (en) * | 2009-06-16 | 2009-11-11 | 华东师范大学 | Catalytic hydrogenation method by taking toluene as hydrogen storing agent |
| CN101602644A (en) * | 2009-07-16 | 2009-12-16 | 厦门大学 | A kind of synthetic method of perhydronaphthalene |
Non-Patent Citations (4)
| Title |
|---|
| Audrey Nowicki等.Nanoheterogeneous Catalytic Hydrogenation of Arenes:Evaluation of the Surfactant-Stabilized Aqueous Ruthenium(0)Colloidal Suspension.《Adv.Synth.Catal.》.2007,第349卷第2326-2330页. |
| Bastien Leger等.Imidazolium-functionalized bipyridine derivatives:a promising family of ligands for catalytical Rh(0)colloids.《Tetrahedron Letters》.2009,第50卷第6531-6533页. |
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| Nanoheterogeneous Catalytic Hydrogenation of Arenes:Evaluation of the Surfactant-Stabilized Aqueous Ruthenium(0)Colloidal Suspension;Audrey Nowicki等;《Adv.Synth.Catal.》;20071231;第349卷;第2326-2330页 * |
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