CN109942444A - A method of it prepares trans- to aminocyclohexanol - Google Patents
A method of it prepares trans- to aminocyclohexanol Download PDFInfo
- Publication number
- CN109942444A CN109942444A CN201910297071.5A CN201910297071A CN109942444A CN 109942444 A CN109942444 A CN 109942444A CN 201910297071 A CN201910297071 A CN 201910297071A CN 109942444 A CN109942444 A CN 109942444A
- Authority
- CN
- China
- Prior art keywords
- trans
- aminocyclohexanol
- preparing
- reaction
- aminophenol
- 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.)
- Granted
Links
- PVBLJPCMWKGTOH-UHFFFAOYSA-N 1-aminocyclohexan-1-ol Chemical compound NC1(O)CCCCC1 PVBLJPCMWKGTOH-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 23
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 7
- 230000000996 additive effect Effects 0.000 claims abstract description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000003863 metallic catalyst Substances 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 10
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000012805 post-processing Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 13
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000012797 qualification Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- -1 aminocyclohexyl Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 description 1
- 229960005174 ambroxol Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The trans- method to aminocyclohexanol is prepared the invention discloses a kind of, using para-aminophenol as raw material metallic catalyst is added, using carbonate or sulfate as additive in this method, in ketones solvent it is hydrogenated reaction obtain to aminocyclohexanol, then it is post-treated obtain it is trans- to aminocyclohexanol.Present invention employs relatively inexpensive para-aminophenol to reduce production cost instead of more expensive acetaminophenol, economic benefit is improved, and through experimental exploring, it is found that preparation process reaction is relatively gentle, reaction temperature and reaction pressure are greatly reduced, and convenient for operation, are suitble to industrialized production.Products obtained therefrom yield is reacted up to 80-90%, and trans- high to aminocyclohexanol ratio, environmental pollution is small.
Description
Technical field
The present invention relates to a kind of preparation method of compound, the specifically trans- preparation method to aminocyclohexanol belongs to
Chemosynthesis technical field.
Background technique
Trans- is white or off-white color crystalline powder to aminocyclohexanol；The light-exposed or long color of storage can deepen.It can be molten
In organic solvents such as chloroforms.It is the important source material of synthetic hydrochloric acid ambroxol.It is trans- to aminocyclohexanol main preparation methods:
1, acetaminophenol method.Such as Tang Xinyuan in 2005, Zhejiang University in 2015, it is anti-that Yang Jian etc. is all made of the synthesis of this method
Formula is to aminocyclohexanol, and industrialized principal synthetic routes at present.The disadvantage is that it is relatively low along inverse proportion, although can repeat
It applies, but reaction pressure is very high, can arrive 9.0MPa, and complicated for operation, energy consumption is higher.
2, acetaminophenol method is improved.The technique of many scholar's acamol methods was improved later, main
Want it is improved be hydrogenation catalyst and plus hydrogen solvent, reduce reaction pressure, improve along inverse proportion, mentioned by original 60%
Height is to 80% or so.The disadvantage is that the advantage of this route is smaller and smaller with the rise in price of acetaminophenol, cost pressure
Power is larger.
Summary of the invention
It is good that the technical problem to be solved by the invention is to provide a kind of safeties, and at low cost preparing is trans- to amino ring
The method of hexanol.
In order to solve the above technical problems, of the present invention prepare the trans- method to aminocyclohexanol, with para-aminophenol
For raw material, metallic catalyst is added, using carbonate or sulfate as additive, hydrogenated reaction is obtained to ammonia in ketones solvent
Cyclohexanol, along inverse proportion in 1:5-10, then crystallized processing obtain it is trans- to the higher crude product of aminocyclohexanol accounting, crude product
Fine work is obtained with acetone recrystallization, for the trans- to aminocyclohexanol of qualification.
Reaction equation:
The hydrogenation carries out in autoclave, and filling with inert gas is protected.
Further, the hydrogenation reaction temperature is 20-150 DEG C, reaction pressure 0.1-2.0MPa.
Further, the reaction pressure is 1.0-1.2MPa.
Further, in 0-10 DEG C of crystallization reaction 1-2h after hydrogenation.
Further, the additive is the carbonate or sulfate of sodium or potassium, such as potassium carbonate (sodium), saleratus
(sodium), sodium sulphate (potassium), sodium bisulfate (potassium), sodium hydrogensulfite (potassium).
Further, the metallic catalyst is Raney's nickel, platinum carbon or palladium-carbon catalyst.
Further, the mole dosage ratio of the para-aminophenol, additive and catalyst is 1:0.01-1:0.0001-
0.1。
Further, the ketones solvent is acetone, diacetone alcohol or methyl iso-butyl ketone (MIBK).
Further, the ketones solvent is acetone.
Present invention employs relatively inexpensive para-aminophenol to reduce and be produced into instead of more expensive acetaminophenol
This, improves economic benefit, and through experimental exploring, it is found that the preparation process reacts relatively gentle, reaction temperature and reaction pressure
It is greatly reduced, convenient for operation, is suitble to industrialized production.Reaction products obtained therefrom yield is trans- to aminocyclohexanol up to 80-90%
Ratio is high, and environmental pollution is small.
Specific embodiment
Below with reference to embodiment, more specifically the elaboration contents of the present invention.Implementation of the invention is not limited to following reality
Example is applied, the accommodation in any form made to the present invention or changed all should be within the scope of the present invention.
Embodiment 1: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of addition 54.5g (0.5mol), potassium carbonate 7g (0.05mol), 5%
Palladium carbon 0.5g (0.00023mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, is passed through hydrogen, makes
Pressure is maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Under catalyst returns in autoclave
It criticizes and continues to use.Crude product obtains the trans- to aminocyclohexanol 51g, yield of qualification with the acetone recrystallization of 2 times of weight after filtering
90%.
Embodiment 2: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of 54.5g (0.5mol), sodium carbonate 7g (0.066mol), thunder is added
Buddhist nun's nickel 1g (0.017mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, is passed through hydrogen, makes pressure
It is maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Catalyst back to lower batch in autoclave after
It is continuous to use.Crude product obtains the trans- to aminocyclohexanol 50g, yield 87% of qualification with the acetone recrystallization of 2 times of weight after filtering.
Embodiment 3: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of addition 54.5g (0.5mol), saleratus 7g (0.07mol),
Raney's nickel 1g (0.017mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, is passed through hydrogen, makes to press
Power is maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Catalyst is back to lower batch in autoclave
It continues to use.Crude product obtains the trans- to aminocyclohexanol 50.6g, yield of qualification with the acetone recrystallization of 2 times of weight after filtering
88%.
Embodiment 4: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of addition 54.5g (0.5mol), potassium sulfate 10g (0.057mol),
Raney's nickel 1g (0.017mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, is passed through hydrogen, makes to press
Power is maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Catalyst is back to lower batch in autoclave
It continues to use.Crude product obtains the trans- to aminocyclohexanol 48g, yield of qualification with the acetone recrystallization of 2 times of weight after filtering
83.5%.
Embodiment 5: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of 54.5g (0.5mol), potassium acid sulfate 10g is added
(0.073mol), Raney's nickel 1g (0.017mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, leads to
Enter hydrogen, pressure is made to be maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Catalyst returns to
Lower batch continues to use in autoclave.Crude product obtains the trans- to aminocyclohexyl of qualification with the acetone recrystallization of 2 times of weight after filtering
Alcohol 6.5g, yield 81%.
Embodiment 6: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of 54.5g (0.5mol), sodium sulphate 10g (0.07mol), thunder is added
Buddhist nun's nickel 1g (0.017mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, is passed through hydrogen, makes pressure
It is maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Catalyst back to lower batch in autoclave after
It is continuous to use.Crude product obtains the trans- to aminocyclohexanol 46g, yield 80% of qualification with the acetone recrystallization of 2 times of weight after filtering.
Embodiment 7: the trans- preparation to aminocyclohexanol
In the reaction kettle of 500mL, the para-aminophenol of 54.5g (0.5mol), sodium sulfite 10g is added
(0.079mol), Raney's nickel 1g (0.017mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, leads to
Enter hydrogen, pressure is made to be maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Catalyst returns to
Lower batch continues to use in autoclave.Crude product obtains the trans- to aminocyclohexyl of qualification with the acetone recrystallization of 2 times of weight after filtering
Alcohol 47.7g, yield 83%.
Embodiment 8: the trans- preparation to aminocyclohexanol.
In the reaction kettle of 500mL, the para-aminophenol of addition 54.5g (0.5mol), potassium carbonate 7g (0.05mol), 5%
Platinum carbon 0.5g (0.00013mol), acetone 150mL, after charging, nitrogen charging gas shielded is warming up to 100 DEG C, is passed through hydrogen, makes
Pressure is maintained at 1.0-1.2MPa, keeps the temperature 7h.After cooling to 10 DEG C, filtering, filtrate crystallisation.Under catalyst returns in autoclave
It criticizes and continues to use.Crude product obtains the trans- to aminocyclohexanol 51g, yield of qualification with the acetone recrystallization of 2 times of weight after filtering
90%.
Claims (10)
1. a kind of prepare the trans- method to aminocyclohexanol, it is characterised in that: this method is added using para-aminophenol as raw material
Metallic catalyst, using carbonate or sulfate as additive, hydrogenated reaction is obtained to aminocyclohexanol in ketones solvent, then
It is post-treated obtain it is trans- to aminocyclohexanol.
2. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: the hydrogenation reaction temperature
It is 20-150 DEG C, reaction pressure 0.1-2.0MPa.
3. preparing the trans- method to aminocyclohexanol according to claim 2, it is characterised in that: the reaction pressure is
1.0-1.2MPa。
4. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: after hydrogenation
0-10 DEG C of crystallization reaction 1-2h.
5. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: the additive be sodium or
The carbonate or sulfate of potassium.
6. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: the metallic catalyst is
Raney's nickel, platinum carbon or palladium-carbon catalyst.
7. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: the para-aminophenol,
The mole dosage of additive and catalyst ratio is 1:0.01-1:0.0001-0.1.
8. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: the ketones solvent is third
Ketone, diacetone alcohol or methyl iso-butyl ketone (MIBK).
9. preparing the trans- method to aminocyclohexanol according to claim 1 or 8, it is characterised in that: the ketones solvent
For acetone.
10. preparing the trans- method to aminocyclohexanol according to claim 1, it is characterised in that: the post-processing includes
Solution after reaction is crystallized to be obtained trans- to aminocyclohexanol crude product, and crude product be recrystallized to give with acetone trans- again
To aminocyclohexanol fine work.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910297071.5A CN109942444B (en) | 2019-04-15 | 2019-04-15 | Method for preparing trans-p-aminocyclohexanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910297071.5A CN109942444B (en) | 2019-04-15 | 2019-04-15 | Method for preparing trans-p-aminocyclohexanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109942444A true CN109942444A (en) | 2019-06-28 |
| CN109942444B CN109942444B (en) | 2021-11-26 |
Family
ID=67015070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910297071.5A Active CN109942444B (en) | 2019-04-15 | 2019-04-15 | Method for preparing trans-p-aminocyclohexanol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109942444B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114436865A (en) * | 2022-02-16 | 2022-05-06 | 浙江清和新材料科技有限公司 | Preparation method of 4-aminocyclohexanol |
| CN114436865B (en) * | 2022-02-16 | 2024-05-24 | 浙江清和新材料科技有限公司 | Preparation method of 4-aminocyclohexanol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB454042A (en) * | 1935-05-30 | 1936-09-23 | Chem Ind Basel | Manufacture of hydroaromatic amino-alcohols and derivatives thereof |
| EP0909753A2 (en) * | 1997-10-15 | 1999-04-21 | Great Lakes Chemical Konstanz GmbH | Process for the preparation of trans-4-aminocyclohexanol |
| CN104447209A (en) * | 2014-11-19 | 2015-03-25 | 浙江大学 | Method for preparing cyclohexanol by catalyzing by base metal catalyst |
-
2019
- 2019-04-15 CN CN201910297071.5A patent/CN109942444B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB454042A (en) * | 1935-05-30 | 1936-09-23 | Chem Ind Basel | Manufacture of hydroaromatic amino-alcohols and derivatives thereof |
| EP0909753A2 (en) * | 1997-10-15 | 1999-04-21 | Great Lakes Chemical Konstanz GmbH | Process for the preparation of trans-4-aminocyclohexanol |
| CN104447209A (en) * | 2014-11-19 | 2015-03-25 | 浙江大学 | Method for preparing cyclohexanol by catalyzing by base metal catalyst |
Non-Patent Citations (4)
| Title |
|---|
| HUAIFENG LI等: "Selective Catalytic Hydrogenation of Arenols by a Well-Defined Complex of Ruthenium and Phosphorus−Nitrogen PN3−Pincer Ligand Containing a Phenanthroline Backbone", 《ACS CATAL.》 * |
| J.R.SCHAEFGEN等: "Interfacial Polycondensation. VIII. Application to A-B-Type Monomers", 《JOURNAL OF POLYMER SCIENCE》 * |
| 唐新元: "反式-4-氨基环己醇的研究开发", 《杭州化工》 * |
| 杨能渭，徐正林: "4-乙酰氨基环己醇的顺反立体异构化工艺", 《高校化学工程学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114436865A (en) * | 2022-02-16 | 2022-05-06 | 浙江清和新材料科技有限公司 | Preparation method of 4-aminocyclohexanol |
| CN114436865B (en) * | 2022-02-16 | 2024-05-24 | 浙江清和新材料科技有限公司 | Preparation method of 4-aminocyclohexanol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109942444B (en) | 2021-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201918474A (en) | Method for preparing azoxystrobin intermediates | |
| CN101103725A (en) | Cartap environment-friendly type preparing method | |
| CN109776547A (en) | Preparation method of tofacitinib citrate | |
| CN113024385B (en) | Preparation method of 2,2 '-bis (trifluoromethyl) -4, 4' -diaminobiphenyl | |
| CN109942444A (en) | A method of it prepares trans- to aminocyclohexanol | |
| CN107973733B (en) | Method for preparing selenomethionine | |
| TW201130787A (en) | Process for preparing 2,2-difluoroethylamine and salts thereof proceeding from difluoroacetonitrile | |
| WO2023093677A1 (en) | Synthesis process for fatty acyl taurate | |
| CN107365251B (en) | Preparation method of cyclohexyl formic acid | |
| CN104628626A (en) | Preparation method of 2,2,6,6-tetramethyl-4-piperidinol | |
| CN108794468A (en) | A kind of preparation method of Tetrahydropyridoindocompounds compounds | |
| Cason | The Nitration of Melamine and of Triacetylmelamine1 | |
| CN111170932A (en) | Preparation method of 2-aminomethyl-5-trifluoromethyl pyridine salt | |
| CN109879775A (en) | A kind of environment-friendly preparation method of 5-ALA hydrochloride intermediate | |
| US3038007A (en) | Process for the preparation of dl-threonine | |
| CN107540548B (en) | Method for preparing dibutyl carbonate | |
| BG64948B1 (en) | Method for preparing polyhalogenated paratrifluoromethylanilines | |
| CN112851519A (en) | Synthesis method of N-methylisopropylamine | |
| CN109111371B (en) | Preparation method of hydrazino ethyl acetate hydrochloride | |
| CN103086894A (en) | Synthesis method of electroplating additive 3-methyl-3-aminobutyne | |
| CN109053563A (en) | A method of preparing hydrochloric acid Flupirtine | |
| CN103086945A (en) | Synthetic process of important pharmaceutical chemical intermediate tryptamine | |
| CN101412678A (en) | Method for synthesizing memantine hydrochloride | |
| CN101003488A (en) | Method for synthesizing natrium sarkosine from methyl - ethanolamine | |
| CN102260142A (en) | Method for preparing medicinal intermediate of 4-methylbenzhydrol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 317016 coastal industrial zone, Taizhou, Zhejiang, China Patentee after: Zhejiang Haizhou Pharmaceutical Co.,Ltd. Address before: 317016 coastal industrial zone, Taizhou, Zhejiang, China Patentee before: ZHEJIANG HAIZHOU PHARMACEUTICAL CO.,LTD. |