CN115947660A - Preparation method of high-purity dimethyl cyclohexylamine - Google Patents
Preparation method of high-purity dimethyl cyclohexylamine Download PDFInfo
- Publication number
- CN115947660A CN115947660A CN202211635766.8A CN202211635766A CN115947660A CN 115947660 A CN115947660 A CN 115947660A CN 202211635766 A CN202211635766 A CN 202211635766A CN 115947660 A CN115947660 A CN 115947660A
- Authority
- CN
- China
- Prior art keywords
- dimethylcyclohexylamine
- purity
- catalyst
- percent
- hydrogen
- 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.)
- Pending
Links
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 32
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000005070 sampling Methods 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims abstract description 10
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims abstract description 10
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 238000005086 pumping Methods 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 239000012752 auxiliary agent Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- OCDXZFSOHJRGIL-UHFFFAOYSA-N cyclohexyloxycyclohexane Chemical compound C1CCCCC1OC1CCCCC1 OCDXZFSOHJRGIL-UHFFFAOYSA-N 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
The invention relates to the technical field of organic synthesis, and discloses a preparation method of high-purity dimethyl cyclohexylamine, which comprises the following steps: adding a catalyst and cyclohexanone into a reactor, replacing the reactants for three times by nitrogen and hydrogen, introducing dimethylamine with a technical amount, carrying out a hydrogen pressure reaction, adding a small amount of formaldehyde after hydrogen is not taken basically, and continuing the reaction until the raw material is less than 0.05 percent and the N-methylcyclohexylamine is less than 0.02 percent; after the product is qualified, filtering to remove the catalyst, and removing ammonia and water; then rectifying, adding a small amount of phosphoric acid before rectifying, fully refluxing for 2-3h, sampling and analyzing, wherein the cyclohexanol content is less than 0.02%, and then rectifying normally to obtain the high-content N, N-dimethylcyclohexylamine with the content of more than 99.9%. According to the invention, a small amount of auxiliary agent is added to the existing production device of N, N-dimethylcyclohexylamine, so that high-purity N, N-dimethylcyclohexylamine meeting the requirements of customers is produced, and the method is simple to operate, and meets the use requirements without increasing investment.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of high-purity dimethyl cyclohexylamine.
Background
N, N-dimethylcyclohexylamine, english: n, N-dimethylcyclohexylamide, formula: C8H17N, CAS number 98-94-2;
the N, N-dimethylcyclohexylamine is mainly used in polyurethane catalyst industry, is a low-viscosity medium-activity amine catalyst, has catalytic action on gel and foaming, can provide relatively balanced catalytic performance for foaming reaction and gel reaction of hard foam, and is mainly used as a gel catalyst. At present, the material is applied to more materials and plate materials of refrigerators;
with the development of the polyurethane industry and the extension of the field, particularly the popularization and application in the automobile field, the quality requirement of customers on the polyurethane catalyst is higher and higher, with the development of the polyurethane industry, 99.9% of products are needed, and through normal rectification, the impurities of N-methylcyclohexylamine and cyclohexanol cannot be removed, and the requirements cannot be met.
Disclosure of Invention
The invention aims to provide a preparation method of high-purity dimethylcyclohexylamine, which aims to solve the problem that in the prior art, a crude product of the preparation method of N, N-dimethylcyclohexylamine by hydrogenating cyclohexanone and dimethylamine generally contains about 0.2 percent of N-methylcyclohexylamine (boiling point 149 ℃), about 0.2 percent of cyclohexanol (boiling point 160 ℃), about 160 ℃ of N, N-dimethylcyclohexylamine and cannot be removed by a conventional rectification method to obtain the high-purity N, N-dimethylcyclohexylamine of more than 99.9 percent.
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of high-purity dimethylcyclohexylamine is characterized by comprising the following steps:
step (1): adding a catalyst and cyclohexanone into a reactor, performing nitrogen replacement and hydrogen replacement for three times respectively, introducing dimethylamine with a technical amount, heating to 70-100 ℃, starting introducing hydrogen, controlling the pressure to be 3.0-3.5MPa, and reacting at the temperature of 140-150 ℃;
step (2): pumping water formaldehyde after hydrogen is eaten and slowed down, maintaining the pressure at 3.0-3.5MPa and the temperature at 140-150 ℃ for reaction, sampling until no hydrogen is eaten, judging that the raw material cyclohexanone is less than 0.05 percent and the N-methylcyclohexylamine is qualified when the raw material cyclohexanone is less than 0.02 percent, and keeping the temperature until the raw material cyclohexanone is qualified otherwise;
and (3): filtering the catalyst after the catalyst is qualified, heating the mother liquor to remove excessive dimethylamine, separating generated water, and then adding phosphoric acid;
and (4): the system is refluxed for 2 to 3 hours under normal pressure, then sampling and analyzing are carried out, cyclohexanol is qualified when the content is less than 0.02 percent, and the rectification is continued to obtain high-purity N, N-dimethyl cyclohexylamine with the content of more than 99.9 percent.
Preferably, the mass of the water formaldehyde accounts for 0.1-1% of the total weight of the cyclohexanone and the dimethylamine.
Preferably, the catalyst is one or a mixture of more of palladium carbon, platinum carbon, palladium aluminum catalyst and palladium calcium carbonate catalyst.
Preferably, the phosphoric acid is one or two of phosphoric acid, phosphorous acid and metaphosphoric acid.
Preferably, the phosphorus-containing acid accounts for 0.01-0.1% of the mass ratio of the materials after water separation.
Preferably, after amine removal and water separation by using the existing distillation device, acid is added for refluxing for 2-3h under normal pressure at the temperature of 155-165 ℃.
The preparation method of the high-purity dimethyl cyclohexylamine has the beneficial effects that:
1. according to the invention, N-methyl cyclohexylamine is converted into N, N-dimethyl cyclohexylamine by adding water formaldehyde, and in addition, a trace amount of phosphorus-containing acid is added, so that cyclohexanol molecules can be dehydrated to generate high-boiling-point dicyclohexyl ether (the boiling point is 242.5 ℃) through reflux, and the aim of removing the cyclohexanol molecules through rectification is fulfilled;
2. according to the invention, a small amount of auxiliary agent is added to the existing production device of the N, N-dimethylcyclohexylamine, so that the high-purity N, N-dimethylcyclohexylamine meeting the customer requirements is produced, and the method has the advantages of simple operation and capability of meeting the use requirements under the condition of not increasing the investment.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a technical scheme that: a preparation method of high-purity dimethyl cyclohexylamine comprises the following reaction formula:
example 1:
s1, adding 4Kg of palladium carbon and 1600Kg of cyclohexanone into a reactor, replacing nitrogen and hydrogen for at least three times, introducing 955Kg of dimethylamine, starting stirring, heating to 80 ℃, introducing hydrogen, controlling the pressure to be 3.4-3.5MPa, the temperature to be 145-150 ℃, pumping 5Kg of 37% water formaldehyde after hydrogen feeding is slowed down, continuing heat preservation and pressure maintaining reaction until hydrogen is not fed basically, sampling and analyzing, wherein the raw material cyclohexanone: 0.032%, N-methylcyclohexylamine: 0.012 percent. Cooling the material to 60 ℃, filtering, removing the excessive dimethylamine from the mother liquor in an amine-removing and water-separating kettle, and then separating the lower-layer water;
s2, adding 0.4kg of phosphoric acid into the upper-layer material, heating to about 160 ℃, keeping total reflux for 2 hours, sampling and analyzing, wherein cyclohexanol: 0.012%, then rectified to give 2050kg of 99.92% N, N-dimethylcyclohexylamine with a yield of 98.9%.
Example 2:
s1, adding 6Kg of palladium calcium carbonate and 1600Kg of cyclohexanone into a reactor, replacing nitrogen and hydrogen for at least three times, introducing 1000Kg of dimethylamine, starting stirring, heating to 80 ℃, introducing hydrogen, controlling the pressure to be 3.4-3.5MPa, the temperature to be 145-150 ℃, pumping 3Kg of water formaldehyde with the concentration of 37% after the hydrogen consumption is slowed down, continuing the heat preservation and pressure maintaining reaction until the hydrogen consumption is basically avoided, sampling and analyzing, wherein the raw material cyclohexanone: 0.023%, N-methylcyclohexylamine: 0.015 percent. Cooling the material to 60 ℃, filtering, removing the excessive dimethylamine from the mother liquor in an amine-removing and water-separating kettle, and then separating the lower-layer water;
s2, adding 0.2kg of phosphorous acid into the upper-layer material, heating to about 160 ℃, keeping total reflux for 2h, sampling and analyzing, wherein cyclohexanol: 0.011 percent, then rectifying to obtain 2040kg99.94 percent of N, N-dimethylcyclohexylamine, and the yield is 98.4 percent.
Example 3:
s1, adding 6Kg of platinum carbon and 1600Kg of cyclohexanone into a reactor, replacing nitrogen and hydrogen for at least three times, introducing 920Kg of dimethylamine, starting stirring, heating to 80 ℃, introducing hydrogen, controlling the pressure to be 3.0-3.1MPa, the temperature to be 130-140 ℃, pumping 10Kg of 37% water formaldehyde after hydrogen feeding is slowed down, carrying out heat preservation and pressure maintaining reaction until hydrogen is not fed basically, sampling and analyzing, wherein the raw material cyclohexanone: 0.03%, N-methylcyclohexylamine: 0.01 percent. Cooling the material to 60 ℃, filtering, removing the mother liquor in a deamination water diversion kettle, removing redundant dimethylamine, and then dividing the lower-layer water;
s2, adding 0.3kg of metaphosphoric acid into the upper layer material, heating to about 160 ℃, keeping total reflux for 2h, sampling and analyzing, wherein cyclohexanol: 0.014 percent, and then rectifying to obtain 2052kg99.92 percent of N, N-dimethylcyclohexylamine with the yield of 99 percent.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. A preparation method of high-purity dimethylcyclohexylamine is characterized by comprising the following steps:
step (1): adding a catalyst and cyclohexanone into a reactor, performing nitrogen replacement and hydrogen replacement for three times respectively, introducing dimethylamine with a technological quantity, heating to 70-100 ℃, starting introducing hydrogen, controlling the pressure to be 3.0-3.5MPa, and reacting at the temperature of 140-150 ℃;
step (2): pumping water formaldehyde after hydrogen feeding is slowed down, maintaining the pressure at 3.0-3.5MPa, reacting at the temperature of 140-150 ℃, sampling until no hydrogen is fed, wherein the raw materials of cyclohexanone is less than 0.05 percent and N-methyl cyclohexylamine is qualified when the content of N-methyl cyclohexylamine is less than 0.02 percent, and otherwise, continuously preserving the heat until the raw materials are qualified;
and (3): filtering the catalyst after the catalyst is qualified, heating the mother liquor to remove excessive dimethylamine, separating generated water, and then adding phosphoric acid;
and (4): the system is refluxed for 2 to 3 hours under normal pressure, then sampling and analyzing are carried out, the cyclohexanol is qualified when the content is less than 0.02 percent, and the rectification is continued to obtain the high-purity N, N-dimethyl cyclohexylamine with the content of more than 99.9 percent.
2. The method for preparing high-purity dimethylcyclohexylamine according to claim 1, characterized in that: the mass of the water formaldehyde accounts for 0.1-1% of the total weight of the cyclohexanone and the dimethylamine.
3. The method for preparing high-purity dimethylcyclohexylamine according to claim 1, characterized in that: the catalyst is one or a mixture of more of palladium carbon, platinum carbon, palladium aluminum catalyst and palladium calcium carbonate catalyst.
4. The method for preparing high-purity dimethylcyclohexylamine according to claim 1, characterized in that: the phosphoric acid is one or two of phosphoric acid, phosphorous acid and metaphosphoric acid.
5. The method for preparing high-purity dimethylcyclohexylamine according to claim 1, characterized in that: the phosphorus-containing acid accounts for 0.01-0.1% of the mass ratio of the materials after water diversion.
6. The method for preparing high-purity dimethylcyclohexylamine according to claim 1, characterized in that: after amine removal and water separation by using the existing distillation device, adding acid and refluxing for 2-3h at normal pressure at the temperature of 155-165 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211635766.8A CN115947660A (en) | 2022-12-19 | 2022-12-19 | Preparation method of high-purity dimethyl cyclohexylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211635766.8A CN115947660A (en) | 2022-12-19 | 2022-12-19 | Preparation method of high-purity dimethyl cyclohexylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115947660A true CN115947660A (en) | 2023-04-11 |
Family
ID=87290124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211635766.8A Pending CN115947660A (en) | 2022-12-19 | 2022-12-19 | Preparation method of high-purity dimethyl cyclohexylamine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115947660A (en) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873621A (en) * | 1972-05-22 | 1975-03-25 | Univ Minnesota | Method for preparing amines |
| CN1092061A (en) * | 1993-03-10 | 1994-09-14 | 金坛县助剂厂 | N, the production method of N-dimethyl cyclohexylamine catalyst |
| CN1990456A (en) * | 2005-12-28 | 2007-07-04 | 张炳庚 | Novel method for producing N, N-dimethyl cyclohexylamine |
| CN101619026A (en) * | 2009-07-29 | 2010-01-06 | 浙江新化化工股份有限公司 | Synthesis method for continuously producing N,N-dimethyl cyclohexyl amine |
| CN104892429A (en) * | 2015-04-10 | 2015-09-09 | 万华化学集团股份有限公司 | Method for preparing N,N-dimethylcyclohexylamine and N-methyl-dicyclohexylamine |
| CN109608340A (en) * | 2018-12-18 | 2019-04-12 | 江苏万盛大伟化学有限公司 | The preparation method of N, N- dimethyl cyclohexyl amine |
| CN111333520A (en) * | 2020-03-09 | 2020-06-26 | 万华化学集团股份有限公司 | Method for preparing N, N-dimethyl cyclohexylamine |
| CN114031504A (en) * | 2021-11-12 | 2022-02-11 | 山东中科新材料研究院有限公司 | Method for preparing N, N-dimethyl cyclohexylamine |
-
2022
- 2022-12-19 CN CN202211635766.8A patent/CN115947660A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873621A (en) * | 1972-05-22 | 1975-03-25 | Univ Minnesota | Method for preparing amines |
| CN1092061A (en) * | 1993-03-10 | 1994-09-14 | 金坛县助剂厂 | N, the production method of N-dimethyl cyclohexylamine catalyst |
| CN1990456A (en) * | 2005-12-28 | 2007-07-04 | 张炳庚 | Novel method for producing N, N-dimethyl cyclohexylamine |
| CN101619026A (en) * | 2009-07-29 | 2010-01-06 | 浙江新化化工股份有限公司 | Synthesis method for continuously producing N,N-dimethyl cyclohexyl amine |
| CN104892429A (en) * | 2015-04-10 | 2015-09-09 | 万华化学集团股份有限公司 | Method for preparing N,N-dimethylcyclohexylamine and N-methyl-dicyclohexylamine |
| CN109608340A (en) * | 2018-12-18 | 2019-04-12 | 江苏万盛大伟化学有限公司 | The preparation method of N, N- dimethyl cyclohexyl amine |
| CN111333520A (en) * | 2020-03-09 | 2020-06-26 | 万华化学集团股份有限公司 | Method for preparing N, N-dimethyl cyclohexylamine |
| CN114031504A (en) * | 2021-11-12 | 2022-02-11 | 山东中科新材料研究院有限公司 | Method for preparing N, N-dimethyl cyclohexylamine |
Non-Patent Citations (1)
| Title |
|---|
| 韩广甸: "《有机制备化学手册》", pages: 255 - 257 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111454159B (en) | Preparation process method of N-methyl-1, 3-propanediamine | |
| CN106554286B (en) | A kind of method that noble metal catalyst continuously prepares p phenylenediamine type antioxidant | |
| CN107827756A (en) | A kind of preparation method and device and catalyst of the diphenylmethane series diamines and polyamines of low N methyl impurity content | |
| CN109180428B (en) | Production process of 2, 2-dimethyl-1, 3-propylene glycol | |
| CN115947660A (en) | Preparation method of high-purity dimethyl cyclohexylamine | |
| CN112250534B (en) | Method for reducing unit consumption of cumene in process of producing epoxypropane by cumene co-oxidation method | |
| CN112300029B (en) | Preparation method of 3-hydroxypropionitrile | |
| CN102070464B (en) | Method for producing phenylene diamine by performing hydrogenation reduction on mixed dinitrobenzene with palladium catalyst | |
| WO2016091058A1 (en) | Method for preparing 3-pentanone from 2-pentene | |
| CN112745196B (en) | Method and device for preparing methyl isobutyl ketone and isopropanol from acetone | |
| CN115197048A (en) | Preparation method of hydrogenated bisphenol A | |
| CN110156026B (en) | Purification process of polycrystalline silicon raw material | |
| CN110627651B (en) | Method for reducing phenol content in aniline | |
| CN116023234B (en) | Continuous production process of hydrogenated bisphenol A | |
| US2944087A (en) | Alcohol hydrofinishing | |
| CN109503398B (en) | Preparation method of N-methyl-4-methoxyaniline | |
| CN109535007A (en) | A kind of diamino-dicyclohexyl methane isomer separation method | |
| JP2002128716A (en) | Method for producing isopropyl alcohol | |
| CN115925560B (en) | Preparation method of 4,4' -diaminodiphenyl ether | |
| CN115010694B (en) | Fluoroethylene carbonate and preparation method thereof | |
| CN114516802B (en) | Method for refining toluenediamine | |
| CN113943223B (en) | Method for preparing aniline by liquid phase hydrogenation of nitrobenzene with low phenol yield | |
| CN101475434B (en) | Toluene disproportionation process for producing high-purity benzene | |
| CN117843448A (en) | Preparation method for safely and efficiently synthesizing isooctyl alcohol | |
| CN116835530A (en) | Method and device for recovering excessive hydrogen chloride in chloromethane synthesis by liquid phase catalysis method |
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 |