CN112341341A - Preparation method of N-ethylaniline - Google Patents
Preparation method of N-ethylaniline Download PDFInfo
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- CN112341341A CN112341341A CN202011103555.0A CN202011103555A CN112341341A CN 112341341 A CN112341341 A CN 112341341A CN 202011103555 A CN202011103555 A CN 202011103555A CN 112341341 A CN112341341 A CN 112341341A
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- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
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- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
- C07C1/323—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a nitrogen atom
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- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
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- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
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Abstract
The invention discloses a preparation method of N-ethylaniline, which comprises amino protection, low-pressure synthesis and post-treatment, wherein the processes are synergistically optimized, the ultrahigh selectivity of the N-ethylaniline is obtained under a mild reaction condition, and the high-yield and high-purity N-ethylaniline is finally obtained without generating the N, N-diethylaniline.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of N-ethylaniline.
Background
N-ethyl aniline is also called ethyl aniline, is yellow brown transparent oily liquid, has aniline smell and boiling point of 204 ℃, is insoluble in water and soluble in alcohol and most of organic solvents, is a very important chemical intermediate, is mainly used for organic synthesis, can be used as an intermediate of various dyes, and can also be used as a raw material of products such as pesticides, medicines, rubber auxiliaries, photosensitive materials and the like.
At present, aniline and ethanol are mainly used as starting materials in China, and N-ethylaniline is synthesized through nucleophilic reaction under an acid environment at high temperature and high pressure, but the reaction has some defects, firstly, the reaction conditions are high temperature and high pressure, the requirement on equipment is high, secondly, the reaction can only obtain a reaction mixture containing 20% of aniline, 65% -70% of N-ethylaniline and 10% -15% of diethylaniline, the reaction selectivity is poor, and the final yield and purity are poor. If alkyl halide, such as chloroethane and bromoethane, is directly used as raw material, the content of N, N-diethylaniline produced by reaction exceeds 30% (as shown in the patent technology with publication No. CN205838888U, the research results of "gas phase method for synthesizing N, N-diethylaniline" published by Zheng Hao et al in 2001, petrochemical, Vol.30, No. 11, etc. all show that the substitution reaction of alkyl halide and aniline is easier to produce N, N-diethylaniline), therefore, researchers are dedicated to search for a synthesis method with mild reaction conditions and better selectivity of N-ethylaniline.
Disclosure of Invention
Aiming at the technical problems and the defects in the field, the invention provides the preparation method of the N-ethylaniline, the BOC anhydride is used as the amino protective agent, the reaction condition of the BOC anhydride and the aniline is simple, the protected amino group can only be subjected to a single substitution reaction, and the BOC group is easy to remove in the post-treatment process to generate the isobutene which can be recycled. Chloroethane is selected as an alkylating reagent, the reaction condition is mild, the alkylation reaction can be carried out under lower pressure, and the processes of amino protection, low-pressure synthesis and post-treatment are synergistically optimized to realize the ultrahigh selectivity of the N-ethylaniline under the mild reaction condition, so that the high-yield and high-purity N-ethylaniline is finally obtained, and no N, N-diethylaniline is generated.
The process flow of the preparation method of N-ethylaniline is shown in figure 1.
A preparation method of N-ethylaniline comprises the following steps:
(1) adding an aniline aqueous solution into a reaction kettle, adding BOC acid anhydride serving as an amino protective agent, adding an acid binding agent, and reacting at 50-80 ℃ for amino protection, wherein the reaction formula is as follows:
(2) feeding chloroethane into the reaction kettle in batches for multiple times for alkylation reaction, heating to 80-100 ℃, and carrying out heat preservation reaction, wherein the reaction pressure is controlled to be 0.05-0.5 MPa, and the reaction formula is as follows:
(3) and (3) after the alkylation reaction is finished, discharging chloroethane gas in the reaction kettle, cooling and recovering the chloroethane gas for the step (2), standing and layering the obtained reaction liquid, using the lower-layer water phase as next batch of mother liquid water for reuse, adding hydrochloric acid into the upper-layer oil phase to remove BOC and collecting generated isobutene to obtain the product N-ethylaniline, wherein the reaction formula is as follows:
the feeding molar ratio of the aniline to the BOC anhydride to the chloroethane to the water to the acid-binding agent to the hydrochloric acid is 1: 0.5-0.6: 1-1.1: 15-20: 0.3-0.5: 1-1.1, wherein the feeding molar amount of the hydrochloric acid is calculated by HCl.
According to the preparation method, amino protection is firstly carried out, aniline aqueous solution, BOC acid anhydride and an acid-binding agent in a specific proportion are added into a reaction kettle, a specific amount of chloroethane is fed in batches for multiple times after the reaction is finished to carry out alkylation reaction, layering is carried out after the reaction is finished, a lower-layer water phase is recovered to carry out the next reaction, a specific amount of hydrochloric acid is added into an upper-layer oil phase to remove a protecting group, and N-ethylaniline is obtained. On the basis of the concept of amino protection-alkylation reaction-post treatment, the preparation method further optimizes the parameter conditions and the material adding proportion in each step, so that the N-ethylaniline can be synthesized at a lower temperature and a lower pressure, the reaction selectivity is high, the generation of the N, N-diethylaniline is completely avoided, the reaction process and the post treatment are simple, the requirement on equipment is lower, the utilization rate of raw materials and the product yield are improved, and the isobutene can be further recycled.
In addition, the acid-binding agent added in the step (1) can just remove HCl generated in the alkylation reaction process in the step (2), so that the reaction equilibrium is carried out in the positive reaction direction, and the purity and the yield of the N-ethylaniline are further improved.
In addition, the preparation method provided by the invention has the advantages that the selectivity of the N-ethylaniline is obviously improved, and the generation of the N, N-diethylaniline is completely avoided, so that the N-ethylaniline with high purity and high yield can be obtained under the condition that the molar ratio of the aniline to the chloroethane is 1: 1-1.1, and the dosage of the chloroethane is effectively saved. In addition, outside the above molar ratio range of aniline to ethyl chloride, an increase in the molar ratio results in a large amount of waste of raw materials and an incomplete reaction in which the molar ratio is decreased.
The acid-binding agent is preferably at least one of sodium carbonate, sodium bicarbonate and magnesium oxide.
In the step (1), the optimal molar ratio of the aniline to the BOC anhydride is 1: 0.5.
In the step (1), the acid-binding agent can be simultaneously added with the aniline aqueous solution at one time or added in batches for multiple times. Preferably, the acid-binding agent is added in 3 batches, the adding amount of each batch is 50%, 25% and 25% of the total adding amount of the acid-binding agent, the interval between the first batch and the second batch is 2 hours, and the interval between the second batch and the third batch is 1 hour.
Preferably, in the step (1), the stirring speed in the reaction kettle is 350rpm, and the reaction time is 5 hours.
In the preparation method, the chloroethane is fed in batches for multiple times, so that the chloroethane in a reaction system in the reaction kettle is always insufficient, the full implementation of alkylation reaction is facilitated, the selectivity of the N-ethylaniline is improved, the reaction pressure can be always kept mild and is between 0.05 and 0.5MPa, and the problem of rapid increase of the reaction pressure caused by one-time large-amount chloroethane feeding is avoided.
Preferably, the chloroethane is fed in 3 batches, the interval time between each batch is 30min, and the adding amount of each batch is 50%, 25% and 25% of the total adding amount of the chloroethane in sequence.
The invention carries out the reaction under lower reaction pressure, so the temperature is too low, the reaction time is too long, and the purity and the yield of the N-ethylaniline are reduced. Preferably, in the step (2), the reaction effect is best when the temperature is raised to 90-100 ℃.
Further, when the temperature is raised to 90-100 ℃ for heat preservation reaction, the optimal reaction time is 5-7 h, and the N-ethylaniline with extremely high purity and yield can be obtained. The reaction is incomplete in a shorter time, and the energy consumption is increased in a longer time.
In the step (3), the chloroethane gas in the reaction kettle can be collected by the low-temperature cooling medium for the alkylation of the next batch. Standing the reaction solution for layering to obtain the upper layer which is the semi-finished product of N-ethylaniline, adding hydrochloric acid to remove protecting group to obtain N-ethylaniline, introducing the generated gas into alkaline solution such as sodium hydroxide to remove CO2And collecting the isobutene.
Preferably, in the step (3), the HCl mass concentration in the hydrochloric acid is 37% to 40%.
Preferably, in the step (3), the reaction temperature for removing BOC is 50 ℃.
Preferably, the isobutene generated by collection is specifically: introducing gas generated by adding hydrochloric acid into the upper oil phase to remove BOC into sodium hydroxide solution to remove CO2To collect the abnormalButene.
Compared with the prior art, the invention has the main advantages that:
1) the invention adopts BOC to protect amino, inhibits the generation of N, N-diethylaniline and improves the reaction selectivity.
2) The invention ensures that the pressure and the temperature of the alkylation reaction are greatly reduced compared with the prior art by the amino protection treatment and the batch and multiple addition of the chloroethane in the first step, particularly compared with the reaction of aniline and ethanol, the reaction can be carried out at lower temperature and pressure, the safety of the reaction is improved, the requirement on equipment is low, the generated hydrochloric acid in the reaction process can be removed by an acid-binding agent, and the capability of corroding the equipment is reduced.
3) The method has the advantages of simple reaction process, no need of catalysis by a catalyst, high reaction selectivity, less side reaction, low environmental pollution and easy separation of reaction products.
4) The invention has simple post-treatment, unreacted raw materials (such as chloroethane) can be recycled, isobutene generated in the post-treatment process can be collected and utilized, and the aqueous solution can be recycled, thereby reducing the waste water amount and improving the utilization rate of the raw materials.
Drawings
FIG. 1 is a process flow diagram of the preparation method of the present invention.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The following examples are conducted under conditions not specified, usually according to conventional conditions, or according to conditions recommended by the manufacturer.
Comparative example 1
A preparation method of N-ethylaniline comprises the following specific steps:
(1) alkylation reaction
Adding 45g of aniline, 10g of sodium carbonate and 150g of water into a high-pressure reaction kettle, setting the stirring speed to be 350r/min, slowly heating to 90 ℃, introducing 33.7g of chloroethane, recording the highest pressure to be 0.6MPa, and carrying out heat preservation reaction for 5 hours. And (3) cooling and releasing pressure after the reaction is finished, discharging chloroethane gas in the system, cooling and recovering the chloroethane gas through a low-temperature refrigerant, and introducing the mixed material in the reaction kettle into a separating funnel, standing and layering to obtain a semi-finished product, wherein the aniline is 10%, the N-ethylaniline is 40%, and the N, N-diethylaniline is 35%.
(2) Post-treatment
And (2) carrying out reduced pressure distillation to recover aniline by adopting a steam distillation method, controlling the temperature to be 130-140 ℃ and the pressure to be-0.07-0.06 MPa, and obtaining a finished product after the distillation is finished, wherein the purity of the N-ethyl aniline is 50%, the N, N-diethyl aniline is 39%, the distilled liquid is added with chloride, the adding amount of the chloride is 1.5% of the mass of the distilled liquid, and an upper oil phase is recovered by layering and reused in an alkylation reaction.
Example 1
A preparation method of N-ethylaniline comprises the following specific steps:
(1) amino protection
Adding 45g of aniline, 20g of sodium carbonate, 52.7g of BOC anhydride (the molar ratio of the BOC anhydride to the aniline is 0.5:1) and 150g of water into a reaction kettle, setting the stirring speed to be 350r/min, slowly heating to 50 ℃, and reacting for 5 hours.
(2) Alkylation reaction
The reaction kettle is slowly heated to 90 ℃, 33.7g of chloroethane is added in 3 times (50% is added for the first time, 25% is added every 30 minutes, and the remaining 25% is added every 30 minutes), the recording pressure is 0.3MPa at most, and the reaction is kept for 6 hours. Cooling and releasing pressure after the reaction is finished, discharging chloroethane gas in the system, cooling and recovering the chloroethane gas through a low-temperature refrigerant, and introducing the mixed material in the reaction kettle into a separating funnel for standing and layering to obtain a semi-finished product.
(3) Post-treatment
Pouring the product obtained in the step 2 into a flask, adding 48g of 37 wt% hydrochloric acid, heating to 50 ℃ to remove BOC groups, and introducing the generated gas into 10 wt% sodium hydroxide solution to remove CO2Collecting isobutene, layering and collecting the upper oily matter to obtain the finished product N-ethylaniline with the purity of 98.5%.
Example 2
A preparation method of N-ethylaniline comprises the following specific steps:
(1) amino protection
Adding 45g of aniline, 52.7g of BOC anhydride (the molar ratio of the BOC anhydride to the aniline is 0.5:1), 20g of 50 wt% sodium carbonate solution and 150g of water into a reaction kettle, closing the reaction kettle, setting the stirring speed to be 350r/min, starting to slowly raise the temperature to 50 ℃ and reacting for 5 hours.
20g of 50% by weight sodium carbonate solution are added in 3 portions, 50% being added for the first time, 25% being added every 2 hours and the remaining 25% being added every 1 hour.
(2) Alkylation reaction
Slowly heating the reaction kettle to 90 ℃, adding 33.7g of chloroethane for 3 times (50% for the first time, 25% for every 30 minutes and the rest 25% for every 30 minutes), recording the pressure change pressure to be 0.3MPa at most, keeping the temperature for reaction for 6 hours, cooling after the reaction is finished, releasing the pressure to recover the unreacted chloroethane, introducing the mixed materials in the reaction kettle into a separating funnel, standing and layering to obtain a semi-finished product.
(3) Post-treatment
Pouring the semi-finished product into a flask, adding 48g of 37 wt% hydrochloric acid, heating to 50 ℃ to remove BOC groups, introducing the generated gas into 10 wt% sodium hydroxide solution to remove CO2Collecting isobutene, collecting upper layer oily matter in a layered mode to obtain the finished product N-ethylaniline, wherein the purity is 98.9%, and the result shows that the purity of the product is slightly better when the acid-binding agent is added in batches.
Comparative example 2
A preparation method of N-ethylaniline comprises the following specific steps:
(1) amino protection
Adding 45g of aniline, 20g of sodium carbonate, 35g of BOC anhydride and 150g of water into a reaction kettle, setting the stirring speed to be 350r/min, slowly heating to 50 ℃, and reacting for 5 hours.
(2) Alkylation reaction
Slowly heating to 90 ℃, adding 33.7g of chloroethane for 3 times (50% for the first time, 25% for every 30 minutes and the rest 25% for every 30 minutes), recording the highest pressure of 0.3MPa, keeping the temperature for reaction for 6 hours, cooling after the reaction is finished, releasing the pressure, discharging chloroethane gas in the system, cooling and recovering the chloroethane gas through a low-temperature refrigerant, introducing the mixed material in the reaction kettle into a separating funnel, standing and layering to obtain a semi-finished product.
(3) Post-treatment
Pouring the semi-finished product into a flask, adding 47g of 37 wt% hydrochloric acid, heating to 50 ℃ to remove BOC groups, introducing the generated gas into 10 wt% sodium hydroxide solution to remove CO2Collecting isobutene, layering and collecting the upper oily matter to obtain the finished product N-ethylaniline with the purity of 88 percent and the purity of 10 percent of N, N-diethylaniline. It is shown that the reduction of BOC anhydride results in incomplete aniline reaction and increased side reactions during alkylation.
Example 3
A preparation method of N-ethylaniline comprises the following specific steps:
(1) amino protection
Adding 45g of aniline, 20g of sodium bicarbonate, 52.7g of BOC anhydride (the molar ratio of the BOC anhydride to the aniline is 0.5:1) and 150g of water into a reaction kettle, setting the stirring speed to be 350r/min, slowly heating to 50 ℃, and reacting for 5 hours.
(2) Alkylation reaction
Slowly heating to 90 ℃, adding 33.7g of chloroethane in 3 times (50% for the first time, 25% for every 30 minutes and the rest 25% for every 30 minutes), recording the highest pressure of 0.3MPa, and keeping the temperature for reaction for 6 hours. Cooling and releasing pressure after the reaction is finished, and introducing the mixed materials in the reaction kettle into a separating funnel for standing and layering to obtain a semi-finished product.
(3) Post-treatment
Pouring the semi-finished product into a flask, adding 47g of 37 wt% hydrochloric acid, heating to 50 ℃ to remove BOC groups, introducing the generated gas into 10 wt% sodium hydroxide solution to remove CO2Collecting isobutene, and collecting upper oily matter layer by layer to obtain the finished product N-ethylaniline with the purity of 98%, which indicates that sodium bicarbonate is also feasible as an acid-binding agent.
Comparative example 3
A preparation method of N-ethylaniline comprises the following specific steps:
(1) amino protection
Adding 45g of aniline, 20g of sodium carbonate, 52.7g of BOC anhydride (the molar ratio of the BOC anhydride to the aniline is 0.5:1) and 150g of water into a reaction kettle, setting the stirring speed to be 350r/min, slowly heating to 30 ℃, and reacting for 5 hours.
(2) Alkylation reaction
Slowly heating to 90 ℃, starting to add 33.7g of chloroethane in 3 times (50% for the first time, 25% for every 30 minutes and the rest 25% for every 30 minutes), and keeping the temperature for reaction for 5 hours. Cooling and releasing pressure after the reaction is finished, and introducing the mixed materials in the reaction kettle into a separating funnel for standing and layering to obtain a semi-finished product.
(2) Post-treatment
Pouring the semi-finished product into a flask, adding 47g of 37 wt% hydrochloric acid solution, heating to 50 ℃ to remove BOC groups, introducing the generated gas into 10 wt% sodium hydroxide solution to remove CO2Collecting isobutene, collecting upper layer oily matter in a layered mode to obtain a finished product of N-ethylaniline, wherein the purity is 88%, and the purity of the N, N-diethylaniline is 9%, which shows that the reaction is incomplete due to too low reaction temperature in the amino protection process, so that the purity of the product is reduced.
Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the above description of the present invention, and equivalents also fall within the scope of the invention as defined by the appended claims.
Claims (8)
1. A preparation method of N-ethylaniline is characterized by comprising the following steps:
(1) adding an aniline aqueous solution into a reaction kettle, adding BOC acid anhydride serving as an amino protective agent, adding an acid binding agent, and reacting at 50-80 ℃ for amino protection, wherein the reaction formula is as follows:
(2) feeding chloroethane into the reaction kettle in batches for multiple times for alkylation reaction, heating to 80-100 ℃, and carrying out heat preservation reaction, wherein the reaction pressure is controlled to be 0.05-0.5 MPa, and the reaction formula is as follows:
(3) and (3) after the alkylation reaction is finished, discharging chloroethane gas in the reaction kettle, cooling and recovering the chloroethane gas for the step (2), standing and layering the obtained reaction liquid, using the lower-layer water phase as next batch of mother liquid water for reuse, adding hydrochloric acid into the upper-layer oil phase to remove BOC and collecting generated isobutene to obtain the product N-ethylaniline, wherein the reaction formula is as follows:
the feeding molar ratio of the aniline to the BOC anhydride to the chloroethane to the water to the acid-binding agent to the hydrochloric acid is 1: 0.5-0.6: 1-1.1: 15-20: 0.3-0.5: 1-1.1, wherein the feeding molar amount of the hydrochloric acid is calculated by HCl.
2. The production method according to claim 1, wherein in the step (1), the acid scavenger is fed simultaneously with the aqueous aniline solution at once or in a plurality of times in batches.
3. The preparation method according to claim 1, wherein in the step (1), the stirring speed in the reaction kettle is 350rpm, and the reaction time is 5 hours.
4. The method according to claim 1, wherein the ethyl chloride is fed in 3 batches, the time interval between each batch is 30min, and the addition amount of each batch is 50%, 25% and 25% of the total addition amount of the ethyl chloride in sequence.
5. The preparation method according to claim 1, wherein in the step (2), the temperature is raised to 90-100 ℃ for reaction under the condition of heat preservation for 5-7 hours.
6. The method according to claim 1, wherein in the step (3), the HCl mass concentration in the hydrochloric acid is 37-40%.
7. The process according to claim 1, wherein the reaction temperature for removing BOC in the step (3) is 50 ℃.
8. The process according to claim 1, 6 or 7, characterized in that the collection of the isobutene formed is in particular: introducing gas generated by adding hydrochloric acid into the upper oil phase to remove BOC into sodium hydroxide solution to remove CO2And collecting the isobutene.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145562A (en) * | 2013-03-18 | 2013-06-12 | 黄河三角洲京博化工研究院有限公司 | N-ethyl aniline preparation method |
| CN103193656A (en) * | 2013-04-08 | 2013-07-10 | 黄河三角洲京博化工研究院有限公司 | Synthesis method of N-ethylaniline |
| CN106008225A (en) * | 2016-06-12 | 2016-10-12 | 嘉兴富成化工科技有限公司 | Method for preparing high-production-efficiency zero-emission N-ethyl aniline |
| CN106083609A (en) * | 2016-06-27 | 2016-11-09 | 南通新邦化工科技有限公司 | Aniline syntehsizing diphenylamine reaction preparation MEA and cumidine |
| CN108285418A (en) * | 2018-02-13 | 2018-07-17 | 江苏优普生物化学科技股份有限公司 | 2- methyl -6- ethyl aniline synthetic methods |
-
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- 2020-10-15 CN CN202011103555.0A patent/CN112341341B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103145562A (en) * | 2013-03-18 | 2013-06-12 | 黄河三角洲京博化工研究院有限公司 | N-ethyl aniline preparation method |
| CN103193656A (en) * | 2013-04-08 | 2013-07-10 | 黄河三角洲京博化工研究院有限公司 | Synthesis method of N-ethylaniline |
| CN106008225A (en) * | 2016-06-12 | 2016-10-12 | 嘉兴富成化工科技有限公司 | Method for preparing high-production-efficiency zero-emission N-ethyl aniline |
| CN106083609A (en) * | 2016-06-27 | 2016-11-09 | 南通新邦化工科技有限公司 | Aniline syntehsizing diphenylamine reaction preparation MEA and cumidine |
| CN108285418A (en) * | 2018-02-13 | 2018-07-17 | 江苏优普生物化学科技股份有限公司 | 2- methyl -6- ethyl aniline synthetic methods |
Non-Patent Citations (2)
| Title |
|---|
| DALLA CROCE, PIERO ET AL.: "Selective monoalkylation of amines", 《JOURNAL OF CHEMICAL RESEARCH》 * |
| 高益令: "N-乙基邻甲苯胺的合成与应用", 《精细化工》 * |
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