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Novel synthesis method of alkoxymethylamine compound

A technology of alkoxymethylamines and compounds, which is applied in the field of preparation of alkoxymethylamines, can solve the problems of non-recyclable use, large discharge of three wastes, large amount of hydrochloric acid, etc., and achieve environmental protection and increase in reaction yield , the effect of high yield

Inactive Publication Date: 2019-08-30
SHANDONG BINNONG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The amount of hydrochloric acid is large and cannot be reused, which not only causes a waste of resources, but also needs to use a large amount of alkali to neutralize it in the subsequent steps of removal, resulting in a lot of waste water and salt in the production process, large discharge of three wastes, and heavy environmental pollution. It is a strong carcinogen chloromethyl alkyl ether that will be produced during the production process, which will have a greater impact on the safety of the product

Method used

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  • Novel synthesis method of alkoxymethylamine compound
  • Novel synthesis method of alkoxymethylamine compound
  • Novel synthesis method of alkoxymethylamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0039] Preparation of 2,6-diethyl-N-(methoxymethyl)aniline

[0040] According to the feed ratio in Table 1, add formaldehyde and methanol into a three-necked flask equipped with a condenser and a thermometer, add a catalyst, heat up to reflux, and separate the generated water during the reaction. After HPLC detected that the reaction was complete, dimethoxymethane intermediate was obtained by distillation under reduced pressure.

[0041] Feed ratio and reaction conditions of table 1 acetal reaction

[0042]

[0043] According to the proportioning and reaction conditions of Table 2, the dimethoxymethane intermediate (A), 2,6-diethylaniline (B) and solvent prepared in Example 1-5 were added to the reaction flask and kept warm Reaction, HPLC detection After the completion of the reaction, separate the generated methanol and solvent recovery, and distill to obtain 2,6-diethyl-N-(methoxymethyl)aniline.

[0044] Feed ratio and reaction conditions of table 2 alkylation reaction ...

Embodiment 6

[0047] Example 6 2,6-diethyl-N-(ethoxymethyl)benzene

[0048] Add 1 mol of formaldehyde and 2.05 mol of ethanol into a three-necked flask equipped with a thermometer, add 0.86 g of p-toluenesulfonic acid, heat up to reflux, and separate the generated water during the reaction. After completion of the reaction as detected by HPLC, diethoxymethane was obtained by vacuum distillation with a yield of 96% and a content of 98.8%.

[0049] Add 0.3mol of diethoxymethane, 0.5mol of 2,6-methylethylaniline and 100mL of benzene into the reaction flask, keep it warm at 75-80°C for 15 hours, and separate out the ethanol and benzene generated after the reaction is completed by HPLC. 2,6-diethyl-N-(ethoxymethyl)aniline was obtained with a yield of 96.2% and a content of 98.3%.

[0050] The total yield of the above two-step reaction is 92.35%.

Embodiment 7

[0051] Example 7 2,6-diethyl-N-(butoxymethyl)aniline

[0052]Add 1 mol of formaldehyde and 2.05 mol of butanol into a three-necked flask equipped with a thermometer, add 0.44 g of sulfamic acid, heat up to reflux, and separate the generated water during the reaction. After the reaction was complete as detected by HPLC, dibutoxymethane was obtained by distillation under reduced pressure, with a yield of 96.8% and a content of 98.5%.

[0053] Add 0.55 mol of dibutoxymethane, 0.5 mol of 2,6-diethylaniline and 100 mL of xylene into the reaction flask, keep warm at 135-140°C for 9 hours, and separate the produced butanol and xylene for recovery after HPLC detection. Apply mechanically, and distill to obtain 2,6-diethyl-N-(butoxymethyl)aniline with a yield of 96.2% and a content of 98.3%.

[0054] The total yield of the above two-step reaction is 93.12%.

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Abstract

The invention relates to a novel synthesis method of an alkoxymethylamine compound. The novel synthesis method comprises the steps: (1) dehydrating formaldehyde HCHO and alcohol R1OH by carrying out an aldolization under the action of an acid catalyst to obtain dialkoxymethane; and (2) carrying out a hydrocarbylation reaction on dialkoxymethane obtained in step (1) and substituted amine R2-NH2 toremove alcohol to obtain an alkoxymethyl substituent amine compound N-R1 oxymethyl-N-R2 amine. The synthesis method disclosed by the invention is simple in operation and high in yield reaching 92% orabove; and compared with the prior art, the novel synthesis method has the advantages that no acid wastewater, waste salts and chloromethyl alkyl ether serving as a cancerogen are greatly generated, the environment protection cost is favorably reduced, and the industrial prospect is higher.

Description

[0001] 【Technical field】 [0002] The invention relates to a new method for preparing alkoxymethylamine compounds. [0003] 【Background technique】 [0004] Alkoxymethylamine compounds are a class of important nitrogen-containing organic synthesis intermediates, which are widely used in the fields of pesticides, medicine, integrated circuits, etc. For removing photoresist and cleaning etc. [0005] Its structural general formula is: [0006] [0007] in: [0008] R 1 is alkyl, aryl, C1-C4 alkoxy, alkoxyalkyl; [0009] R 2 is unsubstituted or replaced by one or more halogen, C1-C4 alkyl, C1-C4 alkoxy, NO 2 Alkanes or aromatic hydrocarbons substituted with groups composed of CN and CN. [0010] At present, the preparation method of alkoxymethylamine compound mainly contains: [0011] (1) Methylene imine method: [0012] First in G.M.Robinson, R.Robinson, J.Chem.Soc., 123,523 (1923), it is reported that the dehydration reaction of amine compounds and formaldehyde genera...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C217/08C07C217/16C07C253/30C07C255/59
CPCC07C41/56C07C213/08C07C253/30C07C217/08C07C217/16C07C255/59C07C43/30
Inventor 徐家俊盛庆全张军
Owner SHANDONG BINNONG TECH
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