CN114507145A - Synthesis method of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt - Google Patents

Synthesis method of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt Download PDF

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CN114507145A
CN114507145A CN202111675525.1A CN202111675525A CN114507145A CN 114507145 A CN114507145 A CN 114507145A CN 202111675525 A CN202111675525 A CN 202111675525A CN 114507145 A CN114507145 A CN 114507145A
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quaternary ammonium
ammonium salt
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张子印
刘彩霞
张岩
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Langfang Beechen Business Establishing Resin Material Co ltd
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    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/20—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of quaternary ammonium compounds
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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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    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
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Abstract

The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt, which comprises the steps of firstly preparing N-acetyl amantadine through Ritter reaction between adamantane and nitrile compounds, then hydrolyzing to generate 1-adamantadine, and then reacting the obtained 1-adamantadine with dimethyl carbonate under the catalysis of NaH in one step to generate the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt. The synthesis method can realize the synthesis of the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt by only three steps, effectively shortens the process route, does not introduce halogen ions in the synthesis process, can avoid the residues of the halogen ions in the product, can reduce the environmental pollution, and is more suitable for industrial production.

Description

Synthesis method of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt.
Background
Under the promotion of policies of developing new industry, removing capacity, saving energy, reducing emission and the like in China, the requirements of industries such as coal chemical industry, petroleum refining, metallurgy, environmental protection and the like on high-performance molecular sieve adsorbents and catalysts are remarkably increased. Currently, among a plurality of molecular sieves, CHA-type microporous molecular sieves are popular in research, and typical molecular sieves include SAPO-34 and SSZ-13 molecular sieves, wherein SSZ-13 molecular sieves are widely applied to a plurality of fields such as catalytic synthesis, environmental protection, new energy sources and the like in recent years due to an ordered pore structure, a large specific surface area, high catalytic activity, good hydrothermal stability and the like. The key raw material template agent for preparing molecular sieves such as SSZ-13 and the like is mostly N, N, N-trimethyl-1-adamantyl ammonium hydroxide, wherein N, N, N-trimethyl-1-adamantyl quaternary ammonium salt is an essential intermediate for synthesizing the N, N, N-trimethyl-1-adamantyl ammonium hydroxide.
In the existing synthesis process, the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt mainly takes adamantane as an initial raw material, 1-halogenated adamantane or 1-adamantanamine is synthesized, and then methylation reaction is carried out to generate the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt. The synthesis route needs to adopt halogen as a halogenating reagent, and the application of the halogenating reagent not only pollutes the environment, but also introduces impurity particles into the product to influence the purity of the product; and the existing synthesis process has long route, has strict requirements on reaction parameters, is difficult to control and is not suitable for industrial production.
Disclosure of Invention
Aiming at the technical problems of environmental pollution, long process route, difficult control of reaction process and unsuitability for industrial production in the synthesis process of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt in the prior art, the invention provides the synthesis method of the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt, the synthesis method greatly shortens the synthesis route, the used raw materials are green and environment-friendly, and the reaction process is easy to control.
In order to achieve the purpose of the invention, the embodiment of the invention adopts the following technical scheme:
the embodiment of the invention provides a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt, which comprises the following steps: the method specifically comprises the following steps:
s1: dissolving adamantane and nitrile compounds in concentrated sulfuric acid, adding a catalyst, uniformly stirring, heating to 40-80 ℃, reacting, adding ice water, stirring, extracting, washing and drying the obtained organic layer, and removing the solvent to obtain N-acetyl amantadine;
s2: dissolving the N-acetyl adamantane obtained in the step S1 and an inorganic base in a solvent, reacting at a high temperature of 100-160 ℃, adding ice water, extracting, washing and drying an obtained organic layer, and removing the solvent to obtain a 1-adamantanamine solid;
s3: mixing the obtained 1-amantadine with dimethyl carbonate and NaH catalyst, stirring for reaction at a high temperature of 100-160 ℃, washing with dimethyl carbonate, and carrying out solid-liquid separation and drying to obtain the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt.
Compared with the prior art, the synthesis method of the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt provided by the invention firstly prepares N-acetylamantadine in one step through the Ritter reaction between adamantane and nitrile compounds, then hydrolyzes to generate 1-adamantylamine, and then the obtained 1-adamantylamine reacts with dimethyl carbonate in one step under the catalysis of NaH to generate the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt, so that the process route is effectively shortened, and halogen ions are not introduced in the synthesis process, so that the halogen ions are prevented from being remained in the product, the environmental pollution is reduced, and the method is more suitable for industrial production. The prepared N, N, N-trimethyl-1-adamantyl quaternary ammonium salt can be used for generating high-purity N, N, N-trimethyl-1-adamantyl ammonium hydroxide through an electrolytic method and an electrodialysis method, and can be used as a template agent for synthesizing a molecular sieve.
Preferably, the molar ratio of the adamantane, the nitrile compound, the concentrated sulfuric acid and the catalyst in S1 is 1: 2-5: 10-20: 0.01 to 0.1, and more preferably in a molar ratio of 1: 3-4: 12-16: 0.04-0.06, and the more preferable molar ratio is 1: 4: 14: 0.04.
preferably, the catalyst is t-butanol, a Ni catalyst, HTMP, TEBAC, or p-toluenesulfonic acid, with a more preferred catalyst being a Ni catalyst.
The yield of the product is greatly influenced by the amount of the raw materials, and the yield of the N-acetyl adamantane can be ensured while the one-step preparation of the N-acetyl amantadine is realized at the preferable amount of the raw materials.
Preferably, the temperature in the reaction process in S1 is 40-70 ℃, and the reaction time is 1.5-3 h; the further preferable temperature is 60-70 ℃, and the reaction time is 2-2.5 h.
The reaction temperature can influence the stable state of the reaction system and the yield of the product, and the reaction is carried out at the optimal reaction temperature, so that the stability of the reaction system can be ensured, the reaction rate can be ensured to be improved, and the reaction time can be shortened.
Preferably, the nitrile compound is at least one of acetonitrile, propionitrile, and phenylacetonitrile.
Preferably, after the heating reaction in S1 is completed, ice water is added, and then the mixture is stirred for 0.8-1.2 hours at the temperature of 0-5 ℃.
Preferably, the extractant used in S1 is dichloromethane.
Preferably, the molar ratio of N-acetylamantadine, inorganic base and solvent in S2 is 1: 2-8: 5 to 10, and more preferably in a molar ratio of 1: 4-6: 6-8, and the more preferable molar ratio is 1: 5.5: 7.
the yield of the product is greatly influenced by the consumption of the raw materials, and under the optimal consumption of the raw materials, the yield of the product can be ensured, and excessive raw material loss can be avoided.
Preferably, the solvent may be selected from ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol or glycerol, with 1, 2-propylene glycol being a more preferred solvent.
Preferably, the temperature of the high-temperature reaction in S2 is 100-150 ℃, the reaction time is 5-15 h, further preferably 120-140 ℃, and the reaction time is 6-10 h.
Preferably, the molar ratio of 1-amantadine, dimethyl carbonate and NaH catalyst in S3 is 1: 5-15: 0.01 to 0.10, and more preferably in a molar ratio of 1: 6-8: 0.05-0.08, and the more preferable molar ratio is 1: 8: 0.06.
preferably, the high-temperature reaction temperature in S3 is 100-150 ℃, the reaction time is 3-10 h, further preferably 120-140 ℃, and the reaction time is 4-6 h.
Drawings
FIG. 1 is a synthetic route of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt provided by the examples of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The present invention will be further illustrated by the following examples, wherein the synthetic route of the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt provided by the present invention is shown in FIG. 1.
Example 1
The embodiment provides a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt, which specifically comprises the following steps:
s1: dissolving 10mmol of adamantane and 30mmol of benzyl cyanide in 100mmol of concentrated sulfuric acid, adding 0.3mmol of Ni catalyst, stirring at normal temperature for 0.5h, and reacting at 60 ℃ for 3 h; adding ice water to the reaction mixture and stirring at 0-5 ℃ for 1h, extracting with dichloromethane and washing the resulting organic layer with cold water, Na2SO4After drying and removal of the solvent under vacuum, a white solid of N-acetylamantadine was obtained, which was checked to have a yield of 77.5%.
S2: dissolving 10mmol of N-acetyl amantadine obtained from S1 and 40mmol of KOH in 60mmol of 1, 2-propylene glycol solvent, uniformly mixing, reacting at 140 ℃ for 10h, and then adding ice water. The reaction mixture was extracted with dichloromethane, the separated organic layer was washed with cold water and Na2SO4Drying and removing the solvent in vacuum to obtain solid 1-amantadine. The yield of 1-amantadine was found to be 71.3%.
S3: and (2) adding 10mmol of 1-amantadine prepared in S2, 90mmol of dimethyl carbonate and 0.4mmol of NaH into a pressure-resistant reaction kettle, stirring and reacting for 8h at 120 ℃, cooling, concentrating under reduced pressure, washing with dimethyl carbonate, filtering under reduced pressure, and drying a filter cake under reduced pressure to obtain the N, N, N-trimethyl-1-adamantyl carbonate. The yield of N, N, N-trimethyl-1-adamantyl carbonate was found to be 90.4%.
Examples 2 to 11
Examples 2 to 11 respectively provide a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt. The process steps compared to example 1, the process and steps were identical to example 1 except that the amounts of phenylacetonitrile and concentrated sulfuric acid used were changed in S1, and the ratio of the amounts of adamantane to phenylacetonitrile and adamantane to concentrated sulfuric acid in each example S1 and the product yields for the corresponding S1 steps are shown in Table 1:
TABLE 1
Figure BDA0003451844790000051
Examples 12 to 21
Examples 12 to 21 respectively provide a method for synthesizing an N, N-trimethyl-1-adamantyl quaternary ammonium salt.
The procedure of this method was compared with example 10, and the procedures and steps were identical with those of example 10 except that the kind and amount of the catalyst were adjusted in S1, and the kinds of the catalyst, the ratio of the amounts of the catalyst to the amount of adamantane and the product yield of the corresponding S1 step are shown in table 2:
TABLE 2
Figure BDA0003451844790000052
Figure BDA0003451844790000061
Examples 22 to 28
Examples 22 to 28 each provide a method for synthesizing an N, N-trimethyl-1-adamantyl quaternary ammonium salt.
The procedure was as in example 17 except that the reaction temperature and reaction time in S1 were adjusted in accordance with example 17, and the reaction temperature, reaction time and corresponding product yield of S1 in each example are shown in table 3:
TABLE 3
Figure BDA0003451844790000062
Examples 29 to 33
Examples 29 to 33 provide methods for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salts, respectively.
The process compared to example 28, except for the change in the amount of potassium hydroxide species in S2, the remaining process parameters and process steps were consistent with example 28. The ratio of the amounts of potassium hydroxide to the amount of N-acetylamantadine material in each example to the yield of the S2 step is shown in Table 4:
TABLE 4
Figure BDA0003451844790000071
Examples 34 to 41
Examples 34 to 41 respectively provide a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt.
The process was performed in accordance with example 33, except that the kind and amount of the solvent used in S2 were changed, and the process parameters and process steps were the same as those of example 33, and the kinds of the solvents, the ratio of the solvents to N-acetylamantadine and the yields of S2 in the respective examples are shown in Table 5:
TABLE 5
Figure BDA0003451844790000072
Examples 42 to 50
Examples 42 to 50 respectively provide a method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt.
The process compared to example 38: the process parameters and process steps were as in example 38 except that the reaction temperature and reaction time were varied in S2, and the reaction temperature, reaction time and yield of the corresponding S2 step in each example are shown in Table 6:
TABLE 6
Figure BDA0003451844790000081
Examples 51 to 55
Examples 51 to 55 provide methods for producing N, N, N-trimethyl-1-adamantyl quaternary ammonium salts, respectively.
The process compared to example 50, except that the amount of dimethyl carbonate used in S3 was changed, the process parameters and process steps were kept the same as in example 50, and the mass ratio of dimethyl carbonate to methylating agent in each example and the yield of the corresponding S3 step are shown in Table 7:
TABLE 7
Figure BDA0003451844790000082
Examples 56 to 60
Examples 56 to 60 provide methods for producing N, N, N-trimethyl-1-adamantyl quaternary ammonium salts, respectively.
The process compares to example 54: the process parameters and process steps were as in example 54 except that the amount of NaH catalyst used in S3 was varied, and the ratio of the amount of NaH catalyst to the amount of N-acetylamantadine material in each example to the product yield for the corresponding S3 step is shown in table 8:
TABLE 8
Figure BDA0003451844790000091
Examples 61 to 69
Examples 61 to 69 provide methods for producing N, N, N-trimethyl-1-adamantyl quaternary ammonium salts, respectively.
The process compares to example 57: the process parameters and process steps were as in example 57 except that the reaction time and reaction temperature were varied in S3, and the reaction time, reaction temperature and product yield for the corresponding S3 step in each example are shown in Table 9:
TABLE 9
Figure BDA0003451844790000092
Figure BDA0003451844790000101
Example 70
This example provides a method for preparing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt.
S1: dissolving 1mol of adamantane and 4mol of benzyl cyanide in 14mol of concentrated sulfuric acid, adding 40mmol of Ni catalyst, stirring at normal temperature for 0.5h, and reacting at 65 ℃ for 2.5 h; adding ice water to the reaction mixture and stirring at 0-5 ℃ for 1h, extracting with dichloromethane and washing the resulting organic layer with cold water, Na2SO4After drying and removal of the solvent under vacuum, a white solid of N-acetylamantadine was obtained, which was checked to have a yield of 86.5%.
S2: dissolving 1mol of N-acetyl amantadine obtained from S1 and 5.5mol of KOH in 7mol of 1, 2-propylene glycol solvent, uniformly mixing, reacting for 6 hours at 140 ℃, and then adding ice water. The reaction mixture was extracted with dichloromethane and the separated organic layer was washed with cold water and Na2SO4Drying and removing the solvent in vacuum to obtain solid 1-amantadine. The yield of 1-amantadine was found to be 76.6%.
S3: adding 1mol of 1-amantadine prepared in S2, 8mol of dimethyl carbonate and 60mmol of NaH into a pressure-resistant reaction kettle, stirring and reacting for 6h at 140 ℃, cooling, concentrating under reduced pressure, washing with dimethyl carbonate, filtering under reduced pressure, drying a filter cake under reduced pressure, and obtaining the N, N, N-trimethyl-1-adamantyl carbonate. The yield of N, N, N-trimethyl-1-adamantyl carbonate was found to be 94.3%.
Comparative example 1
Comparative example 1 provides a method of preparing N-acetyl amantadine. Compared with the preparation process of the example 1, the preparation process and the steps of the method are consistent with the example 1 except that the using amounts of the phenylacetonitrile and the concentrated sulfuric acid in the S1 are changed, and the product yield of the adamantane to the phenylacetonitrile, the adamantane to the concentrated sulfuric acid and the corresponding S1 step in each comparative ratio S1 are shown in the table 10:
watch 10
Figure BDA0003451844790000102
Comparative example 2
Comparative example 2 provides a method for preparing N-acetyl amantadine. Compared with the embodiment 10 in the preparation process: the procedure and steps were as in example 10 except that no catalyst was added to S1, and the product yields at the S1 step in comparative example 2 are shown in Table 11:
TABLE 11
Figure BDA0003451844790000111
Comparative examples 3 to 4
Comparative examples 3 to 4 respectively provide a method for preparing N-acetylamantadine. The procedure was carried out in a manner consistent with example 17, except that the starting materials for the preparation were kept in accordance with example 17, and the operating procedures and procedures were kept in accordance with example 17, except that the reaction temperature and reaction time in S1 were adjusted, wherein the reaction temperature, reaction time and corresponding product yield in each comparative example S1 are shown in Table 12:
TABLE 12
Figure BDA0003451844790000112
Comparative example 5
Comparative example 5 provides a method for preparing a N, N-trimethyl-1-adamantyl quaternary ammonium salt.
The process compares to example 54: the process parameters and process steps were as in example 54 except that the amount of NaH catalyst used in S3 was varied, and the ratio of the amounts of NaH catalyst to N-acetylamantadine species in each pair of ratios to the product yield for the corresponding S3 step is shown in table 13:
watch 13
Figure BDA0003451844790000113
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.

Claims (10)

1. A synthetic method of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt is characterized by comprising the following steps:
s1: dissolving adamantane and nitrile compounds in concentrated sulfuric acid, adding a catalyst, uniformly stirring, heating to 40-80 ℃, reacting, adding ice water, stirring, extracting, washing and drying the obtained organic layer, and removing the solvent to obtain N-acetyl amantadine;
s2: dissolving the N-acetyl adamantane and the inorganic base in a solvent, reacting at a high temperature of 100-160 ℃, adding ice water, extracting, washing and drying the obtained organic layer, and removing the solvent to obtain 1-amantadine solid;
s3: mixing the 1-amantadine with dimethyl carbonate and NaH catalyst, stirring at a high temperature of 100-160 ℃, reacting, washing with dimethyl carbonate, and carrying out solid-liquid separation and drying to obtain the N, N, N-trimethyl-1-adamantyl quaternary ammonium salt.
2. The method for synthesizing an N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the molar ratio of the adamantane, the nitrile compound, the concentrated sulfuric acid and the catalyst in S1 is 1: 2-5: 10-20: 0.01 to 0.1.
3. The method for synthesizing an N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1 wherein the catalyst in S1 is t-butanol, Ni catalyst, HTMP, TEBAC or p-toluenesulfonic acid.
4. The method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the temperature of the reaction process in S1 is 40-70 ℃, and the reaction time is 1.5-3 h.
5. The method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the heating reaction in S1 is completed, ice water is added, and then the mixture is stirred for 0.8-1.2 hours at 0-5 ℃.
6. The method for synthesizing an N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the molar ratio of the N-acetylamantadine, the inorganic base and the solvent in S2 is 1: 2-8: 5 to 10.
7. The method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the solvent in S2 is ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol or glycerol.
8. The method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the temperature of the high-temperature reaction in S2 is 100-150 ℃, and the reaction time is 5-15 h.
9. The method for synthesizing an N, N-trimethyl-1-adamantyl quaternary ammonium salt as claimed in claim 1, wherein the molar ratio of the 1-adamantylamine, dimethyl carbonate and NaH catalyst in S3 is 1: 5-15: 0.01 to 0.10.
10. The method for synthesizing N, N, N-trimethyl-1-adamantyl quaternary ammonium salt according to claim 1, wherein the high temperature reaction temperature in S3 is 100-150 ℃ and the reaction time is 5-15 h.
CN202111675525.1A 2021-12-31 2021-12-31 Synthesis method of N, N, N-trimethyl-1-adamantyl quaternary ammonium salt Pending CN114507145A (en)

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