CN116262709A - Method for preparing amide by alcohol oxidation and cleavage - Google Patents
Method for preparing amide by alcohol oxidation and cleavage Download PDFInfo
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- CN116262709A CN116262709A CN202111535429.7A CN202111535429A CN116262709A CN 116262709 A CN116262709 A CN 116262709A CN 202111535429 A CN202111535429 A CN 202111535429A CN 116262709 A CN116262709 A CN 116262709A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
Abstract
The invention belongs to the technical field of chemistry and chemical engineering, and particularly relates to a method for continuously breaking alcohol into amide by using manganese oxide as a catalyst. Manganese oxide is used as a catalyst, molecular oxygen or air is used as an oxidant, and alcohol can be oxidized and broken into an amide compound after reacting for 12 hours at 130-150 ℃ in the presence or absence of a solvent. The catalyst of the invention can be recycled at least 9 times and still maintain good activity and selectivity. The catalyst of the method has the characteristics of simple preparation, low cost, high reaction selectivity, environmental friendliness and the like.
Description
Technical Field
The invention relates to the field of chemistry and chemical engineering, in particular to a method for generating amide by continuous oxidative cleavage of alcohol.
Technical Field
Amides and derivatives thereof are a class of compounds of great commercial value and have wide application as intermediates for biological products. In the course of the green and sustainable chemistry, there has been great interest in synthesizing amides from the ready-made oxidative cleavage of alcohols, and since Milstein et al reported the synthesis of secondary amides from primary alcohols and amine with PNN pliers-type Ru complexes, much effort has been directed toward this approach, most of which employ noble metals such as homogeneous Ru 13 And Rh 14 Complex and heterogeneous Ag/gamma-Al 2 O 3 . In addition, although heterogeneous Au-based catalysts have excellent catalytic performance for synthesizing amides from alcohols and amines under the condition of molecular oxygen in the presence of excessive amount of essential alkali additives, the heterogeneous Au-based catalysts are difficult to be applied on a large scale due to excessive cost. When reacting with inorganic ammonia, the applicability of the Au-based system is limited to benzamide, and the yield is low (50%). Despite the significant advances made by noble metal-based catalysts, non-noble metal catalyzed processes remain highly desirable from an economic and ecological standpoint, but are also very challenging.
Disclosure of Invention
The invention aims to provide a continuous cleavage amide path of an alcohol with mild reaction conditions, simple operation and high activity and selectivity.
The reaction according to the invention can be represented by the following general formula:
wherein R is a 2-, 3-or 4-substituted aromatic or heteroatomic aromatic hydrocarbon, and the substituent is selected from aryl, halogen, nitro, alkoxy, alkyl or hydrogen atoms.
In the present invention, the catalyst is MnO x The catalyst is prepared by adopting a grinding method familiar to researchers in the field, wherein a manganese precursor in the catalyst is one or two of manganese acetate, manganese chloride, manganese sulfate or manganese nitrate, and potassium permanganate is preferred to be potassium permanganate and manganese acetate. ReactionThe catalyst amount in the process is controlled to be 30 to 50mg, preferably 40mg.
The oxidant involved in the invention is molecular oxygen, including air or oxygen, and the pressure of pressurizing and oxygen supplying of the autoclave is 0.5Mpa in the reaction process.
The present invention preferably uses 1, 4-dioxane as a reaction solvent, and the conventional solvents such as t-butylbenzene, n-heptane, t-amyl alcohol and butyl acetate are used, and the results are not good. . The solvent is used in an amount of 1-3mL, preferably 2mL.
The temperature is preferably 130-150 ℃, and the catalyst can be used by filtration, washing and drying in the regeneration cycle.
The catalyst of the invention can be recycled at least 9 times and still maintain good activity and selectivity. The catalyst of the method has the characteristics of simple preparation, low cost, high reaction selectivity, environmental friendliness and the like.
Detailed Description
The following examples will aid in the understanding of the present invention, but the present invention is not limited thereto.
Example 1
40mg MnO 2 Adding the catalyst, 0.5mmoL phenethyl alcohol and 2mL 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa oxygen and 0.5MPa ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS with 100% conversion of phenethyl alcohol and 97% yield of benzamide product.
Comparative example 1
40mg MnO 2 Adding the catalyst, 0.5mmoL phenethyl alcohol and 0.5mL 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa oxygen and 0.5MPa ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS with 100% conversion of phenethyl alcohol and 28% yield of benzamide product.
TABLE 1 cleavage of phenethyl alcohol to amide
TABLE 2 comparison of cleavage of phenethyl alcohol to an amide-ammonium source
Example 11
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-methoxyphenylethanol and 3mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, placing into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-methoxybenzamide product was 88%.
Example 12
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-methylphenylethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-methylbenzamide product was 89%.
Example 13
40mg MnO 2 Adding the catalyst, 0.5mmol of 3-methyl phenethyl alcohol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 3-methylbenzamide product was 83%.
Example 14
40mg MnO x Adding the catalyst, 0.5mmol of 1-methyl phenethyl alcohol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. Reaction productAnalysis using GC-MS gave a yield of 70% 2-methylbenzamide product.
Example 15
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-nitroethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, placing into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-nitrobenzamide product was 95%.
Example 16
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-trifluoromethyl phenethyl alcohol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 130 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-trifluoromethyl benzamide product was 94%.
Example 17
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-chlorophenyl ethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-chlorobenzamide product was 95%.
Example 18
40mg MnO 2 Adding the catalyst, 0.5mmol of 3-chlorophenyl ethanol and 3mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, placing into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 3-chlorobenzamide product was 89%.
Example 19
40mg MnO 2 The catalyst, 0.5mmol of 2-chlorophenyl ethanol and 2mL of 1, 4-dioxane were added to a 10mL reaction flask, followed by transfer to a stainless steel autoclave,charging oxygen gas of 0.5MPa and ammonia gas of 0.5MPa, placing into an oil bath pot of 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 2-chlorobenzamide product was 87%.
Example 20
40mg MnO 2 Adding the catalyst, 0.5mmol of 3-chlorophenyl ethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 2-chlorobenzamide product was 85%.
Example 21
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-bromophenyl ethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 140 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-bromobenzamide product was 88%.
Example 22
40mg MnO 2 Adding the catalyst, 0.5mmol of 4-fluorophenylethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 4-fluorobenzamide product was 86%.
Example 23
40mg MnO 2 Adding the catalyst, 0.5mmol 2-pyridine ethanol and 2mL 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, charging 0.5MPa oxygen and 0.5MPa ammonia, placing into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 2-pyridinecarboxamide product was 92%.
Example 24
40mg MnO 2 Catalyst, 0.5mmol 3-pyridineEthanol and 2mL of 1.4-dioxane are added into a 10mL reaction bottle, then transferred into a stainless steel high-pressure reaction kettle, filled with 0.5MPa oxygen and 0.5MPa ammonia, placed into an oil bath kettle at 150 ℃ and stirred for reaction for 12h, and the pressure is kept unchanged in the reaction process. The reaction product was analyzed by GC-MS and the 3-pyridinecarboxamide product yield was 85%.
Example 25
40mg MnO 2 Adding the catalyst, 0.5mmol of 2-thiopheneethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of the 2-thiophenecarboxamide product was 90%.
Example 26
40mg MnO 2 Adding the catalyst, 0.5mmol of 3-thiopheneethanol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of the 3-thiophenecarboxamide product was 84%.
Example 27
40mg MnO 2 Adding the catalyst, 0.5mmol of 2-furol and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, putting into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the yield of 2-furoformamide product was 80%.
Example 28
40mg MnO 2 Adding the catalyst, 0.5mmol of 1-hydroxyindane and 2mL of 1.4-dioxane into a 10mL reaction bottle, transferring into a stainless steel high-pressure reaction kettle, filling 0.5MPa of oxygen and 0.5MPa of ammonia, placing into an oil bath kettle at 150 ℃, stirring and reacting for 12h, and keeping the pressure unchanged in the reaction process. The reaction product was analyzed by GC-MS and the phthalimide product yield was 81%.
Example 29
40mg MnO 2 The catalyst, 0.5mmol of 1,2,3, 4-tetrahydro-1-naphthol and 2mL of 1, 4-dioxane are added into a 10mL reaction bottle, then the reaction bottle is transferred into a stainless steel high-pressure reaction kettle, 0.5MPa of oxygen and 0.5MPa of ammonia gas are filled, the reaction kettle is placed into an oil bath pot at 150 ℃ for stirring reaction for 12 hours, and the pressure is kept unchanged in the reaction process. The reaction product was analyzed by GC-MS and the phthalimide product yield was 78%.
Claims (5)
1. A method for continuously breaking alcohol into amide by manganese oxide, which is characterized in that: at MnO 2 Under the action of a catalyst, in a 1, 4-dioxane solvent, molecular oxygen and/or air are used as oxygen sources, and the reaction is carried out at 130-150 ℃ in the presence of an ammonium source, so that alcohol is continuously broken to generate amide, wherein the reaction formula is as follows:
wherein R is 2-, 3-or 4-substituted aromatic or hetero-atom aromatic hydrocarbon, and the substituent is one or more than two of C6-C12 aryl, halogen, nitro, alkoxy, C1-C20 alkyl or hydrogen atoms.
2. The method for preparing amide by oxidative cleavage of alcohol according to claim 1, wherein: the ammonium source used in the reaction can be one or more than two of ammonia water, ammonium acetate, ammonium carbonate, ammonium bicarbonate and ammonia gas, preferably ammonia gas, and the pressure of the ammonia gas is 0.4Mpa-0.6Mpa, preferably 0.5Mpa.
3. The method for preparing amide by oxidative cleavage of alcohol according to claim 1, wherein: one or two of molecular oxygen and air are oxidants, and the pressurizing and oxygen supplying pressure of the autoclave is 0.4Mpa-0.6Mpa, preferably 0.5Mpa.
4. The method for preparing amide by oxidative cleavage of alcohol according to claim 1, wherein: the catalyst is used in an amount of 30-50mg, preferably 40mg, per 0.5mmol of substrate.
5. The method for preparing amide by oxidative cleavage of alcohol according to claim 1, wherein: the solvent is used in an amount of 1 to 3mL, preferably 2mL, per 0.5mmol of substrate.
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