2210-25-5Relevant articles and documents
A ritter-type reaction over H-ZSM-5: Synthesis of N-isopropylacrylamide from acrylonitrile and isopropyl alcohol
Chen, Xin,Okuhara, Toshio
, p. 194 - 201 (2002)
Catalytic synthesis of N-isopropylacrylamide from acrylonitrile and isopropyl alcohol has been studied using a variety of solid acids in a solid-liquid reaction system at 423 K. Among typical solid and liquid acids, H-ZSM-5 exhibited an exceptionally high catalytic activity. The activity (per gram) of H-ZSM-5 increased as the Al-content (100Al/(Si + Al)%) increased and then decreased through a maximum at an Al content of 2.63%. The specific activity per one acid site, which was estimated from the initial rate and the acid amount, increased greatly as the Al content decreased, which resembles those of the hydrophobicity and the acid strength. The superiority of H-ZSM-5 activity over other strong and hydrophobic solid acids suggests the importance of the unique pore structure. While H-ZSM-5 deactivated severely during the reaction, the catalytic activities were mostly recovered by calcination at 773 K in air. IR spectroscopy and adsorption measurements revealed that the deactivation of H-ZSM-5 was mainly caused by the formation of a polymer of acrylonitrile on the catalyst surface blocking the micropores, but not limiting desorption of the product from the micropores.
Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
, p. 319 - 330 (2021/10/29)
The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives
Sun, Xin,Bai, Xiao-Yan,Li, An-Zhen,Li, Bi-Jie
supporting information, p. 2182 - 2187 (2021/03/01)
Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.
Method for synthesizing acrylamide derivative
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Paragraph 0029; 0052; 0056, (2019/10/01)
The invention relates to a method for synthesizing an acrylamide derivative from alkyl primary amine and acrylamide as raw materials and belongs to the field of chemical product synthesis methods. Themethod for synthesizing the acrylamide derivative comprises the following steps: 1) under conditions of 150-160 DEG C and 0.6-1MPa, conducting a Diels-Alder reaction on acrylamide and anthracene so as to obtain an acrylamide addition intermediate of 1:1; 2) conducting backflowing on the addition intermediate, alkyl primary amine and a catalyst for 6-20 hours at 50-180 DEG C, and conducting an amino exchange reaction so as to obtain an acrylamide derivative addition intermediate; and 3) carrying out thermal cracking on the acrylamide derivative addition intermediate at 150-180 DEG C and 1-3kPa, conducting rectification so as to obtain an acrylamide derivative, conducting sublimation recycling on anthracene, and repeating the process. The method for synthesizing the acrylamide derivative, which is provided by the invention, is free of liquid solvent, is capable of effectively reducing the content of VOCs (volatile organic compounds) in the generation process, and is simple in reaction process, easy in product and recycling raw material separation, easy in reaction condition control, high in security, high in reaction yield, small in byproduct amount, simple in aftertreatment, high in product purity and easy in industrial production.
Synthesis process of N-isopropylacrylamide
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Paragraph 0023, (2018/04/01)
The invention relates to a synthesis process of N-isopropylacrylamide, and belongs to the technical field of new materials. According to the process, acrylonitrile and isopropanol have an alkylation reaction under the catalyzing of tetra-n-butylammonium chloride and sulphuric acid to prepare the N-isopropylacrylamide, an organic layer is separated after the N-isopropylacrylamide is neutralized through ammonium hydroxide, then the N-isopropylacrylamide is extracted through water, an extraction liquid is directly cooled and crystalized after being concentrated to obtain an N-isopropylacrylamide crystal, and the N-isopropylacrylamide crystal is dried in vacuum to obtain a product. The used raw materials are cheap and easy to get, the cost is low, the product purity is high, the yield is high, and the process flow is short. The synthesis process has a broad application prospect in the large-scale production of the N-isopropylacrylamide in a workshop.
MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE
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Paragraph 0055; 0057; 0060, (2018/07/03)
PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
(Meth) acrylamide N-substituted (by machine translation)
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Paragraph 0054; 0055; 0056; 0057, (2018/12/12)
PROBLEM TO BE SOLVED: a (meth) acrylic acid and a starting material, high yield, high-purity (meth) and N-substituted carboxylic acid amide derivative norbonene alkylacrylamide industrial production method. SOLUTION: and (meth) acrylic acid aminopentadienoic cyclometallized Diels-Alder reaction product of, norbonene carboxylic acid derivative, and silica as a main catalyst in the presence of an inorganic material, and amide-amine compound, norbonene carboxylic acid amide derivative. Furthermore, the vapor phase of the norbonene vinylcarboxamide deriv. aminopentadienoic cyclometallized by thermal decomposition reaction by desorbing, (meth) acrylamide purpose compd. N-substituted. Selected drawing: no (by machine translation)
METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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Paragraph 0057; 0060, (2017/01/05)
PROBLEM TO BE SOLVED: To provide an industrial method for producing a high-purity alkoxy propionic acid amide derivative and N-substituted (meth)acrylamide in a high yield, which uses a (meth)acrylic acid as a starting material. SOLUTION: There is provided a method for producing an objective compound, N-substituted (meth)acrylamide by the step of: amidating an alkoxy propionic acid derivative, which is synthesized from a (meth)acrylic acid and alcohol and represented by the formula [1], with an amine compound; R3-NH-R4(R3 and R4 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms or may form a saturated 5- to 7-membered ring with a nitrogen atom supporting them) in the presence of an inorganic material composed mainly of silica as a catalyst to obtain an alkoxy propionic acid amide derivative; and eliminating alcohol by the liquid phase thermal decomposition reaction of the alkoxy propionic acid amide derivative. (R1 represents H or a methyl group; and R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms or an alkenyl group.) COPYRIGHT: (C)2015,JPOandINPIT
METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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Paragraph 0053; 0056; 0057, (2018/11/22)
PROBLEM TO BE SOLVED: To provide an industrial method for efficiently producing a high-purity N-substituted (meth)acrylamide in a short time even under mild reaction conditions, which uses (meth)acrylic acid as a starting material and generates only water as a byproduct. SOLUTION: There is provided a method for producing an N-substituted (meth)acrylamide to obtain an objective compound, N-substituted (meth)acrylamide by the step of: reacting a (meth)acrylic and an amine compound to synthesize an aminopropionic acid derivative; then adding an inorganic material composed mainly of silica as a catalyst and performing amidation with the same amine compound to obtain an aminopropionic acid derivative; and subsequently eliminating an amine by the thermal decomposition reaction. COPYRIGHT: (C)2015,JPOandINPIT
METHOD OF PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE
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Paragraph 0053; 0057; 0058, (2018/12/12)
PROBLEM TO BE SOLVED: To provide a method of producing N-substituted (meth)acrylamide of high purity under mild conditions. SOLUTION: This invention relates to a method of obtaining N-substituted (meth)acrylamide [3] by the detachment of an amine compound through the liquid-phase thermal decomposition of an aminopropionic acid amide derivative [1] in the presence of a catalyst mainly composed of silica, wherein R1-R5 are represented by H, a C1-32 alkyl group, and a hydroxyalkyl group. COPYRIGHT: (C)2016,JPOandINPIT
