- Facile synthesis and promising antibacterial properties of a new guaiacol-based polymer
-
A new acrylamide-type monomer (N-(4-hydroxy-3-methoxy-benzyl)-acrylamide) derived from guaiacol was successfully synthesized. Polymers containing guaiacol moiety were obtained via conventional radical polymerization of this monomer with AIBN as initiator. The influence of reaction time, initiator concentration and temperature on polymers characteristics was studied. Evaluation of the termination mode in free-radical polymerization was performed by MALDI-TOF mass spectrometry. Termination occurs mainly by disproportionation reaction. Additional peaks in the spectrum were attributed to side chain reactions implying phenoxy radicals. This new polymer exhibits a potential antibacterial activity against Bacillus subtilis by using anti-adhesion and anti-biofilm tests. After an adhesion time of 3 h, compared to a non-coated glass slide, there was a decrease of bacteria of 99% on the polymer coated glass slide. After three days of culture in a bacterial suspension, no biofilm was observed on the polymer coated surface.
- Liu, Hefang,Lepoittevin, Bénédicte,Roddier, Céline,Guerineau, Vincent,Bech, Lo?c,Herry, Jean-Marie,Bellon-Fontaine, Marie-Noelle,Roger, Philippe
-
-
Read Online
- Reductive amination of bio-based 2-hydroxytetrahydropyran to 5-Amino-1-pentanol over nano-Ni-Al2O3catalysts
-
The synthesis of useful amines from bio-based carbonyl compounds is highly desired owing to their mild reaction conditions and green sustainability. The reductive amination of bio-furfural-derived 2-hydroxytetrahydropyran (2-HTHP) to high-value-added 5-Amino-1-pentanol (5-AP) was carried out over efficient Ni-Al2O3catalysts prepared by a co-precipitation method. Among the Ni-Al2O3catalysts with different Ni loadings (0-100 wt%) tested, the 50Ni-Al2O3catalyst exhibited the highest5-APyield of 91.3% under mild conditions of 60 °C and 2 MPa H2. This catalyst also presented good stability during a 150 h time-on-stream without appreciable deactivation. Characterization results showed that the 50Ni-Al2O3catalyst exhibited small Ni0nanoparticles (5.5 nm), a high reduction degree (up to 95%), and a large amount of strong Lewis acid sites. The cooperative catalysis of the strong Lewis acid sites and highly dispersed metallic Ni sites is suggested to play an important role in achieving high efficiency in2-HTHPreductive amination.
- Zhang, Jia,Yang, Jian,Tian, Junying,Liu, Hailong,Li, Xuemei,Fang, Weiguo,Hu, Xun,Xia, Chungu,Chen, Jing,Huang, Zhiwei
-
supporting information
p. 4236 - 4245
(2021/03/15)
-
- Preparation method of capsaicine and capsaicine prepared by method
-
The invention provides a preparation method of capsaicine and capsaicine prepared by the method. The preparation method comprises the following steps: in the presence of an organic solvent and a catalyst, by taking vanillylamine carboxylate and carboxylic acid as reactants, carrying out amidation reaction to obtain a capsaicine reaction liquid. Compared with the prior art, the capsaicine preparation method provided by the invention at least has one of the following beneficial effects: 1) vanillylamine is converted into vanillylamine carboxylate, so that the problem of oxidative discoloration of vanillylamine is avoided, and the problems of purification, drying and storage of intermediate products are solved; 2) the vanillylamine carboxylate can be directly used for the next amidation reaction, other substances are not introduced, and the amidation reaction, operation and post-treatment are not influenced; and 3) after the vanillylamine solid is salified and dissolved, the thorough separation of the Raney Ni catalyst is facilitated, and the catalyst separated by the method can be continuously used after being treated.
- -
-
Paragraph 0115-0117
(2021/04/07)
-
- Preparation method of capsaicin and capsaicin prepared by using method
-
The invention relates to a capsaicin preparation method and capsaicin prepared by the method. The preparation method comprises the steps that: in the presence of an organic solvent and a catalyst, vanillylamine and carboxylic acid serve as reactants, after amidation reaction, capsaicin reaction liquid is obtained, and the catalyst comprises a boric acid ester compound. Compared with the prior art, the capsaicin preparation method provided by the invention has the following beneficial effects: 1) a large amount of water is not generated in the reaction process, violent reflux for water separation is not needed, the production cost is reduced, and the production safety is improved; 2) boric acid is replaced by the boric acid ester compound, so that the reaction time can be shortened, the reaction yield can be improved, and the product purity is very high; and 3) the boric acid ester compound can be recycled after proper treatment after the reaction, so that the production cost is saved, and green production is realized.
- -
-
Paragraph 0009
(2021/06/26)
-
- Method for preparing primary amine by catalyzing reductive amination of aldehyde ketone compounds
-
The invention discloses a method for preparing primary amine by catalyzing reductive amination of aldehyde ketone compounds. The method comprises the following steps: 1) mixing nickel nitrate hexahydrate, citric acid and an organic solvent, carrying out heating and stirring until a colloidal material is obtained, drying the colloidal material, roasting the colloidal material in a protective atmosphere, pickling, washing and drying a roasted product, and performing a partial oxidation reaction on a dried product in an oxygen-nitrogen mixed atmosphere to obtain a catalyst for a reductive amination reaction; and 2) mixing aldehyde or ketone compounds, a methanol solution of ammonia and the reductive amination reaction catalyst, introducing hydrogen, and carrying out a reductive amination reaction. The method has the advantages of high primary amine yield, high selectivity, wide aldehyde ketone substrate range, short reaction time, mild reaction conditions, low cost, greenness, economicalperformance and the like; the used reductive amination reaction catalyst can be recycled more than 10 times, and the catalytic activity of the catalyst is not obviously changed in gram-level reactions; and the method is suitable for large-scale application.
- -
-
Paragraph 0045-0048; 0060-0063
(2020/05/30)
-
- Facile synthesis of controllable graphene-co-shelled reusable Ni/NiO nanoparticles and their application in the synthesis of amines under mild conditions
-
The primary objective of many researchers in chemical synthesis is the development of recyclable and easily accessible catalysts. These catalysts should preferably be made from Earth-abundant metals and have the ability to be utilised in the synthesis of pharmaceutically important compounds. Amines are classified as privileged compounds, and are used extensively in the fine and bulk chemical industries, as well as in pharmaceutical and materials research. In many laboratories and in industry, transition metal catalysed reductive amination of carbonyl compounds is performed using predominantly ammonia and H2. However, these reactions usually require precious metal-based catalysts or RANEY nickel, and require harsh reaction conditions and yield low selectivity for the desired products. Herein, we describe a simple and environmentally friendly method for the preparation of thin graphene spheres that encapsulate uniform Ni/NiO nanoalloy catalysts (Ni/NiO?C) using nickel citrate as the precursor. The resulting catalysts are stable and reusable and were successfully used for the synthesis of primary, secondary, tertiary, and N-methylamines (more than 62 examples). The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, and H2 under very mild industrially viable and scalable conditions (80 °C and 1 MPa H2 pressure, 4 h), offering cost-effective access to numerous functionalized, structurally diverse linear and branched benzylic, heterocyclic, and aliphatic amines including drugs and steroid derivatives. We have also demonstrated the scale-up of the heterogeneous amination protocol to gram-scale synthesis. Furthermore, the catalyst can be immobilized on a magnetic stirring bar and be conveniently recycled up to five times without any significant loss of catalytic activity and selectivity for the product.
- Cui, Zhibing,Liu, Jianguo,Liu, Qiying,Ma, Longlong,Singh, Thishana,Wang, Chenguang,Wang, Nan,Zhu, Yuting
-
supporting information
p. 7387 - 7397
(2020/11/19)
-
- Capsaicin preparation method and the preparation method of the capsaicin (by machine translation)
-
The present invention provides a capsaicin preparation method and the preparation method of the capsaicin. The capsaicin preparation method comprises: to vanilla amine free base and carboxylic acid as raw materials, the use of SiO2 - H3 BO3 Catalyst, in the acylation reaction is carried out in a solvent, to obtain the capsaicin reaction solution. The present invention provides capsaicin preparation method, compared with the prior art, has the following advantages: 1) with carboxylic acid as the raw material, to avoid the preparation of the acyl chloride and a large number of strong corrosive organic waste liquid generation; 2) SiO for2 - H3 BO3 Catalyst instead of boric acid as catalyst, can realize the repeated use of the catalyst, and the cost is reduced, significantly reduces the production of waste water containing boron; 3) can effectively shorten the reaction time, reduce energy consumption. (by machine translation)
- -
-
Paragraph 0100-0124
(2019/10/17)
-
- PROCESS FOR PRODUCING AN AMINE IN A SOLVENT SYSTEM CONTAINING WATER
-
The present invention pertains to a process for producing an amine from an aldehyde or a precursor thereof, or a ketone in a solvent system containing water. The process is more environmentally friendly and permits to obtain an amine compound under mild reaction conditions.
- -
-
Page/Page column 17-18
(2019/10/04)
-
- Green and convenient protocols for the efficient reduction of nitriles and nitro compounds to corresponding amines with NaBH4 in water catalyzed by magnetically retrievable CuFe2O4 nanoparticles
-
Abstract: In this study, firstly, CuFe2O4 nanoparticles were prepared by a simple operation. The structure of the mentioned nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, vibrating sample magnetometer and also Brunauer–Emmett–Teller and Barrett–Joyner–Halenda analyses. The prepared magnetically copper ferrite nanocomposite was successfully applied as a simple, cost-effective, practicable, and recoverable catalyst on the green, highly efficient, fast, base-free, and ligand-free reduction of nitriles and also on the affordable and eco-friendly reduction of nitro compounds with the broad substrate scope to the corresponding amines with NaBH4 in water at reflux in high to excellent yields. Graphical abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
-
-
- A specific marker of the capsaicin fluorescent probe and its synthetic method and application
-
The invention relates to a specifically marked capsaicin fluorescent probe and a synthetic method and application thereof, which belong to the technical field of biology. Firstly, the invention discloses the specifically marked capsaicin fluorescent probe
- -
-
Paragraph 0051; 0052
(2018/01/11)
-
- MANUFACTURING METHOD OF AROMATIC COMPOUND AND FURAN DERIVATIVE HAVING METHYLAMINO GROUP
-
PROBLEM TO BE SOLVED: To provide a method for manufacturing an aromatic compound or a furan derivative where only aldehyde group is converted to an aminomethyl group while maintaining a structure of aromatic or furan ring from an aromatic compound or a furan derivative having an aldehyde group, capable of being conducted in a water solvent containing no organic solvent and relatively low in by-product. SOLUTION: Amine or ammonia is added in water at first to convert to imine, then a reaction is conducted by using compressive hydrogen with a pressure of 0.1 MPa to 4 MPa in the presence of a metal carried solid catalyst carrying one or more kind of metal selected from rhodium, palladium and platinum or an alloy containing these metal elements. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2017,JPOandINPIT
- -
-
Paragraph 0034; 0035
(2017/10/26)
-
- SYNTHESIS OF AMIDES AND AMINES FROM ALDEHYDES OR KETONES BY HETEROGENEOUS METAL CATALYSIS
-
This invention concerns the first mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalystand amine donor. The initial heterogeneous metal- catalyzed reaction between the carbonyl and the amine donor components is followed up with the addition of a suitable acylating agent component in one-pot. Hence, the present invention provides a novel catalytic one-pot three-component synthesis of amides. Moreover, the integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis ofamides from aldehyde and ketone substrates, respectively. The process can be applied to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. It can also be applied for asymmetric synthesis. In the present invention, a novel co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Moreover, implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.
- -
-
Page/Page column 17
(2016/07/05)
-
- Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis
-
Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced throughout the one-pot procedure involving multistep catalytic tandem operations. Several novel cocatalytic relay sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.
- Palo-Nieto, Carlos,Afewerki, Samson,Anderson, Mattias,Tai, Cheuk-Wai,Berglund, Per,Córdova, Armando
-
p. 3932 - 3940
(2016/07/06)
-
- Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: An environmentally friendly approach
-
A simple and highly efficient method was developed for the transformation of furfural (a biomass derived aldehyde) to furfurylamine by reductive amination using an aqueous solution of ammonia and molecular hydrogen as an amine source and a reducing agent, respectively. By choosing a suitable catalyst, such as Rh/Al2O3, and reaction conditions, a very high selectivity of furfurylamine (~92%) can be achieved within the reaction time of 2 h at 80 °C. A detailed analysis of the reaction system sheds some light on the reaction pathway and provides an understanding about each elementary step. The reaction was believed to proceed via an imine pathway although no such intermediate was detected because of the highly reactive nature. Optimization of different reaction parameters such as hydrogen pressure, temperature and substrate/ammonia mole ratio is shown to be critical to achieve high selectivity of furfurylamine. Time-dependent reaction profiles suggested that a Schiff base type intermediate was in the detectable range, which offers indirect evidence of the formation of imine. Competitive hydrogenation and amination of an aldehyde group were strongly dictated by the nature of the metal used. The studied protocol represents an environmentally benign process for amine synthesis, which can be effectively extended to the other aldehydes also. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.
- Chatterjee, Maya,Ishizaka, Takayuki,Kawanami, Hajime
-
supporting information
p. 487 - 496
(2016/01/30)
-
- Vanillylamine type new compound as well as preparation method and medical appliance thereof
-
The invention provides a novel compound of a treatment medicine or preventive medicine serving as an analgesic drug, and a medicinal composition containing the same. The invention relates to a vanillylamine type new compound or a pharmaceutically acceptab
- -
-
Paragraph 0033
(2016/10/31)
-
- Characterization of a novel amine transaminase from Halomonas elongata
-
Chiral amines are indispensable building blocks in the production of biologically active compounds. They are fundamental for the pharmaceutical industry, both as active molecules themselves and as chiral auxiliaries in asymmetric synthesis; however, the available synthetic strategies often present disadvantages. ω-Transaminases (ω-TAs) appear as an attractive alternative by driving the stereoselective amination of prochiral ketones. HEWT is a novel amine transaminase from the moderate halophilic bacterium, Halomonas elongata DSM 2581, which is highly (S)-selective, being able to fully convert (S)-1-phenylethylamine to acetophenone and showing no activity with the corresponding (R)-1-phenylethylamine. HEWT has a broad substrate scope, active with a range of amino donors and acceptors, and naturally accepts isopropylamine (IPA) as amino donor in asymmetric synthesis providing a 41% conversion of pyruvate in 24 h at 37°C starting with 1:1 molar ratio between the reagents. HEWT also accepts ortho-xylylenediamine as amino donor in for amine synthesis, in particular, with benzaldehyde yielding high conversions between 90 and 95%. The enzyme is also tolerant to the presence of cosolvents up to 20% making it a promising candidate for industrial applications.
- Cerioli, Lorenzo,Planchestainer, Matteo,Cassidy, Jennifer,Tessaro, Davide,Paradisi, Francesca
-
p. 141 - 150
(2015/09/01)
-
- EFFICIENT SYNTHESIS OF AMINES AND AMIDES FROM ALCOHOLS AND ALDEHYDES BY USING CASCADE CATALYSIS
-
The present invention relates generally to an eco-friendly methodology for the conversion of alcohols and aldehydes to amines and amides using an integrated enzyme cascade system with metal-and organocatalysis. More specifically, the present invention relates to synthesis of capsaicinoids starting from vanillin alcohol and using a combination of an enzyme cascade system and catalysts. Furthermore, the method also relates to synthesis of capsaicinoids derivatives starting from vanillin alcohol derivatives and using a combination of an enzyme cascade system and catalysts.
- -
-
Page/Page column 9
(2015/11/24)
-
- Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot
-
The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.
- Anderson, Mattias,Afewerki, Samson,Berglund, Per,Cordova, Armando
-
supporting information
p. 2113 - 2118
(2014/07/07)
-
- A new and convenient method for reduction of oximes to amines with NaBH3CN in the presence of MoCl5/NaHSO4? H2O system
-
Various aldoximes and ketoximes were efficiently reduced to their corresponding amines with NaBH3CN in the presence of MoCl 5/NaHSO4?H2O system. Reduction reactions were carried out in refluxing EtOH or DMF within 0.3-3.8 h to afford the amines in high to excellent yields.
- Kouhkan, Mehri,Zeynizadeh, Behzad
-
experimental part
p. 3323 - 3326
(2012/02/04)
-
- A rapid and practical protocol for solvent-free reduction of oximes to amines with NaBH4/ZrCl4/Al2O3 system
-
Solvent-free reduction of various aldoximes and ketoximes to the corresponding amines was performed easily and efficiently with NaBH4 in the presence of ZrCl4 supported on Al2O3. The reactions were carried out rapidly (within 2 min) at room temperature to afford the amines in high to excellent yields.
- Zeynizadeh, Behzad,Kouhkan, Mehri
-
experimental part
p. 3448 - 3452
(2012/02/01)
-
- Efficient chemoenzymatic synthesis of phenylacetylrinvanil: An ultrapotent capsaicinoid
-
The straightforward synthesis of phenylacetylrinvanyl (PhAR), an ultrapotent capsaicinoid is described. The process starts with the quantitative synthesis of methyl ricinoleate (MeRic) by castor oil methanolysis. Afterwards, two alternative routes are pos
- Castillo, Edmundo,Regla, Ignacio,Demare, Patricia,Luviano-Jardón, Axel,López-Munguía, Agustín
-
experimental part
p. 2869 - 2873
(2009/05/07)
-
- CAPSAICIN DERIVATES AND THE PRODUCTION AND USE THEREOF
-
The invention relates to new compounds, namely capsaicin derivates, a new method for their production, and their use as micro-organism-repellent agents in paints and coatings, in particular for marine installations and ships, but also for land-based struc
- -
-
Page/Page column 17; 21
(2010/02/11)
-
- Anti-tumor pharmaceutical composition comprising N-vanillyl fatty acid amide
-
The present invention provides an anti-tumor pharmaceutical composition having a high anti-tumor effect with low side-effects. The anti-tumor pharmaceutical composition comprises a N-vanillyl fatty acid amide of formula (1): wherein —CO—R group represents
- -
-
Page/Page column 4
(2008/06/13)
-
- Kinetics and mechanism of solvolysis of capsaicin analogues. The thermal decomposition reaction of pelargonic acid vanillylamide (N-[(4-hydroxy-3-methoxyphenyl)-methyl]nonenamide) in methanol solution
-
The thermal decomposition reactions of pelargonic acid vanillylamide, an analog of natural capsaicin (N-[(4-hydroxy-3-methoxyphenyl)-methyl]-8-methyl-(E)-6-nonenamide, were examined in methanol and in an alkaline aqueous methanolic solution, in the 53.6°-130.0°C temperature range. The analyses of the main reaction products were accomplished by an appropriate GC-MS procedure. The thermolysis of synthetic capsaicin follows pseudo first-order kinetic laws and the observed rate constant values depend both on the temperature and the pH of the solutions. In the above conditions the corresponding Arrhenius equations describe the temperature effect on the rates of solvolyses of that compound and allow to evaluate quantitatively its stability in solution. Furthermore, a reaction mechanism for the solvolyses with the participation of labile intermediates species can be postulated.
- Sein,Mandrile,Cafferata
-
p. 237 - 243
(2007/10/03)
-