- Synthesis method of 2-aminopropanol
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The invention discloses a synthesis method of 2-aminopropanol. According to the method, epoxypropane and liquid ammonia are taken as raw materials, epoxypropane and liquid ammonia are introduced intoa fixed bed reactor, the molar ratio of epoxypropane to liquid ammonia is 1: (5-20), and under the action of a rare earth modified catalyst, reaction is carried out for 10-60s at the temperature of 100-200 DEG C, so that 2-aminopropanol is obtained. The method is reasonable in process, simple and convenient to operate, high in atom economy and low in emission of three wastes, and meets the requirements of industrial production.
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Paragraph 0033-0035; 0061-0070
(2020/04/29)
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- Selective amination of 1,2-propanediol over Co/La3O4 catalyst prepared by liquid-phase reduction
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The catalytic coupling of alcohol and ammonia is an environmentally friendly process. Cobalt-based catalysts, modified by supports (including CeO2, Fe3O4, Nb2O5, La3O4 and Al2O3), and prepared by the liquid-phase reduction, were used for the amination of 1,2-propanediol. The screened nano-Co/La3O4 catalyst exhibited an excellent catalytic performance of 68% conversion and 89% selectivity toward 2-amino-1-propanol under optimal conditions. The characterizations of the catalyst was performed by XRD, XPS, BET, TEM, TG, and CO2-TPD, revealing a relatively large specific surface area, strongly alkaline sites and a Co-La-O transition phase, which were responsible for the selective catalysis of 1,2-propanediol. The efficient construction of cobalt-based catalysts on the basis of the active species is key to improving the efficiency of the reaction process.
- Yue, Chuan-Jun,Di, Kai,Gu, Li-Ping,Zhang, Zhen-Wei,Ding, Lin-Lin
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- Method for preparing 2-amino propanol
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The invention discloses a method for preparing 2-amino propanol. The method comprises the following steps: (1) paraformaldehyde is dissolved in an alcohol amine aqueous solution to form a paraformaldehyde dissolving solution, then the paraformaldehyde dissolving solution is added dropwise into nitroethane to react, settling and separatinglayering are conducted after reaction is ended, unreacted nitroethane is separated through distillation, a product generated after the unreacted nitroethane is separated forms an intermediate product, and the intermediate product contains nitropropanol; (2) ametal catalyst is added in the intermediate product, H is introduced for reaction, and a reaction mixture is obtained after the reaction is completed; and (3) the reaction mixture obtained in the step (2) is filtered, a filtrate is decompressed and rectifiedsubjected to pressure-reduced rectification to obtain the 2-amino propanol. The method for preparing the 2-amino propanol has the advantagescharacteristics that the reaction efficiency is high, the product purity is high, three wastes are less, and the economical efficiency is good, thereby reducing the pollution to the environment.
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Paragraph 0021-0037
(2019/03/08)
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- Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay
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The design of a radical relay chaperone to promote selective C-H functionalizations is described. A saccharin-based imine was found to be uniquely suited to effect C-H amination of alcohols via an in situ generated hemiaminal. This radical chaperone facilitates the mild generation of an N-centered radical while also directing its regioselective H atom transfer (HAT) to the β carbon of an alcohol. Upon β C-H halogenation, aminocyclization, and reductive cleavage, an NH2 is formally added vicinal to an alcohol. The development, synthetic utility, and chemo-, regio-, and stereoselectivity of this imine chaperone-mediated C-H amination is presented herein.
- Nakafuku, Kohki M.,Twumasi, Raymond K.,Vanitcha, Avassaya,Wappes, Ethan A.,Namitharan, Kayambu,Bekkaye, Mathieu,Nagib, David A.
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p. 13065 - 13072
(2019/10/08)
-
- Rapid and Quantitative Profiling of Substrate Specificity of ω-Transaminases for Ketones
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ω-Transaminases (ω-TAs) have gained growing attention owing to their capability for asymmetric synthesis of chiral amines from ketones. Reliable high-throughput activity assay of ω-TAs is essential in carrying out extensive substrate profiling and establishing a robust screening platform. Here we report spectrophotometric and colorimetric methods enabling rapid quantitation of ω-TA activities toward ketones in a 96-well microplate format. The assay methods employ benzylamine, a reactive amino donor for ω-TAs, as a cosubstrate and exploit aldehyde dehydrogenase (ALDH) as a reporter enzyme, leading to formation of benzaldehyde detectable by ALDH owing to concomitant NADH generation. Spectrophotometric substrate profiling of two wild-type ω-TAs of opposite stereoselectivity was carried out at 340 nm with 22 ketones, revealing subtle differences in substrate specificities that were consistent with docking simulation results obtained with cognate amines. Colorimetric readout for naked eye detection of the ω-TA activity was also demonstrated by supplementing the assay mixture with color-developing reagents whose color reaction could be quantified at 580 nm. The colorimetric assay was applied to substrate profiling of an engineered ω-TA for 24 ketones, leading to rapid identification of reactive ketones. The ALDH-based assay is expected to be promising for high-throughput screening of enzyme collections and mutant libraries to fish out the best ω-TA candidate as well as to tailor enzyme properties for efficient amination of a target ketone.
- Han, Sang-Woo,Shin, Jong-Shik
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p. 3287 - 3295
(2019/06/21)
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- The invention relates to a propylene glycol and liquid ammonia as raw materials for preparing propylene diamine method and apparatus thereof
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The invention relates to a method for preparing propane diamine by taking propylene glycol and liquid ammonia as raw materials. Propylene glycol and liquid ammonia are mixed in a certain ratio and are pumped into a reactor by virtue of a pump, and reaction is carried out in presence of a catalyst and hydrogen. The method for preparing the propane diamine by taking the propylene glycol and liquid ammonia as the raw materials has the advantages that a novel catalyst is adopted, catalytic performance is excellent, and long-time operation can be easily carried out; propylene glycol is subjected to hydroamination for producing a propane diamine product at lower reaction pressure, and reaction conditions are adjusted and changed, so that composition of the product can be flexibly adjusted and changed, selectivity of a target product is improved, a reaction process is simple, one-time investment of a production unit and production cost are reduced, a reaction product and a catalyst can be simply separated, and large-scale continuous industrial production can be easily realized.
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Paragraph 0052-0053; 0089
(2017/08/31)
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- Production of Primary Amines by Reductive Amination of Biomass-Derived Aldehydes/Ketones
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Transformation of biomass into valuable nitrogen-containing compounds is highly desired, yet limited success has been achieved. Here we report an efficient catalyst system, partially reduced Ru/ZrO2, which could catalyze the reductive amination of a variety of biomass-derived aldehydes/ketones in aqueous ammonia. With this approach, a spectrum of renewable primary amines was produced in good to excellent yields. Moreover, we have demonstrated a two-step approach for production of ethanolamine, a large-market nitrogen-containing chemical, from lignocellulose in an overall yield of 10 %. Extensive characterizations showed that Ru/ZrO2-containing multivalence Ru association species worked as a bifunctional catalyst, with RuO2 as acidic promoter to facilitate the activation of carbonyl groups and Ru as active sites for the subsequent imine hydrogenation.
- Liang, Guanfeng,Wang, Aiqin,Li, Lin,Xu, Gang,Yan, Ning,Zhang, Tao
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supporting information
p. 3050 - 3054
(2017/03/14)
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- A metagenomics approach for new biocatalyst discovery: Application to transaminases and the synthesis of allylic amines
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Transaminase enzymes have significant potential for the sustainable synthesis of amines using mild aqueous reaction conditions. Here a metagenomics mining strategy has been used for new transaminase enzyme discovery. Starting from oral cavity microbiome samples, DNA sequencing and bioinformatics analyses were performed. Subsequent in silico mining of a library of contiguous reads built from the sequencing data identified 11 putative Class III transaminases which were cloned and overexpressed. Several screening protocols were used and three enzymes selected of interest due to activities towards substrates covering a wide structural diversity. Transamination of functionalized cinnamaldehydes was then investigated for the production of valuable amine building blocks.
- Baud, Damien,Jeffries, Jack W. E.,Moody, Thomas S.,Ward, John M.,Hailes, Helen C.
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p. 1134 - 1143
(2017/08/14)
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- Method of preparing new propanolamine
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The invention provides a method for preparing MNPA, DNPA and TNPA. The method comprises the following steps: taking PO and ammonium chloride as raw materials for reacting; adding water, ammonium chloride and the PO into a reaction kettle; gradually injecting partial PO while stirring; reacting and synthesizing MNPA.HCL and partial DNPA.HCL under the conditions of temperature at 60-80 DEG C and pressure control lower than or equal to 0.3MPa; separating the MNPA.HCL by utilizing the difference of physical property; injecting the remained PO into filtrate; reacting at 70-100 DEG C; cooling, filtering and drying, thereby obtaining TNPA.HCL; merging the cleaning solution with the filtrate, and then dehydrating, thereby obtaining the DNPA.HCL; and respectively reacting the three hydrochlorides with equivalent methanol alkali, thereby obtaining MNPA, DNPA and TNPA. The method has unique advantages; the relative temperature and pressure are lower during the preparation process; the equipment is simple and is low in investment; the main products are easily separated; the raw material PO is prevented from being subjected to side reactions, such as hydrolyzing into propylene glycol, and the like, under an alkali condition; the energy-saving, emission-reducing, low-carbon and environment-friendly effects are achieved; and the only byproduct sodium chloride is used as a self-use raw material for producing the ammonium chloride and sodium bicarbonate with relative high additional value is obtained.
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Paragraph 0008; 0033; 0034; 0047; 0049; 0051
(2016/10/07)
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- HIV INTEGRASE INHIBITORS
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The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
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- Metal-Free Reduction of Aromatic and Aliphatic Nitro Compounds to Amines: A HSiCl3-Mediated Reaction of Wide General Applicability
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A new, mild, metal-free, HSiCl3-mediated reduction of both aromatic and aliphatic nitro groups to amines that is of wide general applicability, tolerant of many functional groups, and respectful of the stereochemical integrity of stereocenters is reported.
- Orlandi,Tosi,Bonsignore,Benaglia
-
supporting information
p. 3941 - 3943
(2015/09/01)
-
- Structure of catalytically active Rh-In bimetallic phase for amination of alcohols
-
The structure of Rh-In bimetallic catalysts supported on carbon for amination of alcohols was determined by XRD, TEM-EDX, XPS, CO adsorption and EXAFS. At low In/Rh ratio (In/Rh ≤ 0.2), Rh metal particles with sizes of a tetragonal RhIn alloy with a particle size of ～20 nm was formed. This tetragonal alloy has a structure with a = 0.315 nm and c = 0.328 nm where metal atoms are located at (0, 0, 0) and (0.5, 0.5, 0.5). The catalytic activity of the tetragonal RhIn alloy is much higher than that of Rh metal particles with or without indium oxide species. With an excess amount of In (In/Rh > 1) on the high Rh loading (20 wt%) catalyst, the cubic RhIn phase with a CsCl structure was observed instead of the tetragonal RhIn phase, and the catalytic activity was much decreased.
- Takanashi, Tsukasa,Tamura, Masazumi,Nakagawa, Yoshinao,Tomishige, Keiichi
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p. 28664 - 28672
(2014/07/22)
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- Amination of alcohols with ammonia in water over Rhin catalyst
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Amination of various C3 alcohols such as 1,2-propanediol with ammonia was catalyzed by RhIn/C in water while Rh/C was totally inactive. Activated carbon FAC-10 was the best support in terms of activity and resistance to metal leaching. In the amination of 1,2-propanediol, RhIn/C produced amino alcohols in 68% total selectivity and 38% conversion. XRD and TEM measurements showed that RhIn alloy particle with size of 34 nm was formed on the carbon support.
- Takanashi, Tsukasa,Nakagawa, Yoshinao,Tomishige, Keiichi
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p. 822 - 824
(2014/06/23)
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- PROCESS FOR THE REDUCTION OF NITRO DERIVATIVES TO AMINES
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Disclosed is a novel process for the reduction of nitro groups to amino derivatives, based on the use of trichlorosilane and an organic base, which is efficient from the chemical standpoint and of wide general applicability.
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Page/Page column 6
(2014/03/26)
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- Electromagnetic actuator
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An electromagnetic actuator comprising a fixed magnetic pole (11) applied with an electromagnetic coil (14), and a movable magnetic pole (20) provided in the insertion hole (12) of the fixed magnetic pole movably in the axial direction. The movable magnetic pole is provided with a projecting portion (22) tapered along its moving direction, a recessed taper portion (13) corresponding to the projecting taper portion of the movable magnetic pole is formed at the insertion hole of the fixed magnetic pole, and a tubular auxiliary magnetic pole (40) extending in the axial direction from the opening end of the recessed taper portion is provided continuously to the fixed magnetic pole.
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- THIADIAZOLE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted thiadiazolyl, and R2, R3, R4, R5, R6, R7 and R8 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
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Page/Page column 18
(2010/06/22)
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- METHOD FOR PRODUCING AMINES FROM GLYCERIN
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The present invention relates to a process for preparing amines by reacting glycerol with hydrogen and an aminating agent from the group of ammonia and primary and secondary amines in the presence of a catalyst at a temperature of from 100° C. to 400° C. and a pressure of from 0.01 to 40 MPa (from 0.1 to 400 bar). Preference is given to using glycerol based on renewable raw materials. The catalyst preferably comprises one metal or a plurality of metals or one or more oxygen compounds of the metals of groups 8 and/or 9 and/or 10 and/or 11 of the Periodic Table of the Elements. The invention further relates to the use of the reaction products as an additive in cement or concrete production and in other fields of use. This invention further provides the compounds 1,2,3-triaminopropane, 2-aminomethyl-6-methylpiperazine, 2,5-bis(aminomethyl)piperazine and 2,6-bis(aminomethyl)piperazine.
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Page/Page column 12-13; 14
(2010/10/03)
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- Acid and base stable diphenylmethanol derivatives and methods of use
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The invention provides compounds that are useful as linkers for solid phase synthesis and as protecting groups, and methods for producing and using the same.
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Page/Page column 8-9
(2008/12/08)
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- Process for the conversion of glycerol to propylene glycol and amino alcohols
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Processes for the conversion of glycerol to a product mixture of an amino alcohol product and propylene glycol are disclosed. Glycerol is converted to hydroxyacetone and the hydroxyacetone is reduced with a reducing agent or reacted with an amine compound to give an adduct which is reduced using the reducing agent to obtain a product mixture of propylene glycol and an amino alcohol product.
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Page/Page column 12
(2008/06/13)
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- Method for producing optically active alcohols or carboxylic acids
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The present invention relates to a process for preparing optically active hydroxy-, alkoxy-, amino-, alkyl-, aryl- or chlorine-substituted alcohols or hydroxy carboxylic acids having from 3 to 25 carbon atoms or their acid derivatives or cyclization products by hydrogenating the correspondingly substituted optically active mono- or dicarboxylic acids or their acid derivatives in the presence of a catalyst whose active component consists of rhenium or of rhenium and comprises at least one further element having an atomic number of from 22 to 83, with the provisos that a. the at least one further element having an atomic number of from 22 to 83 is not ruthenium and b. in the case of the preparation of optically active 2-amino-, 2-chloro-, 2-hydroxy- and 2-alkoxy-1-alkanols by catalytically hydrogenating corresponding optically active 2-aminocarboxylic acids, 2-chlorocarboxylic acids, 2-hydroxycarboxylic acids and 2-alkoxycarboxylic acids or their acid derivatives, the at least one further element having an atomic number of from 22 to 83 is not palladium or platinum.
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- Hydrogenation method for producing optically active alcohols or carboxylic acids
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The present invention relates to a process for preparing optically active hydroxy-, alkoxy-, amino-, alkyl-, aryl- or chlorine-substituted alcohols or hydroxy carboxylic acids having from 3 to 25 carbon atoms or their acid derivatives or cyclization products by hydrogenating the correspondingly substituted optically active mono- or dicarboxylic acids or their acid derivatives in the presence of a catalyst whose active component comprises a noble metal selected from the group of the metals Pt, Pd, Rh, Ir, Ag, Au and at least one further element selected from the group of the elements: Sn, Ge, Mo, W, Ti, Zr, V, Mn, Fe, Co, Ni, Cu, Zn, Ga, In, Pb, Bi, Cr, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb and Lu.
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- New, convenient methods of synthesis and resolution of 1,2-amino alcohols
-
Oximes of α-keto esters are reduced to obtain the corresponding amino alcohols using NaBH4 in combination with I2, CH 3COOH, TiCl4, ZrCl4, COCl2, H 2SO4, and TMS-Cl in 60-85% yields. The racemic phenylglycinol, phenylalaninol, and 2-aminobutanol are resolved using dibenzoyl-L-tartaric acid to obtain enantiomeric samples of >98% ee.
- Periasamy, Mariappan,Sivakumar, Sangarappan,Reddy, Meda Narsi
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p. 1965 - 1967
(2007/10/03)
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- Isothiazolecarboxylic acid derivatives and their use as microbicides
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Novel isothiazolecarboxylic acid derivatives of the formula (I), in which A, Q, Z and k have the meanings mentioned in the specification, processes for the preparation of the new compounds and their use as microbicides.
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- Amino alcohol derivatives, method of producing said derivatives and medicaments containing them
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Compounds of formula I in which R1denotes hydrogen or methyl R2denotes lower straight-chained or branched alkyl with 1 to 10 carbon atoms R3denotes hydrogen or lower alkyl n denotes 0-12 R4denotes alkyl, alkenyl or alkinyl with 6 to 24 carbon atoms, processes for the production thereof as well as pharmaceutical agents containing these compounds for the treatment of osteoporosis.
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- Reduction of nonpolar amino acids to amino alcohols to enhance volatility for high-precision isotopic analysis
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Amino adds are routinely derivatized using carbon-containing groups prior to gas chromatography continuous-flow isotope ratio mass spectrometry (GCC-IRMS). Derivative C contaminates analyte C because the entire derivatized compound is eombusted to CO2. Correction procedures are required to extract the analyte isotope ratio. We present a method for reduction of six nonpolar amino adds to their corresponding amino alcohols, demonstrate a GC strategy to produce acceptable peak shapes from the resulting strongly H-bonding analytes, and present isotopic analysis for amino acids and their corresponding amino alcohols to evaluate any possible isotopic fractionation. Alanine, valine, leucine, isoleucine, methionine, or phenylalanine was reduced using NaBH4 in THF with Ia as an electrophile. Reactions were performed with 2 g of analyte to permit isotopic analysis by conventional elemental analysis-IRMS. All reactions were quantitative as assessed by IR spectra, melting points, and GC. Recovery from the reaction mixture was 60-84%. GC separation of a mixture of the six amino alcohols was achieved using a thick stationary-phase (5 μm) capillary column to avoid tailing due to hydrogen bonding to the walls of the fused-silica capillary. The reproducibility of GCC-IRMS determinations of amino alcohols averaged SD(δ13C) = 0.25 ± 0.19‰. The absolute differences between δ13C of amino acids measured by an elemental analyzer coupled to IRMS and amino alcohols measured by GCC-IRMS was Δδ13C = 0.14‰ and showed no general trend. Reactions performed with 2 mg of analyte yielded equivalent chromatograms. These data indicate that the reduction method does not induce isotopic fractionation and can be used for continuous-flow isotopic analysis to avoid addition of contaminating carbon.
- Zaideh,Saad,Lewis,Brenna
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p. 799 - 802
(2007/10/03)
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- Cytokine potentiator and pharmaceutical formulation for cytokine administration
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A cytokine activity enhancer comprising an ethanolamine derivative of the following general formula (I) or a salt thereof, or comprising it along with cytokine or a cytokine production promoter; and also a medicine for diseases with lowered cytokine activity, comprising, as the active ingredient, the cytokine activity enhancer: STR1 wherein R1 is H, --CH3, --CH2 CH(CH3)OH or --CH2 CH2 OH; R2 is H, --CH3, --CH2 CH3 or --COOH; and R3 is H, --CH3, --CH2 CH3 or --CH2 NH2.
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-
- Synthesis of 1,2-aminoalcohols by Ti(IV)-catalyzed photohydroxymethylation of chiral aldimines
-
The N-(α-phenylethyl) alkylated aldimines 3a-c are conveniently hydroxymethylated with moderate diastereoselectivities by means of irradiation in methanolic solution in the presence of titanium(IV)chloride.
- Griesbeck, Axel G.,Buhr, Stefan,Lex, Johann
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p. 2535 - 2536
(2007/10/03)
-
- Kinetic study of the reaction between iodide and N-chloramines
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We carried out a kinetic study of the reaction between iodide ion and various primary N-chloramines and found it to be first-order in the latter.Experiments also showed the rate constant for the reaction to be directly proportional to the iodide and hydrogen ion concentrations.The influence of the concentration reveals the presence of general acid catalysis processes.
- Antelo, J. M.,Arce, F.,Campos, J.,Parajo, M.
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p. 391 - 396
(2007/10/03)
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- Process for the preparation of arylimides of perylene-3,4,9,10-tetracarboxylic acid
-
Process for the preparation of compounds of the formula (1) STR1 in which R1 denotes a phenyl or naphthyl radical which can be substituted by alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro groups or halogen atoms, and R2 denotes a hydrogen atom or a phenyl or naphthyl radical which can be substituted by alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro groups or halogen atoms, or denotes an alkyl (C1 -C8) radical, by condensation, at between 100° C. and 300° C., of perylene-3,4,9,10-tetracarboxylic dianhydride or a monoanhydride monoimide of the formula (2) STR2 in which R2 has the abovementioned meaning, with an arylamine of the formula (3) in which R1 has the abovementioned meaning, in the presence of dialkylamines of the formula (4) STR3 in which R' and R denote straight-chain alkyl C1- C6 or branched alkyl C3-C6 or cycloalkyl C5-C6 groups, which can be substituted by hydroxyl, alkoxy C1-C4, alkyl C1-C4 amino, or phenyl or naphthyl groups which can be substituted on the aromatic nucleus by alkyl C1-C4, alkoxy C1-C4 or alkyl C1-C4 -amino groups or halogen atoms, and in which R' and R can form with the nitrogen atom a 5- or 6-membered heterocyclic ring.
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- Poly-bis-triazinylimides, their preparation
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Poly-bis-triazinylimides of the formula STR1 are prepared from bis-(2,4-dichloro-1,3,5-triazin-6-yl)imides and polyalkylpiperidylamines. They are used as light stabilizers for polymers.
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- FORMATION OF AMINO ACIDS FROM ALIPHATIC AMINES BY CONTACT GLOW DISCHARGE ELECTROLYSIS
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Oxidation of aliphatic amines in an aqueous solution by contact glow discharge electrolysis resulted in the formation of several amino acids, which was explained by the oxidative action of hydroxyl radical generated by the electric discharge process to the aqueous solution.
- Harada, Kaoru,Nomoto, Masayo M.,Gunji, Hiromi
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p. 769 - 772
(2007/10/02)
-
- Asymmetric Hydroformylation and Hydrocarboxylation of Enamides. Synthesis of Alanine and Proline
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Carbonyltris(triphenylphosphine)hydridorhodium (1) catalyzed the hydroformylation of N-vinylimides in the presence of optically active 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (DIOP) or 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(5H-dibenzophospholyl)butane (DIPHOL) to afford optically active α-amido aldehydes.Linear disubstituted N-vinylimides or -amides reacted very sluggishly, while the cyclic N-acyl-2-pyrroline (19) was very reactive.In the unsubstituted N-vinylimides moderate (20-40percent ee) asymmetric induction was observed.The optically active α-amido aldehydes were readily converted to the corresponding α-amino acids.Asymmetric hydrocarboxylation of the same substrates in the presence of bis(triphenylphosphine)palladium chloride (2) produced α-amido esters in low optical purity.
- Becker, Y.,Eisenstadt, A.,Stille, J. K.
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p. 2145 - 2151
(2007/10/02)
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