- Multi-enzymatic cascade reactions with Escherichia coli-based modules for synthesizing various bioplastic monomers from fatty acid methyl esters?
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Multi-enzymatic cascade reaction systems were designed to generate biopolymer monomers using Escherichia coli-based cell modules, capable of carrying out one-pot reactions. Three cell-based modules, including a ω-hydroxylation module (Cell-Hm) to convert fatty acid methyl esters (FAMEs) to ω-hydroxy fatty acids (ω-HFAs), an amination module (Cell-Am) to convert terminal alcohol groups of the substrate to amine groups, and a reduction module (Cell-Rm) to convert the carboxyl groups of fatty acids to alcohol groups, were constructed. The product-oriented assembly of these cell modules involving multi-enzymatic cascade reactions generated ω-ADAs (up to 46 mM), α,ω-diols (up to 29 mM), ω-amino alcohols (up to 29 mM) and α,ω-diamines (up to 21 mM) from 100 mM corresponding FAME substrates with varying carbon chain length (C8, C10, and C12). Finally 12-ADA and 1,12-diol were purified with isolated yields of 66.5% and 52.5%, respectively. The multi-enzymatic cascade reactions reported herein present an elegant ‘greener’ alternative for the biosynthesis of various biopolymer monomers from renewable saturated fatty acids.
- Jung, Hyunsang,Kim, Byung-Gee,Kim, Ye Chan,Park, Beom Gi,Patil, Mahesh D.,Sarak, Sharad,Yoo, Hee-Wang,Yun, Hyungdon
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p. 2222 - 2231
(2022/04/03)
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- Method for preparing organic diamine from amino nitrile organic matter
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The invention provides a method for preparing organic diamine from an amino nitrile organic matter, which comprises the following steps: (1) reacting the amino nitrile organic matter with hydrogen in a solvent under the action of a catalyst to obtain a reacted material containing the organic diamine; (2) refining the reacted material to obtain crude organic diamine; and (3) adsorbing and purifying the crude organic diamine to obtain the purified organic diamine. According to the method, the amino nitrile organic matter reacts with hydrogen, the reaction selectivity and the conversion rate are high, and the high-purity organic diamine product can be obtained in the subsequent purification mode of combining refining and adsorption purification.
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Paragraph 0240; 0246-0248; 0290-0291
(2021/10/02)
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- Imprinted Apportionment of Functional Groups in Multivariate Metal-Organic Frameworks
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Sophisticated chemical processes widely observed in biological cells require precise apportionment regulation of building units, which inspires researchers to develop tailorable architectures with controllable heterogeneity for replication, recognition and information storage. However, it remains a substantial challenge to endow multivariate materials with internal sequences and controllable apportionments. Herein, we introduce a novel strategy to manipulate the apportionment of functional groups in multivariate metal-organic frameworks (MTV-MOFs) by preincorporating interlocked linkers into framework materials. As a proof of concept, the imprinted apportionment of functional groups within ZIF-8 was achieved by exchanging imine-based linker templates with original linkers initially. The removal of linker fragments by hydrolysis can be achieved via postsynthetic labilization, leading to the formation of architectures with controlled heterogeneity. The distributions of functional groups in the resulting imprinted MOFs can be tuned by judicious control of the interlocked chain length, which was further analyzed by computational methods. This work provides synthetic tools for precise control of pore environment and functionality sequences inside multicomponent materials.
- Feng, Liang,Wang, Kun-Yu,Lv, Xiu-Liang,Powell, Joshua A.,Yan, Tian-Hao,Willman, Jeremy,Zhou, Hong-Cai
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supporting information
p. 14524 - 14529
(2019/10/02)
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- Corresponding amine nitrile and method of manufacturing thereof
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The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.
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Paragraph 0152
(2018/05/24)
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- Corresponding amine nitrile and method of manufacturing thereof (by machine translation)
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The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.
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Paragraph 0152
(2018/07/15)
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- Corresponding amine nitrile and method of manufacturing thereof
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The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.
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Paragraph 0150; 0153
(2018/07/15)
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- Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines
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Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the other hand after deamination to benzaldehyde also as oxidant. All ω-HFAs tested were efficiently transformed to their corresponding ω-AmFAs using purified enzymes as well as a whole-cell system, separately expressing both the enzymes, with conversions ranging from 80-95%. Additionally, a single-cell co-expressing all enzymes successfully produced the ω-AmFAs as well as the α,ω-diamines with >90% yield. This system was extended by employing a lactonase, enabling the transformation of ?-caprolactone to its corresponding ω-AmFA with >80% conversion.
- Sung, Sihyong,Jeon, Hyunwoo,Sarak, Sharad,Ahsan, Md Murshidul,Patil, Mahesh D.,Kroutil, Wolfgang,Kim, Byung-Gee,Yun, Hyungdon
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supporting information
p. 4591 - 4595
(2018/10/23)
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- Diamine compound (by machine translation)
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[Problem] to obtain, dicyano compound is reacted with hydrogen, resulting diamine compound impurities contained in elucidating structure, the impurity content is reduced, a high purity in a high yield in an industrially suitable method for producing a diamine compound. [Solution] nickel catalyst in the presence of a basic compound, a compound represented by general formula (1) is reacted with hydrogen shown dicyano, method for producing a diamine compound, a diamine compound represented by general formula (3) contained in the obtained amide compound content of 0.5% or less as measured by gas chromatography indicated by the area of the, the diamine compound. (1) NC-a Z-to-CN(Z may, of 1 - 20 carbon atoms of straight-chain alkylene group, an alkylene group of a carbon number of 3 - 20 annular, or branched alkylene group of a carbon number of 3 - 20. )(Z is, the synonymous. )[Drawing] no (by machine translation)
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Paragraph 0091-0094
(2017/07/26)
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- A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines
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A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/triphos catalyst is reported. Excellent conversions and yields are obtained under optimised reaction conditions. The reactions worked very well using 1,4-dioxane as solvent, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. This method provides a potential route to converting waste biomass to value added materials. The reaction is proposed to go through both amide and aldehyde pathways.
- Shi, Yiping,Kamer, Paul C. J.,Cole-Hamilton, David J.
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supporting information
p. 5460 - 5466
(2017/11/22)
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- Cavitands as Reaction Vessels and Blocking Groups for Selective Reactions in Water
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The majority of reactions currently performed in the chemical industry take place in organic solvents, compounds that are generally derived from petrochemicals. To promote chemical processes in water, we examined the use of synthetic, deep water-soluble cavitands in the Staudinger reduction of long-chain aliphatic diazides (C8, C10, and C12). The diazide substrates are taken up by the cavitand in D2O in folded, dynamic conformations. The reduction of one azide group to an amine gives a complex in which the substrate is fixed in an unsymmetrical conformation, with the amine terminal exposed and the azide terminal deep and inaccessible within the cavitand. Accordingly, the reduction of the second azide group is inhibited, even with excess phosphine, and good yields of the monofunctionalized products are obtained. In contrast, the reduction of the free diazides in bulk solution yields diamine products.
- Masseroni, Daniele,Mosca, Simone,Mower, Matthew P.,Blackmond, Donna G.,Rebek, Julius
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p. 8290 - 8293
(2016/07/19)
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- TRANSFORMATION OF PEROXYACETAL INTERMEDIATE
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A method for transforming a compound of formula IIa: to a compound of formula III: is provided, wherein A is a C6-C10 alkene chain with at least one double bond, R1 is a C1-C10 alkyl, and R3 is an oxygen-containing functional group.
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- ACYCLIC ALKENES VIA OZONOLYSIS OF MULTI-UNSATURATED CYCLOALKENES
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A method of making a compound of formula (IIa) by selective ozonolysis of a compound of formula (I) is provided, wherein A is a C6-C10 alkene chain with at least one double bond, R1 is a C1-C10 alkyl, and R3 is an oxygen-containing functional group.
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- PREPARATION OF PRIMARY DIAMINES HAVING A LINEAR MAIN CHAIN FOR POLYAMIDE SYNTHESES
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The invention provides a method to produce primary diamines by catalytic conversion of diols having a linear main chain of from 4 to 31 carbon atoms into the corresponding diamines. The reaction is conducted in a liquid or supercritical phase and is catalyzed by a homogeneous ruthenium-containing complex. The primary diamines obtained may be suitable for polyamide syntheses.
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Page/Page column 4
(2012/08/27)
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- Functionalized Photoreactive Compounds
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The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.
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- Efficient transformation of azides to primary amines using the mild and easily accessible CeCl3·;7H2O/NaI system
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(Chemical Equation Presented) Because of the nitrogen functionality, the azido group plays an important role in the synthesis of amines, and numerous reduction methods of azides to primary amines are reported. Recent reports have highlighted the capability of NaI as a useful reagent for this transformation when it is used in combination with a Lewis acid promoter. However, these methods often suffer from harsh reaction conditions; for this reason, the development of a simple and efficient protocol using NaI in presence of inexpensive and readily available cerium salts Lewis acids would extend the scope of this organic transformation. In continuation of our interest on the use of the CeCl3·7H2O/NaI system, in this paper we report how azides undergo reduction by NaI in the presence of CeCl 3·7H2O in refluxing acetonitrile under neutral conditions to produce the corresponding primary amines. The rate and yield of the reaction are considerably improved by employing this microwave-assisted procedure, and this may be of value for the preparation of densely functionalized molecules having biological and pharmaceutical activities.
- Bartoli, Giuseppe,Di Antonio, Giustino,Giovannini, Riccardo,Giuli, Sandra,Lanari, Silvia,Paoletti, Melissa,Marcantoni, Enrico
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p. 1919 - 1924
(2008/09/18)
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- NMR Detection of Simultaneous Formation of [2]- and [3]Pseudorotaxanes in Aqueous Solution between α-Cyclodextrin and Linear Aliphatic α,ω-Amino acids, an α,ω-Diamine and an α,ω-Diacid of Similar Length, and Comparison with the Solid-State Structures
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The interactions of 11-aminoundecanoic acid (1), 12-aminododecanoic acid (2), 1,12-diaminododecane (3), and 1,13-tridecanoic diacid (4) with α-cyclodextrin (αCD) were studied in aqueous solution by NMR spectroscopy. The association modes were established with titration and continuous variation plots, variable temperature NMR spectra, and dipolar interactions as recorded in 2D ROESY spectra. The studies were carried out at pH 7.3 and 13.6. These long, linear bifunctional molecules were found to form simultaneously [2]- and [3]pseudorotaxanes with αCD in the aqueous solution. At the higher pH the 1:1 adducts were present at concentrations higher than at the neutral pH. The longer guests formed complexes enriched in the 2:1 constituent at both pH values. There were clear indications that the [2]pseudorotaxanes are present in two isomeric forms. The presence of isomers also in the [3]pseudorotaxanes was not ruled out. Various exchange rate regimes were observed; clearly in neutral solutions the formation of the 1:1 complexes was fast in the NMR time scale, whereas the threading of a second αCD ring was a slower process. In the solid state, the adduct of αCD/2 had the structure of a [3]pseudorotaxane, in accordance with previously solved crystal structures of αCD/3 and βCD/4. The species in solution, in contrast with those present in the solid state, are therefore of varying nature, and thus the frequently and conveniently assumed 1:1 stoichiometry in similar systems is an oversimplification of the real situation.
- Eliadou, Kyriaki,Yannakopoulou, Konstantina,Rontoyianni, Aliki,Mavridis, Irene M.
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p. 6217 - 6226
(2007/10/03)
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- Process for preparing primary amines from aldehydes
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Process for preparing primary amines from aldehydes by mixing an aldehyde with a diluent, where in the case of an alcohol or of water as diluent the mixing temperature is at most 5° C. to prevent the formation of the hemiacetal or the aldehyde hydrate, and bringing the mixture into contact with a mixture of ammonia, hydrogen and hydrogenation catalyst, whereby the formation of an imine is prevented, at temperatures of from 60° to 180° C. and pressures of from 20 to 60 bar, at least 15 mol of ammonia being used per mol of aldehyde group, and also an apparatus for carrying out the process.
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- Process for preparing 1-oxa-3,8-diaza-4-oxo-spiro-[4,5]-decanes
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1-Oxa-3,8-diaza-4-oxo-spiro-[4,5]-decane compounds of the formula STR1 are new light stabilizers for protecting polymers from the damaging effect of UV radiation.
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- Triazine derivatives
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The invention relates to polymers of triazine compounds containing piperidine groups which may serve as low volatile and migration-resistant light stabilizers for synthetic polymers. They have the structure STR1 and are obtained from cyanuric halides, diamines and polyalkylpiperidylamino compounds.
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