- Microwave-Assisted Method for the Synthesis of Perylene Ester Imides as a Gateway Toward Unsymmetrical Perylene Bisimides
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A high yielding microwave-assisted synthetic method to obtain unsymmetrical perylene diester monoimide (PEI) by treating the perylene tetrester (PTE) with a requisite amine is reported. Perylene-based molecules are widely used in the construction of self-assembled supramolecular structures because of their propensity to aggregate under various conditions. In comparison to perylene bisimides (PBIs), PEIs are less studied in organic electronics/self-assembly due to the synthetic difficulty and low yields in their preparation. PEIs are less electron deficient and have an unsymmetric structure in comparison to PBIs. Further, the PEIs have a higher solubility than PBIs. The present method is applicable with a wide range of substrates like aliphatic, aromatic, benzyl amines, PTEs, and bay-annulated PTEs. This method provides a tuning handle for the optical/electronic properties of perylene derivatives and also provides an easy access to unsymmetrical PBIs from the PEIs.
- Gupta, Ravindra Kumar,Achalkumar, Ammathnadu S.
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- Non-Cryogenic, Ammonia-Free Reduction of Aryl Compounds
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A method of reducing an aromatic ring or a cyclic, allylic ether in a compound includes preparing a reaction mixture including a compound including an aromatic moiety or a cyclic, allylic ether moiety, an alkali metal, and either ethylenediamine, diethylenetriamine, triethylenetetramine, or a combination thereof, in an ether solvent; and reacting the reaction mixture at from ?20° C. to 30° C. for a time sufficient to reduce a double bond in the aromatic moiety to a single bond or to reduce the cyclic, allylic ether moiety.
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- Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
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The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
- Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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p. 3115 - 3125
(2019/04/26)
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- Photochemical Cleavage of Benzylic C-N Bond to Release Amines
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The 3-(diethylamino)benzyl (DEABn) group has been studied for releasing primary, secondary, and tertiary amines by direct photochemical breaking of the benzylic C-N bond. While photochemical release of primary and secondary amines provides high yields in
- Wang, Pengfei,Devalankar, Dattatray A.,Lu, Wenya
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p. 6195 - 6200
(2016/08/16)
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- Reduced reactivity of amines against nucleophilic substitution via reversible reaction with carbon dioxide
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The reversible reaction of carbon dioxide (CO2) with primary amines to form alkyl-ammonium carbamates is demonstrated in this work to reduce amine reactivity against nucleophilic substitution reactions with benzophenone and phenyl isocyanate. The reversible formation of carbamates has been recently exploited for a number of unique applications including the formation of reversible ionic liquids and surfactants. For these applications, reduced reactivity of the carbamate is imperative, particularly for applications in reactions and separations. In this work, carbamate formation resulted in a 67% reduction in yield for urea synthesis and 55% reduction for imine synthesis. Furthermore, the amine reactivity can be recovered upon reversal of the carbamate reaction, demonstrating reversibility. The strong nucleophilic properties of amines often require protection/de-protection schemes during bi-functional coupling reactions. This typically requires three separate reaction steps to achieve a single transformation, which is the motivation behind Green Chemistry Principle #8: Reduce Derivatives. Based upon the reduced reactivity, there is potential to employ the reversible carbamate reaction as an alternative method for amine protection in the presence of competing reactions. For the context of this work, CO2 is envisioned as a green protecting agent to suppress formation of n-phenyl benzophenoneimine and various n-phenyl-n-alky ureas.
- Mohammed, Fiaz S.,Kitchens, Christopher L.
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- NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions
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A series of seven novel NImNHP-type pincer imidazolylphosphine ruthenium complexes has been synthesized and fully characterized. The use of hydrogenation of benzonitrile as a benchmark test identified [RuHCl(CO)(NImNHPtBu)] as the most active catalyst. With its stable Ru-BH4 analogue, in which chloride is replaced by BH4, a broad range of (hetero)aromatic and aliphatic nitriles, including industrially interesting adiponitrile, has been hydrogenated under mild and base-free conditions.
- Adam, Rosa,Alberico, Elisabetta,Baumann, Wolfgang,Drexler, Hans-Joachim,Jackstell, Ralf,Junge, Henrik,Beller, Matthias
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p. 4991 - 5002
(2016/04/05)
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- A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands
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A novel protocol for the general hydrogenation of nitriles in the absence of basic additives is described. The system is based on the combination of [Ru(cod)(methylallyl)2] (cod=cyclooctadiene) and L2. A variety of aromatic and aliphatic nitriles is hydrogenated under mild conditions (50 °C and 15 bar H2) with this system. Kinetic studies revealed higher activity in the case of aromatic nitriles compared with aliphatic ones.
- Adam, Rosa,Bheeter, Charles Beromeo,Jackstell, Ralf,Beller, Matthias
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p. 1329 - 1334
(2016/04/20)
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- A protic ionic liquid catalyzed strategy for selective hydrolytic cleavage of tert-butyloxycarbonyl amine (N-Boc)
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A simple, mild and efficient strategy for selective hydrolytic cleavage of the N-tert-butyloxycarbonyl (Boc) group is devised using a protic ionic liquid as an efficient catalyst. The deprotection reaction proceeded well for N-Boc protected aromatic, heteroaromatic, aliphatic compounds, and chiral amino acid esters and peptides. A wide range of labile protecting groups such as tert-butyl ester, tert-butyl ether, benzyloxycarbonyl (Cbz), TBDMS, O-Boc and S-Boc remained unaffected under the reaction conditions. This journal is
- Majumdar, Swapan,De, Jhinuk,Chakraborty, Ankita,Roy, Dipanwita,Maiti, Dilip K.
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p. 3200 - 3205
(2015/02/03)
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- NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
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Page/Page column 75
(2016/05/02)
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- Synthesis of Pt dendritic nanocubes with enhanced catalytic properties
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Pt dendritic nanocubes (DNCs) were successfully synthesized in oleylamine under a 1 bar H2 atmosphere. The catalytic activity of Pt DNCs was much greater than conventional Pt nanoparticles (NPs) for the methanol electrooxidation reaction. Pt DNCs also showed excellent catalytic performance in the hydrogenation of unsaturated hydrocarbons and nitrobenzene.
- Xie, Ruigang,Pan, Yue,Gu, Hongwei
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p. 16497 - 16500
(2015/03/04)
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- Chemoselective N-deacetylation under mild conditions
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A mild and efficient chemoselective N-deacetylation using the Schwartz reagent at room temperature in rapid time is described. The mild and neutral conditions enable orthogonal N-deacetylation in the presence of some of the common protecting groups (viz. Boc, Fmoc, Cbz, Ts). The deprotection conditions did not induce any epimerization at the chiral amino centre.
- Sultane, Prakash R.,Mete, Trimbak B.,Bhat, Ramakrishna G.
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supporting information
p. 261 - 264
(2014/01/06)
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- Lipophilic chelates and their use in imaging
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The invention relates to chelate compounds which can be used in MRI, the chelates being intended to be conveyed by lipophilic transporters, such as lipid nanoparticles or liposomes. The invention also relates to compounds comprising, in association, these chelates and these transporters, if appropriate connected via chemical bonding groups, and to their use in diagnostic imaging, it being possible for this association additionally to comprise biological targeting markers, denoted biovectors.
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Page/Page column 42; 44
(2012/09/25)
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- Ceric ammonium nitrate-mediated detritylation of tritylated amines
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Efficient deprotection of tritylated amines to the corresponding amines mediated by 20 mol % ceric ammonium nitrate [Ce(NH4) 2(NO3)6, CAN], 10 equiv of acetic acid and 15 equiv of water in dichloromethane is presented. This method equally worked well in the case of morpholino nucleosides.
- Pattanayak, Sankha,Sinha, Surajit
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experimental part
p. 34 - 37
(2011/02/25)
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- PROCESS FOR PRODUCTION OF NITROGENATED COMPOUND
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The present invention relates to a process for producing an aliphatic primary amine or an aliphatic secondary amine from an aliphatic alcohol with a high catalytic activity and a high selectivity. In the process for producing an aliphatic amine according to the present invention, a linear, branched, or cyclic aliphatic alcohol having 6 to 22 carbon atoms is contacted with ammonia and hydrogen in the presence of a catalyst formed by supporting a ruthenium component on at least one material selected from the group consisting of (B) a zirconia-containing composite oxide and (C) zirconia surface-treated with a metal by hydrolysis of (A) a ruthenium compound.
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Page/Page column 7
(2009/10/01)
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- PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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The present invention relates to a process for producing an aliphatic amine, including the step of contacting a linear or branched, or cyclic aliphatic alcohol with ammonia and hydrogen in the presence of a catalyst containing (A) nickel, copper and zirconium components, and (B) at least one metal component selected from the group consisting of elements belonging to Group 3 of the Periodic Table, elements belonging to Group 5 of the Periodic Table and platinum group elements. According to the process of the present invention, an aliphatic primary amine can be produced from an aliphatic alcohol with a high selectivity.
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Page/Page column 4
(2008/06/13)
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- PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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The present invention relates to a process for producing an aliphatic amine, including the step of contacting a linear or branched, or cyclic aliphatic alcohol with ammonia and hydrogen in the presence of a catalyst containing (A) nickel, copper and zirconium components, and (B) at least one metal component selected from the group consisting of elements belonging to Group 1 of the Periodic Table. According to the process of the present invention, an aliphatic primary amine can be produced from the aliphatic alcohol with a good yield and a high productivity.
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Page/Page column 4
(2008/06/13)
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- PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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The present invention relates to a process for producing an aliphatic amine, comprising the step of contacting a linear or branched, or cyclic aliphatic alcohol having 6 to 22 carbon atoms with ammonia and hydrogen in the presence of a catalyst formed by supporting at least (A) a ruthenium component produced by hydrolysis of a ruthenium compound on a carrier, or by further supporting, in addition to the component (A), a specific second metal component or a specific third metal component on the carrier. According to the process of the present invention, an aliphatic primary amine can be produced from an aliphatic alcohol with a high catalytic activity and a high selectivity.
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Page/Page column 10-11
(2008/06/13)
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- Method of producing aliphatic nitrile
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The present invention relates to a method of producing an aliphatic nitrile by reacting an aliphatic carboxylic acid, by reacting an aliphatic dicarboxylic acid or their alkyl esters (the alkyl group with 1 to 5 carbon atoms) with ammonia in the presence of a catalyst of titanium oxide supported on solid silica. In addition, the present invention relates to a method of producing an aliphatic amine, including hydrogenating the aliphatic nitrile by using a hydrogenating catalyst and a catalyst for producing an aliphatic nitrile.
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Page/Page column 5
(2008/06/13)
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- Wetting agent composition for agricultural chemicals
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The present invention provides an agrochemical spreader composition having excellent low-temperature stability. Specifically, the present invention provides an agrochemical spreader composition comprising a surfactant (A) having a melting point of 20 to 60° C., a surfactant (B) having a melting point of not more than 0° C. and water in a specific ratio.
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- Process for producing a primary amine compound
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The present invention relates to a process for producing both of a primary amine compound and an alkylene oxide adduct thereto, given that the both are excellent in color, with high yield. That is, the process comprises hydrogenating a nitrile compound in the presence of a Raney catalyst comprising 90 to 96% by weight of Ni, 3 to 9% by weight of Al and 0.5 to 3% by weight of Mo being based on the total of the atoms of Ni, Al and Mo to obtain the primary amine compound. Further, an alkylene oxide may be added thereto to obtain an alkylene oxide adduct to the primary amine compound.
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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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- Very Soluble and Photostable Perylene Fluorescent Dyes
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The synthesis of perylene dyes 2 with two terminal alkyl groups is described.Long-chain alkyl groups do not increase, but diminish solubility.Cycloalkyl substituents give a minimum of solubility with medium sized rings and a maximum with the cyclotetradecyl derivative (2p).Very high solubility in organic solvents is attained by substitution with secondary alkyl residues having two long chains.One of them, the dye with the 1-hexylheptyl substituent (2v), exhibits a solubility of more than 100g/l in most solvents, a fluorescent quantum yield of about 100 percent, and a very high photostability, thus making it suitable for special applications.
- Demming, Stefan,Langhals, Heinz
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p. 225 - 230
(2007/10/02)
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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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- Thermal, Dielectric and Polarized Microscopy Studies of 1-Octadecylamine
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Measurements of the physical properties of 1-octadecylamine were carried out in a temperature range of 30 to 120 deg C.The melting point of the compound was observed at 55 deg C and no liquid crystalline phase was found within this temperature range.The decomposition point of the carbonate of this amine was found to be a little higher than the melting point.A mixture of the amine with a small amount of its carbonate gave DSC curve similar to that of typical liquid crystalline materials.
- Nakamura, Naotake,Okada, Masao,Okada, Yutaka,Sugita, Kaichiro
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p. 181 - 186
(2007/10/02)
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- Process for hydrogenation of nitriles
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A novel process is described for the homogeneous hydrogenation of nitriles to primary amines utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the high yield hydrogenation of nitriles to primary amines to be conducted under mild conditions of temperature and pressure with high selectivity and eliminates the need for the presence of ammonia to suppress the formation of significant amounts of secondary and tertiary amines.
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- Anionic metal hydride catalysts. 2. Application to the hydrogenation of ketones, aldehydes, carboxylic acid esters, and nitriles
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The application of the potassium hydrido(phosphine)ruthenate complexes K+[(Ph3P)2Ph2-PC6H 4RuH2]-·C10H 8·(C2H5)2O (1) and K2+[(Ph3P)3(Ph2P)Ru 2H4]2-·2C6H 14O3 (2) as catalysts for the homogeneous phase hydrogenation of a variety of unsaturated organic compounds is described. Ketones and aldehydes are catalytically hydrogenated with 1 and 2 typically at 85°C and under 620 kPa of hydrogen, to yield the corresponding alcohols as well as minor aldol condensation byproducts. The hydrogenation of acrolein, depending on conditions, can give either propionaldehyde or mixtures of propionaldehyde and allyl alcohol. Carboxylic acid esters, which are activated by adjacent electron-withdrawing groups, e.g., CF3CO2CH3, CF3CO2CH2CF3, (-CO2CH3)2, can be hydrogenated, with 1 and 2, to yield, respectively, CF3CH2OH and CH3OH, CF3CH2OH, and HOCH2CO2CH3. Methyl acetate diluted with toluene (1:10 (v/v)) in the presence of 2 is hydrogenated (at 90°C, under 620 kPa of H2) giving methanol, ethanol, and ethyl acetate (formed by trans-esterification with the ethanol product). This represents the first instance of a homogeneous catalytic hydrogenation of a simple aliphatic ester. Nitriles are hydrogenated with 1 and 2 (at 90°C, 620 kPa of H2) to give, selectively, primary amines. The rates and achievable conversions for these reactions are dependent upon the solvent medium used and on the nature of the cation associated with the hydridometalate catalysts.
- Grey, Roger A.,Pez, Guido P.,Wallo, Andrea
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p. 7536 - 7542
(2007/10/02)
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