- Ru/g-C3N4as an efficient catalyst for selective hydrogenation of aromatic diamines to alicyclic diamines
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A series of Ru/g-C3N4materials with highly dispersed Ru were firstly prepared by an ultrasonic impregnation method using carbon nitride as a support. The catalysts were characterized by various techniques including BET and elemental analysis, ICP-AES, XPS, XRD, CO2-TPD and TEM. The results demonstrated that Ru/g-C3N4materials with a mesoporous structure and highly dispersed Ru were successfully prepared. The chemo-selective hydrogenation ofp-phenylenediamine (PPDA) to 1,4-cyclohexanediamine (CHDA) over Ru/g-C3N4as a model reaction was investigated in detail. PPDA conversion of 100% with a CHDA selectivity of more than 86% could be achieved under mild conditions. It can be inferred that the carbon nitride support possessed abundant basic sites and the Ru/g-C3N4-Tcatalysts provided suitable basicity for the aromatic ring hydrogenation. Compared to the N-free Ru/C catalyst, the involvement of nitrogen species in Ru/g-C3N4remarkably improved the catalytic performance. In addition, the recyclability of the catalyst demonstrated that the aggregation of Ru nanoparticles was responsible for the decrease of the catalytic activity. Furthermore, this strategy also could be expanded to the selective hydrogenation of other aromatic diamines to alicyclic diamines.
- Cao, Junya,Cao, Yan,Chen, Jiaqiang,Han, Fenggang,He, Peng,Huang, Xiaoyu,Li, Huiquan,Wang, Liguo,Yang, Huanhuan
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p. 16515 - 16525
(2020/05/13)
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- Method for preparing aliphatic amine through reduction of aromatic amine compound
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The invention provides a method for preparing aliphatic amine through reduction of an aromatic amine compound. According to the method, the aromatic amine compound is taken as a reaction substrate, and is subjected to hydrogenation reaction with a supported ruthenium catalyst and a deamination retardant in a solvent, so that an aliphatic amine compound is obtained; the deamination retardant adoptsaluminum-containing inorganic salt. The method has the advantages that through the addition of the deamination retardant during catalytic hydrogenation reduction of aromatic amine, the frequency of deamination side reaction produced by target products is reduced, so that the yield of the target products is improved, and the production cost of the specific yield of the target products is reduced.By taking the preparation of PACM as an example, the yield of the target product PACM can reach greater than 98 percent, and the preparation method has an important application value for practical mass production in the industry.
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Paragraph 0033-0059; 0066-0071
(2018/07/30)
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- 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol, and preparation method and application thereof
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The invention provides 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol, and a preparation method and an application thereof. According to the method, 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol is synthesized by reaction of a byproduct 4-((4-cyclohexylamino)methyl)cyclohexanol in an HMDA reaction process with formaldehyde and hydrogen under the action of a catalyst. The obtained 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol is purified and then can be used as a reactive catalyst for polyurethane foaming. The HMDA by-product is effectively utilized, the production cost is greatly reduced and resources are rationally utilized. 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol as the novel reactive catalyst is used for preparing polyisocyanurate/polyurethane and the like,has the characteristics of low odor and strong yellowing resistant ability, and the product has low VOC.
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Paragraph 0050-0052
(2018/10/04)
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- CATALYST AND METHOD FOR HYDROGENATION OF 4,4'-METHYLENEDIANILINE
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Disclosed is a catalyst for hydrogenation of 4,4′-methylenedianiline (MDA), including a support, a magnesium-aluminum oxide layer covering the support, and a rhodium-ruthenium active layer loaded on the magnesium-aluminum oxide layer, wherein the rhodium and the ruthenium of the rhodium-ruthenium active layer have a weight ratio of 40:60 to 10:90. The hydrogenation catalyst can be collocated with hydrogen for hydrogenation of the MDA to form bis(para-amino cyclohexyl) methane (PACM), and the PACM contains O mol % to 25 mol % of (t,t)-isomer.
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Page/Page column 0018
(2016/06/28)
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- METHOD FOR PRODUCING (4-AMINOBENZYL) CYCLOHEXYLAMINE
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PROBLEM TO BE SOLVED: To industrially produce (4-aminobenzyl) cyclohexylamine as a main product. SOLUTION: An aromatic ring hydrogenation reaction of methylenedianiline is performed with a catalyst comprising metal selected from the group consisting of rhodium, ruthenium, palladium, iridium, nickel, and cobalt under the condition of a hydrogen pressure in a reaction vessel of less than 5 MPa. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0028
(2017/05/26)
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- Catalyst and process for hydrogenating aromatics
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The present invention relates to an eggshell catalyst comprising an active metal selected from the group consisting of ruthenium, rhodium, palladium, platinum and mixtures thereof, applied to a support material comprising silicon dioxide, wherein the pore volume of the support material is 0.6 to 1.0 ml/g, determined by Hg porosimetry, the BET surface area is 280 to 500 m2/g, and at least 90% of the pores present have a diameter of 6 to 12 nm, to a process for preparing this eggshell catalyst, to a process for hydrogenating an organic compound which comprises at least one hydrogenatable group using the eggshell catalyst, and to the use of the eggshell catalyst for hydrogenating an organic compound.
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Page/Page column 21
(2015/07/27)
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- PROCESS FOR HYDROGENATING AROMATIC DI- AND POLYAMINES
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A catalytic process for hydrogenating aromatic di- and polyamines with the aid of a selected catalyst system is provided, which comprises a mixture of a first heterogeneous catalyst and a second heterogeneous catalyst and a nitro compound (nitrate and/or nitrite salt). The first and second heterogeneous catalyst each independently comprise a metal selected from the group consisting of Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and/or Pt and the metal selected for the second heterogeneous catalyst is different from the metal selected for the first heterogeneous catalyst. Hydrogenation of aromatic rings having two or more amino groups bound to the aromatic ring produces cycloaliphatic di- and polyamines, which are useful chemical intermediates, e.g., for further reaction with epoxides or isocyanates. The amino groups may also be converted to isocyanates via reaction with phosgene. The resulting cycloaliphatic di- and polyisocyanates may also be used as monomers for making polymers.
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Paragraph 0104; 0147
(2015/09/22)
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- One pot catalytic NO2 reduction, ring hydrogenation, and N-alkylation from nitroarenes to generate alicyclic amines using Ru/C-NaNO 2
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A report to produce alicyclic amines and subsequent N-alkylation with alcohols using Ru/C-NaNO2 catalyzed facile transformation of nitrobenzene was investigated. Effects of solvent, temperature, pressure, reaction time, and molar-ratio of substrate/catalyst on product composition were also studied. These mechanistic studies explain that nitrobenzene undergoes hydrogenation reaction in the following order; -NO2 reduction to -NH2, aromatic ring-hydrogenation to alicyclic, and from the reaction of alcohol to give N-alkylated amines. This investigation shed lights on possible application to polyurethane chemistry since these amines are used as important precursors for diisocyanates.
- Oh, Seung Geun,Mishra, Vivek,Cho, Jin Ku,Kim, Baek-Jin,Kim, Hoon Sik,Suh, Young-Woong,Lee, Hyunjoo,Park, Ho Seok,Kim, Yong Jin
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- METHOD OF CONVEYING LIQUIDS
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The present invention relates to a method of continuously conveying a liquid which is used as starting material in a chemical reaction by means of a displacement pump having physically separate forward-transport valves and a liquid-filled bidirectional flow line between displacement pump and forward-transport valves, wherein an auxiliary liquid which is a product or a starting material of the chemical reaction and has a melting point which is below the melting point or below the saturation temperature of the liquid to be conveyed is present in the bidirectional flow line. The present invention additionally provides for the use of a product formed by hydrogenation of an aromatic compound as auxiliary liquid for conveying an aromatic compound and also the use of an alcohol or an ester derived from alcohol and carboxylic acid as auxiliary liquid for conveying carboxylic acids or carboxylic acid derivatives.
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Page/Page column 8
(2012/05/20)
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- METHOD FOR INTERMITTENT PREPARATION OF LOW CONTENT TRANS-TRANS ISOMER-CONTAINING 4,4'-DIAMINODICYCLOHEXYLMETHANE
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The present invention discloses a method for intermittently producing 4,4'-diaminodicyclohexyl methane (H12MDA) with a low amount of the trans-trans isomer thereof, which comprises: controlling the reaction process by stopping the reaction when, except for a solvent, the reaction solution comprises MDA of 0-5 wt% and H6MAD of 1-20 wt%; and b) separating the reaction solution obtained from step a) by conventional means to obtain H12MDA product with desired purity, and allowing the un-reacted material and intermediate product to be recycled to the reactor after being accumulated. The method of the present invention decreases the amount of the trans-trans isomer in H12MDA, increases the yield of the reaction, and reduces the production cost. The present invention also provides a post treatment process of the reaction mixture.
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Page/Page column 8
(2012/10/18)
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- CONTINUOUS METHOD AND REACTOR FOR HYDROGENATING ORGANIC COMPOUNDS
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The present invention relates to a continuous process for hydrogenating organic compounds in a polyphasic system in the presence of a homogeneous or heterogeneous catalyst, which comprises performing the process in two stages, the first stage being performed in a loop reactor with an external heat exchanger and the second stage in a bubble column reactor with limited backmixing. The present invention further relates to a hydrogenation reactor (1) in a tall cylindrical design comprising a concentric guide tube (2) arranged in the lower reaction region and a mixing nozzle (3) directed upward, through which reactants and reaction mixture can be supplied, a pump (4) and a heat exchanger (5), which are present in an external pump circulation system which leads from the reactor to the mixing pump, and with one or more gas- and liquid-permeable internals (10) mounted in the upper region of the reactor, where the ratio of total length to diameter of the hydrogenation reactor (1) is in the range from 5:1 to 100:1 and the ratio of the volume of the upper region of the reactor to the volume of the lower region of the reactor is from 0.05:1 to 10:1.
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Page/Page column 8-9
(2011/06/24)
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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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- Hydrogenation of aromatic amines to alicyclic amines using a lithium aluminate-based catalyst
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The present invention relates to processes for the catalytic hydrogenation of aromatic amines to their acyclic counterparts using a ruthenium catalyst on a lithium aluminate support. The hydrogenation process comprises contacting an aromatic amine with hydrogen in the presence of a ruthenium catalyst under temperature and pressure conditions suitable to effect ring hydrogenation. The process is especially useful for hydrogenating aniline to cyclohexylamine.
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Page/Page column 7-8
(2008/06/13)
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- Hydrogenation of aromatic amines to alicyclic amines using a ruthenium catalyst supported on lithium aluminate
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The present invention relates to processes for the catalytic hydrogenation of aromatic amines to their acyclic counterparts using a ruthenium catalyst on a lithium aluminate support. The hydrogenation process comprises contacting an aromatic amine with hydrogen in the presence of a ruthenium catalyst under temperature and pressure conditions suitable to effect ring hydrogenation. The process is especially useful for hydrogenating aniline to cyclohexylamine.
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Page/Page column 11
(2008/06/13)
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- Hydrogenation of methylenedianiline
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The invention is directed to an improvement in a catalytic process for the ring hydrogenation of a methylenedianiline feedstock, including crude methylenedianiline. One component of the improvement is a pretreatment process which resides in passing the crude methylenedianiline feedstock over a ruthenium catalyst carried on a fixed bed support, cooling without venting, and then hydrogenation of the pretreated crude methylenedianiline feedstock over a rhodium catalyst or a mixed Rh/Ru catalyst carried on a monolith support and carrying out the ring hydrogenation in a batch reaction. Another component in the improvement is the employment of a catalyst comprised of rhodium and ruthenium carried on a monolith support.
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Page/Page column 5-6
(2008/06/13)
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- Hydrogenation of highly contaminated methylenedianiline
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This invention relates to a process for the catalytic hydrogenation of impurity laden methylenedianiline feedstocks commonly referred to a MDA-50 and MDA-60. The process for hydrogenating methylenedianiline containing at least 40% oligomer function by weight comprises: contacting the feedstock with hydrogen in the presence of a rhodium/ruthenium containing catalyst system carried on a lithium aluminate support under conditions for effecting ring hydrogenation.
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Page/Page column 4
(2010/02/14)
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- METHOD OF HYDROGENATION REACTION
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Disclosed is a heterogeneous catalytic hydrogenation process comprising hydrogenating a substance to be hydrogenated under trickle flow condition using a reaction tower charged with a solid catalyst, in which hydrogen gas and a liquid phase containing the substance to be hydrogenated are made to flow co-currently downward from above, wherein dynamic liquid phase holdup amount per unit catalyst exterior surface area of the catalyst charged in the reaction tower is 0.005 × 10-3 to 0.14 × 10-3 m3/m2 and the catalyst has a catalyst strength of 1.0 Kg or more, as determined by the following formulacatalyst strength = A-2σ wherein A represents a mean value of minimum strengths of 100 catalyst samples measured according to the method described in "Test method for crushing strength" of JIS Z-8841-1993" and σ represents a mean standard deviation.
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Page/Page column 22-23
(2008/06/13)
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- METHOD FOR THE PRODUCTION OF AMINES FROM COMPOUNDS COMPRISING CARBODIIMIDE GROUPS, BY HYDROLYSIS WITH WATER
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The invention relates to a single or multiple-step method for the production of monoamines, diamines and/or polyamines from carbodiimide groups and, optionally, also other groups of compounds comprising isocyanate chemicals, by hydrolysis with water.
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Page/Page column 7
(2008/06/13)
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- PROCESS FOR INCREASING THE SELECTIVITY OF THE HYDROGENATION OF 4,4'-DIAMINODIPHENYLMETHANE TO 4,4'-DIAMINODICYCLOHEXYLMETHANE IN THE PRESENCE OF AN N-ALKYL-4,4'-DIAMINODIPHENYLMETHANE
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The invention relates to a process for increasing the selectivity of the hydrogenation of 4,4'-diaminodiphenylmethane (4,4'-MDA) to diaminodicyclohexylmethane (4,4'-HMDA) by catalytic hydrogenation of a mixture containing 4,4'-MDA as the main component and its mono-N-methyl derivative as a secondary component. According to the invention, the hydrogenation is terminated before a conversion of 4,4'-MDA to 4,4'-HMDA of 99% is achieved. Under these conditions, a substantially smaller proportion of the N-methyl-4,4'-MDA is hydrogenated to N-methyl-4,4-HMDA.
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- Process for the preparation of six-membered ring carbocycles
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Six-membered ring carbocycles of the formula (II) can be prepared by ring hydrogenation of aromatic compounds of the formula (I) the definitions for which are given in the description, in a reaction system consisting of two liquid, immiscible phases in which elemental hydrogen is dispersed. The first phase consists of the aromatic compound (I) and, if necessary, a water-immiscible solvent. The second phase is essentially aqueous and comprises, colloidally dispersed therein, a hydrogenation-active metal as hydrogenation catalyst, and auxiliaries for stabilizing the colloidal catalyst. The process is carried out at from 50 to 180° C. and from 1 bar to 400 bar.
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- Cosmetic composition containing an amide-amine type condensate, and a cosmetic treating process using said condensate
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A cosmetic composition for improving the suppleness of the skin or hair and for protecting the keratin of the skin or hair from degradation by atmospheric agents or light comprises in a cosmetic or dermatologic acceptable vehicle a saturated condensate resulting from the polyaddition of a bis-acrylamide and a sterically hindered primary diamine, the condensate being saturated by hydrogenation or by addition of a thiol or an amine on the double bonds of the acrylamide residue.
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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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