- Selective Synthesis of Bisdimethylamine Derivatives from Diols and an Aqueous Solution of Dimethylamine through Iridium-Catalyzed Borrowing Hydrogen Pathway
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Bisdimethylamine derivatives are an important class of compounds in the polymer and pharmaceutical industries. However, existing methods for the synthesis of these compounds have several drawbacks such as low selectivity, use of toxic reagents, and generation of waste. In this study, a new system was developed for the selective synthesis of bisdimethylamine derivatives using a diol and dimethylamine as starting materials and an iridium complex bearing an N-heterocyclic carbene ligand as catalyst. The starting materials were easily available, less toxic, inexpensive, and easy to handle. The reaction proceeded efficiently through a borrowing hydrogen pathway under aqueous conditions, without any additional organic solvent, to afford various bisdimethylamine derivatives in good to excellent yields.
- Fujita, Ken-ichi,Jeong, Jaeyoung
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- Cyclic preparation method of dimethylamino ethyl ether
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The invention provides a cyclic preparation method of dimethylamino ethyl ether, which comprises the following steps: taking N,N-dimethyl ethanol amine as a raw material, reacting under the catalyticaction of loaded amorphous carbon and composite acid to generate dimethylamino ethyl ether and a byproduct namely water. Compared with the conventional method, the method has the advantages of low reaction temperature, high selectivity, and cyclic utilization of the catalyst and composite acid, the environment is protected, and a great economic value is created.
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Paragraph 0030; 0035-0055
(2020/12/30)
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- Production method of BDMAEE
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The invention discloses a production method of BDMAEE. The production method comprises the following steps: adding sulfuric acid, DMEA and super-strong solid acid taken as a catalyst in a reaction vessel to perform an etherification reaction; adding an extractant to obtained etherification liquid, and introducing ammonia to an extraction system to neutralize while stirring, and stopping introducing ammonia to neutralize until pH is 11-13; filtering an obtained product to achieve solid-liquid separation; washing and drying a solid obtained by filtering to obtain ammonium sulfate; and carrying out distillation on filtrate obtained by filtering to obtain BDMAEE. BDMAEE prepared by the method disclosed by the invention is high in efficiency and product yield, high in purity and less in wastewater, and can realize resource utilization of by-products.
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Paragraph 0065-0068; 0077-0111
(2019/08/01)
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- Method for homogeneously catalyzing alcohol amination
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The invention relates to a method for homogeneously catalyzing alcohol amination. The method comprises the following steps: mixing diethylene glycol or 1,6-hexanediol, dimethylamine, a ruthenium metalcatalyst and a non-polar solvent and carrying out homogeneous catalysis reaction; separating. According to the method provided by the invention, under the catalysis of a noble metal (rhodium, ruthenium and iridium) metallic catalyst, the diethylene glycol which has a cheap price and is easy to obtain or the 1,6-hexanediol is directly subjected to the amination by utilizing the dimethylamine through a one-step method; bis(2-dialkylaminoethyl)ether or N,N,N,N-tetramethylhexanediamine is prepared in a high-conversion-rate and high-selectivity manner.
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Paragraph 0068-0074
(2019/02/21)
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- Synthesis of bis(2-dimethylaminoethyl) ether
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A bis(2-dimethylaminoethyl) ether product is prepared by chlorinating 2-(2-(dimethylamino)ethoxy)ethanol, which is taken as a raw material, by using thionyl chloride to obtain a corresponding chloride; preparing the chloride and trimethylamine into quaternary ammonium salt; drying the obtained quaternary ammonium salt, then using ethylene diamine to enable one methyl of the quaternary ammonium salt to be transferred onto the ethylene diamine at high temperature, and rectifying.
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Paragraph 0013
(2017/11/04)
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- Bis(2-dimethylaminoethyl)ether synthesis method
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The invention belongs to the technical field of organic macromolecular compounds and relates to a bis(2-dimethylaminoethyl)ether synthesis method. The method includes subjecting dimethylamine and ethylene oxide to reaction in a high-pressure reactor, wherein a mole ratio is 1:2-2.2, a reaction temperature is 60-100 DEG C, reaction time is 2-5 hours, and curing time is 0.5-1 hour; adding a catalyst Cu-Ni/gamma-Al2O3, adopting hydrogen for adjusting an internal pressure of the reactor to 1.5-2.5 MPa, controlling the temperature at 190-220 DEG C, controlling a reaction pressure to be 10-25 MPa, and reacting for 6-13h; after the pressure drops to 1.0 MPa, feeding to the middle of an amine/hydrogen removal tower to discharge the dimethylamine and the hydrogen in the mixture from the top of the amine/hydrogen removal tower, and subjecting a crude product of bis(2-dimethylaminoethyl)ether at the bottom of the amine/hydrogen removal tower to reduced pressure distillation and separation. The bis(2-dimethylaminoethyl)ether synthesis method is applied to polyether preparation and has advantages of high equipment utilization rate, high preparation efficiency and the like.
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Paragraph 0042-0047; 0056; 0059; 0062
(2017/06/10)
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- Method for synthesizing bis(dimethylaminoethyl)ether under catalysis of metal catalyst
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The invention discloses a method for synthesizing bis(dimethylaminoethyl)ether (BDMAEE) under the catalysis of a metal catalyst. The method comprises the following steps: preparing a metal oxide; then preparing the metal catalyst from the metal oxide; and with dimethylamine and dimethylaminoethoxyethanol as raw materials, preparing BDMAEE under the catalysis of the metal catalyst, wherein a main inorganic by-product is water, and produced organic by-products can be recycled through distillation and purification. The method provided by the invention has good economic benefits and overcomes the problem of environmental pollution of conventional BDMAEE production processes.
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Paragraph 0037; 0038; 0039; 0040
(2018/02/04)
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- Preparation method for series of polyurethane catalysts
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The invention discloses a preparation method for a series of polyurethane catalysts. The preparation method comprises the following steps: SioO2 and Al2O3 with different ratios are employed as carriers, soaked in an ammonium sulfate aqueous solution, dried and roasted, and a silicon-aluminum-loaded solid acid catalyst is prepared; then a mixture of N,N-dimethyl ethanolamine and N-methyl diethanolamine is employed as a raw material, the raw materials and the silicon-aluminum-loaded solid acid catalyst accounting for 1-10% of the total weight of the raw material are added in an autoclave and a reaction is carried out; the filtrate after the reaction is subjected to rectification separation and therefore N-methyl morpholine, 2-dimethylaminoethyl ether and N,N,N'-trimethyl-N'-hydroxyethyl-bis-amino ethyl ether are obtained respectively.
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Paragraph 0059; 0060; 0065
(2016/10/10)
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- Method for Preparation of Bis (2-dialkyaminoethyl) Ether
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A bis (2-dialkylaminoethyl) ether synthesizing method is disclosed, which includes steps of: 1) synthesizing: wherein N,N-dialkylethanolamine, N,N-dialkylamine and ethyne are mixed at a mole ratio of 4:3:1-2:1:1 as a raw material; and the raw material, catalyst and solvent are added in a high-pressure clave for reaction in a sealed condition; a weight of catalyst accounts for 2.0%-10.5% of the total weight of the raw material; a reaction temperature is 50-120° C. and the reaction time is 3-7 hours; the clave is then opened after reaction and a filtrate is collected by filtering the reaction mixture; and 2) separating: wherein the filtrate obtained in the step 1) is rectified to obtain the bis (2-dialkylaminoethyl) ether as a product. The synthetic method of the bis (2-dialkylaminoethyl) ether in the present invention has many characteristics, such as simple process, high atomic economy, etc.
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Paragraph 0037; 0038; 0039; 0040; 0041; 0042; 0043
(2015/11/17)
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- Method for separating N,N,N'-trimethylbisaminoethylether and/or N,N-dimethylbisaminoethylether from a mixture
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The present invention relates to a method for separating N,N,N'-trimethylbisaminoethylether and/or N,N-dimethylbisaminoethylether, from a mixture A comprising N,N,N'-trimethylbisaminoethylether, and N,N-dimethylbisaminoethylether, wherein said method comprises the steps of: (a) contacting said mixture A with an acylating agent, to form a mixture B comprising the amides of N,N,N'-trimethylbisaminoethylether and of N,N-dimethylbisaminoethylether, respectively; and (b1) separating the amide of N,N,N'-trimethylbisaminoethylether from mixture B; and (c1) recovering N,N,N'-trimethylbisaminoethylether from its amide by means of a transamidation reaction; and/or (b2) separating the amide of N,N-dimethylbisaminoethylether from mixture B; and (c2) recovering N,N-dimethylbisaminoethylether from its amide by means of a transamidation reaction.
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Paragraph 0138
(2015/05/05)
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- METHOD FOR THE CONTINUOUS PRODUCTION OF AN AMINE USING AN ALUMINUM-COPPER CATALYST
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Process for the continuous preparation of an amine by reaction of a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary and secondary amines at a temperature in the range from 60 to 300° C. in the presence of a catalyst comprising copper oxide and aluminum oxide, wherein the reaction takes place in the gas phase and the catalytically active composition of the catalyst before reduction with hydrogen comprises PS from 20 to 75% by weight of aluminum oxide (Al2O3), from 20 to 75% by weight of oxygen-comprising compounds of copper, calculated as CuO, from 0 to 2% by weight of oxygen-comprising compounds of sodium, calculated as Na2O, and less than 5% by weight of oxygen-comprising compounds of nickel, calculated as NiO, and the shaped catalyst body has a pellet shape having a diameter in the range from 1 to 4 mm and a height in the range from 1 to 4 mm.
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Page/Page column 9
(2011/08/03)
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- A METHOD FOR PROVIDING A SECONDARY OR TERTIARY AMINE
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A method for providing a secondary or tertiary amine with formula (R1R2NR3)2NR4 is provided, wherein each of R1 and R2 are chosen from the group consisting of a methyl group, an ethyl group, an iso-propyl group and an n-propyl group; R3 being an alkoxyalkyl group chosen from the group consisting of -CH2CH2OCH2CH2-, -CH2CH2OCH2CH2CH2- and -CH2CH2CH2OCH2CH2CH2-; R4 is chosen from the group consisting of a hydrogen, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group and a group with formula R1R2NR3. The method comprises the steps: (α)reacting R1R2NR3(OH) with ammonia, thereby providing a mixture comprising (R1R2NR3)2NR4; (β) separating (R1R2NR3)2NR4 from said mixture.
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Page/Page column 17-23
(2010/12/29)
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- METHOD FOR THE CONTINUOUS PRODUCTION OF AN AMINE
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The invention relates to a method for the continuous production of an amine by reacting a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound, selected from the group containing ammonia and primary and secondary amines, at a temperature that ranges between 60 and 300 °C in the presence of a catalyst containing copper. According to the invention, the catalytically active mass of the catalyst contains the following prior to its reduction with hydrogen: 20 to 85 wt. % aluminium oxide (Al2O3), zirconium dioxide (ZrO2), titanium dioxide (TiO2) and/or silicon dioxide (SiO2); 1 to 70 wt. % copper compounds containing oxygen, calculated as CuO; 0 to 50 wt. % magnesium compounds containing oxygen, calculated as MgO; chromium compounds containing oxygen, calculated as Cr2O3; zinc compounds containing oxygen, calculated as ZnO; barium compounds containing oxygen, calculated as BaO; and/or calcium compounds containing oxygen, calculated as CaO; and less than 30 wt. % nickel compounds containing oxygen, calculated as NiO, in relation to the copper compounds containing oxygen, calculated as CuO. The reaction in the gas phase takes place isothermally in a tubular reactor.
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Page/Page column 25
(2008/06/13)
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- Obtention of n-methylated amines from selective vapor phase amination of amino ether alcohols
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A method for converting amino ether alcohols to amino ether amines by amination in the vapor phase with a catalyst comprising copper and zinc. The catalyst may also comprise an alkali metal, an alkaline earth metal, or a lanthanide element as a promoter.
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- Synthesis of bis[2-(N,N-dimethylamino)ethyl] ether
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A process is disclosed which comprises reacting trimethylamine with 2-[2-(N,N-dimethylamino)ethoxy]ethanol in the presence of nickel catalyst to produce bis[2-(N,N-dimethylamino)ethyl] ether.
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