- PROCESS FOR MANUFACTURING A CYCLIC UREA ADDUCT OF AN ETHYLENEAMINE COMPOUND
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The invention pertains to a process for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound having a linear -NH-CH2-CH2-NH- group, the process comprising the steps of - in an absorption step contacting a liquid medium comprising an ethyleneamine compound having a linear -NH-CH2-CH2-NH- group with a CO2-containing gas stream at a pressure of 1 -20 bara, resulting in the formation of a liquid medium into which CO2 has been absorbed, - bringing the liquid medium to cyclic urea formation conditions, and in an urea formation step forming cyclic urea adduct of the ethyleneamine compound, urea formation conditions including a temperature of at least 120°C, wherein the total pressure at the end of the urea formation step is at most 20 bara, wherein the temperature in the absorption step is lower than the temperature in the urea formation step. It has been found that the process according to the invention makes it possible to obtain cyclic urea adducts in an efficient manner in the absence of metal-containing catalysts and to perform the process under relatively mild conditions, in particular relatively low pressure. More specifically, by separating the CO2 absorption step from the urea formation step, the CO2 absorption step can be carried out at relatively low temperatures and pressures. And because the CO2 is already present in the system at the beginning of the urea formation step, the pressure in the urea formation step does not need to be high.
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Page/Page column 23-25
(2019/02/25)
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- Ionic-Liquid-Supported 1,3-Dimethylimidazolidin-2-one: Application as a Reusable Halogenation Reagent
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We describe the synthesis of ionic-liquid-supported 1,3-dimethylimidazolidin-2-one, together with the halogenation of alcohols in a reaction system in which this reagent is combined with oxalyl chloride. A new method was established that does not require additives such as bases, and which permits the ready isolation and purification of the product. Good conversions were obtained, and good reusability of the reagent was observed.
- Koguchi, Shinichi,Shibuya, Yuga,Igarashi, Yusuke,Takemura, Haruka
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supporting information
p. 943 - 946
(2019/05/10)
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- PROCESS FOR PREPARING CYCLIC ALKYLENE UREAS
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A process for producing a cyclic alkylene urea product of Formula I: in which a compound of Formula II and/or Formula III is contacted in a reaction zone with a compound of Formula IV and/or Formula V and in the presence of one or more carbonyl delivering compounds; in which; R1 is –[A?X?]qR3; R2 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from ?OH and ?NH2; R3 is on each occurrence independently selected from H and C1 to C6 alkyl groups which are optionally substituted by one or two groups selected from ?OH and ?NH2; A is on each occurrence independently selected from C1 to C3 alkylene units, optionally substituted by one or more C1 to C3 alkyl groups; X is on each occurrence independently selected from ?O?, ?NR2?, groups of Formula VI, and groups of Formula VII and p and q are each independently selected from a whole number in the range of from 0 to 8; wherein the compound of Formula II and/or the compound of Formula III are added to a reaction zone comprising compound of Formula IV and/or compound of Formula (V) continuously or semi-continuously over a period of time, or in two or more batches.
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Page/Page column 17-19
(2019/02/25)
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- PROCESS FOR MANUFACTURING A CYCLIC UREA ADDUCT OF AN ETHYLENEAMINE COMPOUND
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The invention pertains to a process for manufacturing a cyclic urea adduct of an ethyleneamine compound, the ethyleneamine compound being selected from the group of ethyleneamines and hydroxyethylethyleneamines and comprising at least one –NH-CH2-CH2-NH-moiety and at least two ethylene moieties, wherein the ethyleneamine compound is reacted with CO2 in the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof, the molar ratio of auxiliary compound to amine compound being at least 0.02:1. It has been found that the presence of an auxiliary compound selected from ethylenediamine (EDA), monoethanolamine (MEA) and mixtures thereof leads to a substantial increase of the reaction rate as compared to a process wherein the auxiliary compound is not present.
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Page/Page column 14-15
(2018/12/14)
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- In order to CO2 As raw materials for preparing 1 - (2 - hydroxyethyl) - 2 - imidazolidinone method
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The invention relates to the field of preparation of cyclic urea compounds, particularly to a method for preparing 1-(2-ethoxyl)-2-imidazolone by using CO2 as a raw material. 1-(2-ethoxyl)-2-imidazolone is obtained through a reaction of CO2 and ethanolamine. Compared with a conventional technology for preparing 1-(2-ethoxyl)-2-imidazolone, the method disclosed by the invention has the following advantages: (1) a synthetic method is scientific to design, an execution route is concise and reliable, and the method is suitable for industrial production; (2) required raw materials are low in toxicity, are cheap and are easy to obtain, so that the method conforms to the trend of green chemical development; (3) a catalyst is used in the reaction process, the catalytic activity is high, and the product yield is higher; (4) from the view of resources, the CO2 is a safe non-toxic rich carbon resource, and a reaction product, namely water, does not cause pressure to the environment.
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Paragraph 0031-0037; 0038-0044; 0045-0051; 0053-0058
(2017/09/26)
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- Continuous N-alkylation reactions of amino alcohols using γ-Al2O3 and supercritical CO2: Unexpected formation of cyclic ureas and urethanes by reaction with CO2
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The use of γ-Al2O3 as a heterogeneous catalyst in scCO2 has been successfully applied to the amination of alcohols for the synthesis of N-alkylated heterocycles. The optimal reaction conditions (temperature and substrate flow rate) were determined using an automated self-optimising reactor, resulting in moderate to high yields of the target products. Carrying out the reaction in scCO2 was shown to be beneficial, as higher yields were obtained in the presence of CO2 than in its absence. A surprising discovery is that, in addition to cyclic amines, cyclic ureas and urethanes could be synthesised by incorporation of CO2 from the supercritical solvent into the product.
- Streng, Emilia S.,Lee, Darren S.,George, Michael W.,Poliakoff, Martyn
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p. 329 - 337
(2017/03/15)
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- N-VINYLIMIDAZOLIDONE COMPOUND, AND POLYMER THEREOF
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PROBLEM TO BE SOLVED: To provide an N-vinylimidazolidone compound polymer that is expected to be applied for a cell culture material, a temperature-responsive material and others. SOLUTION: The present invention provides a polymer polymerized with an N-vinylimidazolidone compound (1) as a monomer, or a copolymer comprising the monomer and a monomer of a different structure (R1 is H, C1-12 alkyl or acyl; R2 and R3 is H or methyl). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0104; 0105
(2017/01/02)
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- Process for the Synthesis of N-substituted Cyclic Alkylene Ureas
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The invention relates to a process for the synthesis of N-substituted cyclic alkylene ureas by reacting a multifunctional aliphatic amine A having at least two amino groups which may be primary or secondary, at least one of which is a primary amino group, -NH2, and at least one of which is a secondary amino group, >NH, the other hydrogen group whereof having been substituted by a hydrocarbyl group which in turn may be substituted by a hydroxyl group, or an amino group, or a carboxyl group, or a ketone carbonyl group, or a hydrazide or hydrazone group, or a mercaptan group, and at least one further functional group selected from the group consisting of primary or secondary amino groups and hydroxyl groups, and an aliphatic organic carbonate component C selected from the group consisting of dialkyl carbonates CD and of alkylene carbonates CA.
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Paragraph 0045; 0046
(2013/03/26)
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- PROCESS FOR THE SYNTHESIS OF N-SUBSTITUTED CYCLIC ALKYLENE UREAS
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The invention relates to a process for the synthesis of N-substituted cyclic alkylene ureas by reacting a multifunctional aliphatic amine A having at least two amino groups which may be primary or secondary, at least one of which is a primary amino group, -NH2, and at least one of which is a secondary amino group, >NH, the other hydrogen group whereof having been substituted by a hydrocarbyl group which in turn may be substituted by a hydroxyl group, or an amino group, or a carboxyl group, or a ketone carbonyl group, or a hydrazide or hydrazone group, or a mercaptan group, and at least one further functional group selected from the group consisting of primary or secondary amino groups and hydroxyl groups, and an aliphatic organic carbonate component C selected from the group consisting of dialkyl carbonates CD and of alkylene carbonates CA.
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Page/Page column 20
(2013/03/26)
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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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- Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent
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Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable to the presence of catalyst and solvent. The preliminary investigation of the reaction mechanism showed that alkyl ammonium alkyl carbamate was quickly formed as the intermediate, and then the final product was formed by the intramolecular dehydration.
- Wu, Chaoyong,Cheng, Haiyang,Liu, Ruixia,Wang, Qiang,Hao, Yufen,Yu, Yancun,Zhao, Fengyu
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experimental part
p. 1811 - 1816
(2011/02/22)
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- Process for preparing derivatives of isopropenyl-α, α-dimethylbenzyl isocyanate
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A process for preparing blocked derivatives of m- or p- isopropenyl-α,α-dimethylbenzyl isocyanates, comprising reacting a meta- or a para-isopropenyl-α,α-dimethylbenzyl carbamate ester with hydroxy functional blocking group, such as hydroxyethylene-ethyleneurea, hydroxyethylenepropylene urea, dialkylaminoethanol and dialkylamino propanol
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Page/Page column 10
(2008/06/13)
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- NOVEL POLYMERIZABLE ACYL IMIDAZOLIDINONE MONOMERS
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Acyl imidazolidinones and compositions containing the same are disclosed, which are particularly suitable for use as self-crosslinkers and can also be used as wet adhesion properties, especially in latex-based polymer systems. Processes for preparing such compounds, compositions containing the same, as well as additional uses thereof are also disclosed.
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Page/Page column 11
(2010/11/29)
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- Self-crosslinking hydroxy/alkoxy acyl imidazolidinone monomers
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Acyl imidazolidinones and compositions containing the same are disclosed, which are particularly suitable for use as self-crosslinkers and can also be used as wet adhesion properties, especially in latex-based polymer systems. Processes for preparing such compounds, compositions containing the same, as well as additional uses thereof are also disclosed.
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- Wet adhesion promoter
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Compositions containing urea functional compounds are disclosed which are particularly suitable for use as post-added wet adhesion promoters in coatings, especially in aqueous emulsion systems used to make latex paints. A process of preparing the same is also disclosed, as well as a novel class of compounds.
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- Aminated alkoxylated imidazolidones
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Disclosed is a novel polyetherdiamine comprising an aminated, alkoxylated 1,2'-hydroxyethyl-2-imidazolidone represented by the formula: STR1 where R is H or an alkyl group of from 1 to 16 carbon atoms, R1, R2, R3 and R4 are selected from the group consisting of hydrogen and lower alkyl radicals having about 1 to 4 carbon atoms, and a+b=n, wherein n is a number of from about 2 to 80, prepared by reacting urea or certain carbonates with an aminoalkoxylamine, alkoxylating the product with alkylene oxide to form a polyol which is reductively aminated to form a novel polyetherdiamine containing an imidazolidone (cyclic urea).
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- Phenylamidine and phenylguanidine derivatives and their use as antidiabetic agents
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Compounds of formula I STR1 and their salts in which n=0 or 1, R1 and R2 are each aliphatic or cycloalkyl or NR1 R2 is an optionally substituted heterocyclic ring, R3 is alkyl, cycloalkyl or optionally substituted amino, R5 is an aliphatic group, R6 is H, an optionally substituted aliphatic group or a cycloalkyl group, or R3 and R5 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R5 and R6 together with the nitrogen to which they are attached form a heterocyclic ring optionally substituted by alkyl and R7 is optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, trifluoromethyl or cyano have utility as hypoglycemic agents.
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- Carbonylation of Amines by Carbon Dioxide in the Presence of an Organoantimony Catalyst
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1,3-Dialkylureas (RNHCONHR; where R = Bu, i-Bu, s-Bu, t-Bu, allyl, Ph) and tetramethylurea were successfully prepared at 80 deg C under an initial CO2 pressure of 4.9 MPa, from the corresponding amines and carbon dioxide with catalysis by triphenylstibine oxide and assistance from tetraphosphorus decasulfide (Ph3SbO/P4S10).Monitoring of the reaction by 13C NMR revealed that the successive thiolation of carbamic acid to an intermediate antimony carbamate species and aminolysis of the carbamothioic acid thus formed constitute the reaction course.Cyclic ureas can also be synthesized by similar carbonylations of diamines (RNHCH2CH2NHR'; where R, R' = H, H; Me, H; Ph, H; HOCH2CH2, H; HOCHMeCH2, H; Me, Me).Furthermore, the Ph3SbO/P4S10 catalyst system enabled the preparation of trisubstituted ureas such as 1-butyl-3,3-diethylurea by a selective cocarbonylation of butylamine and diethylamine.
- Nomura, Ryoki,Hasegawa, Yasuhiro,Ishimoto, Mikio,Toyosaki, Takayuki,Matsuda, Haruo
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p. 7339 - 7342
(2007/10/02)
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- 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds
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3-Pyrrolidinythio-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acid compounds which have antimicrobial activity have been prepared.
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- Nitroimidazoles: Part IV - 1-Sulphonyl(carbamoyl/thiocarbamoyl)-3-(1-methyl-5-nitroimidazol-2-yl)-2-imidazolidinones
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Sulphone (5) is condensed with sodium salts of a variety of 1-suplphonyl (7), 1-thiocarbamoyl (9) and 1-carbonyl (10)-2-imidazolidinones to give 3-(2-imidazolyl)imidazolidinones (12), (13) and (14) respectively, out of which 1-methylsulphonyl-3-(1-methyl-5-nitro-imidazol-2-yl)-2-imidazolidinone (12a) is undergoing clinical trials as an antiamoebic-antitrichomonal agent. 15 and 16 are analougous imidazolidinones, while 17 and 18 are benzimidazolone derivatives.The reaction of 5 with the sodium salt of 2-imidazolidinone gives rise to the mono and bis-condensation products 21 and 22 respectively.Several other minor byproducts, 23-27 have been identified. 23, 26 and 27 arise from 21. 24, a transformation product of 5 leads to the ether 25 by a displacement reaction.A second synthesis of 12a involves the nitration of imidazolylimidazolidinone (30) in the terminal step, with 30 becoming available from 1-methyl-2-aminoimidazole (28) and chloroethyl isocyanate, and subsequent reaction of resultant 29 with methanesulphonyl chloride.The higher ring homologue, 33 of 12a is synthesised in poor yield from 5 and 1-methylsulphonylhexahydropyrimidinone.Treatment of 12a and 13a with KI in DMF leads to the isomeric 4-nitro derivatives 38a, b and desmethyl derivates 37a, b.Treatment of 12a with triethyloxonium fluoroborate affords the quaternary isothiourea (35) which is hydrolysed to 36.Treatment of 12a and 13a with aqeous alkali leads to cleavage of imidazolidinone ring to form the ethylenediamines 31a and b.Position isomers 41 and 43 of 12a are respetcively obtained by the reaction of 1-methyl-4-nitro-5-chloro-(40)-, and 1-methyl-5-nitro-4-chloro-(42)-imidazoles with 1-methylsulphonyl-ethylene urea.Treatment of the last compound with various reactive halides, e.g. 2-chlorobenzothiazole, yields several analogues 44a-i of 12a while niridazole (45) and methylsulphonyl chloride affords nitrothiazole analogue 46.
- Nagarajan, K.,Arya, V. P.,George, T.,Sudarsanam, V.,Shah, R. K.,et al.
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p. 928 - 940
(2007/10/02)
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