- Precursors of biological cofactors from ultraviolet irradiation of circumstellar/interstellar ice analogues
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Biological cofactors include functionalized derivatives of cyclic tetrapyrrole structures that incorporate different metal ions. They build up structural partnerships with proteins, which play a crucial role in biochemical reactions. Porphyrin, chlorin, bacteriochlorin, and corrin are the basic structures of cofactors (heme. chlorophyll, bacteriochlorophyll, siroheme, F 430, and vitamin B12). Laboratory and theoretical work suggest that the molecular building blocks of proteins (α-amino acids) and nucleic acids (carbohydrates, purines, and pyrimidines) were generated under prebiotic conditions. On the other hand, experimental data on the prebiotic chemistry of cofactors are rare. We propose to search directly for the pathways of the formation of cofactors in the laboratory. Herein we report on the detection of N-heterocycles and amines in the room-temperature residue obtained after photo- and thermal processing of an interstellar ice analogue under high vacuum at 12 K. Among them, hexahydro-1,3,5-triazine and its derivatives, together with monopyrrolic molecules, are precursors of porphinoid cofactors. Hexahydropyrimidine was also detected. This is the first detection of these compounds in experiments simulating circumstellar/interstellar conditions. Except for 2-aminopyrrole and 2,4-diaminofuran, which were only found in 13C-labeled experiments, all the reported species were detected in both 12C- and 13C-labeled experiments, excluding contamination. The molecules reported here might be present in circumstellar/interstellar grains and cometary dust and could be detected by the Stardust and Rosetta missions.
- Meierhenrich, Uwe J.,Munoz Caro, Guillermo M.,Schutte, Willem A.,Thiemann, Wolfram H.-P.,Barbier, Bernard,Brack, Andre
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Read Online
- PRODUCTION OF NITROGEN-CONTAINING CHELATORS
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Reaction pathways and conditions for the production of nitrogen-containing chelators, such as a glycine derivative, as described herein. In particular, the present disclosure describes a process for the production of a nitrile intermediate by reacting a tetra-amino compound with an aldehyde and a hydrogen cyanide to form the nitrile intermediate. The nitrile intermediate may then be further processed to produce the chelators at a high yield and/or a high purity.
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Paragraph 0079-0080
(2022/01/08)
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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 0136; 0137; 0142
(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 0137; 0138; 0139; 0142; 0143
(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 0136; 0137; 0142
(2018/05/24)
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- Preparing method for glyphosate
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The invention relates to a preparing method for glyphosate and belongs to the technical field of chemical engineering. The preparing method specifically comprises the four steps of synthesis of iminodiacetic acid, preparation of pmida, preparation of glyphosate and solid and liquid separation. According to the preparing method, firstly, precious metal silver is loaded on titanium dioxide, the surface nature of titanium dioxide is influenced, electron distribution is changed, and catalytic activity is improved; then, titanium dioxide loaded with silver is loaded into activated carbon and irradiated with an ultraviolet source. The selectivity of glyphosate is greatly improved, the oxidization process of pmida is greatly shortened, the yield of glyphosate is increased to 96.3%, and the product purity can reach 97.6%; besides, the content of methyl aldehyde is low, fewer products are generated, and the requirement of the nation for environment friendliness is met.
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Paragraph 0028-0030
(2017/04/05)
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- METHOD FOR ISOLATING METHYLGLYCINENITRILE-N,N-DIACETONITRILE
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A method for isolating methylglycinenitrile-N,N-diacetonitrile (MGDN) from an aqueous mixture comprising MGDN is provided The method comprises cooling the aqueous mixture in one or more steps In one of these steps the mixture is cooled at a cooling rate of at least 20 K/h from a temperature above the solidification point of MGDN to a temperature below the solidification point of MGDN The method is implemented continuously
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Page/Page column 4
(2012/07/28)
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- METHOD FOR ISOLATING METHYLGLYCINENITRILE-N,N-DIACETONITRILE
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A method for isolating methylglycinenitrile-N,N-diacetonitrile (MGDN) from an aqueous mixture comprising MGDN is provided The method comprises cooling the aqueous mixture in one or more steps In one of these steps the mixture is cooled at a cooling rate of at least 20K/h from a temperature above the solidification point of MGDN to a temperature below the solidification point of MGDN The method is implemented continuously
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Page/Page column 8-9
(2011/04/26)
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- METHOD FOR PRODUCING AMINONITRILES
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The invention relates to a process for preparing an amino nitrile mixture comprising aminoacetonitrile (AAN) and from 5 to 70% by weight of iminodiacetonitrile (IDAN), which comprises heating crude AAN which is largely free of formaldehyde cyanohydrin (FACH-free) at a temperature of from 50 to 150° C.
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Page/Page column 3
(2010/02/17)
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- METHOD FOR ISOLATING METHYL GLYCINE NITRILE-N,N-DIACETONITRILES FROM AN AQUEOUS CRUDE MIXTURE
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The invention relates to a method for isolating methyl glycine nitrile-N,N-diacetonitriles (MGDN) from an MGDN-containing aqueous emulsion with an MGDN content of 3 - 50% by weight in a crystallizer. The inventive method is characterized by (a) cooling the aqueous emulsion, starting from a temperature above the solidification point, to a temperature below the solidification point, the cooling rate in the temporal mean not exceeding 5 K/h, until substantially the total amount of the emulsified MGDN has solidified; and (b) continuing to cool the aqueous suspension obtained and/or concentrating it, the cooling rate being higher than that in step (a).
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Page/Page column 8
(2008/06/13)
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- Continuous process for the cyanoalkylation of compounds having one or more NH functions
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The invention relates to a continuous process, carried out in two steps, for the cyanoalkylation of compounds having one or more NH functions by reaction thereof with carbonyl compounds and hydrocyanic acid, in which the first step is carried out without pressure at a temperature which is below the boiling point of the reaction mixture.
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- EQUILIBRIUM OF α-AMINOACETONITRILE FORMATION FROM FORMALDEHYDE, HYDROGEN CYANIDE AND AMMONIA IN AQUEOUS SOLUTION: INDUSTRIAL AND PREBIOTIC SIGNIFICANCE
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The equilibrium constant, Kan(H2CO), for the formation of α-aminoacetonitrile from formaldehyde, ammonia and hydrogen cyanide was evaluated at 25 deg C.A first estimation of Kan(H2CO) was obtained from extrathermodynamic relationships of the type log K' vs Σ?*.The final value was then obtained from a comparison of the experimental and calculated pH dependences of α-hydroxy- and α-aminoacetonitrile concentrations.From these results, it appears that, after equilibrium, the ratio between the concentrations of the two precursors glycine and hydroxyethanoic acid, is a linear function of the concentration of free ammonia, i.e. /=21 at 25 deg C.
- Moutou, G.,Taillades, J.,Benefice-Malouet, S.,Commeyras, A.,Messina, G.,Mansani, R.
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p. 721 - 730
(2007/10/02)
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- Chemistry of α-Amino Nitriles. Exploratory Experiments on Thermal Reactions of α-Amino Nitriles
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The paper extends a previously published report on chemical properties of α-amino nitriles and of members of the C3H4N2 ensemble (Scheme 1) as observed in experiments carried out under non-aqueous conditions.The reactions investigated and the observations made are summarized in some detail in the English footnotes (*) referring to Schemes 1-17 and Fig. 1.
- Xiang, Yi-Bin,Drenkard, Susanne,Baumann, Karl,Hickey, Deirdre,Eschenmoser, Albert
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p. 2209 - 2250
(2007/10/02)
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- Chemie der α-Aminonitrile. 1. Mitteilung. Einleitung und Wege zu Uroporphyrinogen-octanitrilen
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Chemistry of α-Aminonitriles I: Introduction and Pathways to Uroporphyrinogen-octanitriles.An introduction to experimental studies on the chemistry of α-aminonitriles potentially relevant to the problems of prebiotic chemistry is presented.The framework of conditions wherein the investigations is chosen to be carried out implies both molecular oxygen and - whenever feasible - water to be excluded from reaction conditions.This study focusses on 2-amino-2-propenenitrile (3) (Scheme 6) as central starting material of reaction sequences which aim at the nitrile forms of proteinogenic amino acids as well as at the aza forms of building blocks of biological cofactor molecules as their targets (Scheme 5).Schemes 13, 16, 23 as well as 25, and 26 summarize reaction sequences by which 3 is tranformed within the definied framework of conditions into the thermodynamic (statistically controlled) mixture of the four isomeric uroporphyrinogen-octanitriles 57-60.HPLC's of such mixtures document the dominance of the least symmetrical isomer whose constitutional pattern of peripheral substituents happens to be the one present in all biological porphinoids.Preparative procedures for the synthesis of 3 (Scheme 9), the β,β-disubstututed pyrrol-nitriles 30, 53, and 54 (Scheme 19) as well as the porphyrinogen-octakis(propionitrile) and -octakis(acetonitrile) 65 and 66, respectively (Scheme 24) are given.
- Ksander, Gary,Bold, Guido,Lattmann, Rene,Lehmann, Christian,Frueh, Thomas,et al.
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p. 1115 - 1172
(2007/10/02)
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- Process for the preparation of iminodiacetonitrile
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A process for preparing iminodiacetonitrile which comprises bringing together under reaction conditions formaldehyde, hydrogen cyanide and a source of ammonia under substantially stoichiometric conditions at a temperature between about 30° and about 65° C. at a pH between about 1.5 and about 5.5, preferably between about 3.5 and about 5.3, to produce the desired iminodiacetonitrile.
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- The Ion-exchange Chromatography of Imino Derivatives of Glycine
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The resolution of the six imino derivatives of glycine (Gly) by ion-exchange chromatography is described.The imino compounds included iminodiacetonitrile (1), iminodiacetamide (2), iminodiacetic acid (3), α-(cyanomethylamino)acetamide (4), α-(cyanomethylamino)acetic acid (5), and α-(carbamoylmethylamino)acetic acid (6).A mixture of 1-6 was chromatographed along with Gly, glycinamide, aminoacetonitrile, and NH3 with an automatic amino acid analyzer using Aminex A-4 resin column (0.25φ x 50 cm) and sodium citrate buffers.When the initial buffer of pH 3.25 was changed to pH 6.50 15 min after beginning the analysis, these ten components were completely resolved.The analysis was completed in about 4.5 h.The stability of 1, 4, and 5 in aqueous media at room temperature was also studied.
- Kawashiro, Katsuhiro,Morimoto, Shiro,Yoshida, Hideyuki
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p. 792 - 795
(2007/10/02)
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- Process for the production of iminodiacetonitrile
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The invention is directed to a process for the production of iminodiacetonitrile by reaction of hexamethylenetetramine with hydrogen cyanide in acidic aqueous mediums. In this process the pH during the reaction which is 5.5 to 7.5 at the beginning is progressively lowered, altogether around 0.5 to 3.5 units and free formaldehyde is present only to a slight extent. Through this and in contrast to the known processes the formation of byproducts is suppressed and iminodiacetonitrile is produced directly in very good yields and sufficiently pure for further use.
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- N-Phosphonomethyliminodiacetonitrile and certain derivatives thereof
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N-phosphonomethyliminodiacetonitrile and certain derivatives thereof are novel compounds which can be used as herbicides themselves and/or can be converted to known herbicides.
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