cas 646-25-3, 1,10-Diaminodecane | Articles data

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One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
Coeck, Robin,De Vos, Dirk E.
supporting information
p. 5105 - 5114
(2020/08/25)

A cobalt phosphide catalyst for the hydrogenation of nitriles
The study of metal phosphide catalysts for organic synthesis is rare. We present, for the first time, a well-defined nano-cobalt phosphide (nano-Co2P) that can serve as a new class of catalysts for the hydrogenation of nitriles to primary amines. While earth-abundant metal catalysts for nitrile hydrogenation generally suffer from air-instability (pyrophoricity), low activity and the need for harsh reaction conditions, nano-Co2P shows both air-stability and remarkably high activity for the hydrogenation of valeronitrile with an excellent turnover number exceeding 58000, which is over 20- to 500-fold greater than that of those previously reported. Moreover, nano-Co2P efficiently promotes the hydrogenation of a wide range of nitriles, which include di- and tetra-nitriles, to the corresponding primary amines even under just 1 bar of H2 pressure, far milder than the conventional reaction conditions. Detailed spectroscopic studies reveal that the high performance of nano-Co2P is attributed to its air-stable metallic nature and the increase of the d-electron density of Co near the Fermi level by the phosphidation of Co, which thus leads to the accelerated activation of both nitrile and H2. Such a phosphidation provides a promising method for the design of an advanced catalyst with high activity and stability in highly efficient and environmentally benign hydrogenations. This journal is
Jitsukawa, Koichiro,Mitsudome, Takato,Mizugaki, Tomoo,Nakata, Ayako,Sheng, Min,Yamasaki, Jun
p. 6682 - 6689
(2020/08/24)

METHOD FOR PREPARING PRIMARY DIAMINES BY KOLBE ELECTROLYSIS COUPLING REACTION
The present invention relates to a method for preparing primary diamines from amino acid compounds. Specifically, this invention is related to the preparation of a primary diamine from an amino acid and/or its salt by Kolbe electrolysis coupling reaction.
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Page/Page column 12; 13; 14; 15

(2019/07/13)

Sustainable hydrogenation of aliphatic acyclic primary amides to primary amines with recyclable heterogeneous ruthenium-tungsten catalysts
The hydrogenation of amides is a straightforward method to produce (possibly bio-based) amines. However current amide hydrogenation catalysts have only been validated in a rather limited range of toxic solvents and the hydrogenation of aliphatic (acyclic) primary amides has rarely been investigated. Here, we report the use of a new and relatively cheap ruthenium-tungsten bimetallic catalyst in the green and benign solvent cyclopentyl methyl ether (CPME). Besides the effect of the Lewis acid promotor, NH3 partial pressure is identified as the key parameter leading to high primary amine yields. In our model reaction with hexanamide, yields of up to 83% hexylamine could be achieved. Beside the NH3 partial pressure, we investigated the effect of the catalyst support, PGM-Lewis acid ratio, H2 pressure, temperature, solvent tolerance and product stability. Finally, the catalyst was characterized and proven to be very stable and highly suitable for the hydrogenation of a broad range of amides.
Coeck, Robin,Berden, Sarah,De Vos, Dirk E.
supporting information
p. 5326 - 5335
(2019/10/11)

High-carbon alkane diamine, and preparation method and application thereof
The invention relates to the field of high-carbon alkane diamine preparation, and discloses high-carbon alkane diamine, and a preparation method and application thereof. The preparation method of thehigh-carbon alkane diamine disclosed by the invention is characterized in that the structure of the high-carbon alkane diamine is as shown in the formula NH2-(CH2)m-NH2; the method comprises the following steps: (1) under amideation reaction conditions, reacting high-carbon alkane diacid which is as shown in the formula COOH-(CH2)n-COOH with an ammonia-containing compound to obtain high-carbon chain diamide which is as shown in the formula CONH2-(CH2)n-CONH2; (2) under an alkaline condition, enabling the high-carbon chain diamide which is as shown in the formula CONH2-(CH2)n-CONH2 to perform rearrangement degradation in the existence of water, sodium hypochlorite and/or sodium hypobromite to obtain the high-carbon alkane diamine which is as shown in the formula NH2-(CH2)m-NH2, wherein n=11to 15, and m=9 to 13. The method provided by the invention is a safe, convenient, simple and feasible preparation method for the high-carbon alkane diamine.
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Paragraph 0077; 0080-0082

(2019/03/28)

Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines
Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the other hand after deamination to benzaldehyde also as oxidant. All ω-HFAs tested were efficiently transformed to their corresponding ω-AmFAs using purified enzymes as well as a whole-cell system, separately expressing both the enzymes, with conversions ranging from 80-95%. Additionally, a single-cell co-expressing all enzymes successfully produced the ω-AmFAs as well as the α,ω-diamines with >90% yield. This system was extended by employing a lactonase, enabling the transformation of ?-caprolactone to its corresponding ω-AmFA with >80% conversion.
Sung, Sihyong,Jeon, Hyunwoo,Sarak, Sharad,Ahsan, Md Murshidul,Patil, Mahesh D.,Kroutil, Wolfgang,Kim, Byung-Gee,Yun, Hyungdon
supporting information
p. 4591 - 4595
(2018/10/23)

A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin
Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 °C and 200 mbar pressure on a rotatory evaporator, is extremely efficient, clean, and tolerant of a variety of functional groups.
Suthagar, Kajitha,Fairbanks, Antony J.
p. 713 - 715
(2017/01/13)

METHOD FOR PRODUCING ALKANOL AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
PROBLEM TO BE SOLVED: To provide a method for producing alkanol amines by alcohol amination of diols using ammonia under elimination of water. SOLUTION: The invention relates to a method for producing alkanol amines which comprise a primary amino group (-NH2) and a hydroxyl group (-OH), by alcohol amination of diols comprising two hydroxyl groups (-OH) using ammonia under elimination of water. The reaction is homogeneously catalyzed in the presence of at least one complex catalyst which contains at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0088; 0103

(2016/10/27)

The preparation obtained by homogeneous catalysis mellow amination method of the primary amine
The invention relates to a method for producing primary amines comprising at least one functional group of formula (-CH2-NH2), by alcohol amination of educts which comprise at least one functional group of formula (-CH2-OH), using ammonia, and elimination of water. The homogeneously catalyzed alcohol amination is carried out in the presence of at least one complex catalyst which contains at least one element selected from the groups 8 and 9 of the periodic table and at least one phosphorus donor ligand of general formula (I).
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Paragraph 0207-0208; 0214

(2017/02/28)

Cavitands as Reaction Vessels and Blocking Groups for Selective Reactions in Water
The majority of reactions currently performed in the chemical industry take place in organic solvents, compounds that are generally derived from petrochemicals. To promote chemical processes in water, we examined the use of synthetic, deep water-soluble cavitands in the Staudinger reduction of long-chain aliphatic diazides (C8, C10, and C12). The diazide substrates are taken up by the cavitand in D2O in folded, dynamic conformations. The reduction of one azide group to an amine gives a complex in which the substrate is fixed in an unsymmetrical conformation, with the amine terminal exposed and the azide terminal deep and inaccessible within the cavitand. Accordingly, the reduction of the second azide group is inhibited, even with excess phosphine, and good yields of the monofunctionalized products are obtained. In contrast, the reduction of the free diazides in bulk solution yields diamine products.
Masseroni, Daniele,Mosca, Simone,Mower, Matthew P.,Blackmond, Donna G.,Rebek, Julius
p. 8290 - 8293
(2016/07/19)

· Uniform catalyst by using alcohol aminosilicone di-, tri-and a method of manufacturing a polyphenylenepolyamine
The invention relates to a method for producing primary amines, which contain at least one functional group of the formula (-CH2-NH2) and at least one further primary amino group, by the alcohol amination of reactants, which contain at least one functional group of the formula (-CH2-OH) and at least one further functional group (-X), wherein (-X) is selected from hydroxyl groups and primary amino groups, using ammonia with removal of water, wherein the reaction is carried out in a homogeneously catalyzed manner in the presence of at least one complex catalyst containing at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand.
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Paragraph 0099; 0113

(2016/10/09)

PROCESS FOR PRODUCING COMPOUNDS COMPRISING NITRILE FUNCTIONS
The production of compounds comprising nitrile functions and of cyclic imide compounds is described. Further described, is the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, optionally of natural and renewable origin, and from a mixture N of dinitriles comprising 2-methylglutaronitrile (MGN), 2-ethylsuccinonitrile (ESN) and adiponitrile (AdN).
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Paragraph 0060

(2013/08/15)

PROCESS FOR PREPARING DI-, TRI- AND POLYAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
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Page/Page column 12; 16

(2012/09/22)

PROCESS FOR PREPARING ALKANOLAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
Process for preparing alkanolamines which have a primary amino group (—NH2) and a hydroxyl group (—OH) by alcohol amination of diols having two hydroxyl groups (—OH) by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
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Page/Page column 13-14; 19

(2012/09/22)

PROCESS FOR THE PREPARATION OF PRIMARY AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
Process for the preparation of primary amines which have at least one functional group of the formula (—CH2—NH2) by alcohol amination of starting materials which have at least one functional group of the formula (—CH2—OH), with ammonia, with the elimination of water, where the alcohol amination is carried out under homogeneous catalysis in the presence of at least one complex catalyst which comprises at least one element selected from groups 8 and 9 of the Periodic Table of the Elements, and also at least one phosphorus donor ligand of the general formula (I).
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Page/Page column 10; 13

(2012/09/22)

Redox self-sufficient biocatalyst network for the amination of primary alcohols
Driving the machinery: A biocatalytic redox-neutral cascade for the preparation of terminal primary amines from primary alcohols at the expense of ammonia has been established in a one-pot one-step method (see picture). Applying this artificial biocatalyst network, long-chain 1,ω-alkanediols were converted into diamines, which are building blocks for polymers, in up to 99 % conversion. Copyright
Sattler, Johann H.,Fuchs, Michael,Tauber, Katharina,Mutti, Francesco G.,Faber, Kurt,Pfeffer, Jan,Haas, Thomas,Kroutil, Wolfgang
supporting information
p. 9156 - 9159
(2012/10/30)

METHOD FOR THE SYNTHESIS OF HIGH PURITY PRIMARY DIAMINES AND/OR TRIAMINES
The present invention relates to a process for the preparation of primary di- and/or triamines of high purity from nitriles which can themselves originate from dimer and/or trimer acids. This process comprises a stage of ammoniation of the acid functional groups and a stage of hydrogenation of the nitrile functional groups to give primary amine functional groups and does not require additional purification stage(s).
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Page/Page column 5

(2011/08/08)

Functionalized Photoreactive Compounds
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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(2008/12/08)

Process of preparing hexahydropyrimidines
This invention relates to hexahydropyrimidines (HHP) of the formula STR1 where R' is a substituted group and R is hydrogen or a substituted group; the process of preparing and the uses therefor, particularly as deterioration inhibitors in hydrocarbon fuels.
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(2008/06/13)

Triazine derivatives
The invention relates to polymers of triazine compounds containing piperidine groups which may serve as low volatile and migration-resistant light stabilizers for synthetic polymers. They have the structure STR1 and are obtained from cyanuric halides, diamines and polyalkylpiperidylamino compounds.
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(2008/06/13)

Silicone containing bis-thioether aromatic amines
A silicone containing bis-thioether aromatic amine has a chemical structure wherein an aromatic nucleus at each end of the chemical radical is chemically bonded to the remainder of the chemical radical by either sulfur, sulfoxide or sulfone.
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(2008/06/13)