5810-18-4Relevant articles and documents
Preparation method of 11-cyanoundecanoic acid
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Paragraph 0030; 0032; 0033; 0035; 0036; 0038; 0039; 0041, (2019/05/08)
The invention relates to a preparation method of 11-cyanoundecanoic acid. 1,1'-peroxidation dicyclohexylamine (PXA) is subjected to a self-decomposition reaction under the effect of a rare earth metalcompound and a free radical initiator, thus the 11-cyanoundecanoic acid is obtained in a high-selectivity mode, and the PXA is generated by cyclohexanone through oxyamination. According to the process line, raw materials are simple and easy to obtain, the disadvantages that an existing process is difficult to control under the high-temperature condition and low in reaction selectivity, and products are difficult to separate are avoided, and the simple and convenient method is provided for preparation of the 11-cyanoundecanoic acid.
Amino acid preparation method comprising a step of hydroformylation of an unsaturated fatty nitrile
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, (2018/11/30)
A process for synthesizing an ω-amino acid compound of formula [in-line-formulae]HOOC—(CH2)r+2—CH2NH2,[/in-line-formulae] wherein 4≤r≤13 from a monounsaturated fatty nitrile compound of formula [in-line-formulae]CH2═CH—(CH2)r—CN[/in-line-formulae] the process comprising: 1) a step of hydroformylation of the mono unsaturated fatty nitrile compound by reacting said nitrile with carbon monoxide and di hydrogen 5e-a5 to obtain a nitrile aldehyde compound of formula HOC—(CH2)r+2-CN, then 2) a step of oxidation, in the presence of dioxygen, of the nitrile aldehyde compound to obtain a corresponding nitrile acid compound of formula HOOC—(CH2)r+2-CN, and 3) a step of reduction of the nitrile acid compound to give an w-amino acid of formula [in-line-formulae]HOOC—(CH2)r+2—CH2NH2.[/in-line-formulae]
Method for preparing 12-aminododecanoic acid
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Paragraph 0016, (2018/04/01)
The invention relates to a method for preparing 12-aminododecanoic acid and belongs to the technical field of synthesis of long carbon chain nylon monomers. The method comprises the following steps: carrying out a substitution reaction on 10-undecenoic acid and hydrogen bromide to produce 11-bromo-undecanoic acid; carrying out a hydrocyanation reaction with a cyanide reagent K[Fe(CN)6].3H2O to produce 11-cyan-undecanoic acid; and carrying out a reduction reaction, thereby obtaining the final product 12-aminododecanoic acid. The method disclosed by the invention has the advantages of being short in synthetic route, low in cost, flexible in operation, high in reaction yield, capable of obtaining the high-purity product and the like, and is very suitable for small-dose large-scale production of pharmaceutical companies or labs.
Rhodium-catalyzed tandem isomerization/hydroformylation of the bio-sourced 10-undecenenitrile: Selective and productive catalysts for production of polyamide-12 precursor
Ternel, Jeremy,Couturier, Jean-Luc,Dubois, Jean-Luc,Carpentier, Jean-Francois
, p. 3191 - 3204 (2013/12/04)
The hydroformylation of 10-undecenenitrile (1) - a substrate readily prepared from renewable castor oil - in the presence of rhodium-phosphane catalysts systems is reported. The corresponding linear aldehyde (2) can be prepared in high yields and regioselectivities with a (dicarbonyl)rhodium acetoacetonate-biphephos [Rh(acac)(CO)2-biphephos] catalyst. The hydroformylation process is accompanied by isomerization of 1 into internal isomers of undecenenitrile (1-int); yet, it is shown that the Rh-biphephos catalyst effectively isomerizes back 1-int into 1, eventually allowing high conversions of 1/1-int into 2. Recycling of the catalyst by vacuum distillation under a controlled atmosphere was demonstrated over 4-5 runs, leading to high productivities up to 230,000 mol (2)×mol (Rh)-1 and 5,750 mol (2)×mol (biphephos)-1. Attempted recycling of the catalyst using a thermomorphic multicomponent solvent (TMS) phase-separation procedure proved ineffective because the final product 2 and the Rh-biphephos catalyst were always found in the same polar phase. Auto-oxidation of the linear aldehyde 2 into the fatty 10-cyano-2-methyldecanoic acid (5) proceeds readily upon exposure to air at room temperature, opening a new effective entry toward polyamide-12. Copyright
Structural and reactivity studies of a cyanoacetic acid derivative of tungsten pentacarbonyl. X-ray structure of W(CO)5NCCH2COOH
Darensbourg, Donald J.,Atnip, Earl V.,Reibenspies, Joseph H.
, p. 4475 - 4480 (2008/10/08)
The new cyanoacetic acid complex W(CO)5NCCH2COOH (1) has been synthesized from the reaction of W(CO)5THF and NCCH2COOH. The molecular structure of 1 has been determined by X-ray diffraction methods. The compound crystallizes in the triclinic space group P1 with two molecules in a cell of dimensions a = 6.7390 (10) ?, b = 9.745 (2) ?, c = 10.241 (2) ?, α = 63.57 (2)°, β = 81.71 (2)°, γ = 76.22 (2)°. Full-matrix least-squares refinement gives final R and Rw on F of 0.026 and 0.037 for 2030 observed [F > 4σ(F)] data. The structure confirms the presence of the nitrile ligand located 2.178 (7) ? from the tungsten center, with the carboxyl groups of two molecules coupled by strong intermolecular hydrogen-bonding (O-H?O = 2.627 (3) ?). This hydrogen-bonding structure was observed as well in solution as indicated by infrared spectroscopy. The displacement of the cyanoacetic acid ligand in 1 by carbon monoxide was shown to proceed via a solvent-assisted Id process in tetrahydrofuran and by a D process in the less-interacting solvent methylene chloride. The activation parameters for these processes are consistent with the proposed mechanism, with ΔH? and ΔS? for the displacement of the NCCH2COOH ligand determined to be 19.4 kcal/mol and -14.7 eu in THF and 29.2 kcal/mol and 11.8 eu in CH2Cl2, respectively. Comparable kinetic data were observed for the tungsten complexes containing the electronically similar ligands NC(CH2)10COOH and CH3CN. The relevance of this study to the catalytic decarboxylation reaction of cyanoacetic acid in the presence of W(CO)5O2CCH2CN- is discussed.
INTERPRETING SUBSTITUENT EFFECTS ON THE CRYSTAL PACKING OF LONG-CHAIN DIACYL PEROXXIDES. THE CRYSTAL STRUCTURES OF DI(11-BROMOUNDECANOYL) PEROXIDE AND DI(UNDECANOYL) PEROXIDE
McBride, J. Michael,Bertman, Steven B.,Cioffi, Donna Z.,Segmuller, Brigitte E.,Weber, Bruce A.
, p. 1 - 24 (2007/10/02)
Although crystals of di(11-bromoundecanoyl) peroxide and di(undecanoyl) peroxide have different space groups (P43212 and C2221), the molecules pack in almost identical layers.They differ only in the nature of stacking across interfaces involving the terminal groups.Because the 90 deg twist about the O-O bond locks neighboring molecules together within the layer, each peroxide shows a single solid phase from 5K to the melting point.Analysis of the stacking pattern in terms of the six possible orientational relationships suggests special stability for an L-shaped motif of C-Br...Br-C.Other substituents create different stackings of the same layer structure to give three crystal classes and five space groups among 14 compounds.Unsymmetrical peroxides are useful both for forcing a variety of substituted chains (particularly odd-even homologues) to pack with identical layer structures, and for controlling the stacking pattern.Because structural differences are localized in the vicinity of the substituents, this series of "substitutional polytypes" will allow systematic investigation of substituent effects on the physical and chemical properties of solids.
Method for refining 11-cyano-undecanoic acid
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, (2008/06/13)
A crude 11-cyano-undecanoic acid in the form of the free acid or its ammonium salt is refined by bringing a refining gas containing ozone therein into contact with a solution of the crude 11-cyano-undecanoic acid or its ammonium salt in a substantially anhydrous organic solvent which is non-reactive with the ozone at a temperature of 0° to 100° C, for example, formic acid, acetic acid, propionic acid, chloroform, tetrachloromethane, dichloroethane or trichloroethane.
Peroxy compounds and processes for their preparation
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, (2008/06/13)
Peroxy compounds having the structural unit: EQU1 are useful for the production of monomers such as caprolactam which in turn may be polymerized to give useful polymers such as Nylon 6.
