- Preparation method of citronella and catalyst adopted by method
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The method comprises the following steps: carrying out selective hydrogenation reaction on limonene under the action of a hydrogenation catalyst; and after the reaction is finished, the citronellal is obtained. In the synthesis process MOFs, the adopted hydrogenation catalyst is introduced into a metal site with catalytic activity, so MOFs materials have a specific catalytic capacity, the catalytic effect of the catalyst is improved, the conversion rate and selectivity are improved, and the obtained product has better fragrance. The invention also discloses a hydrogenation catalyst for the preparation method.
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Paragraph 0032-0047
(2021/11/26)
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- Preparation method of citronellyl cyanide
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The invention discloses a preparation method of citronellyl cyanide, which comprises the following steps: under the action of an In-MOF catalyst, carrying out Mom rearrangement reaction on citronellylacid and aliphatic nitrile to obtain citronellyl cyanide. Under mild reaction conditions, the In-MOF catalyst is utilized to catalyze citronellyl acid to prepare citronellyl cyanide at high yield, and the method has the advantages of simpler reaction process, lower reaction cost, favorable environment friendliness and favorable industrial prospects.
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Paragraph 0079-0092; 0096-0097; 0103-0110
(2020/11/10)
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- A convenient reagent for the conversion of aldoximes into nitriles and isonitriles
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For the dehydroxylation of aldoximes with 4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.
- Zhang, Wei,Lin, Jin-Hong,Zhang, Pengfei,Xiao, Ji-Chang
-
supporting information
p. 6221 - 6224
(2020/06/29)
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- Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
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A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
- Fang, Wan-Yin,Qin, Hua-Li
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p. 5803 - 5812
(2019/05/14)
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- Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach
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A cyanide-free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed for the enantiospecificity that is usually not observed in enzyme catalysis. Depending on whether the E or Z isomer of the racemic aldoxime substrate was employed, one or the other enantiomer of the corresponding nitrile was formed preferentially with the same enzyme.
- Betke, Tobias,Rommelmann, Philipp,Oike, Keiko,Asano, Yasuhisa,Gr?ger, Harald
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supporting information
p. 12361 - 12366
(2017/09/06)
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- Tin or gallium-catalyzed cyanide-transition metal-free synthesis of nitriles from aldehydes or oximes
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Tin or gallium chloride catalyzed transformation of oximes or aldehydes to nitriles is described. Various nitriles were obtained in up to 99% of yields. The gram-scale reaction or the optically active dinitrile was also available. This synthetically useful method has avoided toxic organic or inorganic cyanides as well as transition or noble metal catalysts.
- Zhuang, Yan-Jun,Liu, Jie,Kang, Yan-Biao
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supporting information
p. 5700 - 5702
(2016/11/28)
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- Perfluoroalkanosulfonyl fluoride: A useful reagent for dehydration of aldoximes to nitriles
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The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.
- Yan, Zhao-Hua,Tian, Huan,Zhao, Dong-Dong,Jin, Hong-Ai,Tian, Wei-Sheng
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- Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source
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The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and α,β-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.
- An, Xiao-De,Yu, Shouyun
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supporting information
p. 5064 - 5067
(2015/11/03)
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- Postsynthesis-Treated Iron-Based Metal-Organic Frameworks as Selective Catalysts for the Sustainable Synthesis of Nitriles
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The dehydration of aldoximes to the corresponding nitriles can be performed with excellent activity and selectivity by using iron trimesate as a homogeneous catalyst. Iron trimesate has been heterogenized by synthesizing metal-organic frameworks (MOFs) from iron trimesate, that is, Fe(BTC), and MIL-100 (Fe). These materials were active and selective aldoxime dehydration catalysts, and postsynthesis-treated MIL-100 (Fe) produced the desired nitriles with 100 conversion and selectivities >90 under mild reaction conditions and in short reaction times. X-ray photoelectron spectroscopy showed the presence of different Fe species in the catalyst, and in situ IR spectroscopy combined with catalytic results indicates that the catalytic activity is associated with Fe framework species. The postsynthesis-treated MIL-100 (Fe)-NH4F can be recycled several times and has an excellent reaction scope, which gives better catalytic results than other solid acid or base catalysts.
- Rapeyko, Anastasia,Climent, Maria J.,Corma, Avelino,Concepci?n, Patricia,Iborra, Sara
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p. 3270 - 3282
(2015/10/19)
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- METHOD FOR PRODUCING NITRILE
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The present invention provides a method for producing a nitrile represented by general formula (1) (in the formula, R denotes an optionally substituted alkyl group, alkenyl group, dienyl group, aralkyl group or aryl group having a total of 3-20 carbon atoms), and the method includes heating an aldoxime represented by general formula (2) (in the formula, R denotes the same groups as those mentioned above) at 80-250°C in the presence of an alkali metal or alkaline earth metal salt of phosphoric acid (catalyst A) and distilling off water generated as the reaction progresses to outside the reaction system.
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Paragraph 0028-0029
(2015/04/15)
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- PROCESS FOR THE MANUFACTURE OF HYDROGENATED NITRILES
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The present invention relates to the manufacture and the use of specific organic compounds of formula (II) wherein n is either 1 or 2, and wherein R1 is linear C1-4 alkyl or branched C3-4 alkyl, wherein R2 is hydrogen or linear C1-4 alkyl or branched C3-4 alkyl, as aroma ingredients in flavors and fragrances. Furthermore the invention relates to new specific organic compounds and their synthesis, as well as to flavor and fragrance formulations comprising at least one of the specific organic compounds.
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Page/Page column 37; 39
(2015/03/13)
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- Process for the manufacture of hydrogenated nitriles
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The present invention relates to the manufacture and the use of specific organic compounds of formula (II) wherein n is either 1 or 2, and wherein R1 is linear C1-4 alkyl or branched C3-4 alkyl, wherein R2 is hydrogen or linear C1-4 alkyl or branched C3-4 alkyl, as aroma ingredients in flavors and fragrances. Furthermore the invention relates to new specific organic compounds and their synthesis, as well as to flavor and fragrance formulations comprising at least one of the specific organic compounds.
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Paragraph 0058
(2015/03/13)
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- Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis
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A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.
- Yin, Weiyu,Wang, Chengming,Huang, Yong
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supporting information
p. 1850 - 1853
(2013/06/04)
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- Selective reduction of dienes/polyenes using sodium borohydride/catalytic ruthenium(III) in various liquid amide aqueous mixtures
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An efficient method to effect selective reduction of several structurally diverse dienes and an unsymmetrical triene is reported. The reduction is facile at 0 °C in a liquid amide aqueous solution containing sodium borohydride in the presence of 15 mol % ruthenium(III) chloride. The chemoselectivity of the reaction is controlled by proper choice of the liquid amide solvent.
- Babler, James H.,Ziemke, David W.,Hamer, Robert M.
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p. 1754 - 1757
(2013/04/10)
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- Hydrosilanes are not always reducing agents for carbonyl compounds but can also induce dehydration: A ruthenium-catalyzed conversion of primary amides to nitriles
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A practical procedure for production of nitriles is offered by the triruthenium carbonyl cluster catalyzed dehydration of primary carboxamides with hydrosilanes under neutral conditions. This is the first example that a transition-metal-catalyzed activation of Si-H bonds does not lead to the reduction of carbonyl compounds but to dehydration. Possible mechanisms for the dehydration is discussed on the basis of NMR spectroscopic detection of intermediary species. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Hanada, Shiori,Motoyama, Yukihiro,Nagashima, Hideo
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supporting information; experimental part
p. 4097 - 4100
(2009/04/10)
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- METHOD FOR PRODUCING SATURATED NITRILES
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The invention relates to a method for producing saturated nitriles by catalytically hydrogenating the corresponding olefinically unsaturated compounds in the presence of a supported transition metal catalyst under a pressure ranging from 1 to 95 bar. The invention particularly relates to a method for producing tetra-hydrogeranonitrile (3,7-dimethyloctanenitrile) by catalytically hydrogenating geranonitrile.
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Page/Page column 12
(2008/06/13)
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- Structure-selectivity relationship in the chemoselective hydrogenation of unsaturated nitriles
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Several unsaturated nitriles of various structures (cinnamonitrile, cyclohex-1-enyl-acetonitrile, acrylonitrile, 3,3-dimethyl-acrylonitrile, geranylnitrile, and 2- and 3-pentenenitrile) with different substituents at the double bond were hydrogenated over
- Kukula, Pavel,Koprivova, Klara
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p. 161 - 171
(2007/10/03)
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- Beckmann rearrangement of oximes under very mild conditions
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A variety of ketoximes, easily prepared from the corresponding ketones, undergo the Beckmann rearrangement upon treatment with 2,4,6-trichloro[1,3,5]triazine in N,N-dimethylformamide at room temperature in excellent yields. This procedure can be applied to aldoximes for obtaining the corresponding nitriles.
- De Luca, Lidia,Giacomelli, Giampaolo,Porcheddu, Andrea
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p. 6272 - 6274
(2007/10/03)
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- Process for producing nitrile
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A nitrile having formula (2): RC≡N??(2) wherein R represents a substituted or unsubstituted alkyl, alkenyl, aralkyl or aryl group having 3 to 20 carbon atoms, is produced by a process, which comprises heating an aldoxime having formula (1): RCH═NOH??(1) wherein R is as defined above, at 80 to 250° C. in the presence of a catalyst (A) of an alkali metal or alkaline earth metal salt of a saturated or unsaturated mono- or dicarboxylic acid having 2 to 20 carbon atoms while removing product water from the reaction system by distillation.
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- A new efficient method for the conversion of aldehydes into nitriles using ammonia and hydrogen peroxide
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Aldehydes were converted into the corresponding nitriles by a homogeneous reaction with ammonia and aqueous hydrogen peroxide in the presence of copper salts or complexes under mild conditions. (C) 2000 Elsevier Science Ltd.
- Erman,Snow,Williams
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p. 6749 - 6752
(2007/10/03)
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- Effective transformation of aldoximes to nitriles by dehydration with 2-methylene-1,3-dioxepane in the presence of a Lewis acid catalyst
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The dehydration of aldoximes with 2-methylene-1,3-dioxepane (MDO) proceeds smoothly in the presence of a catalytic amount of Lewis acid such as scandium(III) triflate to give corresponding nitriles in moderate to high yields under mild conditions.
- Fukuzawa, Shin-Ichi,Yamaishi, Yasuhiro,Furuya, Hideki,Terao, Keiji,Iwasaki, Fumiaki
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p. 7203 - 7206
(2007/10/03)
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- Process for producing nitrile
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The present invention provides a process for producing a nitrile represented by the general formula (1): wherein R is alkyl, alkenyl, aralkyl or aryl, each may have a substituent, characterized by heating an aldoxime represented by the general formula (2): wherein R is as defined above, in the presence of one or more catalysts selected from hydroxides of alkali metals, alcoholates of alkali metals, hydroxides of alkaline earth metals and alcoholates of alkaline earth metals, and distilling off water formed in the course of the reaction from the reaction system. The process according to the present invention can produce a nitrile which is useful as a perfume or as a starting material for the organic synthesis of perfumes, medicines and so on in high yields and advantageously from the viewpoint of production economy.
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- Functionalization of terminal trisubstituted alkenes and derivatives thereof
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The invention relates to a process for preparing compounds having the general structure: STR1 wherein R is hydrogen or an acyclic or alicyclic fragment containing between one and about ten carbon atoms, and R1 is hydrogen or an alkyl containing between one and about four carbon atoms or an aryl group.
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- A CONVENIENT CONVERSION OF ALDOXIMES TO NITRILES UNDER PHASE-TRANSFER CONDITIONS
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A variety of aldoximes were converted into the corresponding nitriles by using carbon disulfide as dehydration reagent under phase-transfer conditions.One-pot syntheses of nitriles from aldehydes are also described.
- Shinozaki, Hiraku,Imaizumi, Mari,Tajima, Moritaka
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p. 929 - 932
(2007/10/02)
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