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Cas Database

108-91-8

108-91-8

Identification

  • Product Name:Cyclohexanamine

  • CAS Number: 108-91-8

  • EINECS:203-629-0

  • Molecular Weight:99.1759

  • Molecular Formula: C6H13 N

  • HS Code:2921.30

  • Mol File:108-91-8.mol

Synonyms:Cyclohexylamine(6CI,8CI);1-Aminocyclohexane;1-Cyclohexylamine;Aminocyclohexane;Aminohexahydrobenzene;Benzenamine, hexahydro-;Hexahydroaniline;Monocyclohexylamine;Cyclohexylamine Acid;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes: C:Corrosive;

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H312 Harmful in contact with skin H314 Causes severe skin burns and eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Refer for medical attention . Give one or two glasses of water to drink. This is classified as very toxic -- probable oral lethal dose is 50-500 mg/kg or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. It is considered a nerve poison. This is a weak methemoglobin-forming substance. (EPA, 1998) Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does Not drool. Administer activated charcoal ... . Cover skin buRNs with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Solid streams of water may be ineffective and spread material. When heated to decomposition, it emits highly toxic fumes. Vapor may travel a considerable distance to source of ignition and flash back. Toxic oxides of nitrogen are produced during combustion. Nitric acid; reacts vigorously with oxiding materials. Stable, avoid physical damage, storage with oxidizing material. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Evacuate danger area! Personal protection: self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Stop or control the leak, if this can be done without undue risk. Eliminate all ignition sources. Use water spray to cool and disperse vapors, protect personnel, and dilute spills to form nonflammable mixtures. Approach release from upwind. Absorb in noncombustible material for proper disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from acids, oxidants, aluminium, copper, zinc and food and feedstuffs. Well closed.Outside or detached storage is preferred. Avoid oxidizing materials, acid, and sources of halogen. Store in a cool, dry well-ventilated location.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted avg: 10 ppm (40 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 430 Articles be found

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Smith et al.

, p. 294 (1952)

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Reaction of Phospholes with Aldimines: A One-Step Synthesis of Chelating, Alpha-C2-Bridged Biphospholes

Hu, Zhengsong,Li, Zongyang,Zhao, Kang,Tian, Rongqiang,Duan, Zheng,Mathey, Fran?ois

, p. 3518 - 3520 (2015)

Phospholes react with aldimines at 170°C in the presence of mild Lewis acids to give C2-bridged biphospholes in good yields. The mechanism includes a series of [1,5] shifts of the P-substituents around the phosphole ring, a P-H + aldimine condensation, and the formation of a transient three-membered ring that dimerizes.

A Selective Electrocatalytic Cleavage of the Benzyloxycarbonyl Group from Peptides

Casadei, M. Antonietta,Pletcher, D.

, p. 1118 - 1119 (1987)

An electrosynthetic procedure for the cleavage of the benzyloxycarbonyl group from protected amino acids and peptides is described.It is based on the use of a high surface area palladium cathode in methanol/acetic acid and gives an excellent selectivity under very mild conditions.

POLYMERIC METAL COMPLEX CATALYSTS IN HYDROGENATION OF NITROBENZENE

Perchenko, V. N.,Obydennova, I. V.,Shanazarova, I. M.,Nametkin, N. S.

, p. 615 - 617 (1982)

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Formal asymmetric biocatalytic reductive amination

Koszelewski, Dominik,Lavandera, Ivan,Clay, Dorina,Guebitz, Georg M.,Rozzell, David,Kroutil, Wolfgang

, p. 9337 - 9340 (2008)

All for one: A combination of three biocatalysts (ω-transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α-chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction. (Chemical Equation Presented).

Commercial catalysts screening for liquid phase nitrobenzene hydrogenation

Couto, Clara Sá,Madeira, Luis M.,Nunes, Clemente Pedro,Araújo, Paulo

, p. 152 - 164 (2016)

In this work, a series of commercially available materials was screened for the catalytic hydrogenation of nitrobenzene (NB). The materials revealed different performances, particularly different activities in what concerns the NB conversion, and notably diverse selectivities towards the industrially desired reaction product, aniline (ANL). The catalysts' active phases are based on Pd and Ni (respectively groups I and II), namely 1 wt.% Pd/Al2O3 (catalyst I.1), 0.3 wt.% Pd/Al2O3 (catalyst I.2), 0.3 wt.% Pd/Al2O3 (catalyst I.3), and 50 wt.% NiO/(Al2O3 + SiO2) (catalyst II.1). The fresh and used materials were characterized by several physical-chemical techniques, specifically scanning electron microscopy (SEM), high resolution transmission electron microscopy (HRTEM), nitrogen adsorption (with BET surface area determination), X-ray diffraction (XRD), H2 temperature-programmed reduction (TPR), inductively coupled plasma mass spectrometry (ICP-MS) and elemental (CHNS) analysis. It was shown that the catalysts are stable in the conditions studied and no deactivation was found. The characterization results allowed explaining the catalytic behavior of the tested materials. In particular, catalyst I.1 was found to be the less active, probably due to its much lower BET surface area (and larger Pd particle size). On the other hand, catalyst I.2 was the more active, which was well correlated to the smaller average particle size (along with narrower Pd particle size distribution) and smaller pellet size, although the active metal content is low. Finally, it was observed that catalyst II.1 is the most selective towards light by-products (benzene (Bz), cyclohexylamine (CHA), cyclohexanol (CHOL) and cyclohexanone (CHONA)), probably due to its lower pore size dimensions.

Anti-Markovnikov Hydroamination of Alkenes with Aqueous Ammonia by Metal-Loaded Titanium Oxide Photocatalyst

Park, Soyeong,Jeong, Jaeyoung,Fujita, Ken-Ichi,Yamamoto, Akira,Yoshida, Hisao

, p. 12708 - 12714 (2020)

A completely new route was established to synthesize valuable primary amines from alkenes by using aqueous ammonia, that is, a simple photocatalytic hydroamination of alkenes using aqueous ammonia with a metal-loaded TiO2 photocatalyst. Although the photochemical hydroamination prefers to form amines according to the Markovnikov rule, the new photocatalytic hydroamination gives anti-Markovnikov products predominantly. With an Au-loaded TiO2 photocatalyst, the amine yield reached up to 93% and the regioselectivity of anti-Markovnikov products was above 98%. The reaction mechanism was proposed for the new photocatalytic hydroamination.

Poly(propylene sulfide)-borane: Convenient and versatile reagent for organic synthesis

Smith, Keith,Balakit, Asim A.,El-Hiti, Gamal A.

, p. 7834 - 7839 (2012)

Poly(trimethylene sulfide)-borane adduct has been used as an efficient borane reagent in hydroboration reactions to produce various organoboranes, which have then been used without isolation in further reactions that involve single, double and triple migrations of alkyl groups. The presence of the polymer causes no problems, but there are practical advantages associated with its use, including lack of odour and easy recoverability.

Doped ordered mesoporous carbons as novel, selective electrocatalysts for the reduction of nitrobenzene to aniline

Daems, Nick,Risplendi, Francesca,Baert, Kitty,Hubin, Annick,Vankelecom, Ivo F. J.,Cicero, Giancarlo,Pescarmona, Paolo P.

, p. 13397 - 13411 (2018)

Ordered mesoporous carbons (OMCs) doped with nitrogen, phosphorus or boron were synthesised through a two-step nanocasting method and studied as electrocatalysts for the reduction of nitrobenzene to aniline in a half-cell setup. The nature of the dopant played a crucial role in the electrocatalytic performance of the doped OMCs, which was monitored by LSV with a rotating disk electrode setup. The incorporation of boron generated the electrocatalysts with the highest kinetic current density, whereas the incorporation of phosphorus led to the lowest overpotential. Doping with nitrogen led to intermediate behaviour in terms of onset potential and kinetic current density, but provided the highest selectivity towards aniline, thus resulting in the most promising electrocatalyst developed in this study. Density functional theory calculations allowed explaining the observed difference in the onset potentials between the various doped OMCs, and indicated that both graphitic N and pyrdinic N can generate active sites in the N-doped electrocatalyst. A chronoamperometric experiment over N-doped OMC performed at -0.75 V vs. Fc/Fc+ in an acidic environment, resulted in a conversion of 61% with an overall selectivity of 87% to aniline. These are the highest activity and selectivity ever reported for an electrocatalyst for the reduction of nitrobenzene to aniline, making N-doped OMC a promising candidate for the electrochemical cogeneration of this industrially relevant product and electricity in a fuel cell setup.

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Kailan,Stueber

, p. 90,97 (1933)

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Selective reductions. Part 60: Chemoselective reduction of organyl azides with dichloroborane-dimethyl sulfide

Salunkhe, Ashok M.,Veeraraghavan Ramachandran,Brown, Herbert C.

, p. 10059 - 10064 (2002)

The rate and stoichiometry of the reduction of an organyl azide with BH3·THF was examined under standardized conditions at room temperature. Borane derivatives, such as dialkyl-, alkoxy-, and haloboranes were also examined for the reduction of azides. This study revealed BHCl2·SMe2 to be the most suitable reagent for the reduction of azides. The chemoselectivity of this reagent was also studied by reducing n-hexyl azide in the presence of representative series of functional groups, including esters, halides, nitriles, and nitro groups. BHCl2·SMe2 reduces azides in the presence of all of the above functional groups as well as olefins. Taking advantage of the differences in reactivity of BHCl2·SMe2 and BH3·THF or BH3·SMe2, it is now possible to reduce selectively an azide in the presence of olefins or to hydroborate an olefin in the presence of azides by a judicious choice of the reagent.

LIQUID PHASE CO-AMMONOLYSIS OF PHENOL AND CYCLOHEXANOL WITH PALLADIUM-ON-CARBON CATALYST

Hamada, Hideaki,Yamamoto, Makoto,Matsuzaki, Takehiko,Wakabayashi, Katsuhiko

, p. 239 - 240 (1980)

In the presence of Pd/C catalyst, phenol and cyclohexanol are aminated simultaneously to aniline and cyclohexylamine by ammonolysis, while conversion of phenol or cyclohexanol alone is very poor.It is suggested that this amination is caused by hydrogen transfer between phenol and cyclohexanol.Ru/C, Rh/C, and Pt/C are ineffective for this co-amination.

Fe/Fe2O3@N-dopped Porous Carbon: A High-Performance Catalyst for Selective Hydrogenation of Nitro Compounds

Yun, Ruirui,Hong, Lirui,Ma, Wanjiao,Jia, Weiguo,Liu, Shoujie,Zheng, Baishu

, p. 724 - 728 (2019)

Herein, we designed and prepared a novel Fe/Fe2O3-based catalyst, in which a remarkable synergistic effect has been revealed between Fe and Fe2O3 encapsulated in N-doping porous carbon. The Fe-based catalysts were fabricated via pyrolysis a mixture of MIL-101(Fe) and melamine. The catalyst exhibits exceptionally high catalytic activity (TOFs up to 8898 h?1 which is about 100 times higher than the similar kinds of catalysts) and chemoselectivity for nitroarene reduction under mild conditions.

Perbrominated 2-nitrotetraphenylporphyrins: Electrochemical and axial ligation properties

Bhyrappa, Puttaiah,Purushothaman, Bhavana

, p. 238 - 242 (2001)

A new series of perbrominated 2-nitro-5,10,15,20-tetraphenylporphyrins, H2TPPBrn(NO2) (n = 6 and 7) and their metal (CuII and ZnII) complexes have been synthesised and characterised. The presence of mixed electron withdrawing (bromo- and nitro-) substituents at the β-pyrrole positions induces interesting electrochemical and axial ligation properties. Perbrominated nitroporphyrins exhibit two successive one electron redox potentials with a positive shift of >100 mV relative to their corresponding octabromotetraphenylporphyrin (MTPPBr8) complexes. Axial ligation of various nitrogenous bases to ZnTPPBrn(NO2) complexes showed facile ligand binding with >50% enhancement in the equilibrium constants, Keq, relative to ZnTPPBr8. Surprisingly, MTPPBrn(NO2) complexes show similar axial ligation and electrochemical redox behaviour. The anodic shift in electrochemical redox potentials and enhanced Keq of MTPPBrn(NO2) complexes have been attributed to the increased electron deficiency of the porphyrin π-system.

Amberlyst-15(H+)-NaBH4-LiCl: An effective reductor for oximes and hydrazones

Baruah, Bipul,Dutta, Manu P.,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.

, p. 409 - 410 (1999)

A simple and mild procedure reduces oximes and hydrazones on amberlyst 15(H+) support with LiCl-NaBH4 to the corresponding amines and hydrazines respectively in high yield and purity.

Ligand-accelerated activation of strong C-H bonds of alkanes by a (salen)ruthenium(VI)-nitrido complex

Man, Wai-Lun,Lam, William W. Y.,Kwong, Hoi-Ki,Yiu, Shek-Man,Lau, Tai-Chu

, p. 9101 - 9104 (2012)

Kinetic and mechanistic studies on the intermolecular activation of strong C-H bonds of alkanes by a (salen)ruthenium(VI) nitride were performed. The initial, rate-limiting step, the hydrogen atom transfer (HAT) from the alkane to RuVI≡N, generates RuV=NH and RC.HCH 2R. The following steps involve N-rebound and desaturation. Copyright

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Schultz

, p. 1039,1040 (1960)

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New Photolabile Amino Protecting Groups: Photogeneration of Amines from carbonyl Carbamates

Cameron, James F.,Willson, C. Grant,Frechet, Jean M. J.

, p. 923 - 924 (1995)

A novel class of photolabile amino protecting groups, based on carbonyl groups, is presented and their scope and versatility demonstrated by the photogeneration of free primary and secondary amines.

Synthesis of 1,4-diaminocyclohexane in supercritical ammonia

Fischer,Mallat,Baiker

, p. 289 - 291 (1999)

The amination of 1,4-cyclohexanediol in supercritical ammonia has been studied in a continuous fixed-bed reactor at 135 bar. An unsupported cobalt catalyst stabilized by 5 wt% Fe afforded the main reaction products 4-aminocyclohexanol and 1,4-diaminocyclohexane with a cumulative selectivity of 97% at 76% conversion. Excess of ammonia and short contact time favored the desired reactions. At low and high conversions the amination selectivity decreased due to the formation of dimers and oligomers and degradation products. Recycling of the unreacted diol and amino alcohol intermediate can provide an alternative economic process for the synthesis of 1,4-diaminocyclohexane.

Noble metal nanoparticles stabilized by hyper-cross-linked polystyrene as effective catalysts in hydrogenation of arenes

Bakhvalova, Elena S.,Bykov, Alexey V.,Demidenko, Galina N.,Kiwi-Minsker, Lioubov,Mikheev, Alexey V.,Nikoshvili, Linda Z.,Pinyukova, Arina O.,Sulman, Mikhail G.

, (2021)

This work is addressing the arenes’ hydrogenation—the processes of high importance for petrochemical, chemical and pharmaceutical industries. Noble metal (Pd, Pt, Ru) nanoparticles (NPs) stabilized in hyper-cross-linked polystyrene (HPS) were shown to be active and selective catalysts in hydrogenation of a wide range of arenes (monocyclic, condensed, substituted, etc.) in a batch mode. HPS effectively stabilized metal NPs during hydrogenation in different medium (water, organic solvents) and allowed multiple catalyst reuses.

Instantaneous SmI2/H2O/amine mediated reduction of nitroalkanes and α,β-unsaturated nitroalkenes

Ankner, Tobias,Hilmersson, G?ran

, p. 5707 - 5710 (2007)

A rapid method for efficient reduction of nitroalkanes and α,β-unsaturated nitroalkenes using SmI2/H2O/amine has been developed.

Reductive amination of ketones: Novel one-step transfer hydrogenations in batch and continuous-flow mode

Falus, Péter,Boros, Zoltán,Hornyánszky, Gábor,Nagy, József,Darvas, Ferenc,ürge, László,Poppe, László

, p. 1310 - 1312 (2011)

Various ketones were efficiently transformed into the corresponding amines using ammonium formate in the presence of Zn dust or 10% Pd/C. The low-cost Zn dust method proved to be effective in amine formation from carbonyl groups at the benzylic side-chain position of aromatic systems, whereas 10% Pd/C was an efficient catalyst in the reductive aminations of carbonyl groups non-conjugated with any π-system. The 10% Pd/C-catalyzed reductions were performed more effectively in a continuous-flow X-Cube reactor than in the batch system.

Essential role of heterocyclic structure of N-alkylated 2-pyrrolidone derivatives for recycling uranium from spent nuclear fuels

Inoue, Tsubasa,Kazama, Hiroyuki,Takao, Koichiro,Tsushima, Satoru

, p. 846 - 853 (2020)

In a simple and versatile reprocessing method for recycling U and Pu from spent nuclear fuels, cyclic amides like Nalkylated 2-pyrrolidone derivatives (NRPs) are exclusively employed. However, there has been no convincing rational to explain why such a heterocyclic structure is required. To answer this question, we employed N-cyclohexyl-2-pyrrolidone (NCP) and N-cyclohexylformamide (NCF) as cyclic and acyclic monodentate amides, and focused on the following 3 topics in this study; (1) structural chemistry of their uranyl dinitrato complexes, (2) precipitation behavior of UO22+ from HNO3(aq) by using these amides, and (3) their chemical stability in HNO3(aq) simulating the reprocessing conditions for spent nuclear fuels. Fundamental coordination chemistry of UO2(NO3)2(L)2 (L = NCP, NCF) was found to be common to both L, regardless of the presence or absence of the pyrrolidone ring. Furthermore, both L exhibit comparable capability in precipitation of UO22+ from HNO3(aq). The most critical difference between NCP and NCF was found in their chemical stability in HNO3(aq), where NCF was gradually decomposed through acid-catalyzed hydrolysis, while NCP remained intact for at least 4 h. In conclusion, the pyrrolidone ring of NRPs plays an important role to sterically protect the carbonyl C from nucleophilic hydrolysis which initiates the amide C(=O)N bond cleavage.

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Adkins,Cramer,Connor

, p. 1402 (1931)

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Breuer,Schnitzer

, p. 301,307 (1936)

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Synthesis of polycyclic tertiary carbinamines by samarium diiodide mediated cyclizations of indolyl sulfinyl imines

Rao, Chintada Nageswara,Lentz, Dieter,Reissig, Hans-Ulrich

, p. 2750 - 2753 (2015)

Samarium diiodide mediated cyclizations of N-acylated indole derivatives bearing sulfinyl imine moieties afforded polycyclic tertiary carbinamines with moderate to excellent diastereoselectivities. Lithium bromide and water turned out to be the best additives to achieve these transformations in good yields. Using enantiopure sulfinyl imines the outcome strongly depends on the reactivity of the indole moiety. Whereas with unactivated indole derivatives desulfinylation and formation of racemic products was observed, indoles bearing electron-withdrawing substituents at C-3 afforded the polycyclic products with intact N-sulfinyl groups and with excellent diastereoselectivity, finally allowing the preparation of enantiopure tertiary carbinamines. The mechanisms of these processes are discussed.

New and mild allyl carbamate deprotection method catalyzed by electrogenerated nickel complexes

Franco,Dunach

, p. 7333 - 7336 (2000)

A Ni(II)-catalyzed electrochemical procedure for the simple and mild deprotection of allyl carbamates to the corresponding amines is described. The amines are obtained in yields of 40-99% and the method is compatible with several functional groups. Electrolyses are carried out in DMF or in THF in single-compartment cells in the presence of a consumable zinc anode. (C) 2000 Elsevier Science Ltd.

A ruthenium and palladium bimetallic system superior to a rhodium co-catalyst for TiO2-photocatalyzed ring hydrogenation of aniline to cyclohexylamine

Araki, Sakae,Kominami, Hiroshi,Nakanishi, Kousuke,Tanaka, Atsuhiro

, p. 212 - 217 (2020)

Cyclohexylamine (CHA) is used as an important raw material in chemical industries. Since the production of CHA requires a high temperature and excess amounts of hydrogen gas (H2) and ammonia, the development of a simple reaction operated under milder conditions using a safe compound is indispensable for achieving sustainable chemistry. A highly selective ring hydrogenation of aniline (AN) to CHA over a titanium(IV) oxide photocatalyst having a co-catalyst in water at room temperature, in which oxalic acid was used as the hydrogen source in place of H2, is described in this paper. Among TiO2 photocatalysts having co-catalysts, Rh-TiO2 showed high activity for CHA production, while Pd-TiO2 and Ru-TiO2 showed negligible activity. When a bimetallic photocatalyst, Ru/Pd-TiO2, was used, the yield was larger than that when Rh-TiO2 was used. Metal particles loaded on TiO2 were observed by using TEM, and electronic states of Ru and Pd were evaluated by using XPS. Interactions among metal, AN and CHA were investigated through adsorption experiments. Based on the results, active sites for AN hydrogenation are discussed.

A magnetically separable gold catalyst for chemoselective reduction of nitro compounds

Park, Sungho,Lee, In Su,Park, Jaiwook

, p. 395 - 399 (2013)

Magnetically separable gold-nanoparticle catalyst was prepared, and it showed excellent activity for chemoselective reduction of nitroarenes with hydrosilanes. The Royal Society of Chemistry 2013.

Reduction of O-acyl oximes with sodium borohydride/iodine system

Barbry,Champagne

, p. 3503 - 3507 (1995)

O-acyl derivatives of aldoximes and ketoximes are reduced in good yields to the corresponding amines with sodium borohydride-iodine system.

O-(DIPHENYLPHOSPHINYL)HYDROXYLAMINE: A NEW REAGENT FOR ELECTROPHILIC C-AMINATION

Colvin, Ernest W.,Kirby, Gordon W.,Wilson, Arthur C.

, p. 3835 - 3836 (1982)

O-(Diphenylphosphinyl)hydroxylamine efficiently aminates a variety of stabilised carbanions and certain Grignard reagents.

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O'Neill et al.

, p. 4775,4779 (1973)

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Low-temperature deacylation of N-monosubstituted amides

Spaggiari, Alberto,Blaszczak, Larry C.,Prati, Fabio

, p. 3885 - 3888 (2004)

(Chemical Equation Presented) The (PhO)3P-Cl2 reagent, prepared in situ by titrating a solution of triphenyl phosphite with chlorine, is used to convert N-monosubstituted amides into their corresponding amines. The reaction, if compared to other traditional methods, shows the advantage of very mild conditions and low temperature (-30°C→rt).

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Smith,Bedoit

, p. 1085,1095, 1096, 1102 (1951)

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Highly selective one-step hydrogenation of nitrobenzene to cyclohexylamine over the supported 10% Ni/carbon catalysts doped with 3‰ Rh

Lu, Xinhuan,Chen, Yang,Zhao, Zhenshuang,Deng, Hao,Zhou, Dan,Wei, Changcheng,Nie, Renfeng,Xia, Qinghua

, p. 15354 - 15361 (2016)

The carbon supported 10% Ni catalysts doped with 3‰ Rh have been prepared by an impregnation method. These catalysts have been used to catalyze the one-step hydrogenation of nitrobenzene to cyclohexylamine. The results show that the 3‰ Rh-10% Ni/CSC (biocarbon) catalyst exhibits an excellent performance to achieve 100 mol% conversion of nitrobenzene and 91.6% selectivity of cyclohexylamine under reaction conditions of 3.5 MPa and 140 °C. The recycling tests reveal recyclable stability of 3‰ Rh-10% Ni/CSC. This catalyst is active for the hydrogenation of a series of electron-deficient nitrobenzenes. Some factors such as the type of carriers, the content of Ni and Rh, the type of metals and additives play important roles in controlling the selective hydrogenation.

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Mueller,Bleier

, p. 399 (1928)

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Highly-dispersed and size-controlled ruthenium nanoparticles on carbon nanofibers: Preparation, characterization, and catalysis

Motoyama, Yukihiro,Takasaki, Mikihiro,Higashi, Kenji,Yoon, Seong-Ho,Mochida, Isao,Nagashima, Hideo

, p. 876 - 877 (2006)

Facile synthesis of ruthenium nanoparticles supported on the carbon nanofibers (CNFs) is accomplished by thermal decomposition of Ru 3(CO)12; ruthenium species on the platelet-type CNF are dispersed homogeneously and selectively on the edge of the graphite layers with narrow size distributions and behaves as an excellent catalyst for arene hydrogenation. Copyright

Unprecedented efficient hydrogenation of arenes in biphasic liquid-liquid catalysis by re-usable aqueous colloidal suspensions of rhodium

Schulz, Juergen,Roucoux, Alain,Patin, Henri

, p. 535 - 536 (1999)

A reduced aqueous colloidal suspension of rhodium shows efficient activity for the catalytic hydrogenation of various benzene derivatives under biphasic conditions at room temperature and under atmospheric hydrogen pressure; the aqueous phase containing the Rh(0) particles can be re-used for further runs with a complete conservation of activity.

Fe/Fe3C Encapsulated in N-Doped Carbon Tubes: A Recyclable Catalyst for Hydrogenation with High Selectivity

Yun, Ruirui,Zhang, Shi,Ma, Wanjiao,Lv, Xiao,Liu, Shoujie,Sheng, Tian,Wang, Suna

, p. 9469 - 9475 (2019)

Herein, a series of Fe-based catalysts have been designed and prepared by grinding a mixture of MIL-88d and melamine, and then the mixture was followed by pyrolysis. An unusual Fe/Fe3C-activated site is uniformly encapsulated in the N-doped carbon tubes obtained by pyrolysis of the film-like nanocrystals of MIL-88d. Experimental characterizations and theoretical calculations demonstrate that the surface N sites can effectively trap the nitrobenzene and aniline by their phenyl groups with the formation of three C-N bonds that made the catalyst exhibit excellent catalytic activity (turnover frequencies of ≤11268 h-1 calculated on the basis of nitrobenzene) and chemoselectivity for the reduction of nitro derivatives under facile conditions.

Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases

Cosgrove, Sebastian C.,Grogan, Gideon,Mangas-Sanchez, Juan,Marshall, James R.,Palmer, Ryan B.,Ramsden, Jeremy I.,Sharma, Mahima,Thorpe, Thomas W.,Turner, Nicholas J.

, p. 5052 - 5057 (2020)

Chiral primary amines are important intermediates in the synthesis of pharmaceutical compounds. Fungal reductive aminases (RedAms) are NADPH-dependent dehydrogenases that catalyse reductive amination of a range of ketones with short-chain primary amines supplied in an equimolar ratio to give corresponding secondary amines. Herein we describe structural and biochemical characterisation as well as synthetic applications of two RedAms fromNeosartoryaspp. (NfRedAm andNfisRedAm) that display a distinctive activity amongst fungal RedAms, namely a superior ability to use ammonia as the amine partner. Using these enzymes, we demonstrate the synthesis of a broad range of primary amines, with conversions up to >97% and excellent enantiomeric excess. Temperature dependent studies showed that these homologues also possess greater thermal stability compared to other enzymes within this family. Their synthetic applicability is further demonstrated by the production of several primary and secondary amines with turnover numbers (TN) up to 14 000 as well as continous flow reactions, obtaining chiral amines such as (R)-2-aminohexane in space time yields up to 8.1 g L?1h?1. The remarkable features ofNfRedAmand NfisRedAm highlight their potential for wider synthetic application as well as expanding the biocatalytic toolbox available for chiral amine synthesis.

ELECTROCATALYTIC HYDROGENATION OF ORGANIC COMPOUNDS ON DEVARDA COPPER AND RANEY NICKEL ELECTRODES IN BASIC MEDIA

Belot, Gerard,Desjardins, Sylvie,Lessard, Jean

, p. 5347 - 5350 (1984)

Using Devarda copper and Raney nickel electrodes, nitrobenzene, nitrocyclohexane, p-nitroacetophenone, N-methyl-p-anisaldehyde imine, benzophenone, and phenanthrene have been electrocatalytically hydrogenated with high chemical and current efficiency.

Synthesis of aziridinosteroids

Di Chenna,Dauban,Ghini,Burton,Dodd

, p. 443 - 444 (2000)

11α,12α-aziridinosteroids (2a, b, c) were prepared from 5β-H-11-pregnene-3, 20-dione (1) using different iminophenyliodinanes and cloramine aziridination reagents.

Post-functionalized iridium-Zr-MOF as a promising recyclable catalyst for the hydrogenation of aromatics

Rasero-Almansa, Antonia M.,Corma, Avelino,Iglesias, Marta,Sanchez, Felix

, p. 3522 - 3527 (2014)

The multifunctional heterogeneous catalyst iridium-Zr-based MOF is able to effectively catalyze the hydrogenation of aromatic compounds in high yields under mild conditions. The catalyst was found to be highly active and reusable, giving similar reactivity and selectivity after at least five catalytic uses. This journal is the Partner Organisations 2014.

More efficient palladium catalyst for hydrogenolysis of benzyl groups

Li, Yong,Manickam, Govindaswamy,Ghoshal, Atanu,Subramaniam, Prasad

, p. 925 - 928 (2006)

-

A simple and reproducible method for the synthesis of silica-supported rhodium nanoparticles and their investigation in the hydrogenation of aromatic compounds

Mevellec, Vincent,Nowicki, Audrey,Roucoux, Alain,Dujardin, Christophe,Granger, Pascal,Payen, Edmond,Philippot, Karine

, p. 1214 - 1219 (2006)

Colloidal suspensions of rhodium nanoparticles have been easily prepared in aqueous solution by chemical reduction of the precursor RhCl 3·3H2O in the presence of the surfactant N,N-dimethyl-N-cetyl-N-(2-hydroxyethyl)ammonium chloride (HEA16Cl) and further used to immobilize rhodium nanoparticles on silica by simple impregnation. The obtained silica-supported rhodium nanoparticles have been investigated by adapted characterization methods such as transmission electron microscopy and X-ray photoelectron spectroscopy. A particle size increase from 2.4 to 5 nm after the silica immobilization step and total elimination of the surfactant has been observed. This "heterogeneous" catalyst displayed good activities for the hydrogenation of mono-, di- alkylsubstituted and/or functionalized aromatic derivatives in water under atmospheric hydrogen pressure and at room temperature. In all cases, the catalyst could be recovered several times after a simple decantation or filtration and reused without any significant loss in catalytic activity. This supported catalyst has also been tested under higher hydrogen pressure giving rise to TOFs reaching 6430 h -1 at 30 bar and in terms of catalytic lifetime 30 000 TTO in 8.5 h for pure anisole hydrogenation at 40 bar. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

Brown et al.

, p. 3565 (1964)

-

Kirchhoff

, p. 2533 (1976)

-

VERSATILE POLYMER-BOUND RHODIUM CATALYSTS. FACILE HYDROGENATION OF AROMATIC COMPOUNDS IN THE LIQUID PHASE

Okano, Tamon,Tsukiyama, Katsunori,Konishi, Hisatoshi,Kiji, Jitsuo

, p. 603 - 606 (1982)

Immobilized complexes prepared from 2 (nbd=norbornadiene) and phosphinated polydiacetylene or silica are efficient catalysts for the hydrogenation of arenes under mild conditions.However, the homologous catalyst supported on a phosphinated polystyrene is not active.

Green Synthesis of Rhodium Nanoparticles that are Catalytically Active in Benzene Hydrogenation and 1-Hexene Hydroformylation

Alsalahi, Waleed,Tylus, Wlodzimierz,Trzeciak, Anna M.

, p. 2051 - 2058 (2018)

Rhodium nanoparticles (Rh NPs) were prepared according to a green method based on the reduction of (acetylacetonato)dicarbonylrhodium(I), Rh(acac)(CO)2, in water at 80 °C. The nanoparticles, which were obtained without the addition of a reducing agent, were stabilized by polyvinylpyrrolidone (PVP) or polyvinyl alcohol (PVA) polymers and characterized by TEM (transmission electron microscopy), XPS (X-ray photoelectron spectroscopy), and XRD (X-ray powder diffraction) methods. The excellent catalytic activity of these Rh NPs was evidenced in the hydrogenation of benzene to cyclohexane. In the presence of PPh3, Rh NPs formed a highly active system in the hydroformylation of 1-hexene. In this system, they acted as a source of soluble rhodium species. Rh NPs were also synthesized in water using rhodium(II) acetate, Rh2(OAc)4, and rhodium(III) chloride, RhCl3, as rhodium sources, and their catalytic activity was compared with that of the rhodium precursors.

-

Bevan et al.

, p. 165,170 (1978)

-

N,N-Chelate nickel(II) complexes bearing Schiff base ligands as efficient hydrogenation catalysts for amine synthesis

Xu, Mengyin,Wang, Yang,Zhou, Yifeng,Yao, Zi-Jian

, (2021/12/09)

Five N, N-chelate nickel (II) complexes bearing N-(2-pyridinylmethylene)-benzylamine ligands with different substituent groups were synthesized in good yields. The nickel complexes exhibited prominent catalytic efficiency toward amine synthesis from nitro compounds by using NaBH4 or H2 as hydrogen source through two catalytic systems. Various amines with different substituents were obtained in moderate to excellent yields. All substrates with electron-donating and electron-withdrawing properties were tolerated in the two reduction systems. Given the efficient catalytic activity, broad substance scope, and mild reduction conditions, the nickel catalysts have potential applications in industrial production.

Palladium supported on magnesium hydroxyl fluoride: An effective acid catalyst for the hydrogenation of imines and N-heterocycles

Agbossou-Niedercorn, Francine,Corre, Yann,Dongare, Mohan K.,Kemnitz, Erhard,Kokane, Reshma,Michon, Christophe,Umbarkar, Shubhangi B.

supporting information, p. 19572 - 19583 (2021/11/04)

Palladium catalysts supported on acidic fluorinated magnesium hydroxide Pd/MgF2-x(OH)x were prepared through precipitation or impregnation methods. Applications to the hydrogenation of various aldimines and ketimines resulted in good catalytic activities at mild temperatures using one atmosphere of hydrogen. Quinolines, pyridines and other N-heterocycles were successfully hydrogenated at higher temperature and hydrogen pressure using low palladium loadings and without the use of any acid additive. Such reactivity trend confirmed the positive effect of the Br?nsted and Lewis acid sites from the fluorinated magnesium hydroxide support resulting in the effective pre-activation of N-heterocycle substrates and therefore in the good catalytic activity of the palladium nanoparticles during the hydrogenations. As demonstrated in the hydrogenation of imines, the catalyst was recycled up to 10 times without either loss of activity or palladium leaching. This journal is

MATERIALS COMPRISING CARBON-EMBEDDED COBALT NANOPARTICLES, PROCESSES FOR THEIR MANUFACTURE, AND USE AS HETEROGENEOUS CATALYSTS

-

Page/Page column 17; 19-20, (2021/03/13)

The present invention relates to catalytically active material, comprising grains of non-graphitizing carbon with cobalt nanoparticles dispersed therein, wherein dP, the average diameter of cobalt nanoparticles in the non-graphitizing carbon grains, is in the range of 1 nm to 20 nm, D, the average distance between cobalt nanoparticles in the non-graphitizing carbon grains, is in the range of 2 nm to 150 nm, and ω, the combined total mass fraction of metal in the non-graphitizing carbon grains, is in the range of 30 wt% to 70 wt% of the total mass of the non-graphitizing carbon grains, and wherein dP, D and ω conform to the following relation: 4.5 dP / ω > D ≥ 0.25 dP / ω. The present invention, further, relates to a process for the manufacture of material according to the invention, as well as its use as a catalyst.

Development and Application of Efficient Ag-based Hydrogenation Catalysts Prepared from Rice Husk Waste

Unglaube, Felix,Kreyenschulte, Carsten Robert,Mejía, Esteban

, p. 2583 - 2591 (2021/04/09)

The development of strategies for the sustainable management and valorization of agricultural waste is of outmost importance. With this in mind, we report the use of rice husk (RH) as feedstock for the preparation of heterogeneous catalysts for hydrogenation reactions. The catalysts were prepared by impregnating the milled RH with a silver nitrate solution followed by carbothermal reduction. The composition and morphology of the prepared catalysts were fully assessed by IR, AAS, ICP-MS, XPS, XRD and STEM techniques. This novel bio-genic silver-based catalysts showed excellent activity and remarkable selectivity in the hydrogenation of nitro groups in both aromatic and aliphatic substrates, even in the presence of reactive functionalities like halogens, carbonyls, borate esters or nitriles. Recycling experiments showed that the catalysts can be easily recovered and reused multiple times without significant drop in performance and without requiring re-activation.

Rhodium-terpyridine Catalyzed Transfer Hydrogenation of Aromatic Nitro Compounds in Water

Liu, Yuxuan,Miao, Wang,Tang, Weijun,Xue, Dong,Xiao, Jianliang,Wang, Chao,Li, Changzhi

supporting information, p. 1725 - 1729 (2021/06/01)

A rhodium terpyridine complex catalyzed transfer hydrogenation of nitroarenes to anilines with i-PrOH as hydrogen source and water as solvent has been developed. The catalytic system can work at a substrate/catalyst (S/C) ratio of 2000, with a turnover frequency (TOF) up to 3360 h?1, which represents one of the most active catalytic transfer hydrogenation systems for nitroarene reduction. The catalytic system is operationally simple and the protocol could be scaled up to 20 gram scale. The water-soluble catalyst bearing a carboxyl group could be recycled 15 times without significant loss of activity.

Process route upstream and downstream products

Process route

nitrobenzene
98-95-3,26969-40-4

nitrobenzene

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With formic acid; palladium on activated charcoal; In methanol; for 70h; Ambient temperature;
34 % Chromat.
12 % Chromat.
53 % Chromat.
aniline
62-53-3

aniline

cyclohexanol
108-93-0

cyclohexanol

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With ammonia; palladium on activated charcoal; at 250 ℃; for 3h; Product distribution;
32 % Chromat.
3.2 % Chromat.
1.4 % Chromat.
aniline
62-53-3

aniline

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
aluminum oxide; ruthenium; at 170 ℃; for 2.5h; Product distribution; Mechanism; investigation of the hydrogenation of aniline with various hydrogenation catalysts in the presence and abscence of the fused salts;
80.4%
7%
0.3%
With hydrogen; palladium/alumina; at 240 ℃; for 2.5h; Product distribution; Mechanism; investigation of the hydrogenation of aniline with various hydrogenation catalysts in the presence and abscence of the fused salts;
20%
51.9%
1.1%
With formic acid; palladium on activated charcoal; In methanol; for 70h; Ambient temperature;
49 % Chromat.
31 % Chromat.
20 % Chromat.
Nitrosobenzene
586-96-9

Nitrosobenzene

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

Conditions
Conditions Yield
With formic acid; palladium on activated charcoal; In methanol; for 70h; Ambient temperature;
18 % Chromat.
77 % Chromat.
cyclohexanol
108-93-0

cyclohexanol

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

aniline
62-53-3

aniline

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With ammonia; palladium on activated charcoal; at 250 ℃; for 3h; Product distribution; Effect of catalyst (Ru, Rh, Pt on C), reaction time, temperature, amount of ammonia, composition of reaction mixture.;
68 % Chromat.
41 % Chromat.
6 % Chromat.
1.9 % Chromat.
cyclohexanol
108-93-0

cyclohexanol

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

aniline
62-53-3

aniline

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With ammonia; hydrogen; platinum on silica; at 219.9 ℃; Product distribution; Mechanism; various catalysts, effect of reaction time, temperature;
aniline
62-53-3

aniline

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
With hydrogen; aluminum oxide; carbon monoxide; at 199.85 ℃;
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

aniline
62-53-3

aniline

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

cyclohexanol
108-93-0

cyclohexanol

Conditions
Conditions Yield
With aluminum oxide; hydrogen; copper(II) oxide; zinc(II) oxide; at 200 ℃; under 18751.5 Torr; Product distribution; var. metal oxides composition, var. temp. and pressure;
aniline
62-53-3

aniline

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield
at 220 - 230 ℃; under 87400 - 91200 Torr;
aniline
62-53-3

aniline

N-phenyl-2-cyclohexylamine
1821-36-9

N-phenyl-2-cyclohexylamine

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
Conditions Yield

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