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13323-81-4

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13323-81-4 Usage

Chemical Properties

Colorless liquid

Occurrence

Has apparently not been reported to occur in nature.

Preparation

By hydrogenation or reduction of acetophenone; or from methyl magnesium chloride plus benzaldehyde by a Grignard-type reaction (Bedoukian, 1967).

Metabolism

Styrallyl alcohol is converted in rabbits into hippuric acid and methylphenylcarbinyl glucuronide, both optical forms of the carbinol behaving similarly. A small proportion (1-2%) is excreted as mandelic acid (Wjlliams, 1959).

Purification Methods

Purify the alcohol via its hydrogen phthalate. [See Houssa & Kenyon J Chem Soc 2260 1930.] Shake it with a solution of ferrous sulfate, and th

Check Digit Verification of cas no

The CAS Registry Mumber 13323-81-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,3,2 and 3 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13323-81:
(7*1)+(6*3)+(5*3)+(4*2)+(3*3)+(2*8)+(1*1)=74
74 % 10 = 4
So 13323-81-4 is a valid CAS Registry Number.

13323-81-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name α-METHYLBENZYL ALCOHOL

1.2 Other means of identification

Product number -
Other names sec-phenethyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13323-81-4 SDS

13323-81-4Relevant articles and documents

Direct reductive amination versus hydrogenation of intermediates - A comparison

Tararov, Vitali I.,Kadyrov, Renat,Riermeier, Thomas H.,Fischer, Christine,Boerner, Armin

, p. 561 - 565 (2004)

The direct reductive amination of acetophenone with benzylamine or piperidine was studied in comparison with the hydrogenation of possible intermediates like a corresponding imine or enamine. No common features in terms of productivity and stereo-control (in the case of chiral catalysts) have been found for both processes. Hence evaluation of efficient, selective and enantioselective catalysts for direct reductive animation appears to be a separate task.

Reaction of 1,3-dihalopropene with trialkylmanganate

Kakiya, Hirotada,Inoue, Rie,Shinokubo, Hiroshi,Oshima, Koichiro

, p. 73 - 74 (1998)

A three-component coupling reaction was performed. Treatment of 1,3-dibromopropene or 1,3-dichloropropene with tributylmanganate (n-Bu3MnLi) provided a butylated allylmanganese compound which could be trapped by an electrophile such as benzalde

Model compound studies of the beta-O-4 linkage in lignin: absolute rate expressions for beta-scission of phenoxyl radical from 1-phenyl-2-phenoxyethanol-1-yl radical.

Kandanarachchi, Pramod H,Autrey, Tom,Franz, James A

, p. 7937 - 7945 (2002)

Arrhenius rate expressions were determined for beta-scission of phenoxyl radical from 1-phenyl-2-phenoxyethanol-1-yl, PhC*(OH)CH2OPh (V). Ketyl radical V was competitively trapped by thiophenol to yield PhCH(OH)CH2OPh in competition with beta-scission to yield phenoxyl radical and acetophenone. A basis rate expression for hydrogen atom abstraction by sec-phenethyl alcohol, PhC*(OH)CH3, from thiophenol, log(k(abs)/M(-1) s(-1)) = (8.88 +/- 0.24) - (6.07 +/- 0.34)/theta, theta = 2.303RT, was determined by competing hydrogen atom abstraction with radical self-termination. Self-termination rates for PhC*(OH)CH3 were calculated using the Smoluchowski equation employing experimental diffusion coefficients of the parent alcohol, PhCH(OH)CH3, as a model for the radical. The hydrogen abstraction basis reaction was employed to determine the activation barrier for the beta-scission of phenoxyl from 1-phenyl-2-phenoxyethanol-1-yl (V): log(k beta)/s(-1)) = (12.85 +/- 0.22) - (15.06 +/- 0.38)/theta, k beta (298 K) ca. (64.0 s(-1) in benzene), and log(k beta /s(-1)) = (12.50 +/- 0.18) - (14.46 +/- 0.30)/theta, k beta (298 K) = 78.7 s(-1) in benzene containing 0.8 M 2-propanol. B3LYP/cc-PVTZ electronic structure calculations predict that intramolecular hydrogen bonding between the alpha-OH and the -OPh leaving group of ketyl radical (V) stabilizes both ground- and transition-state structures. The computed activation barrier, 14.9 kcal/mol, is in good agreement with the experimental activation barrier.

Study of the efficiency of amino-functionalized ruthenium and ruthenacycle complexes as racemization catalysts in the dynamic kinetic resolution of 1-phenylethanol

Eckert,Brethon,Li,Sheldon,Arends

, p. 2603 - 2609 (2007)

The ruthenium-amino structural motif in ruthenacycles and aminomethylpyridine ruthenium complexes turned out to be a useful basis for the design of readily accessible and active catalysts for the racemization of alcohols. Inspired by the proven ligand acceleration of 2-aminomethylpyridine (ampy) ligands in ruthenium-catalyzed hydrogen transfer, the readily accessible ampy-based oxazolines 8a and 8b were tested and led to novel and active ruthenium racemization catalysts. The highly active ortho-metalated-ampy Ru complex 7 was demonstrated to be a fast racemization catalyst (100% racemization of 1-phenylethanol at 70°C within 10 min). When used in the dynamic kinetic resolution of 1-phenylethanol towards 1-phenylethyl acetate, the cycloruthenated amine 5 was most active, leading to 86% of the (R)-1-phenylethylacetate with > 99% ee.

Selective reduction of aromatic ketones in aqueous medium mediated by Ti(III)/Mn: A revised mechanism

Rosales, Antonio,Mu?oz-Bascón, Juan,Roldan-Molina, Esther,Casta?eda, Mayra A.,Padial, Natalia M.,Gans?uer, Andreas,Rodríguez-García, Ignacio,Oltra, J. Enrique

, p. 7672 - 7676 (2014)

An experimental study on the role played by each of the reagents involved in the selective reduction of aromatic ketones in aqueous medium is reported. In this reaction, the reduction of aromatic ketones is mediated by Cp 2TiCl. Moreover, the presence of Mn in the reaction medium is mandatory. To account for these findings, a substantially revised mechanism is proposed.

Tunneling in C-H oxidation reactions by an oxoiron(IV) porphyrin radical cation: Direct measurements of very large H/D kinetic isotope effects

Pan, Zhengzheng,Horner, John H.,Newcomb, Martin

, p. 7776 - 7777 (2008)

Rate constants for oxidations of benzyl alcohol-d0 and -d7 by oxoiron(IV) tetramesitylporphyrin radical cation perchlorate in acetonitrile were measured in single turnover kinetic studies. The kinetic isotope effect (kH/k

Aerobic oxidation of ethylbenzene co-catalyzed by n-hydroxyphthalimide and oxobis(8-Quinolinolato) vanadium (IV) complexes

Qin, Jinwei,Fu, Zaihui,Liu, Yachun,He, Xiangling,Zhang, Dexi,Wu, Wenfeng,Wang, Yanlong,Gong, Xinglang,Deng, Xiaolin,Wu, Haitao,Zou, Yanhong,Yu, Ningya,Yin, Dulin

, p. 1342 - 1348 (2011)

The mediation effect of vanadium compounds on the N-hydroxyphthalimide (NHPI)-catalyzed aerobic oxidation of ethylbenzene (EB) was investigated at 90 °C in benzonitrile. Among the vanadium mediators examined, a series of oxobis(8-quinolinolato) vanadium (

Allylmagnesium Halides Do Not React Chemoselectively because Reaction Rates Approach the Diffusion Limit

Read, Jacquelyne A.,Woerpel

, p. 2300 - 2305 (2017)

Competition experiments demonstrate that additions of allylmagnesium halides to carbonyl compounds, unlike additions of other organomagnesium reagents, occur at rates approaching the diffusion rate limit. Whereas alkylmagnesium and alkyllithium reagents could differentiate between electronically or sterically different carbonyl compounds, allylmagnesium reagents reacted with most carbonyl compounds at similar rates. Even additions to esters occurred at rates competitive with additions to aldehydes. Only in the case of particularly sterically hindered substrates, such as those bearing tertiary alkyl groups, were additions slower.

Rapid transfer hydrogenation of acetophenone using ruthenium catalysts bearing commercially available and readily accessible nitrogen and phosphorous donor ligands

Braden, Drew J.,Cariou, Renan,Shabaker, John W.,Taylor, Russell A.

, p. 367 - 375 (2019)

The screening, synthesis and testing of Ru complexes generated from commercially available ligands or ligands that can be synthesised in one step, is described. The catalysts were tested for activity in the transfer hydrogenation of acetophenone by isopropanol, a probe reaction for hydrogen transfer processes between oxygenated species, often found in applications such as biomass upgrading and fine and specialty chemical synthesis. Ligand screening was conducted by in situ catalyst generation and examined NPN and NNN pincer type ligands bearing N–H or C[dbnd]N functional groups. The most active transfer hydrogenation catalysts were found to be those bearing N–H functionality, either as amino groups or as benzimidazole groups. Well-defined catalyst precursors were subsequently synthesised, including the novel complex [Ru(1)PPh3(Cl)2] (where (1) = bis(3-aminopropyl)phenylphosphine), the first reported Ru complex for this NPN ligand. Established (PN)2 and PP/NN ketone hydrogenation catalysts were also screened for transfer hydrogen capability, of which [Ru(PhPN)2Cl2] (where PhPN = 2-(diphenylphosphino)ethylamine) was the most active. Subsequently, [Ru(1)PPh3(Cl)2], [Ru(PhPN)2Cl2] and [Ru(4)(PPh3)2Cl][Cl] (where (4) = 2,6-bis(2-benzimidazolyl)pyridine) were investigated more closely to compare rate constants (determined by reaction profile regression analysis) as a more accurate measure of catalyst activity over commonly reported turn over frequencies (TOF). The effect of the reaction products on the catalyst activity was evaluated using feed spiking experiments. Catalyst deactivation was shown to be prevalent and subsequently incorporated into a simple kinetic model which enabled more accurate reaction profile fitting and provided rate constants for both the transfer hydrogenation step and deactivation reaction.

Catalytic racemization of secondary alcohols with new (arene)Ru(II)-NHC and (arene)Ru(II)-NHC-tertiary phosphine complexes

Marozsán, Natália,Horváth, Henrietta,Kováts, éva,Udvardy, Antal,Erdei, Anikó,Purgel, Mihály,Joó, Ferenc

, p. 248 - 256 (2018)

Five new complexes of the type [RuCl2(NHC)(η6-arene)] (4, 5, and 6) and [RuCl(NHC)(η6-arene)(PR3)]Cl (7 and 8) (NHC[dbnd]N-heterocyclic carbene = bmim, emim; arene = benzene, p-cymene; PR3 = PPh3 or pta = 1,3,5-triaza-7-phosphaadamantane) were synthetized and applied as catalysts (together with the known [RuCl2(bmim)(η6-p-cymene)] (3) with and without added PPh3) in racemization of optically active secondary alcohols in toluene. The highest catalytic activity, TOF = 9.3 h?1 (ee as low as 1.3% in 4 h at 95 °C) was observed in racemization of (S)-1-phenylethanol with a catalyst (4 mol%) prepared in situ from 3 and 1 equivalent of PPh3. It is of practical significance that formation of acetophenone byproduct was suppressed to 3.5% by 17% v/v isopropanol in toluene. DFT calculations revealed that the rate determining step in the suggested reaction mechanism was the agostic coordination of hydrogen on the chiral carbon atom of the alcohol substrate.

Understanding the roles of variable Pd(II)/Pd(0) ratio supported on conjugated poly-azobenzene network: From characteristic alteration in properties to their cooperation towards visible-light-induced selective hydrogenation

Nath, Ipsita,Chakraborty, Jeet,Zhang, Gaoke,Chen, Cheng,Chaemchuen, Somboon,Park, Jihae,Zhuiykov, Serge,Han, Taejun,Verpoort, Francis

, p. 120 - 128 (2020)

Selective hydrogenation of organic functionalities at environmentally benign conditions using visible light is of great industrial and economic significance. Herein we report visible-light-induced rapid, almost quantitative and selective hydrogenation of olefins to respective mono-reduced products using cooperative performance of Pd(0) nanoparticles (NPs) and Pd(II) ions evenly distributed on a newly synthesized conjugated mesoporous poly-azobenzene network. Role of variable Pd(0)/Pd(II) ratio on the properties of polymeric networks and their overall catalytic abilities is critically investigated. This is the first proposed example of cooperative hydrogenation by simultaneous activation of H2 and unsaturated substrates using Mott-Schottky heterojunction between Pd NPs and the semiconducting polymer, with the help of Pd(II)-site-mediated η-coordination. A control over selective mono-reduction of diene with identical double bonds was also obtained. The catalytic activity retained for other non-olefinic functionalities as well.

Tandem Suzuki-Miyaura/transfer hydrogenation reaction catalyzed by a Pd-Ru complex bearing an anionic dicarbene

Bitzer, Mario J.,Kühn, Fritz E.,Baratta, Walter

, p. 222 - 226 (2016)

A hetero-bimetallic Pd-Ru N-Heterocyclic Dicarbene (NHDC) complex was synthesized from a Ag-Ru complex by transmetalation. The Pd-Ru system displays high catalytic activity in tandem Suzuki-Miyaura cross-coupling/transfer hydrogenation reaction of bromoaryl ketones with boronic acids in toluene and 2-propanol in the presence of KOH.

Generation of Versatile Reagents Derived from R2Zn and a Vanadium(III) or a Vanadium(IV) Complex and Their Application to Organic Synthesis

Kataoka, Yasutaka,Makihira, Isamu,Utsunomiya, Masaru,Tani, Kazuhide

, p. 8540 - 8543 (1997)

-

Optimization of the transfer hydrogenation reaction of acetophenone on Ni@MOF-5 nanoparticles using response surface methodology

Nemati Chelavi, Azadeh,Zare-Shahabadi, Vahid,Sayyahi, Soheil,Anaraki-Ardakani, Hossein

, p. 445 - 458 (2020)

In this study, the transfer hydrogenation reduction of acetophenone using supported nickel on MOF as catalyst was investigated. BBD and RSM were employed to investigate the effect of the experimental parameters such as Ni content, catalyst content, temper

Garst et al.

, p. 7707 (1972)

Iffland,Davis

, p. 4150 (1977)

Mechanistic Insight into Additions of Allylic Grignard Reagents to Carbonyl Compounds

Bartolo, Nicole D.,Woerpel

, p. 10197 - 10206 (2018)

Allylic Grignard reagents exhibit high reactivity and low selectivity in additions to carbonyl compounds. Additions of allylic Grignard reagents to carbonyl compounds were investigated using prenylmagnesium chloride as a mechanistic probe. When the carbonyl group is relatively unhindered, the addition proceeds through a six-membered transition state with allylic transposition. This process generally occurs with no diastereoselectivity because the reaction rates approach the diffusion limit. With hindered ketones, however, this pathway is disfavored, and the addition proceeds through a transition state resembling that of other Grignard reagents.

Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Br?nsted Acid

Ahmed, Waqar,Zhang, Sheng,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming

, p. 2495 - 2499 (2019)

The cooperative catalysis of copper, silver, and Br?nsted acid is presented as a new strategy for olefin functionalization. The catalytic direct carbohydroxylation of arylalkenes with allylic alcohols provided a straightforward and efficient approach for preparing 4,5-unsaturated alcohols. Synthetically useful functional groups, such as Cl, Br, carbonyl, and chloromethyl, remained intact during the functionalization reaction.

Syntheses, characterization and study of the use of cobalt (II) Schiff-Base complexes as catalysts for the oxidation of styrene by molecular oxygen

Khandar, Ali Akbar,Nejati, Kamellia,Rezvani, Zolfaghar

, p. 302 - 311 (2005)

Schiff-Base complexes of bis-5-phenylazosalicylaldehyde ethylenediimine and bis-5-phenylazosalicylaldehyde-O-phenylenediimine ligands with Co(II) (I and II) have been synthesized and characterized by their IR spectra and elemental analyses. These complexes catalyze the oxidation of styrene in the presence of dioxygen and excess pyridine. The effect of the reaction conditions on the oxidation of styrene was studied by varying solvent, nature and amount of the catalyst and substrate. The catalytic behavior of the studied complexes was shown to be dependent on the conditions applied. In all reactions, acetophenone and 1- phenylethanol were the only observed products.

Ruthenium-catalysed asymmetric transfer hydrogenation of N-(tert-butanesulfinyl)imines

Guijarro, David,Pablo, óscar,Yus, Miguel

, p. 5386 - 5388 (2009)

The ruthenium complex prepared from [RuCl2(p-cymene)]2 and (1S,2R)-1-amino-2-indanol is a very efficient catalyst for the asymmetric transfer hydrogenation of (R)-N-(tert-butanesulfinyl)ketimines in isopropanol. By carefully removing

Immobilisation of the BINAP ligand on dendrimers and hyper-branched polymers: Dependence of the catalytic properties on the linker unit

Kassube, Jutta K.,Wadepohl, Hubert,Gade, Lutz H.

, p. 607 - 616 (2009)

A series of immobilised Carbo-BINAP ligands has been synthesised using poly(propylene imine) (PPI) dendrimers as soluble supports. They contain up to 64 BINAP ligands at their periphery without an additional linking unit. Despite the high steric requirements of the ligand, all dendrimers could be completely functionalised, resulting in the immobilised systems in good yields. Furthermore, the immobilisation strategy that worked out for the fixation of AMINAP ligands with additional linking units as well as of Carbo-BINAP ligands without additional linking units on dendrimers has thus been extended to less regularly hyperbranched poly (ethylene imines) (PEI) as soluble supports. In that way it has been possible to attach on average 9, 26, and 138 Glutaroyl-AMINAP or Carbo-BINAP ligands to PEIs of different molecular weights. The catalytic properties of these systems in the copper-catalysed hydrosilylation of acetophenone were investigated. The dendritic PPI-bound Carbo-BINAP ligands displayed a strong dependence of enantioselectivity and activity on the generation of the dendrimer. For the Carbo-BINAP and Glutaroyl-AMINAP ligands immobilised on the hyperbranched polymers, however, activities and enantioselectivities comparable to those of the mononuclear catalysts were found. The macromolecular, immobilised BINAP ligands could be recycled several times without any observable loss of activity or enantioselectivity.

Hydroxylation of simple alkanes by iodosylbenzene is catalyzed more efficiently by second than by third generation iron(III) porphyrins

Gross, Zeev,Simkhovich, Liliya

, p. 8171 - 8174 (1998)

The catalytic activities of aryl-chlorinated iron tetraarylporphyrins with and without chloro substituents at the β-pyrrole positions- third and second generation catalysts, respectively- were compared for the hydroxylation of ethylbenzene and cyclohexane

Electrochemical reduction of aromatic ketones in 1-butyl-3-methylimidazolium-based ionic liquids in the presence of carbon dioxide: the influence of the ketone substituent and the ionic liquid anion on bulk electrolysis product distribution

Zhao, Shu-Feng,Horne, Mike,Bond, Alan M.,Zhang, Jie

, p. 19247 - 19254 (2015)

Electrochemical reduction of aromatic ketones, including acetophenone, benzophenone and 4-phenylbenzophenone, has been undertaken in 1-butyl-3-methylimidazolium-based ionic liquids containing tetrafluoroborate ([BF4]-), trifluoromethanesulfonate ([TfO]-) and tris(pentafluoroethyl)trifluorophosphate ([FAP]-) anions in the presence of carbon dioxide in order to investigate the ketone substituent effect and the influence of the acidic proton on the imidazolium cation (C2-H) on bulk electrolysis product distribution. For acetophenone, the minor products were dimers (50%) derived from proton coupled electron transfer reactions involving the electrogenerated radical anions and C2-H. In the cases of both acetophenone and benzophenone, the product distribution is essentially independent of the ionic liquid anion. By contrast, 4-phenylbenzophenone shows a product distribution that is dependent on the ionic liquid anion. Higher yields of carboxylic acids (~40%) are obtained with [TfO]- and [FAP]- anions because in these ionic liquids the C2-H is less acidic, making the formation of alcohol less favourable. In comparison with benzophenone, a higher yield of carboxylic acid (>30% versus ~15%) was obtained with 4-phenylbenzophenone in all ionic liquids due to the weaker basicity of 4-phenylbenzophenone radical anion.

-

Kurkov et al.

, p. 4743 (1968)

-

Zakharhin,Agakhanova

, (1977)

A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen

Anwar, Muhammad,Beller, Matthias,Dastgir, Sarim,Junge, Kathrin,Leonard, David K.,Ryabchuk, Pavel

, (2022/02/03)

Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).

Bioinspired Heterobimetallic Photocatalyst (RuIIchrom-FeIIIcat) for Visible-Light-Driven C-H Oxidation of Organic Substrates via Dioxygen Activation

Goswami, Tapas,Kumar, Arun,Kumar, Sushil,Le Poul, Nicolas,Nautiyal, Divyanshu,Singh, Siddhant,Thetiot, Franck

supporting information, p. 16059 - 16064 (2021/11/13)

We report a bioinspired heterobimetallic photocatalyst RuIIchrom-FeIIIcat and its relevant applications toward visible-light-driven C-H bond oxidation of a series of hydrocarbons using O2 as the O-atom source. The RuII center absorbs visible light near 460 nm and triggers a cascade of electrons to FeIII to afford a catalytically active high-valent FeIV═O species. The in situ formed FeIV═O has been employed for several high-impact oxidation reactions in the presence of triethanolamine (TEOA) as the sacrificial electron donor.

RhNPs supported onN-functionalized mesoporous silica: effect on catalyst stabilization and catalytic activity

Pulido-Díaz, Israel T.,Serrano-Maldonado, Alejandro,López-Suárez, Carlos César,Méndez-Ocampo, Pedro A.,Portales-Martínez, Benjamín,Gutiérrez-Alejandre, Aída,Salas-Martin, Karla P.,Guerrero-Ríos, Itzel

, p. 3289 - 3298 (2021/03/16)

Amine and nicotinamide groups grafted on ordered mesoporous silica (OMS) were investigated as stabilizers for RhNPs used as catalysts in the hydrogenation of several substrates, including carbonyl and aryl groups. Supported RhNPs on functionalized OMS were prepared by controlled decomposition of an organometallic precursor of rhodium under dihydrogen pressure. The resulting materials were characterized thoroughly by spectroscopic and physical techniques (FTIR, TGA, BET, SEM, TEM, EDX, XPS) to confirm the formation of spherical rhodium nanoparticles with a narrow size distribution supported on the silica surface. The use of nicotinamide functionalized OMS as a support afforded small RhNPs (2.3 ± 0.3 nm), and their size and shape were maintained after the catalyzed acetophenone hydrogenation. In contrast, amine-functionalized OMS formed RhNP aggregates after the catalytic reaction. The supported RhNPs could selectively reduce alkenyl, carbonyl, aryl and heteroaryl groups and were active in the reductive amination of phenol and morpholine, using a low concentration of the precious metal (0.07-0.18 mol%).

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