Liquid‐Phase Catalytic Hydrogenation of p‐Chlorobenzophenone to p‐Chlorobenzhydrol over a 5 % Pd/C Catalyst

The kinetics of the liquid‐phase catalytic hydrogenation of p‐chlorobenzophenone have been investigated over a 5 % Pd/C catalyst. The effects of hydrogen partial pressure (800–2200 kPa), catalyst loading (0.4–1.6 gm dm^–3), p‐chlorobenzophenone concentration (0.37–1.5 mol dm^–3), and temperature (303–313 K) were studied. A stirring speed > 20 rps has no effect on the initial rate of reaction. Effects of various catalysts (Pd/C, Pd/BaSO₄, Pd/CaCO₃, Pt/C, Raney nickel) and solvents (2‐propanol, methanol, dimethylformamide, toluene, xylene, hexane) on the hydrogenation of p‐chlorobenzophenone were also investigated. The reaction was found to be first order with respect to hydrogen partial pressure and catalyst loading, and zero order with respect to p‐chlorobenzophenone concentration. Several Langmuir‐Hinshelwood type models were considered and the experimental data fitted to a model involving reaction between adsorbed p‐chlorobenzophenone and hydrogen in the liquid phase.     

Hydrogenation of m‐dinitrobenzene to m‐phenylenediamine over La2O3‐promoted Ni/SiO2 catalysts

BACKGROUND: Liquid‐phase catalytic hydrogenation of m‐dinitrobenzene is an environmentally friendly routine for m‐phenylenediamine production. The key to increasing product yield is to develop catalysts with high catalytic performance. In this work, La₂O₃‐modified Ni/SiO₂ catalysts were prepared and applied to the hydrogenation of m‐dinitrobenzene to m‐phenylenediamine. The effect of La₂O₃ loading on the properties of Ni/SiO₂ was investigated. The reaction kinetic study was performed in ethanol over Ni/3%La₂O₃–SiO₂ catalyst, in order to clarify the reaction mechanism of m‐dinitrobenzene hydrogenation. RESULTS: It was found that the activity of the silica supported nickel catalysts is obviously influenced by La₂O₃ loading. Ni/3%La₂O₃–SiO₂ catalyst exhibits high activity owing to its well dispersed nickel species, with conversion of m‐dinitrobenzene and yield of m‐phenylenediamine up to 97.1% and 94%, respectively. The results also show that Ni/3%La₂O₃–SiO₂ catalyst can be reused at least six times without significant loss of activity. CONCLUSION: La₂O₃ shows strong promotion of the effect of Ni/SiO₂ catalyst for liquid‐phase hydrogenation of m‐dinitrobenzene. La₂O₃ loading can affect the properties of Ni/SiO₂ catalyst. Based on the study of m‐dinitrobenzene hydrogenation kinetics over Ni/3%La₂O₃–SiO₂ catalyst, a possible reaction mechanism is proposed. Copyright © 2009 Society of Chemical Industry     

Kinetics of hydrogenation of 4‐chloro‐2‐nitrophenol catalyzed by Pt/carbon catalyst

Hydrogenation of 4‐chloro‐2‐nitrophenol (CNP) was carried out at moderate hydrogen pressures, 7–28 atm, and temperatures in the range 298–313 K using Pt/carbon and Pd/γ‐Al₂O₃ as catalysts in a stirred pressure reactor. Hydrogenation of CNP under the above conditions gave 4‐chloro‐2‐aminophenol (CAP). Dechlorination to form 2‐aminophenol and 2‐nitrophenol is observed when hydrogenation of CNP is carried out above 338 K, particularly with Pd/γ‐Al₂O₃ catalyst. Among the catalysts tested, 1%Pt/C was found to be an effective catalyst for the hydrogenation of CNP to form CAP, exclusively. To confirm the absence of gas–liquid mass transfer effects on the reaction, the effect of stirring speed (200–1000 rpm) and catalyst loading (0.02–0.16 g) on the initial reaction rate at maximum temperature 310 K and substrate concentration (0.25 mole) were thoroughly studied. The kinetics of hydrogenation of CNP carried out using 1%Pt/C indicated that the initial rates of hydrogenation had first order dependence with respect to substrate, catalyst and hydrogen pressure in the range of concentrations varied. From the Arrhenius plot of ln rate vs 1000/T, an apparent activation energy of 22 kJ mol^?1 was estimated. © 2001 Society of Chemical Industry     

Hydrogenation of cis‐1,4‐polyisoprene catalyzed by Ru(CHCH(Ph))Cl(CO)(PCy3)2

Hydrogenation is a useful method which has been used to improve oxidative and thermal degradation resistance of diene‐based polymers. The quantitative hydrogenation of cis‐1,4‐polyisoprene which leads to an alternating ethylene–propylene copolymer was studied in the present investigation. To examine the influence of key factors on the reaction, such as catalyst concentration, polymer concentration, hydrogen pressure, and temperature, a detailed study of the hydrogenation of cis‐1,4‐polyisoprene catalyzed by the Ru complex, Ru(CH?CH(Ph))Cl(CO)(PCy₃)₂ was carried out by monitoring the amount of hydrogen consumed. Infrared and ¹H‐NMR spectroscopic measurements confirmed the final degree of hydrogenation. The hydrogenation of cis‐1,4‐polyisoprene followed pseudo‐first‐order kinetics in double‐bond concentration up to high conversions of double bond, under all sets of conditions studied. The kinetic results suggested a first‐order behavior with respect to total catalyst concentration as well as with respect to hydrogen pressure. The apparent activation energy for the hydrogenation process, obtained from an Arrhenius plot, was 51.1 kJ mol^?1 over the temperature range of 130 to 180°C. Mechanistic aspects of the catalytic process are discussed. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 91: 3259–3273, 2004     

Oxidative degradation of 4‐nitrophenol in UV‐illuminated titania suspension

An internally‐irradiated annular photoreactor has been used to investigate the oxidative degradation of aqueous 4‐nitrophenol with titania as the photocatalyst. Reaction runs were performed over a 3‐h period and in practically all cases, complete degradation was possible within about 2 h. The kinetics was determined as a function of nitrophenol concentration, oxygen partial pressure, catalyst loading, pH, temperature and light intensity. The reaction was characterised by a relatively low activation energy of 7.83 kJ mol^?1 although transport intrusions were negligible. Rate decreased almost exponentially with pH while a quadratic (maximum) behaviour with respect to both oxygen pressure and nitrophenol concentration is symptomatic of self‐inhibition possibly due to the formation of intermediates which competitively adsorb on similar sites to the reactants. Increased catalyst dosage also improved the reaction rate although the possible effects of light scattering and solution opacity caused a drop at loadings higher than about 1.20 g dm^?3. Rate, however, has a linear dependency on light intensity, suggesting that hole–electron recombination processes were negligible at the conditions investigated. © 2001 Society of Chemical Industry     

The hydrogenation of HO-terminated telechelic polybutadienes in the presence of a homogeneous hydrogenation catalyst based on tris(triphenylphosphine)rhodium chloride

The hydrogenation kinetics of multiple bonds in HO-terminated telechelic polybutadienes was investigated using two types of these prepolymers prepared by the anionic and radical polymerization. The rate of addition of hydrogen to the π-bonds of these polydienes in the presence of tris(triphenylphosphine) rhodium chloride as a homogeneous hydrogenation catalyst was determined by the chemical structures of the starting polydienes, their concentration in the solvent, the partial hydrogen pressure, the concentration of the catalyst, and the temperature. The effect of kinetic parameters given above on the rate of hydrogenation reaction can be interpreted in the sense of Wilkinson's reaction mechanism of the hydrogenation of alkenes in the presence of the Rh(I)-complex. Due to the predominant 1,2-structural units, the anionic prepolymer reacted twice as quickly with hydrogen (k = 0.093 mol^?1 dm³ s^?1) compared with the radical prepolymer (k = 0.045 mol^?1 dm³ s^?1). During the hydrogenation of multiple bonds there is a partial loss of hydroxy groups in modified telechelic prepolymers; the extent of this reaction depends on reaction conditions of the hydrogenation reaction.     

Kinetic study of the partial hydrogenation of 1‐heptyne on tungsten oxide supported on alumina

BACKGROUND: Partial hydrogenation of alkynes have industrial and academic relevance on a large scale; industries such as petrochemical, pharmacology and agrochemical use these compounds as raw material. Typical commercial catalysts contains palladium. Finding an economic, active and selective catalyst for the production of alkenes via partial hydrogenation of alkynes is thus an important challenge. On the other hand, the literature on kinetic studies of partial hydrogenation of heavy alkynes is scarce. So the main objectives of this work were to prepare a cheaper catalyst based on low W loading, and study the kinetic of the partial hydrogenation of 1‐heptyne. A pseudo‐homogeneous and six heterogeneous kinetic models were analyzed. The catalyst was characterized by ICP, XPS, DRX, TPR and hydrogen chemisorption techniques. RESULTS: The characterization results indicate that only WO_x species are present on the alumina surface. The WO_x/Al₂O₃ catalyst was active and selective for producing 1‐heptene even at low reaction temperatures, the partial hydrogenation of 1‐heptyne proceeds via two irreversible reactions in parallel. CONCLUSION: The best fit of the experimental data was achieved with a heterogeneous Langmuir‐Hinshelwood‐Hougen‐Watson model in which the rate controlling step is the dissociative adsorption of hydrogen. The activation energy was estimated as E_H2 = 34.8 kJ mol^?1. Copyright © 2012 Society of Chemical Industry     

Synthesis of ZSM‐5 by hydrothermal method with pre‐mixing in a stirred‐tank reactor

This work proposed a synthesis route of ZSM‐5 via the hydrothermal method with premixing in a stirred tank reactor (STR). Effects of various operating conditions, including pre‐mixing time, molar ratio of SiO₂/Al₂O₃, TPAOH (organic template agents) concentration, NaCl (alkali metal cations) concentration, crystallization temperature, and crystallization reaction time, on the average particle size (PS) and particle size distribution (PSD) were investigated. It was found that the pre‐mixing time in the STR significantly affect the formation of proto‐nuclei in premixing process and crystal growth in hydrothermal reaction process, and consequently influence the PS and PSD of the prepared ZSM‐5. ZSM‐5 with good thermal stability, a PS of 380 nm, PSD of 0.17–0.9 µm, pore diameter of 2.31 nm, pore volume of 0.19 cm³ · g^?1 and specific surface area of 337.25 m² · g^?1 were obtained under the optimal conditions of a crystallization reaction time of 24 h, a crystallization temperature of 130 °C, a molar ratio of SiO₂/Al₂O₃ of 200, a TPAOH concentration of 3.5 mol · L^?1, NaCl concentration of 0.3 mol · L^?1, and a pre‐mixing time of 5 h. This work indicated that the operating conditions including premixing time have a significant effect on its PS and PSD.     

Hydrogenation of synthetic cis‐1,4‐polyisoprene and natural rubber catalyzed by [Ir(COD)py(PCy3)]PF6

In the presence of chlorinated solvents, the catalytic complex [Ir(COD)py(PCy₃)]PF₆ (where COD is 1,5‐cyclooctadiene and py is pyridine) was an active catalyst for the hydrogenation of synthetic cis‐1,4‐polyisoprene and natural rubber. Detailed kinetic and mechanistic studies for homogeneous hydrogenation were carried out through the monitoring of the amount of hydrogen consumed during the reaction. The final degree of olefin conversion, measured with a computer‐controlled gas‐uptake apparatus, was confirmed by Fourier transform infrared spectroscopy and ¹H‐NMR spectroscopy. Synthetic cis‐1,4‐polyisoprene was used as a model polymer for natural rubber without impurities to study the influence of the catalyst loading, polymer concentration, hydrogen pressure, and reaction temperature with a statistical design framework. The kinetic results for the hydrogenation of both synthetic cis‐1,4‐polyisoprene and natural rubber indicated that the hydrogenation rate exhibited a first‐order dependence on the catalyst concentration and hydrogen pressure. Because of impurities inside the natural rubber, the hydrogenation of natural rubber showed an inverse behavior dependence on the rubber concentration, whereas the hydrogenation rate of synthetic rubber, that is, cis‐1,4‐polyisoprene, remained constant when the rubber concentration increased. The hydrogenation rate was also dependent on the reaction temperature. The apparent activation energies for the hydrogenation of synthetic cis‐1,4‐polyisoprene and natural rubber were evaluated to be 79.8 and 75.6 kJ/mol, respectively. The mechanistic aspects of these catalytic processes were discussed on the basis of observed kinetic results. The addition of some acids showed an effect on the hydrogenation rate of both rubbers. The thermal properties of hydrogenated rubber samples were determined and indicated that hydrogenation increased the thermal stability of the hydrogenated rubber but did not affect the inherent glass‐transition temperature. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 4219–4233, 2006     

Degradation of C.I. Acid Orange 7 by heterogeneous Fenton oxidation in combination with ultrasonic irradiation

BACKGROUND: A mesoporous alumina supported nanosized Fe₂O₃ was prepared through an original synthesis procedure and used as a heterogeneous catalyst for the Fenton process degradation of the model azo dye C.I. Acid Orange 7 enhanced by ultrasound irradiation (US/Fe₂O₃‐Al₂O₃‐meso/H₂O₂ system). The effect of various operating conditions was investigated, namely hydrogen peroxide concentration, initial pH, ultrasonic power and catalyst loading. RESULTS: The results indicated that the degradation of C.I. Acid Orange 7 followed a pseudo‐first‐order kinetic model. There exists an optimal hydrogen peroxide concentration, initial pH, ultrasonic power and catalyst loading for decolorization. The aggregate size of the spent catalyst was reduced after dispersion in water by ultrasonic irradiation. A very low level of iron leaching was observed ranging from < 0.1 to 0.23 mg L^?1. The intermediate products of C.I. Acid Orange 7 degradation were identified using gas chromatography–mass spectrometry (GC‐MS). CONCLUSION: The optimal conditions for efficient C.I. Acid Orange 7 degradation were pH close to 3, hydrogen peroxide concentration 4 mmol L^?1, catalyst loading 0.3 g L^?1, and ultrasonic power 80 W. Copyright © 2011 Society of Chemical Industry     

Study on liquid‐phase hydrogenation of paranitrotoluene over Ru‐based catalysts

This paper presented a study on the role of yttrium addition to Ru‐based catalysts for liquid phase paranitrotoluene hydrogenation reaction. An impregnation‐precipitation method was used for preparation of a series of yttrium doped Ru/NaY catalysts with yttrium content in the range of 0.0026–0.0052 g/g. Properties of the obtained samples were characterized and analyzed by X‐ray diffraction (XRD), H₂‐TPR, Transmission electron microscopy (TEM), ICP atomic emission spectroscopy, and Nitrogen adsorption‐desorption. The results revealed that catalytic activity of NaY supported Ru catalysts increased with the yttrium content at first, then decreased with the further increase of yttrium content. When yttrium content was 0.0033 g/g, a Ru‐Y/NaY² catalyst showed the most excellent performance of paranitrotoluene hydrogenation reaction (paranitrotoluene conversion and the selectivity toward P‐methyl‐cyclohexylamine reached 99.9 % and 82.5 %, respectively). In addition, to compare with the performance of Ru‐Y/NaY catalysts, the active carbon supported Ru catalysts were prepared using the same method in view of its higher surface area and adsorption capacity. Finally, the effect of solvent on the reaction over Ru‐Y/NaY² catalyst has been investigated, it was found that the best performance of paranitrotoluene hydrogenation reaction took place in protic solvents (isopropanol and ethanol). This was mainly ascribed to their polarity and hydrogen‐bond accepting capability.

     

Effect of Reaction Solvent on the Hydrogenation of Isophthalonitrile for Meta‐Xylylendiamine Preparation

This study focused on the effects of reaction solvent on the hydrogenation of isophthalonitrile (IPN) to produce m‐Xylylenediamine (MXDA) over Ni‐based commercial catalyst. The hydrogenation was carried out using various reaction solvents such as 1‐methylimidazole, mesitylene, benzyl ether and isopropanol under various reaction conditions. It was observed that 1‐methylimiazole outperformed the other reaction solvent, exhibiting a high MXDA yield and producing a low concentration of undesirable products.     

Comparison of a new immobilized Fe3+ catalyst with homogeneous Fe3+–H2O2 system for degradation of 2,4‐dinitrophenol

BACKGROUND: Heterogeneous Fenton catalysts have been used to treat various organic pollutants in an aqueous environment. The present study has investigated the degradation of 2,4‐dinitrophenol (2,4‐DNP), a priority pollutant generated by such industries as pharmaceuticals, pesticides, pigments and dyes. Degradation of 2,4‐DNP (100 mg L^?1) was studied using Fe³⁺ loaded on Al₂O₃ as a heterogeneous catalyst in the presence of H₂O₂, and the efficiency compared with the homogeneous Fe³⁺/H₂O₂ based Fenton‐like process. The effect of different parameters for both processes, such as catalyst loading, H₂O₂ concentration, initial solution pH, initial substrate concentration and temperature were investigated and the optimum operating conditions determined. RESULTS: Under optimal operating conditions of the homogeneous system ([Fe³⁺] 125 mg L^?1; [H₂O₂] 250 mg L^?1; pH 3; room temperature), 92.5% degradation was achieved in 35 min for an initial 2,4‐DNP concentration of 100 mg L^?1. In the case of immobilized Fe (Fe³⁺–Al₂O₃ catalyst), degradation improved to 98.7% under the condition 10 wt% [Fe³⁺–Al₂O₃] 1 g L^?1 catalyst loading; [H₂O₂] 250 mg L^?1; pH 3; at room temperature for the same duration. CONCLUSIONS: This study demonstrated the stability and reusability of the prepared heterogeneous catalyst. This process is a viable technique for treatment of aqueous solutions containing contaminants. Copyright © 2012 Society of Chemical Industry     

Rate equations for the fischer‐tropsch reaction on a promoted iron catalyst

Intrinsic rates for the Fischer‐Tropsch synthesis reaction over a promoted iron catalyst fabricated at the Research Institute of the Petroleum Industry (RIPI) have been obtained in the temperature range of 290°C to 310°C, pressure range of 1500 to 2300 kPa, molar hydrogen to carbon monoxide ratio of 0.76 to 1.82, and a space velocity of 3300 h^?1 under conditions of constant catalyst activity. To this end, the initial reaction rates have been measured at constant temperature (±1°C) in the absence of diffusion limitations, and power‐law equations have been fitted in terms of the hydrogen and carbon monoxide partial pressures for the reaction rates.     

Conjugated linoleic acid formation by hydrogenation/isomerisation of safflower oil over bifunctional structured catalyst Rh/SBA‐15

Directed isomerisation of safflower oil under very low hydrogen partial pressure of 7 psi over a novel bifunctional highly structured rhodium‐based catalyst (Rh/SBA‐15), having narrow pore size distribution ranging from 4 to 8 nm, and BET‐specific surface of ≈1,000 m² g^?1, was investigated as a new chemocatalytic approach for vegetable oil hardening and simultaneously producing health‐beneficial conjugated linoleic acids (CLA). Time course profiles of (cis‐9, trans‐11)‐; (cis‐10, trans‐12)‐; (trans‐10, cis‐12)‐; (cis,cis)‐ and (trans, trans)‐octadecadienoic isomers (CLAs) as well as the other fatty acids traditionally encountered during the hydrogenation of vegetable oils are presented and discussed under selected process conditions. Preliminary results show that it is possible to tailor characteristics of the hydrogenation catalyst in such way to confer its bi‐functional activity: hydrogenation and conjugation isomerisation. © 2011 Canadian Society for Chemical Engineering     

Destruction of chlorinated organics by hydrotreatment using Ru/TiO2 catalyst

Catalytic hydrodechlorination reactions of p‐chloro‐m‐cresol (PCMC) and p‐chloroaniline (PCA) were investigated in a slurry reactor using a Ru/TiO₂ catalyst. The organic reaction intermediates, m‐cresol and aniline, were further converted into methylcyclohexanol and cyclohexylamine respectively. Kinetics of PCMC hydrogenation was studied over the ranges in temperature, 323–373 K, H₂ partial pressure, 0.34–1.38 MPa, PCMC concentration, 3.5–14 mM and catalyst loading, 0.1–2 kg/m³. The reaction orders with respect to PCMC and H₂ were evaluated as 0.5 and 0.8 respectively. It was found that aniline hydrogenation is the rate‐determining step in the hydrotreatment of PCA. Kinetics of aniline hydrogenation was studied at 343 and 363 K over the ranges in H₂ partial pressure, 0.34–1.38 MPa, aniline concentration, 5.4–21.5 mM and catalyst loading, 0.1–0.6 kg/m³. The reaction orders with respect to aniline and H₂ were found to be 1.3 and 1.0 respectively. © 2012 Canadian Society for Chemical Engineering     

Examination of catalytic behavior and origin of the initial transient period for Pt nanoclusters modified with cinchonidine

Nanoclusters prepared by a novel water-free method are compared directly with nanoclusters prepared by the known aqueous preparation as well as conventional Pt/Al₂O₃ for the enantioselective hydrogenation of ethyl pyruvate. The catalytic behavior of cinchonidine on colloidal Pt was investigated during ethyl pyruvate hydrogenation in acetic acid under 10 bar of hydrogen at 22 °C with (1 mmol L⁻¹) and without addition of free cinchonidine. The effect of hydrogen pressure, cinchonidine concentration, ethyl pyruvate and catalyst loading on the enantiomeric excess (EE) with time were also studied. Through these studies, we propose that the nature of the observed initial transient period (ITP) for these “quasi-homogeneous” systems may be explained by desorption of the weakly adsorbed tilted “N lone pair bonded” cinchonidine species from the Pt surface due to interaction with hydrogen.     

m‐Chloroaniline emulsion polymerization,macromolecular chain structure and electrochemical properties

Poly(m‐chloroaniline) (PmClAn) was synthesized by emulsion polymerization. The influences of reaction temperature and initiator concentration on polymerizations were studied. It was found that PmClAn with number‐average molecular weight of 1.85 × 10³ g mol^?1 was obtained by the following conditions: 80 °C, [monomer] = 0.187 × 10^?3 mol l^?1, [sodium lauryl sulfate] = 4.8 × 10^?2 mol l^?1, [potassium peroxydisulfate] = 5.6 × 10^?2 mol l^?1, reaction period = 2.0 h. ¹H NMR, FTIR, and transmission and scanning microscopy were used for structural characterization of PmClAn. It was shown that the ratio of benzoid to quinoid units in the macromolecular chain was respectively 3:2, and that PmClAn has a typical crystalline monoclinic form. A PmClAn molecular chain configuration was also proposed on the basis of crystallographic data. Cyclic voltammetry experiments revealed the PmClAn membrane electrode electroactivity. This electroactivity increased when the polymer was proton‐doped. When Pt particles were electrodeposited onto the polymer membrane electrode, they presented a preferred orientation. Isopropanol oxidation intensities with platinized PmClAn modified electrodes were larger than with a platinized Pt electrode. We also found that oxidation occurred mainly on the Pt particles deposited on the polymer, and that the anodic peak potential changed with polymer and its doping level. These results indicated that the Pt particles interacted with the polymer and that catalytic properties could be observed. © 2002 Society of Chemical Industry     

The interchange reaction between poly(ethylene terephthalate) and poly(m‐xylylene adipamide)

The interchange reaction in blends of poly(ethylene terephthalate) (PET) and poly(m‐xylylene adipamide) (MXD6) has been characterized in terms of changes observed in spectra obtained with a 600‐MHz ¹H‐NMR. The selective degradation of PET components in the blends was carried out in the NMR tubes prior to evaluation. Results indicate that there is no chemical reaction between the PET and MXD6 in the absence of sodium p‐toluenesulfonate catalyst. The presence of the catalyst activates the interchange reaction between these two resins. A mathematical method was applied to calculate the degree of randomness of PET‐MXD6 copolymer. In addition, the reaction degree was found to be affected by exposure temperature, time, shear rate, and catalyst concentration. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Homogeneous catalytic hydrogenation of hydroxyl‐terminated liquid nitrile rubber

It was difficult to obtain high degree of hydrogenation of hydroxyl‐terminated liquid nitrile rubber (HTBN) by using homogeneous noble metal catalyst because the hydroxyl (? OH) in HTBN was likely to cause catalyst poisoning. In this study, with hexamethyl disilylamine protecting ? OH, a good yields of hydrogenated HTBN was synthesized through the use of homogeneous metal catalyst. The effects of catalyst concentration, reaction time, hydrogen pressure, and temperature on the hydrogenation of HTBN were investigated and obtained the following optimum process parameter values: catalyst mass fraction of 0.8%, reaction time of 8 h, pressure of 1.6 MPa, and temperature of 100°C. Fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy were used to characterize the hydrogenation product of the protected HTBN, indicating that under certain conditions a high degree of hydrogenation of HTBN can be achieved. Only the carbon–carbon double bonds (C?C), not the ? CN bonds, are subject to hydrogenation. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012