A continuous process for the production of 2,2,6,6-tetramethylpiperidin-4-ol catalyzed by Cu–Cr/γ-Al2O3

Fan, Xiaopeng; Liu, Shuai; Yan, Xilong; Du, Xiaobao; Chen, Ligong

doi:10.1016/j.catcom.2010.04.012

Cited by 10 publications

(6 citation statements)

References 11 publications

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“…While the selectivity decreased from 98 % at 98 8C to 77 % at 152 8C, it increased from 75 % to 92 % with the increase of hydrogen pressure from 10 bar to 40 bar. [77] Jess and co-workers carried out the flow hydrogenation kinetics of the flavor substance b-ionone using Raney-Ni as catalyst and high temperature/pressure conditions (180-230 8C, 50-90 bar). [78] The initial attempts by the Krumrine group to reduce chromenone to chromane using catalytic hydrogenation on a Parr apparatus were only partially successful.…”

Section: Carbonyl Group Hydrogenationmentioning

confidence: 99%

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

2011

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Microreactor technology and continuous flow processing in general are key features in making organic synthesis both more economical and environmentally friendly. Heterogeneous catalytic hydrogenation reactions under continuous flow conditions offer significant benefits compared to batch processes which are related to the unique gas-liquid-solid triphasic reaction conditions present in these transformations. In this review article recent developments in continuous flow heterogeneous catalytic hydrogenation reactions using molecular hydrogen are summarized. Available flow hydrogenation techniques, reactors, commonly used catalysts and examples of synthetic applications with an emphasis on laboratory-scale flow hydrogenation reactions are presented.

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Section: Carbonyl Group Hydrogenationmentioning

confidence: 99%

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

2011

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“…A variety of metals including Pt, Ru, Rh, Ni, and Cu catalyze the hydrogenation of carbonyl groups [23]. Cu [23][24][25][26] and Pt [27][28][29][30] based catalysts have been extensively studied for the hydrogenation of carbonyl groups. For example, Fan et al [23] investigated Cu-γAl 2 O 3 and Ni-γAl 2 O 3 to hydrogenate 2,2,6,6-tetramethylpiperidin-4-one to 2,2,6,6 tetramethylpiperidin-4-ol at 140 • C. The results demonstrated that Cu-γAl 2 O 3 had much better activity and selectivity than Ni-γAl 2 O 3 .…”

Section: Introductionmentioning

confidence: 99%

“…Cu [23][24][25][26] and Pt [27][28][29][30] based catalysts have been extensively studied for the hydrogenation of carbonyl groups. For example, Fan et al [23] investigated Cu-γAl 2 O 3 and Ni-γAl 2 O 3 to hydrogenate 2,2,6,6-tetramethylpiperidin-4-one to 2,2,6,6 tetramethylpiperidin-4-ol at 140 • C. The results demonstrated that Cu-γAl 2 O 3 had much better activity and selectivity than Ni-γAl 2 O 3 . They also studied the effect of introducing Cr into Cu-γAl 2 O 3 and found that Cu-Cr/γAl 2 O 3 displayed better catalytic performance over Cu-γAl 2 O 3 .…”

Section: Introductionmentioning

confidence: 99%

Conversion of 5-Methyl-3-Heptanone to C8 Alkenes and Alkane over Bifunctional Catalysts

Al-Auda

Al-Atabi

et al. 2019

Catalysts

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A one-step catalytic process was used to catalyze the hydrodeoxygenation of 5-methyl-3-heptanone (C8 ketone) to a mixture of 5-methyl-3-heptene, 5-methyl-2-heptene (C8 alkenes), and 3-methyl heptane (C8 alkane). High conversion of C8 ketone to the desired products was achieved over a single bed of a supported catalyst (bifunctional heterogeneous catalyst) consisting of one transition metal (copper (Cu) or platinum (Pt)) loaded on alumina (Al2O3) under mild operating conditions (reaction temperatures were varied between 180 °C to 260 °C, and the pressure was 1 atm). The C8 ketone was hydrogenated to 5-methyl-3-heptanol (C8 alcohol) over metal sites, followed by dehydration of the latter on acid sites on the support to obtain a mixture of C8 alkenes. These C8 alkenes can be further hydrogenated on metal sites to make a C8 alkane. The results showed that the main products over copper loaded on alumina (20 wt% Cu–Al2O3) were a mixture of C8 alkenes and C8 alkane in different amounts depending on the operating conditions (the highest selectivity for C8 alkenes (~82%) was obtained at 220 °C and a H2/C8 ketone molar ratio of 2). However, over platinum supported on alumina (1 wt% Pt–Al2O3), the major product was a C8 alkane with a selectivity up to 97% and a conversion of 99.9% at different temperatures and all H2/C8 ketone ratios.

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“…2,2,6,6-Tetramethyl-4-piperidinol (TMP, CAS No. : 2403-88-5, Figure ) is an important reaction intermediate in organic synthesis and is commonly used to produce hindered amine light stabilizers, bleaching agents, pharmaceuticals, polymerization inhibitors, and cross-linking agents for epoxy resins. , …”

Section: Introductionmentioning

confidence: 99%

“…: 2403-88-5, Figure 1) is an important reaction intermediate in organic synthesis and is commonly used to produce hindered amine light stabilizers, bleaching agents, pharmaceuticals, polymerization inhibitors, and cross-linking agents for epoxy resins. 1,2 In industrial production, TMP is usually synthesized through the catalytic hydrogenation method, 1 chemical reduction, 3 and electrochemical synthesis; 4 in the end, TMP is crystallized with a high level of purity and appropriate crystal-size distribution (CSD). The crystal structure of TMP has been determined by She et al 5 The crystal size and the crystal size distribution (CSD) are critical parameters that determine the quality of a crystal product, 6,7 influencing the flowability and the dissolution rate in downstream, and so forth.…”

mentioning

confidence: 99%

Solubility and Crystallization Process of 2,2,6,6-Tetramethyl-4-piperidinol (TMP)

Su¹,

Sun

Lu³

et al. 2017

Org. Process Res. Dev.

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2,2,6,6-Tetramethyl-4-piperidinol (TMP) crystal is a very important intermediate in organic synthesis. To obtain an improved crystallization yield and desirable crystal-size characteristics, several commonly used organic solvents were investigated to determine the solubility of TMP using a gravimetric method. An ethanol solvent and a cooling crystallization method were chosen to obtain an improved theroretical yield. The cooling crystallization process of TMP in the ethanol solution was further optimized to crystallize larger crystals with a narrow crystal-size distribution using an orthogonal array design. Final TMP crystals with an average diameter of 1110 μm and a diameter span of 0.715 were obtained under laboratory conditions using the optimized process.

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A continuous process for the production of 2,2,6,6-tetramethylpiperidin-4-ol catalyzed by Cu–Cr/γ-Al2O3

Cited by 10 publications

References 11 publications

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Heterogeneous Catalytic Hydrogenation Reactions in Continuous‐Flow Reactors

Conversion of 5-Methyl-3-Heptanone to C8 Alkenes and Alkane over Bifunctional Catalysts

Solubility and Crystallization Process of 2,2,6,6-Tetramethyl-4-piperidinol (TMP)

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