Influence of alkylation parameters, feedstock composition, and catalyst type on the ortho/para ratio of resulting alkylphenols

Котов, С. В.; Tyshchenko, V. A.; Zerzeva, I. M.; Тарасов, А. В.; Тимофеева, Г. В.; Kotova, N. S.

doi:10.1134/s0965544117020165

Cited by 3 publications

(2 citation statements)

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“…[1][2][3][4][5][6][7][8][9][10]. В последнее время их широко применяют как лиганды к каталитическим прекурсорам для процесса олигомеризации этилена, а также в виде лекарственных препаратов против вредителей и болезней растений в сельском хозяйстве [11][12][13][14][15][16][17][18][19][20].…”

Section: The Yield Of the Target Product The Reaction Temperature Was Varied From 80 To 140 °C The Reaction Time -From 2 To 8 H Molar Ratunclassified

Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines

Rasulov¹,

Aghamaliyev²,

Nagiyeva³

et al. 2021

IVKKT

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The paper deals with the results of cycloalkylation of phenol with 1-methylcyclopentene, 1(3)-methylcyclohexene in the presence of KU-23 catalyst and influence of various parameters on the yield of the target product. The reaction temperature was varied from 80 to 140 °C, the reaction time - from 2 to 8 h, molar ratio of phenol to cyclene – from 1:2 to 2:1 mol/mol, the catalyst amount – from 5 to 15%. Maximum yield of para-[1(3)-methylcycloalkyl] phenols is obtained under the following conditions: temperature – 110-120 °C, duration – 5-6 h, molar ratio of phenol to 1(3)-methylcycloalkene – 1:1 mol/mol and the catalyst amount is 10% based on taken phenol. Simultaneously, the yield of the target products – para-[1(3)-methylcycloalkyl] phenols is 68.6-73.5% per taken phenol, the selectivity is 91.8-94.3% on the target product. As a result of the chromatographic studies of the products of phenol cycloalkylation with 1(3)-methylcycloalkenes in the presence of KU-23 catalyst it becames clear that the alkylate mainly contains paracycloalkyl-substituted phenols (89.6-94.1%). After rectification of the alkylate at low pressure (10 mm Hg), the target products were obtained with a purity of 97.6-98.2% and their physico-chemical properties were determined. The resulting para-[1(3)-methylcycloalkyl] phenols were aminomethylated by formaldehyde and aminoethylnonylimidazoline at the ratio of 1:2:2. As a result, Mannich bases were obtained with yield of 68.3-76.7% from theory. The synthesized methylcycloalkylbenzylaminoethylnonylimidazolines were tested as antioxidants of M-8 engine oil. The oxidation resistance of the oil has been investigated without the addition and with the addition of ИХП-21 antioxidants, known benzylphenylamines and the compounds of the invention. Addition of the obtained compounds to the base oil leads to enhancement of its antioxidant properties, at application of which viscosity increase is 14.07-15.28%, and precipitate - 0.45-0.57%.

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Section: The Yield Of the Target Product The Reaction Temperature Was Varied From 80 To 140 °C The Reaction Time -From 2 To 8 H Molar Ratunclassified

Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines

Rasulov¹,

Aghamaliyev²,

Nagiyeva³

et al. 2021

IVKKT

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“…To effectively implement the chemical reaction processes of both alkylation and dealkylation, it necessitated the introduction of catalysts, while the same catalyst was applicable to both reactions. Among a range of catalysts studied, the commonly used liquid acids such as alkylbenzene sulfonic acid and sulfuric acid have demonstrated high catalytic efficiency 14–17 . However, the addition of a large amount of acid in the homogeneous reaction system has inevitably led to difficulties for catalyst separation and products purification.…”

Section: Introductionmentioning

confidence: 99%

An ecofriendly and reusable solid acid catalyst ZrO₂‐SIEC for highly selective alkylation of 2,4/2,5‐xylenol

Sun

Chen

et al. 2021

Asia-Pacific J Chem Eng

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Monodisperse composite microspheres were prepared of zirconia and urea formaldehyde resin having an average particle size of 2.2 μm. Their surface was modified by silane coupling agent and styrene, and then sulfuric acid assisted with silver sulfate to form solid sulfonic acid based ion‐exchange catalyst (namely, ZrO2‐SIEC) for the alkylation of 2,4/2,5‐xylenol mixture. The selectivities of catalyst ZrO2‐SIEC to produce 6‐2,4‐xylenol and 4‐2,5‐xylenol were found to be 98.9% and 97.9%, with yields of 98.6% and 80.9%, respectively. The optimized reaction conditions were identified including temperature (80°C), catalyst dosage (9%) and reaction time (180 min). In addition, catalyst ZrO2‐SIEC showed good reusability for maintaining stable catalytic performance over 25 cycles of reuse, attributed to its stable mechanical, thermal and chemical properties. Comparison with other four catalysts demonstrated good performance of ZrO2‐SIEC in terms of catalytic activity, operating conditions, separation from products, and environmental friendliness.

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Synthesis and Properties of 2-Hydroxy-3[3(4)-methylcyclohexen-3-yl-isopropyl]-5-arylkylacetophenone

et al. 2023

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Influence of alkylation parameters, feedstock composition, and catalyst type on the ortho/para ratio of resulting alkylphenols

Cited by 3 publications

References 0 publications

Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines

Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines

An ecofriendly and reusable solid acid catalyst ZrO₂‐SIEC for highly selective alkylation of 2,4/2,5‐xylenol

Synthesis and Properties of 2-Hydroxy-3[3(4)-methylcyclohexen-3-yl-isopropyl]-5-arylkylacetophenone

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Influence of alkylation parameters, feedstock composition, and catalyst type on the ortho/para ratio of resulting alkylphenols

Cited by 3 publications

References 0 publications

Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines

Synthesis and Properties of 2-Hydroxy-5[1(3)-Methylcycloalkyl]-Benzylaminoethylnonylimidazolines

An ecofriendly and reusable solid acid catalyst ZrO2‐SIEC for highly selective alkylation of 2,4/2,5‐xylenol

Synthesis and Properties of 2-Hydroxy-3[3(4)-methylcyclohexen-3-yl-isopropyl]-5-arylkylacetophenone

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Product

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An ecofriendly and reusable solid acid catalyst ZrO₂‐SIEC for highly selective alkylation of 2,4/2,5‐xylenol