Selective synthesis of epichlorohydrin <i>via</i> liquid-phase allyl chloride epoxidation over a modified Ti-MWW zeolite in a continuous slurry bed reactor

Ding, Luoyi; Yin, Jinpeng; Wen, Tong; Peng, Rusi; Jiang, Jingang; Xu, Hao; Wu, Peng

doi:10.1039/d0nj04491a

Cited by 10 publications

(7 citation statements)

References 47 publications

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“…7,8 Compared to traditional methods for preparing ECH, it has the advantages of low energy consumption, low waste treatment investment and environmental friendliness. 9,10 The direct epoxidation method of ALC involves adding hydrogen peroxide (H 2 O 2 ), excess ALC and a large amount of solvent methanol (MET) into the reactor, and ultimately epoxidizing to give ECH and H 2 O through the use of a catalyst. The mixture after epoxidation consists mainly of excess reactant ALC, solvent MET, target product ECH and byproduct H 2 O.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation and control of energy‐efficient processes for separating epichlorohydrin‐oriented quaternary system

Qi,

Yang,

Zhang

et al. 2024

J of Chemical Tech & Biotech

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BACKGROUNDThe direct epoxidation of allyl chloride is a clean and efficient synthesis method for producing Epichlorohydrin (ECH), which is a crucial organic intermediate widely used in the fields of renewable energy and aerospace. However, the presence of multiple azeotropes in the synthesized product using this method complicates the separation process and results in high energy consumption. To efficiently separate high‐purity ECH, this paper investigates and analyzes three separation schemes based on the phase‐equilibrium analysis, including hybrid extractive distillation (HED), pressure swing distillation (PSD), and three‐column batch distillation (TCBD).RESULTSThe operating parameters of the three separation processes are optimized by the sequential iterative optimization method that the minimum total annual cost (TAC) can reach 493 491 $/y. The thermal integration method is used for process energy‐saving optimization, and the TAC can be further reduced by 6.9%. In addition, a comprehensive evaluation based on economic, energy, environmental, and exergy analysis is conducted, and reveals that TCBD process with thermal integration is optimal. A control structure is designed for the TCBD process to enhance its robustness that the purity of ECH remains above 99.9 mol% under ±10% disturbances in feed flowrate and composition.CONCLUSIONSCompared with HED and PSD processes, the TCBD process has better economic and environmental benefits, and its control structure can effectively resist disturbances. It is reasonable to believe that the TCBD process can be an excellent solution for the industrial production of ECH.This article is protected by copyright. All rights reserved.

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Section: Introductionmentioning

confidence: 99%

“…Direct epoxidation of allyl chloride (ALC) is the most promising green synthesis technology for producing ECH 7,8 . Compared to traditional methods for preparing ECH, it has the advantages of low energy consumption, low waste treatment investment and environmental friendliness 9,10 …”

Section: Introductionmentioning

confidence: 99%

Evaluation and control of energy‐efficient processes for separating epichlorohydrin‐oriented quaternary system

Qi,

Yang,

Zhang

et al. 2024

J of Chemical Tech & Biotech

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“…Ti-MWW exhibits higher conversion than TS-1 in the propylene and cyclohexene epoxidation [15] . The catalytic activity of Ti-MWW in olefin epoxidation reactions can be further enhanced by post-modifications, such as fluoride treatment or piperidine (PI)-assisted 3D to 2D structural transformation [16][17][18][19][20] .…”

Section: Introductionmentioning

confidence: 99%

Hydrophilic Ti-MWW for catalyzing epoxidation of allyl alcohol

Gong,

Tuo,

Wang

et al. 2024

Chem Synth

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Titanosilicates are widely applied in the alkene epoxidation reactions with high reaction rate and selectivity to desired products. Their catalytic performance depends on the structure topology, the micro-environment of Ti active sites, and the hydrophobicity/hydrophilicity of zeolite framework. Herein, we focus on a hydrophilic substrate of allyl alcohol (AAL) and investigated catalytic performance of four titanosilicates (TS-1, Ti-MOR, Ti-MWW, and Re-Ti-MWW) in the AAL epoxidation reaction with hydrogen peroxide as the oxidant. Among them, Re-Ti-MWW, synthesized via the post-modification of Ti-MWW with piperidine, exhibited the highest activity. Moreover, the preferred solvent changed from MeCN for Ti-MWW to H2O for Re-Ti-MWW. The relative diffusion rate of AAL over Re-Ti-MWW was up to 466 × 10-7 s-1, much larger than those of other zeolites. The higher diffusion rate of Re-Ti-MWW was probably derived from the higher framework hydrophilicity as revealed by the smaller water contact angle of Re-Ti-MWW compared to the other zeolites, which contributed to the high activity in AAL epoxidation. In the continuous slurry reactor, Re-Ti-MWW achieved a high catalytic lifetime of 163 h, with the selectivity of desirable glycidol product maintained at > 97% in the H2O solvent system, showing high potential as an industrial catalyst for the AAL epoxidation reaction.

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“…Epichlorohydrin (ECH) is an important raw chemical material and organic intermediate that has been widely used in the production of epoxy resin, glycerol, glycidyl ether, quaternary ammonium salt, and chloro-alcohol rubber. − At present, the main industrial production methods of epichlorohydrin include the chlorination of propylene at high temperatures, the allyl alcohol method, and the glycerol method. , Traditional production methods cause serious corrosion to equipment, with most of the byproducts being treated by incineration, and generate a large amount of wastewater, thus making this process fail to meet the requirements necessary to be environmentally friendly. , Titanium silica (TS-1) molecular sieves have been widely used in olefin epoxidation, the hydroxylation of aromatic rings, oxime of cyclohexanone, and the oxidation of alcohols and saturated hydrocarbons using hydrogen peroxide as an oxidant. − The process of TS-1/H 2 O 2 catalyzing propylene chloride epoxidation to produce epichlorohydrin was shown to achieve high efficiency, environmental friendliness, and economic feasibility, greatly simplifying the process and offering good application prospects. − In industrial production, such as that for HPPO (hydrogen peroxide-epoxyrine), fixed-bed processes have gradually been developed, − and most catalysts used in fixed beds need to be shaped. , The binder used in traditional molding methods will cover the surface of the molecular sieve and active sites, leading to a low utilization rate of the catalyst. This problem can be solved by loading the molecular sieve directly on the support surfaces.…”

Section: Introductionmentioning

confidence: 99%

“… 4 , 5 Traditional production methods cause serious corrosion to equipment, with most of the byproducts being treated by incineration, and generate a large amount of wastewater, thus making this process fail to meet the requirements necessary to be environmentally friendly. 6 , 7 Titanium silica (TS-1) molecular sieves have been widely used in olefin epoxidation, the hydroxylation of aromatic rings, oxime of cyclohexanone, and the oxidation of alcohols and saturated hydrocarbons using hydrogen peroxide as an oxidant. 8 − 11 The process of TS-1/H 2 O 2 catalyzing propylene chloride epoxidation to produce epichlorohydrin was shown to achieve high efficiency, environmental friendliness, and economic feasibility, greatly simplifying the process and offering good application prospects.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Micron-Sized TS-1 Spherical Membrane Catalysts and Their Performance in the Epoxidation of Chloropropene

Tang

Yang

et al. 2023

ACS Omega

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Titanium silica (TS-1) membrane catalysts grown on the surfaces of spherical substrates can both exploit the high catalytic performance and facilitate their separation from products after the reaction. In this work, a simple static crystallization method was used to perform the in situ construction of a TS-1 membrane on the surfaces of micron-sized spherical carriers. The shortcomings of the TS-1 membrane under static crystallization conditions were overcome by in situ dynamic crystallization, and the effect of rotation speed on the formation of the molecular sieve membrane was investigated. The results showed that the molecular sieve membrane was smooth and homogeneous, with a higher synthesis efficiency at a slow rotational speed. The micron TS-1 spherical membrane catalytic chloropropene epoxidation reaction was investigated in a fixed bed, and the conversion of hydrogen peroxide and selectivity of epichlorohydrin reached 99.4 and 96.8%, respectively. After being reused twice, the catalyst still maintained a stable catalytic performance.

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Selective synthesis of epichlorohydrin via liquid-phase allyl chloride epoxidation over a modified Ti-MWW zeolite in a continuous slurry bed reactor

Abstract: The epoxidation of allyl chloride (ALC) to epichlorohydrin (ECH) with H2O2 using piperidine (PI) modified Ti-MWW catalyst (Ti-MWW-PI) in a continuous slurry reactor was investigated to develop an efficient reaction...

Cited by 10 publications

References 47 publications

Evaluation and control of energy‐efficient processes for separating epichlorohydrin‐oriented quaternary system

Evaluation and control of energy‐efficient processes for separating epichlorohydrin‐oriented quaternary system

Hydrophilic Ti-MWW for catalyzing epoxidation of allyl alcohol

Preparation of Micron-Sized TS-1 Spherical Membrane Catalysts and Their Performance in the Epoxidation of Chloropropene

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