New Oxidation Process for Production of Terephthalic Acid from p-Xylene

Ichikawa, Yataro; Yamashita, Gentaro; Tokashiki, Michiyuki; Yamaji, Takayuki

doi:10.1021/ie50724a007

Cited by 26 publications

(18 citation statements)

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“…The result is that the terephthalic acid can be highly polluted. The identification problem of the impurities produced in different p-xylene oxidation processes has already been faced (Ichikawa and Tacheuchi, 1972;Ichikawa et al, 1970;Matsuzawa, 1976). This paper describes our work for the recovery and the identification of the byproducts present in the mother liquor of a Mid-Century type oxidation process.…”

Section: Introductionmentioning

confidence: 99%

Byproduct identification in the terephthalic acid production process and possible mechanisms of their formation

Roffia¹,

Calini²,

Motta³

et al. 1984

Ind. Eng. Chem. Prod. Res. Dev.

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Ind. Eng. Chem. Prod. Res. Dev. 1984, 23, 629-634 629 cyclo[2.2.2]octane, 1449-91-8; trans-2-chloro-5-(chloromethyl)-5methyl-2-oxo-l,3,2-dioxaphosphorinane, 21071-81-8; cis-2-methoxy-5-(chloromethyl)-5-methyl-2-oxo-l,3,2-dioxaphosphorinane, 28097-12-3; trans-2-methoxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-27-3; cis-2-hydroxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-29-5; cis-2-phenoxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-30-8; trans-2-phenoxy-5-(chloromethyl)-5methyl-2-oxo-1,3,2-dioxaphosphorinane, 36895-18-8; cis-2-(4methoxyphenoxy)-5-(chloromethyl)-5-methyl-2-oxo-l,3,2-dioxaphosphorinane, 36912-31-9; trans-2-(4-methoxyphenoxy)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-32-0; cis-2-(4-methylphenoxy)-5-(chloromethyl)-5methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-33-1; trans-2-(4methylphenoxy)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-34-2; cis-2-(4-bromophenoxy)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosporinane, 36912-35-3; trans-2-(4-bromophenoxy)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-36-4; cis-2-(4-nitrophenoxy)-5-(chloromethyl)-5-methyl-2-oxo-l,3,2-dioxaphosphorinane, 36912-37-5; trans-2-(4-nitrophenoxy)-5-(chloromethyl)-5methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-38-6; cis-2-(2,4dinitrophenoxy)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-39-7; trans-2-(2,4-dinitrophenoxy)-5-(chloromethyl)-5-methyl-2-oxo-l,3,2-dioxaphosphorinane, 36912-40-0; cis-2-benzoyloxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphosphorinane, 36912-41-1; trans-2-benzoyloxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-42-2; cis-2-thiophenoxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 36912-43-3; trans-2-thiophenoxy-5-(chloromethyl)-5-methyl-2-oxo-l,3,2-dioxaphosphorinane, 36912-44-4; cis-2-(pentylamino)-5-(chloromethyl)-5-methyl-2oxo-1,3,2-dioxaphosphorinane, 92366-30-8; trans-2-(pentylamino)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane, 92366-31-9; trans-2-(4-acetylphenoxy)-5-(chloromethyl)-5methyl-2-oxo-1,3,2-dioxaphosphorinane, 92366-32-0. Literature Cited Bauman, M.; Wadsworth, W. S., Jr. J . Am. Chem. SOC. 1978, 100, 6380. Gillespie, P.; Ramirez, F.; Ugi, 1.; Marquarding, D. Angew. Chem., Int. Ed. Engl. 1973, 12, 91. Rajan, S.; Kang, S.; Gutowsky, H.; Oidfield, E. J . 8/01,

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Section: Introductionmentioning

confidence: 99%

Byproduct identification in the terephthalic acid production process and possible mechanisms of their formation

Roffia¹,

Calini²,

Motta³

et al. 1984

Ind. Eng. Chem. Prod. Res. Dev.

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“…The homogeneous catalytic mechanism of para-xylene to terephthalic acid is based on free radical generation [31][32][33][34][35][36][37]. The most common catalyst in the homogeneous catalytic system of para-xylene to terephthalic acid is cobalt, manganese, or bromine.…”

Section: Reaction Mechanism For the Homogeneous Catalytic Oxidation Smentioning

confidence: 99%

A brief review of para-xylene oxidation to terephthalic acid as a model of primary C–H bond activation

Fadzil

Hasbi

Maniam

2014

Chinese Journal of Catalysis

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“…Currently up to 70% of terephthalic acid is produced by direct oxidation of p-xylene through the AMOCO/Mid-Century process being developed in the 1960s [1][2][3][4][5][6]. p-xylene in the AMOCO process is subjected to oxidation by molecular oxygen or air in the presence of homogeneous Mn and Co catalysts with KBr as a promotor and free-radical source in acetic acid medium under the severe conditions (170-220 • C, 15-30 atm of O 2 or 50-70 atm of air), giving terephthalic acid yield of 90-97% within 4-12 h (Scheme 1) [7][8][9][10]. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Manganese and Cobalt Doped Hierarchical Mesoporous Halloysite-Based Catalysts for Selective Oxidation of p-Xylene to Terephthalic Acid

et al. 2019

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Bimetallic MnCo catalyst, supported on the mesoporous hierarchical MCM-41/halloysite nanotube composite, was synthesized for the first time and proved its efficacy in the selective oxidation of p-xylene to terephthalic acid under conditions of the AMOCO process. Quantitative yields of terephthalic acid were achieved within 3 h at 200–250 °C, 20 atm. of O2 and at a substrate to the Mn + Co ratio of 4–4.5 times higher than for traditional homogeneous system. The influence of temperature, oxygen, pressure and KBr addition on the catalyst activity was investigated, and the mechanism for the oxidation of p-toluic acid to terephthalic acid, excluding undesirable 4-carboxybenzaldehyde, was proposed.

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New Oxidation Process for Production of Terephthalic Acid from p-Xylene

Cited by 26 publications

References 0 publications

Byproduct identification in the terephthalic acid production process and possible mechanisms of their formation

Byproduct identification in the terephthalic acid production process and possible mechanisms of their formation

A brief review of para-xylene oxidation to terephthalic acid as a model of primary C–H bond activation

Manganese and Cobalt Doped Hierarchical Mesoporous Halloysite-Based Catalysts for Selective Oxidation of p-Xylene to Terephthalic Acid

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