Fiber Surface Modification. Part III. The Reaction of Lignin Model Compounds and Other Phenols with Cyanuric Chloride.

Allan, F. J.; Allan, G. G.; Mattila, T.; Mauranen, P.; Lindberg, Alf A.; Craig, J. Cymerman

doi:10.3891/acta.chem.scand.23-1903

Cited by 15 publications

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“…1 H NMR (500 MHz, DMSO-d 6 ): δ = 7.22 (ddd, J = 8.2, 7.4, 1.6 Hz, 3H, C5), 7.13 (ddd, J = 30.5, 8.1, 1.5 Hz, 6H, C4/C6), 6.93 (td, J = 7.7, 1.4 Hz, 3H, C3), 3.85 (s, 9H, OCH 3 ). 13 1,3,5-Tri(4-methoxyphenoxy)-2,4,6-triazine (4). 4 was recrystallized from MeOH to give the title product as a white solid (3.08 g, 6.97 mmol, 85%).…”

Section: See Simentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ): δ = 7.67 (dd, J = 8.3, 1.9 Hz, 3H, C5H), 7.62 (d, J = 1.9 Hz, 3H, C3H), 7.16 (d, J = 8.3 Hz, 3H, C6H), 3.93 (s, 9H, OCH 3 ), 3.83 (s, 9H, COOCH 3 ). 13 1,3,5-Tri(4-benzoyloxy)-2,4,6-triazine (9). After filtration and vacuum drying, the product was obtained as a white solid (1.54 g, 3.15 mmol, 76%).…”

Section: See Simentioning

confidence: 99%

“…Allan et al have reported its reaction with a variety of phenols to produce the 1,3,5-triaryloxy-2,4,6-triazines in moderate-to-good yields, though characterization of the compounds was limited to the melting point and CHN analysis, while Sagar et al increased the yields using a microwave synthesis . Forbes made triarylcyanurates with phenols, then used these in cross-linking reactions of lignosulfonate .…”

Section: Introductionmentioning

confidence: 99%

“…13 C NMR (126 MHz, DMSO-d 6 ): δ = 172.70, 166.41, 154.53, 130.90, 128.59, 121.61. HRMS (ES+ mode): m/z = 490.0883 [100%, MH + ]; calculated for C 24 H 15 N 3 O 9 requires [MH + ]: m/z = 490.0881.…”

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A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

Zhao

King

Kwan

et al. 2016

Org. Process Res. Dev.

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A low energy, high selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equivalents of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equivalents of de oxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multi phasic process for converting guaiacol to anisole, and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate by product. Green chemistry aspects, and the potential for industrial adoption are discussed. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 3 conditions, 4 however it has often required catalytic reforming at >300 o C temperature, resulting in over reduction with complex product mixtures and catalyst deactivation. 5 For example cobalt molybdenum sulfide on alumina catalyst at 300 o C and 50 bar has been shown to convert 84% of the guaiacol to give 34% phenol, 11% catechol, 3% anisole, 1% benzene and the remainder saturated products. 6 The extreme conditions are required because the aromatic C O bond is strong with a length of 1.37 Å and bond energy of 460 kJ.mol 1 , compared to the aliphatic C O bond of 1.43 Å and 358 kJ.mol 1 . 7 In the organic laboratory the hydrogenolysis of phenolic compounds is usually carried out by activation with trifluoromethanesulfonyl chloride followed by reduction; however the cost of making triflates and the associated waste make this method too expensive and wasteful to consider for bulk production. 8 Reports of aryl alkyl ether reduction, using either nickel catalysts and silane reductants, or better from an industrial perspective, a combination of metal triflate and palladium catalysts with hydrogen, both illustrate the difficulties in this transformation. 9 Another reported phenol activation method is reacting phenyl tetrazolium chloride with the phenol to make the corresponding 5 aryloxy 1 phenyltetrazoyl ethers, with similar disadvantages and low atom efficiency. 10 The electron withdrawing and resonance stabilizing tetrazolyl group can weaken the aromatic C O bond, facilitating its cleavage by catalytic hydrogenolysis. Alves has used X ray crystal structures to show lengthening of the aromatic C O bond to 1.42 Å, with the bond energy reduced by around 100 kJ.mol 1 . 11 A better industrial reagent is cyanuric chloride, made from cyanogen chloride. It is used widely in the manufacture of fiber reactive dyes and agrochemicals, and is produced at >100 ktpa at about £1.50/kg. 12 Furthermore it has the ...

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Section: See Simentioning

confidence: 99%

Section: See Simentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

Zhao

King

Kwan

et al. 2016

Org. Process Res. Dev.

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“…Despite the allowance of a substantial period of time, no reaction of cyanurchloride and 4-cyanophenol at 190-200 uC was detected using the known solvent-free procedure 1. 4 A different synthetic method 2 (Scheme 1) including the application of a base in aqueous solution reported by Allan et al 5 did not lead to the desired product either.…”

Section: Resultsmentioning

confidence: 98%

2,4,6-Tris(4-cyanophenoxy)-1,3,5-triazine (CNPOT): Trigonal synthons in crystal engineering

2005

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Fibre surface modification XI. The covalent attachment of fungicides to lignocellulosic fibres

Allan

Halabisky

1971

J. Appl. Chem.

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Pentachlorophenol was covalently bonded to a softwood kraft pulp by an s‐triazine bridge formed from cyanuric chloride in a mild aqueous reaction system. The tensile properties of paper made from the polypentachlorophenoxy‐s‐triazinylated fibres containing 3.9% of combined fungicide were completely maintained for 49 days during fungal attack by Lenzites trabea. Protection is probably a result of the release of pentachlorophenol from the fibre triggered by the attacking fungus.

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Fiber Surface Modification. Part III. The Reaction of Lignin Model Compounds and Other Phenols with Cyanuric Chloride.

Cited by 15 publications

References 0 publications

A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

2,4,6-Tris(4-cyanophenoxy)-1,3,5-triazine (CNPOT): Trigonal synthons in crystal engineering

Fibre surface modification XI. The covalent attachment of fungicides to lignocellulosic fibres

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