@inbook {2453,
	title = {New Chemistry, Including Pulp Bleaching Processes, of the Golden-Aged, Water-Soluble Compound, Tris(hydroxymethyl)phosphine},
	booktitle = {Catalysis of Organic Reactions},
	series = {Chemical Industries},
	volume = {123},
	year = {2009},
	note = {ISI Document Delivery No.: BLT07Times Cited: 0Cited Reference Count: 85James, Brian R.Proceedings Paper22nd Conference on Catalysis of Organic ReactionsMAR 30-APR 03, 2008Richmond, VAOrgan React Catalysis Soc, Avantium, BASF Catalysis LLC, Eli Lilly, Evonik Degussa Corp, WR Grace, Davison Catalysts, Parr Instrument, Air Prod, Amgen, Eastman, Umicore, Bristol Myers Squibb, DuPont, Headwaters, HEI, Lummus Technol, OMG, Seton Hall Univ, Sud Chem6000 BROKEN SOUND PARKWAY NW, STE 300, BOCA RATON, FL 33487-2742 USA},
	pages = {1-14},
	publisher = {Crc Press-Taylor \& Francis Group},
	organization = {Crc Press-Taylor \& Francis Group},
	address = {Boca Raton},
	abstract = {Collaborative studies with the Pulp and Paper Institute of Canada (Paprican) have led serendipitously to development of a pulp bleaching process using tris(hydroxymethyl)phosphine, P(CH2OH)(3) (abbreviated THP), and this on-going work is reviewed. Work on hydrogenation of aromatic residues in lignin, using transition metal catalysts under homogeneous, aqueous-phase conditions, led to the discovery that commercially available THP, in the absence of any metal, bleached selected pulps. Use of THP or a related diphosphine 2 is competitive with the currently used bleaching agents, hydrosulfite (S2O42-) and alkaline peroxide. (Hydroxymethyl)phosphines react as strong nucleophiles and/or reductants toward unsaturated chromophore moieties of lignin, decreasing the degree of conjugation, and hence leading to bleaching. The resulting phosphorus-containing moieties in the lignin also give a more permanent brightening of the pulp. The organo-phosphorus chemistry realized is relevant to other processes catalyzed homogeneously by transition metal-phosphine systems. In situ metal-THP species can catalyze hydrogenation of C=C and/or C=O bonds in lignin chromophores, and investigations on such systems have unearthed new THP-promoted transition metal chemistry.},
	keywords = {BIPHASIC CONDITIONS, BRIGHTNESS STABILIZING AGENTS, CATALYTIC-HYDROGENATION, CLUSTER CATALYSIS, HOMOGENEOUS CATALYST, LIGNIN MODEL COMPOUNDS, mechanical, PHOSPHORUS-COMPOUNDS, pulps, ruthenium complexes, TERTIARY PHOSPHINES},
	isbn = {978-1-4200-7076-7},
	url = {<Go to ISI>://000270967300001},
	author = {James, Brian R.},
	editor = {Prunier, M. L.}
}
@article {1500,
	title = {alpha-monodeuterated benzyl alcohols and phosphobetaines from reactions of aromatic aldehydes with a water/D2O-soluble phosphine},
	journal = {Inorganic Chemistry},
	volume = {45},
	number = {25},
	year = {2006},
	note = {ISI Document Delivery No.: 111UETimes Cited: 11Cited Reference Count: 49Moiseev, Dmitry V. James, Brian R. Hu, Thomas Q.},
	month = {Dec},
	pages = {10338-10346},
	type = {Article},
	abstract = {With the aim of learning more about the bleaching action of pulps by (hydroxymethyl) phosphines, we reacted several benzaldehydes, containing MeO, Me, OH, or halogen substituents, with tris(3-hydroxypropyl) phosphine, [HO(CH2)(3)](3)P, in aqueous solution at 90 degrees C under argon. Effective reduction of the aldehydes to the corresponding benzyl alcohols with concomitant oxidation of the phosphine to the phosphine oxide takes place, the reaction proceeding via an initially formed phosphonium species. When the reactions are carried out in D2O, the benzyl alcohol product from 3,4-dimethoxybenzaldehyde contains one deuterium atom at the benzyl-carbon atom, consistent with the last step of the mechanism involving a carbanion intermediate. With syringaldehyde (3,5-dimethoxy-4-hydroxy-benzaldehyde), the reduction product (syringyl alcohol) is more reactive toward the phosphine than is the starting aldehyde, and a zwitterionic, phosphobetaine product is formed. In D2O, the zwitterion benzyl protons and protons of the hydroxypropyl-CH2 adjacent to the P atom undergo H/D exchange via presumed phosphorus ylide intermediates. Under the same aqueous reaction conditions, tris(3-hydroxypropyl) phosphine, [HO(CH2)(3)](3)P (THPP), does not undergo redox reactions with aliphatic aldehydes but simply promotes a base-catalyzed self-condensation (aldol) reaction. THPP reduction of an aromatic ketone is sluggish, presumably because the carbonyl C-atom is less electrophilic than that present in an aromatic aldehyde.},
	keywords = {ALIPHATIC ALDEHYDES, BRIGHTNESS STABILIZING AGENTS, CONDENSATION REACTIONS, CRYSTAL-STRUCTURE, HYDROGENATION, LIGNIN MODEL COMPOUNDS, mechanical pulps, METHIDE, NUCLEOPHILIC-ADDITION, P-QUINONE, PHOSPHONIUM SALTS},
	isbn = {0020-1669},
	url = {<Go to ISI>://000242479700055},
	author = {Moiseev, D. V. and James, Brian R. and Hu, Thomas Q.}
}
@article {1500,
	title = {alpha-monodeuterated benzyl alcohols and phosphobetaines from reactions of aromatic aldehydes with a water / D2O-soluble phosphine},
	journal = {Inorganic Chemistry},
	volume = {45},
	number = {25},
	year = {2006},
	note = {ISI Document Delivery No.: 111UETimes Cited: 11Cited Reference Count: 49Moiseev, Dmitry V. James, Brian R. Hu, Thomas Q.},
	month = {Dec},
	pages = {10338-10346},
	type = {Article},
	abstract = {<p>With the aim of learning more about the bleaching action of pulps by (hydroxymethyl) phosphines, we reacted several benzaldehydes, containing MeO, Me, OH, or halogen substituents, with tris(3-hydroxypropyl) phosphine, [HO(CH2)(3)](3)P, in aqueous solution at 90 degrees C under argon. Effective reduction of the aldehydes to the corresponding benzyl alcohols with concomitant oxidation of the phosphine to the phosphine oxide takes place, the reaction proceeding via an initially formed phosphonium species. When the reactions are carried out in D2O, the benzyl alcohol product from 3,4-dimethoxybenzaldehyde contains one deuterium atom at the benzyl-carbon atom, consistent with the last step of the mechanism involving a carbanion intermediate. With syringaldehyde (3,5-dimethoxy-4-hydroxy-benzaldehyde), the reduction product (syringyl alcohol) is more reactive toward the phosphine than is the starting aldehyde, and a zwitterionic, phosphobetaine product is formed. In D2O, the zwitterion benzyl protons and protons of the hydroxypropyl-CH2 adjacent to the P atom undergo H/D exchange via presumed phosphorus ylide intermediates. Under the same aqueous reaction conditions, tris(3-hydroxypropyl) phosphine, [HO(CH2)(3)](3)P (THPP), does not undergo redox reactions with aliphatic aldehydes but simply promotes a base-catalyzed self-condensation (aldol) reaction. THPP reduction of an aromatic ketone is sluggish, presumably because the carbonyl C-atom is less electrophilic than that present in an aromatic aldehyde.</p>},
	keywords = {ALIPHATIC ALDEHYDES, BRIGHTNESS STABILIZING AGENTS, CONDENSATION REACTIONS, CRYSTAL-STRUCTURE, HYDROGENATION, LIGNIN MODEL COMPOUNDS, mechanical pulps, METHIDE, NUCLEOPHILIC-ADDITION, P-QUINONE, PHOSPHONIUM SALTS},
	isbn = {0020-1669},
	url = {<Go to ISI>://000242479700055},
	author = {Moiseev, D. V. and James, Brian R. and Hu, Thomas Q.}
}
@article {5136,
	title = {Tetrazole ethers from lignin model phenols: synthesis, crystal structures, and photostability},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {79},
	number = {8},
	year = {2001},
	note = {ISI Document Delivery No.: 473WGTimes Cited: 1Cited Reference Count: 24},
	month = {Aug},
	pages = {1201-1206},
	type = {Article},
	abstract = {{The phenolic OH moiety in lignin is one of the key functional groups responsible for the photo-induced yellowing of mechanical wood pulps and papers. To evaluate new protective groups for the stabilization of lignin phenols, the model compounds, 2-methoxy-4-propylphenol (1) and 4-hydroxy-3-methoxyacetophenone (2) were reacted with 5-chloro-1-phenyl-1H-tetrazole to give the corresponding tetrazole ethers 1{\textquoteright} and 2{\textquoteright}, respectively, that were then studied for their photostability. The synthesis of these ethers was more efficient than that of alkyl ethers because of less hydrolysis of the alkylating agent under the reaction conditions. Compounds 1{\textquoteright} and 2{\textquoteright} were fully characterized, including X-ray crystal structure analyses. Crystals of 1{\textquoteright} and 2{\textquoteright} were monoclinic of space groups P2(1)/c and P2(1)/a, respectively. For 1{\textquoteright}: a = 9.8679(6)},
	keywords = {ALKYLATION, ETHERS, HIGH-YIELD PULPS, LIGHT, LIGNIN MODEL COMPOUNDS, METHYLATION, PHENOLS, yellowing inhibition},
	isbn = {0008-4042},
	url = {<Go to ISI>://000171071400001},
	author = {Lu, A. Z. and Hu, Thomas Q. and Osmond, D. A. and Patrick, B. O. and James, Brian R.}
}
@article {5136,
	title = {Tetrazole ethers from lignin model phenols: synthesis, crystal structures, and photostability},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {79},
	number = {8},
	year = {2001},
	note = {ISI Document Delivery No.: 473WGTimes Cited: 1Cited Reference Count: 24},
	month = {Aug},
	pages = {1201-1206},
	type = {Article},
	abstract = {{The phenolic OH moiety in lignin is one of the key functional groups responsible for the photo-induced yellowing of mechanical wood pulps and papers. To evaluate new protective groups for the stabilization of lignin phenols, the model compounds, 2-methoxy-4-propylphenol (1) and 4-hydroxy-3-methoxyacetophenone (2) were reacted with 5-chloro-1-phenyl-1H-tetrazole to give the corresponding tetrazole ethers 1{\textquoteright} and 2{\textquoteright}, respectively, that were then studied for their photostability. The synthesis of these ethers was more efficient than that of alkyl ethers because of less hydrolysis of the alkylating agent under the reaction conditions. Compounds 1{\textquoteright} and 2{\textquoteright} were fully characterized, including X-ray crystal structure analyses. Crystals of 1{\textquoteright} and 2{\textquoteright} were monoclinic of space groups P2(1)/c and P2(1)/a, respectively. For 1{\textquoteright}: a = 9.8679(6)},
	keywords = {ALKYLATION, ETHERS, HIGH-YIELD PULPS, LIGHT, LIGNIN MODEL COMPOUNDS, METHYLATION, PHENOLS, yellowing inhibition},
	isbn = {0008-4042},
	url = {<Go to ISI>://000171071400001},
	author = {Lu, A. Z. and Hu, Thomas Q. and Osmond, D. A. and Patrick, B. O. and James, Brian R.}
}
@article {4833,
	title = {Removal of phenolic hydroxyl groups in lignin model compounds and its effect on photostability},
	journal = {Holzforschung},
	volume = {54},
	number = {2},
	year = {2000},
	note = {ISI Document Delivery No.: 301QHTimes Cited: 3Cited Reference Count: 24},
	pages = {127-132},
	type = {Article},
	abstract = {The phenolic hydroxyl groups in the lignin model compounds, 2-methoxy-4-propylphenol and 4-hydroxy-3-methoxyacetophenone, were removed by first converting the hydroxyl groups to the trifluoromethanesulfonates (triflates) and then cleaving the triflate substituents via catalytic hydrogen transfer. The products, 1-methoxy-3-propylbenzene and 3-methoxyacelophenone: were characterized by H-1 and C-13 NMR, mass spectrometry and elemental analyses. The effect of the removal of the phenolic groups on the photostability of the model compounds was evaluated by impregnating the compounds into Whatman filter paper sheets, and subjecting them to an accelerated yellowing experiment in a UV chamber. The removal of the phenolic groups resulted in a significant yellowing inhibition, with a higher photostabilizing effect than methylation or acetylation of the hydroxyl, particularly for the model compound without an alpha-carbonyl group.},
	keywords = {ACETYLATION, DEGRADATION, DEOXYGENATION, GROUPS, HYDROGENATION, LIGNIN MODEL COMPOUNDS, METAL, METHYLATION, phenolic hydroxyl, photostability yellowing, REDUCTION},
	isbn = {0018-3830},
	url = {<Go to ISI>://000086320500004},
	author = {Hu, Thomas Q. and Cairns, G. R. and James, Brian R.}
}
@article {4833,
	title = {Removal of phenolic hydroxyl groups in lignin model compounds and its effect on photostability},
	journal = {Holzforschung},
	volume = {54},
	number = {2},
	year = {2000},
	note = {ISI Document Delivery No.: 301QHTimes Cited: 3Cited Reference Count: 24},
	pages = {127-132},
	type = {Article},
	abstract = {The phenolic hydroxyl groups in the lignin model compounds, 2-methoxy-4-propylphenol and 4-hydroxy-3-methoxyacetophenone, were removed by first converting the hydroxyl groups to the trifluoromethanesulfonates (triflates) and then cleaving the triflate substituents via catalytic hydrogen transfer. The products, 1-methoxy-3-propylbenzene and 3-methoxyacelophenone: were characterized by H-1 and C-13 NMR, mass spectrometry and elemental analyses. The effect of the removal of the phenolic groups on the photostability of the model compounds was evaluated by impregnating the compounds into Whatman filter paper sheets, and subjecting them to an accelerated yellowing experiment in a UV chamber. The removal of the phenolic groups resulted in a significant yellowing inhibition, with a higher photostabilizing effect than methylation or acetylation of the hydroxyl, particularly for the model compound without an alpha-carbonyl group.},
	keywords = {ACETYLATION, DEGRADATION, DEOXYGENATION, GROUPS, HYDROGENATION, LIGNIN MODEL COMPOUNDS, METAL, METHYLATION, phenolic hydroxyl, photostability yellowing, REDUCTION},
	isbn = {0018-3830},
	url = {<Go to ISI>://000086320500004},
	author = {Hu, Thomas Q. and Cairns, G. R. and James, Brian R.}
}
@article {4002,
	title = {Towards inhibition of yellowing of mechanical pulps .1. Catalytic hydrogenation of lignin model compounds under mild conditions},
	journal = {Journal of Pulp and Paper Science},
	volume = {23},
	number = {4},
	year = {1997},
	note = {ISI Document Delivery No.: WU947Times Cited: 19Cited Reference Count: 19},
	month = {Apr},
	pages = {J153-J156},
	type = {Article},
	abstract = {Di-mu-chloro-bis(eta(4)-1,5-hexadiene) dirhodium(I) effectively catalyzed the hydrogenation of the aromatic rings of the lignin model compounds 4-propylphenol, eugenol, 1,2-dimethoxy-4-propylbenzene and 2,6-dimethoxy-4-propyl-phenol under extremely mild conditions (25 degrees C, I atm H-2) in a two-phase, hexane/aqueous pH 7.5 medium. This catalyst was more active than di-mu-chloro-bis(eta(4)-1,5-cyclooctadiene)-dirhodium(I), rhodium(III) trichloride trihydrate and ruthenium(III) trichloride trihydrate. The reactivity of three predominant functional groups in lignin toward the rhodium(I) catalyzed hydrogenation followed the descending order of carbon-carbon double bond > aromatic ring > carbonyl group. The hydrogenation reactions were sensitive to steric and electronic effects of the substituent(s) on the aromatic rings. Moderate to extremely high diastereoselectivities were observed for the hydrogenated products.},
	keywords = {aromatic groups, carbonyl groups, CATALYSTS, CHROMOPHORES, eugenol, HYDROGENATION, HYDROGENOLYSIS, INHIBITION, LIGNIN MODEL COMPOUNDS, mechanical pulps, QUINONES, yellowing},
	isbn = {0826-6220},
	url = {<Go to ISI>://A1997WU94700002},
	author = {Hu, Thomas Q. and James, Brian R. and Lee, C. L.}
}
@article {4002,
	title = {Towards inhibition of yellowing of mechanical pulps .1. Catalytic hydrogenation of lignin model compounds under mild conditions},
	journal = {Journal of Pulp and Paper Science},
	volume = {23},
	number = {4},
	year = {1997},
	note = {ISI Document Delivery No.: WU947Times Cited: 19Cited Reference Count: 19},
	month = {Apr},
	pages = {J153-J156},
	type = {Article},
	abstract = {Di-mu-chloro-bis(eta(4)-1,5-hexadiene) dirhodium(I) effectively catalyzed the hydrogenation of the aromatic rings of the lignin model compounds 4-propylphenol, eugenol, 1,2-dimethoxy-4-propylbenzene and 2,6-dimethoxy-4-propyl-phenol under extremely mild conditions (25 degrees C, I atm H-2) in a two-phase, hexane/aqueous pH 7.5 medium. This catalyst was more active than di-mu-chloro-bis(eta(4)-1,5-cyclooctadiene)-dirhodium(I), rhodium(III) trichloride trihydrate and ruthenium(III) trichloride trihydrate. The reactivity of three predominant functional groups in lignin toward the rhodium(I) catalyzed hydrogenation followed the descending order of carbon-carbon double bond > aromatic ring > carbonyl group. The hydrogenation reactions were sensitive to steric and electronic effects of the substituent(s) on the aromatic rings. Moderate to extremely high diastereoselectivities were observed for the hydrogenated products.},
	keywords = {aromatic groups, carbonyl groups, CATALYSTS, CHROMOPHORES, eugenol, HYDROGENATION, HYDROGENOLYSIS, INHIBITION, LIGNIN MODEL COMPOUNDS, mechanical pulps, QUINONES, yellowing},
	isbn = {0826-6220},
	url = {<Go to ISI>://A1997WU94700002},
	author = {Hu, Thomas Q. and James, Brian R. and Lee, C. L.}
}
