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[ CAS No. 4249-72-3 ] {[proInfo.proName]}

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Chemical Structure| 4249-72-3
Chemical Structure| 4249-72-3
Structure of 4249-72-3 * Storage: {[proInfo.prStorage]}

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Jake G. Tillou ; Joseph J. Kuchta III ; Nathan Thornburg , et al. DOI:

Abstract: The selective hydrodeoxygenation of lignin derived aromatics represents an important step towards the valorization of biomass. With this goal in mind, we synthesized a hybrid molecular/heterogeneous catalyst comprised of a (2,6-bis(1-methylbenzimidazolyl)pyridine-4′-aminopropyltrisiloxane)palladium(II) molecular catalyst covalently bound to a solid silica support through the siloxane functional group. A series of model complexes containing C–O bonds typically found in lignin biomass were explored and varying degrees of C–O bond were achieved. The stable covalent binding of the catalyst to the support was attributed to the observed long catalyst lifetimes which led to over 6000 catalytic turnovers without catalyst deactivation. Spectroscopic characterization of the catalyst pre- and post-catalytic reactions shows the catalyst maintains molecular integrity under the reaction conditions examined. The catalyst also exhibited complete selectivity for hydrodeoxygenation over ring of oxygenated aromatic molecules.

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Pham, Xuan-Tien ; Tran, Vy Anh ; Tran, Lan-Trinh Thi , et al. DOI:

Abstract: The catalytic conversion of lignin model compounds was performed using Ru/C catalysts and an autoclave reactor. The Ru/C catalysts were prepared by the impregnation method using highly porous homemade activated carbon and characterized by XRD, SEM, and specific surface area. The catalytic reactions were performed in a high pressure/temperature reactor at different temperatures and with different solvents. The results showed that the novel Ru/C catalysts prepared from carbon supports activated by the KOH agent showed higher catalytic activity than the commercial catalyst. Ethanol and 2-propanol were suitable solvents for the cleavage of the β–O–4 ether bond of 2-phenoxy1-phenyl ethanol (~65–70% conversion) over a Ru/C-KOH-2 catalyst at 220 ?C in comparison to tert-butanol and 1-propanol solvents (~43–47% conversion of 2-phenoxy-1-phenyl ethanol). Also, the increase in reaction temperature from 200 ?C to 240 ?C enhanced the cleavage of the ether bond with an increase in phenol selectivity from 9.4% to 19.5% and improved the catalytic conversion of 2-phenoxy-1-phenyl ethanol from 46.6% to 98.5% over the Ru/C-KOH-2 catalyst and ethanol solvent. The Ru/C-KOH-2 catalyst showed outstanding conversion (98.5%) of 2-phenoxy-1-phenylethanol at 240 ?C, 1 h, ethanol solvent. This novel hierarchical porous activated carbon-supported ruthenium catalyst (Ru/C-KOH-2) can be applied for the further conversion of the lignin compound.

Keywords: active carbon ; biochar ; Ru/C ; lignin ; β-O-4 aryl ether

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De Saegher, Tibo ; Lauwaert, Jeroen ; Vercammen, Joeri , et al. DOI: PubMed ID:

Abstract: Lignin valorization and particularly its depolymerization into bio‐aromatics, has emerged as an important research topic within green chemistry. However, screening of catalysts and reaction conditions within this field is strongly constrained by the lack of analytical techniques that allow for fast and detailed mapping of the product pools. This analytical gap results from the inherent product pool complexity and the focus of the state‐of‐the‐art on monomers and dimers, overlooking the larger oligomers. In this work, this gap is bridged through the development of a quasi‐orthogonal GPC‐HPLC‐UV/VIS method that is able to separate the bio‐aromatics according to molecular weight (hydrodynamic volume) and polarity. The method is evaluated using model compounds and real lignin depolymerization samples. The resulting color plots provide a powerful graphical tool to rapidly assess differences in reaction selectivity towards monomers and dimers as well as to identify differences in the oligomers.

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Product Details of [ 4249-72-3 ]

CAS No. :4249-72-3 MDL No. :MFCD09880900
Formula : C14H14O2 Boiling Point : No data available
Linear Structure Formula :C6H5OCH2CH(C6H5)OH InChI Key :GSBICRJXEDSPTE-UHFFFAOYSA-N
M.W : 214.26 Pubchem ID :572254
Synonyms :

Calculated chemistry of [ 4249-72-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.39
TPSA : 29.46 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 2.47
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.19
Solubility : 0.14 mg/ml ; 0.000652 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.208 mg/ml ; 0.00097 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.54
Solubility : 0.00618 mg/ml ; 0.0000288 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.2

Safety of [ 4249-72-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:
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