Raney® nickel-catalyzed hydrodeoxygenation and dearomatization under transfer hydrogenation conditions—Reaction pathways of non-phenolic compounds

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Raney® nickel-catalyzed hydrodeoxygenation and dearomatization under transfer hydrogenation conditions—Reaction pathways of non-phenolic compounds. / Philippov, A. A.; Chibiryaev, A. M.; Martyanov, O. N.

In: Catalysis Today, Vol. 355, 15.09.2020, p. 35-42.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{6de53228689c482f8c55e2c876f71d74,

title = "Raney{\textregistered} nickel-catalyzed hydrodeoxygenation and dearomatization under transfer hydrogenation conditions—Reaction pathways of non-phenolic compounds",

abstract = " Catalytic reduction of oxygen-containing aromatic compounds has been studied under transfer hydrogenation (TH) conditions at 150 °C in 2-PrOH as a hydrogen donor. Raney{\textregistered} nickel is used as a heterogeneous catalyst. The reaction of aromatic non-phenolic carbonyl compounds is most likely to proceed through the pathway “aromatic ketone (aldehyde)→aromatic alcohol→alkylaromatics→saturated alkylcyclohexane”. One of the main reactions under the TH conditions is a hydrodeoxygenation (HDO) process. Unexpectedly, the hydrodeoxygenation of aromatic ketones to alkylaromatics (C[dbnd]O → CH 2 ) occurs faster than of corresponding aromatic alcohols (HC–OH → CH 2 ) that means either additional reaction pathway of its hydrodeoxygenation missing for the corresponding aromatic alcohols or specific interaction of OH functionality with Raney{\textregistered} nickel surface obstructing (hindering) the further reduction. Benzaldehyde is shown to be less reactive than the aromatic ketones under the same reaction conditions. The main reason is proposed to be carbon monoxide release resulted from the decarbonylation of the aldehyde. Carbon monoxide demonstrates a poisoning effect on Raney{\textregistered} nickel surface that is evidenced in the catalyzed TH reaction of acetophenone. The HDO reaction of anisole under the same reaction conditions was a little slowly than of oxygen-containing non-phenolic aromatics. ",

keywords = "Dearomatization, Hydrodeoxygenation, Oxygen-containing aromatics, Raney{\textregistered} nickel, Transfer hydrogenation, TRANSFER HYDROGENOLYSIS, STYRENE OXIDE, PRODUCT DISTRIBUTION, Raney (R) nickel, ALCOHOLS, PYROLYTIC LIGNIN, OIL, BIOMASS, DEOXYGENATION, FUEL, NI",

author = "Philippov, {A. A.} and Chibiryaev, {A. M.} and Martyanov, {O. N.}",

year = "2020",

month = sep,

day = "15",

doi = "10.1016/j.cattod.2019.05.033",

language = "English",

volume = "355",

pages = "35--42",

journal = "Catalysis Today",

issn = "0920-5861",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Raney® nickel-catalyzed hydrodeoxygenation and dearomatization under transfer hydrogenation conditions—Reaction pathways of non-phenolic compounds

AU - Philippov, A. A.

AU - Chibiryaev, A. M.

AU - Martyanov, O. N.

PY - 2020/9/15

Y1 - 2020/9/15

N2 - Catalytic reduction of oxygen-containing aromatic compounds has been studied under transfer hydrogenation (TH) conditions at 150 °C in 2-PrOH as a hydrogen donor. Raney® nickel is used as a heterogeneous catalyst. The reaction of aromatic non-phenolic carbonyl compounds is most likely to proceed through the pathway “aromatic ketone (aldehyde)→aromatic alcohol→alkylaromatics→saturated alkylcyclohexane”. One of the main reactions under the TH conditions is a hydrodeoxygenation (HDO) process. Unexpectedly, the hydrodeoxygenation of aromatic ketones to alkylaromatics (C[dbnd]O → CH 2 ) occurs faster than of corresponding aromatic alcohols (HC–OH → CH 2 ) that means either additional reaction pathway of its hydrodeoxygenation missing for the corresponding aromatic alcohols or specific interaction of OH functionality with Raney® nickel surface obstructing (hindering) the further reduction. Benzaldehyde is shown to be less reactive than the aromatic ketones under the same reaction conditions. The main reason is proposed to be carbon monoxide release resulted from the decarbonylation of the aldehyde. Carbon monoxide demonstrates a poisoning effect on Raney® nickel surface that is evidenced in the catalyzed TH reaction of acetophenone. The HDO reaction of anisole under the same reaction conditions was a little slowly than of oxygen-containing non-phenolic aromatics.

AB - Catalytic reduction of oxygen-containing aromatic compounds has been studied under transfer hydrogenation (TH) conditions at 150 °C in 2-PrOH as a hydrogen donor. Raney® nickel is used as a heterogeneous catalyst. The reaction of aromatic non-phenolic carbonyl compounds is most likely to proceed through the pathway “aromatic ketone (aldehyde)→aromatic alcohol→alkylaromatics→saturated alkylcyclohexane”. One of the main reactions under the TH conditions is a hydrodeoxygenation (HDO) process. Unexpectedly, the hydrodeoxygenation of aromatic ketones to alkylaromatics (C[dbnd]O → CH 2 ) occurs faster than of corresponding aromatic alcohols (HC–OH → CH 2 ) that means either additional reaction pathway of its hydrodeoxygenation missing for the corresponding aromatic alcohols or specific interaction of OH functionality with Raney® nickel surface obstructing (hindering) the further reduction. Benzaldehyde is shown to be less reactive than the aromatic ketones under the same reaction conditions. The main reason is proposed to be carbon monoxide release resulted from the decarbonylation of the aldehyde. Carbon monoxide demonstrates a poisoning effect on Raney® nickel surface that is evidenced in the catalyzed TH reaction of acetophenone. The HDO reaction of anisole under the same reaction conditions was a little slowly than of oxygen-containing non-phenolic aromatics.

KW - Dearomatization

KW - Hydrodeoxygenation

KW - Oxygen-containing aromatics

KW - Raney® nickel

KW - Transfer hydrogenation

KW - TRANSFER HYDROGENOLYSIS

KW - STYRENE OXIDE

KW - PRODUCT DISTRIBUTION

KW - Raney (R) nickel

KW - ALCOHOLS

KW - PYROLYTIC LIGNIN

KW - OIL

KW - BIOMASS

KW - DEOXYGENATION

KW - FUEL

KW - NI

UR - http://www.scopus.com/inward/record.url?scp=85065914225&partnerID=8YFLogxK

U2 - 10.1016/j.cattod.2019.05.033

DO - 10.1016/j.cattod.2019.05.033

M3 - Article

AN - SCOPUS:85065914225

VL - 355

SP - 35

EP - 42

JO - Catalysis Today

JF - Catalysis Today

SN - 0920-5861

ER -

ID: 20051085