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Chemical reaction in which a C–C or C–R bond is cleaved by hydrogen
hydrogenolysis is conducted catalytically using hydrogen gas. The term "hydrogenolysis" was coined by Carleton Ellis in reference to hydrogenolysis of
Hydrogenolysis
Chemical compound
preferred over palladium catalysts to minimize hydrogenolysis. The catalyst is also used for the hydrogenolysis of phenyl phosphate esters, a reaction that
Adams'_catalyst
Removal of sulfur from a substance
usually refers to the removal of sulfur from a molecule or a material by hydrogenolysis: R2S + 2 H2 → 2RH + H2S Hydrogen is the ultimate sulfur acceptor. As
Desulfurization
Chemical compound
common catalyst for hydrogenolysis. Such reactions are helpful in deprotection strategies. Particularly common substrates for hydrogenolysis are benzyl ethers:
Palladium_on_carbon
Chemical compound
the reaction of methylamine and diethylene glycol as well as by the hydrogenolysis of N-formylmorpholine. It is the precursor to N-methylmorpholine N-oxide
N-Methylmorpholine
Methods of hydrogenation and hydrogenolysis of organic compounds
Reductions with hydrosilanes are methods used for hydrogenation and hydrogenolysis of organic compounds. The approach is a subset of ionic hydrogenation
Reductions_with_hydrosilanes
Chemical compound
formula (CH3)2CHC6H10CH3. It is the product of the hydrogenation or hydrogenolysis of various terpenoids, including p-cymene, terpinolenes, phellandrene
P-Menthane
Chemical process used to remove sulfur in natural gas and oil refining
net result of a hydrogenolysis reaction is the formation of C-H and H-X chemical bonds. Thus, hydrodesulfurization is a hydrogenolysis reaction. Using
Hydrodesulfurization
Chemical element with atomic number 74 (W)
containing catalysts are promising for epoxidation, oxidation, and hydrogenolysis reactions. Tungsten heteropoly acids are key component of multifunctional
Tungsten
Group of atoms introduced into a compound to prevent subsequent reactions
by hydrogenolysis p-Methoxybenzyl (PMB) – Removed by hydrogenolysis, more labile than benzyl 3,4-Dimethoxybenzyl (DMPM) – Removed by hydrogenolysis, more
Protecting_group
Chemical element with atomic number 1 (H)
hydrodesulfurization and hydrocracking. Many of these reactions can be classified as hydrogenolysis, i.e., the cleavage of bonds by hydrogen. Illustrative is the separation
Hydrogen
Chemical compound
"Hydrogenation and Hydrogenolysis. VII. Selective Hydrogenation of Aromatic Compounds Containing C–O Linkages Liable to Hydrogenolysis with a Rhodium-Platinum
Rhodium-platinum_oxide
Process of increasing the rate of a chemical reaction
hydrogenation operations, large planes of metal surface function as sites of hydrogenolysis catalysis while sites catalyzing hydrogenation of unsaturates are smaller
Catalysis
Chemical compound
is normally manufactured by catalytic hydrogenolysis of furfural alcohol or via a hydrogenation-hydrogenolysis sequence from furfural in the vapor phase
2-Methylfuran
Chemical compound
5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis". Green Chemistry. 21 (15): 4169–4177. doi:10.1039/C9GC01645G. ISSN 1463-9262
5-Methylfurfural
Type of saturated hydrocarbon compound
hydrogenation: RCH=CH2 + H2 → RCH2−CH3 (R = alkyl) Another route to alkanes is hydrogenolysis, which entails cleavage of C-heteroatom bonds using hydrogen. In industry
Alkane
Conjugate base of an alcohol
Mo2(O2CO−t−Bu)2(O−t−Bu)4 The metal-alkoxide bond is susceptible to hydrogenolysis, especially for platinum metal derivatives: L(n)M−OR + H2 → L(n)MH +
Transition metal alkoxide complex
Transition_metal_alkoxide_complex
Organic reduction of any carbonyl group by a reducing agent
special case of carbonyl reduction entails complete deoxygenation, i.e. hydrogenolysis. This result is often undesirable because it involves defunctionalization
Carbonyl_reduction
Agricultural sub-discipline of applied chemistry
acid methyl esters can then be produced by transesterification. Alternatively, C16 and C18 diesel fuels arise by hydrogenolysis of the saturated fat.
Agricultural_chemistry
Chemical compound
precursor to several drugs and pesticides. It is produced by partial hydrogenolysis of hexamethylene diamine. Like many amines, it reacts with carbon dioxide
Azepane
Fuel made from vegetable oils or animal fats
double bonds. Fatty acid methyl esters can then be produced by transesterification. C16 and C18 diesel fuels arise by hydrogenolysis of the saturated fat.
Biodiesel
Chemical compound
1794 Luche reduction CoCl2 reduction of azides to amines 1822 InCl3 hydrogenolysis of alkyl bromides, double reduction of unsaturated ketones 1825, 1793
Sodium_borohydride
Chemical compound
reaction, followed by nitration, reduction of the nitro groups, and hydrogenolysis of the benzyl protecting groups. Adrenochrome Adrenolutin "5,6-Dihydroxyindole"
5,6-Dihydroxyindole
Aromatic alcohol
esters are popular protecting groups because they can be removed by mild hydrogenolysis.[failed verification] Benzyl alcohol reacts with acrylonitrile to give
Benzyl_alcohol
Antioxidant
6-di-tert-butylphenol by hydroxymethylation or aminomethylation followed by hydrogenolysis.[citation needed] The species behaves as a synthetic analog of vitamin
Butylated_hydroxytoluene
Organic compounds
hemicellulose; the main conversion technologies use H2 as the reagent: hydrogenolysis, i.e. the cleavage of C−O single bonds, converting polymers to smaller
Sugar_alcohol
Chemical compound
ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis: C6H5CH2NH2 + 2 RBr → C6H5CH2NR2 + 2 HBr C6H5CH2NR2 + H2 → C6H5CH3 +
Benzylamine
Facility that processes crude oil
such as hydrocracking and hydrodesulfurization. A side reaction is hydrogenolysis, which produces light hydrocarbons of lower value, such as methane,
Oil_refinery
Chemical compound
an isocyanate with benzyl alcohol (as in the Curtius rearrangement). Hydrogenolysis in the presence of a variety of palladium-based catalysts is the usual
Benzyl_chloroformate
Chemical reaction
Karl Wilhelm Rosenmund, who first reported it in 1918. The reaction, a hydrogenolysis, is catalysed by palladium on barium sulfate, which is sometimes called
Rosenmund_reduction
Chemical group (–CH2–C6H5)
enhanced reactivity, as in oxidation, free radical halogenation, or hydrogenolysis. As a practical example, in the presence of suitable catalysts, p-xylene
Benzyl_group
Edible vegetable oil from the fruit of oil palms
standard for biodiesels. Hydrodeoxygenated biodiesel is produced by direct hydrogenolysis of the fat into alkanes and propane. The world's largest palm oil biodiesel
Palm_oil
Antibiotic
moiety with a hydrogen, creating a compound named tetracycline via hydrogenolysis. Tetracycline displayed higher potency, better solubility, and more
Tetracycline
Chemical process used in oil refining
such as hydrocracking and hydrodesulfurization. A side reaction is hydrogenolysis, which produces light hydrocarbons of lower value, such as methane,
Catalytic_reforming
Chemical compound
reduction, the tetra-O-benzyl galactose converts to tetra-O-benzyltagatose. Hydrogenolysis removes the four benzyl groups, leaving tagatose. Tagatose also can
Tagatose
Chemical compound
first intermediate compound (3). Four benzyl groups selectively undergo hydrogenolysis using palladium on carbon and hydrogen. The amino groups are then acetylated
Hexanitrohexaazaisowurtzitane
Chemical compound
(CH3)3CNH2 + HCO2H}}} In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide. tert-Butylamine
Tert-Butylamine
Chemical compound
terephthalate. It is generated both by the oxidation of p-xylene as well as the hydrogenolysis of 4-carboxybenzaldehyde. In related processes it is converted to methyl
P-Toluic_acid
Measure of reaction efficiency
of such hazardous material disposal can be considerable. Catalytic hydrogenolysis of an ester is the analogous reaction with a high atom economy, but
Atom_economy
Chemical process for removing oxygen from a compound
Hydrodeoxygenation (HDO) is a hydrogenolysis process for removing oxygen from oxygen-containing compounds. Typical HDO catalysts commonly are sulfided
Hydrodeoxygenation
Chemical reaction between molecular hydrogen and another compound or element
for each reaction vessel. Since many hydrogenation reactions such as hydrogenolysis of protecting groups and the reduction of aromatic systems proceed extremely
Hydrogenation
Chemical compound
Activated single bonds to heteroatoms can also be replaced by hydrogens (hydrogenolysis). Ammonium formate can be used for reductive amination of aldehydes
Ammonium_formate
Chemical reactions that convert carbon monoxide and hydrogen into liquid hydrocarbons
CH2 The conversion of CO to alkanes involves hydrogenation of CO, the hydrogenolysis (cleavage with H2) of C–O bonds, and the formation of C–C bonds. Such
Fischer–Tropsch_process
Aromatic organochlorine compound
protecting groups. Debenzylation of such ethers can be achieved by hydrogenolysis using palladium on carbon. C6H5CH2OR + H2 → C6H5CH3 + HOR Benzyl chloride
Benzyl_chloride
Chemical compound
Another route involves hydroxymethylation of diethanolamine followed by hydrogenolysis. Amine gas treating Matthias Frauenkron, Johann-Peter Melder, Günther
Methyldiethanolamine
Chemical compound
such as the esters or acyl chloride. TFEA can also be prepared by hydrogenolysis of compounds of generic formula CF3−CHOH−OR (where R is hydrogen or
2,2,2-Trifluoroethanol
Chemical compound
hydrogenation of glutaric acid and its derivatives. It can also be prepared by hydrogenolysis of tetrahydrofurfuryl alcohol. 1,4-Pentadiene can be prepared from 1
1,5-Pentanediol
Chemical compound
1002/anie.201003236. PMID 20683835. Ferenc Notheisz, Mihály Bartók, "Hydrogenolysis of C–O, C–N and C–X bonds", p. 416 in, R. A. Sheldon, Herman van Bekkum
Tetrahydropyran
Chemical compound
secondary amines via reductive amination. The catalyst can also effect hydrogenolysis of organosulfur compounds, aldehydes, ketones, phenols and carboxylic
Molybdenum_disulfide
Chemical compound
reduction, the tetra-O-benzyl aldose converts to tetra-O-benzylsorbose. Hydrogenolysis removes the four benzyl groups, leaving sorbose. Merck Index, 12th Edition
Sorbose
Organic chemical reaction
substrates that are stable to strong bases. For substrates stable to hydrogenolysis in the presence of Raney nickel, a milder two-step Mozingo reduction
Clemmensen_reduction
Chemical compound
nitrite in acetic acid to afford diethyl oximinomalonate, catalytic hydrogenolysis of which in ethanol over Pd/C affords diethyl aminomalonate (DEAM).
Diethyl_malonate
Comparison of a wide range of pressures
Under High Heels". The Physics Factbook. Retrieved 2011-10-09. For hydrogenolysis esters with copper chromite. Paquette, L. A. (1995). Encyclopedia of
Orders of magnitude (pressure)
Orders_of_magnitude_(pressure)
Class of chemical substance
(May 2008). "Ruthenium nanoparticles inside porous [Zn4O(bdc)3] by hydrogenolysis of adsorbed [Ru(cod)(cot)]: a solid-state reference system for surfactant-stabilized
Metal–organic_framework
Redox reaction that takes place with organic compounds
reaction of saturated organic compounds with hydrogen gas is called hydrogenolysis. Hydrogenolyses necessarily cleaves C-X bonds (X = C, O, N, etc.). Reductions
Organic_redox_reaction
Chemical reaction
corresponding acetoacetate esters. Benzyl groups can be removed by catalytic hydrogenolysis over palladium on carbon, and tertiary-butyl groups can be removed by
Knorr_pyrrole_synthesis
Chemical reaction
L.; Karabinos, J. V. (June 1944). "Carbonyl Reduction by Thioacetal Hydrogenolysis". Journal of the American Chemical Society. 66 (6): 909–911. doi:10
Mozingo_reduction
Chemical compound
catalysts. Such catalysts are used in hydrogen-deuterium exchange, hydrogenolysis, and isomerization reactions. It is well suited to this purpose as 2
2,2-Dimethylbutane
Chemical compound, Si(OH)4
the parent acid. Orthosilicic acid can be produced by Pd-catalyzed hydrogenolysis of tetrabenzoxysilicon: Si(OCH2Ph)4 + 4 H2 → Si(OH)4 + 4 PhCH3 The acid
Orthosilicic_acid
Chemical compound
(4) hydroxylated aromatics, or (5) hydroxylated quinones; the (6) hydrogenolysis of dibromocyclohexanetetrols; the (7) hydration of diepoxycyclohexanes;
1,2,3,4-Cyclohexanetetrol
Chemical reaction in which a carbon-halogen bond is cleaved
desirable from the perspective of remediation are dehalogenations by hydrogenolysis, i.e. the replacement of a C−X bond by a C−H bond. Such reactions are
Dehalogenation
Organic compounds that contain sulfur
(HDS) in refineries, these compounds are removed as illustrated by the hydrogenolysis of thiophene: C4H4S + 8 H2 → C4H10 + H2S Compounds like allicin and
Organosulfur_chemistry
Chemical compound
yield the catalyst: Cu(NO3)2 + Ba(NO3)2 + (NH4)2CrO4 → CuCr2O4·BaCr2O4 Hydrogenolysis of ester compounds to the corresponding alcohols. This approach is useful
Copper_chromite
Concept involving selective reactions
include: Benzyl (Bn) protecting groups, which can often be removed by hydrogenolysis, while other acid- or base-sensitive groups remain intact. Silyl ether
Orthogonality_(chemistry)
Chemical reaction which breaks carbon-chlorine bonds via a reductant
chlorotrifluoroethene, CFC-12, HCFC-141b, and tetrachloroethene occur through hydrogenolysis. Reduction rates of CFC mirror theoretical rates calculated based on
Reductive_dechlorination
Chemical compound
ISBN 978-0-321-81139-4. Johnson, J. E.; Blizzard, R. H.; Carhart, H. W. (1948). "Hydrogenolysis of Alkyl Halides by Lithium Aluminum Hydride". Journal of the American
Lithium_aluminium_hydride
Chemical reaction removing oxygen atoms from a molecule
the replacement of an oxo group by two hydrogen atoms (A=O → AH2) are hydrogenolysis. Typical examples use metal catalysts and H2 as the reagent. Conditions
Deoxygenation
Chemical production of a pharmaceutical drug
replacement of the Cbz protective group by a BOC protective group in 7 (hydrogenolysis in the presence of di-tert-butyl dicarbonate) a carbonyl group is introduced
Oseltamivir_total_synthesis
Gasoline produced from biomass
dehydrogenation of alcohols/hydrogenation of carbonyls, deoxygenation reactions, hydrogenolysis and cyclization. The input for APR is a carbohydrate solution created
Biogasoline
Chemical process for converting alkenes to aldehydes
supporting organophosphorus ligands. Triphenylphosphine is subject to hydrogenolysis, releasing benzene and diphenylphosphine. The insertion of carbon monoxide
Hydroformylation
Pharmaceutical compound
from indole-3-oxalylchloride and benzyl cyclopropylamine with eventual hydrogenolysis of the benzyl group; mp 180–182. This compound, as with the 5-methoxy
N-Cyclopropyltryptamine
Chemical compound
mixture of the starting lactone and the silyl ether. The silyl ether on hydrogenolysis followed by Collins oxidation gave the aldehyde. Stereoselective preparation
Lovastatin
Environmental remediation technique
substratum. In ISCR, many reductive processes can take place. There are hydrogenolysis, β-elimination, hydrogenation, α-elimination, and electron transfer
In_situ_chemical_reduction
Chemical compound
(2) hydroxylated aromatics, or (3) hydroxylated quinones; the (4) hydrogenolysis of dibromocyclohexanetetrols; the (5) hydration of diepoxycyclohexanes;
1,2,4,5-Cyclohexanetetrol
Chemical compound
ethers. Like benzyl ethers, benzyloxymethyl ethers can be removed by hydrogenolysis with palladium on carbon or by Birch reduction. Like many alkylating
Benzyl_chloromethyl_ether
Chemical reaction
benzyl carbamate (3). The Cbz group of intermediate 3 is removed by hydrogenolysis to give an unsubstituted amide (4) and an aldehyde (5). The Bergmann
Bergmann_degradation
Sulfonyl group organic reaction
Julia, M (1983). "Organic Synthesis with Sulfones noXXIX Stereospecific hydrogenolysis of vinylic sulfones with grignards and transition metal catalysts".
Reductive_desulfonylation
Organic compound with an –S– group
thioethers are known, such as 1,4,7-trithiacyclononane. Sulfides undergo hydrogenolysis in the presence of certain metals: R-S-R' + 2 H2 → RH + R'H + H2S Raney
Organic_sulfide
Greek-American chemical engineer
Chen, D.G. Vlachos "Hydrogenation of ethylene and dehydrogenation and hydrogenolysis of ethane on Pt (111) and Pt (211): a density functional theory study"
Dionisios_Vlachos
Type of broad-spectrum antibiotic
tetracycline itself as a synthetic product. In 1955, Conover discovered that hydrogenolysis of aureomycin gives a deschloro product that is just as active as the
Tetracycline_antibiotics
Nanoparticle catalysts
catalysis between the two metals. Nanoparticle catalysts are active for the hydrogenolysis of C-Cl bonds such as polychlorinated biphenyls. Another reaction is
Nanomaterial-based_catalyst
German chemist (born 1980)
Agnieszka M Ruppert; Kamil Weinberg; Regina Palkovits (28 February 2012). "Hydrogenolysis goes bio: from carbohydrates and sugar alcohols to platform chemicals"
Regina_Palkovits
Class of chemical compounds
reduction of the aldehyde and silylation of the resulting alcohol. Hydrogenolysis of the benzyl ether gave the alcohol, which was oxidized under Swern
Epothilone
This protocol is a useful alternative to methods requiring acid or hydrogenolysis (e.g., Pd/C and hydrogen gas). Epoxides are generally attacked by alkoxyaluminium
Reductions with metal alkoxyaluminium hydrides
Reductions_with_metal_alkoxyaluminium_hydrides
Vegetable oil refining fuel production process
process. Chemically, it entails direct catalytic hydrodeoxygenation (hydrogenolysis) of plant oils, which are triglycerides, into the corresponding alkanes
Neste_Renewable_Diesel
American inorganic chemist
Richmond reported zirconium complexes that catalyze aromatic fluorocarbon hydrogenolysis. From 1996 to 1999, Kiplinger worked as a postdoctoral researcher at
Jaqueline_Kiplinger
Chemical compound
processing the ketone the desired cis,cis-alcohol was formed. After hydrogenolysis of the benzyloxycarbonyl group, dl-norchelidonine was synthesized. Chelidonine
Chelidonine
Technologies that relating to the production & use of hydrogen
Syngas Generation IV reactor Hydrogen bomb Dehydrogenation Hydrogenation Hydrogenolysis Hydrogen therapy Hydrogen odorant Atomic hydrogen welding Hydrogen-cooled
Hydrogen_technologies
Type of anaerobic respiration
substituents, while simultaneously adding electrons to the compound. Hydrogenolysis and vicinal reduction are the two known processes of this mechanism
Halorespiration
Group of chemical compounds
anhydride formation. The resulting depsipeptidate is reacted to achieve hydrogenolysis and acid-catalyzed deprotection with (b) H2, Pd/C, EtOAc (100%) and
Enniatin
Organic compounds containing the azide (N3) functional group
ligation or the Curtius rearrangement. Azides may be reduced to amines by hydrogenolysis or with a phosphine (e.g., triphenylphosphine) in the Staudinger reaction
Organic_azide
Chemical compound
At elevated temperature and in the presence of a palladium catalyst, hydrogenolysis of dihydrolevoglucosenone via levoglucosanol selectively yields tetrahydrofuran-2
Dihydrolevoglucosenone
Antibiotic medication
with SOCl2, and condensing it with 6-Aminopenicillanic acid (6-APA). Hydrogenolysis (Pd/C) completed the synthesis of ticarcillin. Fischer J, Ganellin CR
Ticarcillin
Hiyama coupling Hydration reaction Hydroamination Hydrodesulfurization Hydrogenolysis Hydrosilylation Hinsberg indole synthesis Hinsberg oxindole synthesis
List_of_organic_reactions
Chemical compound
hydrogenation (i.e. dihydrolevoglucosenone and levoglucosanol) and hydrogenolysis (i.e. tetrahydrofurandimethanol (THFDM) and 1,6-hexanediol). Levoglucosenone
Levoglucosenone
Catalyst composed of nickel and boron
except for benzylic, allylic and propargylic esters which are cleaved by hydrogenolysis: The NiCl2/NaBH4 system desulfurizes thioamides, thioethers, thioesters
Nickel_boride_catalyst
French chemist (born 1943)
Am. Chem. Soc, 110, 9, 1988, p. 2783-2787 Basset et al., « Catalytic Hydrogenolysis at Low Temperature and Pressure of Polyethylene and Polypropylene to
Jean-Marie_Basset
Chemical compound
18-electron acyl complex. The last step involves β-H elimination via hydrogenolysis which results in the cleavage of the aldehyde product and regeneration
Tris(triphenylphosphine)rhodium carbonyl hydride
Tris(triphenylphosphine)rhodium_carbonyl_hydride
American chemist
complete the synthesis of monensin in three additional steps. First, hydrogenolysis of the benzyl group afforded the free primary alcohol under standard
W._Clark_Still
Alkaloid
corresponding amino-alcohol, and the N-benzyl group finally removed by hydrogenolysis using palladium on carbon under an atmosphere of hydrogen gas at 31
Halostachine
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