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US 12,116,327 B2Granted
Selective hydroxyl group removal from alkylphenols
AssigneeNeste Oyj
InventorsMarina Lindblad, Kaisa Lamminpää, José Luis González Escobedo, Reetta Karinen, Eveliina Mäkelä, Riikka Puurunen
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Abstract
A process for selective removal of hydroxyl groups from phenolic compounds is disclosed. The process uses a combination of catalytic hydrodeoxygenation and catalytic direct deoxygenation to convert alkylphenols into alkylbenzenes.
Claims19
A process for removing hydroxyl groups from phenolic compounds, the process comprising:
- providing in a first reactor at least one hydrodeoxygenation catalyst containing sulphided NiMo, CoMo or NiW;
- providing a feedstock containing phenolic compounds;
- carrying out hydrodeoxygenation by contacting the feedstock with the hydrodeoxygenation catalyst to obtain a phenolic hydrocarbon feedstock;
- providing in a second reactor at least one direct deoxygenation catalyst containing Pt/Nb2O5;
- forming a mixture by feeding into the second reactor the phenolic hydrocarbon feedstock and hydrogen gas;
- and
- carrying out direct deoxygenation to the phenolic hydrocarbon feedstock to obtain hydrocarbons in the second reactor with the hydrogen gas included in the formed mixture during the direct deoxygenation, wherein the direct deoxygenation directly cleaves C—O bonds by hydrogenolysis and at least 50 mol-% of the hydroxyl groups originally bonded to phenolic compounds are removed while the aromaticity of the hydrocarbon is preserved.
4 more elements
A catalytic conversion system, comprising:
- a first reactor and a second reactor wherein:
- the first reactor is in fluid communication with the second reactor;
- wherein the first reactor includes:
- at least one catalyst bed comprising sulphided NiMo, CoMo, NiW or a combination thereof;
- temperature control system configured to monitor and adjust temperature inside the first reactor;
- at least one first inlet for feeding phenolic compounds into the first reactor;
- at least one second inlet for feeding hydrogen into the first reactor;
- the first reactor configured for hydrodeoxygenation by contacting the phenolic compounds with the hydrodeoxygenation catalyst to produce a phenolic hydrocarbon feedstock;
- at least one first outlet for transferring the produced phenolic hydrocarbon feedstock outside the first reactor to the second reactor;
- and
- wherein the second reactor includes:
- at least one direct deoxygenation catalyst bed containing Pt/Nb2O5 to carry out direct deoxygenation to the phenolic hydrocarbon feedstock received from the first reactor to obtain hydrocarbons while exposed to hydrogen gas in the second reactor during the direct deoxygenation, wherein the direct deoxygenation directly cleaves C—O bonds by hydrogenolysis and at least 50 mol-% of hydroxyl groups originally bonded to the phenolic compounds are removed while aromaticity of the hydrocarbons is preserved;
- temperature control system configured to monitor and adjust temperature inside the second reactor:
- at least one third inlet for feeding phenolic hydrocarbons into the second reactor;
- at least one fourth inlet for feeding the hydrogen gas into the second reactor;
- at least one second outlet for transferring a resulting feedstock contains aromatic compounds outside the second reactor;
- and
- wherein the second reactor optionally comprises at least one recycle feed line from the at least one second outlet to the at least one third inlet.
15 more elements
Dependencies are inferred from the claim text.