Catalyst containing a furan compound and use thereof in a hydroprocessing and/or hydrocracking method

Patent metadata

Field	Value
Publication number	US-2020391191-A1
Application number	US-201816765961-A
Country	US
Kind code	A1
Filing date	Nov 12, 2018
Priority date	Nov 22, 2017
Publication date	Dec 17, 2020
Grant date	—

Abstract

The invention relates to a catalyst comprising an alumina-, silica- or silica-alumina-based support, at least one group VIII element, at least one group VIB element, and a furan compound. The invention also relates to the method for producing said catalyst and to the use thereof in a hydrotreating and/ or hydrocracking method.

First claim

1 . A catalyst comprising a support based on alumina or silica or silica-alumina, at least one Group VIII element, at least one Group VIB element and a furan compound.

2 . The catalyst as claimed in claim 1 , in which the furan compound is of formula (I)

in which each of the radicals R1, R2, R3 and R4 is chosen from a hydrogen atom, a linear or branched or cyclic hydrocarbon-based radical including from 1 to 20 carbon atoms, a function from among: aldehyde —C(O)H, ketone —C(O)R 5 , carboxylic acid —COOH, ester —COOR 6 , hydroxymethyl —CH 2 OH, alkoxymethyl —CH 2 OR 7 , halomethyl —CH 2 X with X═Cl, Br or I, acyl halide —COX with X═Cl, Br or I, alcohol —OH, ether OR 8 , thiomethyl —CH 2 SH, (alkylsulfanyl)methyl —CH 2 SR 9 , thioester —COSR 10 with R 5 to R 10 representing a linear or branched or cyclic hydrocarbon-based radical of 1 to 20 carbon atoms, each of said radicals R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 possibly also including a heteroatom, a halogen and/or at least one function chosen from a hydroxyl function, an aldehyde function, a ketone function, a carboxylic function, an alkanoate function, a thiol function, an alkylsulfanyl function, a thioalkanoate function and an amine function.

3 . The catalyst as claimed in claim 2 , in which the radicals R3 and R4 represent, respectively, a hydrogen atom.

4 . The catalyst as claimed in claim 1 , in which the furan compound is chosen from 2-methylfuran, 2,5-dimethylfuran, furfuryl alcohol, 1-(2-furyl)ethanol, 2,5-bis(hydroxymethyl)furan, 5-(hydroxymethyl)furfural, 5-hydroxymethyl-2-furoic acid, 2-methoxyfuran, 2-furaldehyde, 5-methyl-2-furaldehyde, 5-(ethoxymethyl)furan-2-carboxaldehyde, 5-acetoxymethyl-2-furaldehyde, 5-chloromethylfurfural, 2,5-diformylfuran, 2-acetylfuran, 2-acetyl-5-methylfuran, furoic acid, 5-ethylfuroic acid, 5-formyl-2-furoic acid, 2,5-f urandicarboxylic acid, dimethyl 2,5-f urandicarboxylate, methyl 2-furoate, methyl 5-methyl-2-furoate, furfuryl acetate, furfuryl propionate, furfuryl mercaptan, 2-[(methylsulfanyl)methyl]furan, 2-furanmethanethiol formate, furfuryl thioacetate, furfuryl thiopropionate, methyl 2-thiofuroate, ethyl 3-(furfurylthio)propionate, furfurylamine, 2-furoyl chloride.

5 . The catalyst as claimed in claim 1 , in which the furan compound is a polyfuran compound of formula (II)

in which Z is chosen from an oxygen atom, a sulfur atom, a linear or branched or cyclic hydrocarbon-based radical including from 1 to 20 carbon atoms and which may also include a heteroatom, a halogen and/or at least one function chosen from a hydroxyl function, an aldehyde function, a ketone function, a carboxylic function, an alkanoate function, a thiol function, an alkylsulfanyl function, a thioalkanoate function and an amine function,
and in which each of the radicals R1 and R2 is chosen from a hydrogen atom, a linear or branched or cyclic hydrocarbon-based radical including from 1 to 20 carbon atoms, a function from among: aldehyde —C(O)H, ketone —C(O)R 5 , carboxylic acid —COOH, ester —COOR 6 , hydroxymethyl —CH 2 OH, alkoxymethyl —CH 2 OR 7 , halomethyl —CH 2 X with X═Cl, Br or I, acyl halide —COX with X═Cl, Br or I, alcohol —OH, ether OR 8 , thiomethyl —CH 2 SH, (alkylsulfanyl)methyl —CH 2 SR 9 , thioester —COSR 10 with R 5 to R 10 representing a linear or branched or cyclic hydrocarbon-based radical of 1 to 20 carbon atoms, each of said radicals R1, R2, R5, R6, R7, R8, R9 and R10 possibly also including a heteroatom, a halogen and/or at least one function chosen from a hydroxyl function, an aldehyde function, a ketone function, a carboxylic function, an alkanoate function, a thiol function, an alkylsulfanyl function, a thioalkanoate function and an amine function.

6 . The catalyst as claimed in claim 5 , in which the furan compound is chosen from bis(5-formylfurfuryl) ether, 2,2′-(thiodimethylene)difuran and 5,5-bis(5-methyl-2-furanyl)-2-pentanone.

7 . The catalyst as claimed in claim 1 , in which the content of Group VIB element is between 5% and 40% by weight expressed as Group VIB metal oxide relative to the total weight of the catalyst and the content of Group VIII element is between 1% and 10% by weight expressed as Group VIII metal oxide relative to the total weight of the catalyst.

8 . The catalyst as claimed in claim 1 , in which the mole ratio of Group VIII element to Group VIB element in the catalyst is between 0.1 and 0.8.

9 . The catalyst as claimed in claim 1 , which also contains phosphorus, the phosphorus content being between 0.1% and 20% by weight expressed as P 2 O 5 relative to the total weight of the catalyst and the mole ratio of phosphorus to the Group VIB element in the catalyst is greater than or equal to 0.05.

10 . The catalyst as claimed in claim 1 , in which the content of furan compound is between 1% and 45% by weight relative to the total weight of the catalyst.

11 . The catalyst as claimed in claim 1 , which also contains an organic compound other than the furan compound containing oxygen and/or nitrogen and/or sulfur.

12 . The catalyst as claimed in claim 11 , in which the organic compound is chosen from a compound including one or more chemical functions chosen from carboxylic, alcohol, thiol, thioether, sulfone, sulfoxide, ether, aldehyde, ketone, ester, carbonate, amine, nitrile, imide, oxime, urea and amide functions.

13 . The catalyst as claimed in claim 12 , in which the organic compound other than the furan compound is chosen from γ-valerolactone, 2-acetylbutyrolactone, triethylene glycol, diethylene glycol, ethylene glycol, ethylenediaminetetraacetic acid (EDTA), maleic acid, malonic acid, citric acid, γ-ketovaleric acid, dimethylformamide, N-methylpyrrolidone, propylene carbonate, 2-methoxyethyl 3-oxobutanoate, 2-methacryloyloxyethyl 3-oxobutanoate, bicine, tricine or a lactam.

14 . The catalyst as claimed in claim 1 , which is at least partially sulfurized.

15 . A process for preparing a catalyst as claimed in claim 1 , comprising the following steps:
a. a compound including a Group VIB element, at least one compound including a Group VIII element, furan compound and optionally phosphorus are placed in contact with a support based on alumina or silica or silica-alumina, or a regenerated catalyst containing a support based on alumina or silica or silica-alumina, at least one Group VIB element, at least one Group VIII element and optionally phosphorus are placed in contact with a furan compound, so as to obtain a catalyst precursor, b. said catalyst precursor derived from step a) is dried at a temperature below 200° C., without subsequently calcining it.

16 . A process for preparing a catalyst as claimed in claim 1 , comprising the following steps:
i) the furan compound is deposited on a support based on alumina or silica or silica-alumina by performing a step in which said support and the furan compound in liquid form are brought together simultaneously and without any physical contact between the support and the furan compound in liquid form, at a temperature below the boiling point of the furan compound and under pressure and time conditions such that a fraction of said furan compound is transferred in gaseous form to the support, ii) at least one compound including a Group VIB element, at least one compound including a Group VIII element, and optionally phosphorus are placed in contact with the support based on alumina or silica or silica-alumina,

Assignees

• Ifp Energies Now

Inventors

• Carrette Pierre Louis
• Delcroix Damien

Classifications

• C10G45/30

  characterised by the catalyst used · CPC title

• C10G45/08

  in combination with chromium, molybdenum, or tungsten metals, or compounds thereof · CPC title

• B01J37/28

  Phosphorising · CPC title

• B01J37/20

  Sulfiding · CPC title

• B01J37/02

  Impregnation, coating or precipitation ({B01J37/0009 and B01J37/0018 take precedence } ; protection by coating B01J33/00) · CPC title