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US 2019/0023678 A1Published application
Aromatic compounds from furanics
AssigneeNederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO
InventorsMarc CROCKATT, Jan Harm URBANUS
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Abstract
Described are methods for preparing phenols, benzene carboxylic acids, esters and anhydrides thereof from furanic compounds by reaction with a dienophile, wherein the furanic compounds are reacted with a hydrazine and/or oxime and then reacted with a dienophile.
Claims20
A method of preparing a compound having a backbone comprising formula (I):
- wherein:
- G is OH, CHO, CO2H, an ether, an ester, or an anhydride of a biomass-derived compound,
- the method comprising:
- (i) reacting a biomass-derived compound having a backbone comprising formula (II) with a compound of formula (III):
- wherein:
- X is O and z is 0, or
- X is N and z is 1,
- R1 is hydrocarbyl group, a heteroatom containing hydrocarbyl group, or a link to a heterogeneous support, and
- R2 is hydrogen, a hydrocarbyl group, a heteroatom containing hydrocarbyl group, or a link to a heterogeneous support,
- to give a compound with having a backbone structurc according to comprising formula (IV):
- (ii) reacting the compound having a backbone comprising formula (IV) with a dienophile to give a compound having a backbone comprising formula (V):
- (iii-a) hydrolyzing said compound having the backbone comprising formula (V) to yield the compound having the backbone comprising formula (I), wherein G is CHO, or
- (iii-b) optionally decarbonylating the product of step (iii-a) to provide the compound having the backbone comprising formula (I), wherein G is OH, or
- (iii-c) optionally oxidizing the product of step (ii), (iii-a), or a combination thereof to yield the compound having the backbone of formula (I), wherein G is CO2H, or
- (iii-d) converting the compound having the backbone comprising formula (I), wherein G is OH, CHO, or CO2H to the ether, ester, or anhydride thereof.
12 more elements
A method of preparing an aromatic compound, comprising:
- activating a furanic compound in an effluent from a catalytic dehydration of carbohydrates using a solid-supported hydrazine compound, solid-supported hydroxylamine compound, or a combination thereof, wherein the activating is performed in the absence of reducing the furanic compound, and
- reacting the activated furanic compound with a dienophile.
Dependencies are inferred from the claim text.