Methods for purifying 5-(halomethyl)furfural
The present disclosure provides methods for purifying a 5-(halomethyl)furfural composition, including 5-(chloromethyl)furfural, at operating conditions that decrease or minimize the decomposition or degradation of 5-(chloromethyl)furfural during the process. The methods may employ certain solvents, operating conditions, and/or techniques (e.g., gas stripping). The gaseous 5-(halomethyl)furfural produced from the process can be condensed or deposited to yield 5-(halomethyl)furfural in liquid or solid form. The solid 5-(halomethyl)furfural may be amorphous or crystalline.
1. A method comprising boiling a mixture comprising 5-(halomethyl)furfural and solvent to produce gaseous 5-(halomethyl)furfural, wherein the solvent comprises:
(i) one or more alkyl phenyl solvents having at least one alkyl side chain of at least 10 carbon atoms; or
(ii) naphthenic oil, alkylated naphthalene, diphenyl, polychlorinated biphenyls, or polycyclic aromatic hydrocarbons; or
(iii) phenyl ethers,
wherein each of (i), (ii), and (iii) has a boiling point at or above the boiling point of the 5-(halomethyl)furfural,
or any combinations thereof.
2. The method of claim 1 , wherein the method is performed at an operating pressure of at least 20 torr.
3. The method of claim 2 , wherein the method is performed at an operating pressure of between 30 torr and 2000 torr.
4. The method of claim 1 , wherein the solvent comprises one or more alkyl phenyl solvents having at least one alkyl side chain of at least 10 carbon atoms.
5. The method of claim 1 , wherein the solvent comprises one or more alkyl phenyl solvents having at least one alkyl side chain of 10 to 20 carbon atoms.
6. The method of claim 1 , wherein the solvent comprises dodecylbenzene, diphenyl ether, anthracene, tetramethylnaphthalene, or any combinations thereof.
7. The method of claim 1 , further comprising condensing the gaseous 5-(halomethyl)furfural to obtain 5-(halomethyl)furfural in liquid form.
8. The method of claim 1 , further comprising depositing the gaseous 5-(halomethyl)furfural to obtain 5-(halomethyl)furfural in solid form.
9. The method of claim 1 , wherein the 5-(halomethyl)furfural is 5-(chloromethyl)furfural.
10. The method of claim 1 , wherein the 5-(halomethyl)furfural is provided in a 5-(halomethyl)furfural composition, and wherein the 5-(halomethyl)furfural composition has less than 5 wt % of acid.
11. The method of claim 1 , wherein the solvent comprises one or more alkyl phenyl solvents having at least one alkyl side chain having 10 to 13 carbon atoms.
12. The method of claim 1 , wherein the solvent comprises benzene substituted with C 10-13 alkyl chains, diphenylalkane having C 10-13 alkyl chains, dialkylbenzene having C 10-13 alkyl chains, linear alkyl benzene having C 10-13 side alkyl chains, or benzene substituted with C 13-30 alkyl chains, or any combinations thereof.
13. The method of claim 1 , wherein the solvent comprises dodecylbenzene.
14. The method of claim 1 , wherein the solvent comprises one or more branched alkyl phenyl solvents having at least one alkyl side chain of at least 10 carbon atoms.
15. The method of claim 1 , wherein the solvent comprises naphthenic oil, alkylated naphthalene, biphenyl, polychlorinated biphenyls, or polycyclic aromatic hydrocarbons, or any combinations thereof.
16. The method of claim 1 , wherein the solvent comprises anthracene, or tetramethylnaphthalene, or any combinations thereof.
17. The method of claim 1 , wherein the solvent comprises phenyl ethers.
18. The method of claim 1 , wherein the solvent comprises diphenyl ethers or polyphenyl ethers, or any combinations thereof.
19. The method of claim 1 , wherein the method is performed at an operating temperature of at least 60° C.
20. The method of claim 1 , wherein the method is performed at an operating temperature of between 60° C. and 400° C.