Process for preparing dioxolane

Patent metadata

Field	Value
Publication number	US-11655228-B2
Application number	US-201917056741-A
Country	US
Kind code	B2
Filing date	May 8, 2019
Priority date	May 18, 2018
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

The present invention relates to a process for preparing dioxolane by reacting ethylene glycol with an aqueous solution of formaldehyde in the presence of an acid catalyst. The raw product comprising water, dioxolane and methanol is fed to a phase separation unit (20) wherein an organic extracting agent is present. An organic fraction stream from the phase separation unit is transferred to an upper part of a purification column (30) from which dioxolane is withdrawn as a bottom product while the distillate stream of the purification column is recycled to the phase separation unit. An aqueous fraction stream from the phase separation unit is transferred to a waste water column (40), withdrawing a waste water stream from the bottom of the waste water column, withdrawing a side stream (42) from a stage between the feed stage and the reflux stage of the waste water column and recycling this stream (42) to the phase separation unit, and withdrawing a distillate stream (43) containing methanol from the waste water column.

First claim

The invention claimed is:

1. A process for preparing dioxolane comprising the steps of
a) feeding a first feed stream ( 1 ) containing ethylene glycol and a second feed stream ( 2 ) containing formaldehyde and methanol in aqueous solution to a reaction distillation device ( 10 ) and reacting ethylene glycol and formaldehyde in aqueous solution in the presence of at least one catalyst to obtain a raw product which comprises water, dioxolane and methanol,
b) transferring a distillate stream ( 11 ) containing raw product from the top of the reaction distillation device ( 10 ) to a phase separation unit ( 20 ), wherein an organic extracting agent is present in the phase separation unit ( 20 ), wherein the mass fraction of methanol in the distillate stream ( 11 ) from the reaction distillation device ( 10 ) is from 0.02% to 5%,
c) transferring an organic fraction stream ( 21 ) from the phase separation unit ( 20 ) to an upper part of a purification column ( 30 ), withdrawing a bottom product stream ( 31 ) containing dioxolane from the purification column ( 30 ), and recycling a distillate stream ( 32 ) from the purification column ( 30 ) to the phase separation unit ( 20 ), wherein the mass fraction of methanol in the bottom product stream ( 31 ) of the purification column ( 30 ) is less than 0.5%,
d) transferring an aqueous fraction stream ( 22 ) from the phase separation unit ( 20 ) to a waste water column ( 40 ), withdrawing a waste water stream ( 41 ) from the bottom of the waste water column ( 40 ), withdrawing a side stream ( 42 ) from a stage between the feed stage and the reflux stage of the waste water column ( 40 ) and recycling this stream ( 42 ) to the phase separation unit ( 20 ), and withdrawing a distillate stream ( 43 ) containing methanol from the waste water column ( 40 ).

2. The process according to claim 1 , wherein a side stream ( 44 ) containing methanol is withdrawn from a stage below the feed stage of the waste water column ( 40 ).

3. The process according to claim 1 , wherein an additional water containing stream ( 23 ) is fed to the phase separation unit ( 20 ).

4. The process according to claim 1 , wherein the extracting agent is selected from the group consisting of pentane, cyclopentane, 2,2-dimethylbutane, 2,3-dimethylbutane, methylisobutylether, 2-methylpentane, 3-methylpentane, propylisopropylether, hexane, methylcyclopentane, 2,2-dimethylpentane, 2,4-dimethylpentane, cyclohexane, 3,3-dimethylpentane, 2-ethyl-3-methyl-1-butene, 1,1-dimethylcyclopentane, 2-methylhexane, di-n-propylether, (z)-1,3-dimethylcyclopentane, trans-1,2-dimethylcyclopentane, trans-1,3-dimethylcyclopentane, 3-methyl-hexane, 1-ethoxybutane, 3-ethylpentane, 2,2,4-trimethylpentane, n-heptane, isopropyl-isobutyl-ether, (z)-1,2-dimethylcyclopentane, 2,2-dimethylhexane, 2,3-dimethylhexane, 2,4-dimethylhexane, 2,5-dimethylhexane, 3,4-dimethylhexane, 2-methylheptane, and octane.

5. The process according to claim 1 , wherein the extracting agent is selected from the group consisting of isomers of hexane (C 6 H 14 ).

6. The process according to claim 1 , wherein the extracting agent comprises n-hexane with a mass fraction of at least 80%.

7. The process according to claim 1 , wherein a make-up stream ( 24 ) containing the organic extracting agent is fed to the phase separation unit ( 20 ).

8. The process according to claim 1 , wherein the phase separation unit ( 20 ) comprises a mixer ( 25 ) and a phase separator ( 26 ), the distillate stream ( 11 ) from the reaction distillation device ( 10 ), the distillate stream ( 32 ) from the purification column ( 30 ), the side stream ( 42 ) from the waste water column ( 40 ) and optionally the additional water containing stream ( 23 ) and/or the make-up stream ( 24 ) containing the organic extracting agent being fed to and mixed in the mixer ( 25 ), and the outlet stream of the mixer ( 25 ) being fed to the phase separator ( 26 ).

9. The process according to claim 1 , wherein the mass fraction of methanol in the bottom product stream ( 31 ) of the purification column ( 30 ) is less than 0.1%.

Assignees

• Basf Se
• Kolon Plastics Inc

Inventors

• Heitz Thomas
• Kramp Marvin
• Heilig Manfred
• Chang Hyunsoo
• Kim Jongmoon
• Cho In Gi

Classifications

• C07D317/12 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• Y02P20/10

  Process efficiency · CPC title