Method for producing diol having cyclic acetal skeleton

Patent metadata

Field	Value
Publication number	US-10370384-B2
Application number	US-201716078292-A
Country	US
Kind code	B2
Filing date	Mar 9, 2017
Priority date	Mar 15, 2016
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

The present invention provides a method for producing a diol having a cyclic acetal skeleton, in which the method include an acetalization reaction step of obtaining a diol having a cyclic acetal skeleton by subjecting raw material hydroxypivalaldehyde and at least pentaerythritol and/or trimethylolpropane to an acetalization reaction under an acid catalyst and the raw material hydroxypivalaldehyde can contain a prescribed amount of at least one impurity selected from the group consisting of formaldehyde, neopentyl glycol, an ester compound having a neopentyl glycol skeleton represented by formula (III), and isobutyraldehyde.

First claim

The invention claimed is:

1. A method for producing a diol having a cyclic acetal skeleton, the method comprising:
conducting a first acetalization reaction of a raw material hydroxypivalaldehyde and at least pentaerythritol and/or trimethylolpropane under an acid catalyst, to obtain a reaction solution comprising the diol having the cyclic acetal skeleton;
separating the diol having the cyclic acetal skeleton, which is precipitated in the reaction solution, to obtain a reaction mother liquor; and
conducting a second acetalization reaction of a rain material hydroxypivalaldehyde and at least pentaerythritol and/or trimethylolpropane under the reaction mother liquor and an acid catalyst, to obtain the diol having the cyclic acetal skeleton,
wherein the separating and the second acetalization reaction are conducted more than once,
wherein the raw material hydroxypivalaldehyde comprises an impurity selected from the group consisting of formaldehyde, neopentyl glycol, isobutyraldehyde and an ester compound having a neopentyl glycol skeleton of formula (III):

 wherein R represents a hydrocarbon group having 1 to 4 carbon atoms, a hydrocarbon group having a hydroxy group and having 1 to 4 carbon atoms, or a hydrogen atom, and
wherein when the impurity comprises the formaldehyde, a content of the formaldehyde is 0.80% by mass or less;
when the impurity comprises the neopentyl glycol and/or the ester compound, a total molar concentration of the neopentyl glycol and/or the ester compound is 0.100 mol/kg or less; and
when the impurity comprises the isobutyraldehyde, a content of the isobutyraldehyde is 0.05% by mass or less,
all based on 100% by mass of the raw material hydroxypivalaldehyde.

2. The method according to claim 1 , wherein the diol obtained by the second acetalization reaction comprises, as an impurity, a dioxane triol monoformal of formula (I) in an amount of 004 area % or less, expressed as an area fractional concentration based on a sum of components having a relative retention time of 1.45 or less in a gas chromatography analysis performed under prescribed conditions in which the relative retention time of the diol is 1.00:

3. The method according to claim 1 , wherein the diol obtained by the second acetalization reaction comprises, as an impurity, a hydroxypivalaldehyde neopentyl glycol acetal of formula (II) in an amount of 0.19 area % or less, expressed as an area fractional concentration based on a sum of components having a relative retention time of 1.45 or less in a gas chromatography analysis performed under prescribed conditions in which the relative retention time of the diol is 1.00:

4. The method according to claim 1 , wherein the diol obtained by the second acetalization reaction comprises, as an impurity, a spiro monoalcohol of formula (IV) in an amount of 0.15 area % or less, expressed as an area fractional concentration based on a sum of components having a relative retention time of 1.45 or less in a gas chromatography analysis performed under prescribed conditions in which the relative retention time of the diol is 1.00:

5. The method according to claim 1 , wherein the ester compound comprises
an isobutyric acid neopentyl glycol monoester of formula (V):

 and/or
a hydroxypivalic acid neopentyl glycol monoester of formula (VI):

6. The method according to claim 1 , wherein the diol is spiroglycol and/or dioxane glycol.

7. The method according to claim 1 , the method further comprising:
conducting an aldol condensation reaction for forming crude hydroxypivalaldehyde by an aldol condensation reaction of formaldehyde and isobutyraldehyde.

8. The method according to claim 7 , the method further comprising, at least any one of:
extracting the raw material hydroxypivalaldehyde by adding water and/or an organic solvent to the crude hydroxypivalaldehyde;
distilling the crude hydroxypivalaldehyde to collect the raw material hydroxypivalaldehyde as a distillate; and
crystallizing the raw material hydroxypivalaldehyde by adding water and/or an organic solvent to the crude hydroxypivalaldehyde and collecting the raw material hydroxypivalaldehyde by solid-liquid separation.

9. The method according to claim 1 , wherein a reaction temperature employed during the acetalization reaction is from 40° C. to 105° C.,
wherein a pH value of a reaction solution during the acetalization reaction is from 0.1 to 4.0, and
wherein after the first acetalization reaction, 30 to 98% by mass of the reaction mother liquor is reused to perform the second acetalization reaction.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Yamane Masahiro

Classifications

• C07C45/79

  by solid-liquid treatment; by chemisorption · CPC title

• C07C45/80

  by liquid-liquid treatment · CPC title

• C07D319/06 Primary

  not condensed with other rings · CPC title

• C07D493/10 Primary

  Spiro-condensed systems · CPC title

• C07C45/45

  by condensation · CPC title