Tricyclodecane dimethanol composition and preparation method of the same

Patent metadata

Field	Value
Publication number	US-2023192575-A1
Application number	US-202218003441-A
Country	US
Kind code	A1
Filing date	May 20, 2022
Priority date	Jun 4, 2021
Publication date	Jun 22, 2023
Grant date	—

Abstract

Provided are a tricyclodecane dimethanol composition which may be usefully applied to the preparation of a high heat resistant polyester by reducing the content of impurities, and a preparation method thereof.

First claim

What is claimed is:

1 . A tricyclodecane dimethanol composition comprising
tricyclodecane dimethanol, and an ether compound represented by the following Chemical Formula 1 in an amount of 1% by weight or less:
R—CH 2 —O—CH 2 —R   [Formula 1]

in Formula 1, R's are each independently

2 . The tricyclodecane dimethanol composition of claim 1 , comprising no ether compound.

3 . The tricyclodecane dimethanol composition of claim 1 , wherein a C 11-12 diol compound represented by the following Formula 2-1 or Formula 2-2 is included in an amount of 3% by weight or less:

in Formula 2-1,
R′ 1 and R′ 2 are each independently hydrogen or methyl, provided that none of R′ 1 and R′ 2 is methyl,

in Formula 2-2,
n is 3 or 4,
when n is 3, R′ 3 is hydrogen or methyl, and
when n is 4, R′ 3 is hydrogen.

4 . A method of preparing a tricyclodecane dimethanol composition comprising
tricyclodecane dimethanol, and an ether compound represented by the following Chemical Formula 1 in an amount of 1% by weight or less, the method comprising the following steps of ii), iii), iv), and vi), and further comprising one or more of the following steps of i) and v): i) purifying dicyclopentadiene by performing the retro Diels-Alder reaction and the Diels-Alder reaction of dicyclopentadiene; ii) performing a hydroformylation reaction by introducing a catalyst composition including a rhodium-containing catalyst compound and an organophosphorus compound into a reactor, and by adding dropwise dicyclopentadiene under a mixed gas of hydrogen and carbon monoxide; iii) performing a hydrogenation reaction of the reaction mixture obtained after the step ii) in the presence of a hydrogenation catalyst; iv) removing the hydrogenation catalyst and the solvent from the reaction mixture obtained after the step iii); v) performing thin film evaporation of the reaction mixture obtained after the step iv); and vi) performing vacuum fractional distillation of the reaction mixture obtained after the step iv) or the step v):
R—CH 2 —O—CH 2 —R   [Formula 1]

in Formula 1, R's are each independently

5 . The method of claim 4 , wherein the step i) includes the step of performing the retro Diels-Alder reaction by adding dropwise dicyclopentadiene to a reactor which contains an organic solvent and is maintained at 150° C. to 250° C.; and the step of reacting the cyclopentadiene monomer obtained by the retro Diels-Alder reaction at a temperature of 10° C. to 30° C. to obtain purified dicyclopentadiene.

6 . The method of claim 4 , wherein, after the step i), the content of co-dimers of C 4-5 diene of dicyclopentadiene and cyclopentadiene is 2% by weight or less.

7 . The method of claim 4 , wherein, in the step ii), the reaction pressure is 20 bar to 150 bar and the reaction temperature is 50° C. to 100° C.

8 . The method of claim 4 , wherein the organophosphorus compound is included in an amount of 5 moles to 200 moles per 1 mole of rhodium.

9 . The method of claim 4 , wherein, in the step ii), the dropwise addition of dicyclopentadiene is performed such that the number of moles of dicyclopentadiene added per minute with respect to 1 mmol of the rhodium element in the catalyst composition is 10 mmol to 10,000 mmol.

10 . The method of claim 4 , wherein the hydrogenation catalyst of the step iii) is a Ru/C catalyst.

11 . The method of claim 4 , wherein the hydrogenation reaction of the step iii) is performed at a temperature of 80° C. to 250° C. and a pressure of 20 bar to 200 bar.

12 . The method of claim 4 , wherein the thin film evaporation of the step v) is performed at a temperature of 100° C. to 200° C. and a pressure of 1 mtorr to 20 mtorr.

Assignees

• Sk Chemicals Co Ltd

Inventors

• Chae Hee Il
• Kang Ju-Sik
• Park Jeong Ho
• Lee Song
• Chang Yu Mi

Classifications

• C07C7/177 Primary

  by selective oligomerisation or polymerisation of at least one compound of the mixture · CPC title

• C07C29/84

  by extractive distillation · CPC title

• C08G63/16

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G63/85

  Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• B01J23/462

  Ruthenium · CPC title