Tricyclodecane dimethanol composition and preparation method of the same

Patent metadata

Field	Value
Publication number	US-11891354-B2
Application number	US-202218003445-A
Country	US
Kind code	B2
Filing date	May 20, 2022
Priority date	Jun 4, 2021
Publication date	Feb 6, 2024
Grant date	Feb 6, 2024

Abstract

Provided are a tricyclodecane dimethanol composition which may be suitably used in preparing a polyester resin exhibiting excellent solvent resistance and chemical resistance when forming a coating film and having excellent solubility in organic solvents or water, and a preparation method thereof.

First claim

What is claimed is:

1. A composition comprising tricyclodecane dimethanol; and
one or more of C11-12 diol compounds represented by the following Formula 1-1 and Formula 1-2,
wherein the total content of the C11-12 diol compounds is 10% by weight to 20% by weight:

in Formula 1-1,
R1 and R2 are each independently hydrogen or methyl, provided that both R1 and R2 being methyl is excluded,

in Formula 1-2,
n is 3 or 4,
when n is 3, R3 is hydrogen or methyl, and
when n is 4, R3 is hydrogen.

2. The composition of claim 1 , wherein the C11-12 diol compound is one or more selected from the group consisting of the following compounds:

3. The composition of claim 1 , wherein the tricyclodecane is included in an amount of 79% or more, based on the total weight of the composition.

4. A method of preparing a composition comprising tricyclodecane dimethanol; one or more of C11-12 diol compounds represented by the following Formula 1-1 and Formula 1-2, wherein the total content of the C11-12 diol compounds is 10% by weight to 20% by weight, the method comprising the steps of:
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; and
performing a hydrogenation reaction of tricyclodecane dialdehyde obtained by the hydroformylation reaction in the presence of a hydrogenation catalyst,
wherein the dicyclopentadiene includes 4% by weight to 20% by weight of co-dimers of C4-5 diene and cyclopentadiene:

in Formula 1-1,
R1 and R2 are each independently hydrogen or methyl, provided that both R1 and R2 being methyl is excluded,

in Formula 1-2,
n is 3 or 4,
when n is 3, R3 is hydrogen or methyl, and
when n is 4, R3 is hydrogen.

5. The method of claim 4 , wherein the C4-5 diene is butadiene, piperylene, or isoprene.

6. The method of claim 4 , wherein a pressure of the hydroformylation reaction step is 20 bar to 150 bar.

7. The method of claim 4 , wherein a temperature of the hydroformylation reaction step 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 hydroformylation reaction step, 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 is a Ru/C catalyst.

11. The method of claim 4 , wherein the hydrogenation reaction is performed at a temperature of 80 ° C. to 150 ° C. and a pressure of 50 bar to 100 bar.

Assignees

• Sk Chemicals Co Ltd

Inventors

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

Classifications

• C07C29/158 Primary

  containing rhodium or compounds thereof · CPC title

• C07C31/278

  Polycyclic with condensed rings · CPC title

• C07C45/50 Primary

  by oxo-reactions · CPC title

• C08G63/183

  Terephthalic acids · CPC title

• C09D7/20

  Diluents or solvents · CPC title