Tricyclodecane dimethanol composition and preparation method of the same

Patent metadata

Field	Value
Publication number	US-11964932-B2
Application number	US-202218003432-A
Country	US
Kind code	B2
Filing date	May 20, 2022
Priority date	Jun 18, 2021
Publication date	Apr 23, 2024
Grant date	Apr 23, 2024

Abstract

Provided are a tricyclodecane dimethanol composition, in which a ratio of structural isomers is controlled, and a preparation method thereof.

First claim

What is claimed is:

1. A method of preparing a tricyclodecane dimethanol composition, the method comprising the steps of:
performing a two-step hydroformylation reaction by:
a) adding dropwise dicyclopentadiene at a temperature of 75° C. to 85° C. while maintaining a mixed gas of hydrogen and carbon monoxide at a pressure 20 bar to 150 bar in the presence of a catalyst composition including a rhodium-containing catalyst compound and 5 moles to 200 moles of an organophosphorus compound per 1 mole of rhodium, and a dienophile to form a reaction mixture; and
b) after the dropwise addition of dicyclopentadiene is finished, further reacting the reaction mixture while heating the reaction mixture to 130° C. and maintaining the pressure of the CO/H 2 mixed gas;

wherein the method further comprises the steps of:
performing a hydrogenation reaction of tricyclodecane dialdehyde obtained by the two-step hydroformylation reaction in the presence of a hydrogenation catalyst,
wherein the tricyclodecane dimethanol composition includes 20 parts by weight to 35 parts by weight of a first structural isomer represented by the following Formula 1-1, 27 parts by weight to 42 parts by weight of a second structural isomer represented by the following Formula 1-2, and 27 parts by weight to 42 parts by weight of a third structural isomer represented by the following Formula 1-3, based on 100 parts by weight of the composition:

2. The method of claim 1 , wherein the organophosphorus compound is included in an amount of 10 moles to 100 moles per 1 mole of rhodium.

3. The method of claim 1 , wherein in a step of the two-step hydroformylation reaction, 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.

4. The method of claim 1 , wherein the dienophile is one or more selected from the group consisting of maleic anhydride, tetracyanoethylene, maleic acid, maleonitrile, 2-methylenemalononitrile, dialkyl 2-methylenemalonate, 2-methylenemalonic acid, 2-methylenemalonaldehyde, 3-methylenepentane-2,4-dione, fumaraldehyde, ethene-1,1,2,2-tetracarbaldehyde, 1,4-benzoquinone, and dialkyl maleate.

5. The method of claim 1 , wherein the dienophile is used in an amount of 0.001 part by weight to 1.0 part by weight, based on 100 parts by weight of the dicyclopentadiene.

6. The method of claim 1 , wherein the hydrogenation catalyst is a Ru/C catalyst.

7. The method of claim 1 , wherein the hydrogenation reaction is performed at a temperature of 80° C. to 250° C. and a pressure of 20 bar to 200 bar.

Assignees

• Sk Chemicals Co Ltd

Inventors

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

Classifications

• C07C31/278 Primary

  Polycyclic with condensed rings · CPC title

• B01J31/2213

  At least two complexing oxygen atoms present in an at least bidentate or bridging ligand · CPC title

• C07C29/141

  with hydrogen or hydrogen-containing gases · CPC title

• C07C45/50 Primary

  by oxo-reactions · CPC title

• C08G63/199

  Acids or hydroxy compounds containing cycloaliphatic rings · CPC title