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Method for the preparation of 1.4-cyclohexane dicarboxylic acid dialkyl esters

A technology for dialkyl cyclohexanedicarboxylate and dialkyl terephthalate is applied in the field of preparing dialkyl 1,4-cyclohexanedicarboxylate, which can solve the problem of increasing the importance of alkyl esters, etc. question

Pending Publication Date: 2022-02-01
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, alkyl esters of cyclohexanedicarboxylates have also grown in importance in recent years, not least because of the controversy surrounding possible health concerns of phthalate-based plasticizers

Method used

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  • Method for the preparation of 1.4-cyclohexane dicarboxylic acid dialkyl esters
  • Method for the preparation of 1.4-cyclohexane dicarboxylic acid dialkyl esters
  • Method for the preparation of 1.4-cyclohexane dicarboxylic acid dialkyl esters

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0053] Example 1: Ring Hydrogenation of Diisononyl Terephthalate

[0054] To examine the duration dependence of diisononyl terephthalate ring hydrogenation, various DINT samples were tested in the ring hydrogenation. The following samples were used:

[0055] Sources of various DINT samples:

[0056] DINT-1

[0057] Take 2.318 g (16.1 mol) of isononyl alcohol (INA, Evonik, purity >99%), 1.358 g (7 mol) of dimethyl terephthalate (Oxxynova, purity >99.9%) and 2.4 g of tetra-n-butyl titanate Ester catalyst, placed in a 6L glass flask equipped with a stirrer, dip tube and a Raschig ring column connected to a condenser, heated to 240°C under a nitrogen atmosphere (nitrogen flow: 6L / h), while ensuring column headspace The distillate was discarded while the temperature did not rise above 65°C. The reaction process was monitored by gas chromatography, and the reaction was terminated once the residual concentration of methyl ester was <0.5%. After a reaction time of 3 hours, the bo...

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Abstract

The invention provides a process for preparing dialkyl 1,4-cyclohexanedicarboxylates by ring hydrogenation of the corresponding dialkyl terephthalate having a CO value of less than 0.3 mg KOH / g. The invention also provides for the use of the dialkyl 1,4-cyclohexanedicarboxylates thus produced as plasticizers or as a component of a plasticizer composition for plastics, in particular PVC.

Description

technical field [0001] The present invention relates to a process for the preparation of dialkyl 1,4-cyclohexanedicarboxylates by ring hydrogenation of the corresponding dialkyl terephthalates having a CO value of less than 0.3 mg KOH / g. The invention also provides the use of the resulting dialkyl 1,4-cyclohexanedicarboxylates as plasticizers or as components of plasticizer compositions in plastics, especially PVC. Background technique [0002] Plasticizers are used in many industries to make plastics such as polyvinyl chloride (PVC) softer and more pliable. Phthalates, the diesters of (phthalic acid), have been the main class of plasticizers for many years. However, alkyl esters of cyclohexanedicarboxylates have also grown in importance in recent years, not least because of the controversy surrounding possible health concerns of phthalate-based plasticizers. Here, dialkyl 1,2-cyclohexanedicarboxylates and more recently also dialkyl 1,4-cyclohexanedicarboxylates play a maj...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/303C07C69/75C08K5/12C08L27/06C09D7/63C09D7/20C09J11/06C09J11/00
CPCC07C67/283B01J21/06B01J21/00B01J23/38C09J2467/00C07C67/303C08K5/12C08L27/06C09D7/63C09D7/20C09J11/06C09J11/00C07C2601/14C07C69/75Y02P20/582C07C69/80C08K5/0016C09D5/00C09D7/40C07C2523/46B01J21/063B01J23/462C07C51/36
Inventor J·克拉夫特L·阿尔特曼J·安东M·格拉斯T·施奈德
Owner EVONIK OPERATIONS GMBH