Production of substituted phenylene aromatic diesters

A technology of phenylene dibenzoate and methyl catechol, which is applied in the field of preparation of phenylene aromatic diesters, can solve problems such as difficult to obtain, unreliable, and limited commercial supply, and achieve simplified preparation Effect

Inactive Publication Date: 2014-02-05
WR GRACE & CO CONN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, commercial supplies of BMC are limited, unreliable, and difficult to obtain

Method used

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  • Production of substituted phenylene aromatic diesters
  • Production of substituted phenylene aromatic diesters
  • Production of substituted phenylene aromatic diesters

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preparation example Construction

[0027] The present disclosure relates to the preparation of substituted phenylene aromatic diesters. The compound 5-tert-butyl-3-methylcatechol (or "BMC") has been found to be useful in the preparation of substituted phenylene aromatic diesters, 5-tert-butyl-3-methyl-1, A potent precursor of 2-phenylene dibenzoate (or "BMPD"). BMPDs are efficient internal electron donors in Ziegler-Natta catalysts. The methods disclosed in the present invention advantageously provide an economical (time, energy, productivity, and / or starting reagent economy), simple, scalable synthetic route to BMCs with yields comparable to its Acceptable for commercial / industrial applications. Thus, the reliable preparation of BMC contributes to the reliable and economical preparation of 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate (BMPD), which in turn contributes to Olefin-based polymers, especially propylene-based polymers, are prepared with improved properties.

[0028] 1. Preparation of BMC / BMPD f...

Embodiment

[0109] Preparation of 2-methoxy-6-methylphenol by hydrogenation of o-vanillin

[0110] Due to the use of hydrogen gas, the reaction was carried out in a drybox for safety measures. During the procedure, the moisture-proof box was periodically purged with nitrogen to ensure that there was no accumulation of hydrogen. An adapter with a balloon on one end was attached to a 250 mL flask with a side arm and a magnetic stir bar. 1 g of Pd on carbon (5% Pd) was slowly added to the flask. Subsequently, 7.6 g of o-vanillin and 100 ml of methanol were added. Hydrogen was introduced into the flask system through the side arm until the balloon inflated to a volume of approximately 250 ml. The reaction was stirred at room temperature for 3 days. Hydrogen is added as the balloon shrinks due to reaction and diffusion. GC samples were taken to monitor the reaction. When completion of the reaction was evidenced by the appearance of intermediates first followed by products, the gas in the...

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Abstract

Synthesis pathways for a precursor to 5-tert-butyl-3-methyl-1, 2-phenylene dibenzoate are provided. The precursor is methylcatechol and / or 5-tert-butyl-3-methylcatechol.

Description

Background technique [0001] The present disclosure relates to the preparation of substituted phenylene aromatic diesters. [0002] Substituted phenylene aromatic diesters are useful as internal electron donors in the preparation of procatalyst compositions for the preparation of olefin-based polymers. Specifically, a Ziegler-Natta catalyst containing 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate as an internal electron donor showed high catalytic activity and high selectivity. These catalysts produce olefin-based polymers (eg, propylene-based polymers) with high isotacticity and broad molecular weight distribution. [0003] 5-tert-butyl-3-methylcatechol (or "BMC") is known as a useful method for the preparation of 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate ( or "BMPD"). However, commercial supplies of BMC are limited, unreliable, and difficult to obtain. Therefore, the prior art requires additional sources and / or additional synthetic steps for a reliable, continuous,...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/017
CPCC07C37/02C07C41/30C07C37/62C07C37/055C07C67/08C07C67/14C07C37/002C07C41/18C07C45/515C07C41/09C07C41/16C07C41/22C07C41/26C07C69/78C07C39/08C07C39/27C07C43/205C07C43/225C07C43/23C07C47/565B01J19/24C07C69/017
Inventor 陈林枫T.W.梁高宽强陶涛
Owner WR GRACE & CO CONN
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