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Hydroxypivalaldehyde production method

A technology of hydroxypivalaldehyde and its manufacturing method, which is applied to the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds. It can solve problems such as hindering hydrogenation and affecting the quality of SPG, and achieve the effect of improving the recovery rate.

Active Publication Date: 2018-08-28
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As shown in Patent Document 1 and the like, it is known that these impurities hinder hydrogenation during the production of NPG.
[0004] In addition, Patent Document 2 discloses that in the production of SPG, impurity aldehydes such as IBAL and FA contained in HPA affect the quality of SPG.

Method used

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  • Hydroxypivalaldehyde production method
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Examples

Experimental program
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Effect test

Embodiment

[0174] Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these Examples at all. However, in the following examples and comparative examples, unless otherwise specified, "parts" and "%" mean "parts by mass" and "% by mass", respectively.

[0175]Among them, in the examples, formaldehyde was quantified by absorbance measurement by the acetylacetone method, formate was quantified by capillary electrophoresis, and other components were quantified by gas chromatography. In addition, the amount of water in the extract oil layer was measured using a Karl-Fischer moisture meter (manufactured by Hiranuma Sangyo Co., Ltd., automatic moisture measuring device AQV-2200, and the titrant used HYDRANAL-Composite 5K manufactured by Hayashi Junyaku Kogyo Co., Ltd.) . Conditions for absorbance measurement, capillary electrophoresis, and gas chromatography are shown below.

[0176] [Measurement method and conditions]

[0177]

[0178] ...

reference example 1

[0203] Add 464g of IBAL (6.43mol) and 438g (5.83mol) of 40% formalin in a 2L three-necked flask with a stirring device and a cooler, and add 28g (0.277mol) of triethylamine as a catalyst while stirring , continue stirring at 90°C for 2 hours to synthesize HPA. After stirring, the HPA reaction liquid was returned to room temperature, and quantitative analysis of components was performed. Table 1 shows the composition of components in 930 g of the obtained HPA reaction liquid.

[0204] [Table 1]

[0205]

[0206]

[0207] Add 606.7 g of the HPA reaction solution obtained by the same method as Reference Example 1, 601.1 g of IBAL, and 401.93 g of pure water into a three-necked flask with a capacity of 2 L having a stirring device and a cooler, adjust the liquid temperature to 60° C., and stir 60 minutes. After you stop stirring, let it stand for about 10 minutes to allow it to separate into two layers. The upper layer was recovered to obtain 1017.5 g of an extract (oil l...

Embodiment 1

[0234] [Example 1: Continuous distillation]

[0235] The extract obtained by the same operation as in Reference Example 1 was mixed with water at a flow rate of 2.5 g / min and a flow rate of 3.0 g / min. There is steam with an absolute pressure of 0.6MPa in the pipe), and when the liquid is passed, the absolute pressure is 0.33MPa, and the residence time in the preheater is 10 minutes, and it is supplied to the The Dixon packing (Dixon packing) distillation column has a tower height of 500 mm, and the distillation tower has a tower diameter of 30 mm and a tower height of 800 mm. Here, the content of IBAL in the extract was 51.2% by mass, and the flow rate of IBAL was 1.28 g / min (0.512×2.5 g / min=1.28 g / min). In addition, the water content in the extract was 6.2% by mass, and the flow rate of water supplied from the extract was 0.155 g / min (0.062×2.5 g / min≒0.16 g / min). Therefore, the amount of water supplied for distillation is 247 parts by mass ((3.0+0.16)÷1.28×100≒247 with resp...

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Abstract

A hydroxypivalaldehyde (HPA) production method, comprising steps (i) to (iii) as mentioned below in this order, wherein the distillation step (iii) is a step of carrying out distillation in the co-presence of an extract and water, and the amount of water to be subjected to the distillation is 100 to 2,000 parts by mass inclusive relative to the total amount, i.e., 100 parts by mass, of isobutylaldehyde (IBAL) derived from the raw material in the extract to be subjected to the distillation and an aldehyde solvent represented by formula (1). A production method can be provided, whereby it becomes possible to produce HPA in a large amount and it also becomes possible to improve the rate of collection of HPA while selectively removing non-water impurities, particularly IBAL and the like, contained in HPA. According to the above-mentioned HPA production method, it also becomes possible to reduce the contents of specific impurities that are produced secondarily as by-products from HPA, i.e.,neopentyl glycol-isobutyric acid ester, isobutylaldehyde-hydroxypivalaldehyde-acetal and isobutylaldehyde-hydroxypivalaldehyde-aldol. Step (i): a reaction step of reacting IBAL with FA to produce a reaction solution containing HPA, step (ii): an extraction step of extracting the reaction solution with an aldehyde solvent represented by formula (1) under basic conditions to produce an extract containing HPA, and step (iii): a distillation / collection step of distilling the extract and then collecting HPA from the residue. (In formula (1), R represents a saturated alkyl group having 3 to 7 carbon atoms inclusive.)

Description

technical field [0001] The present invention relates to a kind of preparation method of hydroxy pivalaldehyde. Background technique [0002] Hydroxypivalaldehyde (hereinafter, HPA) is a raw material for neopentyl glycol (hereinafter, NPG), and HPA is also used as a reaction raw material for acetal compounds such as spirodiol (hereinafter, SPG). For example, NPG can be obtained by subjecting HPA to a hydrogenation reaction (hereinafter, hydrogenation). In addition, acetal compounds such as SPG can be obtained from HPA and polyols. NPG can be used as a raw material for alkyd resin coatings, polyester resins, and powder coatings. In addition to being used as an antioxidant, SPG can also be used as a raw material for high heat-resistant resins. [0003] In general, HPA can be obtained by the aldol reaction of isobutyraldehyde (hereinafter, IBAL) and formaldehyde (hereinafter, FA) under alkaline conditions. Patent Document 1 and the like disclose that in this case, HPA contai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/75C07C45/72C07C45/80C07C47/19C07C47/198
CPCC07C45/72C07C45/75C07C45/80C07C47/19C07C47/198C07C45/84C07C45/64C07C45/85C07C45/82C07C45/83C07C47/56
Inventor 佐藤由实山根正大
Owner MITSUBISHI GAS CHEM CO INC
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