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Preparation method of di(2-propylheptyl) cyclohexyl-1,2-diformate

A dicarboxylic acid di-ester plasticizer technology, which is applied in the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of product coloring, low purity, low product yield, poor reaction selectivity, etc. problems, to achieve the effect of basically colorless appearance, no three waste pollution, high plasticizing performance and mechanical properties

Inactive Publication Date: 2015-04-01
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, when synthesizing cyclohexane-1,2-dicarboxylate bis(2-propylheptyl)ester, traditional strong acid catalysts such as concentrated sulfuric acid and sulfamic acid are used as esterification catalysts, the reaction selectivity is poor, and the product coloring and purity are not good. High; many side reactions, such as concentrated sulfuric acid as a catalyst, the problems that are prone to occur include: alcohol and alcohol intramolecular dehydration into alkene, intermolecular dehydration into ether, and sulfuric acid ester, resulting in dark color of the target product, and a large amount of activated carbon should be used for decolorization processing, and a large amount of activated carbon will adsorb the product, resulting in a decrease in the yield of the product; a large amount of waste liquid will be generated during the post-processing, which will cause serious environmental pollution; serious corrosion of the equipment will pose a safety hazard

Method used

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  • Preparation method of di(2-propylheptyl) cyclohexyl-1,2-diformate
  • Preparation method of di(2-propylheptyl) cyclohexyl-1,2-diformate

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Experimental program
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Effect test

Embodiment 1

[0020] Step 1 Esterification Reaction

[0021] Add 0.1mol (15.4g) of hexahydrophthalic anhydride and 2.8mol (44.3g) of 2-propylheptanol into a 250mL three-neck flask equipped with a magnetic stirrer, thermometer, reflux condenser, and water separator, and heat up to 100°C. Stir for 10 minutes until a transparent, uniform and stable liquid is formed. The measured acid value is 126.4mgKOH / g, then add 0.23g (1.49% of the anhydride content) catalyst tetrabutyl titanate into the three-necked flask, add 5mL of cyclohexane, and heat to The temperature is 200°C, heated to reflux and stirred, so that the water generated by the reaction is separated from the water separator, and the acid value is measured every 1 hour. The acid value is determined according to GB / T 1668-2008. After 4 hours of reaction, the acid value drops to 0.49mgKOH / g, the esterification rate is 99.62%, and the reaction is completed, and the product color is light yellow transparent liquid.

[0022] Purification of...

Embodiment 2

[0026] Step 1 Esterification Reaction

[0027] Add 0.1mol (15.4g) of hexahydrophthalic anhydride and 2.6mol (41.1g) of 2-propylheptanol into a 250mL three-neck flask equipped with a magnetic stirrer, thermometer, reflux condenser, and water separator, raise the temperature to 100°C, and magnetically Stir for 10 minutes until a transparent, uniform and stable liquid is formed. The measured acid value is 125.1mgKOH / g, then add 0.23g (1.49% of the anhydride content) catalyst tetrabutyl titanate into the three-necked flask, add 5mL of cyclohexane, and heat to The temperature is 200°C, heated to reflux and stirred, so that the water generated by the reaction is separated from the water separator, and the acid value is measured every 1 hour. The acid value is determined according to GB / T 1668-2008. After 5 hours of reaction, the acid value drops to 0.86mgKOH / g, the esterification rate is 99.31%, and the reaction is completed, and the product color is light yellow transparent liquid...

Embodiment 3

[0030] Step 1 Esterification Reaction

[0031] Add 0.1mol (15.4g) of hexahydrophthalic anhydride and 2.8mol (44.3g) of 2-propylheptanol into a 250mL three-neck flask equipped with a magnetic stirrer, thermometer, reflux condenser, and water separator, and heat up to 100°C. Stir for 10 minutes until a transparent, uniform and stable liquid is formed, and the measured acid value is 125.3 mgKOH / g, then add 0.15 g (1% of the anhydride content) of catalyst sodium bisulfate monohydrate into the three-necked flask, add 5 mL of cyclohexane, and heat to The temperature is 200°C, heated to reflux and stirred, so that the water generated by the reaction is separated from the water separator, and the acid value is measured every 1 hour. The acid value is determined according to GB / T 1668-2008. After 3 hours of reaction, the acid value drops to 0.40mgKOH / g, the esterification rate is 99.68%, and the reaction is completed, and the product color is a yellow transparent liquid.

[0032] Pur...

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Abstract

The invention relates to a preparation method of di(2-propylheptyl) cyclohexyl-1,2-diformate, belonging to the field of synthesis of fine chemical engineering products. The preparation method comprises the following steps: carrying out esterification reaction on hexahydrophthalic anhydride and 2-propyl heptanol by using non-protonic acid as a catalyst; and after the esterification reaction finishes, neutralizing, washing with water, dealcoholizing, and drying to obtain the di(2-propylheptyl) cyclohexyl-1,2-diformate, wherein the esterification rate is up to 99% above. The non-acid catalyst is a composite catalyst composed of tetrabutyl titanate, sodium bisulfate monohydrate or tetrabutyl titanate and sodium bisulfate monohydrate, and accounts for 0.2-4 wt% of the acid anhydride; the raw material alcohol / acid mole ratio is (2.2-3.0):1; the esterification reaction temperature is controlled at 140-230 DEG C, and the reaction time is 3-12 hours; and when the acid number is lower than 1mg KOH / g, the reaction is finished, thereby obtaining the product with nearly no color and higher esterification rate. The method has the advantages of high utilization ratio of the raw materials, high product quality, high efficiency and environment friendliness; and the di(2-propylheptyl) cyclohexyl-1,2-diformate is free of benzene ring structure, can be substituted for the phthalate-type novel environment-friendly plasticizer product, and has broad market prospects.

Description

technical field [0001] The invention discloses a preparation method of cyclohexane-1,2-dicarboxylate bis(2-propylheptyl) ester plasticizer, which belongs to the field of synthesis of fine chemical products. The present invention utilizes dibasic acid and higher carbon alcohol (C 10 ) reaction process, the product relates to the field of a PVC plasticizer preparation method, in particular to a preparation method of cyclohexane-1,2-dicarboxylate bis(2-propylheptyl) ester plasticizer. Background technique [0002] Plasticizers are functional chemical products that are added to high molecular polymers to increase plasticity, make them easy to process, and endow products with softness. Plasticizers are the most used types of plastic additives, among which phthalate plasticizers have always been the dominant type of plasticizers. However, in recent years, as people's research on its toxicity found that such plasticizers have the possibility of carcinogenicity, the European Union...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/75C07C67/08
CPCC07C67/08C07C2601/14C07C69/75
Inventor 蒋平平李志莹黄元旦王莹李晓婷
Owner JIANGNAN UNIV
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