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Preparation method of tris (2-hydroxyethyl) isocyanurate

A technology of isocyanurate and hydroxyethyl, applied in the field of preparation of triisocyanurate, can solve the problems of affecting product purity, unstable yield, narrow operating window, etc., and achieve reaction yield and crude product purity Simplify, improve product yield and purity, and reduce the effects of polymerization side reactions

Pending Publication Date: 2022-03-08
JIAHUA CHEM TECH DEV SHANGHAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Alkaline substances produced by DMF self-decomposition can also trigger EO self-polymerization, resulting in unstable yield, poor stability of process batches, and narrow operating window
There are also researchers who use alcohol ether series solvents such as ethylene glycol monomethyl ether, and the pure product yield is 70-85%, and the acetone-water solvent system has a yield of 82%. After testing and analysis, alcohol ether solvents such as ethylene glycol When monomethyl ether, ethylene glycol, methanol, ethanol, etc. are used as reaction solvents, the oligomers formed by ring opening of alcohol ether itself and EO are detected in the system, resulting in the yield of such systems being generally lower than that of DMF systems, and such systems A large number of polyether by-products affect the purity of the product, and a careful purification process is required to obtain high-purity Cyc

Method used

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  • Preparation method of tris (2-hydroxyethyl) isocyanurate
  • Preparation method of tris (2-hydroxyethyl) isocyanurate
  • Preparation method of tris (2-hydroxyethyl) isocyanurate

Examples

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Effect test

Embodiment 1

[0026] The present embodiment provides a kind of preparation method of three (2-hydroxyethyl) isocyanurate, comprises the steps:

[0027] 412gN,N-dimethylacetamide, 100g cyanuric acid (purity 98%), 0.5g dimethylamine and 1.2g BF 3 ·Et 2 O(BF 3 content is 46.5wt%) into a 3L reactor, heated up to 110°C, then pumped 108g of ethylene oxide into the reaction by the feeding pump, controlled the reaction temperature to 110°C, and the reaction time was 2h. After the reaction, the reaction liquid Cool down to 30°C, remove N,N-dimethylacetamide by distillation under reduced pressure to obtain 257 g of a wet crude product of tris(2-hydroxyethyl)isocyanurate; then add 500 mL of acetone to the wet crude product and stir at room temperature Filter and dry after 0.5 hour to get three (2-hydroxyethyl) isocyanurate 186g, yield 92%, this three (2-hydroxyethyl) isocyanurate product is analyzed its purity through high performance liquid chromatography 94%.

Embodiment 2

[0029] The present embodiment provides a kind of preparation method of three (2-hydroxyethyl) isocyanurate, comprises the steps:

[0030] Add 380g of pyridine and 100g of cyanuric acid (purity 98%) into a 3L reactor, raise the temperature to 110°C, then pump 115g of ethylene oxide into the reaction by the feeding pump, control the reaction temperature to 110°C, and the reaction time to 2.5h , after the reaction, the reaction solution was cooled to 35° C., and pyridine was removed by distillation under reduced pressure to obtain 264 g of a wet crude product of tris (2-hydroxyethyl) isocyanurate. Then, 500 mL of acetone was added to the wet crude product, and stirred at room temperature for 0.5 After hours, filter and dry to get three (2-hydroxyethyl) isocyanurate 192g, yield 95%, and this three (2-hydroxyethyl) isocyanurate product is analyzed by high performance liquid chromatography and its purity is 90%.

Embodiment 3

[0032] The present embodiment provides a kind of preparation method of three (2-hydroxyethyl) isocyanurate, comprises the steps:

[0033] 2027g N-methylpyrrolidone, 1006g cyanuric acid (98% purity), 5g Cs 2 CO 3 and 6g BF 3 ·Et 2 O(BF 3 content is 46.5wt%) into a 20L reactor, heated up to 110°C, then pumped 1091g of ethylene oxide into the reaction by feeding pump, controlled reaction temperature was 110°C, and reaction time was 1.5h. Cool the liquid to 40°C, discharge it into a 50L three-in-one equipment, add 8580g of acetonitrile, stir at 60°C for 0.5 hours, then cool down to 10°C, filter and dry in the three-in-one equipment to obtain tris(2-hydroxyethyl)iso Cyanurate 1927g, yield 95%, this tris (2-hydroxyethyl) isocyanurate product is analyzed by high performance liquid chromatography and its purity is 93%.

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of tris (2-hydroxyethyl) isocyanurate, which comprises the following steps: reacting cyanuric acid and ethylene oxide in the presence of a catalyst I, a catalyst II and a solvent to obtain the tris (2-hydroxyethyl) isocyanurate, one of the key catalysts is a hard acid (based on the theory of soft and hard acids and bases), and the addition amount of the hard acid accounts for 0-3% of the mass of cyanuric acid. The preparation method provided by the invention can greatly weaken the polymerization side reaction in which EO participates, and greatly improve the product yield and purity.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of tris(2-hydroxyethyl)isocyanurate. Background technique [0002] Tris (2-hydroxyethyl) isocyanurate (trade name: Saike) is a three-functional reactive organic small molecule, which can be used as an intermediate for coatings, plasticizers, flame retardants, and curing agents , Synthesis of pharmaceutical and pesticide intermediates. [0003] The synthesis of SEC with cyanuric acid and ethylene oxide (EO) as raw materials was first reported by Allid Company of the United States. The reaction equation is as follows. After cyanuric acid loses protons under the action of a basic catalyst, it forms N negative ions and attacks ethylene oxide. get the product. The accompanying side reactions are the decomposition product 2-oxazolinone, EO self-polymerization, product further polymerized with EO, solvent and EO oligomers (alcohol ethers) under the alkal...

Claims

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Application Information

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IPC IPC(8): C07D251/30B01J31/02B01J27/232B01J27/12
CPCC07D251/30B01J31/0237B01J27/12B01J27/232B01J31/0274B01J31/0275B01J35/19
Inventor 梁兆利李玉博
Owner JIAHUA CHEM TECH DEV SHANGHAI CO LTD
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