CN114149376A - Preparation method of tris (2-hydroxyethyl) isocyanurate - Google Patents

Preparation method of tris (2-hydroxyethyl) isocyanurate Download PDF

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CN114149376A
CN114149376A CN202111265169.6A CN202111265169A CN114149376A CN 114149376 A CN114149376 A CN 114149376A CN 202111265169 A CN202111265169 A CN 202111265169A CN 114149376 A CN114149376 A CN 114149376A
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hydroxyethyl
tris
isocyanurate
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梁兆利
李玉博
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Jiahua Science and Technology Development Shanghai Ltd
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    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
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    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
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    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
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    • B01J31/0274Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 containing silicon
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    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0272Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0275Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 also containing elements or functional groups covered by B01J31/0201 - B01J31/0269
    • BPERFORMING OPERATIONS; TRANSPORTING
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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 with 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" (soft hard acid base theory) added in an amount of 0-3% by mass of cyanuric acid. The preparation method provided by the invention can greatly weaken the polymerization side reaction of EO participation, and greatly improve the product yield and purity.

Description

Preparation method of tris (2-hydroxyethyl) isocyanurate
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of tris (2-hydroxyethyl) isocyanurate.
Background
Tris (2-hydroxyethyl) isocyanurate (trade name: mosaic) is a trifunctional active small organic molecule, and can be used as an intermediate for synthesizing coatings, plasticizers, flame retardants, curing agents and pharmaceutical and pesticide intermediates.
The synthesis of seik from cyanuric acid and Ethylene Oxide (EO) as raw materials was first reported by Allid corporation of usa, and the reaction equation is shown below, wherein cyanuric acid loses proton under the action of basic catalyst to form N negative ion, which attacks ethylene oxide to obtain the product. The accompanying side reactions are 2-oxazolinone which is the product of the decomposition of the product of the thiuram under the alkaline high temperature system, the self polymerization of EO, the oligomer formed by the product further polymerizing with EO, and the oligomer of the solvent and EO (when the alcohol ether solvent is the reaction solvent). Therefore, the choice of the reaction solvent type and catalyst has a large impact on product yield and purity.
Figure BDA0003326589730000011
In the existing seek synthesis process, N-Dimethylformamide (DMF) is mostly adopted as a reaction solvent, no catalyst is added or inorganic strong base such as NaOH is additionally added as a catalyst, and the yield of a pure product (the yield of quantitative analysis by high performance liquid chromatography) is about 70-80%. EO self-polymerization can be also initiated by alkaline substances generated by self-decomposition of DMF, so that yield is unstable, stability of process batches is poor, and an operation window is narrow. Researchers also adopt alcohol ether series solvents such as ethylene glycol monomethyl ether, the yield of a pure product is 70-85%, an acetone-water solvent system is 82%, detection analysis shows that when alcohol ether solvents such as ethylene glycol monomethyl ether, ethylene glycol, methanol, ethanol and the like are adopted as reaction solvents, the yield of the system is generally lower than that of a DMF system due to the fact that oligomers formed by opening of the alcohol ether and EO in the system are detected, and a large amount of polyether byproducts in the system influence the purity of products, and a careful purification process is needed for obtaining high-purity saxok.
Therefore, how to control the side reaction, especially the polymerization process involving EO, and improve the yield and purity of the product becomes a big difficulty.
Disclosure of Invention
The invention aims to provide a method for synthesizing tris (2-hydroxyethyl) isocyanurate, and the reaction system can greatly weaken the polymerization side reaction in which EO participates, so that the reaction yield is increased to be more than 90%, and the purity of a crude product is more than 90% (high performance liquid phase HPLC purity). The high crude product yield and purity greatly simplify the subsequent purification process and reduce the production cost.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of tris (2-hydroxyethyl) isocyanurate comprises the following steps:
reacting cyanuric acid with ethylene oxide in the presence of a catalyst I, a catalyst II and a solvent to obtain the tris (2-hydroxyethyl) isocyanurate.
Preferably, the preparation method of the tris (2-hydroxyethyl) isocyanurate comprises the following steps:
mixing and heating cyanuric acid, a catalyst I, a catalyst II and a solvent, and then introducing ethylene oxide into the mixed solution for reaction to obtain the tris (2-hydroxyethyl) isocyanurate.
The catalyst I is selected from pyridine, triethylamine, dimethylamine and 1, 8-diazabicyclo [ 5.4.0%]Undec-7-ene (abbreviated DBU), Na2CO3、NaHCO3、Li2CO3、LiCl、Cs2CO3One or more of CsF, NaF and KF;
the catalyst II is 'stearic acid' (DOI: 10.1021/ja00905a001) selected from one or more of boron trifluoride, trimethylchlorosilane and titanium tetrachloride;
the solvent is one or more selected from N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, hexamethylphosphoramide, methanol, ethanol, ethylene glycol monomethyl ether and water.
The addition amount of the catalyst I is 0.5-3 percent of the mass of cyanuric acid, preferably 0.5-1.5 percent; the addition amount of the catalyst II is 0-3 percent of the mass of cyanuric acid, preferably 0.1-1.5 percent; the adding amount of the solvent is 2-8 times, preferably 3-5 times of the mass of cyanuric acid; the dosage of the ethylene oxide is 1.05 to 5 times of the mass of the cyanuric acid.
The reaction temperature is 64-140 ℃, preferably 100-120 ℃, the reaction time is not particularly limited in the invention, the specific reaction time can be determined according to monitoring, and optionally, the reaction time is 0.5-3 h.
The invention has the beneficial effects that:
according to the preparation method of tris (2-hydroxyethyl) isocyanurate provided by the invention, through the combination selection of the solvent and the addition of two different types of catalysts in a reaction system, particularly the addition of the catalyst II, the polymerization side reaction of EO participation can be greatly weakened, the product yield and purity can be greatly improved, the crude product yield can be improved to more than 90%, and the product purity can reach more than 90% (high performance liquid phase HPLC purity) without recrystallization purification, for example, the total yield of the product further purified and refined product can still reach more than 80%, the high reaction yield and the crude product purity greatly simplify the subsequent purification process, reduce the production cost, and meet the specific requirements in downstream high-end application scenes.
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In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a liquid chromatogram of the wet crude product of example 1;
FIG. 2 is a liquid chromatogram of the product obtained in example 1 after filtration and drying.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional chemical products which can be obtained commercially.
Example 1
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
412g of N, N-dimethylacetamide, 100g of cyanuric acid (purity 98%), 0.5g of dimethylamine and 1.2g of BF were added3·Et2O(BF346.5 wt%) into a 3L reaction kettle, heating to 110 ℃, pumping 108g of ethylene oxide by a feeding pump for reaction, controlling the reaction temperature to 110 ℃, reacting for 2h, cooling the reaction liquid to 30 ℃ after the reaction is finished, and carrying out reduced pressure distillation to remove N, N-dimethylacetamide to obtain 257g of a wet crude product of tris (2-hydroxyethyl) isocyanurate; then 500mL of acetone was added to the wet crude product, stirred at room temperature for 0.5 hour, filtered and dried to obtain 186g of tris (2-hydroxyethyl) isocyanurate with a yield of 92%, and the purity of the tris (2-hydroxyethyl) isocyanurate product was 94% by HPLC analysis.
Example 2
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
adding 380g of pyridine and 100g of cyanuric acid (with the purity of 98%) into a 3L reaction kettle, heating to 110 ℃, pumping 115g of ethylene oxide by a feeding pump to react, controlling the reaction temperature to 110 ℃, reacting for 2.5h, cooling the reaction liquid to 35 ℃ after the reaction is finished, carrying out reduced pressure distillation to remove pyridine to obtain 264g of a wet crude product of tris (2-hydroxyethyl) isocyanurate, adding 500mL of acetone into the wet crude product, stirring at room temperature for 0.5h, filtering and drying to obtain 192g of tris (2-hydroxyethyl) isocyanurate with the yield of 95%, and analyzing the purity of the tris (2-hydroxyethyl) isocyanurate product by high performance liquid chromatography to obtain 90%.
Example 3
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
2027g N-Methylpyrrolidone, 1006g cyanuric acid (98% purity), 5g Cs2CO3And 6g BF3·Et2O(BF346.5 weight percent) of the mixture is added into a 20L reaction kettle, the temperature is increased to 110 ℃, 1091g of ethylene oxide is pumped by a feeding pump to react, the reaction temperature is controlled to be 110 ℃, the reaction time is 1.5h, and the reaction is carried out after the reaction is finishedCooling the solution to 40 ℃, discharging the solution to 50L of three-in-one equipment, adding 8580g of acetonitrile, stirring the solution at 60 ℃ for 0.5 hour, cooling the solution to 10 ℃, filtering and drying the solution in the three-in-one equipment to obtain 1927g of tris (2-hydroxyethyl) isocyanurate, wherein the yield is 95 percent, and the purity of the tris (2-hydroxyethyl) isocyanurate product is 93 percent by high performance liquid chromatography analysis.
Example 4
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
adding 412g of N, N-dimethylacetamide, 100g of cyanuric acid (purity is 98%) and 0.5g of dimethylamine into a 3L reaction kettle, heating to 110 ℃, pumping 108g of ethylene oxide by a feeding pump for reaction, controlling the reaction temperature to be 110 ℃, reacting for 2h, cooling the reaction solution to 30 ℃ after the reaction is finished, and carrying out reduced pressure distillation to remove the N, N-dimethylacetamide to obtain a wet crude product of tris (2-hydroxyethyl) isocyanurate; then 500mL of acetone was added to the wet crude product, stirred at room temperature for 0.5 hour, filtered and dried to obtain 155g of tris (2-hydroxyethyl) isocyanurate with a yield of 77%, and the purity of the tris (2-hydroxyethyl) isocyanurate product was 84% by HPLC analysis.
Example 5
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
adding 412g of N, N-dimethylacetamide, 100g of cyanuric acid (purity is 98%), 0.5g of dimethylamine and 0.89g of trimethylchlorosilane into a 3L reaction kettle, heating to 110 ℃, then pumping 108g of ethylene oxide by a feeding pump for reaction, controlling the reaction temperature to be 110 ℃, reacting for 3h, cooling the reaction solution to 30 ℃ after the reaction is finished, and removing N, N-dimethylacetamide by reduced pressure distillation to obtain a wet crude product of tris (2-hydroxyethyl) isocyanurate; then 500mL of acetone was added to the wet crude product, stirred at room temperature for 0.5 hour, filtered and dried to obtain 190g of tris (2-hydroxyethyl) isocyanurate with a yield of 94%, and the purity of the tris (2-hydroxyethyl) isocyanurate product was 91% by HPLC analysis.
Example 6
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
200g of N, N-dimethylformamide, 104g of cyanuric acid (purity 98%), 2.9g of triethylamine and 0.21g of BF were mixed3·Et2O(BF346.5 wt%) into a 3L reaction kettle, heating to 95 ℃, pumping 110g of ethylene oxide by a feeding pump for reaction, controlling the reaction temperature to 95 ℃ and the reaction time to be 1h, cooling the reaction liquid to 30 ℃ after the reaction is finished, and removing N, N-dimethylformamide by reduced pressure distillation to obtain a wet crude product of tris (2-hydroxyethyl) isocyanurate; then 300mL of acetone is added into the wet crude product, the mixture is stirred for 0.5 hour at room temperature, filtered and dried to obtain 183g of tris (2-hydroxyethyl) isocyanurate, the yield is 90 percent, and the purity of the tris (2-hydroxyethyl) isocyanurate product is 91 percent by high performance liquid chromatography analysis.
Example 7
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
394g of water, 100g of cyanuric acid (purity 98%), 1.45g of sodium carbonate and 3.16g of BF were mixed3·Et2O(BF346.5 wt%) into a 3L reaction kettle, heating to 100 ℃, pumping 110g of ethylene oxide by a feeding pump for reaction, controlling the reaction temperature to 100 ℃, reacting for 1h, cooling the reaction liquid to 40 ℃ after the reaction is finished, and removing water by reduced pressure distillation to obtain a wet crude product of tris (2-hydroxyethyl) isocyanurate; then 500mL of acetone was added to the wet crude product, stirred at room temperature for 0.5 hour, filtered and dried to obtain 198g of tris (2-hydroxyethyl) isocyanurate with a yield of 98%, and the purity of the tris (2-hydroxyethyl) isocyanurate product was 91% by HPLC analysis.
Example 8
This example provides a method for preparing tris (2-hydroxyethyl) isocyanurate, including the following steps:
432g of methanol, 101g of cyanuric acid (purity 98%), 0.7g of KF and 1.2g of BF were mixed3·Et2O(BF346.5 weight percent) of the mixture is added into a 10L reaction kettle, the temperature is raised to 64 ℃, 112g of ethylene oxide is pumped into the kettle by a feeding pump for reaction, the reaction temperature is controlled to 64 ℃, and the reaction is carried outThe time is 0.5h, after the reaction is finished, the reaction solution is cooled to 10 ℃, filtered and dried to obtain 187g of the wet crude product of the tris (2-hydroxyethyl) isocyanurate, the yield is 93 percent, and the purity of the tris (2-hydroxyethyl) isocyanurate product is 97 percent after the high performance liquid chromatography analysis.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (5)

1. A preparation method of tris (2-hydroxyethyl) isocyanurate is characterized by comprising the following steps:
reacting cyanuric acid with ethylene oxide in the presence of a catalyst I, a catalyst II and a solvent to obtain the tris (2-hydroxyethyl) isocyanurate.
2. The method for producing tris (2-hydroxyethyl) isocyanurate according to claim 1,
the catalyst I is selected from pyridine, triethylamine, dimethylamine and 1, 8-diazabicyclo [ 5.4.0%]Undec-7-ene, Na2CO3、NaHCO3、Li2CO3、LiCl、Cs2CO3One or more of CsF, NaF and KF;
the catalyst II is a hard acid and is selected from one or more of boron trifluoride, trimethylchlorosilane and titanium tetrachloride;
the solvent is one or more selected from N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, hexamethylphosphoramide, methanol, ethanol, ethylene glycol monomethyl ether and water.
3. The method for producing tris (2-hydroxyethyl) isocyanurate according to claim 1 or 2, wherein said catalyst I is added in an amount of 0.5 to 3%, preferably 0.5 to 1.5% by mass of cyanuric acid; the addition amount of the catalyst II is 0-3 percent of the mass of cyanuric acid, preferably 0.1-1.5 percent; the adding amount of the solvent is 2 to 8 times, preferably 3 to 5 times of the mass of the cyanuric acid.
4. Process for the preparation of tris (2-hydroxyethyl) isocyanurate according to any one of claims 1 to 3, characterized in that the reaction temperature is between 64 and 140 ℃, preferably 100 and 120 ℃.
5. The method for producing tris (2-hydroxyethyl) isocyanurate according to any one of claims 1 to 4, wherein the amount of ethylene oxide is 1.05 to 5 times the mass of cyanuric acid.
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Cited By (2)

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CN115308322A (en) * 2022-07-07 2022-11-08 佳化化学科技发展(上海)有限公司 Method for detecting tris (2-hydroxyethyl) isocyanurate in reaction kettle liquid by high performance liquid chromatography and application
CN115480018A (en) * 2022-07-29 2022-12-16 佳化化学科技发展(上海)有限公司 Method for determining content of mosaic

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115308322A (en) * 2022-07-07 2022-11-08 佳化化学科技发展(上海)有限公司 Method for detecting tris (2-hydroxyethyl) isocyanurate in reaction kettle liquid by high performance liquid chromatography and application
CN115480018A (en) * 2022-07-29 2022-12-16 佳化化学科技发展(上海)有限公司 Method for determining content of mosaic

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