Thiophosphate compound and preparation method thereof
By continuously synthesizing thiophosphate compounds in a microchannel reactor, the problems of difficult control of multi-component reactions and use of precious metal catalysts in existing technologies have been solved, and the preparation of thiophosphate compounds with high efficiency and low cost has been achieved.
Patent Information
- Application Number
- CN202511617833.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-11-06
- Publication Date
- 2026-02-10
AI Technical Summary
Existing synthesis processes for thiophosphate compounds face challenges such as difficulty in controlling multi-component reactions, increased costs due to the use of precious metal catalysts, and difficulties in large-scale production caused by stringent reaction conditions.
Thiophosphate compounds were continuously synthesized under mild conditions using a microchannel reactor. The reaction was completed by pumping the compound of formula (II) and a toluene solution of sulfur into the microchannel reactor and holding for 2 to 5 minutes.
This method enables the efficient preparation of thiophosphate compounds under mild reaction conditions, simplifying the purification process, reducing production costs, and improving production efficiency.
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of organic synthesis technology, and specifically relates to a thiophosphate compound and its preparation method. Background Technology
[0002] In recent years, the academic community has explored various synthesis routes for thiophosphate compounds. For example, Zhang Xinghua's research group developed a "one-pot three-component coupling reaction" system using haloalkanes, elemental sulfur, and phosphites as raw materials; Chandra MR Volla's team reported a photocatalytic synthesis strategy. However, existing technical routes generally suffer from the following bottlenecks: First, multi-component reactions require strict control of the reaction sequence and conditions, easily generating byproducts and making purification difficult; second, the use of special catalysts (such as palladium, ruthenium, and other noble metal catalysts) increases production costs, and catalyst residues may affect their application effects and performance; third, high-temperature and high-pressure conditions place stringent requirements on equipment, resulting in poor process stability and making large-scale production difficult. Although the "one-pot three-component coupling reaction" and photocatalytic methods have made some progress in simplifying the steps, they have not fundamentally solved the problems of high raw material costs and harsh reaction conditions.
[0003] Based on this, we will develop a new method for preparing thiophosphate compounds using inexpensive raw materials and under mild reaction conditions to achieve precise control of product structure. At the same time, the use of microchannel continuous flow can further improve the production efficiency of fine chemicals, which is of great strategic significance for breaking through the current technological barriers. Summary of the Invention
[0004] To address the above-mentioned technical problems, this invention proposes a method for the continuous synthesis of thiophosphate compounds.
[0005] This invention provides a method for the continuous synthesis of thiophosphate compounds, the general structural formula of which is shown in formula (I): (I); Where R is selected from C4, C8, and C 10 C 12 C 13 and C 18 Any one of straight-chain or branched alkyl groups.
[0006] The preparation method of the above-mentioned thiophosphate compounds includes the following steps: The compound of formula (II) and a toluene solution of sulfur were pumped into a microchannel reactor and held for 2 to 5 minutes. The reaction temperature of the microchannel reactor was 50 to 80°C. (II); Wherein, R is selected from C4, C8, C 10 C12 C 13 and C 18 Any one of straight-chain or branched alkyl groups; The reaction formula is as follows: .
[0007] The synthesized products include, but are not limited to, at least one of the following products: tri-n-octyl thiophosphate, tri-n-decyl thiophosphate, tri(tetrazyl) thiophosphate, tributyl thiophosphate, triisooctyl thiophosphate, trilauryl thiophosphate, and tri(octadecyl) thiophosphate.
[0008] The present invention has the following advantages and effects compared with the prior art: The method for preparing thiophosphate compounds provided by this invention only requires the compound of formula (II) and a toluene solution of sulfur to be pumped into a microchannel reactor simultaneously and left for 2-5 minutes to complete the reaction. The reaction process is safe and easy to control, and the engineering scale-up is simple and efficient, solving the common problem of "success in small-scale tests but failure in pilot-scale tests" in traditional chemical scale-up. Detailed Implementation
[0009] To enable those skilled in the art to better understand the present invention, the present invention will now be further described in conjunction with specific embodiments.
[0010] Example 1: The microchannel reactor was heated to 45°C. Trioctyl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 125 mL / min and 16 mL / min respectively using a plunger pump. After reacting in the microchannel reactor for 1 minute, the receiver accepted the reaction solution to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding trioctyl thiophosphate.
[0011] The microchannel reactor used in this invention is a commercially available conventional instrument.
[0012] Example 2: The microchannel reactor was heated to 50°C. Tridecyl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 150 mL / min and 16 mL / min respectively using a plunger pump. After reacting in the microchannel reactor for 2 minutes, the reaction solution was collected by a receiver to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding tridecyl phosphite.
[0013] Example 3: The microchannel reactor was heated to 48°C. Tridecyl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 188 mL / min and 18 mL / min respectively using a plunger pump. After reacting for 1 minute in the microchannel reactor, the reaction solution was received by a receiver to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding tridecyl phosphite.
[0014] Example 4: The microchannel reactor was heated to 75°C. Tributyl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 75 mL / min and 17.9 mL / min respectively using a plunger pump. After reacting for 5 minutes in the microchannel reactor, the reaction solution was received by a receiver and allowed to cool naturally to room temperature to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding tributyl thiophosphate.
[0015] Example 5: The microchannel reactor was heated to 60°C. Triisooctyl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 125 mL / min and 18 mL / min respectively using a plunger pump. After reacting for 2 minutes in the microchannel reactor, the reaction solution was collected by a receiver to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding triisooctyl phosphite.
[0016] Example 6: The microchannel reactor was heated to 52°C. Trilauryl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 175 mL / min and 20 mL / min respectively using a plunger pump. After reacting in the microchannel reactor for 2 minutes, the reaction solution was collected by a receiver to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding trilauryl phosphite.
[0017] Example 7: The microchannel reactor was heated to 70°C. Trioctadecyl phosphite and a 5% sulfur toluene solution were pumped into the reactor at a rate of 195 mL / min and 21 mL / min respectively using a plunger pump. After reacting in the microchannel reactor for 4 minutes, the reaction solution was collected by a receiver to obtain a crude solution. The crude solution was then subjected to vacuum distillation to separate the solvent and excess sulfur, yielding trioctadecyl phosphite.
[0018] In summary, the present invention provides a method for the continuous synthesis of thiophosphate compounds. The preparation method only requires pumping the compound of formula (II) and a toluene solution of sulfur into a microchannel reactor and holding it for 2-5 minutes to complete the process. The reaction process is safe and easy to control, and the engineering scale-up is simple and efficient, solving the common problem of "success in small-scale trials but failure in pilot-scale trials" in traditional chemical scale-up.
[0019] The above are merely preferred embodiments of the present invention and do not limit the scope of the patent. All equivalent changes and modifications made within the scope of the present invention should still fall within the scope of the present invention.
Claims
1. A thiophosphate compound, characterized in that, The compound shown in formula (Ⅰ): （I）； Where R is selected from C4, C8, and C 10 C 12 C 13 and C 18 Any one of straight-chain or branched alkyl groups.
2. A thiophosphate compound as described in claim 1, characterized in that, The thiophosphate compounds are selected from at least one of tri-n-octyl thiophosphate, tri-n-decyl thiophosphate, tri(tetrazyl) thiophosphate, tributyl thiophosphate, triisooctyl thiophosphate, trilauryl thiophosphate, and tri(octadecyl) thiophosphate.
3. A method for preparing the compound of claim 1, comprising the following steps: The compound of formula (II) and a toluene solution of sulfur were pumped into a microchannel reactor and held for 2 to 5 minutes. The reaction temperature of the microchannel reactor was 50 to 80°C. (II); in, The R is selected from C4, C8, and C 10 C 12 C 13 and C 18 Any one of straight-chain or branched alkyl groups.