CN109553638B - Preparation method of ester group mercaptan organotin - Google Patents
Preparation method of ester group mercaptan organotin Download PDFInfo
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Abstract
The invention relates to a preparation method of ester group mercaptan organotin, which comprises the following steps: mixing organic tin chloride with a solvent, adding an alkaline earth metal compound to adjust the pH value to 2-6, and reacting to obtain an intermediate product; and reacting the intermediate product with a mercapto ester compound to obtain the ester-based mercaptan organotin. Compared with the preparation method of adding liquid caustic soda when reacting organic tin chloride and a sulfhydryl ester compound, the preparation method of the invention saves the problems of troublesome post-treatment and incapability of directly discharging to soil caused by the generation of salt water, basically has no pollution to the environment, and meets the requirements of clean and environment-friendly production.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a preparation method of ester group mercaptan organotin.
Background
Polyvinyl chloride (PVC) is one of early synthetic thermoplastics, and can be widely used in the fields of industry, agriculture, construction, etc. due to its advantages of difficult combustion, plasticization, corrosion resistance, good mechanical properties, high insulating properties, low price, wide sources, etc. However, since the decomposition temperature of PVC is lower than the melting temperature thereof, the decomposition occurs within the processing temperature range, thereby losing part of the physical and chemical properties and being difficult to satisfy the processing requirements, and thus, it is required to improve the thermal stability of PVC. The main methods for improving the thermal stability of PVC comprise: improving the synthesis process to improve the quality of the PVC resin and adding a heat stabilizer into the PVC resin. The latter method is not only simple and effective, but also can prevent long-term thermal degradation during processing.
The lead stabilizers are used in PVC heat stabilizers at first, and are not beneficial to environmental safety and health, so that the use of the lead stabilizers is forbidden or limited in a plurality of countries.
Disclosure of Invention
Based on the above, there is a need for an environmentally friendly and pollution-free organotin ester thiol preparation method.
A preparation method of ester group mercaptan organotin comprises the following steps:
mixing organic tin chloride with a solvent, adding an alkaline earth metal compound to adjust the pH value to 2-6, and reacting to obtain an intermediate product;
and reacting the intermediate product with a mercapto ester compound to obtain the ester-based mercaptan organotin.
The preparation method of the ester-based mercaptan organotin adopts alkaline earth metal compounds to firstly adjust the pH value of a mixed solution of organic tin chloride and a solvent to 2-6, and then produces an intermediate product to react with a mercapto ester compound to obtain the ester-based mercaptan organotin. Research finds that if the alkaline earth metal compound is added to adjust the pH value to be too high, the generated intermediate product is a white solid and the sulfhydryl ester compound is easy to hydrolyze, so that the subsequent reaction of the intermediate product and the sulfhydryl ester compound is not facilitated, and the yield is seriously influenced; if the alkaline earth metal compound is added to adjust the pH value to be too low, the subsequent reaction of chloride ions in the organic tin chloride mixed solution is not thorough, so that the alkaline earth metal compound is added to adjust the pH value to be 2-6, and the ester-based mercaptan organotin is favorably prepared.
In addition, the preparation method of the ester-based mercaptan organotin adopts alkaline earth metal compounds to firstly adjust the pH value of the mixed solution of organic tin chloride and a solvent to 2-6, on one hand, the solubility of the formed alkaline earth metal salt is lower than that of sodium hydroxide, the alkaline earth metal salt is easy to separate from wastewater and is convenient for post-treatment, and the alkaline earth metal salts such as calcium chloride and the like can be directly discharged into soil, so that the method has no pollution to the environment basically; on the other hand, alkaline earth metal salts such as calcium chloride have a wide range of applications and can be recycled. Therefore, compared with the preparation method of adding liquid caustic soda (namely liquid sodium hydroxide) during the reaction of the organic tin chloride and the mercapto ester compound, the preparation method of the invention saves the problems of troublesome post-treatment and incapability of directly discharging to soil caused by the generation of salt water, basically has no pollution to the environment, and meets the requirements of clean and environment-friendly production.
Of organotin ester mercaptidesThe preparation method belongs to one-pot reaction, organic tin chloride and a solvent are fully mixed and dissolved into a uniform and transparent solution, an alkaline earth metal compound is added to adjust the pH value to 2-6 for reaction, and the generated intermediate product is R1Sn(OH)2Cl and [ R ]1Sn(OH)(H2O)2]Cl2Mixture of R1Represents an alkyl group such as methyl or butyl in organotin participating in the reaction; then directly adding a mercapto ester compound into the intermediate product for reaction to prepare ester group mercaptan organotin, wherein the yield reaches more than 90 percent.
In one embodiment, the organic tin chloride is a mixed solution of methyl tin trichloride and dimethyl tin dichloride; or the organic tin chloride is a mixed solution of butyltin trichloride and dibutyltin dichloride. It can be understood that the mass content of the methyl tin trichloride and the dimethyl tin dichloride in the mixed liquid of the methyl tin trichloride and the dimethyl tin dichloride and the mass content of the butyl tin trichloride in the mixed liquid of the butyl tin trichloride and the dibutyl tin dichloride can be selected according to requirements.
In one embodiment, the solvent is water, and the mass ratio of the solvent to the organic tin chloride is 1 (1-2). As water is used as a solvent in the reaction process, no other organic solvent is added, no harmful gas to the environment exists in the whole process, and the preparation method has no pollution to the environment and meets the requirements of clean and environment-friendly production.
In one embodiment, the alkaline earth metal compound is selected from at least one of calcium oxide and calcium hydroxide. The reaction uses calcium oxide and hydroxide, the generated product is calcium chloride aqueous solution, the application range of the calcium chloride is very wide, and the calcium chloride can be recycled.
In one embodiment, the mercaptoester compound is selected from at least one of reverse ester type mercaptoester and non-reverse ester type mercaptoester.
In one embodiment, the reverse ester-type mercapto ester is HSR2COOR3Wherein R is2Is ethyl or propyl, R3Refers to C3～C21An alkyl group of (a); the non-reverse ester type mercapto ester is 2-mercaptoIsooctyl acetate.
In one embodiment, the mercapto ester compound is added in a ratio of (1-1.5): 1 to the amount of chlorine atoms in the organic tin chloride. The slightly excessive sulfhydryl ester compound can completely react with the organic tin chloride participating in the reaction, so that the final product ester-based mercaptan organic tin can play a good thermal stability effect when applied to PVC materials.
In one embodiment, the reaction condition of the intermediate product and the sulfhydryl ester compound is that the intermediate product and the sulfhydryl ester compound react for 2 to 5 hours at 50 to 90 ℃. Because the tin element belongs to the IVA group element, the outer layer of the tin element has an empty electron orbit, has stronger polarization and larger deformability, and can form a metal coordination bond with elements such as sulfur, oxygen and the like. The mercapto group of the mercapto ester compound contains S, and the deformability thereof is stronger than that of oxygen. Therefore, S is easier to replace the original O-Sn bond and combine with Sn to generate an S-Sn bond under the condition that the reaction entropy is increased by the reaction temperature rise and stirring. Therefore, in this reaction, RSn (OH) is reacted with stirring under heating)2Cl and [ RSn (OH) (H)2O)2]Cl2The mixture reacts with a mercapto ester compound to obtain the product ester-group mercaptan organotin.
In one embodiment, after the pH value is adjusted to 2-6, the reaction is continued for 2-5 h.
In one embodiment, the method further comprises the following purification steps: and after the reaction of the intermediate product and the mercaptoester compound is finished, dewatering and drying under the vacuum negative pressure condition of 50-80 ℃, and filtering to obtain the purified ester-based mercaptan organotin.
The organotin ester-based mercaptan prepared by the preparation method of organotin ester-based mercaptan has good physical form and high purity, can effectively prevent decomposition, discoloration and the like during high-temperature processing of polyvinyl chloride (PVC), is suitable for being used as a polyvinyl chloride heat stabilizer and can also be used for preparing the polyvinyl chloride heat stabilizer, effectively avoid decomposition, discoloration and the like during high-temperature processing of polyvinyl chloride (PVC), and enhance the processability of polyvinyl chloride.
Detailed Description
In order that the invention may be more fully understood, a more particular description of the invention will now be rendered by reference to specific embodiments thereof that are illustrated in the appended drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
For better understanding of the present invention, the present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
The following are specific examples.
Example 1
The first step is as follows: firstly, adding 300g of mixed solution of methyl tin trichloride and dimethyl tin dichloride (wherein the mass fractions of the methyl tin trichloride and the dimethyl tin dichloride are 40% and 60%, respectively, and subsequent experiments are carried out according to the mass fraction ratio) and 600g of solvent water into a reactor, and starting stirring to fully mix and dissolve the methyl tin trichloride and the dimethyl tin dichloride into a uniform and transparent solution; then alkaline earth metal compound calcium hydroxide is added step by step to be fully dissolved in the system and promote the reaction, and the reaction is carried out for 5 hours when the pH value is 2.
The second step is that: after the reaction is finished, 642.56g of non-reverse ester type mercaptoester compound EHMA (2-isooctyl thioglycolate) is added and heated to 90 ℃ for reaction for 5 hours to generate 2-isooctyl thioglycolate methyltin. Then removing water, drying and filtering under vacuum and negative pressure at the temperature of 80 ℃. 784.98g of pure isooctyl 2-mercaptoacetate methyltin are obtained, the yield being 95.01%.
Example 2
Substantially the same as in example 1 except that, in the second step, 642.56g of mercaptoethanol isooctanoate, a reverse ester type mercaptoester compound, was added in place of 642.56g of the non-reverse ester type mercaptoester compound EHMA (isooctyl 2-mercaptoacetate) in example 1, and the reaction was carried out by heating to a temperature of 90 ℃ for 5 hours to give mercaptoethanol isooctanoate, methyltin. Vacuum negative pressure dewatering, drying and filtering at 80 deg.c. 786.9g of pure product were obtained in 95.24% yield.
Example 3
Essentially the same as in example 1 except that the organotin chloride in the first step of the reaction was changed to butyltin chloride. Namely:
the first step is as follows: 350g of mixed solution of butyltin trichloride and dibutyltin chloride (wherein the mass fractions of the butyltin trichloride and the dibutyltin chloride are 40% and 60%, respectively) and 700g of solvent water are added into a reactor, stirring is started to enable the butyltin trichloride and the dibutyltin chloride to be fully mixed and dissolved into a uniform and transparent solution, then alkali metal oxide calcium oxide is added step by step to be fully dissolved into the system and promote the reaction, the reaction is carried out when the pH value is 2, and the reaction is carried out for 5 hours.
The second step is that: after the reaction is finished, 592.8g of non-reverse ester type mercaptoester compound EHMA (2-isooctyl thioglycolate) is added and heated to 90 ℃ for reaction for 5 hours to generate 2-isooctyl thioglycolate butyl tin. Vacuum negative pressure dewatering, drying and filtering at 80 deg.c. 768.84g of pure product were obtained in 92.03% yield.
Example 4
Essentially the same as in example 2, except that the organotin chloride in the first step of the reaction was changed to butyltin chloride. Namely:
the first step is as follows: adding 350g of mixed solution of butyltin trichloride and dibutyltin chloride and 700g of solvent water into a reactor, starting stirring to fully mix the butyltin trichloride and the dibutyltin chloride into a uniform and transparent solution, then adding alkali metal oxide calcium oxide step by step to fully dissolve the alkali metal oxide calcium oxide into the system and promote the reaction, and reacting for 5 hours when the pH value is 2.
The second step is that: after the reaction is finished, 592.8g of reverse ester type mercapto ester compound, namely, mercaptoethanol isooctanoate is added, the temperature is heated to 90 ℃ for reaction, and the reaction time is 5h, so that mercaptoethanol isooctanoate butyl tin is generated. Vacuum negative pressure dewatering, drying and filtering at 80 deg.c. 769.5g of pure product were obtained in 92.08% yield.
Example 5
The method is basically the same as that in example 1, except that calcium hydroxide is added to adjust the pH value of the system to 4.0; EHMA is added to react to generate the isooctyl 2-mercaptoacetate methyltin. 801.52g of pure product were obtained in 97.03% yield.
Example 6
The method is basically the same as that in example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0; adding the isooctanoic acid mercaptoethanol ester to react to generate the isooctanoic acid mercaptoethanol ester methyl tin. 802.32g of pure product were obtained in 97.13% yield.
Example 7
The method is basically the same as that in example 1, except that calcium hydroxide is added to adjust the pH value of the system to 6.0; the reaction is carried out by adding EHMA to generate isooctyl 2-mercaptoacetate methyltin. 744.226g of pure product was obtained with a yield of 90.01%.
Example 8
The method is basically the same as that in example 2, except that calcium hydroxide is added to adjust the pH value of the system to 6.0; adding the isooctanoic acid mercaptoethanol ester to react to generate the isooctanoic acid mercaptoethanol ester methyl tin. 745.878g of pure product were obtained in 90.03% yield.
Comparative example 1
The method is basically the same as that in example 1, except that calcium hydroxide is added to adjust the pH value of the system to 8.0; the reaction is carried out by adding EHMA to generate isooctyl 2-mercaptoacetate methyltin. 660.02g of pure product were obtained in 80.03% yield.
Comparative example 2
The method is basically the same as that in example 2, except that calcium hydroxide is added to adjust the pH value of the system to 8.0; adding the isooctanoic acid mercaptoethanol ester to react to generate the isooctanoic acid mercaptoethanol ester methyl tin. 661.8g of pure product were obtained in 80.03% yield.
Example 9
The method is basically the same as the example 2, except that calcium hydroxide is added to adjust the pH value of the system to be 4.0, the reaction time is 2 hours, and then mercaptoethanol isooctanoate is normally added to react to generate mercaptoethanol isooctanoate methyl tin. 786.2g of pure product was obtained in 95.2% yield.
Example 10
The method is basically the same as the example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0, after the reaction is carried out for 2 hours, mercaptoethanol isooctanoate is added to carry out the reaction, and the reaction time is 2 hours, so that methyltin mercaptoethanol isooctanoate is generated. 745.878g of pure product were obtained in 90.03% yield.
Example 11
The method is basically the same as the example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0, after the reaction is carried out for 2 hours, mercaptoethanol isooctanoate is added to carry out the reaction, and the reaction time is 4 hours, so that methyltin mercaptoethanol isooctanoate is generated. 786.8g of pure product were obtained in 95.23% yield.
The following can be seen from the above examples 2 and 10 to 11: the final yield of the reaction varies greatly among the reaction times of the second step of 2 hours, 4 hours and 5 hours, and the reaction time of 4 hours is preferred as an example in the following examples.
Example 12
The method is basically the same as that in example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0, after the reaction is carried out for 2 hours, mercaptoethanol isooctanoate is added to carry out the reaction, the temperature is heated to 70 ℃ for the reaction, and the reaction time is 4 hours, so that mercaptoethanol isooctanoate methyl tin is generated. 805.4g of pure product was obtained, yield 97.5%
Example 13
The method is basically the same as that in example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0, after the reaction is carried out for 2 hours, mercaptoethanol isooctanoate is added to carry out the reaction, the temperature is heated to 50 ℃ for the reaction, and the reaction time is 4 hours, so that mercaptoethanol isooctanoate methyl tin is generated. 775.0g of pure product was obtained, giving a yield of 93.8%
Example 14
The same as example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0, 889.5g of mercaptoethanol oleate is added to react after 2 hours of reaction, the reaction is carried out by heating to 70 ℃ for 4 hours, and mercaptoethanol oleate methyltin oleate is produced. 995.2g of pure product were obtained in 92.5% yield.
Example 15
The same as example 2, except that calcium hydroxide is added to adjust the pH value of the system to 4.0, 895g of mercaptoethanol stearate is added to react after 2h, the reaction is carried out by heating to 70 ℃ for 4h, and thus mercaptoethanol stearate methyltin is produced. 922.3g of pure product was obtained with a yield of 85.5%
Analysis of Experimental results
The following examples 1 to 2 show that: whether the substrate is a non-reverse ester type mercaptoester or a reverse ester type mercaptoester compound, the preparation of the organotin ester-based thiol can be carried out by the method of the present invention.
The following examples 3 to 4 show that: when the substrate is a mixture of methyltin chloride or butyltin chloride, the substrate can react with an alkaline earth metal compound and then react with a mercaptoester compound to prepare ester-based organotin mercaptide; meanwhile, the calcium oxide can also be used for adjusting the pH value, and the effect is equivalent to that of calcium hydroxide.
The following results were obtained in examples 5 to 8 and comparative examples 1 to 2: when the pH value is changed, whether the substrate is a non-reverse ester type sulfhydryl ester or a reverse ester type sulfhydryl ester compound has direct influence on the yield of the reaction. The yield was highest when the pH of the reaction was adjusted to 4.0. After a pH of more than 6, the yield of the product obtained decreases considerably. The main reasons are: on one hand, after the pH value is more than 6, a part of solid components, generally Sn-O-Sn, are mixed in the generated product, and in comparison, no direct Sn-O bond is easy to open, so that the probability of attaching the sulfhydryl ester is reduced, and on the other hand, when the pH value is too high, the sulfhydryl ester compound can be hydrolyzed, and the yield of the reaction is influenced to a certain extent.
From example 9 above, it can be seen that: the final yield of the reaction is not very different when the reaction time of the first step is 2h and 5 h.
The following can be seen from the above examples 2 and 10 to 11: the final yield of the reaction is greatly different when the reaction time of the second step is 2h, 4h and 5 h. In the second step of the reaction, the yield of the whole reaction is important, and the reaction time is controlled to be more than 4 hours so as to ensure the full reaction.
The above examples 2 and 12 to 13 show that: the final yields of the reaction vary greatly when the reaction temperature of the second step is 50 deg.C, 70 deg.C, 90 deg.C. In the case where the reaction time is determined, if the reaction temperature is too low, the activation reaction is insufficient; if the reaction temperature is too high, the hydrolysis of the ester compound is promoted, and the reaction yield is influenced to a certain extent. Therefore, the reaction temperature is preferably 70 ℃.
The following examples 2 and 14 to 15 show that: for the reverse ester type mercapto ester compound, the liquid reactants react more fully than the solid reactants, and the yield is much higher.
The following is a PVC heat stabilizer effect verification experiment.
PVC heat stabilizers were prepared from isooctyl methyl tin 2-mercaptoacetate of example 1, mercaptoethanol methyl tin isooctanoate of example 2, mercaptoethanol methyl tin oleate of example 14, and mercaptoethanol methyl tin stearate of example 15, respectively.
The PVC heat stabilizer comprises the following components in percentage by mass: in the ester-based mercaptan organotin in each embodiment, components with tin content of 10% participate in compounding, and other compounding components are as follows: 30% of calcium stearate, 13% of zinc glycerolate, 40% of auxiliary heat stabilizer, 2% of antioxidant, 3% of anti-UV auxiliary agent and 2% of dispersing agent. The prepared PVC heat stabilizer is respectively numbered as T1, T2, T3 and T4.
The method for preparing ester group mercaptan organotin is common in the market at present, namely: stirring and mixing thiol ester compound isooctanoate mercaptoethanol ester, methyl tin chloride and water, heating to 60-80 ℃, adding inorganic base NaOH aqueous solution to adjust the pH value to 6-8, stirring and reacting for 4-6 hours, washing with water after the reaction is finished, filtering, and distilling the filtrate under reduced pressure to obtain isooctanoate mercaptoethanol methyltin. Analogous analogy is made with mercaptoethanolmethyltin isooctanoate from example 2 of the present invention as an analogous compound; the analogous compound is prepared into PVC heat stabilizer by the same method, and is named as T0.
The PVC heat stabilizer is respectively mixed with PVC resin, a torque rheological experiment method in a dynamic method is adopted to test the formula of the heat stabilizer, the method is simple and easy to implement and strong in operability, the PVC heat stabilizers T1, T2, T3, T4 and T0 are respectively mixed with PVC resin powder, an extrudate is processed by using a Hamp RM-200C mixing type torque rheometer at the high temperature of 190 ℃, a uniform wafer is prepared by a mould, and sampling is carried out once every 3min until wafers made by all extrudates turn yellow. The plastication time was recorded and the wafers were tested for the b-value chromaticity index using a German BYK-Gardner glossmeter AG-4454, which was very effective in comparing the effect of the heat stabilizer over time, with more positive b values showing more yellow and more negative b values showing more blue, as shown in Table 1.
TABLE 1
From table 1 it can be seen that: (1) of T1 and T2, T2 exhibited a better heat-stabilizing effect. The T3 and T4 are relatively poor in stability of T1 compared with T1, and the comparison shows that the thermal stability of the retro-ester type organotin thiol is better than that of the non-retro ester type organotin thiol. (2) The comparison of the thermal stability effects of T2 and T0 shows that the thermal stability effects of the organotin esterthiol obtained under different reaction process conditions are equivalent, and the preparation method of the organotin esterthiol is proved to be feasible and reliable.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. The preparation method of ester group mercaptan organotin is characterized by comprising the following steps:
mixing organic tin chloride with a solvent, adding an alkaline earth metal compound to adjust the pH value to 2-4, and reacting to obtain an intermediate product;
reacting the intermediate product with a mercapto-ester compound at 50-90 ℃ for 4-5 h to obtain ester-group mercaptan organotin;
the amount of the mercapto ester compound added is such that the ratio of the amount of the mercapto ester compound to the amount of the substance having a chlorine atom in the organic tin chloride is (1-1.5): 1.
2. The method according to claim 1, wherein the organic tin chloride is a mixture of methyl tin trichloride and dimethyl tin dichloride.
3. The method according to claim 1, wherein the organic tin chloride is a mixture of butyltin trichloride and dibutyltin dichloride.
4. The preparation method according to claim 1, wherein the solvent is water, and the mass ratio of the solvent to the organotin chloride is 1 (1-2).
5. The method according to claim 1, wherein the alkaline earth metal compound is at least one selected from the group consisting of calcium oxide and calcium hydroxide.
6. The method according to claim 1, wherein the mercaptoester compound is at least one selected from the group consisting of reverse ester type mercaptoester and non-reverse ester type mercaptoester.
7. The method according to claim 6, wherein the reverse ester-type mercapto ester is R3COOR2SH, wherein R2Is ethyl or propyl, R3Refers to C3～C21Alkyl groups of (a); the non-reverse ester type mercapto ester is 2-isooctyl thioglycolate.
8. The method according to any one of claims 1 to 6, wherein the reaction of the intermediate product with the mercaptoester compound is carried out at 70 ℃ for 4 hours.
9. The method according to any one of claims 1 to 6, wherein the reaction is continued for 2 to 5 hours after the pH is adjusted to 2 to 4.
10. The method according to any one of claims 1 to 6, further comprising a purification step of: and after the reaction of the intermediate product and the mercaptoester compound is finished, dewatering and drying under the vacuum negative pressure condition of 50-80 ℃, and filtering to obtain the purified ester-based mercaptan organotin.
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