CN112851498B - Preparation method and application of stannous isooctenoate - Google Patents
Preparation method and application of stannous isooctenoate Download PDFInfo
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- CN112851498B CN112851498B CN202011636526.0A CN202011636526A CN112851498B CN 112851498 B CN112851498 B CN 112851498B CN 202011636526 A CN202011636526 A CN 202011636526A CN 112851498 B CN112851498 B CN 112851498B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
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- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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- C07—ORGANIC CHEMISTRY
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
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Abstract
The invention provides a preparation method and application of stannous isooctanoate, which solve the technical problems of complex preparation process, safety requirement and high cost of the existing stannous octoate. The invention can be widely applied to the technical field of stannous octoate.
Description
Technical Field
The invention belongs to the technical field of stannous octoate, and particularly relates to a preparation method and application of stannous isooctenoate.
Background
The chemical name of stannous octoate is 2-ethyl stannous hexanoate, which is a chemical product of tin. Stannous octoate is easy to hydrolyze in acidic and alkaline aqueous solutions, has a small stable pH value range, is easy to be oxidized and decomposed by oxygen and other oxidants in the air, and is difficult to prepare, stannous octoate is widely used as a catalyst of polyurethane and medium carbon fatty acid ester, and a commercial isooctanoic acid preparation process is complex; the other is that isooctyl aldehyde obtained by aldol condensation is hydrogenated into isooctyl alcohol, then alkalization dehydrogenation is carried out, and isooctyl acid is obtained by acidification. Both methods have complex process, high process safety requirement and high cost. The sodium isooctanoate prepared by the two methods is saponified and then reacts with stannous chloride to obtain stannous octoate.
At present, most of stannous octoate prepared at home and abroad adopts an aldehyde disproportionation method, an acid anhydride method, a double decomposition method and the like, and the methods have the defects of unstable process control, complex operation and low stannous content, so that the industrial production of the stannous octoate is limited. Therefore, there is a need for a new catalyst that can replace stannous octoate.
Disclosure of Invention
The invention aims to solve the defects of the background technology, and provides a preparation method of stannous isooctoate, which has simple process and low cost.
The invention provides a preparation method of stannous isooctoate, which comprises the steps of taking isooctenal as a raw material, carrying out disproportionation reaction in an alkaline solution, adding stannous chloride, and carrying out double decomposition reaction to obtain the stannous isooctoate. The method specifically comprises the following steps:
(1) disproportionation reaction: adding the alkaline solution into a reaction kettle, controlling the reaction temperature, slowly adding isooctenal into the reaction kettle under stirring, and carrying out disproportionation reaction to obtain isooctoate;
(2) double decomposition reaction: adding a stannous chloride solution under the protection of nitrogen, stirring, controlling the reaction temperature, carrying out double decomposition reaction, standing for layering, collecting the upper mother liquor, carrying out reduced pressure distillation, controlling the distillation temperature and time, reducing the nitrogen to be empty after the distillation is finished, reducing the nitrogen to 25-30 ℃ under the protection of the nitrogen, and filtering to obtain the stannous isooctoate.
Preferably, the alkaline solution is one of sodium hydroxide solution and potassium hydroxide solution.
Preferably, the mass fraction of the alkaline solution is 30% to 50%.
Preferably, the molar ratio of the alkaline solution to the isooctylaldehyde is 1 (1-5).
Preferably, the disproportionation reaction temperature is 25-80 ℃.
Preferably, the temperature of the double decomposition reaction is 40-90 ℃.
Preferably, the vacuum degree of the negative pressure distillation is 1-10 mmHg.
Preferably, the distillation temperature is 150-250 ℃, and the distillation time is 20-40 min.
The stannous isooctoate prepared by the preparation method can be used as a catalyst in polyester reaction.
The invention has the beneficial effects that:
(1) the stannous isooctanoate prepared by the invention is a new catalyst for polyester reaction, and is prepared by taking isooctene aldehyde as a reactant to perform disproportionation reaction in an alkaline solution to generate isooctoate, adding stannous chloride to perform double decomposition reaction, and the tin content of the prepared stannous isooctanoate reaches over 29 percent.
(2) The stannous isooctanoate prepared by the method shows good catalytic activity to polyester reaction, can be used as a catalyst in the polyester reaction, and when the stannous isooctanoate is used as a catalyst for preparing isooctanol isooctanoate, the conversion rate of isooctanol isooctanoate can reach 99.7 percent, so that the economic benefit is obviously improved, and the stannous isooctanoate is suitable for industrial production.
(3) The stannous isooctanoate prepared by the invention contains isooctanol and unreacted isooctenal generated by disproportionation reaction, and the isooctanol and the unreacted isooctenal are removed by organic phase vacuum distillation. Therefore, the post-treatment process is simple, free of three wastes, safe, nontoxic and suitable for industrial production.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present application clearer, the present application is further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
Example 1
A preparation method of stannous isooctoate comprises the following specific steps:
(1) disproportionation reaction: adding 58.88g of sodium hydroxide with the mass fraction of 30% into a 500ml four-diameter bottle with a stirrer, controlling the reaction temperature to be 25 ℃, slowly adding 100g of isooctylaldehyde into the four-diameter bottle under stirring, and carrying out disproportionation reaction to obtain isooctoate;
(2) double decomposition reaction: dissolving 88.5 g of stannous chloride dihydrate in 1L of water, adding a stannous chloride solution into the isooctoate prepared in the step (1) under the nitrogen protection atmosphere, controlling the reaction temperature to be 40 ℃, stirring for 20min, carrying out double decomposition reaction, standing for layering, collecting an upper layer mother solution, carrying out reduced pressure distillation for 1mmHg, controlling the distillation temperature to be 150 ℃, continuing for 10min, stopping distillation, breaking the nitrogen, reducing the nitrogen to be air, reducing the nitrogen protection temperature to 25-30 ℃, filtering to obtain a clear, transparent and viscous liquid, namely stannous isooctoate, wherein the stannous content in the prepared stannous isooctoate is 29%, and the process yield is 90.6%.
Example 2
A preparation method of stannous isooctanoate comprises the following specific steps:
(1) disproportionation reaction: adding 78.5g of sodium hydroxide with the mass fraction of 40% into a 500ml four-diameter bottle with a stirrer, controlling the reaction temperature to be 40 ℃, slowly adding 100g of isooctylaldehyde into the four-diameter bottle under stirring, and carrying out disproportionation reaction to obtain isooctoate;
(2) double decomposition reaction: dissolving 88.5 g of stannous chloride dihydrate in 1L of water, adding a stannous chloride solution into the isooctoate prepared in the step (1) under the nitrogen protection atmosphere, controlling the reaction temperature to be 65 ℃, stirring for 30min, carrying out double decomposition reaction, standing for layering, collecting upper mother liquor, carrying out reduced pressure distillation for 5mmHg, controlling the distillation temperature to be 200 ℃, continuing for 10min, stopping distillation, breaking the nitrogen, reducing the nitrogen to be 25-30 ℃ under the nitrogen protection, and filtering to obtain clear, transparent and viscous liquid, namely stannous isooctoate, wherein the content of stannous in the prepared stannous isooctoate is 29%, and the process yield is 92.5%.
Example 3
(1) Disproportionation reaction: adding 98.13g of sodium hydroxide with the mass fraction of 60% into a 500ml four-diameter bottle with a stirrer, controlling the reaction temperature to be 80 ℃, slowly adding 100g of isooctylaldehyde into the four-diameter bottle under stirring, and carrying out disproportionation reaction to obtain isooctoate;
(2) double decomposition reaction: dissolving 88.5 g of stannous chloride dihydrate in 1L of water, adding a stannous chloride solution into the isooctoate prepared in the step (1) under the nitrogen protection atmosphere, controlling the reaction temperature to be 90 ℃, stirring for 30min, carrying out double decomposition reaction, standing for layering, collecting upper mother liquor, carrying out reduced pressure distillation for 10mmHg, controlling the distillation temperature to be 250 ℃, continuing for 10min, stopping distillation, breaking the nitrogen, reducing the nitrogen to be 25-30 ℃ under the nitrogen protection, and filtering to obtain clear, transparent and viscous liquid, namely stannous isooctoate, wherein the content of stannous in the prepared stannous isooctoate is 31%, and the process yield is 91.8%.
Test for catalytic Performance
EXAMPLE 4 preparation of isooctanol isooctanoate as catalyst
150g of isooctanoic acid and 100g of isooctanol are added into a 500ml four-diameter bottle, 1.9g of stannous isooctenoate prepared in the example 1 is taken as a catalyst, the stannous isooctenoate is added into the four-diameter bottle, the temperature is raised to 225-240 ℃, and the reaction is carried out for 3.5 hours. The light fraction is removed under negative pressure, washed with sodium hydroxide solution and then with distilled water to obtain 173.2g of isooctyl isooctanoate, the yield of isooctyl isooctanoate is 99.7%.
EXAMPLE 5 preparation of triethylene glycol Diethyloctanoate as catalyst
150g of isooctanoic acid and 55g of triethylene glycol are added into a 500ml four-diameter bottle, 1.9g of stannous isooctanoate in example 2 is taken as a catalyst, stannous isooctanoate is added into the four-diameter bottle, the temperature is raised to 225-240 ℃, the reaction is carried out for 5.5 hours, light components are removed under negative pressure, and the mixture is washed by alkali and water to obtain 120.3g of triethylene glycol diethyl octanoate, wherein the yield of the triethylene glycol diethyl octanoate is 80.88%.
EXAMPLE 6 preparation of monolaurin as catalyst
166g of lauric acid and 74g of glycerol are added into a four-diameter bottle of 500ml, 2.4g of stannous isooctenoate prepared in the embodiment 3 is taken as a catalyst, the temperature is raised to 225-240 ℃, the vacuum degree is 50mmHg, the water temperature of a condenser is 65 ℃, after 2 hours of reaction, the vacuum degree is gradually increased, and the reaction is continued for 3.5 hours under 5 mmHg. Cooling to 70 ℃, adding 20g of sodium hydroxide solution with the mass fraction of 40%, stirring for 5 minutes, standing for layering, pouring out supernatant, controlling the temperature to be 70 ℃, washing twice with saturated saline solution, decompressing and dehydrating, and filtering at the constant temperature to obtain 192g of lauric acid monoglyceride with the yield of 87.6%.
Comparative example 1
150g of isooctanoic acid and 100g of isooctanol are added into a 500ml four-diameter bottle, the temperature is raised to 225-240 ℃, and the reaction is carried out for 3.5 hours. The light fraction is removed under negative pressure, and after alkali washing by using sodium hydroxide solution, 125.8.2g of isooctyl isooctanoate is obtained by washing by using distilled water, and the yield of isooctyl isooctanoate is 71.98%.
Comparative example 2
Adding 150g of isooctanoic acid and 55g of triethylene glycol into a 500ml four-diameter bottle, heating to 225-240 ℃, reacting for 5.5 hours, removing light components under negative pressure, and carrying out alkali washing and water washing to obtain 101.23g of triethylene glycol diethyl caprylate, wherein the yield of the triethylene glycol diethyl caprylate is 68.06%.
Comparative example 3
166g of lauric acid and 74g of glycerol are added into a four-diameter bottle of 500ml, the temperature is raised to 225-240 ℃, the vacuum degree is 50mmHg, the water temperature of a condenser is 65 ℃, after 2 hours of reaction, the vacuum degree is gradually increased, and the reaction is continued for 3.5 hours under 5 mmHg. Cooling to 70 ℃, adding 20g of sodium hydroxide solution with the mass fraction of 40%, stirring for 5 minutes, standing for layering, pouring out supernatant, controlling the temperature to be 70 ℃, washing twice with saturated saline solution, decompressing and dehydrating, and filtering at the constant temperature to obtain 168.60g of lauric monoglyceride, wherein the yield of the lauric monoglyceride is 76.92%.
And (4) experimental conclusion: wherein comparative example 1 is isooctyl isooctanoate prepared without adding stannous isooctenoate, comparative example 2 is triethylene glycol di-n-caprylate prepared without adding stannous isooctenoate, and comparative example 3 is glycerol monolaurate prepared without adding stannous isooctenoate.
From examples 1 to 3, the stannous isooctanoate prepared by the method is a new catalyst for polyester reaction, and is prepared by carrying out disproportionation reaction on isooctenal serving as a reactant in an alkaline solution to generate isooctoate, adding stannous chloride, and carrying out double decomposition reaction, wherein the tin content of the prepared stannous isooctanoate is more than 29%.
As can be seen from comparative example 1 and example 4, the yield of isooctyl isooctanoate prepared after adding stannous isooctanoate is higher than that of isooctyl isooctanoate without adding stannous isooctanoate, which fully shows that stannous isooctanoate can be used as a catalyst to accelerate the esterification reaction rate of isooctanoic acid and isooctanol.
As can be seen from comparative example 2 and example 5, the yield of triethylene glycol diethyl octanoate obtained after adding stannous isooctenoate is higher than that of triethylene glycol diethyl octanoate without adding stannous isooctenoate, which fully indicates that stannous isooctenoate can be used as a catalyst to accelerate the esterification reaction rate of isooctanoic acid and triethylene glycol.
As can be seen from comparative example 3 and example 5, the yield of the prepared lauric monoglyceride after the addition of stannous isooctenoate was higher than that of the lauric monoglyceride without the addition of stannous isooctenoate, which fully indicates that stannous isooctenoate can be used as a catalyst to accelerate the esterification reaction of lauric acid and glycerol.
The stannous isooctanoate prepared by the method shows good catalytic activity to polyester reaction, can be used as a catalyst in the polyester reaction, and when the stannous isooctanoate is used as a catalyst for preparing isooctanol isooctanoate, the conversion rate of isooctanol isooctanoate can reach 99.7 percent, so that the economic benefit is obviously improved, and the stannous isooctanoate is suitable for industrial production.
In addition, the stannous isooctenoate prepared by the invention contains isooctanol and unreacted isooctenal generated by disproportionation reaction, and the isooctanol and the unreacted isooctenal are removed by organic phase vacuum distillation. Therefore, the post-treatment process is simple, free of three wastes, safe, nontoxic and suitable for industrial production.
The above description is only exemplary of the present application and should not be taken as limiting the present application, as any modification, equivalent replacement, or improvement made within the spirit and principle of the present application should be included in the protection scope of the present application.
Claims (9)
1. A preparation method of stannous isooctoate is characterized by comprising the following steps:
(1) disproportionation reaction: adding the alkaline solution into a reaction kettle, controlling the reaction temperature, slowly adding isooctenal into the reaction kettle under stirring, and carrying out disproportionation reaction to obtain isooctoate;
(2) double decomposition reaction: adding a stannous chloride solution under the protection of nitrogen, stirring, controlling the reaction temperature, carrying out double decomposition reaction, standing for layering, collecting the upper mother liquor, carrying out reduced pressure distillation, controlling the distillation temperature and time, reducing the nitrogen to be empty after the distillation is finished, reducing the nitrogen to 25-30 ℃ under the protection of the nitrogen, and filtering to obtain the stannous isooctoate.
2. The method of claim 1, wherein the alkaline solution is one of sodium hydroxide and potassium hydroxide.
3. The method for preparing stannous isooctoate according to claim 1, wherein the mass fraction of the alkaline solution is 30-50%.
4. The method for preparing stannous isooctoate of claim 1, wherein the molar ratio of the alkaline solution to isooctenal is 1 (1-5).
5. The method for preparing stannous isooctoate according to claim 1, wherein the disproportionation reaction temperature is 25-80 ℃.
6. The method for preparing stannous isooctoate according to claim 1, wherein the metathesis reaction temperature is 40-90 ℃.
7. The method for preparing stannous isooctoate according to claim 1, wherein the vacuum degree of the negative pressure distillation is 1-10 mmHg.
8. The method for preparing stannous isooctoate according to claim 1, wherein the distillation temperature is 150-250 ℃ and the distillation time is 20-40 min.
9. Use of stannous isooctenoate prepared according to claims 1 to 8, characterized in that it is used as catalyst in polyester reactions.
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| GB1003201A (en) * | 1963-03-15 | 1965-09-02 | Ici Ltd | Improvements in or relating to the manufacture of polyurethanes |
| CN1015058B (en) * | 1989-02-05 | 1991-12-11 | 浙江省明矾石综合利用研究所 | Preparation method of 2-ethyl stannous caproate |
| CN1059198C (en) * | 1996-10-17 | 2000-12-06 | 云南锡业公司研究设计院 | Method for one-step manufacture of stannous caprylate |
| CN111499661A (en) * | 2020-04-13 | 2020-08-07 | 盘锦洪鼎化工有限公司 | Preparation method of tin oxide complex diisooctanoate |
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Denomination of invention: A Preparation Method and Application of Tin Isooctenate Effective date of registration: 20230911 Granted publication date: 20220614 Pledgee: Weifang Jinma road sub branch of Bank of Weifang Co.,Ltd. Pledgor: JIAYIJIA BIOTECH Inc. Registration number: Y2023980056111 |