CN103833785A - Synthetic method for phosphate ester - Google Patents
Synthetic method for phosphate ester Download PDFInfo
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- CN103833785A CN103833785A CN201310720057.4A CN201310720057A CN103833785A CN 103833785 A CN103833785 A CN 103833785A CN 201310720057 A CN201310720057 A CN 201310720057A CN 103833785 A CN103833785 A CN 103833785A
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Abstract
The invention relates to the technical field of chemical synthesis, and particularly relates to a synthetic method for phosphate ester. The synthetic method comprises the steps of subjecting phosphorus pentoxide and primary alcohol to an esterification reaction in an organic solvent; and then hydrolyzing and extracting to obtain the phosphate ester. The phosphate ester is prepared by a phosphorus pentoxide solvent method. The reaction is mild, so that the problem of non-uniform reaction system and too vigorous local reaction can be effectively prevented, thereby preventing coking and carbonization phenomena of the phosphate ester. Besides, by controlling reaction conditions, particularly a reaction solvent, a reaction temperature and a reaction time, a proportion of monoester to diester in a product can be controlled; repeatability is good; the content of monoester in the product is 48-52%; and the method is suitable for preparing excellent rust-preventative oil. By controlling a hydrolysis time, a hydrolysis temperature and water use amount and by using diethyl ether as an extracting agent, reaction yield can be obviously increased; and yield can reach as high as 80-90%. Besides, control of a feeding manner of the primary alcohol can also increase the yield and influence the proportion of the monoester to the diester.
Description
Technical field
The present invention relates to chemosynthesis technical field, relate in particular to a kind of synthetic method of phosphoric acid ester.
Background technology
Phosphoric acid ester is carried out esterification by the organic compound of hydroxyl and phosphorization agent and is made.Because phosphoric acid is triprotic acid, therefore according to the difference of substituted hydrocarbon radical number, phosphoric acid ester can be divided into uncle's phosphoric acid ester (phosphoric acid one ester, alkyl phosphoric acid), secondary phosphoric acid ester (phosphodiester) and tertiary phosphoric acid ester (phosphotriester).The method of existing synthetic phosphoric acid ester is a lot, can be divided into Vanadium Pentoxide in FLAKES type, phosphorus trihalide type, three oxyhalogen phosphorus types, phosphatic type and tetra-sodium type etc. according to the difference of phosphorization agent, but it is synthetic that major part is only suitable for carrying out a small amount of, can not amplify production, cannot realize industrialization.
Be easy to get because Vanadium Pentoxide in FLAKES type is relatively inexpensive in phosphorization agent, do not need specific installation etc., be most widely used.But existing Vanadium Pentoxide in FLAKES type adopts solventless method synthetic conventionally, there are some shortcomings in the method, is mainly the inhomogeneous and too violent problem of local reaction of reaction system, easily cause a large amount of coking of phosphoric acid ester, carbonization, and productive rate only has 50-60% conventionally; Under the same terms, single dibasic acid esters proportional difference of the synthetic phosphoric acid ester of different batches is very large, poor reproducibility.Therefore, the existing exploitation one of being badly in need of is suitable for suitability for industrialized production, the synthetic method of the controlled phosphoric acid ester of single dibasic acid esters ratio.
Summary of the invention
It is controlled that the technical problem to be solved in the present invention is to provide a kind of single dibasic acid esters ratio, is suitable for industrial production, and reaction temperature and, the synthetic method of phosphoric acid ester that productive rate is high.
For achieving the above object, the present invention is by the following technical solutions:
A synthetic method for phosphoric acid ester, comprises the following steps:
(1) mix: by Vanadium Pentoxide in FLAKES be placed in organic solvent and stir make its disperse, then add primary alconol and be stirred to liquid by oyster white become clarification, obtain mixed solution;
Described primary alconol is the primary alconol that contains 4-16 carbon atom.
Described Vanadium Pentoxide in FLAKES is any ratio with the ratio of the amount of substance of primary alconol; Preferably, Vanadium Pentoxide in FLAKES is 1:1.9-3 with the ratio of the amount of substance of primary alconol.
Preferably, primary alconol is divided into some part, and primary alconol is added in organic solvent by part, and two parts of primary alconols feed intake be spaced apart 10-15min.More preferably, primary alconol is divided into four parts.
Preferably, described organic solvent is in arbitrary in toluene, ethyl acetate and tetrahydrofuran (THF).The amount of substance of described Vanadium Pentoxide in FLAKES and the volume ratio of organic solvent are 0.1-2mol/L.
(2) esterification: mixed solution is heated to 20-120 ℃, and insulation reaction 2-4h, obtain reaction solution; Preferably, mixed solution is heated to 50-75 ℃, and insulation reaction 3h.
(3) hydrolysis: add water to obtain hydrolysis reaction liquid in reaction solution, then heating hydrolysis reaction solution makes its temperature higher than reaction solution 5-15 ℃, insulation reaction 0.5-1h; Preferably, make the temperature of hydrolysis reaction liquid higher than 10 ℃ of reaction solutions, water is deionized water, the 1-10% of the volume that the volume of deionized water is the organic solvent that adds in step (1);
(4) separate: after hydrolysis reaction liquid is cooled to room temperature, add the weak caustic solution of water or PH=8-11, and more than standing 10min, then must extract mixed solution with extraction agent phosphoric acid extraction ester, will after the solvent evaporation in extraction mixed solution, obtain finished product.Described extraction agent is preferably ether or ethyl acetate.Preferably, described water is deionized water, and the volume of water is the long-pending 0.2-5 of hydrolysis reaction liquid times.
Compared with prior art, the invention has the beneficial effects as follows: the present invention adopts Vanadium Pentoxide in FLAKES solvent method to prepare phosphoric acid ester, reaction temperature and, can effectively prevent the inhomogeneous and too violent problem of local reaction of reaction system, thereby avoid phosphoric acid ester coking and carbonization phenomenon.In addition, by controlling each reaction conditions, especially reaction solvent, temperature of reaction and reaction times, in product the ratio of single dibasic acid esters stablize controlled, favorable reproducibility, in product, the content of monoesters is 48-52%, is applicable to prepare good slushing oil.The consumption of controlled hydrolysis time, hydrolysis temperature, water, and use ether as extraction agent, can obviously improve reaction yield, productive rate is up to 80-90%.The feeding mode of controlling primary alconol also can improve the ratio of productive rate and the single dibasic acid esters of impact.
Embodiment
In order to more fully understand technology contents of the present invention, below in conjunction with specific embodiment, technical scheme of the present invention is described further and is illustrated.
Embodiment 1-11
Reactant in embodiment 1-11 and organic solvent are all identical, are 0.1mol Vanadium Pentoxide in FLAKES, 0.2mol n-Octanol and 100mL toluene.
Preparation method is as follows:
Mix: Vanadium Pentoxide in FLAKES is placed in to beaker, in beaker, adds toluene, use magnetic stirring apparatus to stir, Vanadium Pentoxide in FLAKES is fully disperseed; Then n-Octanol is divided into four parts and add (in embodiment 11, n-Octanol once all adds in beaker) in beaker by part, be 10min the interval time that two parts of n-Octanols add, and continues to stir after 15min, and the solution in beaker becomes clarification by oyster white.
Esterification: the solution in beaker is transferred in 250mL bottle with two necks and by bottle with two necks and is placed in oil bath, oil bath is heated to certain temperature, maintain this thermotonus for some time.
Hydrolysis: add deionized water in bottle with two necks, then oil bath heating is increased to certain temperature and is hydrolyzed.
Separate: complete and bottle with two necks is shifted out to oil bath after hydrolysis and make hydrolysis reaction liquid be cooled to room temperature, then add appropriate amount of deionized water also more than standing 15min, liquid in bottle with two necks is poured in separating funnel and with extraction agent extraction three times, merge extraction agent layer, use Rotary Evaporators (underpressure distillation) to be spin-dried for solvent, obtain product.(volume of deionized water is the long-pending 0.2-5 of hydrolysis reaction liquid times, preferably 1 times)
The concrete reaction conditions of embodiment 1-11 is as shown in the table:
Embodiment 12-21
In embodiment 12-21, the preparation method of phosphoric acid ester is as follows:
Mix: Vanadium Pentoxide in FLAKES is placed in to beaker, in beaker, adds 100mL organic solvent, use magnetic stirring apparatus to stir, Vanadium Pentoxide in FLAKES is fully disperseed; Then primary alconol is divided into four parts and add in beaker by part, be 10min the interval time that two parts of primary alconols add, and continues to stir after 15min, and the solution in beaker becomes clarification by oyster white.
Esterification: the solution in beaker is transferred in 250mL bottle with two necks and by bottle with two necks and is placed in oil bath, oil bath is heated to 65 ℃ (embodiment 20-21 is 75 ℃), the reaction times that maintains this thermotonus 3h(embodiment 19-21 is 3.5h).
Hydrolysis: add 10mL deionized water (deionized water of embodiment 19-21 is 5mL) in bottle with two necks, then oil bath is heated to 75 ℃ (embodiment 20-21 is 85 ℃), hydrolysis 1h.
Separate: complete and bottle with two necks is shifted out to oil bath after hydrolysis and make hydrolysis reaction liquid be cooled to room temperature, then add appropriate amount of deionized water (embodiment 19-21 adds the NaOH solution of pH=10) also more than standing 15min, liquid in bottle with two necks is poured in separating funnel and use extracted with diethyl ether three times, combined ether layer, use Rotary Evaporators (underpressure distillation) to be spin-dried for solvent, obtain product.
Reactant in embodiment 12-21 and solvent and consumption thereof are as shown in the table:
| ? | Phosphorization agent | Alcohol | Organic solvent |
| Embodiment 12 | P 2O 5，0.1mol | N-Octanol, 0.19mol | Toluene, 100mL |
| Embodiment 13 | P 2O 5，0.1mol | N-Octanol, 0.21mol | Toluene, 100mL |
| Embodiment 14 | P 2O 5，0.1mol | N-Octanol, 0.2mol | Ethyl acetate, 100mL |
| Embodiment 15 | P 2O 5，0.1mol | N-Octanol, 0.2mol | Tetrahydrofuran (THF), 100mL |
| Embodiment 16 | P 2O 5，0.1mol | N-Octanol, 0.2mol | Acetone, 100mL |
| Embodiment 17 | P 2O 5，0.1mol | N-Octanol, 0.2mol | Acetonitrile, 100mL |
| Embodiment 18 | P 2O 5，0.1mol | Propyl carbinol, 0.2mol | Toluene, 100mL |
| Embodiment 19 | P 2O 5，0.1mol | N-Heptyl alcohol, 0.2mol | Toluene, 100mL |
| Embodiment 20 | P 2O 5，0.1mol | N-dodecanol, 0.3mol | Toluene, 100mL |
| Embodiment 21 | P 2O 5，0.1mol | Positive hexadecanol, 0.3mol | Toluene, 100mL |
Productive rate, monoester content and the product appearance of the prepared phosphoric acid ester of embodiment 1-21 are as shown in the table:
| ? | Productive rate (%) | Monoester content (%) | Product appearance |
| Embodiment 1 | 78 | 35 | Deep yellow liquid |
| Embodiment 2 | 78 | 38 | Light yellow transparent liquid |
| Embodiment 3 | 85 | 48 | Colourless transparent liquid |
| Embodiment 4 | 90 | 50 | Colourless transparent liquid |
| Embodiment 5 | 60 | 65 | Colourless transparent liquid |
| Embodiment 6 | 40 | 70 | Colourless transparent liquid |
| Embodiment 7 | 67 | 50 | Light yellow transparent liquid |
| Embodiment 8 | 70 | 42 | Colourless transparent liquid |
| Embodiment 9 | 65 | 50 | Colourless transparent liquid |
| Embodiment 10 | 20 | 50 | Colourless transparent liquid |
| Embodiment 11 | 70 | 45 | Colourless transparent liquid |
| Embodiment 12 | 88 | 55 | Colourless transparent liquid |
| Embodiment 13 | 90 | 50 | Colourless transparent liquid |
| Embodiment 14 | 75 | 50 | Colourless transparent liquid |
| Embodiment 15 | 60 | 50 | Colourless transparent liquid |
| Embodiment 16 | 40 | 50 | Colourless transparent liquid |
| Embodiment 17 | 40 | 50 | Colourless transparent liquid |
| Embodiment 18 | 90 | 45 | Colourless transparent liquid |
| Embodiment 19 | 85 | 48 | Colourless transparent liquid |
| Embodiment 20 | 80 | 54 | White solid |
| Embodiment 21 | 80 | 57 | White solid |
From above data, organic solvent has direct impact to the productive rate of reaction, but on the not directly impact of the ratio of single dibasic acid esters in product, as embodiment 14-17, substitute toluene with ethyl acetate, tetrahydrofuran (THF), acetone and acetonitrile respectively, productive rate all obviously reduces, even use acetone and acetonitrile as the reaction solvent in esterif iotacation step, productive rate is down to 40% by 90%, but in product, single dibasic acid esters is 1:1 than still, and therefore selecting of reaction solvent has important impact to reaction yield.The selection of extraction agent is also very important on the impact of productive rate,, can only obtain 65% productive rate, and using methylene dichloride as extraction agent, only obtain 20% productive rate as extraction agent by ethyl acetate.
In addition, the consumption of water when esterification time, esterification temperature, hydrolysis time, hydrolysis, and the feeding mode of primary alconol all has material impact to reaction yield and single dibasic acid esters ratio.Temperature of reaction rising can make monoester content obviously reduce, and products therefrom, for the preparation of rust protection liquid, is unfavorable for the rustless property of rust protection liquid; Temperature of reaction is too low, is unfavorable for the carrying out of reaction, and generates more monoesters, as described in Example 6.Temperature of reaction also can have impact to the color on product, and this is because partial organic substances high temperature cabonization causes product colouring.
Different straight chain primary alcohols can affect the ratio of single dibasic acid esters in product, when the alkyl chain of straight chain primary alcohol more in short-term, as propyl carbinol (embodiment 18), can cause the content of diester to increase; On the contrary, when alkyl chain cross compared with time (cetyl alcohol, embodiment 21), due to space steric effect, can tend to the monoesters that generate more; And product is also along with the growth of carbochain progressively becomes solid from liquid.
Embodiment 22
Take embodiment 4 as reference, will react and amplify 100 times, by 10mol, the Vanadium Pentoxide in FLAKES of 1.42Kg and 20mol, 2.6046kg n-Octanol reacts.
Mix: Vanadium Pentoxide in FLAKES is placed in to container, in container, adds 10L organic solvent, use agitator to stir, Vanadium Pentoxide in FLAKES is fully disperseed; Then n-Octanol is divided into four parts and add in container by part, be 10min the interval time that two parts of n-Octanols add, and continues to stir after 15min, and the solution in container becomes clarification by oyster white.
Esterification: the solution in container is transferred in the retort of twoport and reacting by heating tank to 65 ℃, maintains this thermotonus 3h.
Hydrolysis: add 1L deionized water in retort, then continue heating and make retort be warming up to 75 ℃, hydrolysis 1h.
Separate: after completing hydrolysis, stop retort heating, make its liquid be cooled to room temperature, then add 12L deionized water also more than standing 15min, then liquid extracted with diethyl ether three times in retort, combined ether layer, and underpressure distillation, obtain being the phosphoric acid ester product of colourless transparent liquid, productive rate 87%, monoester content is 50.
Embodiment 23-27
Take embodiment 4 as reference, will react and amplify 10000 times, by 1000mol, the Vanadium Pentoxide in FLAKES of 142Kg and 2000mol, 260.46kg n-Octanol reacts, and the concrete synthesis step of embodiment 23-27 is as follows:
Mix: Vanadium Pentoxide in FLAKES is placed in to container, in container, adds 1000L organic solvent, use agitator to stir, Vanadium Pentoxide in FLAKES is fully disperseed; Then n-Octanol is divided into four parts and add in container by part, be 10min the interval time that two parts of n-Octanols add, and continues to stir after 15min, and the solution in container becomes clarification by oyster white.
Esterification: the solution in container is transferred in the retort of twoport and reacting by heating tank to 65 ℃, maintains this thermotonus 3h.
Hydrolysis: add 100L deionized water in retort, then continue heating and make retort be warming up to 75 ℃, hydrolysis 1h.
Separate: after completing hydrolysis, stop, to retort heating, making its liquid be cooled to room temperature, then add 1200L deionized water and more than standing 15min, follow liquid extracted with diethyl ether three times in retort, combined ether layer, and underpressure distillation, obtain phosphoric acid ester product.
Productive rate, monoester content and the product appearance of the prepared phosphoric acid ester of embodiment 23-27 are as shown in the table:
| ? | Productive rate (%) | Monoester content (%) | Product appearance |
| Embodiment 23 | 89 | 50 | Colourless transparent liquid |
| Embodiment 24 | 83 | 48 | Colourless transparent liquid |
| Embodiment 25 | 87 | 50 | Colourless transparent liquid |
| Embodiment 26 | 80 | 49 | Colourless transparent liquid |
| Embodiment 27 | 85 | 52 | Colourless transparent liquid |
From the experimental data of above embodiment 22-27, amplify the reaction of embodiment 4, single dibasic acid esters ratio in products therefrom is close, monoester content all between 48-52%, the favorable reproducibility of experiment, and productive rate is all more than 80%, present method is suitable for suitability for industrialized production, prepared phosphoric acid ester can be used for preparing good rust protection liquid (for the preparation of the phosphoric acid ester of rust protection liquid, its single dibasic acid esters ratio more approaches 1:1, and the rustless property of prepared rust protection liquid is just better).
Phosphoric acid ester prepared by embodiment 4 is mixed with rust protection liquid.
Compound method: the phosphoric acid ester that is 2% by mass percent, 8% trolamine and 90% deionized water mix and stir, and solution is transparent clarification shape, forms phosphoric acid ester strong solution.Get mass percent and be 5% phosphoric acid ester strong solution and mix and stir with 95% deionized water, obtain rust protection liquid.
The performance test of rust protection liquid:
Method one: respectively zinc alloy sheet good surface finish and aluminum alloy sheet are immersed in rust protection liquid, and be placed in the baking oven of 55 ℃, observe the surface of zinc alloy sheet and aluminum alloy sheet after 24 hours whether dimmed or occur rust staining.
Method two: respectively zinc alloy sheet good surface finish and aluminum alloy sheet are immersed in rust protection liquid, soak in the baking oven of taking out and be placed in 55 ℃ after ten minutes, observe the surface of zinc alloy sheet and aluminum alloy sheet after 24 hours whether dimmed or occur rust staining.
Test result:
Through zinc alloy sheet and the aluminum alloy sheet of above two kinds of methods test, after 24 hours, alloy slice surface all occurs without any rust staining, also not dimmed.
Test result shows, the rust protection liquid that the phosphoric acid ester of being synthesized by embodiment 4 is mixed with all can embody good rustless property for zinc alloy and aluminium alloy.
According to the method for above preparation rust protection liquid, phosphoric acid ester synthetic embodiment 19-27 is mixed with respectively to rust protection liquid, and tests the rustless property of rust protection liquid with identical method.After 24 hours, alloy slice surface all occurs without any rust staining, also not dimmed.Test result demonstration, the rust protection liquid that the phosphoric acid ester of being synthesized by embodiment 19-27 is mixed with, can embody good rustless property equally for zinc alloy and aluminium alloy.
The above only further illustrates technology contents of the present invention with embodiment, so that reader is easier to understand, but does not represent that embodiments of the present invention only limit to this, and any technology of doing according to the present invention is extended or recreation, is all subject to protection of the present invention.
Claims (10)
1. a synthetic method for phosphoric acid ester, is characterized in that, comprises the following steps:
(1) mix: by Vanadium Pentoxide in FLAKES be placed in organic solvent and stir make its disperse, then add primary alconol and be stirred to liquid by oyster white become clarification, obtain mixed solution; Described Vanadium Pentoxide in FLAKES is any ratio with the ratio of the amount of substance of primary alconol;
(2) esterification: mixed solution is heated to 20-120 ℃, and insulation reaction 2-4h, obtain reaction solution;
(3) hydrolysis: add water to obtain hydrolysis reaction liquid in reaction solution, then heating hydrolysis reaction solution makes its temperature higher than reaction solution 5-15 ℃, insulation reaction 0.5-1h; The volume of described water is the 1-10% of organic solvent volume described in step (1);
(4) separate: after hydrolysis reaction liquid is cooled to room temperature, add the weak caustic solution of water or pH=8-11, and more than standing 10min, then must extract mixed solution with extraction agent phosphoric acid extraction ester, will after the solvent evaporation in extraction mixed solution, obtain finished product.
2. a kind of synthetic method of phosphoric acid ester according to claim 1, is characterized in that, described Vanadium Pentoxide in FLAKES is 1:1.9-3 with the ratio of the amount of substance of primary alconol.
3. a kind of synthetic method of phosphoric acid ester according to claim 2, is characterized in that, primary alconol described in step (1) is divided into some parts, adds in organic solvent by part, and what two parts of primary alconols fed intake is spaced apart 10-15min.
4. a kind of synthetic method of phosphoric acid ester according to claim 3, is characterized in that, described primary alconol is divided into four parts.
5. a kind of synthetic method of phosphoric acid ester according to claim 3, is characterized in that, in described step (2), mixed solution is heated to 50-75 ℃, and insulation reaction 3h.
6. a kind of synthetic method of phosphoric acid ester according to claim 5, is characterized in that, organic solvent described in step (1) is in arbitrary in toluene, ethyl acetate and tetrahydrofuran (THF).
7. a kind of synthetic method of phosphoric acid ester according to claim 6, is characterized in that, the amount of substance of described Vanadium Pentoxide in FLAKES and the volume ratio of organic solvent are 0.1-2mol/L.
8. a kind of synthetic method of phosphoric acid ester according to claim 6, is characterized in that, described in step (4), extraction agent is ether or ethyl acetate.
9. a kind of synthetic method of phosphoric acid ester according to claim 8, is characterized in that, the volume of water described in step (4) be the long-pending 0.2-5 of hydrolysis reaction liquid doubly.
10. according to the synthetic method of a kind of phosphoric acid ester described in claim 1-9 any one, it is characterized in that, described primary alconol is the primary alconol that contains 4-16 carbonatoms.
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| CN109158049A (en) * | 2018-08-20 | 2019-01-08 | 安徽嘉智信诺化工股份有限公司 | A kind of synthesis technology of phosphate-type surfactant |
| US10301334B1 (en) | 2018-02-14 | 2019-05-28 | Far Eastern New Century Corporation | Method for preparing stabilizer containing phosphate-ester |
| CN113512061A (en) * | 2021-08-24 | 2021-10-19 | 沈阳华仑润滑油添加剂有限公司 | Preparation method of phosphate |
| CN115043873A (en) * | 2022-05-09 | 2022-09-13 | 浙江省粮食科学研究所有限责任公司 | Preparation method of water-soluble higher fatty alcohol potassium phosphate |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10301334B1 (en) | 2018-02-14 | 2019-05-28 | Far Eastern New Century Corporation | Method for preparing stabilizer containing phosphate-ester |
| CN109158049A (en) * | 2018-08-20 | 2019-01-08 | 安徽嘉智信诺化工股份有限公司 | A kind of synthesis technology of phosphate-type surfactant |
| CN113512061A (en) * | 2021-08-24 | 2021-10-19 | 沈阳华仑润滑油添加剂有限公司 | Preparation method of phosphate |
| CN115043873A (en) * | 2022-05-09 | 2022-09-13 | 浙江省粮食科学研究所有限责任公司 | Preparation method of water-soluble higher fatty alcohol potassium phosphate |
| CN115043873B (en) * | 2022-05-09 | 2024-06-14 | 浙江省粮食科学研究所有限责任公司 | Preparation method of water-soluble potassium phosphate of higher fatty alcohol |
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Application publication date: 20140604 |