CN105461748A - Method for preparing di(isooctyl) phosphate from tri-iso-octyl phosphate through phase-transfer catalytic hydrolysis - Google Patents
Method for preparing di(isooctyl) phosphate from tri-iso-octyl phosphate through phase-transfer catalytic hydrolysis Download PDFInfo
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- CN105461748A CN105461748A CN201510911559.4A CN201510911559A CN105461748A CN 105461748 A CN105461748 A CN 105461748A CN 201510911559 A CN201510911559 A CN 201510911559A CN 105461748 A CN105461748 A CN 105461748A
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- Prior art keywords
- phosphate
- isooctyl
- phase
- sodium hydroxide
- triisooctyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
Abstract
The invention provides a method for preparing di(isooctyl) phosphate from tri-iso-octyl phosphate through phase-transfer catalytic hydrolysis and relates to a preparation technology of di(isooctyl) phosphate. By means of improvement of a traditional technological process of hydrolysis of tri-iso-octyl phosphate, purposes of reducing the use amount of sodium hydroxide and the reaction temperature, shortening the reaction time and increasing the content and the yield of di(isooctyl) phosphate are achieved; the method has high practicability, and with the adoption of the technical scheme, the method has the benefits as follows: 1, the use amount of sodium hydroxide is reduced, and the production cost is reduced; 2, the reaction temperature is reduced, the reaction time is shorter, so that the content of byproducts is reduced, and the production cycle is shortened; 3, the content and the yield of di(isooctyl) phosphate are greatly increased.
Description
[technical field]
The present invention relates to a kind of di (isooctyl) phosphate technology of preparing, especially relate to a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate and prepare di (isooctyl) phosphate method.
[background technology]
Known, the commodity of the hydrolysate di (isooctyl) phosphate of triisooctyl phosphate are called P204, it is a kind of important phosphorous hydrometallurgical extraction agent, be widely used in coloured, metal extraction field, occupies irreplaceable status in the pollution-free novel technique be especially separated with rare earth simple substance at Separation of nickel and cobalt high purity rare earth oxide, extracted.
Industrial generally directly mixing with triisooctyl phosphate and the excessive sodium hydrate aqueous solution or solid sodium hydroxide reacts, in order to react fully, the temperature that usual needs are higher and longer time, when therefore making to produce, energy consumption is too high, production cycle is also relatively long, and the content of di (isooctyl) phosphate and yield lower.
[summary of the invention]
In order to overcome the deficiency in background technology, the invention discloses a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate and prepare di (isooctyl) phosphate method, the present invention is by improving the technological process of traditional triisooctyl phosphate hydrolysis, minimizing sodium hydroxide concentration is reached with this, reduce temperature of reaction, reduce the reaction times, improve the content of di (isooctyl) phosphate and the object of yield.
In order to realize described goal of the invention, the present invention adopts following technical scheme:
A kind of phase-transfer catalysis hydrolysis triisooctyl phosphate prepares di (isooctyl) phosphate method, adopt phase-transfer catalyst method, promote that the triisooctyl phosphate of oil phase and the sodium hydroxide of aqueous phase react, remove isooctyl alcohol obtain di (isooctyl) phosphate through washing, acidifying, washing, steaming again, concrete preparation method is as follows:
The first step, add triisooctyl phosphate, aqueous sodium hydroxide solution and alkylammonium salt catalyzer in the reactor, react under whipped state, wherein, the mol ratio of triisooctyl phosphate and sodium hydroxide is 1:(1 ~ 1.1), catalyst levels is 1 ~ 5% of triisooctyl phosphate amount of substance, and the mass concentration of sodium hydroxide solution is 15 ~ 45%, temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 2 ~ 5h;
Further, after completion of the reaction, first wash once, be separated and obtain not containing the organic phase of salinity, then organic phase hcl acidifying, after separatory, organic phase is washed, treat that water lotion is to pH=2 ~ 7, distillation organic phase, steams and obtains di (isooctyl) phosphate except after the isooctyl alcohol generated.
Described alkylammonium salt catalyzer is any one of the phase-transfer catalysts such as tetrabutylammonium iodide, trimethyl ammonium iodide, tetradecyltrimethylammonium ammonium iodide, Tetrabutyl amonium bromide, 4-butyl ammonium hydrogen sulfate, tri-n-octyl methyl ammonium chloride.
Described triisooctyl phosphate and the mol ratio of sodium hydroxide are 1:(1 ~ 1.1), catalyst levels is 1 ~ 5% of iso-octyl phosphonic acids di-isooctyl amount of substance, the massfraction of sodium hydroxide solution is 15 ~ 45%, and temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 2 ~ 5h.
The concrete grammar that described steaming removes isooctyl alcohol is: vacuum tightness 720 ~ 740mmHg underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol.
During described organic phase hcl acidifying, the mol ratio of hydrogenchloride and triisooctyl phosphate is (1 ~ 2): 1.
During described organic phase hcl acidifying, the massfraction of hydrochloric acid is 10 ~ 36.5%.
Owing to have employed technique scheme, the present invention has following beneficial effect:
A kind of phase-transfer catalysis hydrolysis triisooctyl phosphate of the present invention prepares di (isooctyl) phosphate method, by improving the technological process of traditional triisooctyl phosphate hydrolysis, minimizing sodium hydroxide concentration is reached with this, reduce temperature of reaction, reduce the reaction times, improve the content of di (isooctyl) phosphate and the object of yield; The present invention is practical, and by adopting technique scheme, the present invention has following beneficial effect: the first, and sodium hydroxide concentration reduces, and reduces production cost; The second, temperature of reaction reduces, and the reaction times is less, and by-products content is reduced, and the production cycle shortens; 3rd, content and the yield of di (isooctyl) phosphate raise greatly.
[embodiment]
By explanation the present invention that the following examples can be detailed, disclose object of the present invention and be intended to protect all technological improvements in the scope of the invention.
Described a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate prepares di (isooctyl) phosphate method, adopt phase-transfer catalyst method, promote that the triisooctyl phosphate of oil phase and the sodium hydroxide of aqueous phase react, remove isooctyl alcohol obtain di (isooctyl) phosphate through washing, acidifying, washing, steaming again, concrete preparation method is as follows:
The first step, add triisooctyl phosphate, aqueous sodium hydroxide solution and alkylammonium salt catalyzer in the reactor, react under whipped state, wherein, the mol ratio of triisooctyl phosphate and sodium hydroxide is 1:(1 ~ 1.1), catalyst levels is 1 ~ 5% of triisooctyl phosphate amount of substance, and the mass concentration of sodium hydroxide solution is 15 ~ 45%, temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 2 ~ 5h;
Further, after completion of the reaction, first wash once, be separated and obtain not containing the organic phase of salinity, then organic phase hcl acidifying, after separatory, organic phase is washed, treat that water lotion is to pH=2 ~ 7, distillation organic phase, steams and obtains di (isooctyl) phosphate except after the isooctyl alcohol generated.
Described alkylammonium salt catalyzer is any one of the phase-transfer catalysts such as tetrabutylammonium iodide, trimethyl ammonium iodide, tetradecyltrimethylammonium ammonium iodide, Tetrabutyl amonium bromide, 4-butyl ammonium hydrogen sulfate, tri-n-octyl methyl ammonium chloride.
Described triisooctyl phosphate and the mol ratio of sodium hydroxide are 1:(1 ~ 1.1), catalyst levels is 1 ~ 5% of iso-octyl phosphonic acids di-isooctyl amount of substance, the massfraction of sodium hydroxide solution is 15 ~ 45%, and temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 2 ~ 5h.
The concrete grammar that described steaming removes isooctyl alcohol is: vacuum tightness 720 ~ 740mmHg underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol.
During described organic phase hcl acidifying, the mol ratio of hydrogenchloride and triisooctyl phosphate is (1 ~ 2): 1.
During described organic phase hcl acidifying, the massfraction of hydrochloric acid is 10 ~ 36.5%.
The content of the di (isooctyl) phosphate prepared by existing preparation method and yield are all lower than 90%.
Embodiment 1
260.8g (0.6mol) triisooctyl phosphate is added successively in the 1000mL four-hole bottle that thermometer and condenser are housed, 88.0g (0.66mol) 30% sodium hydroxide solution and 6.6g (0.018mol) tetrabutylammonium iodide, be heated with stirring to 100 DEG C, insulation 3h, after completion of the reaction, first wash with 200g water, then organic phase 80.0g27% hcl acidifying, be washed to pH=3, (vacuum tightness 720 ~ 740mmHg) underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol, finally obtain the hydrolysate di (isooctyl) phosphate of triisooctyl phosphate, quality is 186.4g, yield is 95.1%, gas-chromatography content 98.7%, the yield of the di (isooctyl) phosphate described in this patent, all calculate gained with triisooctyl phosphate.
Embodiment 2
By the method for example 1, catalyzer changes trimethyl ammonium iodide into, and its charging capacity is 6.4g (0.018mol), and other conditions are constant, obtains product 187.4g, yield 94.8%, and gas chromatographic purity is 97.9%.
Embodiment 3
By the method for example 1, catalyzer changes Tetradecyl Trimethyl Ammonium Bromide into, and its charging capacity is 6.1g (0.018mol), and other conditions are constant, obtains product 186.0g, yield 94.5%, and gas chromatographic purity is 98.3%.
Embodiment 4
By the method for example 1, catalyzer changes Tetrabutyl amonium bromide into, and its charging capacity is 5.8g (0.018mol), and other conditions are constant, obtains product 186.6g, yield 95.0%, and gas chromatographic purity is 98.5%.
Embodiment 5
By the method for example 1, catalyzer changes 4-butyl ammonium hydrogen sulfate into, and its charging capacity is 6.1g (0.018mol), and other conditions are constant, obtains product 187.5g, yield 94.5%, and gas chromatographic purity is 97.5%.
Embodiment 6
By the method for example 1, catalyzer changes tri-n-octyl methyl ammonium chloride into, and its charging capacity is 7.3g (0.018mol), and other conditions are constant, obtains product 188.5g, yield 95.0%, and gas chromatographic purity is 97.5%.
Part not in the detailed description of the invention is prior art.
Claims (6)
1. a phase-transfer catalysis hydrolysis triisooctyl phosphate prepares di (isooctyl) phosphate method, it is characterized in that: adopt phase-transfer catalyst method, promote that the triisooctyl phosphate of oil phase and the sodium hydroxide of aqueous phase react, remove isooctyl alcohol obtain di (isooctyl) phosphate through washing, acidifying, washing, steaming again, concrete preparation method is as follows:
The first step, add triisooctyl phosphate, aqueous sodium hydroxide solution and alkylammonium salt catalyzer in the reactor, react under whipped state, wherein, the mol ratio of triisooctyl phosphate and sodium hydroxide is 1:(1 ~ 1.1), catalyst levels is 1 ~ 5% of triisooctyl phosphate amount of substance, and the mass concentration of sodium hydroxide solution is 15 ~ 45%, temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 2 ~ 5h;
Further, after completion of the reaction, first wash once, be separated and obtain not containing the organic phase of salinity, then organic phase hcl acidifying, after separatory, organic phase is washed, treat that water lotion is to pH=2 ~ 7, distillation organic phase, steams and obtains di (isooctyl) phosphate except after the isooctyl alcohol generated.
2. a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate according to claim 1 prepares di (isooctyl) phosphate method, it is characterized in that: described alkylammonium salt catalyzer is any one of the phase-transfer catalysts such as tetrabutylammonium iodide, trimethyl ammonium iodide, tetradecyltrimethylammonium ammonium iodide, Tetrabutyl amonium bromide, 4-butyl ammonium hydrogen sulfate, tri-n-octyl methyl ammonium chloride.
3. a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate according to claim 1 prepares di (isooctyl) phosphate method, it is characterized in that: described triisooctyl phosphate and the mol ratio of sodium hydroxide are 1:(1 ~ 1.1), catalyst levels is 1 ~ 5% of iso-octyl phosphonic acids di-isooctyl amount of substance, the massfraction of sodium hydroxide solution is 15 ~ 45%, temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 2 ~ 5h.
4. a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate according to claim 1 prepares di (isooctyl) phosphate method, it is characterized in that: during described organic phase hcl acidifying, the mol ratio of hydrogenchloride and triisooctyl phosphate is (1 ~ 2): 1.
5. a kind of phase-transfer catalysis hydrolysis triisooctyl phosphate prepares di (isooctyl) phosphate method according to claim 1 or 5, it is characterized in that: during described organic phase hcl acidifying, the massfraction of hydrochloric acid is 10 ~ 36.5%.
6. the concrete grammar steamed except isooctyl alcohol is: vacuum tightness 720 ~ 740mmHg underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859773A (en) * | 2016-04-29 | 2016-08-17 | 三门峡中达化工有限公司 | Technology for preparing di-2-ethylhexyl phosphoric acid through quaternary phosphonium salt phase transfer, catalysis and hydrolysis |
| CN105884821A (en) * | 2016-04-29 | 2016-08-24 | 三门峡中达化工有限公司 | Process for preparing bis phosphate from tri-iso-octyl phosphate by means of phosphonium salt phase-transfer catalytic hydrolysis |
| CN110066291A (en) * | 2018-08-06 | 2019-07-30 | 三门峡中达化工有限公司 | A kind of phase transfer catalysis (PTC) hydrolysis triisooctyl phosphate prepares di (isooctyl) phosphate method |
| CN110294460A (en) * | 2019-06-28 | 2019-10-01 | 平湖石化有限责任公司 | A kind of dicyandiamide solution of the complete acid hydrogen-peroxide working solution of anthraquinone production |
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| CN1111636A (en) * | 1995-03-30 | 1995-11-15 | 江西省奉新化工有限责任公司 | Preparation of phosphate dialkyl ester |
| CN101508644A (en) * | 2009-03-26 | 2009-08-19 | 北京极易化工有限公司 | Novel synthesis method for hindered phenol anti-oxidants |
| CN101696224A (en) * | 2009-11-02 | 2010-04-21 | 甘肃省化工研究院 | Method for synthesizing di(isooctyl) phosphate |
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2015
- 2015-12-11 CN CN201510911559.4A patent/CN105461748A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1111636A (en) * | 1995-03-30 | 1995-11-15 | 江西省奉新化工有限责任公司 | Preparation of phosphate dialkyl ester |
| CN101508644A (en) * | 2009-03-26 | 2009-08-19 | 北京极易化工有限公司 | Novel synthesis method for hindered phenol anti-oxidants |
| CN101696224A (en) * | 2009-11-02 | 2010-04-21 | 甘肃省化工研究院 | Method for synthesizing di(isooctyl) phosphate |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859773A (en) * | 2016-04-29 | 2016-08-17 | 三门峡中达化工有限公司 | Technology for preparing di-2-ethylhexyl phosphoric acid through quaternary phosphonium salt phase transfer, catalysis and hydrolysis |
| CN105884821A (en) * | 2016-04-29 | 2016-08-24 | 三门峡中达化工有限公司 | Process for preparing bis phosphate from tri-iso-octyl phosphate by means of phosphonium salt phase-transfer catalytic hydrolysis |
| CN110066291A (en) * | 2018-08-06 | 2019-07-30 | 三门峡中达化工有限公司 | A kind of phase transfer catalysis (PTC) hydrolysis triisooctyl phosphate prepares di (isooctyl) phosphate method |
| CN110294460A (en) * | 2019-06-28 | 2019-10-01 | 平湖石化有限责任公司 | A kind of dicyandiamide solution of the complete acid hydrogen-peroxide working solution of anthraquinone production |
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