CN108129511B - Method for preparing trialkyl phosphate - Google Patents
Method for preparing trialkyl phosphate Download PDFInfo
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- CN108129511B CN108129511B CN201810144587.1A CN201810144587A CN108129511B CN 108129511 B CN108129511 B CN 108129511B CN 201810144587 A CN201810144587 A CN 201810144587A CN 108129511 B CN108129511 B CN 108129511B
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- trialkyl phosphate
- alcohol
- product
- reduced pressure
- phosphorus
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- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 29
- 239000010452 phosphate Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000047 product Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 238000004821 distillation Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000012043 crude product Substances 0.000 claims abstract description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
- 239000011574 phosphorus Substances 0.000 claims abstract description 10
- 230000005587 bubbling Effects 0.000 claims abstract description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005457 ice water Substances 0.000 claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011261 inert gas Substances 0.000 claims abstract description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 8
- 230000000536 complexating effect Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000002411 adverse Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 235000021317 phosphate Nutrition 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- -1 defoamers Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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 Table
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention provides a preparation method of trialkyl phosphate, belonging to the field of chemical industry, wherein under the protection of inert gas, phosphorus trihalide and alcohol are reacted under the condition of ice-water bath, ion exchange resin is used as a catalyst, after the reaction is finished, the system is cooled to room temperature, redundant alcohol and hydrochloric acid are removed by reduced pressure distillation, alcohol and acid in the system are further removed by a bubbling method, a crude product of trialkyl phosphate is obtained, and then the pure product of trialkyl phosphate is obtained by reduced pressure rectification. The catalyst avoids complexing with trialkyl phosphate, effectively avoids adverse effects caused by the complexing of the traditional catalyst and a product, improves the yield and purity of the product, further removes impurities by using a bubbling mode, effectively removes residual impurities in the reduced pressure distillation process, and further improves the yield and purity of the trialkyl phosphate. The total yield of the product is more than 95.9 percent, and the purity is more than 99.8 percent.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to a method for preparing trialkyl phosphate.
Background
Trialkyl phosphates are used in a wide variety of applications, for example as plasticizers, flame retardants, hardeners in plastics and coatings, as wetting agents, flotation agents, defoamers, emulsifiers, stabilizers, etc.
At present, the preparation method of trialkyl phosphate mainly adopts the reaction of phosphorus oxychloride and alcohol, a catalyst can be properly added in the preparation process to facilitate the reaction, Lewis acid or titanate is generally used as the catalyst in the prior art, and a reduced pressure distillation mode is often adopted to remove the redundant alcohol and the generated acid. This has disadvantages in that the catalyst is easily complexed with the product trialkyl phosphate, resulting in a decrease in product yield and purity, and the reduced pressure distillation method is difficult to remove the generated acid and the excessive alcohol, resulting in a decrease in product yield and purity.
Disclosure of Invention
In order to solve the above problems, the present invention provides a method for preparing trialkyl phosphate with improved yield and purity.
The technical scheme adopted by the invention is as follows:
a method for preparing trialkyl phosphate, comprising the steps of,
(1) esterification reaction: under the protection of inert gas, placing phosphorus trihalide and alcohol in a molar ratio of 1: 3-1: 8 in a reaction vessel under the condition of ice-water bath, stirring for 10-15min, slowly heating to 20-30 ℃, slowly adding ion exchange resin, continuously heating to reflux for 20-30min, wherein the mass of the ion exchange resin is 1-10% of the total mass of the phosphorus trihalide and the alcohol;
(2) acid and alcohol removal: cooling the system to room temperature, removing redundant alcohol and hydrochloric acid by reduced pressure distillation, and further removing the alcohol and the acid in the system by using a bubbling method to obtain a trialkyl phosphate crude product; the reduced pressure is-1 to-0.01 MPa, and the distillation time is 1 to 3 hours;
(3) and (3) rectification: and carrying out vacuum rectification on the obtained trialkyl phosphate crude product to obtain a trialkyl phosphate pure product.
Preferably, in the step (1), the phosphorus trihalide oxide is phosphorus oxychloride or phosphorus tribromide, the ion exchange resin is selected from acidic cation exchange resins, further selected from D113 type and 732 type, and the alcohol is selected from C1-C6 alcohol.
Further preferably, the molar ratio of the phosphorus oxyhalide to the alcohol in the step (1) is preferably 1:3 to 1: 6.
Preferably, the step (2) further comprises the following process: and (3) testing the pH value of the obtained crude trialkyl phosphate, if the pH value is greater than or equal to 6.5, performing the step (3), if the pH value is less than 6.5, putting the trialkyl phosphate into an alkaline solution for alkaline washing to reach the pH value of greater than or equal to 6.5, and then performing the step (3), wherein the alkaline solution is an alkali metal or alkaline earth metal hydroxide solution, a carbonate solution or a bicarbonate solution.
The invention has the following advantages:
(1) the invention uses ion exchange resin as catalyst for the first time, replaces the prior Lewis acid catalyst and titanate catalyst, has mild reaction, effectively shortens the reaction time, saves the energy consumption, reduces the cost, can avoid complexing with trialkyl phosphate, effectively avoids the adverse effect caused by the complexing of the traditional catalyst and the product, and improves the yield and the purity of the product.
(2) In the processes of acid removal and alcohol removal, impurities are further removed in a bubbling mode, so that the impurities remained in the process of reduced pressure distillation are effectively removed, and the yield and the purity of the trialkyl phosphate are further improved.
Detailed Description
First embodiment
Under the protection of nitrogen, under the condition of ice-water bath, respectively and slowly adding 15.3g (0.1 mol) of phosphorus oxychloride and 9.4g (0.3 mol) of methanol into a reaction container, slowly stirring for 10min, then gradually heating to 20 ℃, controlling the temperature for 10min, adding 1.2g of D113 type resin, then slowly heating the system to reflux for 20min, stopping the reaction, keeping the temperature for 10min, slowly cooling the system to room temperature, carrying out reduced pressure distillation, removing excessive alcohol and generated acid in the system, wherein the reduced pressure is-0.1 MPa, the distillation time is 1h, further removing impurities for 1h by adopting a bubbling method, determining the pH value of a trimethyl phosphate crude product to be 6.8, rectifying the product according with the pH condition to obtain 13.5g of the product, wherein the yield is 96.4%, and the purity is more than 99.8% by HPLC determination.
Second embodiment
Under the protection of helium, 15.3g (0.1 mol) of phosphorus oxychloride and 12.8g (0.4 mol) of methanol are respectively slowly added into a reaction vessel under the condition of ice-water bath, slowly stirred for 15min, then gradually heating to 20 ℃, controlling the temperature for 15min, adding 1.4g of D113 type resin, and then slowly heating the system to reflux, lasting for 30min, stopping the reaction, keeping the temperature for 10min, slowly cooling the system to room temperature, carrying out reduced pressure distillation to remove excessive alcohol and generated acid in the system, keeping the reduced pressure at-0.5 MPa for 1.5h, continuously removing impurities by adopting a bubbling method for 1.5h, determining the pH value of a trimethyl phosphate crude product to be 6, putting the crude product into a sodium hydroxide solution with the mass concentration of 5% for alkali washing, determining the pH value to be 7, extracting, collecting an organic phase, rectifying the product to obtain 13.6g of a product, wherein the yield is 97.1%, and the purity is more than 99.8% through HPLC determination.
Third embodiment
Under the protection of nitrogen, respectively and slowly adding 30.7g (0.2 mol) of phosphorus oxychloride and 55.2g (1.2 mol) of ethanol into a reaction container under the condition of ice-water bath, slowly stirring for 15min, then gradually heating to 30 ℃, controlling the temperature for 20min, adding 8g of 732 type resin, then slowly heating the system to reflux for 30min, stopping the reaction, keeping the temperature for 30min, slowly cooling the system to room temperature, carrying out reduced pressure distillation, removing excessive alcohol and generated acid in the system, keeping the reduced pressure at-1 MPa for 3h, further removing impurities for 2h by adopting a bubbling method, measuring the pH value of a triethyl phosphate crude product to be 6.9, conforming to the pH condition, rectifying the product to obtain 35.3g of the product, wherein the yield is 97%, and the purity is more than 99.8% by HPLC (high performance liquid chromatography).
Fourth embodiment
Under the protection of argon, 153g (1 mol) of phosphorus oxychloride and 370g (5 mol) of isobutanol are respectively slowly added into a reaction vessel under the condition of ice-water bath, slowly stirred for 15min, then gradually heating to 25 ℃, controlling the temperature for 20min, adding 10gD113 type resin, and then slowly heating the system to reflux, lasting for 30min, stopping the reaction, keeping the temperature for 30min, slowly cooling the system to room temperature, carrying out reduced pressure distillation to remove redundant alcohol and generated acid in the system, keeping the reduced pressure at-0.8 MPa for 3h, continuously removing impurities for 3h by adopting a bubbling method, measuring the pH value of a triisobutyl phosphate crude product to be 6.1, putting the crude product into a sodium carbonate solution with the mass concentration of 5% for alkali washing, measuring the pH value to be 6.8, extracting, collecting an organic phase, and rectifying the product to obtain 255g of a product, wherein the yield is 95.9%, and the purity is more than 99.8% by HPLC (high performance liquid chromatography).
Finally, it should be noted that: it should be understood that the above examples are only for clearly illustrating the present invention and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.
Claims (5)
1. A method for preparing trialkyl phosphate, which is characterized by comprising the following steps,
(1) esterification reaction: under the protection of inert gas, placing phosphorus trihalide and alcohol in a molar ratio of 1: 3-1: 8 in a reaction vessel under the condition of ice-water bath, stirring for 10-15min, slowly heating to 20-30 ℃, controlling the temperature for 5-20min, slowly adding ion exchange resin, namely D113 type resin and 732 type resin, continuously heating to reflux for 20-30min, wherein the mass of the ion exchange resin is 1-10% of the total mass of the phosphorus trihalide and the alcohol;
(2) acid and alcohol removal: cooling the system to room temperature, removing redundant alcohol and hydrochloric acid by reduced pressure distillation, and further removing the alcohol and the acid in the system by using a bubbling method for 1-3h to obtain a trialkyl phosphate crude product; the reduced pressure is-1 to-0.01 MPa, and the distillation time is 1 to 3 hours;
(3) and (3) rectification: and carrying out vacuum rectification on the obtained trialkyl phosphate crude product to obtain a trialkyl phosphate pure product.
2. The method for preparing trialkyl phosphate according to claim 1, wherein the phosphorus trihaloxide in step (1) is phosphorus oxychloride or phosphorus tribromoxide and the alcohol is selected from C1-C6 alcohols.
3. The method for preparing trialkyl phosphate according to any of claims 1-2, wherein the inert gas in step (1) is nitrogen, helium or argon.
4. The method for preparing a trialkyl phosphate according to any of claims 1-2, wherein the molar ratio of phosphorus trihaloxide to alcohol in step (1) is preferably 1:3 to 1: 6.
5. The method for preparing trialkyl phosphate according to any of claims 1-2, wherein step (2) further comprises the process of: and (3) testing the pH value of the obtained crude trialkyl phosphate, if the pH value is greater than or equal to 6.5, performing the step (3), if the pH value is less than 6.5, putting the trialkyl phosphate into an alkaline solution for alkaline washing to reach the pH value of greater than or equal to 6.5, and then performing the step (3), wherein the alkaline solution is an alkali metal or alkaline earth metal hydroxide solution, a carbonate solution or a bicarbonate solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810144587.1A CN108129511B (en) | 2018-02-12 | 2018-02-12 | Method for preparing trialkyl phosphate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810144587.1A CN108129511B (en) | 2018-02-12 | 2018-02-12 | Method for preparing trialkyl phosphate |
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| CN108129511A CN108129511A (en) | 2018-06-08 |
| CN108129511B true CN108129511B (en) | 2020-06-16 |
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| CN109134529A (en) * | 2018-09-11 | 2019-01-04 | 佛山市元通胶粘实业有限公司 | A kind of synthetic method of bis- (levulinic ketone group) tin of di-n-butyl |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704839A (en) * | 2009-09-23 | 2010-05-12 | 宁永林 | High purity triisobutyl phosphate preparation technology |
| CN102040622A (en) * | 2011-01-25 | 2011-05-04 | 洛阳市中达化工有限公司 | Method for synthesizing tributyl phosphate |
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2018
- 2018-02-12 CN CN201810144587.1A patent/CN108129511B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704839A (en) * | 2009-09-23 | 2010-05-12 | 宁永林 | High purity triisobutyl phosphate preparation technology |
| CN102040622A (en) * | 2011-01-25 | 2011-05-04 | 洛阳市中达化工有限公司 | Method for synthesizing tributyl phosphate |
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