CN104211727A - Preparation method of tributyl phosphate - Google Patents
Preparation method of tributyl phosphate Download PDFInfo
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- CN104211727A CN104211727A CN201410373134.8A CN201410373134A CN104211727A CN 104211727 A CN104211727 A CN 104211727A CN 201410373134 A CN201410373134 A CN 201410373134A CN 104211727 A CN104211727 A CN 104211727A
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- Prior art keywords
- tributyl phosphate
- preparation
- reaction
- butanols
- phosphorus oxychloride
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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 11
- 239000012298 atmosphere Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 229910052728 basic metal Inorganic materials 0.000 claims description 5
- 150000003818 basic metals Chemical class 0.000 claims description 5
- 238000005516 engineering process Methods 0.000 claims description 5
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 18
- 239000002994 raw material Substances 0.000 abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 5
- 150000001340 alkali metals Chemical class 0.000 abstract description 4
- 238000005886 esterification reaction Methods 0.000 abstract description 4
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 2
- 238000007796 conventional method Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- TWFHAEGZFQHISA-UHFFFAOYSA-N chlorobenzene;sodium Chemical compound [Na].ClC1=CC=CC=C1 TWFHAEGZFQHISA-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A preparation method of tributyl phosphate. In the method, the tributyl phosphate is synthesized from a butyl alcohol solution containing sodium butylate and phosphrous oxychloride in a manner of direct esterification. The method includes following steps: enabling an alkali metal or a hydroxide of the alkali metal to react with butanol to prepare an alcoholate with the content of water being less than 0.1%; adding the phosphrous oxychloride dropwisely to the alcoholate under a condition of a reaction temperature at 20-100 DEG C; performing a reaction after the dropwisely addition being finished; and performing filtration and distillation to obtain the object product tributyl phosphate. Compared with a conventional method, the preparation method is high in yield of the tributyl phosphate and is low in consumption of raw materials.
Description
Technical field
The invention belongs to organic chemical industry field, especially relate to a kind of preparation method of tributyl phosphate.
Background technology
The present invention relates to the production of tributyl phosphate, traditional method is the hydrogen chloride gas generated by removing reaction process by alcohol and phosphorus oxychloride direct reaction, thus promotes the carrying out of reaction.Generally there is following problem in such reaction:
1) in reaction, alcohol can overflow along with HCl gas under vacuum, is finally dissolved in acid solution and causes raw material consumption higher.
2) during post-esterification treatment, washing and neutralization procedure have butanols and are dissolved in the water and are difficult to reclaim, thus cause raw material consumption higher.
3) product has a large amount of moisture content by washing, alkali cleaning, salinity exists, and affects quality product, wants to obtain high-quality product, must carry out rectifying, substantially increase the difficulty of technique thus to product;
4) be no matter the recovery of starting material alcohol, or the rectifying of product is in order to strictly control moisture content, generally all can adopt the method for first sedimentation rectifying again, general settling time 6-10 days, extends process cycle so again.
In addition, the water removing generation with 12mol butanols and about 3mol 50% liquid caustic soda by adding water entrainer toluene or benzene is disclosed in patent of invention US3020303A, then phosphorus oxychloride is added dropwise to this system and generates tributyl phosphate and sodium-chlor, benzene, the mixture of butanols, this system washes removing sodium-chlor with water, organic phase removes the butanols in system through underpressure distillation, benzene, this technique Problems existing is: it is can carrying raw material propyl carbinol that (1) this system to wash with water in process at Fen Shui, the sodium chloride solution simultaneously generated in water washing process also result in very large burden to water treatment.(2) water liquid benzene of system introducing is toxic, and a large amount of life-time service can work the mischief to human body.(3) water liquid benzene introduced utilizes later stage raw materials recovery and also causes certain difficulty.
Summary of the invention
The object of the invention is to solve existing tributyl phosphate synthesis technique yield low, the problem that subsequent disposal wastes time and energy, and propose one to utilize alcohol and basic metal (or and alkali metal hydroxide) to react to be formed after alkali metal alcoholate again with the method for phosphorus oxychloride reaction.
In order to realize described goal of the invention, the present invention adopts following technical scheme: a kind of preparation method of tributyl phosphate, its preparation process is: first react under basic metal or alkali metal hydroxide and butanols room temperature in closed reactor, the alcoholate of obtained water content less than 0.1%, under temperature of reaction 20 DEG C of-100 DEG C of conditions, in above-mentioned alcoholate, drip phosphorus oxychloride, dropwise reaction, then filter, distill and obtain target product tributyl phosphate.
Reaction of the present invention is carried out in non-oxidizing atmosphere.
Non-oxidizing atmosphere of the present invention is nitrogen atmosphere, at room temperature first leads to nitrogen 30min displaced air.
The temperature of reaction of dropping phosphorus oxychloride of the present invention is preferably 30 DEG C ~ 60 DEG C, the ester namely containing fatty alcohol.
It is of the present invention that to dropwise the reaction times be 15-60 minute.
The mol ratio of phosphorus oxychloride of the present invention and sodium hydroxide is 1:(3-5), the mol ratio of alcohol and phosphorus oxychloride is (6-10): 1.
The reactant that basic metal of the present invention or alkali metal hydroxide and butanols react, backflow in reflux water-dividing device and remove moisture, the alcoholate of obtained water content less than 0.1%.
Preparation method of the present invention also comprises aftertreatment technology, and described aftertreatment technology is after completion of the reaction, first crosses the sodium-chlor filtering generation, then by the underpressure distillation of filtrate thing, collects institute and want cut.Collect front-end volatiles butanols can directly recycle.By the raw phosphoric acid tri-n-butyl pure water containing a small amount of salinity once, a standing point water organic phase dewaters and obtains the product of purity >99%.
Owing to have employed technique scheme, the present invention has following beneficial effect: butanols after at room temperature first logical nitrogen 30min displaced air terminates and sodium Metal 99.5 react, obtain the butanol solution of sodium butylate; Or the mixed solution of butanols and alkali metal hydroxide is under the reflux temperature of butanols, taken out of the moisture of generation by the azeotropic nature of butanols and water, process remains atmosphere of inert gases, is not more than 0.1% eventually through the butanol solution moisture detecting the sodium butylate generated, and reaction terminates.Afterwards phosphorus oxychloride is added drop-wise to the mixed system that this system generates sodium-chlor, tributyl phosphate, butanols, after mixed system filtering separation, the underpressure distillation of filtrate organic phase obtains the thick ester of tributyl phosphate respectively and reclaims butanols, is a key character of the present invention.At room temperature, in a closed reactor, process remains atmosphere of inert gases to the mixed solution of butanols and alkali metal hydroxide, and an alkali metal salt filtering separation formed in the esterification reaction mixture that reaction terminates is a key character of the present invention.Nonoxidizing atmosphere can effectively prevent due to butanols oxidative condensation and cause phosphoric acid ester color and luster to deepen.And this color must be removed by rectification process.By keeping such non-oxidizing atmosphere, although can not prevent variable color completely, phosphate product variable color reaches and minimizes.The rare gas element of the maintenance non-oxidizing atmosphere that can adopt comprises nitrogen, the rare gas elementes such as argon gas.
Being separated by filtering the mixture that esterification terminates rear formation, can effectively avoiding excessive butanols to be caused the high of raw material consumption by taking out of along with moisture.The characteristic of propyl carbinol and water azeotropic is utilized to take the moisture content of generation out of and promote that metal-alcoholatesization is reacted and accelerate in reaction process.
The reaction result of the usage quantity of alkali metal hydroxide and the alkali metal alcoholate solution of above-mentioned restriction shows, wherein all alcoholate are all in the solution molten, and this is conducive to the subsequent reactions with phosphorus oxychloride.Oxyhydroxide as alkali metal hydroxide, sodium, potassium can use, but for economic reasons, preferred sodium hydroxide.
Adopt the amount of alcohol at least to should be phosphorus oxychloride 6 times amount, and alcohol optimum dose is 6 10 equivalents.Use stoichiometric butanols, namely use 3
equivbutanols, obtain product yield be usually no more than 60%.Phosphorus oxychloride 6 is greater than when employing adds
equivbutanols time, institute the product yield that obtains up to 98%.
The alkali metal hydroxide added in process makes reaction mixture refluxed, dewaters in non-oxidizing atmosphere.Temperature range 90 DEG C-140 DEG C.Reflux water-dividing, until the water content of reaction mixture is no more than the water of about 0.1%, contained by this step eliminates in system as far as possible or that reaction generates moisture, is less than till 0.1% by detection system water content.Water substantially all in removing reaction mixture, plays an important role to raising product yield.
In above-mentioned reaction mixture, add phosphorus oxychloride, and keep reaction mixture in non-oxidizing atmosphere, continue to pass into rare gas element.Alcoholate and phosphorus oxychloride reaction rapid, this exothermic heat of reaction, what should control phosphorus oxychloride adds speed to maintain the reaction range of reaction mixture at 30 DEG C-60 DEG C, controls temperature of reaction extremely important, because higher temperature can cause reactant to decompose, effective productive rate of phosphoric acid ester reduces.
From reaction mixture, separation of phosphorus acid esters is that excessive butanols is reclaimed in the further underpressure distillation of the filtrate obtained, and this step butanols almost can quantitative recovery by being filtered by mixed system.The butanols reclaimed can reclaim and react with alkali metal hydroxide.Thick ester is through washing desalination, and drying and dehydrating, decolouring obtains salable product.
Present method compared with traditional method, the advantages such as gained tributyl phosphate yield is high, raw material consumption is low.
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.
Embodiment 1
Agitator is being housed, thermometer, nitrogen inlet, in the 2000mL four-hole boiling flask of reflux exchanger, is adding propyl carbinol 1110g(15mols successively), sodium Metal 99.5 69g(3mols), and by nitrogen by this mixture, butanols and sodium Metal 99.5 are fully reacted.
Cool reacted mixture, slowly phosphorus oxychloride 153g(1 mol is dripped) in this mixture, and control temperature of reaction at 30 DEG C ~ 60 DEG C by drop rate, after phosphorus oxychloride dropwises, reaction mixture is stirred 30 minutes, reaction system filtered afterwards, filtrate goes pressure distillation to obtain the theoretical 888g of 870g() propyl carbinol.
What obtain is rough again with low-boiling-point substances such as the residual propyl carbinols of wet distillation removing, then washes out freshen, and afterwards through super-dry removing moisture content, the yield of gained tributyl phosphate is 95.8%.
Embodiment 2
Agitator is being housed, thermometer, nitrogen inlet, adds propyl carbinol (12mols) successively in the 2000mL four-hole boiling flask of reflux exchanger, the sodium hydroxide (3 mols) of 50%, and by nitrogen by this mixture, be heated to backflow, phlegma is separated into two-layer, and organic layer turns back in system simultaneously, and water layer removing, until the mixture water content in flask is no more than 0.1%.
Cool reacted mixture, phosphorus oxychloride (1 mols) is slowly dripped in this mixture, and control temperature of reaction at 30 DEG C ~ 60 DEG C by drop rate, after phosphorus oxychloride dropwises, reaction mixture is stirred 30 minutes, reaction system filtered afterwards, filtrate goes pressure distillation to obtain the theoretical 888g of 870g() propyl carbinol.
What obtain is rough again with low-boiling-point substances such as the residual propyl carbinols of wet distillation removing, then washes out freshen, and afterwards through super-dry removing moisture content, the yield of gained tributyl phosphate is 97.8%.
Part not in the detailed description of the invention is prior art.
Claims (8)
1. the preparation method of a tributyl phosphate, it is characterized in that: its preparation process is: first react under basic metal or alkali metal hydroxide and butanols room temperature in closed reactor, the alcoholate of obtained water content less than 0.1%, under temperature of reaction 20 DEG C of-100 DEG C of conditions, in above-mentioned alcoholate, drip phosphorus oxychloride, dropwise reaction, then filter, distill and obtain target product tributyl phosphate.
2. the preparation method of tributyl phosphate as claimed in claim 1, is characterized in that: described reaction is carried out in non-oxidizing atmosphere.
3. the preparation method of tributyl phosphate as claimed in claim 2, is characterized in that: described non-oxidizing atmosphere is nitrogen atmosphere, at room temperature first leads to nitrogen 30min displaced air.
4. the preparation method of tributyl phosphate as claimed in claim 1, is characterized in that: the temperature of reaction of described dropping phosphorus oxychloride is preferably 30 DEG C ~ 60 DEG C.
5. the preparation method of tributyl phosphate as claimed in claim 1, is characterized in that: described in dropwise the reaction times be 15-60 minute.
6. the preparation method of tributyl phosphate as claimed in claim 1, is characterized in that: the mol ratio of described phosphorus oxychloride and sodium hydroxide is 1:(3-5), the mol ratio of butanols and phosphorus oxychloride is (6-10): 1.
7. the preparation method of tributyl phosphate as claimed in claim 1, is characterized in that: the reactant that described basic metal or alkali metal hydroxide reacts with butanols, refluxes and removes moisture, obtain the alcoholate of water content less than 0.1% in reflux water-dividing device.
8. the preparation method of tributyl phosphate as claimed in claim 1, it is characterized in that: described preparation method also comprises aftertreatment technology, described aftertreatment technology is after completion of the reaction, first crosses the sodium-chlor filtering generation, again by reaction mixture underpressure distillation, collect institute and want cut.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410373134.8A CN104211727A (en) | 2014-08-01 | 2014-08-01 | Preparation method of tributyl phosphate |
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| CN201410373134.8A CN104211727A (en) | 2014-08-01 | 2014-08-01 | Preparation method of tributyl phosphate |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859770A (en) * | 2016-05-09 | 2016-08-17 | 云南云天化以化磷业研究技术有限公司 | Method of synthesizing alkyl phosphate |
| CN105884822A (en) * | 2016-04-29 | 2016-08-24 | 三门峡中达化工有限公司 | Technology for preparing tributyl phosphate by means of synthesizing alkali alcoholate by aid of cryogenic process |
| CN107522736A (en) * | 2017-08-24 | 2017-12-29 | 张家港市三联化工科技有限公司 | A kind of preparation method of tributyl phosphate |
| CN107793446A (en) * | 2016-08-31 | 2018-03-13 | 天津市科密欧化学试剂有限公司 | A kind of purification process of SILVER REAGENT tributyl phosphate |
| CN107987103A (en) * | 2017-12-14 | 2018-05-04 | 朱恒军 | The preparation method of trimethyl phosphate |
| CN110452263A (en) * | 2019-08-23 | 2019-11-15 | 三门峡中达化工有限公司 | A kind of method that pyridine catalyzes and synthesizes TRI N BUTYL PHOSPHATE |
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| US3020303A (en) * | 1960-03-25 | 1962-02-06 | Fmc Corp | Production of aliphatic phosphate esters |
| US3415908A (en) * | 1964-05-07 | 1968-12-10 | Vnii Fitopatologii | Method of preparing trialkyl phosphates |
| CN85104673A (en) * | 1985-06-14 | 1987-01-21 | 南开大学 | The production process of tributyl phosphate |
| BR9000781A (en) * | 1990-02-20 | 1991-10-15 | Pxq Quimica E Tecnologia Ltda | PERFECT PROCESS OF PREPARATION OF PHOSPHORIC TRIESTERES |
| CN101885737A (en) * | 2010-07-09 | 2010-11-17 | 山东师范大学 | A kind of sodium alkoxide method preparation technology of trioctyl phosphate |
| 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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2014
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3020303A (en) * | 1960-03-25 | 1962-02-06 | Fmc Corp | Production of aliphatic phosphate esters |
| US3415908A (en) * | 1964-05-07 | 1968-12-10 | Vnii Fitopatologii | Method of preparing trialkyl phosphates |
| CN85104673A (en) * | 1985-06-14 | 1987-01-21 | 南开大学 | The production process of tributyl phosphate |
| BR9000781A (en) * | 1990-02-20 | 1991-10-15 | Pxq Quimica E Tecnologia Ltda | PERFECT PROCESS OF PREPARATION OF PHOSPHORIC TRIESTERES |
| CN101885737A (en) * | 2010-07-09 | 2010-11-17 | 山东师范大学 | A kind of sodium alkoxide method preparation technology of trioctyl phosphate |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105884822A (en) * | 2016-04-29 | 2016-08-24 | 三门峡中达化工有限公司 | Technology for preparing tributyl phosphate by means of synthesizing alkali alcoholate by aid of cryogenic process |
| CN105859770A (en) * | 2016-05-09 | 2016-08-17 | 云南云天化以化磷业研究技术有限公司 | Method of synthesizing alkyl phosphate |
| CN107793446A (en) * | 2016-08-31 | 2018-03-13 | 天津市科密欧化学试剂有限公司 | A kind of purification process of SILVER REAGENT tributyl phosphate |
| CN107522736A (en) * | 2017-08-24 | 2017-12-29 | 张家港市三联化工科技有限公司 | A kind of preparation method of tributyl phosphate |
| CN107987103A (en) * | 2017-12-14 | 2018-05-04 | 朱恒军 | The preparation method of trimethyl phosphate |
| CN110452263A (en) * | 2019-08-23 | 2019-11-15 | 三门峡中达化工有限公司 | A kind of method that pyridine catalyzes and synthesizes TRI N BUTYL PHOSPHATE |
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Application publication date: 20141217 |