CN105503941A - Catalytic synthesis method of tri-iso-octyl phosphate - Google Patents
Catalytic synthesis method of tri-iso-octyl phosphate Download PDFInfo
- Publication number
- CN105503941A CN105503941A CN201510911565.XA CN201510911565A CN105503941A CN 105503941 A CN105503941 A CN 105503941A CN 201510911565 A CN201510911565 A CN 201510911565A CN 105503941 A CN105503941 A CN 105503941A
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- CN
- China
- Prior art keywords
- reaction
- triisooctyl phosphate
- isooctyl alcohol
- catalytic synthesis
- iso
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- FSLSJTZWDATVTK-UHFFFAOYSA-N tris(6-methylheptyl) phosphate Chemical compound CC(C)CCCCCOP(=O)(OCCCCCC(C)C)OCCCCCC(C)C FSLSJTZWDATVTK-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000007036 catalytic synthesis reaction Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000005516 engineering process Methods 0.000 claims abstract description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 239000011968 lewis acid catalyst Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 235000011147 magnesium chloride Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 238000010025 steaming Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- SNAMIIGIIUQQSP-UHFFFAOYSA-N bis(6-methylheptyl) hydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(=O)OCCCCCC(C)C SNAMIIGIIUQQSP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent 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
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a catalytic synthesis method of tri-iso-octyl phosphate, and relates to a synthesis technology of the tri-iso-octyl phosphate. The method achieves the purposes of reducing the use level of isooctanol and the reaction temperature and time and improving the content and yield of the tri-iso-octyl phosphate by improving the traditional technical process of tri-iso-octyl phosphate synthesis. The method is high in practicability, and by adopting the technical scheme, the method has the following beneficial effects: the use level of the isooctanol is reduced by one second, and is close to a theoretical level; secondly, the reaction temperature and time are reduced, so that the content of by-products is reduced and the production cycle is shortened; thirdly, the content and yield of the tri-iso-octyl phosphate are obviously improved.
Description
[technical field]
The present invention relates to a kind of triisooctyl phosphate synthetic technology, especially relate to a kind of process for catalytic synthesis of triisooctyl phosphate.
[background technology]
Known, triisooctyl phosphate is a kind of important Chemicals, hydrometallurgy can be used for as metal extraction agent, also can be used in the production of hydrogen peroxide as solvent, its most important purposes prepares di (isooctyl) phosphate through hydrolysis, the commodity of di (isooctyl) phosphate are called P204, it is a kind of important phosphorous hydrometallurgical extraction agent, be widely used in non-ferrous metal extraction field, 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, occupy irreplaceable status.
Industrially generally synthesize triisooctyl phosphate with phosphorus oxychloride and isooctyl alcohol direct esterification, but because isooctyl alcohol spatial volume is larger, this reaction must at high temperature be carried out, and the reaction times is longer, isooctyl alcohol is greatly excessive, and after operation like this, the content of triisooctyl phosphate is still lower, and yield is also lower.
[summary of the invention]
In order to overcome the deficiency in background technology, the invention discloses a kind of process for catalytic synthesis of triisooctyl phosphate, the present invention is by improving the technological process of conventional synthesis triisooctyl phosphate, isooctyl alcohol consumption is reduced to reach, reduce temperature of reaction, reduce the reaction times, improve the content of triisooctyl phosphate and the object of yield.
In order to realize described goal of the invention, the present invention adopts following technical scheme:
A process for catalytic synthesis for triisooctyl phosphate, concrete preparation method is as follows:
The first step, add isooctyl alcohol and Lewis acid catalyst in the reactor, regulate temperature lower than 25 DEG C, under whipped state, drip phosphorus oxychloride, the mol ratio of phosphorus oxychloride and isooctyl alcohol is 1:(3 ~ 6), drip process temperature and control all the time below 25 DEG C, dropwise, 30 DEG C of reaction 1 ~ 2h, 60 DEG C of reaction 1 ~ 2h, 90 DEG C of reaction 1 ~ 2h;
Further, aftertreatment technology is: after completion of the reaction, and reaction solution removes isooctyl alcohol obtain target product triisooctyl phosphate through washing, neutralization, steaming.
Described described Lewis acid catalyst is aluminum chloride, magnesium dichloride and titanium tetrachloride.
Described catalyst levels is 1 ~ 10% of phosphorus oxychloride amount of substance.
Described aftertreatment technology is: after catalyzed reaction, treat that temperature is down to less than 30 DEG C, in reaction solution, add a certain amount of water, stir 10min, leave standstill 10min, separatory, with 15 ~ 30% aqueous sodium hydroxide solution neutralizations, washing, separatory, (vacuum tightness is 720 ~ 740mmHg) underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol, obtains triisooctyl phosphate.
Owing to have employed technique scheme, the present invention has following beneficial effect:
The process for catalytic synthesis of a kind of triisooctyl phosphate of the present invention, by improving the technological process of conventional synthesis triisooctyl phosphate, reducing isooctyl alcohol consumption to reach, reducing temperature of reaction, reduce the reaction times, improve the content of triisooctyl 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, isooctyl alcohol consumption reduces 1/2, and close to theoretical amount; The second, temperature of reaction reduces, and the reaction times is shorter, and by-products content is reduced, and the production cycle shortens; 3rd, the content of triisooctyl phosphate and yield raise, and content and yield increase significantly.
[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.
The process for catalytic synthesis of described a kind of triisooctyl phosphate, concrete preparation method is as follows:
The first step, add isooctyl alcohol and Lewis acid catalyst in the reactor, regulate temperature lower than 25 DEG C, under whipped state, drip phosphorus oxychloride, the mol ratio of phosphorus oxychloride and isooctyl alcohol is 1:(3 ~ 6), drip process temperature and control all the time below 25 DEG C, dropwise, 30 DEG C of reaction 1 ~ 2h, 60 DEG C of reaction 1 ~ 2h, 90 DEG C of reaction 1 ~ 2h;
Further, aftertreatment technology is: after completion of the reaction, and reaction solution removes isooctyl alcohol obtain target product triisooctyl phosphate through washing, neutralization, steaming.
Described described Lewis acid catalyst is aluminum chloride, magnesium dichloride and titanium tetrachloride.
Described catalyst levels is 1 ~ 10% of phosphorus oxychloride amount of substance.
Described aftertreatment technology is: after catalyzed reaction, treat that temperature is down to less than 30 DEG C, in reaction solution, add a certain amount of water, stir 10min, leave standstill 10min, separatory, with 15 ~ 30% aqueous sodium hydroxide solution neutralizations, washing, separatory, (vacuum tightness is 720 ~ 740mmHg) underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol, obtains triisooctyl phosphate.
The content of the triisooctyl phosphate prepared by existing preparation method is still lower than 95%, and yield is lower than 90%.
Embodiment 1
273.5g (2.1mol) isooctyl alcohol and 4.0g (0.03mol) aluminum chloride is added successively in the 1000mL four-hole bottle that thermometer is housed, stir, control temperature less than 25 DEG C, slow dropping 92.1g (0.6mol) phosphorus oxychloride, 1h drips, 30 DEG C of reaction 1h, 60 DEG C of reaction 1h, 90 DEG C of reaction 2h, insulation terminates, be cooled to less than 30 DEG C, add 200g water, stir 10min, leave standstill separatory, 30% aqueous sodium hydroxide solution neutralization is added in organic phase, separatory, underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol, it is triisooctyl phosphate in four-hole bottle, quality 251.6g, yield is 95.5%, gas chromatographic purity is 99.0%.The yield of the triisooctyl phosphate described in this patent is all the yields calculated with phosphorus oxychloride.
Embodiment 2
By the method for example 1, catalyzer changes magnesium dichloride into, and its charging capacity is 2.9g (0.03mol), and other conditions are constant, obtains product 251.8g, yield 94.8%, and gas chromatographic purity is 98.2%.
Embodiment 3
By the method for example 1, catalyzer changes titanium tetrachloride into, and its charging capacity is 5.7g (0.03mol), and other conditions are constant, obtains product 250.8g, yield 95.0%, and gas chromatographic purity is 98.8%.
Embodiment 4
By the method for example 1, the charging capacity of isooctyl alcohol changes 234.4g (1.8mol) into, and other conditions are constant, obtain product 250.2g, yield 94.5%, and gas chromatographic purity is 98.5%.
Embodiment 5
By the method for example 2, the charging capacity of isooctyl alcohol changes 234.4g (1.8mol) into, and other conditions are constant, obtain product 248.6g, yield 94.0%, and gas chromatographic purity is 98.6%.
Embodiment 6
By the method for example 3, the charging capacity of isooctyl alcohol changes 234.4g (1.8mol) into, and other conditions are constant, obtain product 247.1g, yield 93.2%, and gas chromatographic purity is 98.4%.
Part not in the detailed description of the invention is prior art.
Claims (4)
1. a process for catalytic synthesis for triisooctyl phosphate, is characterized in that: concrete preparation method is as follows:
The first step, add isooctyl alcohol and Lewis acid catalyst in the reactor, regulate temperature lower than 25 DEG C, under whipped state, drip phosphorus oxychloride, the mol ratio of phosphorus oxychloride and isooctyl alcohol is 1:(3 ~ 6), drip process temperature and control all the time below 25 DEG C, dropwise, 30 DEG C of reaction 1 ~ 2h, 60 DEG C of reaction 1 ~ 2h, 90 DEG C of reaction 1 ~ 2h;
Further, aftertreatment technology is: after completion of the reaction, and reaction solution removes isooctyl alcohol obtain target product triisooctyl phosphate through washing, neutralization, steaming.
2. the process for catalytic synthesis of a kind of triisooctyl phosphate according to claim 1, is characterized in that: described described Lewis acid catalyst is aluminum chloride, magnesium dichloride and titanium tetrachloride.
3. the process for catalytic synthesis of a kind of triisooctyl phosphate according to claim 1, is characterized in that: described catalyst levels is 1 ~ 10% of phosphorus oxychloride amount of substance.
4. the process for catalytic synthesis of a kind of triisooctyl phosphate according to claim 1, it is characterized in that: described aftertreatment technology is: after catalyzed reaction, treat that temperature is down to less than 30 DEG C, in reaction solution, add a certain amount of water, stir 10min, leave standstill 10min, separatory, with 15 ~ 30% aqueous sodium hydroxide solution neutralizations, washing, separatory, (vacuum tightness is 720 ~ 740mmHg) underpressure distillation, collecting 90 ~ 170 DEG C of cuts is isooctyl alcohol, obtains triisooctyl phosphate.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510911565.XA CN105503941A (en) | 2015-12-11 | 2015-12-11 | Catalytic synthesis method of tri-iso-octyl phosphate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510911565.XA CN105503941A (en) | 2015-12-11 | 2015-12-11 | Catalytic synthesis method of tri-iso-octyl phosphate |
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| CN105503941A true CN105503941A (en) | 2016-04-20 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279265A (en) * | 2016-08-24 | 2017-01-04 | 浙江万盛股份有限公司 | A kind of preparation method of flame-retardant plasticizer tricresyl phosphate (2 propyl group 1 heptan) ester |
| CN106380481A (en) * | 2016-08-24 | 2017-02-08 | 浙江万盛股份有限公司 | Preparation method of tri-iso-octyl phosphate |
| CN110655531A (en) * | 2018-06-28 | 2020-01-07 | 张家港市国泰华荣化工新材料有限公司 | Synthetic method of triisooctyl phosphate |
| CN110818736A (en) * | 2019-10-30 | 2020-02-21 | 南京师范大学镇江创新发展研究院 | Method for removing Lewis acid ionic liquid catalyst in phosphate ester flame retardant product |
| CN111889046A (en) * | 2020-07-20 | 2020-11-06 | 南通江山农药化工股份有限公司 | Micro-channel reaction equipment and preparation method of halogen-free organic phosphorus flame retardant |
| CN115974914A (en) * | 2022-12-15 | 2023-04-18 | 广西兴达精细化工有限公司 | Synthetic method of trioctyl phosphate |
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| US5616768A (en) * | 1994-06-23 | 1997-04-01 | Daihachi Chemical Industry Co., Ltd. | Process for purifying phosphoric esters |
| CN103435642A (en) * | 2013-09-02 | 2013-12-11 | 杭州潜阳科技有限公司 | Production method of trioctyl phosphate |
-
2015
- 2015-12-11 CN CN201510911565.XA patent/CN105503941A/en active Pending
Patent Citations (2)
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|---|---|---|---|---|
| US5616768A (en) * | 1994-06-23 | 1997-04-01 | Daihachi Chemical Industry Co., Ltd. | Process for purifying phosphoric esters |
| CN103435642A (en) * | 2013-09-02 | 2013-12-11 | 杭州潜阳科技有限公司 | Production method of trioctyl phosphate |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279265A (en) * | 2016-08-24 | 2017-01-04 | 浙江万盛股份有限公司 | A kind of preparation method of flame-retardant plasticizer tricresyl phosphate (2 propyl group 1 heptan) ester |
| CN106380481A (en) * | 2016-08-24 | 2017-02-08 | 浙江万盛股份有限公司 | Preparation method of tri-iso-octyl phosphate |
| CN106380481B (en) * | 2016-08-24 | 2018-12-28 | 浙江万盛股份有限公司 | A kind of preparation method of triisooctyl phosphate |
| CN110655531A (en) * | 2018-06-28 | 2020-01-07 | 张家港市国泰华荣化工新材料有限公司 | Synthetic method of triisooctyl phosphate |
| CN110818736A (en) * | 2019-10-30 | 2020-02-21 | 南京师范大学镇江创新发展研究院 | Method for removing Lewis acid ionic liquid catalyst in phosphate ester flame retardant product |
| CN111889046A (en) * | 2020-07-20 | 2020-11-06 | 南通江山农药化工股份有限公司 | Micro-channel reaction equipment and preparation method of halogen-free organic phosphorus flame retardant |
| CN115974914A (en) * | 2022-12-15 | 2023-04-18 | 广西兴达精细化工有限公司 | Synthetic method of trioctyl phosphate |
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