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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- phosphate
- isooctyl
- phase
- sodium hydroxide
- triisooctyl
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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 39
- SNAMIIGIIUQQSP-UHFFFAOYSA-N bis(6-methylheptyl) hydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(=O)OCCCCCC(C)C SNAMIIGIIUQQSP-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 29
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 16
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 16
- 230000003197 catalytic effect Effects 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 77
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 230000035484 reaction time Effects 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000012074 organic phase Substances 0.000 claims description 19
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 13
- 238000003408 phase transfer catalysis Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 5
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 4
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- YLXGYLLBXARBDE-UHFFFAOYSA-N 6-methylheptylphosphonic acid Chemical class CC(C)CCCCCP(O)(O)=O YLXGYLLBXARBDE-UHFFFAOYSA-N 0.000 claims description 3
- HRFSRGWDYVZSSH-UHFFFAOYSA-M [I-].[NH4+].C(CCCCCCCCCCCCC)[N+](C)(C)C.[I-] Chemical compound [I-].[NH4+].C(CCCCCCCCCCCCC)[N+](C)(C)C.[I-] HRFSRGWDYVZSSH-UHFFFAOYSA-M 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000004904 shortening Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 18
- 239000000243 solution Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 238000005265 energy consumption Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 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)
- Catalysts (AREA)
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)
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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 |
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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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