CN102911203A - Preparation method of alkyl phosphate - Google Patents
Preparation method of alkyl phosphate Download PDFInfo
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- CN102911203A CN102911203A CN2012104140596A CN201210414059A CN102911203A CN 102911203 A CN102911203 A CN 102911203A CN 2012104140596 A CN2012104140596 A CN 2012104140596A CN 201210414059 A CN201210414059 A CN 201210414059A CN 102911203 A CN102911203 A CN 102911203A
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Abstract
The invention discloses a preparation method of alkyl phosphate. The method comprises the steps of using an alkyl alcohol as the raw material, adding a phosphorylation agent for phosphorylation in batches, and adding deionized water for hydrolysis to obtain aliphatic alcohol polyoxyethylene phosphate. The method provided by the invention overcomes the drawbacks in the prior art, has the characteristics of mild reaction condition, high selectivity, simple operation, low product cost, light color, high esterification rate and the like, and controls the ratio of monoalkyl phosphate to dialkyl phosphate to a certain range in the obtained reaction products.
Description
Technical field
The present invention relates to a kind of preparation method of alkyl phosphate, belong to the synthesis technical field of organic compound.
Background technology
Alkyl phosphate is a kind of anion surfactant, and it very easily is dissolved in organic solvent, can be re-dubbed the washing composition of a series of special efficients, has good soil removability, particularly crust is had better effect.Simultaneously, it also has wettability, detergency, lyotropy, emulsification and whipability, can reduce surface tension, antistatic, suppress that burn into disperses and anti-dust resedimentation, acid, alkali are had satisfactory stability, and it not only can make plastic plasticizer, mining extraction agent and flotation agent, also can be used widely at aspects such as metal processing, textile process, public cleaning, leather paper pulp, synthetic resins, letex polymerization, makeup, and it still closes one of most important monomer in the fine finish, is described as the tensio-active agent of specific function.
Phosphoric acid ester is that people are familiar with the earliest and study also comparatively deep organo phosphorous compounds.1820, I.L.Lassigne was with phosphoric acid and ethyl esterification, synthetic first organo phosphorous compounds, begun the organo phosphorous compounds chemistry.1854, the Russian at first generated phosphoric acid ester with phosphorus trichloride and alcohol, can be described as the beginning of POC key compound.Be that the phosphorous-containing surfactants of representative has good static resistance emulsifying dispersivity, lubricated, washing and the characteristic such as acidproof and alkaline-resisting with phosphoric acid ester.Along with deepening continuously of scientific research, the enormous industrial of phosphoric acid ester is worth and is constantly found and develop, and becomes an important branch in the phosphorus chemistry.
Phosphoric acid ester researchdevelopment abroad also relatively early, just begin to have carried out in this respect research work in the forties in 20th century, U.S.'s phosphate ester surfactants early 1990s output be about 30,000 t, wherein 1/3 is fatty alcohol phosphate, such as octanol phophoric ester 2-ethylhexanol phosphoric acid ester etc., the 2/3rd, alkyl ether phosphate is such as straight-chain fatty alcohol polyoxyethylene ether phosphate/alkyl phenol ether phosphoric acid ester and 12 aliphatic alcohol polyoxyvinethene phosphates etc.The U.S. has this series products of kind more than 50 now, manufacturer approximately has more than 40, the states such as Japan and West Europe are also very active to the research of phosphorous-containing surfactants, mainly be research phosphate synthesis and composite product thereof, wash agent such as the laundering of textile fabrics material by liquid with concentrated liquid detergent and artificial wash up; Pottery, glass, enamel and metal surface cleaning agent, be used for washing and beauty treatment to the few or non-irritating washing composition compound of skin irritation; To the skin gentleness, has the phosphoric acid ester of outstanding latherability, detergency and emulsifying power; Phosphoric acid ester emulsifying agent for the preparation of stable water dimethylbenzene emulsion; Have good seepage force foaming power and emulsifying power, and the phosphoric acid ester product of high H LB value is arranged.
China's Surfactant Industry is started in mid-term the 1950's, and at first take anion surfactant as main, 20 century 70s begin to develop operation phosphoric acid ester tensio-active agent mid-term.At present, though substantially realize the suitability for industrialized production of various surfactants, but also comparatively fall behind much aspect the Application and Development of phosphoric acid ester tensio-active agent, the kind that performance is comparatively superior is also failed to go into operation and is used, so the present invention is significant to the R and D of phosphoric acid ester product.
Phosphoric acid ester comprises monoesters, dibasic acid esters, three esters and composition thereof.The alkylphosphonic acid carboxylic acid ester structure is:
The structure of alkyl polyoxyethylene ether is:
The actual composition of phosphoric acid ester (comprising that monoesters, dibasic acid esters, three esters, free acid, nonionic thing get ratio) is the important factor that determines product function.Solubleness: monoesters〉dibasic acid esters〉three esters, surface tension: monoesters〉dibasic acid esters〉three esters, soil release characteristics: dibasic acid esters〉monoesters.For the requirement that the ratio that makes monoesters in the target product, dibasic acid esters, three esters and function reach expection, must be by control material molar ratio, phosphorylation agent kind and compound proportion, feed way, temperature of reaction, reaction times and content of water in system.
The preparation method of present alkyl phosphate, the general phosphorylation agent that adopts single component, there is following problem: be phosphorylation agent when carrying out building-up reactions with polyphosphoric acid separately 1., have the reactive low of polyphosphoric acid and Fatty Alcohol(C12-C14 and C12-C18), alcohol ether etc., the shortcomings such as low conversion rate.2. be phosphorylation agent when carrying out building-up reactions with Vanadium Pentoxide in FLAKES separately, have poor selectivity, thermal discharge is large, and raw material easily lumps even carbonization, reacts the shortcoming such as wayward.3. temperature of reaction is too high, and esterification yield is high, but colourity is dark; Reaction temperature is spent low, and colourity is shallow, but speed of reaction is slow, and esterification yield is low, is unfavorable for reacting carrying out.
The content of invention
The object of the present invention is to provide a kind of preparation method of alkyl phosphate, above-mentioned the deficiencies in the prior art have been overcome, have the reaction conditions gentleness, selectivity is high, easy and simple to handle, product cost is low, lighter color, esterification yield high, and the ratio of monoalkyl phosphoric acid esters and bisalkyl phosphate can be regulated and control within the specific limits in the reaction product of gained.
For achieving the above object, technical scheme of the present invention is:
A kind of preparation method of alkyl phosphate comprises the steps: take alkyl alcohol as raw material, adds in batches phosphorylation agent and carries out phosphorylation reaction, adds at last the deionized water reaction that is hydrolyzed and obtains alkyl phosphate.
Described step is specially: 1) phosphorylation reaction: add alkyl alcohol in phosphorylation agent, stir, add Vanadium Pentoxide in FLAKES again, add at last remaining phosphorylation agent again, temperature of reaction is 40～100 ℃, and the reaction times is 0.5 ~ 8 hour; 2) hydrolysis reaction: add deionized water in described step 1), temperature of reaction is 50 ~ 100 ℃, and the reaction times is 0.5～6 hour, and reaction is cooled to chamber Warm after finishing, and gets alkyl phosphate.
Preferable reaction temperature is 50 ~ 90 ℃ in the described step 1) phosphorylation reaction, and the reaction times is 1 ~ 6 hour; Described step 2) preferable reaction temperature is 60 ~ 90 ℃ in the hydrolysis reaction, and the reaction times is 1 ~ 4 hour.
The mol ratio of described alkyl alcohol and phosphorylation agent is 30:1 ~ 5.
Described alkyl alcohol adopts a kind of in Fatty Alcohol(C12-C14 and C12-C18), alcohol ether, fatty alcohol-polyoxyethylene ether, alkylphenol, the alkylphenol polyoxyethylene.
Described alkyl alcohol adopts a kind of in dodecyl alcohol, alkylpolyoxyethylene, 2-Ethylhexyl Alcohol, 2-ethylhexyl Soxylat A 25-7, the hexadecyl alcohol.
Described phosphorylation agent adopt Vanadium Pentoxide in FLAKES (Changzhou friendship ties chemical industry company limited), phosphoric acid (
Upper sea blue clean company limited), in the polyphosphoric acid (Changzhou friendship ties chemical industry company limited), phosphorus oxychloride (Xuzhou Yong Li Fine Chemical Co., Ltd), phosphorus trichloride (Xuzhou Yong Li Fine Chemical Co., Ltd) one or more; And having a kind of phosphorylation agent at least is Vanadium Pentoxide in FLAKES, and the mol ratio of described Vanadium Pentoxide in FLAKES and other phosphorylation agents is 20:1 ~ 5.
Stir speed (S.S.) in the described reaction is 100 ~ 200rpm.
The invention has the beneficial effects as follows: the preparation method of a kind of alkyl phosphate that the application of the invention obtains, compared with prior art, have following outstanding advantages and positively effect: 1. adopt compound phosphoric acid reagent, can allocate according to the relative merits of various phosphorylation agents, so that the exothermic heat of reaction amount is controlled, be not prone to that raw material causes greatly luming because of thermal discharge even the phenomenon of carbonization, colourity is shallow, and esterification yield is high.2. can be according to mol ratio, reaction times and the temperature of reaction of each phosphorylation agent in the mol ratio of allotment raw material and compound phosphoric acid reagent, the compound phosphoric acid reagent, reach in the product monoesters and dibasic acid esters ratio controlled, production is significant to reality.3. technique is simple, and is workable, not high to equipment requirements, and mild condition is fit to suitability for industrialized production.
Embodiment
Embodiment 1
The preparation method of a kind of alkyl phosphate of the present embodiment comprises the steps: 1) phosphorylation reaction: the polyphosphoric acid of 3.5mol is added in the there-necked flask, and temperature is controlled at 80 ℃; Stirring velocity is transferred to 100 ~ 110RPM, with peristaltic pump 30mol dodecyl alcohol is added drop-wise in the there-necked flask, temperature is controlled at 80 ℃; , the Vanadium Pentoxide in FLAKES of adding 0.5mol, temperature is controlled at 80 ℃; Add the polyphosphoric acid of 3.5mol, reacted 6 hours;
2) hydrolysis reaction: 2% of the adding gross weight deionized water in described step 1), temperature of reaction is 70 ℃, stirs hydrolysis 2 hours, reaction is cooled to room temperature after finishing, and gets 1-isobutyl-3,5-dimethylhexylphosphoric acid.
The 1-isobutyl-3,5-dimethylhexylphosphoric acid content that makes by the present embodiment is 90%, and two 1-isobutyl-3,5-dimethylhexylphosphoric acid content are 10%, and esterification yield is 86%.
The preparation method of a kind of alkyl phosphate that obtains by the present embodiment, compared with prior art, have following outstanding advantages and positively effect: 1. adopt compound phosphoric acid reagent, can allocate according to the relative merits of various phosphorylation agents, so that the exothermic heat of reaction amount is controlled, be not prone to that raw material causes greatly luming because of thermal discharge even the phenomenon of carbonization, colourity is shallow, and esterification yield is high.2. can be according to mol ratio, reaction times and the temperature of reaction of each phosphorylation agent in the mol ratio of allotment raw material and compound phosphoric acid reagent, the compound phosphoric acid reagent, reach in the product monoesters and dibasic acid esters ratio controlled, production is significant to reality.3. technique is simple, and is workable, not high to equipment requirements, and mild condition is fit to suitability for industrialized production.
Embodiment 2
The preparation method of a kind of alkyl phosphate of the present embodiment comprises the steps: 1) phosphorylation reaction: the 1.5mol phosphoric acid of inciting somebody to action adds in the there-necked flask, and temperature is controlled at 90 ℃; Stirring velocity is transferred to 140 ~ 150RPM, with peristaltic pump the 30mol alkylpolyoxyethylene is added drop-wise in the there-necked flask, 90 ℃ of control temperature, the Vanadium Pentoxide in FLAKES that adds 14.5mol, the control temperature adds 1mol phosphoric acid again to 90 ℃ of temperature of reaction, reacts 5 hours;
2) hydrolysis reaction: 2% of the adding gross weight deionized water in described step 1), temperature of reaction is 80 ℃, stirs hydrolysis 1 hour, reaction is cooled to room temperature after finishing, and gets the alkylpolyoxyethylene phosphoric acid ester.
The alkylpolyoxyethylene phosphate ester content that makes by the present embodiment is 85%, and two alkylpolyoxyethylene phosphate ester contents are 15%, and esterification yield is 89%.
The preparation method of a kind of alkyl phosphate that obtains by the present embodiment, compared with prior art, have following outstanding advantages and positively effect: 1. adopt compound phosphoric acid reagent, can allocate according to the relative merits of various phosphorylation agents, so that the exothermic heat of reaction amount is controlled, be not prone to that raw material causes greatly luming because of thermal discharge even the phenomenon of carbonization, colourity is shallow, and esterification yield is high.2. can be according to mol ratio, reaction times and the temperature of reaction of each phosphorylation agent in the mol ratio of allotment raw material and compound phosphoric acid reagent, the compound phosphoric acid reagent, reach in the product monoesters and dibasic acid esters ratio controlled, production is significant to reality.3. technique is simple, and is workable, not high to equipment requirements, and mild condition is fit to suitability for industrialized production.
Embodiment 3
The preparation method of a kind of alkyl phosphate of the present embodiment comprises the steps: 1) phosphorylation reaction: the 0.5mol phosphorus trichloride is added in the there-necked flask, and temperature is controlled at 70 ℃; Stirring velocity is transferred to 190 ~ 200RPM, with peristaltic pump the 30mol 2-Ethylhexyl Alcohol is added drop-wise in the there-necked flask, temperature is controlled at 70 ℃, adds the Vanadium Pentoxide in FLAKES of 13.5mol, and temperature is controlled at 70 ℃; Add the 0.8mol phosphorus trichloride, reacted 2 hours;
2) hydrolysis reaction: 2% of the adding gross weight deionized water in described step 1), temperature of reaction is 90 ℃, stirs hydrolysis 2 hours, reaction is cooled to room temperature after finishing, and gets ethylhexyl dihydrogen phosphate.
The ethylhexyl dihydrogen phosphate content that makes by the present embodiment is 70%, and two ethylhexyl dihydrogen phosphate content are 30%, and esterification yield is 84%.
The preparation method of a kind of alkyl phosphate that obtains by the present embodiment, compared with prior art, have following outstanding advantages and positively effect: 1. adopt compound phosphoric acid reagent, can allocate according to the relative merits of various phosphorylation agents, so that the exothermic heat of reaction amount is controlled, be not prone to that raw material causes greatly luming because of thermal discharge even the phenomenon of carbonization, colourity is shallow, and esterification yield is high.2. can be according to mol ratio, reaction times and the temperature of reaction of each phosphorylation agent in the mol ratio of allotment raw material and compound phosphoric acid reagent, the compound phosphoric acid reagent, reach in the product monoesters and dibasic acid esters ratio controlled, production is significant to reality.3. technique is simple, and is workable, not high to equipment requirements, and mild condition is fit to suitability for industrialized production.
Embodiment 4
The preparation method of a kind of alkyl phosphate of the present embodiment comprises the steps: 1) phosphorylation reaction: the 0.4mol phosphorus oxychloride is added in the there-necked flask, and temperature is controlled at 60 ℃; Stirring velocity is transferred to 170 ~ 180RPM, with peristaltic pump 30mol 2-ethylhexyl Soxylat A 25-7 is added drop-wise in the there-necked flask, temperature is controlled at 60 ℃; Add the Vanadium Pentoxide in FLAKES of 14.7mol, temperature is controlled at 60 ℃; Add the 0.4mol phosphorus oxychloride, reacted 3 hours;
2) hydrolysis reaction: 2% of the adding gross weight deionized water in described step 1), temperature of reaction is 50 ℃, stirs hydrolysis 1.5 hours, reaction is cooled to room temperature after finishing, and gets 2-ethylhexyl polyoxyethylene ether phosphate.
The 2-ethylhexyl polyoxyethylene ether phosphate content that makes by the present embodiment is 50%, and two 2-ethylhexyl polyoxyethylene ether phosphate content are 50%, and esterification yield is 82%.
The preparation method of a kind of alkyl phosphate that obtains by the present embodiment, compared with prior art, have following outstanding advantages and positively effect: 1. adopt compound phosphoric acid reagent, can allocate according to the relative merits of various phosphorylation agents, so that the exothermic heat of reaction amount is controlled, be not prone to that raw material causes greatly luming because of thermal discharge even the phenomenon of carbonization, colourity is shallow, and esterification yield is high.2. can be according to mol ratio, reaction times and the temperature of reaction of each phosphorylation agent in the mol ratio of allotment raw material and compound phosphoric acid reagent, the compound phosphoric acid reagent, reach in the product monoesters and dibasic acid esters ratio controlled, production is significant to reality.3. technique is simple, and is workable, not high to equipment requirements, and mild condition is fit to suitability for industrialized production.
Embodiment 5
The preparation method of a kind of alkyl phosphate of the present embodiment comprises the steps: 1) phosphorylation reaction: the 0.5mol polyphosphoric acid is added in the there-necked flask, and temperature is controlled at 55 ℃; Stirring velocity is transferred to 120 ~ 130RPM, with peristaltic pump 30mol hexadecyl alcohol is added drop-wise in the there-necked flask, temperature is controlled at 55 ℃, adds the 10.5mol Vanadium Pentoxide in FLAKES, and temperature is controlled at 55 ℃, adds the 0.5mol phosphorus trichloride, reacts 1 hour;
2) hydrolysis reaction: 2% of the adding gross weight deionized water in described step 1), temperature of reaction is 65 ℃, stirs hydrolysis 3 hours, reaction is cooled to room temperature after finishing, and gets hexadecanyl phosphate.
The hexadecanyl phosphate content that makes by the present embodiment is 60%, and double hexadecyl acid ester content is 40%, and esterification yield is 85%.
The preparation method of a kind of alkyl phosphate that obtains by the present embodiment, compared with prior art, have following outstanding advantages and positively effect: 1. adopt compound phosphoric acid reagent, can allocate according to the relative merits of various phosphorylation agents, so that the exothermic heat of reaction amount is controlled, be not prone to that raw material causes greatly luming because of thermal discharge even the phenomenon of carbonization, colourity is shallow, and esterification yield is high.2. can be according to mol ratio, reaction times and the temperature of reaction of each phosphorylation agent in the mol ratio of allotment raw material and compound phosphoric acid reagent, the compound phosphoric acid reagent, reach in the product monoesters and dibasic acid esters ratio controlled, production is significant to reality.3. technique is simple, and is workable, not high to equipment requirements, and mild condition is fit to suitability for industrialized production.
Reaction equation take Fatty Alcohol(C12-C14 and C12-C18) as raw material as:
Result and the experimental data of the phosphorylation reaction that obtains by embodiment 1 ~ 5 see Table 1, the mol ratio of raw material and phosphorylation agent is larger to the scale effect of monoesters in the reaction product and dibasic acid esters as shown in Table 1, ratio increase along with phosphorylation agent, the ratio of dibasic acid esters increases in the product, increase temperature of reaction and can increase esterification yield, hydrolysis temperature and hydrolysis time increase, and the percentage composition of monoesters increases.
Ratio and the experimental result of embodiment 1 ~ 5 compound phosphoric acid reagent see Table 2, as shown in Table 2 by adjusting the kind of compound phosphoric acid reagent and the mol ratio between the various phosphorylation agent, can be so that the ratio of monoesters and dibasic acid esters can be regulated and control in the reaction product, can be according to practical situations, select suitable preparation condition, to reach the application purpose of expection.
Table 1
Table 2
Claims (8)
1. the preparation method of an alkyl phosphate is characterized in that comprising the steps: take alkyl alcohol as raw material, adds in batches phosphorylation agent and carries out phosphorylation reaction, adds at last the deionized water reaction that is hydrolyzed and obtains alkyl phosphate.
2. the preparation method of a kind of alkyl phosphate according to claim 1, it is characterized in that described step is specially: 1) phosphorylation reaction: stir in phosphorylation agent, add alkyl alcohol, add again Vanadium Pentoxide in FLAKES, add again at last remaining phosphorylation agent, temperature of reaction is 40～100 ℃, and the reaction times is 0.5 ~ 8 hour; 2) hydrolysis reaction: add deionized water in described step 1), temperature of reaction is 50 ~ 100 ℃, and the reaction times is 0.5～6 hour, and reaction is cooled to room temperature after finishing, and gets alkyl phosphate.
3. the preparation method of a kind of alkyl phosphate according to claim 2 is characterized in that temperature of reaction is 50 ~ 90 ℃ in the described step 1) phosphorylation reaction, and the reaction times is 1 ~ 6 hour; Described step 2) temperature of reaction is 60 ~ 90 ℃ in the hydrolysis reaction, and the reaction times is 1 ~ 4 hour.
4. according to claim 1 and 2 or the preparation method of 3 described a kind of alkyl phosphates, the mol ratio that it is characterized in that described alkyl alcohol and phosphorylation agent is 30:1 ~ 5.
5. according to claim 1 and 2 or the preparation method of 4 described a kind of alkyl phosphates, it is characterized in that described alkyl alcohol adopts a kind of in Fatty Alcohol(C12-C14 and C12-C18), alcohol ether, fatty alcohol-polyoxyethylene ether, alkylphenol, the alkylphenol polyoxyethylene.
6. the preparation method of a kind of alkyl phosphate according to claim 5 is characterized in that described alkyl alcohol adopts a kind of in dodecyl alcohol, alkylpolyoxyethylene, 2-Ethylhexyl Alcohol, 2-ethylhexyl Soxylat A 25-7, the hexadecyl alcohol.
7. the preparation method of a kind of alkyl phosphate according to claim 1 and 2 is characterized in that described phosphorylation agent adopts one or more in Vanadium Pentoxide in FLAKES, phosphoric acid, polyphosphoric acid, phosphorus oxychloride, the phosphorus trichloride; And having a kind of phosphorylation agent at least is Vanadium Pentoxide in FLAKES, and the mol ratio of described Vanadium Pentoxide in FLAKES and other phosphorylation agents is 20:1 ~ 5.
8. the preparation method of a kind of alkyl phosphate according to claim 1 and 2 is characterized in that the stir speed (S.S.) in the described reaction is 100 ~ 200rpm.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104972581A (en) * | 2015-05-25 | 2015-10-14 | 江苏全真光学眼镜有限公司 | Phosphate ester compound for optical material internal release agent and preparation method of phosphate ester compound |
| CN106632739A (en) * | 2016-12-10 | 2017-05-10 | 李鑫 | Phosphate emulsifier and preparation method thereof |
| CN107337689A (en) * | 2017-07-13 | 2017-11-10 | 中国日用化学工业研究院 | A kind of synthetic method of alkyl phosphate monoester |
| CN107446124A (en) * | 2017-07-26 | 2017-12-08 | 浙江皇马科技股份有限公司 | The preparation method of fatty alcohol phosphate polyethenoxy ether |
| US10301334B1 (en) | 2018-02-14 | 2019-05-28 | Far Eastern New Century Corporation | Method for preparing stabilizer containing phosphate-ester |
| CN110662733A (en) * | 2016-12-21 | 2020-01-07 | 埃维科生物技术有限公司 | Method of producing a composite material |
| CN111574555A (en) * | 2020-05-15 | 2020-08-25 | 江苏九洲环保技术有限公司 | Method for synthesizing fatty alcohol-polyoxyethylene ether phosphating product |
| CN112266810A (en) * | 2020-11-19 | 2021-01-26 | 上海应用技术大学 | Temperature-resistant ionic liquid lubricant and preparation method thereof |
| CN113512061A (en) * | 2021-08-24 | 2021-10-19 | 沈阳华仑润滑油添加剂有限公司 | Preparation method of phosphate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104972581A (en) * | 2015-05-25 | 2015-10-14 | 江苏全真光学眼镜有限公司 | Phosphate ester compound for optical material internal release agent and preparation method of phosphate ester compound |
| CN106632739A (en) * | 2016-12-10 | 2017-05-10 | 李鑫 | Phosphate emulsifier and preparation method thereof |
| CN110662733A (en) * | 2016-12-21 | 2020-01-07 | 埃维科生物技术有限公司 | Method of producing a composite material |
| CN107337689A (en) * | 2017-07-13 | 2017-11-10 | 中国日用化学工业研究院 | A kind of synthetic method of alkyl phosphate monoester |
| CN107337689B (en) * | 2017-07-13 | 2020-05-05 | 中国日用化学工业研究院 | Synthesis method of alkyl phosphate monoester |
| CN107446124A (en) * | 2017-07-26 | 2017-12-08 | 浙江皇马科技股份有限公司 | The preparation method of fatty alcohol phosphate polyethenoxy ether |
| US10301334B1 (en) | 2018-02-14 | 2019-05-28 | Far Eastern New Century Corporation | Method for preparing stabilizer containing phosphate-ester |
| CN111574555A (en) * | 2020-05-15 | 2020-08-25 | 江苏九洲环保技术有限公司 | Method for synthesizing fatty alcohol-polyoxyethylene ether phosphating product |
| CN112266810A (en) * | 2020-11-19 | 2021-01-26 | 上海应用技术大学 | Temperature-resistant ionic liquid lubricant and preparation method thereof |
| CN113512061A (en) * | 2021-08-24 | 2021-10-19 | 沈阳华仑润滑油添加剂有限公司 | Preparation method of phosphate |
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Effective date of registration: 20150706 Address after: 312363, Shaoxing Town, Zhejiang City, Shangyu province Chapter Industrial Zone Applicant after: Zhejiang Huangma Technology Co., Ltd. Address before: 312363, Shaoxing, Zhejiang province Shangyu City Town Industrial Zone, Zhejiang Cheng Cheng Chemical Co., Ltd. Applicant before: Zhejiang Hecheng Chemical Co., Ltd. |
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Application publication date: 20130206 |