CN107337689A - A kind of synthetic method of alkyl phosphate monoester - Google Patents
A kind of synthetic method of alkyl phosphate monoester Download PDFInfo
- Publication number
- CN107337689A CN107337689A CN201710568277.8A CN201710568277A CN107337689A CN 107337689 A CN107337689 A CN 107337689A CN 201710568277 A CN201710568277 A CN 201710568277A CN 107337689 A CN107337689 A CN 107337689A
- Authority
- CN
- China
- Prior art keywords
- alkyl phosphate
- synthetic method
- phosphoric acid
- phosphate monoester
- monoester
- Prior art date
- 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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Links
- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 30
- -1 alkyl phosphate Chemical compound 0.000 title claims abstract description 30
- 239000010452 phosphate Substances 0.000 title claims abstract description 30
- 238000010189 synthetic method Methods 0.000 title claims abstract description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 230000026731 phosphorylation Effects 0.000 claims abstract description 12
- 238000006366 phosphorylation reaction Methods 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 241001272567 Hominoidea Species 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910019213 POCl3 Inorganic materials 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000009736 wetting 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of synthetic method of alkyl phosphate monoester is with phosphoric acid and P2O5Mixture is phosphorylation agent, using fatty alcohol or aliphatic ether as raw material, uniformly after mixing, reacts 1 15h under the conditions of the 0.08MPa of vacuum 0.02,70 120 DEG C of reaction temperature, the 700r/min of speed of agitator 200, obtains product.The present invention has the advantages of monoesters selectivity is high, monoester content is high, environment-friendly.
Description
Technical field
The present invention relates to a kind of synthetic method of alkyl phosphate monoester.
Background technology
In recent years, phosphate ester surfactant is because it has less toxic, non-stimulated and significant biodegradable etc.
Good performance and be widely used.Alkyl phosphate is as one of phosphate ester surfactant, its solubility, thermostabilization
Property, resistance to hard water, acid and alkali-resistance, resistance to inorganic salts, high temperature resistant and the performance such as antistatic are superior to general surfactant, thus widely
Applied to preparation medium, emulsifying agent, antistatic additive, lubricant etc..
Alkyl phosphate is including monoesters, dibasic acid esters and three esters, alkyl phosphate monoester and its salt with having performance temperature compared with other
With, toxicity is low, excitant is small, biological degradability is good the advantages that, while also have wetting, clean, solubilising, emulsification, lubrication etc. it is more
Kind function, thus it is widely used in the fields such as daily use chemicals, weaving, industry cleaning link.But the phosphorus of domestic production at present and sale
Monoester content is not high in acid esters, and the high content alkyl phosphate monoester overwhelming majority needs import, and commercially available prod is monoesters and dibasic acid esters
Mixture.Because the separating difficulty of alkyl phosphate monoester and dibasic acid esters is big, as product purity and monoester content raise, price
Sharply increase, raised in addition with the purity of raw material, its cosmetics prepared and personal few washing product security are also higher.Cause
This carries out the research of mono phosphoric acid ester esters surface active agent new varieties and new technology, and especially exploitation prepares high-purity alkyl phosphoric acid list
Ester and alkyl phosphoric acid dibasic acid esters synthetic technology, to promoting the sound development of China's Surfactant Industry, and meet national economy
The needs of all departments' Surfactant are very important.
Phosphate ester surfactant synthesizes in two stages, and the first stage is phosphate synthesis, second stage saponification.
From the angle analysis of product quality, synthetic technology is crucial.The A of patent CN 103833785 use P2O5Synthesized for phosphorylation agent
Alkyl phosphate, synthetic product are the mixture of single dibasic acid esters, and the content of monoesters is 48-52wt%.Industrially use traditional P2O5Work
Monoester content is 35%-65% in skill synthetic phosphoric acid ester, by improving P2O5It is also left 75% that technique adds water to hydrolyze final monoester content
The right side, due to containing dibasic acid esters, therefore monoesters poor selectivity in sintetics.The A of patent CN 104804038 use POCl3 as phosphorus
Acidizing reagent synthesis of alkyl phosphate, the reactivity is high, and reaction speed is fast, but the low boiling point of raw material POCl3 is easily waved
Hair, the accessory substance HCl meeting etching apparatuses of generation, and HCl easily reacts generation RCl accessory substances with ROH, is unfavorable for the generation of monoesters.
The A of patent CN 103012469 use phosphoric acid as phosphorylation agent, add water entrainer synthesis of alkyl phosphate, and the technique synthesized
Organic solvent toluene, dichloroethanes etc. are added in journey, does not meet the requirement of friendly process.Patent CN 104804038A are described
A kind of preparation method of phosphate, it uses hypergravity rotatable reactor, and structure of reactor is complicated, and cost is high, while also to adopt
With solvent diluent, wherein solvent diluent is mostly poisonous and hazardous organic solvent, is not suitable for industrialized production；The nineties day
For light industry chemistry institute Wangqing County of Jinshi City into waiting using polyphosphoric acids method synthesis dodecylphosphoric acid monoesters, monoester content is high, but by
In use polyphosphoric acid technique, waste water great difficulty is brought containing a large amount of phosphoric acid to post processing.Therefore, green syt height contains
The alkyl phosphate monoester of amount has realistic meaning and economic value.
The content of the invention
To solve problems of the prior art, it is an object of the invention to provide a kind of monoesters selectivity height, monoesters to contain
Amount is high, the synthetic method of environment-friendly alkyl phosphate monoester.
The present invention is with phosphoric acid（Commercially available 85wt%）And P2O5Mixture is phosphorylation agent, with fatty alcohol（Ether）For raw material,
By Depressor response one-step synthesis of alkyl phosphate monoester, monoesters selectivity height, monoester content in the product synthesized by the present invention
Height, added value is high, can be applied in the high-end skin-protection product such as cosmetics, while present invention process is simple, and reaction condition is gentle, instead
Answer speed fast, be a kind of environment-friendly green synthesis method.
To reach above-mentioned purpose, what the present invention was realized in：
With phosphoric acid and P2O5Mixture is phosphorylation agent, using fatty alcohol or aliphatic ether as raw material, uniformly after mixing, in vacuum
1-15h is reacted under the conditions of 0.02-0.08MPa, 70-120 DEG C of reaction temperature, speed of agitator 200-700r/min, obtains product.
The mol ratio of fatty alcohol or aliphatic ether and phosphorylation agent is 1-1.5 in said process:1；
Phosphoric acid and P in said process2O5Mass ratio be 0.5-3:1；Phosphoric acid is commercially available 85wt% phosphoric acid.
The fatty alcohol being related in said process is single carbon chain alcohol and mixed carbon alcohol, and ether is AEO or alkyl
One kind in phenol polyethenoxy ether etc..
This technology has advantages below compared with prior art：
1st, with phosphoric acid and P2O5Mixture is phosphorylation agent, is overcome when using phosphoric acid as phosphorylation agent, and phosphatase reaction is lived
Property, the problem of conversion ratio is not high, improve monoester content in product.
2nd, with phosphoric acid and P2O5Mixture is phosphorylation agent, is overcome using P2O5For phosphorylation agent when, P2O5Reaction
The higher selectivity for causing product to have the shortcomings that dibasic acid esters generation, improving monoesters in product of activity.
3rd, it is only water by the byproduct of reaction, economy is high, is a green synthesis route.
4th, in sintetics alkyl phosphate, monoester content is more than 67wt%, and monoesters can selectively reach 100%.
5th, the reaction condition is gentle, and technique is simple, is adapted to industrialized production.
Embodiment
Embodiment 1：
Weigh phosphoric acid, phosphorus pentoxide, lauryl alcohol be respectively 5.6,11.2,38.4g be well mixed in reactor, setting reaction
110 DEG C of temperature, while suitable speed of agitator, vacuum are controlled, wherein speed of agitator is 450r/min, vacuum 0.05M
Pa, 4h is reacted under the above-described reaction conditions.After completion of the reaction, sampling analysis is stand-by.Wherein dodecylphosphoric acid monoester content is
77wt%, monoesters are selectively 100%.Dodecylphosphoric acid monoester content is 92wt% after isolating and purifying.
Embodiment 2：
Weigh phosphoric acid, phosphorus pentoxide, octadecyl alcolol be respectively 9.4,8.4,54.1g be well mixed in reactor, setting reaction
120 DEG C of temperature, while suitable speed of agitator, vacuum are controlled, wherein speed of agitator is 200r/min, vacuum 0.06M
Pa, 1h is reacted under the above-described reaction conditions, after completion of the reaction, sampling analysis is stand-by.Wherein Inverse suspension content is
67wt%, monoesters are selectively 100%.Inverse suspension content is 88wt% after isolating and purifying.
Embodiment 3：
Weigh phosphoric acid, phosphorus pentoxide, lauryl alcohol be respectively 14.1,4.7,52.6g be well mixed in reactor, setting reaction
100 DEG C of temperature, while suitable speed of agitator, vacuum are controlled, wherein speed of agitator is 400r/min, vacuum 0.05M
Pa, 6h is reacted under the above-described reaction conditions, after completion of the reaction, sampling analysis is stand-by.Wherein dodecylphosphoric acid monoester content is
83.6wt%, monoesters are selectively 100%.Dodecylphosphoric acid monoester content is 94wt% after isolating and purifying.
Embodiment 4：
Weigh phosphoric acid, phosphorus pentoxide, docosanol be respectively 12.2,11,101.9g be well mixed in reactor, setting is anti-
90 DEG C of temperature is answered, while controls suitable speed of agitator, vacuum, wherein speed of agitator is 700r/min, vacuum 0.05M
Pa, 15h is reacted under the above-described reaction conditions, after completion of the reaction, sampling analysis is stand-by.Wherein monoester content is 74 wt%, monoesters
Selectivity is 100%.Alkyl phosphate monoester content is 88wt% after isolating and purifying.
Embodiment 5：
Weigh phosphoric acid, phosphorus pentoxide, 12,14 mixed carbon alcohol（12, tetradecyl alchohol mass ratio is 3:1）Respectively 9.4,8.4,
45.7g is well mixed in reactor, sets 70 DEG C of reaction temperature, while controls suitable speed of agitator, vacuum, wherein stirring
Mix rotating speed is 500r/min, vacuum 0.02MPa, reacts 15h, after completion of the reaction, sampling analysis under the above-described reaction conditions
It is stand-by.Wherein alkyl phosphate monoester content is 72 wt%, and monoesters is selectively 100%.Monoester content is 90 after isolating and purifying
wt%。
Embodiment 6：
Weigh phosphoric acid, phosphorus pentoxide, AEO9Respectively 22.2,8.4,123.2g in reactor be well mixed, setting reaction
120 DEG C of temperature, while suitable speed of agitator, vacuum are controlled, wherein speed of agitator is 400r/min, vacuum 0.08M
Pa, 8h is reacted under the above-described reaction conditions, after completion of the reaction, sampling analysis is stand-by.Wherein AEO9Phosphate monoester content is 74
Wt%, monoesters are selectively 100%.Monoester content is 88wt% after isolating and purifying.
Claims (6)
1. a kind of synthetic method of alkyl phosphate monoester, it is characterised in that comprise the following steps：
With phosphoric acid and P2O5Mixture is phosphorylation agent, using fatty alcohol or aliphatic ether as raw material, uniformly after mixing, in vacuum
1-15h is reacted under the conditions of 0.02-0.08MPa, 70-120 DEG C of reaction temperature, speed of agitator 200-700r/min, obtains product.
2. a kind of synthetic method of alkyl phosphate monoester as claimed in claim 1, it is characterised in that the fatty alcohol or fat
The mol ratio of ether and phosphorylation agent is 1-1.5:1.
3. a kind of synthetic method of alkyl phosphate monoester as claimed in claim 1, it is characterised in that phosphoric acid and P2O5Mass ratio
For 0.5-3:1.
4. a kind of synthetic method of alkyl phosphate monoester as claimed in claim 1, it is characterised in that phosphoric acid is commercially available 85wt%
Phosphoric acid.
5. a kind of synthetic method of alkyl phosphate monoester as claimed in claim 1, it is characterised in that fatty alcohol is single carbon chain alcohol
And mixed carbon alcohol.
6. a kind of synthetic method of alkyl phosphate monoester as claimed in claim 1, it is characterised in that aliphatic ether is poly alkyl alcohol
Oxygen vinethene or APES.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710568277.8A CN107337689B (en) | 2017-07-13 | 2017-07-13 | Synthesis method of alkyl phosphate monoester |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710568277.8A CN107337689B (en) | 2017-07-13 | 2017-07-13 | Synthesis method of alkyl phosphate monoester |
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| Publication Number | Publication Date |
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| CN107337689A true CN107337689A (en) | 2017-11-10 |
| CN107337689B CN107337689B (en) | 2020-05-05 |
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07316170A (en) * | 1994-05-24 | 1995-12-05 | Kao Corp | Production of phosphoric monoester |
| CN1158132A (en) * | 1994-09-20 | 1997-08-27 | 花王株式会社 | Process for the preparation of phosphoric monoester |
| CN1174556A (en) * | 1994-12-09 | 1998-02-25 | 花王株式会社 | Process for prep. of phosophoric monoester |
| CN1389467A (en) * | 2001-05-31 | 2003-01-08 | 花王株式会社 | Method for preparing phosphate |
| JP2003128684A (en) * | 2001-10-25 | 2003-05-08 | Kao Corp | Production method of monophosphate |
| JP2007326819A (en) * | 2006-06-08 | 2007-12-20 | Kao Corp | Method for producing phosphoric monoester |
| CN102911203A (en) * | 2012-10-25 | 2013-02-06 | 浙江合诚化学有限公司 | Preparation method of alkyl phosphate |
| CN103483375A (en) * | 2013-10-09 | 2014-01-01 | 广州潮徽化工科技有限公司 | High-carbon fatty alcohol phosphate ester emulsifier, and preparation method and application thereof |
| CN104130284A (en) * | 2014-07-03 | 2014-11-05 | 江苏理工学院 | Preparation method of fluorine-containing phosphoric acid monoester salt |
-
2017
- 2017-07-13 CN CN201710568277.8A patent/CN107337689B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07316170A (en) * | 1994-05-24 | 1995-12-05 | Kao Corp | Production of phosphoric monoester |
| CN1158132A (en) * | 1994-09-20 | 1997-08-27 | 花王株式会社 | Process for the preparation of phosphoric monoester |
| CN1174556A (en) * | 1994-12-09 | 1998-02-25 | 花王株式会社 | Process for prep. of phosophoric monoester |
| CN1389467A (en) * | 2001-05-31 | 2003-01-08 | 花王株式会社 | Method for preparing phosphate |
| JP2003128684A (en) * | 2001-10-25 | 2003-05-08 | Kao Corp | Production method of monophosphate |
| JP2007326819A (en) * | 2006-06-08 | 2007-12-20 | Kao Corp | Method for producing phosphoric monoester |
| CN102911203A (en) * | 2012-10-25 | 2013-02-06 | 浙江合诚化学有限公司 | Preparation method of alkyl phosphate |
| CN103483375A (en) * | 2013-10-09 | 2014-01-01 | 广州潮徽化工科技有限公司 | High-carbon fatty alcohol phosphate ester emulsifier, and preparation method and application thereof |
| CN104130284A (en) * | 2014-07-03 | 2014-11-05 | 江苏理工学院 | Preparation method of fluorine-containing phosphoric acid monoester salt |
Non-Patent Citations (1)
| Title |
|---|
| 沈磊等: "月桂醇高选择性酯化合成单十二烷基磷酸酯", 《日用化学工业》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| CN107337689B (en) | 2020-05-05 |
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