CN106278961A - A kind of synthetic method of sodium tetradecyl sulfate - Google Patents
A kind of synthetic method of sodium tetradecyl sulfate Download PDFInfo
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- CN106278961A CN106278961A CN201510253142.3A CN201510253142A CN106278961A CN 106278961 A CN106278961 A CN 106278961A CN 201510253142 A CN201510253142 A CN 201510253142A CN 106278961 A CN106278961 A CN 106278961A
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- tetradecyl sulfate
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Abstract
The present invention relates to the field of chemical synthesis, be specifically related to the synthetic method of a kind of sodium tetradecyl sulfate.The synthetic method of sodium tetradecyl sulfate of the present invention uses lipophylic organic solvents to extract sodium tetradecyl sulfate crude product, effectively removes process contaminants, it is to avoid use high boiling halogenating agent, easy and simple to handle, with low cost.The sodium tetradecyl sulfate finished product purity simultaneously obtained is high, and relevant content of material is below 0.1%, quality controllable, is suitable for the commercial production of sodium tetradecyl sulfate.
Description
Technical field
The present invention relates to the field of chemical synthesis, be specifically related to the synthetic method of a kind of sodium tetradecyl sulfate.
Background technology
Sodium tetradecyl sulfate (sodium tetradecyl sulfate) is the surfactant of a kind of anion,
Molecular formula C14H29NaSO4；Molecular weight 316.44.Structural formula is:
Sodium tetradecyl sulfate is used for, as Sclerosing foam, the shallow vein song that hardens by nineteen forty-six Reiner
And telangiectatic treatment, be thus introduced in the treatment of venectasia, from nineteen fifty with
It is widely used.But the research to its preparation technology rarely has report always.Want to obtain ideal,
Meet the preparation technology being applied in terms of medicament research and medicinal application, become inquire into for it numerous always
Scientist and a difficult problem for scholar's headache, long-time in do not work out suitable scheme.But by decades not
Disconnected effort, can obtain the sodium tetradecyl sulfate of higher degree by the preparation method of Optimal improvements,
Significant role is played in medicament research.
The United States Patent (USP) of Patent No. US 2088014 provides the synthesis side of several sodium tetradecyl sulfate
Method, such as method one: 2-Ethylhexyl Alcohol in methanol with methyl iso-butyl ketone (MIBK) generation condensation reaction, through dehydration,
The series reaction such as reduction, sulfonation prepare sodium tetradecyl sulfate.Such as method two: with 2-methyl-7-ethyl
Undecyl alcohol-4 is raw material, reacts in halo dihydroxy ester with anhydrous slufuric acid acid anhydride and chlorosulfonic acid, more neutralized,
The methods such as decompression prepare object.But said method one i.e. generates the impurity mixing of complexity in the first stage
Thing, is difficult to remove by common process, and high-pressure hydrogenation limits the practicality of method simultaneously.Method
High boiling halogenating agent is employed in two, expensive, and be difficult to remove residual, it is unfavorable for industrialization
Application.
Summary of the invention
In view of this, it is an object of the invention to provide the synthetic method of a kind of sodium tetradecyl sulfate, institute
Stating synthetic method synthesis technique stable, the sodium tetradecyl sulfate yield prepared is high, and quality is homogeneous, relevant
Content of material is low, is suitable for industrialization needs.
The synthetic method of a kind of sodium tetradecyl sulfate, the thick product of sodium tetradecyl sulfate has through lipotropy
Machine solvent extraction, collects organic facies.
In some embodiments, lipophylic organic solvents described in synthetic method of the present invention is acetic acid
At least one in ethyl ester, normal hexane, ether and petroleum ether.As respectively with ethyl acetate, normal hexane,
Ether or petroleum ether are extractant extraction, it is also possible to in ethyl acetate, normal hexane, ether and petroleum ether
Any two or three mixture be extractant extraction.Can certainly with ethyl acetate, normal hexane,
The mixture of ether and petroleum ether is extractant extraction.
In some preferred embodiments, described lipophylic organic solvents is the mixture of normal hexane and ether.
The mixed proportion of normal hexane and ether is not limited by the present invention, the arbitrary proportion mixing of normal hexane and ether
It is considered as being included in the scope of protection of the invention.
Preferably, normal hexane described in normal hexane and ether and ether volume ratio >=1:1.
In some embodiments, described in synthetic method of the present invention, the number of times of extraction is more than 3 times.
Such as 3 times, 4 times, 5 times, 6 times or 7 times.
In some embodiments, synthetic method of the present invention also includes active carbon purification step.
In certain embodiments, described activated carbon purification is specially and dilutes the organic of collection with purified water
Phase, adds activated carbon, at 60～65 DEG C, mixing, sucking filtration in diluent.
Further, in some preferred embodiments, synthetic method of the present invention is at activated carbon purification
After also include the step that is dried.Described being dried can be, but not limited to as lyophilization.
The thick product of sodium tetradecyl sulfate of the present invention can be 1-hydroxyl-3 of any means synthesis,
5-dimethyl-4-chlorobenzene crude product can be the product arbitrarily containing PCMX.
In some embodiments, the thick product of sodium tetradecyl sulfate described in synthetic method of the present invention
After the preparation method of product is 7-Ethyl-2-Methyl-undecyl alcohol sulfonation, alkaline sodium salt regulation pH > 7, through organic
Solvent extraction obtains.
Further, in some preferred embodiments, the tetradecane described in synthetic method of the present invention
Organic solvent in the preparation method of the thick product of base sodium sulfate is ether or ethyl acetate.
Certainly, these those skilled in the art can use any one method to 7-Ethyl-2-Methyl-undecyl alcohol
Carrying out sulfonation, they are considered as being included in the scope of protection of the invention.
In some preferred embodiments, 7-Ethyl-2-Methyl-ten one described in synthetic method of the present invention
Alcohol sulfonation is specially 7-Ethyl-2-Methyl-undecyl alcohol and reacts sulfonation with chlorosulfonic acid.
In certain embodiments, 7-Ethyl-2-Methyl-undecyl alcohol is entered by synthetic method of the present invention
Row sulfonation is specially and is sufficiently mixed with absolute ether by chlorosulfonic acid, under temperature control, drips 7-Ethyl-2-Methyl-4-
Undecyl alcohol and the mixed liquor of ethyl acetate, completion of dropwise addition, react 2 hours.
This area is exactly that personnel are appreciated that alkaline sodium salt described in synthetic method of the present invention can be to appoint
What is in the sodium salt of alkalescence, such as sodium hydroxide, sodium carbonate etc..In some preferred embodiments, described alkali
Property sodium salt is sodium hydroxide.In certain embodiments, it is 10% sodium hydroxide.
In certain embodiments, described organic solvent extraction specially reactant liquor regulates to pH > 7
Stirring sucking filtration, by organic solvent extraction water phase, merges organic solvent phase, is dried, sucking filtration, and filtrate concentrates
To thickness.
The synthetic method of sodium tetradecyl sulfate of the present invention uses lipophylic organic solvents to myristyl
Sodium sulfate crude product extracts, and effectively removes process contaminants, it is to avoid use high boiling halogenating agent, behaviour
Make simplicity, with low cost.The sodium tetradecyl sulfate finished product purity simultaneously obtained is high, relevant content of material
Below 0.1%, quality controllable, it is suitable for the commercial production of sodium tetradecyl sulfate.
Detailed description of the invention
Below in conjunction with the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete
Describe, it is clear that described embodiment is only a part of embodiment of the present invention rather than all wholely
Embodiment.Based on the embodiment in the present invention, those of ordinary skill in the art are not making creativeness
The every other embodiment obtained under work premise, broadly falls into the scope of protection of the invention.
Below in conjunction with specific embodiment, the present invention will be described in detail.Wherein, 2-methyl-7-ethyl-4-ten
One alcohol is purchased from TCI company of Japan；Normal hexane is purchased from Mitsubishi Chemical；Absolute ether, dehydrated alcohol, chlorine sulphur
Acid, anhydrous sodium sulfate, sodium carbonate, activated carbon etc. are purchased from traditional Chinese medicines reagent.20L double-layer glass reaction kettle, 20L
Multifunctional reactor, rotary evaporator, 50L liquor separator, sub-cooled circulating pump are purchased from great Yan instrument,
2000 mass spectrographs are purchased from PE company of the U.S., and BS-1100+ electronic balance is purchased from Shanghai friend's limited public affairs of sound weighing apparatus
Department.
Embodiment 1:
Chlorosulfonic acid is sufficiently mixed with absolute ether, under temperature control, drips 7-Ethyl-2-Methyl-4-undecyl alcohol 20g
With the mixed liquor of ethyl acetate, completion of dropwise addition, react 2 hours.7-Ethyl-2-Methyl-4-undecyl alcohol is made to fill
Divide sulfonation, drip 10%NaOH solution, by PH regulation to alkalescence, stirring sucking filtration, extract by ethyl acetate
Water intaking phase, combined ethyl acetate phase, anhydrous Na2SO4It is dried overnight.Sucking filtration, filtrate is concentrated into thickness.
Purified water is added, after mixing, with normal hexane continuous extraction 3 times, extraction knot in above-mentioned viscous solution
Bundle, lower floor separates, concentrating under reduced pressure organic solvent.With purified water dilution uniformly, in diluent, addition is lived
Property charcoal, stirs 20 minutes, sucking filtration, and filtrate is entered freeze drying box and is dried hour, obtains sodium tetradecyl sulfate
Finished product 24g, productivity 82%, single the most miscellaneous is less than 0.1%, the most miscellaneous is less than 0.1%.
Embodiment: 2
Chlorosulfonic acid is sufficiently mixed with absolute ether, under temperature control, drips 7-Ethyl-2-Methyl-4-undecyl alcohol 20g
With the mixed liquor of ether, completion of dropwise addition, react 2 hours.Make the 7-Ethyl-2-Methyl abundant sulphur of-4-undecyl alcohol
Change, drip 10%NaOH solution, by PH regulation to alkalescence, stir sucking filtration, use ether aqueous phase extracted,
Merge ether phase, anhydrous Na2SO4It is dried overnight.Sucking filtration, filtrate is concentrated into thickness.
Purified water is added, after mixing, with petroleum ether continuous extraction 3 times, extraction knot in above-mentioned viscous solution
Bundle, lower floor separates, concentrating under reduced pressure organic solvent.With purified water dilution uniformly, in diluent, addition is lived
Property charcoal, stirs 20 minutes, sucking filtration, and filtrate is entered freeze drying box and is dried hour, obtains sodium tetradecyl sulfate
Finished product 25g, productivity 85%, single the most miscellaneous is less than 0.1%, the most miscellaneous is less than 0.1%.
Embodiment 3:
Chlorosulfonic acid is sufficiently mixed with absolute ether, under temperature control, drips 7-Ethyl-2-Methyl-4-undecyl alcohol 20g
With the mixed liquor of ethyl acetate, completion of dropwise addition, react 2 hours.7-Ethyl-2-Methyl-4-undecyl alcohol is made to fill
Divide sulfonation, drip 10%NaOH solution, by PH regulation to alkalescence, stirring sucking filtration, extract by ethyl acetate
Water intaking phase, combined ethyl acetate phase, anhydrous Na2SO4It is dried overnight.Sucking filtration, filtrate is concentrated into thickness.
Adding purified water in above-mentioned viscous solution, after mixing, with ether continuous extraction 3 times, extraction terminates,
Lower floor separates, concentrating under reduced pressure organic solvent.With purified water dilution uniformly, in diluent, add activated carbon,
Stirring 20 minutes, sucking filtration, filtrate is entered freeze drying box and is dried hour, obtains sodium tetradecyl sulfate finished product 24g,
Productivity 82%, single the most miscellaneous is less than 0.1%, the most miscellaneous is less than 0.1%.
Embodiment 4:
Chlorosulfonic acid is sufficiently mixed with absolute ether, under temperature control, drips 7-Ethyl-2-Methyl-4-undecyl alcohol 20g
With the mixed liquor of ether, completion of dropwise addition, react 2 hours.Make the 7-Ethyl-2-Methyl abundant sulphur of-4-undecyl alcohol
Change, drip 10%NaOH solution, by pH regulator to alkalescence, stir sucking filtration, use ether aqueous phase extracted,
Merge ether phase, anhydrous Na2SO4It is dried overnight.Sucking filtration, filtrate is concentrated into thickness.
Purified water is added, after mixing, with the mixture of normal hexane and ether with 2:1 in above-mentioned viscous solution
Volume ratio continuous extraction 3 times, extraction terminates, and lower floor separates, concentrating under reduced pressure organic solvent.With purified water
Dilution uniformly, adds activated carbon in diluent, stirs 20 minutes, and sucking filtration, filtrate enters freeze drying box
It is dried hour, obtains sodium tetradecyl sulfate finished product 21g, productivity 73%, single the most miscellaneous it is less than 0.1%, total miscellaneous little
In 0.1%.
Claims (10)
1. a synthetic method for sodium tetradecyl sulfate, the thick product of sodium tetradecyl sulfate is through lipotropy
Organic solvent extracts, and collects organic facies.
Synthetic method the most according to claim 1, described lipophylic organic solvents be ethyl acetate,
At least one in normal hexane, ether and petroleum ether.
Synthetic method the most according to claim 1, described lipophylic organic solvents is normal hexane and second
The mixture of ether, described normal hexane and ether volume ratio >=1:1.
Synthetic method the most according to claim 1, the number of times of described extraction is more than 3 times.
5., according to the synthetic method described in claim 1-4 any one, also include active carbon purification step.
Synthetic method the most according to claim 5, described activated carbon purification is specially dilute with purified water
Release the organic facies of collection, in diluent, add activated carbon, at 60～65 DEG C, mixing, sucking filtration.
7. according to the synthetic method described in claim 1-6 any one, described sodium tetradecyl sulfate
After the preparation method of thick product is 7-Ethyl-2-Methyl-undecyl alcohol sulfonation, alkaline sodium salt regulation pH > 7, warp
Organic solvent is obtained by extraction.
Synthetic method the most according to claim 7, described organic solvent is ether or ethyl acetate.
Synthetic method the most according to claim 7, described 7-Ethyl-2-Methyl-undecyl alcohol sulfonation tool
Body is that 7-Ethyl-2-Methyl-undecyl alcohol reacts sulfonation with chlorosulfonic acid.
Synthetic method the most according to claim 7, described alkaline sodium salt is sodium hydroxide.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2088021A (en) * | 1934-01-05 | 1937-07-27 | Union Carbide & Carbon Corp | Saturated tetradecyl oxygenated compounds |
| US2088014A (en) * | 1934-01-05 | 1937-07-27 | Union Carbide & Carbon Corp | Production of sulphuric acid derivatives of secondary alcohols |
| SU1051067A1 (en) * | 1982-01-21 | 1983-10-30 | Ленинградский химико-фармацевтический институт | Process for preparing sodium 2-methyl-7-ethylundecyl-4-sulfate |
| WO2014106312A1 (en) * | 2013-01-07 | 2014-07-10 | 东明俱进化工有限公司 | Method for producing high-purity sodium dodecyl sulfate |
-
2015
- 2015-05-18 CN CN201510253142.3A patent/CN106278961A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2088021A (en) * | 1934-01-05 | 1937-07-27 | Union Carbide & Carbon Corp | Saturated tetradecyl oxygenated compounds |
| US2088014A (en) * | 1934-01-05 | 1937-07-27 | Union Carbide & Carbon Corp | Production of sulphuric acid derivatives of secondary alcohols |
| SU1051067A1 (en) * | 1982-01-21 | 1983-10-30 | Ленинградский химико-фармацевтический институт | Process for preparing sodium 2-methyl-7-ethylundecyl-4-sulfate |
| WO2014106312A1 (en) * | 2013-01-07 | 2014-07-10 | 东明俱进化工有限公司 | Method for producing high-purity sodium dodecyl sulfate |
Non-Patent Citations (1)
| Title |
|---|
| 周艳等: ""十二烷基硫酸钠制备方法的探讨"", 《实验技术与管理》 * |
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