CN106187832B - A kind of method for preparing or purifying ion-pairing agent - Google Patents
A kind of method for preparing or purifying ion-pairing agent Download PDFInfo
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- CN106187832B CN106187832B CN201610562988.XA CN201610562988A CN106187832B CN 106187832 B CN106187832 B CN 106187832B CN 201610562988 A CN201610562988 A CN 201610562988A CN 106187832 B CN106187832 B CN 106187832B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of methods for preparing or purifying ion-pairing agent, include the following steps：Step 1: being dissolved in a solvent after ion-pairing agent is directly dissolved in solvent or is handled, ion-pairing agent solution is obtained；Step 2: removing the impurity in ion-pairing agent solution by way of filtering, ion-pairing agent clear solution is obtained；Step 3: the solvent in removal ion-pairing agent clear solution, obtains high-purity ion to reagent solid or solution.A kind of method for preparing or purifying ion-pairing agent of the present invention has the advantages that：Solves the technical issues of ion-pairing agent is difficult to reach no UV absorption or extremely weak UV absorption standard.
Description
Technical field
Preparation or method of purification the present invention relates to a kind of reagent.
Background technology
Ion-pairing agent is that one kind can be applied to high performance liquid chromatography, for improving the separating effect of high performance liquid chromatography
Reagent.When using the stronger sample of liquid chromatography analysis ionizing power, retention time of the sample on reverse-phase chromatographic column
It is very short or do not retain, at this moment to add in corresponding ion-pairing agent.Ion-pairing agent is formed by strong hydrophilicity ion,
It is combined with the ion in analyte, is formed in the molecule that can retain on pillar.It that is, will be by using ion-pairing agent
Analysis sample is kept here, is the good method of the highly polar organic acid of analysis and organic base, is widely used in biochemistry, materia medica and
The fields such as petrochemical industry.
The type and concentration of ion-pairing agent have large effect to separating effect.Common ion-pairing agent is selected from packet
Sulfonate containing C2-C30 or the quaternary ammonium salt comprising C4-C30.Such as 1- sodium pentanesulfonates, 1- pentanesulfonic acids potassium, 1- hexane sulfonic acid
Sodium, 1- sodium heptanesulfonates, sodium 1-octanesulfonate, 1- decane sulfonates, tetrabutylammonium hydroxide (10% aqueous solution), tetrabutyl bromine
Change ammonium, dodecyl trimethyl ammonium chloride.According to the difference of ion-pairing agent structure, the hydrophobicity and hydrophily of ion-pairing agent
There were significant differences, can obtain satisfied separation by adjusting ion-pairing agent concentration and organic solvent concentration in application process and imitate
Fruit.
Detector in high performance liquid chromatography belongs to important component, effect be by sample composition in chromatography column effluent and
The variation of content is converted into the signal for deciphering, and common detector has UV absorption, fluorescence, differential refraction, chemiluminescence etc..
Wherein, ultraviolet absorption detector is one of most common detector of high performance liquid chromatography, and almost all of liquid chromatograph is all matched
There is this detector, its main feature is that sensitivity is higher, the range of linearity is wide, and noise is low, especially suitable for gradient elution, to absorbing by force
Substance detectable limit does not destroy sample up to 1 nanogram after detection, available for reagent preparation, and can connect and make with any detector
With.
Ion-pairing agent has great influence in the optical characteristics of ultraviolet band during high performance liquid chromatography detection.
The good ion-pairing agent of quality should not absorb or absorb in ultraviolet band considerably less.If ion-pairing agent has stronger
The accuracy of ultraviolet absorption characteristic, then severe jamming high performance liquid chromatography ultraviolet absorption detector, causes testing result to be distorted.Institute
Ultraviolet absorption characteristic with, ion-pairing agent is to determine one of key index whether its is best in quality.
Under normal conditions, the ion-pairing agent being prepared contains the impurity for absorbing ultraviolet light, how to remove impurity, reaches
It is required that harsh UV absorption standard is one of Key technique problem for preparing or purifying ion-pairing agent.
Invention content
The example of the present invention is intended to overcome more than technical problem, proposes that one kind can solve ion-pairing agent and reach without ultraviolet
Absorption or the preparation of extremely weak UV absorption typical problem or the method for purifying ion-pairing agent.
In order to solve the above technical problems, according to the first aspect of the invention, provide and a kind of prepare or purify ion-pairing agent
Method, wherein, include the following steps：
Step 1: being dissolved in a solvent after ion-pairing agent is directly dissolved in solvent or is handled, ion pair examination is obtained
Agent solution；
Step 2: removing the impurity in ion-pairing agent solution by way of filtering, it is molten to obtain ion-pairing agent clarification
Liquid；
Step 3: the solvent in removal ion-pairing agent clear solution, obtains high-purity ion to reagent solid or solution.
The step 1 includes recrystallizing ion-pairing agent 1-10 time, obtains ion-pairing agent semi-finished product, will described in from
Son re-dissolves reagent semi-finished product and obtains ion-pairing agent solution in a solvent.
The ion-pairing agent sulfonate comprising C2-C30 or quaternary ammonium salt comprising C4-C30 in molecular formula.
The ion-pairing agent is preferably：1- sodium pentanesulfonates, 1- pentanesulfonic acids potassium, 1- sodium hexanesulfonates, 1- heptane sulphurs
Sour sodium, sodium 1-octanesulfonate, 1- decane sulfonates, tetrabutylammonium hydroxide, tetrabutylammonium bromide, trimethyl chlorination
Ammonium.
Solvent in the step 1 to three include the alcohols containing C1-C10, water, the ether compound containing C2-C10,
Tetrahydrofuran, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, dimethyl sulfoxide, the lipoid substance of C2-C12, N- methyl
Pyrrolidones, the aromatic hydrocarbons of C6-C12, the alkanes of C4-C15, petroleum ether or C1-C6 halides.
Step 1 to solvent described in three is preferably methanol, ethyl alcohol, n-butanol, water, ether, methyl tertiary butyl ether, tetrahydrochysene furan
It mutters, n,N-Dimethylformamide, n,N-dimethylacetamide, dimethyl sulfoxide, ethyl acetate, N-Methyl pyrrolidone, benzene, first
Benzene, dimethylbenzene, mesitylene, petroleum ether, dichloromethane, 1,2- dichloroethanes.
The mode filtered in the step 2 is natural filtration, pressurizing filter or is filtered under diminished pressure.
The mode filtered in the step 2 includes being filtered by filter paper, film or diatomite.
The mode filtered in the step 2 further includes and activated carbon is added in into ion-pairing agent solution, then by filter paper,
Film or diatomite are filtered.
In the step 3 remove ion-pairing agent clear solution in solvent mode for rotary evaporation, vacuum drying,
Heat drying or high temperature drying.
The film is high molecula resin film or ceramic membrane.
The high molecula resin film is preferably nylon material film or polytetrafluoroethylene (PTFE) material film.
The aperture of the filter paper, high molecula resin film or ceramic membrane is less than 5 microns.Optimum condition is：Filter paper, high score subtree
The aperture of adipose membrane or ceramic membrane is less than 1 micron.
The high-purity ion reaches the purity and UV absorption index of reagent：When ion titration purity reaches 90%-
110%, UV absorbance detection condition is that 10% high-purity ion is high performance liquid chromatography (HPLC) to reagent aqueous solution, water used
In the case of grade deionized water, 1 centimetre of cuvette, Testing index reaches：Under 210nm wavelength, absorptivity A≤0.2；220nm
Under wavelength, absorptivity A≤0.12；Under 230nm wavelength, absorptivity A≤0.08；Under 260nm wavelength, absorptivity A≤
0.04；Under 500nm wavelength, absorptivity A≤0.04.
The high-purity ion preferably reaches the purity and UV absorption index of reagent：When ion titration purity reaches
98%-102%, UV absorbance detection condition are that 10% high-purity ion is high performance liquid chromatography to reagent aqueous solution, water used
(HPLC) in the case of grade deionized water, 1 centimetre of cuvette, Testing index reaches：Under 210nm wavelength, absorptivity A≤0.1；
Under 220nm wavelength, absorptivity A≤0.06；Under 230nm wavelength, absorptivity A≤0.04；Under 260nm wavelength, absorptivity A
≤0.02；Under 500nm wavelength, absorptivity A≤0.02.
The preparation of the present invention or the method for purifying ion-pairing agent have the following advantages that compared with the prior art:The present invention is logical
It crosses ion-pairing agent dissolving in a solvent, obtains ion-pairing agent solution, ion pair examination is then removed by way of filtering
Impurity in agent solution obtains ion-pairing agent clear solution, then removes the solvent in ion-pairing agent clear solution, obtains height
Purity ion can solve ion-pairing agent and be difficult to reach no UV absorption or extremely weak ultraviolet to the method for reagent solid or solution
The technical issues of absorption standard.
Description of the drawings
It, below will be to example or existing skill in order to illustrate more clearly of example of the present invention or technical solution of the prior art
Attached drawing is briefly described needed in art description, it should be apparent that, the accompanying drawings in the following description is only the present invention
Some examples, for those of ordinary skill in the art, without creative efforts, can also be according to this
A little attached drawings obtain other attached drawings.
Fig. 1 is the preparation of the present invention or purifies the flowage structure schematic diagram of the method for ion-pairing agent.
Specific embodiment
To make the objectives, technical solutions, and advantages of the present invention of greater clarity, With reference to embodiment and join
According to attached drawing, the present invention is described in more detail.It should be understood that these descriptions are merely illustrative, and it is not intended to limit this hair
Bright range.In addition, in the following description, the description to known features and technology is omitted, to avoid this is unnecessarily obscured
The concept of invention.
Fig. 1 is the preparation of the present invention or purifies the flowage structure schematic diagram of the method for ion-pairing agent, as shown in Figure 1, originally
Invention provides a kind of method for preparing or purifying ion-pairing agent, includes the following steps：
Step 1: being dissolved in a solvent after ion-pairing agent is directly dissolved in solvent or is handled, ion pair examination is obtained
Agent solution；
Step 2: removing the impurity in ion-pairing agent solution by way of filtering, it is molten to obtain ion-pairing agent clarification
Liquid；
Step 3: the solvent in removal ion-pairing agent clear solution, obtains high-purity ion to reagent solid or solution.
It should be noted that step 1 includes recrystallizing ion-pairing agent 1-10 times, ion-pairing agent semi-finished product are obtained,
Ion-pairing agent semi-finished product are re-dissolved and obtain ion-pairing agent solution in a solvent.
In the further example of the present invention, ion-pairing agent is the sulfonate comprising C2-C30 or the quaternary ammonium comprising C4-C30
Salt.
It should be noted that the ion-pairing agent of the present invention can be 1- sodium pentanesulfonates, 1- pentanesulfonic acids potassium, 1- hexanes
Sodium sulfonate, 1- sodium heptanesulfonates, sodium 1-octanesulfonate, 1- decane sulfonates, tetrabutylammonium hydroxide, tetrabutylammonium bromide or ten
Dialkyl group trimethyl ammonium chloride.
In the further example of the present invention, solvent includes the alcohols containing C1-C10, water, the ethers chemical combination containing C2-C10
Object, tetrahydrofuran, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, dimethyl sulfoxide, the lipoid substance of C2-C12, N-
Methyl pyrrolidone, the aromatic hydrocarbons of C6-C12, the alkanes of C4-C15, petroleum ether or C1-C6 halides.
It should be noted that the solvent of the present invention can be methanol, ethyl alcohol, n-butanol, water, ether, methyl tertiary butyl ether, four
Hydrogen furans, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, dimethyl sulfoxide, ethyl acetate, N-Methyl pyrrolidone, benzene,
Toluene, dimethylbenzene, mesitylene, petroleum ether, dichloromethane or 1,2- dichloroethanes.
In the further example of the present invention, the mode filtered in step 2 is natural filtration, pressurizing filter or depressurized
Filter.
In the further example of the present invention, the mode that is filtered in step 2 is included and was carried out by filter paper, film or diatomite
Filter.Wherein, the mode filtered in step 2 also comprising adding in activated carbon into ion-pairing agent solution, then by filter paper, film or
Diatomite is filtered.
It should be noted that filtering can remove the impurity in ion-pairing agent solution, it is molten to obtain ion-pairing agent clarification
Liquid.Filtering, which has, screens out effect, and when solution passes through filtrate, the particle bigger than filtering layer hole is trapped, and then, filtering layer hole is gradual
Become smaller, smaller particle is also trapped.Filtering also has contact cohesion, is not deposited the tiny floccule body or de- steady of removal
Particle is adsorbed when being contacted with filtrate, and after filtrate adsorption-flocculation body, suction-operated further enhances.
The mode that the solvent in ion-pairing agent clear solution is removed in the further example of the present invention, in step 3 is rotation
Turn evaporation, vacuum drying, heat drying or high temperature drying.
It should be noted that rotary evaporation process is heated at constant temperature, revolving bottle constant speed rotary, due to fluid sample and rotation
The effect of centripetal force and frictional force between bottle, fluid sample form large area film in revolving bottle inner surface, and heating surface area is big, steam
Send out efficient.Meanwhile active force effectively inhibits the boiling of sample caused by the rotation of sample.
In the further example of the present invention, film is high molecula resin film or ceramic membrane.Wherein, on the one hand chemistry is steady for ceramic membrane
It is qualitative good, it can acidproof, alkaline-resisting or organic solvent.On the other hand, ceramic membrane mechanical strength is big, can back flush.In addition, ceramic membrane
Anti-microbe ability is strong, and high temperature resistant, pore-size distribution is narrow, and separative efficiency is high.
In the further example of the present invention, high molecula resin film is nylon material film or polytetrafluoroethylene (PTFE) material film.Wherein,
Nylon material film has good hydrophily, and the soda acid of resistance to debita spissitudo is applicable not only to the aqueous solution containing acid-base property, is also suitable
In containing organic solvent, example alcohols, hydro carbons, ethers, esters, ketone, benzene and substituted benzene, dimethylformamide, dimethyl Asia
Sulfone etc., the scope of application are most wide.Polytetrafluoroethylene (PTFE) material membrane crystallization degree is high, and molecular orientation tightly arranges, and voidage is small, and removal is molten
The effect of impurity in liquid is good.
In the further example of the present invention, the aperture of filter paper, high molecula resin film or ceramic membrane is less than 5 microns, preferably hole
Diameter is less than 1 micron.
The high-purity ion of the present invention reaches the purity and UV absorption index of reagent：
(1) when ion titration purity reaches 90%-110%, UV absorbance detection condition is 10% high-purity ion to examination
In the case of agent aqueous solution, 1 centimetre of cuvette and high performance liquid chromatography (HPLC) grade deionized water, Testing index reaches：210nm
Under wavelength, absorptivity A≤0.2；Under 220nm wavelength, absorptivity A≤0.12；Under 230nm wavelength, absorptivity A≤
0.08；Under 260nm wavelength, absorptivity A≤0.04；Under 500nm wavelength, absorptivity A≤0.04.
(2) when ion titration purity reaches 98%-102%, UV absorbance detection condition is 10% high-purity ion to examination
In the case of agent aqueous solution, 1 centimetre of cuvette and high performance liquid chromatography (HPLC) grade deionized water, Testing index reaches：210nm
Under wavelength, absorptivity A≤0.1；Under 220nm wavelength, absorptivity A≤0.06；Under 230nm wavelength, absorptivity A≤
0.04；Under 260nm wavelength, absorptivity A≤0.02；Under 500nm wavelength, absorptivity A≤0.02.
It should be noted that the computational methods of ion titration purity remove theoretical ion concentration for actually detected ion concentration.
If certain ion concentration is more higher than theoretical value in sample, ion titration purity will be more than 100%.If for example, tetrabutyl
Contain NH4Br in ammonium bromide, bromide ion therein can be caused higher than the bromide ion concentration in theoretically pure tetrabutylammonium bromide, from
Son titration purity result will be more than 100%.
Below in conjunction with specific example, the present invention will be further described, certain specific example be for illustrate the present invention without
It is for limiting the scope of the invention.
Example 1
0.5 ton of 83 kilograms of sodium sulfite and deionized water are added in 1000L reaction kettles, stirring forms clear solution,
1- bromo pentane silane 120kg are added, be heated to reflux and are stirred 1 hour.After reaction, it is cooled to room temperature, decompression water removal has a large amount of
Solid is precipitated.Solid crude product 120 kg is obtained with centrifuge rejection filter.Solid crude product recrystallize in ethanol obtain for 3 times from
Son is to reagent semi-finished product.HPLC detections UV absorption is unqualified.By the dissolving of ion-pairing agent semi-finished product in ethanol, ion is obtained
To reagent solution.
It stirs 30 minutes at a temperature of 10 kilograms, 50 DEG C of activated carbon of addition in ion-pairing agent solution, is filtered with diatomite,
Obtain high-purity 1- pentanesulfonic acid sodium solutions.
High-purity 1- pentanesulfonic acids sodium solution is obtained into high-purity 1- sodium pentanesulfonates by rotary evaporation.
Wherein, ion titration purity reaches 98%-102%；UV absorbance detection condition is：10% high-purity ion is to examination
Agent aqueous solution, 1 centimetre of cuvette and HPLC grades of deionized waters, Testing index reach：Under 210nm wavelength, absorptivity A≤0.1；
Under 220nm wavelength, absorptivity A≤0.06；Under 230nm wavelength, absorptivity A≤0.04；Under 260nm wavelength, absorptivity A
≤0.02；Under 500nm wavelength, absorptivity A≤0.02.
Example 2
100 kilograms of tetrabutylammonium bromide crude product is obtained by the reaction in 1- bromobutane and tri-butylamine.Tetrabutylammonium bromide is thick
Product recrystallizes in water once obtains ion-pairing agent semi-finished product.HPLC detections UV absorption is unqualified.By ion-pairing agent
Semi-finished product are dissolved in water, and obtain ion-pairing agent solution.
Ion-pairing agent solution is filtered under diminished pressure by polytetrafluoroethylene (PTFE) material film, the hole of polytetrafluoroethylene (PTFE) material film
Diameter is less than 0.2 micron, and tetrabutyl phosphonium bromide aqueous ammonium is obtained after filtering.
The above-mentioned tetrabutyl phosphonium bromide aqueous ammonium being obtained by filtration is obtained into high-purity four by rotary evaporation and high temperature drying
Butylammonium bromide.
Wherein, ion titration purity reaches 98%-102%；UV absorbance detection condition is：10% high-purity ion is to examination
Agent aqueous solution, 1 centimetre of cuvette and HPLC grades of deionized waters, Testing index reach：Under 210nm wavelength, absorptivity A≤0.1；
Under 220nm wavelength, absorptivity A≤0.06；Under 230nm wavelength, absorptivity A≤0.04；Under 260nm wavelength, absorptivity A
≤0.02；Under 500nm wavelength, absorptivity A≤0.02.
Example 3
Ion is titrated into purity and the underproof 1- sodium heptanesulfonates of UV absorbance detection are dissolved in water, recrystallization is primary
Obtain ion-pairing agent semi-finished product.HPLC detects UV absorption still underproof ion-pairing agent semi-finished product.Ion pair is tried
Agent semi-finished product are dissolved in water, and obtain ion-pairing agent solution.
Ion-pairing agent solution by diatomite is filtered under diminished pressure, obtains 1- heptanesulfonic acid sodium water solutions.
1- heptanesulfonic acids sodium water solution is obtained into high-purity 1- sodium heptanesulfonates by rotary evaporation and high temperature drying.
Wherein, ion titration purity reaches 98%-102%；UV absorbance detection condition is：10% high-purity ion is to examination
Agent aqueous solution, 1 centimetre of cuvette and HPLC grades of deionized waters, Testing index reach：Under 210nm wavelength, absorptivity A≤0.1；
Under 220nm wavelength, absorptivity A≤0.06；Under 230nm wavelength, absorptivity A≤0.04；Under 260nm wavelength, absorptivity A
≤0.02；Under 500nm wavelength, absorptivity A≤0.02.
It should be understood that the above-mentioned specific embodiment of the present invention is used only for exemplary illustration or explains the present invention's
Principle, without being construed as limiting the invention.Therefore, that is done in the case of without departing from spirit and scope of the present invention is any
Modification, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.In addition, appended claims purport of the present invention
Covering the whole variations fallen into scope and boundary or this range and the equivalent form on boundary and repairing
Change example.
Claims (6)
1. a kind of method for preparing or purifying ion-pairing agent, includes the following steps：
Step 1: being dissolved after ion-pairing agent is handled in a solvent, ion-pairing agent solution is obtained；The step 1 includes：
Ion-pairing agent is recrystallized 1-10 times, ion-pairing agent semi-finished product is obtained, the ion-pairing agent semi-finished product is re-dissolved
Ion-pairing agent solution is obtained in a solvent；
Step 2: removing the impurity in ion-pairing agent solution by way of filtering, ion-pairing agent clear solution is obtained；Its
In, the mode filtered described in step 2 is filtered by film；The film is high molecula resin film or ceramic membrane；The height
Molecule resin film is nylon material film or polytetrafluoroethylene (PTFE) material film；
Step 3: the solvent in removal ion-pairing agent clear solution, obtains high-purity ion to reagent solid or solution.
2. preparation according to claim 1 or the method for purification ion-pairing agent, wherein, the ion-pairing agent, which is selected from, to be divided
Sulfonate comprising C2-C30 or the quaternary ammonium salt comprising C4-C30 in minor.
3. preparation according to claim 1 or the method for purification ion-pairing agent, wherein, the solvent includes containing C1-
Alcohols, water, the ether compound containing C2-C10, tetrahydrofuran, N,N-dimethylformamide, the N of C10, N- dimethylacetamides
Amine, dimethyl sulfoxide, the lipoid substance of C2-C12, N-Methyl pyrrolidone, the aromatic hydrocarbons of C6-C12, the alkane of C4-C15, oil
The halides of ether or C1-C6.
4. preparation according to claim 1 or the method for purification ion-pairing agent, wherein, the side filtered described in step 2
Formula is natural filtration, pressurizing filter or is filtered under diminished pressure.
5. preparation according to claim 1 or the method for purification ion-pairing agent, wherein, the side filtered described in step 2
Formula further includes and activated carbon is added in into ion-pairing agent solution, then is filtered by film.
6. preparation according to claim 1 or the method for purification ion-pairing agent, wherein, deionization is removed described in step 3
Mode to the solvent in reagent clear solution is rotary evaporation, vacuum drying, heat drying or high temperature drying.
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| CN102020571A (en) * | 2009-09-23 | 2011-04-20 | 天津市化学试剂研究所 | Preparation method of tetramethylammonium bromide |
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| CN102351742A (en) * | 2011-08-25 | 2012-02-15 | 天津市化学试剂研究所 | Preparation method of ion-pair chromatography reagent sodium decane-1-sulfonate |
| CN103145591A (en) * | 2013-02-20 | 2013-06-12 | 上海晶纯实业有限公司 | Ion pair chromatographic-grade reagent sodium 1-octanesulfonate purifying process |
| CN105461597A (en) * | 2015-12-18 | 2016-04-06 | 上海阿拉丁生化科技股份有限公司 | Method for preparing ion pair chromatographic grade reagent sodium 1-octanesulfonate |
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|---|---|---|---|---|
| CN102020571A (en) * | 2009-09-23 | 2011-04-20 | 天津市化学试剂研究所 | Preparation method of tetramethylammonium bromide |
| CN102050763A (en) * | 2009-11-03 | 2011-05-11 | 江苏永华精细化学品有限公司 | Method for preparing 1-pentanesulfonic acid sodium salt concentrate |
| CN102351741A (en) * | 2011-08-25 | 2012-02-15 | 天津市化学试剂研究所 | Method for preparing and purifying paired ion chromatography reagent sodium hexanesulfonate |
| CN102351742A (en) * | 2011-08-25 | 2012-02-15 | 天津市化学试剂研究所 | Preparation method of ion-pair chromatography reagent sodium decane-1-sulfonate |
| CN103145591A (en) * | 2013-02-20 | 2013-06-12 | 上海晶纯实业有限公司 | Ion pair chromatographic-grade reagent sodium 1-octanesulfonate purifying process |
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