CN109134317A - A kind of method that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid - Google Patents
A kind of method that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid Download PDFInfo
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- CN109134317A CN109134317A CN201811049436.4A CN201811049436A CN109134317A CN 109134317 A CN109134317 A CN 109134317A CN 201811049436 A CN201811049436 A CN 201811049436A CN 109134317 A CN109134317 A CN 109134317A
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- camphorsulfonic acid
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- membrane electrodialysis
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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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/44—Ion-selective electrodialysis
- B01D61/445—Ion-selective electrodialysis with bipolar membranes; Water splitting
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention discloses a kind of methods that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid, using bipolar membrane electrodialysis device, salt room first into bipolar membrane electrodialysis membrane stack is passed through L-10- camphorsulfonic acid ammonium salt solution, acid compartment and alkaline chamber into bipolar membrane electrodialysis membrane stack each lead into deionized water, and the anode chamber and cathode chamber into bipolar membrane electrodialysis membrane stack each lead into strong electrolytic solution；Then applying direct current at bipolar membrane electrodialysis membrane stack both ends can be realized by L-10- camphorsulfonic acid ammonium conversion preparation L-10- camphorsulfonic acid.The conversion ratio of L-10- camphorsulfonic acid ammonium may be up to 98% or more in bipolar membrane electrodialysis conversion process of the present invention, and the purity of obtained product L-10- camphorsulfonic acid is up to 99% or more.The preparation method is easy to operate, without consuming any chemical reagents, avoids traditional handicraft ion-exchange and is led to the problem of using a large amount of chemical reagent consumptions of rear ion exchange resin regeneration bring and secondary pollution.
Description
Technical field
The present invention relates to a kind of methods that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid, belong to organic acid production technology
Field.
Background technique
Camphorsulfonic acid is the derivative of camphor, has chiral corresponding body structure, can be divided into left and right rotation according to its chemical characteristic
Structure, wherein l-camphor sulfonic acid (L-10- camphorsulfonic acid) is widely used in the industries such as medicine, light industry and daily use chemicals.Currently, chemical
Synthesis L-10- camphorsulfonic acid mainly passes through first artificial camphor sulfonic acid ammonium salt solution, then obtains L-10- camphorsulfonic acid by splitting
Then ammonium carries out continuous ionic exchange system by fixed bed and obtains L-10- camphorsulfonic acid solution.Often there is production weeks for the process
Phase is long, and total recovery is relatively low, and product purity is poor, also needs further to isolate and purify, in addition, the resin after ion exchange also needs
It is regenerated, needs to consume a large amount of reagent, while a large amount of waste water can be generated, secondary pollution is caused to environment.
In view of the above problems, Chinese patent CN105461596A proposes a kind of to be converted to camphorsulfonic acid by camphorsulfonic acid ammonium
Process for cleanly preparing, the technical process include: that (1) material liquid carries out ceramic membrane filter, obtain dialyzate；(2) ceramic membrane is dialysed
Liquid, which enters, carries out ion exchange in continuous ionic exchange system, obtain camphorsulfonic acid solution；(3) camphorsulfonic acid solution is carried out anti-
Osmosis concentration obtains concentrate；(4) MVR concentration is carried out to camphorsulfonic acid concentrate, then camphorsulfonic acid crystalline substance is obtained by crystallization
Body.However, still having used ion exchange system during the process for cleanly preparing, can not solve the above problems.
Bipolar membrane electrodialysis can be at low voltage by hydrolysis as a kind of green, environmental protection, energy-efficient membrane separation technique
From for H+And OH-, therefore can a step by organic and inorganic salt convert corresponding bronsted lowry acids and bases bronsted lowry, in the process without chemical reagent consumption, nothing
By-product generates.However, there is no convert L-10- camphorsulfonic acid ammonium by bipolar membrane electrodialysis method to prepare L-10- camphor at present
The report of sulfonic acid.
Summary of the invention
For the drawbacks described above for overcoming the prior art, the present invention provides a kind of bipolar membrane electrodialysis to prepare L-10- camphor sulphur
The method of acid, to realize the production process of low energy consumption, green, environmental protection.
For achieving the above object, the present invention adopts the following technical scheme:
The method that bipolar membrane electrodialysis of the present invention prepares L-10- camphorsulfonic acid, includes the following steps:
Using bipolar membrane electrodialysis device, the salt room first into bipolar membrane electrodialysis membrane stack is passed through L-10- camphorsulfonic acid
Ammonium salt solution, acid compartment and alkaline chamber into bipolar membrane electrodialysis membrane stack each lead into deionized water, into bipolar membrane electrodialysis membrane stack
Anode chamber and cathode chamber each lead into strong electrolytic solution；Then apply direct current at bipolar membrane electrodialysis membrane stack both ends
It realizes and preparation L-10- camphorsulfonic acid is converted by L-10- camphorsulfonic acid ammonium, i.e., Bipolar Membrane dissociates in acid compartment under the action of direct current
The H of generation+L-10- camphorsulfonic acid is generated with L-10- camphorsulfonic acid anion binding from salt room to acid compartment that migrate from, in alkaline chamber
The OH that Bipolar Membrane dissociation generates-Ammonium hydroxide is generated in conjunction with from the ammonium ion that salt room is migrated into alkaline chamber.
Membrane stack arrangement mode in the bipolar membrane electrodialysis device sets gradually as positive electrode-anode chamber-Bipolar Membrane-
[acid compartment-anion-exchange membrane-salt room-cation-exchange membrane-alkaline chamber-Bipolar Membrane]nCathode chamber-negative electrode, number of repeat unit are
N, n 1-1000.
The content of L-10- camphorsulfonic acid ammonium is 10-200g/L in the L-10- camphorsulfonic acid ammonium salt solution being passed through into salt room.
The strong electrolytic solution being passed through into anode chamber and cathode chamber is sodium sulphate or sodium nitrate solution, concentration 0.01-
1.0mol/L.Anode chamber and cathode chamber are cascaded, so that two pole room middle-jiao yang, function of the spleen and stomach total ion concentrations and anion total amount are kept
It is constant, maintain anion-cation balance in electrolyte.
The positive electrode and the material of negative electrode are that corrosion resistant titanium applies ruthenium；Compartment between adjacent ions exchange membrane includes
Acid compartment, alkaline chamber and the salt room is made of the gasket with runner and grid, spacer thickness 0.8mm.
In operational process, first by each compartment feed liquid by wriggling pump circulation 5-30 minutes, the bubble in membrane stack is discharged.
In operational process, the line stream that anode chamber, cathode chamber, acid compartment, alkaline chamber and salt room solution flow is controlled by peristaltic pump
Speed is 3-10cm/s, avoids concentration polarization phenomenon.
In operational process, constant voltage operation, the upper limit that current density is arranged is 10-100mA/cm2。
After bipolar membrane electrodialysis converts, the conductivity of L-10- camphorsulfonic acid ammonium salt solution can drop to 500 μ S/cm with
Under.
The conversion ratio of L-10- camphorsulfonic acid ammonium may be up to 98% or more in bipolar membrane electrodialysis conversion process of the present invention, obtain
To the purity of product L-10- camphorsulfonic acid be up to 99% or more.
Compared with prior art, the beneficial effects of the present invention are embodied in:
The present invention carries out conversion preparation L-10- camphor to L-10- camphorsulfonic acid ammonium salt solution with bipolar membrane electrodialysis for the first time
Sulfonic acid can directly dissociate water using Bipolar Membrane in the process and generate H+And OH-Advantage, one-step method by L-10- camphorsulfonic acid ammonium convert
For L-10- camphorsulfonic acid ammonium and ammonium hydroxide, obtained product purity is higher.The method, which avoids, uses amberlite in traditional handicraft
The method that rouge carries out ion exchange, to also avoid a large amount of chemical reagent consumptions of resin regeneration bring and two after ion exchange
Secondary pollutant is led to the problem of.Therefore, conversion preparation L-10- camphor is carried out to L-10- camphorsulfonic acid ammonium salt solution by Bipolar Membrane
Sulfonic acid is a kind of economic, green, environmental protection production method, has important industrial application value.
Detailed description of the invention
Fig. 1 is the schematic illustration that bipolar membrane electrodialysis of the present invention prepares L-10- camphorsulfonic acid.
Specific embodiment
The method that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid is further described by the following examples.
Embodiment 1:
The present embodiment uses bipolar membrane electrodialysis device as shown in Figure 1, and membrane stack arrangement mode is positive electrode-anode chamber-
Bipolar Membrane-[acid compartment-anion-exchange membrane-salt room-cation-exchange membrane-alkaline chamber-Bipolar Membrane]nCathode chamber-negative electrode repeats
Unit number n is 5.Positive electrode and the material of negative electrode are that corrosion resistant titanium applies ruthenium in membrane stack, between adjacent ions exchange membrane every
Room includes that acid compartment and alkaline chamber are made of the gasket with runner and grid, spacer thickness 0.8mm.Cation used in membrane stack
Exchange membrane, anion-exchange membrane and Bipolar Membrane are the CJMC-3, CJMA- of Hefei science and technology high molecular material Science and Technology Ltd. production
3 and CJBPM-2, single film effective area are 189cm2(9cm×21cm)。
Anode chamber and cathode chamber are cascaded, and are passed through 500mL 0.3mol/L Na2SO4Aqueous solution as strong electrolyte,
Salt room into bipolar membrane electrodialysis membrane stack is passed through L-10- camphorsulfonic acid ammonium salt solution (the conductivity 13mS/ of 1000mL 100g/L
Cm) acid compartment into bipolar membrane electrodialysis membrane stack and alkaline chamber each lead into 800mL deionized water.In experimentation, each compartment is molten
The line flow velocity that liquid flows in membrane stack is 4cm/s, and constant voltage operates, and membrane stack voltage is set as 20V, and the setting current density upper limit is
50mA/cm2。
Stopping when experiment operation drops to 500 μ S/cm to salt room conductivity, the conversion ratio of L-10- camphorsulfonic acid ammonium are
96.2%, L-10- camphorsulfonic acid product obtained in acid compartment is detected through liquid phase, and purity may be up to 99.8%, this shows to pass through
Bipolar membrane electrodialysis effectively can carry out L-10- camphorsulfonic acid ammonium to be converted into L-10- camphorsulfonic acid.
Embodiment 2:
Bipolar membrane electrodialysis device used in the present embodiment is the same as embodiment 1.
Anode chamber and cathode chamber are cascaded, and are passed through 500mL 0.3mol/L Na2SO4Aqueous solution as strong electrolyte,
Salt room into bipolar membrane electrodialysis membrane stack is passed through L-10- camphorsulfonic acid ammonium salt solution (the conductivity 26mS/ of 1000mL 200g/L
Cm) acid compartment into bipolar membrane electrodialysis membrane stack and alkaline chamber each lead into 800mL deionized water.In experimentation, each compartment is molten
The line flow velocity that liquid flows in membrane stack is 4cm/s, and constant voltage operates, and membrane stack voltage is set as 15V, and the setting current density upper limit is
50mA/cm2。
Stopping when experiment operation drops to 500 μ S/cm to salt room conductivity, the conversion ratio of L-10- camphorsulfonic acid ammonium are
98.1%, L-10- camphorsulfonic acid product obtained in acid compartment is detected through liquid phase, and purity may be up to 99.5%, this shows to pass through
Bipolar membrane electrodialysis effectively can carry out L-10- camphorsulfonic acid ammonium to be converted into L-10- camphorsulfonic acid.
Embodiment 3:
Bipolar membrane electrodialysis device used in the present embodiment is the same as embodiment 1.
Anode chamber and cathode chamber are cascaded, and are passed through 500mL 0.3mol/L Na2SO4Aqueous solution as strong electrolyte,
Salt room into bipolar membrane electrodialysis membrane stack is passed through L-10- camphorsulfonic acid ammonium salt solution (the conductivity 26mS/ of 1000mL 200g/L
Cm) acid compartment into bipolar membrane electrodialysis membrane stack and alkaline chamber each lead into 800mL deionized water.In experimentation, each compartment is molten
The line flow velocity that liquid flows in membrane stack is 4cm/s, and constant voltage operates, and membrane stack voltage is set as 20V, and the setting current density upper limit is
50mA/cm2。
Stopping when experiment operation drops to 300 μ S/cm to salt room conductivity, the conversion ratio of L-10- camphorsulfonic acid ammonium are
98.8%, L-10- camphorsulfonic acid product obtained in acid compartment is detected through liquid phase, and purity may be up to 99.4%, this shows to pass through
Bipolar membrane electrodialysis effectively can carry out L-10- camphorsulfonic acid ammonium to be converted into L-10- camphorsulfonic acid.
Claims (9)
1. a kind of method that bipolar membrane electrodialysis prepares L-10- camphorsulfonic acid, it is characterised in that include the following steps:
Using bipolar membrane electrodialysis device, it is molten that the salt room first into bipolar membrane electrodialysis membrane stack is passed through L-10- camphorsulfonic acid ammonium
Liquid, acid compartment and alkaline chamber into bipolar membrane electrodialysis membrane stack each lead into deionized water, the sun into bipolar membrane electrodialysis membrane stack
Pole room and cathode chamber each lead into strong electrolytic solution；Then applying direct current at bipolar membrane electrodialysis membrane stack both ends can be realized
Preparation L-10- camphorsulfonic acid is converted by L-10- camphorsulfonic acid ammonium.
2. according to the method described in claim 1, it is characterized by:
Membrane stack arrangement mode in the bipolar membrane electrodialysis device sets gradually as positive electrode-anode chamber-Bipolar Membrane-[acid compartment-
Anion-exchange membrane-salt room-cation-exchange membrane-alkaline chamber-Bipolar Membrane]nCathode chamber-negative electrode, number of repeat unit n, n are
1-1000。
3. according to the method described in claim 1, it is characterized by:
The content of L-10- camphorsulfonic acid ammonium is 10-200g/L in the L-10- camphorsulfonic acid ammonium salt solution being passed through into salt room.
4. according to the method described in claim 1, it is characterized by:
The strong electrolytic solution being passed through into anode chamber and cathode chamber is sodium sulphate or sodium nitrate solution, concentration 0.01-
1.0mol/L。
5. according to the method described in claim 1, it is characterized by:
The positive electrode and the material of negative electrode are that corrosion resistant titanium applies ruthenium.
6. according to the method described in claim 1, it is characterized by:
In operational process, first by each compartment feed liquid by wriggling pump circulation 5-30 minutes, the bubble in membrane stack is discharged.
7. according to the method described in claim 1, it is characterized by:
In operational process, it is by the line flow velocity that peristaltic pump controls anode chamber, cathode chamber, acid compartment, alkaline chamber and the flowing of salt room solution
3-10cm/s avoids concentration polarization phenomenon.
8. according to the method described in claim 1, it is characterized by:
In operational process, constant voltage operation, it is 10-100mA/cm that current density, which is arranged,2。
9. according to the method described in claim 1, it is characterized by:
After bipolar membrane electrodialysis converts, conductivity≤500 μ S/cm of L-10- camphorsulfonic acid ammonium salt solution.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114288857A (en) * | 2021-12-31 | 2022-04-08 | 中国科学技术大学 | Method for preparing ultrahigh-concentration acid and alkali by overflow-type-saturated feeding bipolar membrane electrodialysis |
| CN114506961A (en) * | 2022-03-21 | 2022-05-17 | 青岛职业技术学院 | Method for extracting thioglycollic acid from tail liquid of thiourethane production |
| CN114672830A (en) * | 2020-12-24 | 2022-06-28 | 江苏优士化学有限公司 | Preparation method of organic acid |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114672830A (en) * | 2020-12-24 | 2022-06-28 | 江苏优士化学有限公司 | Preparation method of organic acid |
| CN114288857A (en) * | 2021-12-31 | 2022-04-08 | 中国科学技术大学 | Method for preparing ultrahigh-concentration acid and alkali by overflow-type-saturated feeding bipolar membrane electrodialysis |
| CN114288857B (en) * | 2021-12-31 | 2023-03-10 | 中国科学技术大学 | Method for preparing ultrahigh-concentration acid and alkali through overflow type-saturated feeding bipolar membrane electrodialysis |
| CN114506961A (en) * | 2022-03-21 | 2022-05-17 | 青岛职业技术学院 | Method for extracting thioglycollic acid from tail liquid of thiourethane production |
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| CN109134317B (en) | 2021-11-12 |
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