WO1995030473A1 - Method of separating a solute from other solutes - Google Patents
Method of separating a solute from other solutes Download PDFInfo
- Publication number
- WO1995030473A1 WO1995030473A1 PCT/GB1995/001022 GB9501022W WO9530473A1 WO 1995030473 A1 WO1995030473 A1 WO 1995030473A1 GB 9501022 W GB9501022 W GB 9501022W WO 9530473 A1 WO9530473 A1 WO 9530473A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solute
- membrane
- solution
- insolubilised
- derivative
- Prior art date
Links
Classifications
-
- 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
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/04—Feed pretreatment
-
- 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
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
-
- 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
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- 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
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/16—Feed pretreatment
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2311/00—Details relating to membrane separation process operations and control
- B01D2311/04—Specific process operations in the feed stream; Feed pretreatment
Definitions
- This invention relates to a method of separating a solute from one or more other solutes in a solution and particularly, but not exclusively, to the use of this method in the manufacture of N-acyl taurate derivatives, and especially in the manufacture of sodium N-cocoyl, N-methyl taurate (SCMT).
- SCMT sodium N-cocoyl, N-methyl taurate
- one solute may be a desired reaction product and the other solute(s) may be undesired by-product(s).
- membranes may be used to effect a separation.
- ultrafiltration, nanofiltration and reverse osmosis membranes are all characterized by the maximum molecular weight solute which will pass
- Ultrafiltration membranes have a molecular weight cut-off (MWCO) which defines the maximum molecular weight solute which will pass through the membrane.
- MWCO molecular weight cut-off
- Ultrafiltration membranes typically have a molecular weight cut-off of between about 2000 and 200000 daltons.
- Reverse osmosis is characterized typically by the %. retention or rejection of a solute, e.g. sodium chloride , or calcium chloride.
- Reverse osmosis membranes generally have a sodium chloride retention from about 30%. to 99%..
- Nanofiltrations membranes are intermediate between reverse osmosis membranes and ultrafiltration membranes. Nanofiltration membranes typically have a molecular weight cut-off of 2000 daltons to a sodium chloride retention of 30%.
- a method of separating a solute from one or more other solutes in a solution which method comprises
- insolubilising the solute to be separated from the solution and passing the mixture of insolubilised solute and the remaining solution in contact with a membrane, the molecular weight cut-off of the membrane being such that the solute(s) remaining in solution pass through the membrane but the insolubilised solute does not.
- Ultrafiltration is typically carried out using pressures of from about 0.6 to 1.0 MPa (6 to 10 bar) and nanofiltration typically uses pressures of about 4 to 5 MPa (40 to 50 bar); whereas reverse osmosis uses high pressures of over 6 MPa (> 60 bar).
- the membrane used will be chosen according to the molecular weights of the solutes in the solution to be processed.
- the membrane is a nanofiltration membrane or an ultrafiltration membrane.
- nanofiltration membrane we mean a membrane with a molecular weight cut-off of 2000 daltons to a sodium chloride retention of 30%; and by
- ultrafiltration membrane we mean a membrane with a
- the solute which is to be separated from the solution is selectively insolubilised, eg. by a physical process.
- the solute may be selectively insolubilised by cooling the solution to a sub-ambient temperature.
- the exact temperature to which the solution should be cooled prior to contact with the membrane will, of course, depend upon the temperature at which any particular solute crystallizes out of solution so that it is in the form of insoluble particles which cannot pass through the membrane.
- the temperature to which the solution will need to be cooled will also therefore depend upon the molecular weight cut-off of the membrane being used.
- the solute could also be insolubilised, in
- the solute to be separated from the solution may also be insolubilised by a chemical process, for example by a chemical precipitation reaction.
- the method of the present invention has been found to be particularly suitable for separating an N-acyl taurate derivative from other solute contaminants in a reaction mixture, wherein the N-acyl taurate derivative is
- an N-acyl taurate derivative by reacting an acid chloride with an aminoalkane sulphonic acid in aqueous medium in the presence of an acid neutralizer and removing a precipitate of the N-acyl taurate derivative directly from the reaction mixture by effecting filtration of the reaction mixture at a sub-ambient temperature.
- Diafiltration is a membrane filtration technique whereby the process fluid is washed free of small species with a molecular weight less than the molecular weight cut-off of the membrane.
- water is added continuously to the reaction mixture to maintain a constant volume during the filtration process.
- the solids contents and filtration temperatures are varied, so that the N-acyl taurate
- the method of the present invention allows the preparation, for example, of N-acyl taurate derivatives based on lauric (C12), myristic (C14), palmitic (C16), stearic (C18) or oleic (C18 mono unsaturated) acids.
- the invention allows the preparation of sodium N-cocoyl, N-methyl taurate (SCMT).
- SCMT sodium N-cocoyl, N-methyl taurate
- SCMT is an anionic surface active sulphonate that is used as a detergent in the personal care industry and, in particular, in gum-sensitive toothpastes because of the unique compatibility of SCMT with strontium salts which are used in these products.
- SCMT-type detergents Several processes have been described for the preparation of SCMT-type detergents, but the only process which is presently employed commercially is the Schotten-Baumann reaction, in which an acid chloride is reacted in aqueous medium with an aminoalkane sulphonic acid in the presence of an acid neutralizer such as sodium hydroxide.
- SCMT is prepared commercially by the reaction:
- the hydrogen chloride produced is immediately quenched with the aqueous base to form sodium chloride.
- reaction mixture contains approximately 15%. of sodium chloride (dry weight) which must be separated from the product in order to produce pure SCMT (>95%. active).
- SCMT pure SCMT
- Other minor contaminants such as sodium N-methyl taurate and free coconut fatty acid must also be reduced or removed at the same time.
- the molecular size of the SCMT is close enough to that of sodium chloride for a significant loss of activity to occur through the membrane when this technique was applied to remove the sodium chloride.
- the use of ultrafiltration was not, therefore, thought to be
- JP 4149169 describes the manufacture of N-acyl taurate derivatives, where water is added to the f i na l reac t i on m i x tu re i n o rde r to d i s s o l ve the N-acyl taurate derivative, and the liquid is subjected to reverse osmosis.
- such a process is necessarily operated at high pressures in order to drive the water and sodium chloride through the membrane. This process is not, therefore, a satisfactory process for obtaining SCMT commercially.
- the method of the present invention provides an effective way of recovering the SCMT from the Schotten-Baumann reaction slurry.
- the method is also applicable to the manufacture of other N-acyl taurates.
- an N-acyl taurate may be prepared by reacting an acid chloride with an aminoalkane sulphonic acid in aqueous medium in the presence of an acid neutralizer (eg. sodium hydroxide), and the reaction mixture then subjected to the membrane to effect separation, the N-acyl taurate derivative being in the form of insoluble particles which cannot pass through the membrane.
- an acid neutralizer eg. sodium hydroxide
- the above-mentioned problem of the porosity of the membrane to SCMT is overcome by the precipitation of the SCMT such that it is substantially only present in the slurry as agglomerated insoluble particles.
- the precipitate can be obtained substantially free of chloride (e.g. sodium chloride) and other contaminants.
- diafiltration is used; most preferably with water being added continuously to the slurry mixture to maintain a constant volume.
- the preferred way of insolubilizing the N-acyl taurate derivative is by cooling the reaction mixture.
- the insolubilised solute and the remaining solution are passed in contact with the membrane at a temperature below about 10oC, more preferably, at a temperature below about 6oC, and most preferably, below about 3oC.
- the SCMT slurry is suitably adjusted to approximately 15 to 30%., e.g. about 24%., solids prior to contact with the membrane.
- the addition of water may be stopped and the concentration of the slurry increased as the permeate continues to pass through the membrane.
- the process may be stopped at a concentration of up to 30-34%..
- the SCMT Upon warming to 25oC, the SCMT becomes fully water-soluble again up to about 34%., and is therefore suitable for spray drying or any other alternative form of isolation of the pure 95%. SCMT.
- the ultrafiltration trials have been carried out using a PCI Membrane Systems BUF unit with one 4ft (1.22m) module, having a filtration area of 0.9m 2 .
- FP100 membranes have been used which are PVDF and have a nominal molecular weight cut-off of 100,000 daltons.
- the slurry is pumped using a single speed positive displacement pump so that the rate of passage of the slurry through each module in the ultrafiltration unit is about 22 litres/min.
- the actual volume displaced by the pump will be a function of the size of the pump. (On a full-size unit, a variable speed pump could be used).
- the SCMT slurry made by the Schotten-Baumann process is currently about 32-3%%. solids. This is difficult to process directly, due to possible problems associated with pumping and, more importantly, because of the pressure drop across the modules leading to significantly reduced flux. Air intake into the slurry can also be a problem, especially when the slurry is warm and/or high in solids, and some of the trial batches have been carried out without agitation, due to air within the feed. A slow gentle agitator can be used to solve this problem.
- the SCMT slurry has been diluted to approximately 24%. solids (warm) before being naturally cooled, and then chilled to a temperature of 6oC, in order to bring the SCMT out of solution.
- SCMT slurry (23.1%. solids) in a storage vessel was heated to 50oC with agitation and 235.5 kg of the slurry was then weighed and charged into the feed vessel, and the contents were mixed for about a minute to produce a
- the slurry in the feed vessel was then allowed to cool naturally, without agitation, until the temperature had dropped to 20.6oC. Glycol cooling was then applied to the feed vessel jacket and the heat exchanger. The plant was then configured for recycle, and the slurry pumped from the feed vessel, through the heat exchanger, to the UF module. Both retentate and permeate were returned to the feed vessel. When the feed temperature had reduced to 9°C, the agitator on the feed vessel was started and recycle
- the plant was then configured for filtration (retentate being returned to the feed vessel, and permeate fed into a receiver).
- the inlet pressure on the UF module was increased to 6.0 bar by means of the pressure control valve, and the run started.
- chilled diafiltration water ⁇ 6oC
- a sample of the slurry in the feed vessel was then analysed for salt content, and the slurry recycled through the UF module until the result was known.
- the salt content was known to be below the required limit, the plant was again configured for filtration, and the slurry
- a sample of slurry was then analysed for %. solids, activity, sodium chloride content. N-methyl taurine content, and pH. The product was then filled off into kegs.
- Table 1 gives the analytical results of both the initial and desalted slurry.
- Example 2 The method described in Example 1 was repeated except that the production unit was run on AN 620 membranes. These membranes are polyacryIonitrile in nature and have a nominal molecular weight cut-off of 25.000 daltons.
- Table 2 gives the analytical results of both the initial and desalted slurry.
- Example 1 The method described in Example 1 was repeated using a small laboratory unit with the FP100 membranes except that sodium N-myristoyl. N-methyl taurate (SMMT) was used.
- SMMT N-methyl taurate
- Table 3 gives the analytical results of both the initial and desalted slurry.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9524786A GB2294413B (en) | 1994-05-04 | 1995-05-04 | Method of separating a solute from other solutes |
CA002164502A CA2164502A1 (en) | 1994-05-04 | 1995-05-04 | Method of separating a solute from other solutes |
JP7528774A JPH09503962A (en) | 1994-05-04 | 1995-05-04 | How to separate solutes from other solutes |
AU24134/95A AU2413495A (en) | 1994-05-04 | 1995-05-04 | Method of separating a solute from other solutes |
EP95918055A EP0707511A1 (en) | 1994-05-04 | 1995-05-04 | Method of separating a solute from other solutes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9408772.3 | 1994-05-04 | ||
GB9408772A GB9408772D0 (en) | 1994-05-04 | 1994-05-04 | Manufacture of N-ACYL taurate derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995030473A1 true WO1995030473A1 (en) | 1995-11-16 |
Family
ID=10754494
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1995/001022 WO1995030473A1 (en) | 1994-05-04 | 1995-05-04 | Method of separating a solute from other solutes |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0707511A1 (en) |
JP (1) | JPH09503962A (en) |
AU (1) | AU2413495A (en) |
CA (1) | CA2164502A1 (en) |
GB (1) | GB9408772D0 (en) |
WO (1) | WO1995030473A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100870344B1 (en) * | 2006-12-29 | 2008-11-25 | 주식회사 효성 | Refining Method and Apparatus for High Purity 2,6-Naphthalene Dicarboxylic acid |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04149169A (en) * | 1990-10-08 | 1992-05-22 | Kawaken Fine Chem Co Ltd | Surfactant |
US5252218A (en) * | 1992-06-02 | 1993-10-12 | Cargill, Incorporated | Process for separating solid particulates from a nonaqueous suspension |
-
1994
- 1994-05-04 GB GB9408772A patent/GB9408772D0/en active Pending
-
1995
- 1995-05-04 CA CA002164502A patent/CA2164502A1/en not_active Abandoned
- 1995-05-04 AU AU24134/95A patent/AU2413495A/en not_active Abandoned
- 1995-05-04 JP JP7528774A patent/JPH09503962A/en active Pending
- 1995-05-04 EP EP95918055A patent/EP0707511A1/en not_active Ceased
- 1995-05-04 WO PCT/GB1995/001022 patent/WO1995030473A1/en not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04149169A (en) * | 1990-10-08 | 1992-05-22 | Kawaken Fine Chem Co Ltd | Surfactant |
US5252218A (en) * | 1992-06-02 | 1993-10-12 | Cargill, Incorporated | Process for separating solid particulates from a nonaqueous suspension |
Non-Patent Citations (3)
Title |
---|
DATABASE WPI Section Ch Week 2792, Derwent World Patents Index; Class D25, AN 92-223456 * |
H. GASPER:: "Druckbetriebene Verfahren der industriellen Cross-flow-Membrantechnik", CHEMIE-TECHNIK, vol. 22, no. 2, HEIDELBERG, DE, pages 64 - 67 * |
R. BOTT:: "Mikroporöse Filtermedien für die Kuchenfiltration", CHEMIE-INGENIEUR-TECHNIK, vol. 62, no. 9, WEINHEIM, DE, pages 718 - 724 * |
Also Published As
Publication number | Publication date |
---|---|
JPH09503962A (en) | 1997-04-22 |
GB9408772D0 (en) | 1994-06-22 |
AU2413495A (en) | 1995-11-29 |
CA2164502A1 (en) | 1995-11-16 |
EP0707511A1 (en) | 1996-04-24 |
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