Sodium hyaluronate with full molecular weight distribution (mwd), and preparation method and use thereof
US-2024002551-A1 · Jan 4, 2024 · US
US9315404B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9315404-B2 |
| Application number | US-201113989929-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 5, 2011 |
| Priority date | Dec 7, 2010 |
| Publication date | Apr 19, 2016 |
| Grant date | Apr 19, 2016 |
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A process comprising contacting deionized water with one or more Strecker sulfonation reaction products of one or more halogenated alkyl ethers in the presence of sulfite, wherein the one or more Strecker sulfonation reaction products each comprise one or more inorganic salts on a dry basis and one or more surfactant components, form a filtration mixture; loading the filtration mixture into a high pressure filtration system containing a membrane having a membrane molecular weight cutoff allowing preferential passage of the inorganic salts, for example, of greater than or equal to 200 Daltons; wherein the high pressure filtration system is operated at a pressure greater than ambient pressure and is configured to cause crossflow of the filtration mixture along a surface of the membrane resulting in a permeate solution which substantially passes through the membrane and a retentate solution which substantially does not pass through the membrane; wherein the permeate comprises less than or equal to 15 weight percent surfactant component, based on the weight of the filtration mixture is provided.
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We claim: 1. A process comprising: conducting a Strecker sulfonation reaction of one or more alkyl ethers of 1,3-dihalo-2-propanol to form a Strecker sulfonation reaction product mixture which comprises disulfonate and monosulfonate surfactant components and one or more inorganic salts; contacting deionized water with the Strecker sulfonation reaction product mixture of one or more halogenated alkyl ethers, wherein the alkyl groups of the alkyl ethers comprise from 8 to 16 carbons, in the presence of sulfite, wherein the Strecker sulfonation reaction product mixture to form a filtration mixture; loading the filtration mixture into a high pressure filtration system containing a nanofiltration membrane having a membrane molecular weight cutoff allowing preferential passage of inorganic salts of greater than or equal to 200 Daltons; wherein the high pressure filtration system is operated at a pressure greater than ambient pressure and is configured to cause crossflow of the filtration mixture along a surface of the nanofiltration membrane resulting in a permeate solution which substantially passes through the nanofiltration membrane and a retentate solution which substantially does not pass through the nanofiltration membrane; wherein the permeate comprises less than or equal to 15 weight percent surfactant components, based on the total weight of the surfactant components in the filtration mixture. 2. A process comprising: conducting a Strecker sulfonation reaction of one or more alkyl ethers of 1,3-dihalo-2-propanol to form a Strecker sulfonation reaction product mixture which comprises disulfonate and monosulfonate surfactant components and one or more inorganic salts, wherein the alkyl groups of the alkyl ethers comprise from 8 to 16 carbon atoms, in the presence of sulfite, contacting the Strecker sulfonation reaction product mixture with one or more organic solvents selected from the group consisting of ethyl acetate, aliphatic and aromatic hydrocarbons, ethers, esters, and combinations thereof to form an extraction mixture; allowing the extraction mixture to separate into an aqueous phase and an organic phase; and separating the aqueous phase from the organic phase; adding deionized water to the aqueous phase to form a filtration mixture: loading the filtration mixture into a high pressure filtration system containing a nanofiltration membrane having a membrane molecular weight cutoff of greater than or equal to, for example, 200 Daltons; wherein the high pressure system is operated at a pressure greater than ambient pressure and is configured to cause crossflow of the filtration mixture along a surface of the nanofiltration membrane resulting in a permeate solution which substantially passes through the nanofiltration membrane and a retentate solution which substantially does not pass through the nanofiltration membrane; wherein the permeate comprises less than or equal to 15 weight percent surfactant components, based on the total weight of the surfactant components in the filtration mixture. 3. The process according to claim 1 , wherein the one or more halogenated alkyl ethers comprise one or more alkyl ethers of 1,3-dichloro-2-propanol wherein the alkyl group is selected from the group of alkyls having eight or more carbon atoms. 4. The process according to claim 1 , wherein the high pressure filtration system is a operated at a pressure from 200 psi to 1000 psi. 5. The process according to claim 1 , wherein the high pressure filtration system is operated at a temperature from 25 to 55° C. 6. The process according to claim 1 , further comprising: bringing the pressure of the high pressure filtration system to ambient pressure; removing the permeate solution from the high pressure filtration system; adding to the high pressure filtration system a mass of deionized water substantially equal to the weight of the permeate solution removed from the high pressure system; raising the pressure of the high pressure system to a pressure greater than ambient pressure. 7. The process according to claim 1 , wherein the retentate solution comprises less than or equal to 1 weight percent inorganic salt content based on the total weight of the retentate solution. 8. The process according to claim 1 , further comprising: contacting the Strecker sulfonation reaction product mixture with an oxidizing agent prior to formation of the filtration mixture. 9. The process according to claim 1 , further comprising: filtering the filtration mixture with a non-nanofiltration filter having a particle retention size of equal to or greater than 1 micron prior to loading the filtration mixture into the high pressure filtration system. 10. The process according to claim 1 , wherein the one or more inorganic salts are selected from sodium sulfite, sodium bisulfate, sodium sulfate, sodium bisulfate, and sodium chloride, and their potassium counterparts. 11. The process according to claim 1 , wherein the Strecker sulfonation reaction product mixture each comprise between 40 and 60 percent by weight on a dry basis of the one or more inorganic salts. 12. The process according to claim 1 , wherein the extraction mixture comprises between 25 and 60 percent by weight on a dry basis of the Strecker sulfonation reaction product mixture. 13. The process of according to claim 1 , wherein the surfactant component of the Strecker sulfonation reaction product mixture each comprise one or more disulfonated alkyl ethers, one or more monosulfonated alkyl ethers, or a combination thereof. 14. The process according to claim 1 , wherein the retentate solution comprises between 10 and 50 percent by weight of a surfactant component.
Nanofiltration · CPC title
Separation; Purification · CPC title
with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom · CPC title
Multistage treatment of water, waste water or sewage · CPC title
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