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WO 2015/079239 A2 4 June 2015 (04.06.2015) W P O P C T

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WO 2015/079239 A2 4 June 2015 (04.06.2015) W P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/079239 A2 4 June 2015 (04.06.2015) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C02F 1/02 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/GB2014/053520 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 27 November 2014 (27.1 1.2014) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/909,449 27 November 2013 (27. 11.2013) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: TATE & LYLE TECHNOLOGY LIMITED GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, [GB/GB]; 1 Kingsway, London WC2B 6AT (GB). TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (72) Inventors: DENTEL, David A.; 10558 Eastern Shore Blvd, Apt 2023, Spanish Fort, Alabama 36527 (US). DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, BOUTZALE, Wayne N.; 1806 Spanish Drive, Saraland, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Alabama 36571 (US). FARLEY, Edward; 41W200 GW, KM, ML, MR, NE, SN, TD, TG). Hearthstone Court, St Charles, Illinois 601 75 (US). Published: (74) Agents: SMYTH, Gyles Darren et al; Fairfax House, 15 Fulwood Place, London, Greater London WC1V 6HU — without international search report and to be republished (GB). upon receipt of that report (Rule 48.2(g)) (54) Title: WASTE TREATMENT PROCESS - (57) Abstract: A waste treatment process and system is described, which finds application in dechlorinating carbohydrates and/or hydrolysing dimethyl formamide and/or dimethyl acetamide in a waste stream. The process includes treating the waste stream with o base at a pH of from 11 to 14, and at a temperature of from 200 to 330 °F. Waste Treatment Process The present invention relates to a waste treatment system for a waste stream. The waste treatment system as described herein may enable solvent recovery from the waste stream. Furthermore, the waste treatment system as described herein may improve the biodegradability of this waste stream by any subsequent biological waste treatment system. The treatment reduces the content of organic compounds in the waste stream, and thus may render it more amenable to further processing. Moreover, the chemical oxygen demand (COD) of the waste stream may be reduced by the treatment described herein. The invention is as defined in the attached claims and the following numbered clauses. Thus, according to the invention, there is provided: 1. A method of treating a waste stream, wherein the waste stream includes at least one of chlorinated carbohydrate, dimethyl formamide and dimethyl acetamide, wherein the method comprises: treating the waste stream with base at a pH of from 11 to 14, and at a temperature of from 200 to 330 °F, in order to achieve at least one of dechlorination of said chlorinated carbohydrate, hydrolysis of said dimethyl formamide t o give dimethylamine, and hydrolysis of said dimethyl acetamide to give dimethylamine. 2. A method according t o clause 1, wherein the waste stream includes said chlorinated carbohydrate and the treatment achieves dechlorination of the chlorinated carbohydrate. 3. A method according t o clause 1, where the waste stream includes said dimethyl formamide and the treatment achieves hydrolysis of the dimethyl formamide t o give dimethylamine. 4. A method according t o clause 1, where the waste stream includes said dimethyl acetamide and the treatment achieves hydrolysis of the dimethyl acetamide t o give dimethylamine. 5. A method according t o clause 1, wherein the waste stream includes said chlorinated carbohydrate, said dimethyl formamide and said dimethyl acetamide and the treatment achieves dechlorination of the chlorinated carbohydrate, hydrolysis of the dimethyl formamide to give dimethylamine, and hydrolysis of the dimethyl acetamide to give dimethylamine. 6. A method according t o clause 1, wherein the waste stream is from a sucralose production process. 7. A method according t o clause 1, wherein the waste stream includes sodium chloride, for example 5 t o 20 wt% sodium chloride. 8. A method according t o clause 1 wherein the base is aqueous alkali solution. 9. A method according t o clause 8, wherein the base is aqueous sodium hydroxide solution, potassium hydroxide solution, or aqueous ammonia. 10. A method according t o clause 9, wherein the base is aqueous sodium hydroxide solution. 11. A method according t o clause 10, wherein the base is from 10 t o 50% w/w sodium hydroxide solution. 12. A method according t o clause 11, wherein the base is from 23 t o 32% w/w sodium hydroxide solution. 13. A method according t o clause 1, wherein the p H of the treatment is from 11 to 13.5. 14. A method according t o clause 13, wherein said pH is from 12 to 13. 15. A method according t o clause 1, wherein the temperature of the treatment is from 210 t o 280 °F, for example at 215 t o 220 °F, at 240 t o 250 °F, at 250 to 260 °F, or at 260 to 270 °F. 16. A method according t o clause 1, wherein the pressure of the treatment is from 20 to 75 psig, for example from 25 to 35 psig or from 30 to 35 psig. 17. A method according t o clause 1, wherein the waste stream is in aqueous medium, or in aqueous solution. 18. A method according t o any of clauses 3 to 5, wherein dimethylamine is recovered from the treatment. 19. A method according t o clause 18, wherein the dimethylamine is recovered by distillation. 20. A method according t o clause 19, wherein the dimethylamine is converted into dimethylformamide. 21. A method according t o clause 1, wherein the treatment achieves dechlorination of said chlorinated carbohydrate, and at least one of hydrolysis of said dimethyl formamide t o give dimethylamine, and hydrolysis of said dimethyl acetamide to give dimethylamine. In other words, in the embodiment of clause 21, the treatment process dechlorinates chlorinated carbohydrates and hydrolyses one or both of dimethyl formamide and dimethyl acetamide. 22. A method according t o any preceding clause, wherein the treated stream is discharged after treatment. As used in the claims, the above numbered clauses and herein, by "the treatment achieves dechlorination" it is meant that some dechlorination occurs, that is, some chloride is liberated from chlorinated carbohydrate that is present. For example, at least 50%, or at least 70%, or at least 90% of the chlorine present in the chlorinated carbohydrate may be liberated as chloride. As used in the claims, the above numbered clauses and herein, by "the treatment achieves hydrolysis" is meant that some hydrolysis occurs, that is, some dimethyl formamide and/or dimethyl acetamide that is present is hydrolysed to afford dimethylamine. For example, at least 50%, or at least 70%, or at least 90% of dimethyl formamide that is present in the waste stream may be hydrolysed to afford dimethylamine, and/or at least 50%, or at least 70%, or at least 90% of dimethyl acetamide that is present in the waste stream may be hydrolysed to afford dimethylamine. A specific embodiment of a waste treatment system is as follows. The system is described by reference to particular features, but these are not intended to limit the invention or its scope, which is as set out in the subsequent claims. All documents mentioned herein are expressly incorporated by reference in their entirety. Brief description of the drawings: Figure 1 is a process flow diagram illustrating a waste treatment process. Figure 2 is a graph which shows the rate of hydrolysis of dimethylacetamide (DMAc) in an aqueous solution of DMAc and NaOH at 50 °C and 75 °C. Figure 3 is a graph which shows the rate of hydrolysis of DMAc in an aqueous solution of DMAc, dimethylformamide (DM F) (DMAc:DM F = 1:9 w/w) and NaOH at 90 °C. Figure 4 is a graph which shows the rate of hydrolysis of DM F in an aqueous solution of DM F and NaOH at 103 °C (starting DM Fconcentration = 700 ppm) Figure 5 is a graph which shows the rate of hydrolysis of DM F in an aqueous solution of DM F and NaOH at 25 °C (starting DM Fconcentration = 700 ppm). Figure 6 is a graph which shows the rate of hydrolysis of DM F in an aqueous solution of DM F and NaOH at 103 °C (starting DM Fconcentration = 2100 ppm). Figure 7 is a graph which shows the rate of hydrolysis of DM F in an aqueous solution of DM F (starting concentration = 700 ppm), DMA (dimethylamine, 3% w/w of reaction mixture) and NaOH (where indicated).
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