GREEN CHEMISTRY OF TAURINE. Vitaworks, LLC

Transcription

1 GREEN CHEMISTRY OF TAURINE Development of an Atom-Efficient Process Songzhou Hu, Ph.D Vitaworks, LLC

2 Traditional Ethylene Oxide Process 2 Addition O + NaHSO 3 HO SO 3 Na (Sexton) Ammonolysis NH 3 N H 2 SO 3 Na (Nicodemus) Neutralization H 2 SO 4 H 2 N SO 3 H + Na 2 SO 4 (Wang) Sexton, A. R., U.S. Pat. No. 2,820,818 (1958) Nicodemus, O.; Schmidt, W., U.S. Pat. No. 1,932,907 (1933) Wang, D., China Pat. Appl. No (2009)

3 Green Chemistry Metrics of Traditional EO Process 3 AE (Atom Efficiency) Mol. Wt of Product Mol. Wt of All Substances Formed E Factor Mass of Raw Materials Mass of Product Mass of Product AE: 63.8% E Factor: 1.28 Overall Yield: 75%

4 Traditional EO Process (Prior to 2014) 4 Ethylene Oxide Sodium Bisulfite Ammonolysis Sodium Taurinate H 2 SO 4 Sodium Sulfate Sodium Sulfate Mother Liquor (Hazardous Waste) AE: 63.8% E Factor: 1.28 Overall Yield: 75%

5 Traditional EO Process: Disadvantages 5 Low to moderate overall yield 75% to 80% Large amount of hazardous waste mother liquor Containing 25% sodium ditaurinate and tritaurinate Coproduction of large amount of sodium sulfate 1 Ton sodium sulfate for 1 ton of taurine

6 Vitaworks GEN 1 Technology (Adopted 2015) 6 Ethylene Oxide Sodium Bisulfite NaOH Ammonolysis Sodium Taurinate H 2 SO 4 Sodium Sulfate Hazardous Mother Liquor Recycling Sodium Sulfate AE: 63.8% E Factor: 0.65 Overall Yield: >95% Hu, S. U.S. Pat. No. 9,428,451 B2 (2016) Hu, S. U.S. Pat. No. 9,573,890 B2 (2017) Hu, S. U.S. Pat. No. 10,040,755B2 (2018)

7 Vitaworks GEN 1 Technology 7 Advantages High overall yield: 90% to 95% No waste mother liquor Disadvantage Coproduction of large amount of sodium sulfate 1 Ton sodium sulfate for 1 ton of taurine

8 Vitaworks GEN 2 Technology (2015) 8 NaOH Ethylene Oxide Sodium Bisulfite Ammonolysis Sodium Taurinate SO 2 Sodium Bisulfite Sodium Sulfite AE: 100% E Factor: 0.05 Overall Yield: >95% Hu, S. U.S. Pat. No. 8,609,890 B1 (2013) Hu, S. U.S. Pat. No. 9,061,976 B1 (2015) Hu, S. U.S. Pat. No. 10,040,755B2 (2018)

9 Vitaworks GEN 2 Technology (2017) 9 Ethylene Oxide NaHSO 3 SO 2 NaOH Bipolar Membrane Electrodialysis Isethionic Acid NH 3 Ammonolysis AE: 100% E Factor: <0.01 Overall Yield: >99% Hu, S. U.S. Pat. No. 9,593,076 B2 (2017) Hu, S. U.S. Pat. No. 10,040,755B2 (2018)

10 Vitaworks GEN 2 Technology (2017) 10 Advantages High Overall Yield: 95% to 99% No hazardous waste mother liquor No inorganic salt Disadvantage Problematic recycling process Foul smell for plant and product Inconvenient starting material

11 Vitaworks GEN 3 Technology (2017) 11 S + O 2 SO 2 NH 3 Ethylene Oxide Ammonium Bisulfite Ammonium Isethionate Ammonolysis AE: 100% E Factor: <0.01 Overall Yield: >99% Hu, S. U.S. Pat. No. 9,745,258 B1 (2017) Hu, S. U.S. Pat. No. 9,815,778 B1 (2017) Hu, S. U.S. Pat. No. 9,926,265 B1 (2018)

12 Vitaworks GEN 3 Technology (2017) 12 Advantages High Overall Yield: 95% to 99% No waste mother liquor No inorganic salt None Disadvantage

13 Hu Process of 13 O N H 2 + S + O 2 + NH 3 SO 3 H AE: 100% E Factor: <0.01 Overall Yield: >99% Hu, S. U.S. Pat. No. 9,061,976 B1 (2015) Hu, S. U.S. Pat. No. 9,593,076 B2 (2017) Hu, S. U.S. Pat. No. 9,745,258 B1 (2017) Hu, S. U.S. Pat. No. 10,040,755B2 (2018)