PROCESS SULFONATION TO PRODUCE TAURINE

Abstract

A process for producing taurine, comprising mixing aminoethanol sulfate ester (AES) and a carbonate or bicarbonate, or combination thereof, thus producing a reaction mixture, and heating the reaction mixture in the presence of a sulfite or a bisulfite, or combination thereof, such that taurine is formed.

Claims

1. A process for producing taurine comprising: mixing aminoethanol sulfate ester (AES) with a carbonate or bicarbonate, or combination thereof, thus producing a reaction mixture; and heating the reaction mixture in the presence of a sulfite or a bisulfite, or combination thereof, such that taurine is formed.

2. The process of claim 1, wherein the sulfite or bisulfite is present in the reaction mixture.

3. The process of claim 1, wherein a base is present in the reaction mixture.

4. The process of claim 3, wherein the base is chosen from an alkali metal hydroxide and ammonium hydroxide, and a combination thereof.

5. The process of claim 4, wherein the alkali metal hydroxide is sodium hydroxide.

6. The process of claim 5, wherein carbon dioxide is present in the reaction mixture.

7. The process of claim 1, wherein the mixing comprises mixing the aminoethanol sulfate ester (AES) with a carbonate or bicarbonate, or combination thereof, and with the sulfite or bisulfite, or combination thereof, thus producing the reaction mixture.

8. The process of claim 7, wherein the molar ratio of the sulfite or bisulfite, or combination thereof, to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 1.0 and less than about 3.0, and the molar ratio of the carbonate or bicarbonate, or combination thereof to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 0.1 and less than 1.0.

9. The process of claim 8, wherein the molar ratio of the sulfite or bisulfite, or combination thereof, to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 1.0 and less than 2.0.

10. The process of claim 8, wherein the molar ratio of the sulfite or bisulfite, or combination thereof, to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 1.0 and less than 1.8.

11. The process of claim 8, wherein the molar ratio of the sulfite or bisulfite, or combination thereof, to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 1.0 and less than 1.5.

12. The process of claim 1, wherein the sulfite or bisulfite, or combination thereof, is added to the reaction mixture before or during the step of heating the reaction mixture.

13. The process of claim 1, wherein the step of heating is performed in the presence of an inert gas.

14. A process for producing taurine, comprising: a) adding a first stream, a second stream, and third stream to a sulfonation vessel, wherein the first stream comprises aminoethanol sulfate ester (AES) and the second stream is chosen from a carbonate, a bicarbonate, or a combination of carbonate or bicarbonate, and the third stream comprises an aqueous solution of at least one of a sulfite or a bisulfite, or combination thereof; b) mixing the first, second and third streams in the sulfonation vessel, thus producing a reaction mixture; and c) subjecting the reaction mixture to heat in the presence of an inert gas such that taurine is formed.

15. The process of claim 14, wherein the molar ratio of the sulfite to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 1.0 and less than about 3.0, and the molar ratio of the carbonate or bicarbonate, or combination thereof to the aminoethanol sulfate ester (AES) in the reaction mixture is equal to or greater than 0.1 and less than 1.0.

16. The process of claim 14, wherein the first stream and the second stream are mixed in a first part of the sulfonation vessel, wherein materials from the first part of the sulfonation vessel are mixed and react with the third stream in a second part of the sulfonation vessel to form to taurine.

17. The process of claim 14, wherein the aminoethanol sulfate ester (AES) has a residence time of no more than four hours in the sulfonation vessel.

18. The process of claim 14, wherein the aminoethanol sulfate ester (AES) has a residence time of no more than two hours in the sulfonation vessel.

19. The process of claim 14, wherein the inert gas is chosen from nitrogen, argon, helium, and combinations thereof.

20. The process of claim 14, wherein the inert gas is nitrogen.

21-48. (canceled)

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0016] FIG. 1 is a process flow diagram of a continuous or semi-continuous taurine production process in accordance with aspects of the invention.

[0017] FIG. 2 depicts a drying apparatus for water removal in accordance with aspects of the invention.

[0018] FIG. 3 depicts an apparatus for sulfonation in accordance with aspects of the invention.

[0019] FIG. 4 depicts an apparatus for sulfonation in accordance with aspects of the invention.

DETAILED DESCRIPTION

[0020] It has now been discovered that the addition of a carbonate, a bicarbonate, or a combination thereof to a reaction mixture of aminoethanol sulfate ester (AES) and sulfite dramatically increases taurine yield and decreases production of undesirable taurine by-product, e.g., N-2-Aminoethyl-2-aminoethanesulfonic acid depicted in formula (i) below.

##STR00001##

[0021] In an aspect, a continuous or semi-continuous process comprises mixing (i) aminoethanol sulfate ester, (ii) a carbonate, a bicarbonate, or a combination thereof, and (iii) an aqueous solution of sulfite in a sulfonation vessel, thus producing a reaction mixture, and heating the reaction mixture in the presence of an inert gas, thus converting the aminoethanol sulfate ester via sulfonation to taurine. The carbonate or bicarbonate may be any suitable carbonate or bicarbonate, such as soda ash. In an embodiment, a convenient inexpensive salt such as sodium carbonate (Na.sub.2CO.sub.3) or sodium bicarbonate (NaHCO.sub.3) may be the source of carbonate/bicarbonate. Without being bound by theory, in an embodiment, carbon dioxide may be added to the reaction mixture to react and become an additional source of carbonate.

[0022] The aqueous solution of sulfite may be sodium sulfite or sodium bisulfite. In an aspect, when the sulfite is bisulfite, then a base may be added to raise the pH of the reaction mixture to a range of about 7.0 to about 8.3. In an embodiment, the base is chosen from an alkali metal hydroxide (e.g., sodium hydroxide) or ammonium hydroxide, or combination thereof.

[0023] In an aspect, a process comprises continuously or semi-continuously adding a first stream, a second stream, and a third stream to a sulfonation vessel, wherein the first stream comprises aminoethanol sulfate ester (AES), wherein the second stream comprises a carbonate, a bicarbonate, or a combination thereof, and wherein the third stream comprises an aqueous solution of a sulfite.

[0024] In an aspect, the process comprises continuously or semi-continuously mixing the first, second and third streams in the sulfonation vessel, thus producing a mixture. In an aspect, the process comprises continuously or semi-continuously subjecting the mixture to heat, wherein the AES is converted to more taurine and less undesirable taurine by-product, e.g., N-2-Aminoethyl-2-aminoethanesulfonic acid, than the same process except for the adding of the second stream to the sulfonation vessel. In an aspect, the step of continuously or semi-continuously subjecting the mixture to heat is performed in the presence of an inert gas. In an aspect, the process further comprises subjecting the mixture to a pressure greater than autogenous pressure. In an aspect, the aminoethanol sulfate ester (AES) has a residence time in the sulfonation vessel of no more than four (4) hours. In an embodiment, the aminoethanol sulfate ester (AES) has a residence time in the sulfonation vessel of no more than two (2) hours, the heat is a temperature of 110-155° C., and the mixture is subjected to a pressure of at least 100 psi. In an aspect, the sulfite is chosen from at least one of a sulfite or a bisulfite, or combination thereof, e.g., sodium sulfite, sodium bisulfite, or combination thereof. In an aspect, the process results in a taurine yield of at least 80%.

[0025] In an aspect, the adding of the carbonate and/or bicarbonate to the reaction mixture of AES and sulfite reduces the amount of sulfite and/or bisulfite required to obtain at least the same taurine yield in the same process except for the adding of the carbonate and/or bicarbonate to the reaction mixture of AES and sulfite and/or bisulfite. In an embodiment, the adding of the carbonate and/or bicarbonate to the reaction mixture of AES and sulfite reduces the mole ratio of sulfite to AES from about 1.8 and greater to about 1.2-1.3 to obtain at least the same taurine yield in the same process except for the adding of the carbonate and/or bicarbonate to the reaction mixture of AES and sulfite. In an embodiment, the adding of the carbonate and/or bicarbonate to the reaction mixture of AES and sulfite reduces by about 28% the mole ratio of sulfite to AES required to obtain at least the same taurine yield in the same process except for the adding of the carbonate and/or bicarbonate to the reaction mixture of AES and sulfite.

[0026] In an aspect, a process comprises continuously or semi-continuously adding a first stream, a second stream, and a third stream to a sulfonation vessel, wherein the first stream comprises aminoethanol sulfate ester (AES), the second stream is chosen from a carbonate, a bicarbonate, or a combination thereof, and the third stream comprises an aqueous solution of sulfite, wherein the first stream and the second stream are mixed in a first part of the sulfonation vessel. In an aspect, in a second part of the sulfonation vessel, the third stream is mixed with materials from the first part of the sulfonation vessel to form taurine.

[0027] In an embodiment, in addition to forming taurine, a carbamate may be formed. An example of carbamate is 2-(Carboxyamino)ethanesulfonic acid, and is depicted in formula (ii) below.

##STR00002##

[0028] In an embodiment, the carbamate in formula (ii) may be converted to taurine with the addition of an acid, such as concentrated sulfuric acid.

[0029] In an embodiment, pH adjustment in the sulfonation vessel provides increased taurine yield and less production of undesirable taurine by-product, e.g., N-2-Aminoethyl-2-aminoethanesulfonic acid, than the same process with the exception of no pH adjustment.

[0030] The inert gas may be any suitable inert gas, including but not limited to nitrogen, helium, argon, and combinations thereof. In a preferred embodiment, the inert gas is nitrogen. In an aspect the heating step is conducted at a temperature of at least 115° C. and a pressure greater than autogenous pressure. The presence of the inert gas subjects the mixture to the pressure greater than autogenous pressure. In an aspect, the heating step is conducted at a pressure of at least 50 psi, more preferably at least 100 psi, and even more preferably at least 200 psi. In an aspect, the process results in a taurine yield of at least 80%. In an aspect, the process results in at least a 95% AES conversion to taurine. In an aspect, the aminoethanol sulfate ester has a residence time of no more than four (4) hours in the vessel. This residence time of no more than four (4) hours of the aminoethanol sulfate ester in the reaction vessel during sulfonation conversion to taurine is a substantially less than the period of time for sulfonation in conventional MEA methods. In an aspect, the aminoethanol sulfate ester has a residence time of no more than two (2) hours in the vessel.

[0031] FIG. 1 is a process flow diagram of a continuous taurine production process in accordance with aspects of the invention. As shown in FIG. 1, a continuous taurine manufacturing process 100 comprises reacting step 102 wherein monoethanolamine (MEA) and sulfuric acid (H.sub.2SO.sub.4) are mixed and react to form the intermediate 2-aminoethyl hydrogen sulfate ester (AES). Reacting step 102 may comprise continuously conveying a stream of MEA and a stream of sulfuric acid to an AES synthesis reactor, and continuously conveying effluent 120 out of that AES synthesis reactor. Effluent 120 of reacting step 102 comprises AES and water.

[0032] Reacting step 102 is followed by water removal step 104, wherein water is removed from AES. Water removal step 104 may be performed using a spray dryer or thin film evaporator. Effluent 122 of water removal step 104 comprises AES.

[0033] After water removal step 104, effluent 122 comprising AES is then sent to a sulfonation step 106. Sulfonation step 106 comprises reacting AES with a sulfite, e.g., sodium sulfite (Na.sub.2SO.sub.3) and/or bisulfite to form taurine. Without being bound by theory, AES may also react with carbonate and/or bicarbonate to form one or more intermediates. Without being bound by theory, the one or more intermediates may react with the sulfite to form taurine. During sulfonation step 106, sodium sulfate (Na.sub.2SO.sub.4) may also be formed. Sulfonation step 106 may comprise using an upflow or downflow sulfonation reactor wherein effluent 122 comprising AES is continuously or semi-continuously pumped to the bottom or top of the sulfonation reactor. Similarly, a stream 124 comprising aqueous sulfite or bisulfite is continuously or semi-continuously pumped to the bottom or top of the sulfonation reactor. Similarly, stream 125 comprising a carbonate, e.g., soda ash, and/or a bicarbonate in water is continuously or semi-continuously pumped to the bottom or top of the sulfonation reactor. In the sulfonation reactor, AES is continuously or semi-continuously mixed and reacts with sulfite and/or bisulfite, and carbonate and/or bicarbonate present in the sulfonation reactor. The sulfonation reactor may be sealed with a pressure head with an inert gas 126 (e.g., nitrogen gas). Sulfonation step 106 comprises continuously or semi-continuously subjecting the mixture of AES, sulfite and/or bisulfite, and carbonate and/or bicarbonate to heat in the presence of the inert gas. The heat may be a predetermined reaction temperature. In an aspect, the mixture of AES, sulfite or bisulfite, and carbonate and/or bicarbonate is continuously subjected to a pressure greater than autogenous pressure. In an aspect, the pressure may be at least 200 psi inert gas (e.g., N.sub.2). In an aspect, the heat may be at least 115° C. In an embodiment, the heat may be at least 120° C. In a preferred embodiment, the heat may be 120-155° C. In a more preferred embodiment, the heat may be 140-155° C. Effluent 108 from sulfonation step 106 comprises taurine and may also comprise Na.sub.2SO.sub.4 and Na.sub.2SO.sub.3, as well as unreacted MEA and, AES. Effluent 108 from sulfonation step 106 may also include a trace or small amount of any unreacted intermediate formed by the reaction of AES and carbonate and/or bicarbonate, and which did not react with sulfite and/or bisulfite to form taurine.

[0034] Effluent 108 from sulfonation step 106 may then be conveyed to chromatography step 110. In chromatography step 110, Na.sub.2SO.sub.4 and Na.sub.2SO.sub.3 is separated from taurine in effluent 108.

[0035] Effluent 112 from chromatography step 110 comprises taurine and may be conveyed to crystallization step 114. In crystallization step 114, taurine in effluent 112 is crystallized. Crystallization step may comprise cooling effluent 112 from an elevated temperature, e.g., about 100° C., to a lower temperature, e.g., about 28° C. Crystallization step 114 may be preceded by a water removal step (not shown in FIG. 1) wherein water is removed from effluent 112, e.g., by distillation, thereby concentrating the amount of taurine in effluent 112 prior to crystallization.

[0036] Effluent 116 from crystallization step 114 comprises crystallized taurine and may be conveyed to filtration step 118. In filtration step 118, crystallized taurine is separated from unreacted MEA and AES. Unreacted MEA and AES may be recycled to reaction step 102 for synthesis of AES as previously described.

[0037] FIG. 2 depicts a drying apparatus 200 for water removal in accordance with aspects of the invention. Drying apparatus 200 comprises spray dryer 202. Drying apparatus 200 comprises drying gas 204. Drying gas 204 may be an inert gas, e.g., N.sub.2. Liquid feed 206 may be the same as effluent 120 shown in FIG. 1. Thus, liquid feed 206 comprises AES formed in reacting step 102 shown in FIG. 1.

[0038] Spray dryer 202 may comprise drying chamber 210 and an atomizer 208 configured to atomize liquid feed 206. Effluent 212 from spray dryer 202 may be conveyed to cyclone 214. In cyclone 214, exhaust gas 216 is separated from effluent 222. Effluent 222 exits cyclone 214 through opening 218. Effluent 222, comprising AES, may be collected in a collector 220. Effluent 222 may be the same as effluent 122 shown in FIG. 1. Thus, effluent 222 comprising AES has less water than liquid feed 206.

[0039] FIG. 3 depicts apparatus 300 for sulfonation step 106 shown in FIG. 1 in accordance with aspects of the invention. As shown in FIG. 3, apparatus 300 may comprise an upflow sulfonation reactor 302. Those skilled the art having the benefit of the present disclosure will recognize that the sulfonation reactor may be a downflow sulfonation reactor. Feed 304 in feed vessel 306 may be degassed by an inert gas prior to being conveyed out of feed vessel 306. The inert gas may be any suitable inert gas, including but not limited to nitrogen, helium, argon, and combinations thereof. In a preferred embodiment, the inert gas is nitrogen. Feed 304 is continuously conveyed out of feed vessel 306 by pump 308 to bottom 310 of upflow sulfonation reactor 302. Feed 304 may be the same as effluent 222 shown in FIG. 2. Thus, feed 304 comprises AES. As shown in FIG. 3, AES may be continuously pumped to the bottom of the sulfonation reactor 302. In sulfonation reactor 302, AES reacts with sulfite and/or bisulfite present in the sulfonation reactor 302 to form taurine.

[0040] Aqueous sulfite and/or bisulfite 322, e.g., aqueous sodium sulfite and/or aqueous sodium bisulfite, in vessel 324 may be degassed by an inert gas prior to being conveyed out of vessel 324. The inert gas may be any suitable inert gas, including but not limited to nitrogen, helium, argon, and combinations thereof. In a preferred embodiment, the inert gas is nitrogen. Aqueous sulfite and/or bisulfite 322 is continuously conveyed out of vessel 324 as stream 326 by pump 328 to bottom 310 of upflow sulfonation reactor 302. Stream 326 comprising aqueous sulfite and/or bisulfite 322 may be the same as stream 124 shown in FIG. 1.

[0041] Carbonate and/or bicarbonate 332 is continuously conveyed out of carbonate/bicarbonate vessel 334 by pump 336 to bottom 310 of upflow sulfonation reactor 302. Carbonate/bicarbonate 332 may be the same as stream 125 shown in FIG. 1.

[0042] Sulfonation reactor 302 may be sealed with a pressure head with an inert gas, e.g., inert gas 330. Inert gas 330 may be the same as inert gas 126 shown in FIG. 1. Thus, sulfonation step 106 shown in FIG. 1 may be performed in apparatus 300 shown in FIG. 3. Sulfonation reactor 302 may be operated by heating the reaction mixture of AES and aqueous sulfite and/or bisulfite at a reaction temperature and under a reaction pressure, e.g., a reaction pressure of at least 200 psi inert gas (e.g., N.sub.2). The reaction temperature may be at least 110° C. In an embodiment, the reaction temperature may be at least 120° C. In a preferred embodiment, the reaction temperature may be 120-155° C. In a more preferred embodiment, the reaction temperature may be 140-155° C. Via conduit 316, effluent 318 may be collected in vessel 320. Effluent 318 may be the same as effluent 108 shown in FIG. 1. Thus, effluent 318 comprises taurine, and may also comprise Na.sub.2SO.sub.4 and Na.sub.2SO.sub.3, as well as unreacted MEA and AES. Exhaust gas 312 comprising inert gas may exit sulfonation reactor 302 through conduit 314 as may be desired, e.g., to purge materials in sulfonation reactor, or maintain a predetermined pressure in the sulfonation reactor 302.

[0043] FIG. 4 depicts apparatus 400. Apparatus 400 is the same as apparatus 300 shown FIG. 3, with the exception that aqueous sulfite and/or bisulfite stream 326 is continuously conveyed by pump 328 to upper part 406 of upflow sulfonation reactor 302 through inlet 402, rather than to bottom 310 of upflow sulfonation reactor 302. Without being bound by theory, AES of feed 304 may react with carbonate and/or bicarbonate 332 to form one more intermediates in lower part 404 of upflow sulfonation reactor 302. As shown in FIG. 4, lower part 404 is below dashed line A-A and upper part 406 is above dashed line A-A. In upper part 406, aqueous sulfite and/or bisulfite of stream 326 reacts with materials from lower part 404 to form taurine, without production of undesirable taurine by-product.

[0044] Table 1 is a summary that shows the benefits of using a carbonate and/or bicarbonate in the production of taurine as disclosed in regard to aspects of the present disclosure as compared to traditional or conventional MEA methods that do not use carbonate and/or bicarbonate addition in production of taurine. In Table 1, undesirable taurine by-product includes N-2-Aminoethyl-2-aminoethanesulfonic acid.

TABLE-US-00001 TABLE 1 Process with Conventional carbonate and/or MEA bicarbonate process addition Taurine yield % 49-60% >75% Time, hours 40-60 <1 Undesirable taurine Yes No by-product Molar ratio, Equal or 1.2-1.3 sulfite/AES greater than 1.8 Inert gas (e.g., No Yes, 100 psi nitrogen), inert gas pressure pH Neutral 7.3-8.3 Product color Yellow Colorless Odor Strong sulfur Weak sulfur dioxide odor dioxide odor Reactor Batch Continuous or semi-continuous

[0045] Table 2 shows molar ratios and carbonate amount effect on taurine yield with sulfonation reactor conditions of 150° C., 1-hour reaction time, at 100 psi N.sub.2, with a 1.3 molar ratio of sodium bisulfite to AES. Sodium hydroxide was added in the molar ratios shown in Table 2 to raise the pH of the reaction mixture to the pH values shown in Table 2.

TABLE-US-00002 TABLE 2 carbonate amount effect on taurine yield Taurine AES yield Feed Carbonate:AES NaOH:SBS Conversion % (mol %) pH 0.4:1 0.49 100 71.8 7.1 0.6:1 0.72 100 76.7 7.7 0.7:1 0.77 100 81.5 7.9

[0046] The following examples further describe taurine synthesis in accordance with aspects of the present invention.

Example 1

[0047] A 5-gallon autoclave reactor was charged with 5.7 kg of 40% sodium bisulfite (NaHSO.sub.3), and 2.26 kg of AES in 7.5 kg of water, then 975 grams of NaOH was added to above mixture with stirring. To above mixture, 616 grams of soda ash was added to keep the solution pH at 8.1. The reactor was then sealed with a pressure head, purged three time with N.sub.2, then heated to 150° C. for 45 minutes (0.75 hours) with 200 psi N.sub.2. After this time, the reaction was quenched by flash cooling in an ice bath. Once the thermocouple temperature read 20° C., the pressure head was removed, and liquid transferred to a storage vessel. The product was analyzed by LC-MS. Results from these indicated that 100% AES conversion with 82% of taurine yield.

Example 2

[0048] To 20 ml of the product from Example 1 was added small amount (3 drops) of concentrated H.sub.2SO.sub.4, the product was analyzed with NMR .sup.1H and .sup.13C. There was no carbamate in the final product.

Example 3

[0049] General procedures for preparing samples are described below, and results are provided in Table 3 and discussed below.

[0050] In a typical reaction, 11.03 g 40 wt % sodium bisulfite (SBS) solution was added to a 75 mL Hastelloy Parr reactor. Various amounts of NaOH at different molar ratio compared to SBS (in the range of 0.5:1-1:1 of NaOH; SBS, 0.85-1.70 g NaOH) was dissolved in 20 g H.sub.2O, and then added to SBS solution. Various amounts of Na.sub.2CO.sub.3 at different molar ratio compared to AES (in the range of 0.1:1-0.8:1 of sodium carbonate (Na.sub.2CO.sub.3): AES, 0.36-2.82 g Na.sub.2CO.sub.3) was measured and added to the mixture. After all the Na.sub.2CO.sub.3 dissolved, 4.70 g AES was then added. The system was then heated at 60-65° C. to help accelerate the dissolving of AES. 70 mg of benzoic acid was added at last as internal standard. The initial pH value of the feed was recorded, and a feed sample was taken for analysis using .sup.1H NMR and .sup.13C NMR. The reactor was then sealed, purged for three times using N.sub.2, and charged with 200 psi N.sub.2 before reaction. The reactions were performed at stirring speed 1000 rpm, temperature 130 or 140° C. for two hours, or at 150° C. for one hour. After reaction, the reactor was cooled down to room temperature, and the product mixture analyzed by .sup.1H NMR and .sup.13C NMR.

TABLE-US-00003 TABLE 3 Total Taurine yield (molar) − (Free Taurine + 2-(Carboxy N-2- Sodium Sodium NaOH/ Free 2-(Carboxy amino) ethane Aminoethyl- sulfite/ bisulfite/ Carbonate/ Sodium Reac- MEA Taurine amino)ethane sulfonic acid, 2-aminoethane Sample AES AES AES bisulfite Temp. tion AES yield yield sulfonic acid converted sulfonic acid # (molar) (molar) (molar) (molar) (° C.) time (h) conv. (molar) (molar) yield (molar) to taurine) (molar)  1 1.3 0.1 1 130 2 93.5 8.6 76.1 4.1 80.2 **  2 1.2 0.1 1 130 2 93.3 9.5 76.4 2.7 79.1 **  3* 1.3 0 1 130 2 89.5 8.0 60.2 0 60.2 23  4 1.35 0.48 0.49 150 1 100.0 14.4 65.9 5.9 71.8 <1  5 1.36 0.55 0.56 150 1 100.0 13.7 60.5 11.1 71.6 <1  6 1.36 0.59 0.61 150 1 100.0 17.0 58.0 16.2 74.2 <1  7 1.36 0.58 0.72 150 1 100.0 17.1 57.1 18.4 75.5 <1  8 1.35 0.80 0.77 150 1 100.0 17.3 52.6 28.9 81.5 <1  9 1.36 0.88 0.77 150 1 100.0 17.7 50.7 29.4 80.1 <1 10 1.35 0.96 0.78 150 1 100.0 18.2 55.7 23.9 79.6 <1 11 1.22 0.81 0.71 150 1 100.0 18.3 45.4 28.1 73.5 <1 12 1.34 0.70 0.8 KOH 150 1 100.0 17.9 55.1 24.9 80.0 <1 13 1.22 0.81 0.71 150 1 100.0 20.7 47.3 28.1 75.4 <1 14* 1.29 0 0 0 150 1 100.0 11.0 64.2 0 64.2 ** 15 1.22 0.74 0.73 150 1 100.0 21.8 52.7 22.8 75.5 <1 16 1.36 0.47 0.94 150 1 100.0 21.4 59.1 18.2 77.3 <1 17 1.37 0.46 0.88 150 1 100.0 20.0 60.8 15.0 75.8 <1 18 1.11 0.43 0.70 150 1 100.0 22.7 57.7 12.1 69.8 <1 19 0.92 0.42 0.56 150 1 100.0 15.1 52.8 6.7 59.5 <1 20 1.31 0.10 1.01 130 2 93.5 8.6 76.1 4.1 80.2 5.92 21 1.31 0.10 1.00 130 2 93.3 9.5 76.4 2.7 79.1 5.04 22 1.32 0.10 1.01 130 2 95.5 10.8 73.6 3.3 76.9 5.96 23 1.32 0.10 0.90 130 2 89.4 9.0 71.4 3.1 74.5 5.68 24 1.32 0.10 0.81 130 2 86.1 9.3 66.3 3.7 70.0 4.93 25 1.22 0 0.22 0 130 2 97.3 10.7 75.1 5.2 80.3 3.77 26 1.32 0.11 0.80 140 2 94.4 10.8 72.4 1.0 73.4 6.85 27 1.31 0.11 0.92 140 2 98.1 13.1 76.9 1.7 78.6 6.86 28 1.21 0 0.22 0 140 2 100.0 11.6 69.9 7.3 77.2 7.99 29 1.32 0.11 1.05 140 2 100.0 10.0 ** 72.6 ** 30 1.31 0.11 0.96 140 2 100.0 10.0 ** 74.7 ** 31 1.32 0.11 0.95 150 1 100.0 10.0 ** 62.9 ** 32 1.32 0.11 1.01 130 2 100.0 11.6 ** 80.5 ** 33 1.31 0.11 0.79 140 2 97.1 11.7 65.3 2.4 67.7 ** 34 1.33 0.11 1.01 140 2 100.0 10.0 69.1 8.6 77.7 ** 35 1.32 0.11 1.02 150 1 100.0 13.0 65.0 9.8 74.8 ** 36 1.31 0.22 0.94 150 1 100.0 16.4 70.1 8.6 78.7 ** 37 1.32 0.23 1.04 150 1 96.2 16.3 68.4 8.4 76.8 ** 38 1.31 0.22 0.96 140 2 100.0 11.6 65.1 7.9 73.0 ** 39 1.32 0.23 1.04 140 2 100.0 12.6 72.0 8.2 80.2 ** 40 1.37 0.60 0.61 150 1 100.0 17.3 68.8 12.7 81.5 ** 41 1.37 0.60 0.66 150 1 100.0 16.4 63.8 16.5 80.3 ** 42 1.37 0.69 0.51 150 1 100.0 12.3 68.8 12.2 81.0 ** 43 1.36 0.64 0.57 150 1 100.0 18.2 71.4 10.6 82.0 ** *Control (no carbonate addition) ** Was not measured

[0051] As shown in Example 2, addition of an acid, e.g., concentrated sulfuric acid, to a mixture of taurine and carbamate will convert the carbamate to taurine. Those skilled in the art having the benefit of the present disclosure will recognize that a similar addition of acid, such as concentrated sulfuric acid to the mixture of taurine and carbamate in Example 3, i.e., Samples 1-2, 4-13, and 15-43 made with carbonate (here, sodium carbonate) in accordance with aspects of the present invention, will convert the carbamate to taurine, resulting in a higher total taurine yield than without the addition of the carbonate. As shown above, the control Samples 3 and 14 (with no carbonate) had a total taurine yield (molar) of 60.2 and 64.2, respectively. Samples 1-2, 4-13, and 15-43 made with carbonate in accordance with aspects of the present invention had higher total taurine yield (molar), with the exception of Sample 19. The total taurine yield of Sample 19 is due to the low molar ratio of sulfite/AES of 0.92% (sodium bisulfite/AES), whereas the control Samples 3 and 14 had higher molar ratio of sulfite/AES of 1.3% (sodium bisulfite/AES) and 1.29% (sodium sulfite/AES), respectively.

[0052] Moreover, Samples 4-13, and 15-28 all had a yield of undesirable taurine by-product, i.e., N-2-Aminoethyl-2-aminoethane sulfonic acid (molar), that were much lower than control Sample 3 that had a yield of 23% (molar) of the undesirable taurine by-product. Control Sample 14 was not measured for the undesirable taurine by-product. However, in view of the results of control Sample 3, it would be expected that control Sample 14 would have an undesirable taurine by-product similar to that of control Sample 3, and much higher than that of Samples 4-13, and 15-28.

[0053] As shown in Table 3, Samples 4-13 and 15-19 all had a yield of less than 1% of undesirable taurine by-product, i.e., N-2-Aminoethyl-2-aminoethane sulfonic acid (molar). As shown in Table 3, Samples 20-28 had undesirable taurine by-product, i.e., N-2-Aminoethyl-2-aminoethane sulfonic acid (molar) ranging from 3.77% (Sample 25) to 7.99% (Sample 28). Samples 1-2 and 29-43 were not measured for the undesirable taurine by-product. However, in view of the results of Samples 4-13, 15-19, and 20-28, it would be expected that Samples 1-2 and 29-43 would each have a similar low amount of undesirable taurine by-product as that of Samples 4-13, 15-19, and 20-28 as all these samples had carbonate addition.

[0054] Those skilled in the art having the benefit of the present disclosure will recognize that the above features disclosed herein improve upon conventional MEA processes by reducing the time of sulfonation in conventional MEA processes by a factor of at least four.

[0055] Those having skill in the art, with the knowledge gained from the present disclosure, will recognize that various changes can be made to the disclosed processes in attaining these and other advantages, without departing from the scope of the present disclosure. As such, it should be understood that the features of the disclosure are susceptible to modifications and/or substitutions. The specific embodiments illustrated and described herein are for illustrative purposes only, and not limiting of the invention as set forth in the appended claims.