Process for producing taurine

Abstract

There is disclosed a process for producing taurine by the ammonolysis of alkali isethionate in the presence of alkali ditaurinate or alkali tritaurinate, or their mixture, to inhibit the formation of byproducts and to continuously convert the byproducts of the ammonolysis reaction to alkali taurinate. The production yield is increased to from 90% to nearly quantitative. The ammonolysis reaction is catalyzed by alkali salts of hydroxide, sulfate, sulfite, phosphate, or carbonate.

Claims

.[.1. A process for producing taurine from alkali isethionate, comprising: (a) mixing alkali isethionate with a solution of alkali ditaurinate, alkali tritaurinate, or their mixture in the presence of one or more catalysts; (b) adding an excess of ammonia to the (a) and subjecting the solution to ammonolysis reaction to yield a mixture of alkali taurinate, alkali ditaurinate, and alkali tritaurinate; (c) removing excess ammonia and neutralizing with an acid to obtain a crystalline suspension of taurine; and (d) separating taurine by means of solid-liquid separation..].

.[.2. The process according to claim 1, wherein alkali taurinate and alkali tritaurinate are produced from diethanolamine and triethanolamine, respectively..].

.[.3. The process according to claim 1, wherein a mixture of alkali ditaurinate and alkali tritaurinate is the byproduct of the ammonolysis reaction of alkali isethionate..].

.[.4. The process according to claim 1, wherein an acid is selected from hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and organic carboxylic acids..].

.[.5. The process according to claim 1, wherein the mother liquor after separating taurine and alkali salt is continuously recycled and mixed with a new batch of alkali isethionate for the ammonolysis reaction..].

.[.6. The process according to claim 1, one or a combination of two or more catalysts for the ammonolysis reaction is selected from alkali salts of hydroxide, carbonate, sulfate, sulfite, phosphate, and nitrate..].

.[.7. The process according to claim 1, wherein the production yield of taurine is greater than 95%, to nearly quantitative..].

.[.8. The process according to claim 1, wherein the alkali metals are lithium, sodium, or potassium..].

.[.9. The process according to claim 1, wherein the production yield of taurine is greater than 85%..].

.[.10. The process according to claim 1, wherein the production yield of taurine is greater than 90%..].

.Iadd.11. A process for producing taurine from alkali isethionate in an overall molar yield of at least 85% on the basis of alkali isethionate, comprising: (a) mixing alkali isethionate with a solution comprised of alkali ditaurinate, or with a solution comprised of alkali tritaurinate, or with a solution comprised of alkali ditaurinate and alkali tritaurinate, in the presence of at least one catalyst, and adding an alkali hydroxide to the solution wherein the molar amount of the alkali hydroxide is at least equal to the molar amount of total taurinates in the solution; (b) adding excess ammonia to the solution of step (a) and subjecting the solution to ammonolysis to yield a mixture of alkali taurinate, alkali ditaurinate and alkali tritaurinate; (c) removing excess ammonia and neutralizing the mixture of step (b) with an acid to obtain a crystalline suspension of taurine; (d) recovering taurine by means of solid-liquid separation to obtain a mother liquor solution comprised of alkali ditaurinate and alkali tritaurinate; and (e) returning the mother liquor solution of step (d) to step (a) and performing steps (a), (b), (c), and (d)..Iaddend.

.Iadd.12. The process according to claim 11, wherein for step (a) the solution comprised of the alkali ditaurinate and the solution comprised of the alkali tritaurinate are produced from diethanolamine and triethanolamine, respectively..Iaddend.

.Iadd.13. The process according to claim 11, wherein the solution comprised of the alkali ditaurinate and alkali tritaurinate for step (a) is produced from alkali isethionate by a process comprising the steps of: (1) adding excess ammonia and optionally a catalyst to a solution comprised of alkali isethionate and subjecting the solution to ammonolysis; (2) removing excess ammonia from the solution of step (1) and neutralizing the solution with an acid to form a crystalline taurine suspension; and (3) recovering taurine to obtain a solution comprised of alkali ditaurinate and alkali tritaurinate..Iaddend.

.Iadd.14. The process according to claim 11, wherein the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and organic carboxylic acids..Iaddend.

.Iadd.15. The process according to claim 11, wherein the catalyst is selected from the group consisting of alkali salts of hydroxide, carbonate, sulfate, sulfite, phosphate, and nitrate..Iaddend.

.Iadd.16. The process according to claim 11, wherein the alkali is lithium, sodium, or potassium..Iaddend.

.Iadd.17. The process according to claim 11, wherein the overall molar production yield of taurine from the alkali isethionate is greater than 85%..Iaddend.

.Iadd.18. The process according to claim 11, wherein the overall molar production yield of taurine from the alkali isethionate is greater than 90%..Iaddend.

.Iadd.19. The process according to claim 11, wherein the overall molar production yield of taurine from the alkali isethionate is greater than 95%, to nearly quantitative..Iaddend.

Description

DESCRIPTION OF THE INVENTION

(1) The present invention relates to a process for the production of taurine by the ammonolysis reaction of alkali isethionate in the presence of alkali ditaurinate or alkali tritaurinate, or their mixture, to inhibit the formation of byproducts, to increase the production yield, and to greatly reduce the waste discharge from the production process.

(2) The process according to the present invention starts with mixing a solution of alkali ditaurinate or alkali tritaurinate, or their mixture, with alkali isethionate, followed by addition of an excess of ammonia. The ammonolysis is carried out at a temperature from 160 C. to 260 C. under the pressure from autogenous to 260 bars for 1 to 6 hours.

(3) After the ammonolysis reaction, excess ammonia is dispelled from the reaction solution and reclaimed for reuse. A solution of alkali taurinate is obtained, along with alkali ditaurinate, alkali tritaurinate, and a trace amount of unreacted alkali isethionate.

(4) The strongly basic solution is neutralized with an acid to pH 5-9 to yield a crystalline suspension of taurine in a solution of alkali salt, alkali ditaurinate, alkali tritaurinate, and a small amount of unreacted alkali isethionate. The initial suspension is optionally concentrated, then cooled to 28 to 35 C., to crystallize taurine. Taurine is obtained by means of solid-liquid separation.

(5) The ratio of alkali ditaurinate, alkali tritaurinate, or their mixture, in relation to alkali isethionate can be varied from 0.01 to 10 by weight, preferably 0.1 to 1, more preferably 0.2-0.5, most preferably 0.3-0.4.

(6) When the ratio is low, i.e., <0.1, a large amount of alkali isethionate is converted to alkali ditaurinate, instead of desired alkali taurinate, thus lowering the production yield and efficiency. When the ratio is too large, i.e., >1.0, the amount of the recycling byproducts becomes excessively large and the production capacity is lowered. Moreover, the cyclic process is not steady as the byproduct is indeed converted alkali taurinate.

(7) Useful and effective catalysts are found among the alkali salts of hydroxide, carbonate, bicarbonate, hydrogen sulfate, sulfate, bisulfite, sulfite, nitrate, phosphate, chlorate, and perchlorate. Such salts are sodium hydroxide, lithium hydroxide, potassium hydroxide, lithium carbonate, lithium bicarbonate, sodium bicarbonate, sodium bicarbonate, potassium bicarbonate, lithium carbonate, sodium carbonate, potassium carbonate, lithium sulfate, sodium sulfate, potassium sulfate, lithium phosphate, sodium phosphate, potassium phosphate, lithium sulfite, sodium sulfite, and potassium sulfite.

(8) The catalyst for the ammonolysis reaction of alkali isethionate can be one component or a combination of two or more components. Catalysts exogenous to the reaction system can be used, but catalysts inherently present in the production process are preferred. When sulfuric acid is used as a neutralizing acid, alkali salts of sulfate are preferred. Alkali salts of sulfite are preferred in the sulfur dioxide process.

(9) Preferable catalysts are alkali hydroxide and the most preferable catalyst is sodium hydroxide.

(10) The amount of the catalyst used is not limited, but is usually from 0.01 to 10 in molar ratio of the catalyst to alkali isethionate. The ratio is preferably in the range of 0.01 to 1, more preferably 0.1 to 0.5, most preferably 0.2 to 0.3. A suitable amount of catalyst can be selected by those skilled in the art for the ammonolysis reaction to complete in desired time.

(11) The acid used in the neutralization process is selected from hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and organic carboxylic acids containing one to six carbons. Sulfuric acid is most preferably used.

(12) Tables I to III demonstrate the effectiveness of the presence of alkali ditaurinate or alkali tritaurinate, or their mixture, on the ammonolysis of alkali isethionate to alkali taurinate, respectively. It becomes apparent that the conversion of alkali isethionate to alkali taurinate can reach nearly quantitative yield under disclosed conditions.

(13) Table IV shows the effect of a different catalyst on the ammonolysis of alkali isethionate to alkali taurinate. When no catalyst is added to the ammonolysis reaction, low conversion of alkali isethionate is observed.

(14) The process according to the present invention can be carried out discontinuously, semi-continuously, and continuously.

EXAMPLES

(15) The following examples illustrate the practice of this invention but are not intended to limit its scope.

Example 1

(16) This set of examples relates to the ammonolysis of sodium isethionate in the presence of sodium ditaurinate and in the presence of sodium hydroxide.

(17) All examples are for 0.05 mole of sodium isethionate, dissolved in 35 mL of 20% aqueous ammonia solution in a molar ratio of 1:8 for sodium isethionate to ammonia. Calculated amount of sodium ditaurinate and sodium hydroxide is then added to the solution. The ammonolysis reaction is carried out in an 100 mL autoclave at 220 C. under autogenous pressure for two hours. The content of taurine, ditaurine, and tritaurine is assayed by HPLC analysis. The yields are calculated according to the following formula:
Taurinate Yield (%)=[Taurine]/[Sodium Isethionate]
Di+Tritaurinate Yield (%)=[Di+TritaurineAdded Ditaurine]/[Sodium Isethionate]

(18) TABLE-US-00001 TABLE I Ammonolysis of Sodium Isethionate in the Presence of Sodium Ditaurinate Ditaurinate/ NaOH/ Di + Isethionate Isethionate Taurinate Tritaurinate (ratio by (ratio by (molar (molar Ex weight) weight) yield %) yield %) 1 0 0.01 75 24 2 0.1 0.01 84 15 3 0.2 0.01 86 14 4 0.3 0.01 87 13 5 0.3 0.02 91 9 6 0.3 0.03 93 7 7 0.3 0.04 95 5 8 0.3 0.05 98 2 9 0.5 0.15 112 12 10 1.0 0.20 145 45

Example 2

(19) This set of examples relates to the ammonolysis of sodium isethionate in the presence of sodium tritaurinate and in the presence of sodium hydroxide.

(20) All examples are for 0.05 mole of sodium isethionate, dissolved in 35 mL of 20% aqueous ammonia solution in a molar ratio of 1:8 for sodium isethionate to ammonia. Calculated amount of sodium tritaurinate and sodium hydroxide is then added to the solution. The ammonolysis reaction is carried out in an 100 mL autoclave at 220 C. under autogenous pressure for two hours. The content of taurine, ditaurine, and tritaurine is assayed by HPLC analysis. The yields are calculated according to the following formula:
Taurinate Yield (%)=[Taurine]/[Sodium Isethionate]
Di+Tritaurinate Yield (%)=[Di+TritaurineAdded Tritaurine]/[Sodium Isethionate]

(21) TABLE-US-00002 TABLE II Ammonolysis of Sodium Isethionate in the Presence of Sodium Tritaurinate Tritaurinate/ NaOH/ Di + Isethionate Isethionate Taurinate Tritaurinate (ratio by (ratio by (molar (molar Ex weight) weight) yield %) yield %) 11 0 0.01 76 24 12 0.1 0.01 83 16 13 0.2 0.01 86 14 14 0.3 0.01 87 13 15 0.3 0.02 88 11 16 0.3 0.03 94 6 17 0.3 0.04 94 5 18 0.3 0.05 98 2 19 0.5 0.15 121 20 20 1.0 0.20 151 49

Example 3

(22) This set of examples relates to the ammonolysis of sodium isethionate in the presence of a mixture of sodium ditaurinate and sodium tritaurinate obtained from the mother liquor of taurine crystallization and in the presence of sodium hydroxide and sodium sulfate.

(23) All examples are for 0.05 mole of sodium isethionate, dissolved in 35 mL of 20% aqueous ammonia solution in a molar ratio of 1:8 for sodium isethionate to ammonia. Calculated amount sodium hydroxide is then added to the solution. A mixture of sodium ditaurinate and sodium tritaurinate, obtained from the crystallization mother liquor described as in application Ser. No. 14/120,046 is used. The ammonolysis reaction is carried out in an 100 mL autoclave at 220 C. under autogenous pressure for two hours. The content of taurine, ditaurine, and tritaurine is assayed by HPLC analysis. The yields are calculated according to the following formula:
Taurinate Yield (%)=[Taurine]/[Sodium Isethionate]
Di+Tritaurinate Yield (%)=[Di+Tritaurine(Added Di+Tritaurine)]/[Sodium Isethionate]

(24) TABLE-US-00003 TABLE III Ammonolysis of Sodium Isethionate in the Presence of a Mixture of Sodium Ditaurinate and Sodium Tritaurinate (Di + Tritaurinate)/ NaOH/ Di + Isethionate Isethionate Taurinate Tritaurinate (ratio by (ratio by (molar (molar Ex weight) weight) yield %) yield %) 21 0 0.01 81 19 22 0.1 0.01 84 16 23 0.2 0.01 87 12 24 0.3 0.01 87 13 25 0.3 0.02 88 11 26 0.3 0.03 95 4 27 0.3 0.04 96 4 28 0.3 0.05 98 2 29 0.5 0.15 126 26 30 1.0 0.20 154 53

Example 4

(25) This set of examples shows the effect of a different catalyst on the ammonolysis of sodium isethionate in the presence of a mixture of sodium ditaurinate and sodium tritaurinate obtained from the mother liquor of taurine crystallization.

(26) All examples are for 0.05 mole of sodium isethionate, dissolved in 35 mL of 20% aqueous ammonia solution in a molar ratio of 1:8 for sodium isethionate to ammonia. Calculated amount catalyst and a mixture of sodium ditaurinate and sodium tritaurinate, obtained from the crystallization mother liquor described as in application Ser. No. 14/120,046, are added to the solution. The ratio of (di+tritaurinate)/isethionate by weight is fixed at 0.3. The ammonolysis reaction is carried out in an 100 mL autoclave at 220 C. under autogenous pressure for two hours. The content of taurine, ditaurine, and tritaurine is assayed by HPLC analysis. The yields are calculated according to the following formula:
Taurinate Yield (%)=[Taurine]/[Sodium Isethionate]
Di+Tritaurinate Yield (%)=[Di+Tritaurine(Added Di+Tritaurine)]/[Sodium Isethionate]

(27) TABLE-US-00004 TABLE IV Effect of Catalyst on Ammonolysis of Sodium Isethionate in the Presence of a Mixture of Sodium Ditaurinate and Sodium Tritaurinate Catalyst/ Di + Isethionate Taurinate Tritaurinate (ratio by (molar (molar Ex Catalyst weight) yield %) yield %) 31 None 0 55 12 32 Sodium carbonate 0.15 96 4 33 Sodium sulfite 0.15 95 4 34 Potassium hydroxide 0.10 97 3 35 Potassium carbonate 0.15 94 6 36 Potassium sulfite 0.10 94 6 37 Lithium hydroxide 0.03 95 4 38 Lithium carbonate 0.10 93 7 39 Sodium phosphate 0.15 97 3 40 Potassium phosphate 0.15 96 4 41 Potassium acetate 0.20 96 4 42 Sodium acetate 0.20 96 4

(28) It will be understood that the foregoing examples and explanation are for illustrative purposes only and that various modifications of the present invention will be self-evident to those skilled in the art. Such modifications are to be included within the spirit and purview of this application and the scope of the appended claims.