CN105732440A - Method of fully recycling mother liquid to produce taurine - Google Patents
Method of fully recycling mother liquid to produce taurine Download PDFInfo
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- CN105732440A CN105732440A CN201610160908.8A CN201610160908A CN105732440A CN 105732440 A CN105732440 A CN 105732440A CN 201610160908 A CN201610160908 A CN 201610160908A CN 105732440 A CN105732440 A CN 105732440A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
Abstract
The invention discloses a method of fully recycling mother liquid to produce taurine.The method specifically includes: utilizing ethylene oxide and sodium hydrogen sulfite to prepare 2-hydroxy ethyl sodium sulfonate; preparing sodium taurate through high temperature high pressure and concentration; removing impurities through 2-stage neutralizing to obtain a taurine crude product; subjecting the mother liquid to press filtering and catalysis to further remove sodium sulfate, recycling to a synthesis section, combining with an ammonia solution of hydroxy ethyl sodium sulfonate, enabling a mixture to enter a synthesis tower for reaction, and controlling a proportion of hydroxy ethyl sodium sulfonate to the mother liquid to enable hydroxy ethyl sodium sulfonate which does not react completely in the mother liquid to react completely.Therefore, discharging pollution of the mother liquid is avoided completely, and total reaction yield is increased.
Description
Technical field
The present invention relates to a kind of method that full recovery mother solution produces taurine.
Background technology
Taurine chemical name 2 one taurine; being the sulfur-bearing free amino acid that content is the abundantest in body cell, it grows the brain of infant, nerve, internal organs, endocrine dysfunction etc. and calcareous, fatty and vitamin absorption all plays vital effect. and contribute to adult's health invigorating, prevention disease, relieving fatigue improve work efficiency.Extensively made an addition in numerous food, especially humanized milk powder as nutrition enhancer.
The laboratory synthetic method of taurine has more than ten to plant, but Industrialized synthesis method only has two kinds.I.e. it is esterified sulfonation method (Girbotal process) and sodium isethionate ammonolysis acidification method (epoxyethane method).Girbotal process labor intensity is big, it is difficult to continuous prodution, and energy consumption is high, and yield is only 50%, and production cost is high.Epoxyethane method avoids the reversible reaction affecting conversion ratio in Girbotal process, and therefore yield is higher, up to 80%, it is simple to continuous prodution.Its dominant response is:
CH2CH2O +
NaHSO3HOCH one by one2CH2SO3Na
HOCH2CH2SO3Na + NH3——H2NCH2CH2SO3Na
+ H2O
H2NCH2CH2SO3Na+1/2H2SO4——H2NCH2CH2SO3H+1/2
Na2SO4
Main side reaction includes addition side reaction and synthesizes side reaction:
Addition side reaction:
CH2CH2O + H2O
HOCH one by one2CH2OH
Ammonolysis side reaction:
2HOCH2CH2SO3Na + NH3——HN(CH2CH2SO3Na)2+2H2O
3HOCH2CH2SO3Na + NH3——N(CH2CH2SO3Na)3+3H2O
Although epoxyethane method yield is higher, but owing to addition and synthetic reaction inevitably producing by-product, when Recycling Mother Solution is applied mechanically, these by-products can cumulative rises in mother solution, production is caused to be normally carried out, have to for this emit partial mother liquid so that yield declines, and increases cost of sewage disposal simultaneously.
The present invention is directed to problem present in above-mentioned epoxyethane method, existing technique is made significant improvement so that mother solution fully recovering to synthesizing section, total recovery brings up to more than 90%, has stopped mother solution discharge simultaneously, solves waste liquor and discharges the environmental issue brought.
Summary of the invention
Present invention aim at providing a kind of method that mother solution fully recovering is produced taurine; the technique that have studied sodium isethionate ammonolysis acidification method (epoxyethane method) synthesizing taurine; epoxy additive reaction therein, high pressure ammonolysis course of reaction, synthesis feed liquid acidifying N-process, mother solution heating concentration process, and reuse mother solution removal of impurity processing procedure have been carried out process optimization.
The process that the present invention uses comprises the following steps:
(1). preferably technical scheme is that by setting metering and being equipped with the synthetic tower of sodium sulfite, ethylene oxide gas is carried out hybrid reaction, obtains hydroxyethylsulfonic acid. sodium solution, as the raw material of high pressure ammonolysis reaction after reaction；
(2). preferably technical scheme is also the hydroxyethylsulfonic acid. sodium solution prepared in (1) step and the reuse mother solution processed mixing; absorb ammonia and supplement ammonia or liquefied ammonia; pump into high-pressure synthesis tower through high-pressure plunger pump and carry out ammonolysis reaction, obtain sodium taurocholate solution.
(3). preferably technical scheme is the oxirane in (1) step and sodium sulfite sets metering than in molar ratio for 1.05:1.10 hybrid reaction, and it is 60 ~ 75 DEG C that its reaction temperature controls, and the pH value of reaction controls 5.7 ~ 6.3.
(4). preferably technical scheme is addition mother solution in (2) step; supplement ammonia, ammonia or liquefied ammonia; the weight percent content controlling ammonia or liquefied ammonia is 24 ~ 34%; wherein (1) and (2) step are all through high-temperature high-voltage reaction; material is not less than 0.5 ~ 1 hour at synthesis dwell time in the tower; after above-mentioned reaction, sodium isethionate ammonolysis becomes sodium taurocholate, and imino-diacetic ethyl sodium sulfonate and N-tri-ethyl sulfonic acid sodium in mother solution are also converted to sodium taurocholate；Overall reaction yield reaches 90% ~ 95%.
(5). preferably technical scheme is that the sodium taurocholate solution obtained after described High Temperature High Pressure synthetic reaction is added sulphuric acid; its solution is made to neutralize; first it is acidified to pH=9.0 ~ 10.0; cool the temperature to 55 ~ 65 DEG C; polyethers by-product alcohols, the imino-diacetic ethyl sulfonic acid of part excess is removed again with horizontal type screw settling centrifuge; with N-tri-ethyl sulfonic acid class by-product; continue to be neutralized to pH=6.0 ~ 8.0 by above-mentioned material supernatant feed liquid after 1 grade centrifugal again; it is centrifuged through 2 grades again and obtains taurine crude product, then material is prepared concentrating and desalinating.
(6). desalination after preferably technical scheme is also the heated concentration of crude product material after being centrifuged described 2 grades；Again the filter pressing after cooling of the material after desalination is obtained two hypotaurine crude products；Then the material after filter pressing is prepared the removal of impurity to process.
(7). preferably technical scheme is also above-mentioned material employing steam mechanical compression device to be carried out heating concentrate, and the energy of the steam produced after i.e. being heated by material is carried out heating and concentrates material.
(8). the material after preferably technical scheme is by above-mentioned filter pressing adds catalyst mix homogeneously.
(9). preferably technical scheme be used catalyst be following any one or a combination thereof: alkali metal hydroxide, alkali carbonate (containing acid carbonate), ferrum system/aluminum-based metal salt, NiO/CeO2, rare earth oxide.
(10). the material after preferably technical scheme is by above-mentioned filter pressing adds the sodium taurocholate feed liquid or the ammonia of 20 ~ 30% that volume ratio is 1 ~ 10% again; regulation pH value is to 8.5 ~ 10.0; obtain Matrii Sulfas Exsiccatus and mother solution through filter press again, the mother solution after filter pressing is all reclaimed and is used for synthesizing section.
Use the synthesis technique that the present invention is optimized; while it significantly reduces by-product generation; the most effectively eliminate the by-product in mother solution; prevent the by-product being unfavorable for taurine synthetic reaction accumulation in mother solution; make mother solution can substantially increase overall reaction yield, what is more important with fully recovering to synthesizing section; completely avoid waste liquor and discharge the problem of environmental pollution brought, it is achieved that the cleanly production of taurine.
Accompanying drawing explanation
Fig. 1 is the process flow diagram of the method for a kind of full recovery mother solution production taurine of the present invention.
Fig. 2 is the dissociation curve figure of the taurine of the method for a kind of full recovery mother solution production taurine of the present invention.
Detailed description of the invention
Describe the present invention in detail below by preferred embodiment, but selected embodiment is not as a limitation of the invention.Those with ordinary skill in the art, according to present disclosure, improvement nonessential to some done by the present invention and adjustment, still falls within protection scope of the present invention.
Oxirane is specifically passed through sodium sulfite solution, and reaction temperature is 60 ~ 75 DEG C, and oxirane is 1.05 ~ 1.10 with the mol ratio of sodium sulfite, and pH value in reaction is 5.7 ~ 6.3, and reaction generates sodium isethionate, and this additive reaction yield is more than 95%.
Being merged with the mother solution after process by sodium isethionate, supplement ammonia, ammonia or liquefied ammonia, control ammonia content is 24 ~ 34%(w/v), pump into synthetic tower, material is not less than 0.5 ~ 1 hour at dwell time in the tower.Sodium isethionate ammonolysis becomes sodium taurocholate；Meanwhile, the glycols by-product in hydroxyethylsulfonic acid. sodium solution is changed into polyethers by-product alcohols through high-temperature high-voltage reaction.
Taurine belongs to aminoacid; therefore there is amino acid whose general characteristic, in acid condition in cation, in the basic conditions in anion; isoelectric point, IP is 5.12; see accompanying drawing 2, according to the dissociation curve of taurine, control acidulated condition; at part acidic; when solution is still alkalescence, major part taurine still exists with the form of anion, now utilizes the difference of sedimentation coefficient, can optionally separate the polyethers by-product alcohols removed in material.
Described material uses steam mechanical compression device to carry out heating and concentrates, and the energy of the steam produced after i.e. being heated by material is carried out heating and concentrates material.
Mother solution after two hypotaurine crude products are extracted in filter pressing needs to process reuse more further.
Embodiment 1:
Oxirane is passed through sodium sulfite solution, and reaction temperature controls at 60 ~ 65 DEG C；The amount ratio of oxirane and sodium sulfite controls 1.06 ~ 1.08；Acid-base value pH value controls 5.8 ~ 6.2.The sodium isethionate yield reacting generation with this understanding is the highest, more than 99%, by-product is minimum simultaneously, and glycols by-product accounts for the weight ratio of gross product less than 0.45%(glycols by-product, in overall reaction product, hydroxyethylsulfonic acid. sodium content is (w/w) based on 50%).
Being merged with the mother solution after process by sodium isethionate, supplement ammonia, ammonia or liquefied ammonia, control ammonia content is 24 ~ 34%(w/v), pump into synthetic tower, material is not less than 0.5 ~ 1 hour at dwell time in the tower.Sodium isethionate ammonolysis becomes sodium taurocholate；Meanwhile, the glycols by-product in hydroxyethylsulfonic acid. sodium solution is changed into polyethers by-product alcohols through high-temperature high-voltage reaction.
Taurine belongs to aminoacid; therefore there is amino acid whose general characteristic, in acid condition in cation, in the basic conditions in anion; isoelectric point, IP is 5.12; see accompanying drawing 2, according to the dissociation curve of taurine, control acidulated condition; at part acidic; when solution is still alkalescence, major part taurine still exists with the form of anion, now utilizes the difference of sedimentation coefficient, can optionally separate the polyethers by-product alcohols removed in material.
Above-mentioned material uses steam mechanical recompression equipment to carry out heating and concentrates, and the energy of the steam produced after i.e. being heated by material is carried out heating and concentrates material.
Mother solution after two hypotaurine crude products are extracted in filter pressing needs to process reuse more further.
Embodiment 2
Oxirane is passed through sodium sulfite solution, and reaction temperature controls at 60 ~ 65 DEG C；The amount ratio of oxirane and sodium sulfite controls 1.06 ~ 1.08；Acid-base value pH value controls 5.8 ~ 6.2.The sodium isethionate yield reacting generation with this understanding is the highest, more than 99%, by-product is minimum simultaneously, and glycols by-product accounts for the weight ratio of gross product less than 0.45%(glycols by-product, in overall reaction product, hydroxyethylsulfonic acid. sodium content is (w/w) based on 50%).
Being merged with the mother solution after process by sodium isethionate, supplement ammonia, ammonia or liquefied ammonia, control ammonia content is 24 ~ 34%(w/v), pump into synthetic tower, reaction temperature controls at 255 ~ 265 DEG C, and pressure is maintained at 19 ~ 20MPa, and the time of staying is not less than 0.5 ~ 1 hour.Sodium isethionate ammonolysis becomes sodium taurocholate；Meanwhile, the glycols by-product in hydroxyethylsulfonic acid. sodium solution is changed into polyethers by-product alcohols through high-temperature high-voltage reaction.
Taurine belongs to aminoacid; therefore there is amino acid whose general characteristic, in acid condition in cation, in the basic conditions in anion; isoelectric point, IP is 5.12; see accompanying drawing 2, according to the dissociation curve of taurine, control acidulated condition; at part acidic; when solution is still alkalescence, major part taurine still exists with the form of anion, now utilizes the difference of sedimentation coefficient, can optionally separate the polyethers by-product alcohols removed in material.
Above-mentioned material uses steam mechanical recompression equipment to carry out heating and concentrates, and the energy of the steam produced after i.e. being heated by material is carried out heating and concentrates material.
Mother solution after two hypotaurine crude products are extracted in filter pressing needs to process reuse more further.
Embodiment 3
Oxirane is passed through sodium sulfite solution, and reaction temperature controls at 60 ~ 65 DEG C；The amount ratio of oxirane and sodium sulfite controls 1.06 ~ 1.08；Acid-base value pH value controls 5.8 ~ 6.2.The sodium isethionate yield reacting generation with this understanding is the highest, more than 99%, by-product is minimum simultaneously, and glycols by-product accounts for the weight ratio of gross product less than 0.45%(glycols by-product, in overall reaction product, hydroxyethylsulfonic acid. sodium content is (w/w) based on 50%).
Being merged with the mother solution after process by sodium isethionate, supplement ammonia, ammonia or liquefied ammonia, control ammonia content is 24 ~ 34%(w/v), pump into synthetic tower, reaction temperature controls at 255 ~ 265 DEG C, and pressure is maintained at 19 ~ 20MPa, and the time of staying is not less than 0.5 ~ 1 hour.Sodium isethionate ammonolysis becomes sodium taurocholate；Meanwhile, the glycols by-product in hydroxyethylsulfonic acid. sodium solution is changed into polyethers by-product alcohols through high-temperature high-voltage reaction.
Taurine belongs to aminoacid; therefore there is amino acid whose general characteristic, in acid condition in cation, in the basic conditions in anion; isoelectric point, IP is 5.12; see accompanying drawing 2, according to the dissociation curve of taurine, control acidulated condition; at part acidic; when solution is still alkalescence, major part taurine still exists with the form of anion, now utilizes the difference of sedimentation coefficient, can optionally separate the polyethers by-product alcohols removed in material.
Sulphuric acid is added in sodium taurocholate solution; keep acidity-basicity ph=9.5; control temperature at 55 ~ 65 DEG C; through horizontal type screw settling centrifugal segregation by-product; supernatant continues to neutralize acidity-basicity ph=7.0 ~ 8.0, sees accompanying drawing 2, and now taurine major part exists with non-ionic free weak acid form; product crystallization from feed liquid, centrifuged taurine crude product and material is conducive to prepare concentrating and desalinating.
Above-mentioned material uses steam mechanical compression device to carry out heating and concentrates, and the energy of the steam produced after i.e. being heated by material is carried out heating and concentrates material.
Mother solution after two hypotaurine crude products are extracted in filter pressing needs to process reuse more further.
Embodiment 4
Oxirane is passed through sodium sulfite solution, and reaction temperature controls at 60 ~ 65 DEG C；The amount ratio of oxirane and sodium sulfite controls 1.06 ~ 1.08；Acid-base value pH value controls 5.8 ~ 6.2.The sodium isethionate yield reacting generation with this understanding is the highest, more than 99%, by-product is minimum simultaneously, and glycols by-product accounts for the weight ratio of gross product less than 0.45%(glycols by-product, in overall reaction product, hydroxyethylsulfonic acid. sodium content is (w/w) based on 50%).
By sodium isethionate with process after mother solution merge, add a certain amount of catalyst, and 5 ~ 10%(v/v) sodium taurocholate solution, the mainly content of taurine controls 40 ~ 45%；And the amount of ammonia controls 20 ~ 30%；Regulation controls acidity-basicity ph=9.7 ~ 9.8, pumps into synthetic tower, and reaction temperature controls at 255 ~ 265 DEG C, and pressure is maintained at 19 ~ 20MPa, and the time of staying is not less than 0.5 ~ 1 hour.Sodium isethionate ammonolysis becomes sodium taurocholate；Meanwhile, the glycols by-product in hydroxyethylsulfonic acid. sodium solution is changed into polyethers by-product alcohols through high-temperature high-voltage reaction.
Taurine belongs to aminoacid; therefore there is amino acid whose general characteristic, in acid condition in cation, in the basic conditions in anion; isoelectric point, IP is 5.12; see accompanying drawing 2, according to the dissociation curve of taurine, control acidulated condition; at part acidic; when solution is still alkalescence, major part taurine still exists with the form of anion, now utilizes the difference of sedimentation coefficient, can optionally separate the polyethers by-product alcohols removed in material.
Sulphuric acid is added in sodium taurocholate solution; keep acidity-basicity ph=9.5; control temperature at 55 ~ 65 DEG C; through horizontal type screw settling centrifugal segregation by-product, supernatant continues to neutralize acidity-basicity ph=7.0 ~ 8.0, sees accompanying drawing 2; now taurine major part exists with non-ionic free weak acid form; being conducive to product crystallization from feed liquid, centrifuged taurine crude product, mother solution prepares concentrating and desalinating.
Utilize steam mechanical compress technique (MVR), mother solution is concentrated.Mother liquor temperature controls at 90 ~ 100 DEG C, and indirect steam temperature controls at 130 ~ 140 DEG C, continuous feed and discharging.The vapo(u)rous pressure produced after making full use of mother solution heating, it is achieved masterbatch is carried out heating and concentrates; substantially increase the thermal efficiency; significantly reduce energy consumption, and make heating process milder, follow-up centrifugal desalination (sodium sulfate) and the filter pressing of two hypotaurine crude products from mother solution.
Mother solution fully recovering after two hypotaurine crude products are extracted in filter pressing.
Claims (9)
1. the method that mother solution fully recovering is produced taurine, it is characterised in that described method comprises the steps:
S1, ethylene oxide gas is carried out hybrid reaction by setting in metering is equipped with the synthetic tower of sodium sulfite, obtain hydroxyethylsulfonic acid. sodium solution in reaction, as the raw material of high pressure ammonolysis reaction；
S2, the hydroxyethylsulfonic acid. sodium solution prepared in S1 step and the reuse mother solution mixing processed, absorb ammonia and supplement ammonia or liquefied ammonia, pumping into high-pressure synthesis tower through high-pressure plunger pump and carry out ammonolysis reaction, obtain sodium taurocholate solution；
S3, synthesizing prepared sodium taurocholate solution add sulphuric acid and neutralize in S2 step, be first acidified to pH=9.5, after horizontal type screw settling centrifugal treating, supernatant continues to be acidified to pH=6.0 ~ 8.0, centrifugal obtains taurine crude product and mother solution；
S4, the mother solution obtained in S3 step carry out heating through steam mechanical recompression (MVR) and concentrate, and high temperature centrifugal segregation sodium sulfate, the filter pressing after cooling of the mother solution after desalination obtains two hypotaurine crude products；
S5, in S4 step mother solution after filter pressing be initially charged 1 ~ 10%(volume ratio) sodium taurocholate solution or the ammonia of 20 ~ 30%, then after filter press removes Matrii Sulfas Exsiccatus fully recovering to synthesizing section (step S2).
Method the most according to claim 1, it is characterised in that: oxirane and sodium sulfite setting metering in described S1 step are 1.05:1.10 hybrid reaction than in molar ratio, and it is 60 ~ 75 DEG C that its reaction temperature controls, and it is 5.7 ~ 6.3 that the pH value of reaction controls.
Method the most according to claim 1; it is characterized in that: described S2 step adds mother solution; supplement ammonia, ammonia or liquefied ammonia; the weight percent content controlling ammonia or liquefied ammonia is 24 ~ 34%; wherein S1 Yu S2 step is all through high-temperature high-voltage reaction; material is at synthesis dwell time in the tower not less than 0.5 ~ 1 hour, and after above-mentioned reaction, sodium isethionate ammonolysis becomes sodium taurocholate, and imino-diacetic ethyl sodium sulfonate and N-tri-ethyl sulfonic acid sodium in mother solution are also converted to sodium taurocholate；Overall reaction yield reaches 90% ~ 95%.
Method the most according to claim 3; it is characterized in that: the sodium taurocholate solution obtained after described High Temperature High Pressure synthetic reaction is added sulphuric acid; its solution is made to neutralize; first it is acidified to pH=9.0 ~ 10.0; cool the temperature to 55 ~ 65 DEG C; polyethers by-product alcohols, the imino-diacetic ethyl sulfonic acid of part excess is removed again with horizontal type screw settling centrifuge; with N-tri-ethyl sulfonic acid class by-product; supernatant feed liquid after being centrifuged above-mentioned 1 grade again continues to be neutralized to pH=6.0 ~ 8.0; it is centrifuged through 2 grades again and obtains taurine crude product, then mother solution is prepared concentrating and desalinating.
Method the most according to claim 4, it is characterised in that: desalination after the heated concentration of mother solution after described 2 grades are centrifuged；Again the filter pressing after cooling of the mother solution after desalination is obtained two hypotaurine crude products；Then the mother solution after filter pressing is prepared the removal of impurity to process.
Method the most according to claim 5, it is characterised in that: described mother solution uses steam mechanical compression device to carry out heating and concentrates, and the energy of the steam produced after i.e. being heated by mother solution is carried out heating and concentrates mother solution.
Method the most according to claim 5, it is characterised in that: the mother solution after described filter pressing is added catalyst mix homogeneously.
Method the most according to claim 7, it is characterised in that: used catalyst is following any one or a combination thereof: alkali metal hydroxide, alkali carbonate (containing acid carbonate), ferrum system/aluminum-based metal salt, NiO/CeO2, rare earth oxide.
Method the most according to claim 7; it is characterized in that: the mother solution after described filter pressing is added again sodium taurocholate feed liquid and the ammonia of 20 ~ 30% that volume ratio is 1 ~ 10%; regulation pH concentration is to 8.5 ~ 10.0; obtain Matrii Sulfas Exsiccatus through filter press again, the mother solution after filter pressing is all reclaimed and is used for synthesizing section.
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