CN104744279B - Remove the method for impurity in glycine crystallization mother liquid - Google Patents
Remove the method for impurity in glycine crystallization mother liquid Download PDFInfo
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- CN104744279B CN104744279B CN201510159692.9A CN201510159692A CN104744279B CN 104744279 B CN104744279 B CN 104744279B CN 201510159692 A CN201510159692 A CN 201510159692A CN 104744279 B CN104744279 B CN 104744279B
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Abstract
The invention discloses the method for impurity in glycine crystallization mother liquid of removing, specifically by glycin mother liquid and ammonia or ammoniacal liquor temperature be 80 DEG C～180 DEG C, pressure be reaction 30min～180min under 0.3MPa～5.5MPa；Impurity can be converted into glycine by the method utilizing the present invention, impurity is avoided to accumulate in glycin mother liquid system, ammonia can be with recycled, do not consume any soda acid, environmental protection, the intermittently or serially metaplasia being capable of glycine is produced, and has good environmental benefit and economic benefit, and market prospects are good.
Description
Technical field
The invention belongs to chemical field, be specifically related to remove the method for impurity in glycine crystallization mother liquid.
Background technology
Chongqing Unisplendour Chemical Co., Ltd, through the hydroxyacetonitrile method production technology of further investigation glycine for many years, opens respectively
Send out and be the direct ammonification of raw material with hydroxyacetonitrile, alkaline hydrolysis, deamination, be acidified, decolour, concentrate and the operation such as purifying prepares glycine
Strecker method and with hydroxyacetonitrile and carbon dioxide, ammonia, water be the direct HTHP of raw material, deamination and carbon dioxide, de-
Look, concentrate and the operation such as purifying prepares the direct glycolylurea method of glycine.
Strecker method is prepared in glycine, and in follow-up glycine purge process, especially glycine recrystallization, due to temperature
Degree, the control improper formation peptides of time, amide-type organic compound (Fig. 1), and glycine recrystallization mother liquor are circulating sleeve
With, go the only decolouring of deimpurity workshop section, so peptides, amide-type organic compound are all difficult to be removed, thus cause above
Impurity is constantly enriched with in glycine recrystallization.Therefore, after glycine recrystallization Recycling Mother Solution applies mechanically a period of time, reaction is produced
In system, glycin mother liquid viscosity increases, and glycine crystallization and separation difficulty, the glycine quality obtained will decline, and even leads
Cause production can not be normally carried out.Therefore, part extraction or periodically place's glycin mother liquid are to ensure that mother liquor impurity is in lower content,
Ensure to produce the key being normally carried out and producing serialization.
Directly glycolylurea method is prepared in glycine, in glycine synthesis and crystallization process, due to hydroxyacetonitrile and carbon ammonium effect elder generation shape
Becoming hydantoins (abbreviation glycolylurea), glycolylurea becomes glycine through pyrohydrolysis, but at the glycine solution through de-carbon ammonium
In, not only contain glycine, but also containing following impurity glycine amide, dipeptides and polypeptide, glycolylurea, hydantoic acid, glycolylurea
Acid acid amides, 2, the organic compound (Fig. 2) such as 5-diketopiperazine, methylene amion acetic acid, and these compounds can be at strong alkaline condition
Under be converted into glycinate, thus avoid accumulative in glycin mother liquid of these impurity, thus affect the quality of glycine with
And the recycled number of times of glycin mother liquid.Therefore, part extraction or regular place glycin mother liquid are to ensure that mother liquor impurity is in relatively
Low content, it is ensured that produce the key being normally carried out and producing serialization.And acid amides, peptide are not only in the impurity in glycin mother liquid
Only can be formed, at glycine condensing crystallizing or recrystallization, owing to temperature is too high, mother liquid recycle during glycine synthesizes
Number of times is too many, and carboxyl, amino are all the active function groups easily reacting and being condensed, easily formed the amide compound of glycine with
And glycine dipeptidase, glycine tripeptide and 2, the compound such as 5-diketopiperazine, if not taking timely alkaline hydrolysis reduce or remove these
Impurity, the concentration of long-time high temperature or repeatedly recycled, the quality of glycine will be affected.
For the problems referred to above, therefore it is badly in need of effectively reducing the content of impurity in glycin mother liquid, improves the quality of crystalline mother solution, fall
Low production cost, reduces material consumption energy consumption, it is achieved cleaning produces, and improves yield and the quality of product.
Summary of the invention
In view of this, it is an object of the invention to provide the method for impurity, simple to operate, cost in removal glycine crystallization mother liquid
Cheap, do not consume any soda acid, organic impurities can be converted into glycine, without brine waste discharge, ammonia can with recycled,
Environmental protection.
For achieving the above object, it has been investigated that glycin mother liquid adds ammonia or ammoniacal liquor and heats, it is possible to effectively reduce
The content of the impurity in glycin mother liquid, and the content of glycine increased, and by glycin mother liquid and excess of ammonia or
Person's ammoniacal liquor carry out under conditions of HTHP interval or continuous prodution, can be the completeest by the impurity in glycin mother liquid
Entirely it is converted into glycine, the yield increasing glycine and the number of times of the recycled increasing glycin mother liquid, it is substantially reduced glycine
Mother liquor discharge, thus reduce the loss late of glycine, and after hydrolysis, ammonia or ammoniacal liquor can be by simple side
Formula reclaims and is recycled to the removal step of lower batch glycin mother liquid；The result followed the tracks of with chemical analysis shows that glycine can increase
Add 1%～20%, the organic impurities such as acid amides in glycin mother liquid, peptide, glycolylurea, hydantoic acid, hydantoic acid acid amides almost 100%
It is converted into glycine；Mother liquor concentrations crystallization last handling process viscosity reduces, and salt particle diameter increases.The method can be by the content of impurity
Reduce floor level, improve crystalline mother solution quality, well solve to reduce cost, minimizing material consumption energy consumption, really realize cleaning
Produce, do not consume any soda acid, do not produce any salt and brine waste thereof, improve yield and the quality of product.
To this end, the present invention provides following technical scheme:
Remove the method for impurity in glycine crystallization mother liquid, specifically comprise the following steps that glycin mother liquid and ammonia or ammoniacal liquor in temperature
Be 80 DEG C～180 DEG C, pressure be reaction 30min～180min under 0.3MPa～5.5MPa.
Preferably, specifically comprise the following steps that by glycin mother liquid and ammonia or ammoniacal liquor temperature be 160～170 DEG C, pressure be
60～90min are reacted under 4.6MPa～5.2MPa.
It is furthermore preferred that the mass ratio of described glycin mother liquid and ammonia or ammoniacal liquor is 2～4.
Preferably, negative pressure ammonia excretion is also included after reaction；In order to improve raw material availability, cost-effective, more preferably will discharge
Ammonia recycles.
Preferably, described negative pressure reclaims the temperature of ammonia or ammoniacal liquor and is less than 75 DEG C, preferably 45～75 DEG C, most preferably 70 DEG C.
Preferably, described negative pressure reclaims the terminal of ammonia or ammoniacal liquor is that in glycine crystallization mother liquid, the content of free ammonia is less than 50ppm.
It is furthermore preferred that described glycin mother liquid is the crystalline mother solution of preparing glycine by hydroxy acetonitrile method.
Preferably, described crystalline mother solution is crude crystalline mother liquor or/and recrystallization mother liquor.
It is furthermore preferred that containing glycine and impurity in described crystalline mother solution, the mass percent of described glycine is 1%～30%,
The mass percent of described impurity is 0.1%～20%.
It is furthermore preferred that described impurity is glycine derivative.
Most preferably, described glycine derivative be glycine amide, glycine dipeptidase, glycine tripolymer, methylene amion acetic acid,
One or more in hydantoic acid, glycolylurea, hydantoic acid acid amides, 2,5-diketopiperazine.Wherein glycolylurea method prepares the sweet ammonia of glycine
Impurity in acid mother liquor is glycine derivative, as glycine amide, glycine dipeptidase, glycine tripolymer, methylene amion acetic acid,
In hydantoic acid, glycolylurea, hydantoic acid acid amides, 2,5-diketopiperazine one or more；Strecker method prepares the glycine of glycine
In brilliant mother liquor, impurity is dimer and the tripolymer of glycine, as glycine dipeptidase, methylene amion acetic acid, 2,5-diketopiperazine, sweet
In propylhomoserin tripolymer one or more；Above-mentioned impurity heats in the basic conditions, it is possible to be hydrolyzed to glycinate or glycine,
Wherein alkali can be NaOH, potassium hydroxide, sodium carbonate, potassium carbonate, barium hydroxide, calcium hydroxide, ammonia or ammoniacal liquor, excellent
Selecting ammonia or ammoniacal liquor, ammonia concn is preferably greater than 15% (wt).
Alkali owing to using in the present invention is ammonia or ammoniacal liquor, can by simple method ammonia driven out of from hydrolyzation system into
Row Recovery and recycle utilizes, and not only makes impurity be converted into glycine, additionally it is possible to make recovery ammonia recycle, and whole process does not consume appoints
What soda acid.
Special instruction, in these impurity, the Producing reason of methylene amion acetic acid is containing the completeest in raw material hydroxyl acetonitrile
The formaldehyde of full response, therefore the quality control of raw material serves certain effect to the quality of glycine, in order to stop to produce methylene
Amion acetic acid accessory substance, in the present invention, the hydroxyacetonitrile of particularly preferred hydrogen cyanide excess is raw material, or subtracts as far as possible
Few formaldehyde residual in raw material hydroxyl acetonitrile.The principle that methylene amion acetic acid produces is as follows:
The beneficial effects of the present invention is:
(1) after using ammonia or ammoniacal liquor alkaline hydrolysis, by hydrolyzation system being carried out negative pressure heating, completely can be by ammonia from hydrolysis
System separates and reclaims, whole during do not consume any soda acid, do not produce any salt and brine waste thereof, really do
To environment-protecting clean production technology；
(2) impurity such as hydrolysising peptide key and amido link and hydantoic acid, glycolylurea, hydantoic acid acid amides, and this can be effectively accomplished
A little impurity almost 100% are converted into glycine, improve the yield of glycine, it is possible to increase increase by 1%～20%, decrease sweet
The discharge of propylhomoserin mother liquor, decreases the loss late of glycine；
(3) use the impurity in ammonia or ammoniacal liquor hydrolysis glycin mother liquid, it is possible to the effective impurity removed in mother liquor, eliminate miscellaneous
Impact that confrontation Recycling Mother Solution is applied mechanically and the impact of glycine quality, and ammonia can not occur any reaction with glycine, does not disappears
Consume any soda acid, do not produce any salt and brine waste thereof, there is good environmental benefit and economic benefit.
Accompanying drawing explanation
In order to make the purpose of the present invention, technical scheme and beneficial effect clearer, the present invention provides drawings described below:
Fig. 1 is that Strecker method prepares glycine recrystallization mother liquor impurity.
Fig. 2 is the impurity in direct glycolylurea method glycin mother liquid.
Detailed description of the invention
Below in conjunction with accompanying drawing, the preferred embodiments of the present invention are described in detail.Unreceipted actual conditions in embodiment
Experimental technique, generally according to normal condition or according to the condition proposed by manufacturer.
Embodiment 1
Remove the method (constant-pressure and high-temperature processes glycine recrystallization mother liquor) of impurity in glycine crystallization mother liquid, specifically comprise the following steps that
By recrystallization mother liquor 500g (analysis result (w/w): glycine 20%, glycine dipeptidase 1.35%, the sweet ammonia of glycine
Acid tripeptides 0.65%, 2,5-diketopiperazines 1.10%) and 60% (w/w) ammoniacal liquor of 113g join in the four-hole boiling flask of 1000ml,
Then heating to temperature is to reflux 3 hours at 100 DEG C～110 DEG C, then under the conditions of negative pressure, temperature are 70 DEG C, ammoniacal liquor is evaporated off extremely
In mother liquor, the content of free ammonia is less than 50ppm, reclaims ammonia simultaneously, obtains glycine solution.Glycine solution is obtained after process
500g, following (w/w) through analyzing each constituent content in glycine solution: Glycine Levels 22.58%, glycine dipeptidase 0.35%,
Glycine tripeptide 0.10%, 2,5-diketopiperazine 0.50%.
From recrystallization mother liquor and the glycine solution of above-mentioned analysis glycine it can be seen that glycine recrystallization mother liquor is through ammonification
Water, is heated to reflux, and adds 2.58% before glycine mass ratio processes in glycine solution in crystalline mother solution, and impurity glycine
Dipeptides, glycine tripeptide, 2,5-diketopiperazine respectively than process before decrease 1%, 0.55%, 0.6% respectively, this illustrates part
Impurity in the presence of ammonia, makes it be converted into glycine through high temperature.But impurity can not be fully converted to glycine, and impurity is at mother liquor
In also have residual.
Embodiment 2
Remove the method (constant-pressure and high-temperature processes direct glycolylurea method glycine crystallization mother liquid) of impurity in glycine crystallization mother liquid, specifically
Step is as follows:
By recrystallization mother liquor 500g (analysis result (w/w): glycine 18%, glycine dipeptidase 1.35%, the sweet ammonia of glycine
Acid tripeptides 0.65%, 2,5-diketopiperazines 1.10%, hydantoic acid 0.96%, glycolylurea 1.74%, hydantoic acid acid amides 0.88%, glycine amide
0.98%) join in the four-hole boiling flask of 1000ml with 60% (w/w) ammoniacal liquor of 150g, then heat to 100 DEG C～110 DEG C and open
Beginning backflow, return time is 3 hours, then in negative pressure, ammoniacal liquor is evaporated off under the conditions of 70 DEG C and is less than to the content of free ammonia in mother liquor
50ppm, reclaims ammonia simultaneously, obtains glycine solution.Glycine solution 500g is obtained after process, water-soluble through analyzing glycine
In liquid, each constituent content is following (w/w): Glycine Levels 22.58%, glycine dipeptidase 0.35%, glycine tripeptide 0.10%,
2,5-diketopiperazines 0.50%, hydantoic acid 0.36%, glycolylurea 0.55%, hydantoic acid acid amides 0.18%, glycine amide 0.58%.
From recrystallization mother liquor and the glycine solution of above-mentioned analysis glycine it can be seen that glycine crystallization mother liquid is through adding ammoniacal liquor,
It is heated to reflux, crystalline mother solution adds before glycine mass ratio processes in glycine solution 4.7%, but impurity glycine dipeptidase,
Glycine tripeptide, 2,5-diketopiperazine, hydantoic acid, glycolylurea, hydantoic acid acid amides, glycine amide respectively than decreasing 1% before processing,
0.55%, 0.6%, 0.6%, 1.19%, 0.7%, 0.4%, this illustrates partial impurities in the presence of ammonia, makes it convert through high temperature
For glycine.But impurity can not be fully converted to glycine, impurity also has residual in mother liquor.
Embodiment 3
Remove the method (high temperature high pressure process glycine recrystallization mother liquor) of impurity in glycine crystallization mother liquid, comprise the steps:
By recrystallization mother liquor 500g (analysis result (w/w): glycine 20%, glycine dipeptidase 1.35%, the sweet ammonia of glycine
Acid tripeptides 0.65%, 2,5-diketopiperazines 1.10%) and 60% (w/w) ammoniacal liquor of 113g join in the autoclave of 1000ml,
Then heat to 165 DEG C, insulated and stirred 1 hour under pressure is 4.6MPa, it is subsequently cooled to 70 DEG C, pressure release to normal pressure, transfer
To cucurbit, then in negative pressure, ammoniacal liquor is evaporated off under the conditions of 70 DEG C to the content of free ammonia in mother liquor less than 50ppm, reclaim simultaneously
Ammonia, obtains glycine solution.Obtaining glycine solution 500g after process, in analysis glycine solution, each constituent content is such as
Under (w/w): Glycine Levels 23.7%, glycine dipeptidase 0.005%, glycine tripeptide 0.01%, 2,5-diketopiperazine 0.001%.
From recrystallization mother liquor and the glycine solution of above-mentioned analysis glycine it can be seen that glycine recrystallization mother liquor is through ammonification
Water, is heated to reflux, and glycine mass ratio in glycine solution adds 3.7% before processing, but impurity glycine dipeptidase, sweet
Propylhomoserin tripeptides, 2,5-diketopiperazine respectively than process before decrease 1.345%, 0.64%, 1.099%, this illustrates that partial impurities exists
In the presence of ammonia, through HTHP impurity almost 100% be converted into glycine.
Embodiment 4
Remove the method (high temperature high pressure process direct glycolylurea method glycine crystallization mother liquid) of impurity in glycine crystallization mother liquid, specifically
Step is as follows:
By recrystallization mother liquor 500g (analysis result (w/w): glycine 18%, glycine dipeptidase 1.35%, the sweet ammonia of glycine
Acid tripeptides 0.65%, 2,5-diketopiperazines 1.10%, hydantoic acid 0.96%, glycolylurea 1.74%, hydantoic acid acid amides 0.88%, glycine amide
0.98%) join in the autoclave of 1000ml with 60% (w/w) ammoniacal liquor of 150g, then heat to 160 DEG C, pressure
For insulated and stirred under the conditions of 4.6Mpa 1.5 hours, being subsequently cooled to 70 DEG C, pressure release, to normal pressure, is transferred in cucurbit, then negative
Pressure, in the ammonia mother liquid content of free ammonia is evaporated off under conditions of 70 DEG C, less than 50ppm, reclaims ammonia simultaneously, obtain glycine solution.
Glycine solution 500g is obtained after process, following (w/w) through analyzing each constituent content in glycine solution: glycine contains
Amount 25.2%, glycine dipeptidase 0.005%, glycine tripeptide 0.01%, 2,5-diketopiperazine 0.001%, hydantoic acid 0.0%, glycolylurea
0.0%, hydantoic acid acid amides 0.0%, glycine amide 0.0%.
From recrystallization mother liquor and the glycine solution of above-mentioned analysis glycine it can be seen that glycine crystallization mother liquid is through adding ammoniacal liquor,
Being heated to reflux, the glycine mass ratio in glycine solution adds 5.2% before processing, impurity glycine dipeptidase, glycine three
Peptide, 2,5-diketopiperazine, hydantoic acid, glycolylurea, hydantoic acid acid amides, glycine amide respectively than decreasing 1% before processing, 0.55%,
0.6%, 0.96%, 1.74%, 0.88%, 0.98%, this illustrates partial impurities in the presence of ammonia, through HTHP impurity almost
100% be converted into glycine.
Embodiment 5
Remove the method (high temperature high pressure process glycine recrystallization mother liquor) of impurity in glycine crystallization mother liquid, specifically comprise the following steps that
By recrystallization mother liquor 500g (analysis result (w/w): glycine 20%, glycine dipeptidase 1.35%, the sweet ammonia of glycine
Acid tripeptides 0.65%, 2,5-diketopiperazines 1.10%) join in the autoclave of 1000ml, in autoclave, it is passed through 90
Gram gas ammonia, then heat to 170 DEG C, pressure is insulated and stirred 1 hour under 5.2MPa, is subsequently cooled to 70 DEG C, and pressure release is to often
Pressure, is transferred in cucurbit, then in negative pressure, ammoniacal liquor is evaporated off under the conditions of 70 DEG C to the content of free ammonia in mother liquor less than 50ppm,
Reclaim ammonia simultaneously, obtain glycine solution.Glycine solution 500g is obtained, through analyzing in glycine solution each group after process
Divide content following (w/w): Glycine Levels 23.7%, glycine dipeptidase 0.005%, glycine tripeptide 0.01%, 2,5-diketone piperazine
Piperazine 0.001%.
From recrystallization mother liquor and the glycine solution of above-mentioned analysis glycine it can be seen that glycine recrystallization mother liquor is through ammonification
Water, is heated to reflux, and glycine mass ratio in glycine solution adds 3.7% before processing, and impurity glycine dipeptidase, sweet
Propylhomoserin tripeptides, 2,5-diketopiperazine respectively than process before decrease 1.345%, 0.64%, 1.099%, this illustrates that partial impurities exists
In the presence of ammonia, through HTHP impurity almost 100% be converted into glycine.
Embodiment 6
Remove the method (high temperature high pressure process direct glycolylurea method glycine crystallization mother liquid) of impurity in glycine crystallization mother liquid, specifically
Step is as follows:
By recrystallization mother liquor 00g (analysis result (w/w): glycine 18%, glycine dipeptidase 1.35%, the glycine of glycine
Tripeptides 0.65%, 2,5-diketopiperazine 1.10%, hydantoic acid 0.96%, glycolylurea 1.74%, hydantoic acid acid amides 0.88%, glycine amide 0.98%)
Joining in the autoclave of 1000ml, be passed through the gas ammonia of 90 grams in autoclave, then heat to 165 DEG C, pressure is
Insulated and stirred 1 hour under 5.2MPa, is subsequently cooled to 70 DEG C, and pressure release, to normal pressure, is transferred in cucurbit, then negative pressure, 70 DEG C
Under the conditions of the content of free ammonia is evaporated off in ammonia mother liquid less than 50ppm, reclaim ammonia simultaneously, obtain glycine solution.Obtain after process
Obtain glycine solution 500g, following (w/w) through analyzing each constituent content in glycine solution: Glycine Levels 25.2%,
Glycine dipeptidase 0.005%, glycine tripeptide 0.01%, 2,5-diketopiperazine 0.001%, hydantoic acid 0.0%, glycolylurea 0.0%, glycolylurea
Acid acid amides 0.0%, glycine amide 0.0%.
From recrystallization mother liquor and the glycine solution of above-mentioned analysis glycine it can be seen that, glycine crystallization mother liquid is through ammonification
Water, is heated to reflux, and adds 5.2% in glycine solution before the reaction of glycine mass ratio, and impurity glycine dipeptidase, sweet ammonia
Acid tripeptides, 2,5-diketopiperazine, hydantoic acid, glycolylurea, hydantoic acid acid amides, glycine amide respectively than decreasing 1% before reaction, 0.55%,
0.6%, 0.96%, 1.74%, 0.88%, 0.98%, this illustrates partial impurities in the presence of ammonia, through HTHP impurity almost
100% be converted into glycine.
In above-described embodiment, glycin mother liquid is 2～4 with the mass ratio of ammonia or ammoniacal liquor, is 80 DEG C～180 DEG C, pressure in temperature
Goal of the invention all can be realized for reacting 30min～180min under 0.3MPa～5.5MPa.
Finally illustrating, preferred embodiment above is only in order to illustrate technical scheme and unrestricted, although by above-mentioned
The present invention is described in detail by preferred embodiment, it is to be understood by those skilled in the art that can in form and
In details, it is made various change, without departing from claims of the present invention limited range.
Claims (8)
1. remove the method for impurity in glycin mother liquid, it is characterised in that specifically comprise the following steps that by glycin mother liquid and ammonia or ammoniacal liquor temperature be 80 DEG C～180 DEG C, pressure be reaction 30min～180min under 0.3MPa～5.5MPa；Containing glycine and impurity in described glycin mother liquid, the mass percent of described glycine is 1% ~ 30%, and the mass percent of described impurity is 0.1% ~ 20%；Described impurity is the glycine derivative that heating can be hydrolyzed to glycinate or glycine in the basic conditions.
Remove the method for impurity in glycin mother liquid the most according to claim 1, it is characterised in that specifically comprise the following steps that by glycin mother liquid and ammonia or ammoniacal liquor temperature be 160 ~ 170 DEG C, pressure be reaction 60 ~ 90min under 4.6MPa～5.2MPa.
The method of impurity in removal glycin mother liquid the most according to claim 1 or claim 2, it is characterised in that: described glycin mother liquid is 2 ~ 4 with the mass ratio of ammonia or ammoniacal liquor.
Remove the method for impurity in glycin mother liquid the most according to claim 1, it is characterised in that: also include negative pressure ammonia excretion after reaction.
Remove the method for impurity in glycin mother liquid the most according to claim 4, it is characterised in that: the temperature of described negative pressure ammonia excretion is less than 75 DEG C, and terminal is that in glycin mother liquid, the content of free ammonia is less than 50ppm.
The method of impurity in removal glycin mother liquid the most according to claim 1 or claim 2, it is characterised in that: described glycin mother liquid is the crystalline mother solution of preparing glycine by hydroxy acetonitrile method.
Remove the method for impurity in glycin mother liquid the most according to claim 1, it is characterised in that: described glycin mother liquid is glycine crude crystalline mother liquor or/and glycine recrystallization mother liquor.
Remove the method for impurity in glycine crystallization mother liquid the most according to claim 1, it is characterized in that: described glycine derivative be glycine amide, glycine dipeptidase, glycine tripolymer, methylene amion acetic acid, hydantoic acid, glycolylurea, hydantoic acid acid amides, 2, one or more in 5-diketopiperazine.
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