A kind of method of from sugared ammonium reaction solution, separating purifying polyhydroxy alkyl pyrazine
Technical field
The present invention relates to a kind of method of from sugared ammonium reaction solution, separating purifying polyhydroxy alkyl pyrazine.
Background technology
Polyhydroxy-alkyl-pyrazine is present in the plants such as pseudo-ginseng, tobacco.How basic alkyl pyrazine in the plant is to be obtained by Amadori rearrangement and serial complex reaction as glucose and aminocompound by the reducing sugar in the plant, and this class material can be used as cigaret additive with flavouring.Li Qi etc. SCI calendar year 2001 the 22nd volume 11 phases report from pseudo-ginseng, isolate 2-(1 ', 2 ', 3 '; 4 '-the tetrahydroxy butyl)-6-(2 "; 3 ", 4 " and the trihydroxy-butyl)-pyrazine and confirm its structure with synthetic method, and find that it has the good anticancer activity.U.S. Pat 6392042 discloses the how basic alkyl pyrazine class material that a class is used for the treatment of glycemia.Forefathers studies show that, sugar and aminocompound reaction usually generate more macromolecular substance, be called caramel colorant, its solubility property is very similar with the polyhydroxy-alkyl-pyrazine class, and is promptly soluble in water, unusual thickness after distillation dewaters, caking, the very difficulty of make to separate purifying normally adopts repeatedly chromatography of ions to handle, or removes macromolecular substance with gel chromatography etc.According to traditional method, if straight run distillation anhydrates, use organic solvent extraction again, very thickness, caking of system then, polyhydroxy-alkyl-pyrazine covered by macromolecular substance and the organic solvent contact area little, extraction efficiency is very low, and extracting solution contains more dark colour macromolecular substance, and the dark colour thick substances is arranged after the sedimentation; As use ion chromatography, and then need repeated multiple times to handle, and the concentration of polyhydroxy-alkyl-pyrazine is extremely low in the chromatographic eluents with chromatography of ions, polyhydroxy-alkyl-pyrazine is dissolved in the big water gaging, needs a large amount of pure water, also needs a large amount of energy distillations to anhydrate after handling.As use gel chromatography, and also there are many similar problems, handle inconvenient.
Summary of the invention
The invention discloses a kind of simply, convenient, effective, economical, can realize producing in enormous quantities that polyhydroxy-alkyl-pyrazine does not have macromolecular substance to cover substantially, the method for from sugared ammonium reaction solution, separating purifying polyhydroxy alkyl pyrazine that product purity is high.
The present invention realizes in the following manner:
The mixture that mixture that mixture that sugar and ammonium reaction are obtained or osamine reaction obtain or sugar and ammonia react obtain is through one or more levels nanofiltration membrane or ultra-filtration membrane or ultra-filtration membrane, the nanofiltration membrane combined films is held back the macromolecular substance of removing in the mixture, the film dialyzate that contains polyhydroxy-alkyl-pyrazine class material of macromolecular substance is removed, hold back feed liquid and then send raw material storage tank back to through pipeline through the film of membrane module, and then send into membrane module and separate, in the isolating later stage, can add the pure water dilution toward raw material storage tank, continue to pass through membrane module, the molecular weight cut-off of nanofiltration membrane component is not less than 200, and the molecular weight cut-off of hyperfiltration membrane assembly is not less than 1000.
Described nanofiltration membrane is meant the film of molecular weight cut-off between 200 to 1000, and ultra-filtration membrane is meant the film of molecular weight cut-off between 1000 to 50000.
The actual minimum of described nanofiltration membrane molecular weight cut-off is greater than the molecular weight of the isolating polyhydroxy-alkyl-pyrazine of wanting, and is not less than 100 with the difference of the molecular weight of polyhydroxy-alkyl-pyrazine, and the ultra-filtration membrane molecular weight cut-off is between 1000 to 20000.
Wherein the molecular weight cut-off of nanofiltration membrane to be being excellent between 400 to 800, and the ultra-filtration membrane molecular weight cut-off is being excellent between 1500 to 5000.
The mixture that described sugar and ammonium or amine or ammonia react obtain, after entering into the smart filter of secondary filter by topping-up pump, be pressed into through nanofiltration membrane or ultra-filtration membrane or pass through ultra-filtration membrane successively by high-pressure pump, the nanofiltration membrane combined films is held back the macromolecular substance of removing in the mixture, the film dialyzate that contains polyhydroxy-alkyl-pyrazine class material of macromolecular substance is removed, hold back feed liquid and then send raw material storage tank back to through pipeline through the film of membrane module, and then send into membrane module and separate, carry out along with isolating, see through nanofiltration membrane, the feed liquid of ultra-filtration membrane is more and more, and the feed liquid color is more and more darker in the raw material storage tank, the viscosity degree is increasing, and macromolecular substance concentration is more and more higher; In the isolating later stage, feed liquid is remaining about 1/1/3rd to ten o'clock in the head tank, can repeatedly add the pure water dilution toward raw material storage tank, continue nanofiltration or ultrafiltration, make polyhydroxy-alkyl-pyrazine see through membrane module together along with seeing through liquid as far as possible, by detecting (follow the tracks of as ultraviolet spectroscopy and detect) through the concentration that sees through polyhydroxy-alkyl-pyrazine in the liquid behind the membrane module, the concentration of polyhydroxy-alkyl-pyrazine is very low in seeing through liquid stops dilution maybe can't detecting the time, collect all and obtain the film dialyzate through liquid, through concentrating, extract, decolouring, crystallization or can obtain purified polyhydroxy-alkyl-pyrazine class material in conjunction with technology such as chromatograms can be used as spices or medical material etc.Wherein remove most macromolecular substance in the mixture, further be treated to preferred plan through nanofiltration membrane again earlier sugared ammonium reaction solution is held back with ultra-filtration membrane.
The working pressure of described nanofiltration or ultrafiltration be 0.1MPa between the 3.5MPa, the controlling diaphragm flux is 1L/m
2.h
-1To 50L/m
2.h
-1Between, service temperature is between 0 ℃ to 60 ℃
The preferable working pressure of described nanofiltration or ultrafiltration be 1.0MPa between the 2.5MPa, preferable membrane flux is at 10L/m
2.h
-1To 40L/m
2.h
-1Between, preferable service temperature is between 0 ℃ to 40 ℃.
The actual minimum of nanofiltration membrane molecular weight cut-off is greater than the molecular weight of the isolating polyhydroxy-alkyl-pyrazine of wanting, and is not less than 100 with the difference of the molecular weight of polyhydroxy-alkyl-pyrazine.Nanofiltration is better than the effect of ultrafiltration except that the effect of polymkeric substance.As separating 2-methylol-6-methylpyrazine (molecular weight is 124), the nanofiltration membrane molecular weight cut-off preferably is greater than 220; As separate 2,5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine, the nanofiltration membrane molecular weight cut-off is greater than 320, preferably is greater than 420.
Sugared ammonium reaction solution of the present invention is meant that sugar and ammonium salt react resulting product, or sugar and ammoniacal liquor react resulting product, or the product that obtains of osamine or its salt self condensation, or sugar and amino acid whose reaction product, or the mixture of amino acid, ammonium salt, ammoniacal liquor or osamine reacts the reaction product that obtains with sugar.Wherein sugar can be that aldose also can be a ketose; Can be hexose such as glucose and fructose; Or pentose or tetrose; Or triose such as Glycerose; Can be monose or disaccharide such as maltose; Or oligose; Or the mixture of the mixture of above-mentioned several sugar such as glucose, fructose and Glycerose.Wherein ammonium salt can be ammonium salt such as ammonium chloride or the acid salt such as the bicarbonate of ammonia of organic acids such as carbonic acid, sulfuric acid, hydrochloric acid, formic acid, acetate, nitric acid, phosphoric acid and mineral acid; Or the mixture of the mixture of above-mentioned ammonium salt such as ammonium chloride and volatile salt.Osamine is meant amination product such as the glucosamine and the fructosamine of aforesaid sugar, or the mixture of several osamines.Ammonia is meant ammonia or ammoniacal liquor.Amino acid is meant the 20 kinds of common a-amino acids existing in the organism such as the mixture of Padil, α-An Jibingsuan and common a-amino acid.
The material of described nanofiltration membrane or ultra-filtration membrane is polysulfones, polyethersulfone, polymeric amide, polyimide, polysulfonamides, polyolefine, fluorine material, cellulose esters, ceramic membrane, glassy membrane, polyester or silicon-containing polymer etc.
Described nanofiltration membrane or ultra-filtration membrane are rolled film, hollow-fibre membrane, tubular membrane or plate and frame film.
It is reinforced to improve cigarette odor-absorbing or to be used for others that the feed liquid that obtains can be directly used in cigarette flavoring.This method can be used for separating from sugared ammonium (amine or ammonia) reaction solution the mixture of the compound of various pure compounds below the purification or following these similar: 2, and 6-dihydroxymethyl pyrazine; 2,5-two-methylol pyrazine; 2-methylol-6-methylpyrazine; 2-methylol-5-methylpyrazine; 2,5-two (1 ', 2 '-dihydroxy ethyl) pyrazine; 2,6-two (1 ', 2 '-dihydroxy ethyl) pyrazine; 2-(1 ', 2 '-dihydroxy ethyl)-5-(2 " hydroxyethyl) pyrazine; 2-(1 ', 2 '-dihydroxy ethyl)-6-(2 " hydroxyethyl) pyrazine; 2-(1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl)-5-(2 ", 3 ", 4 " and the trihydroxy-butyl)-pyrazine; 2-(1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl)-6-(2 ", 3 ", 4 " and the trihydroxy-butyl)-pyrazine; 2,6-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine; 2,5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine; 2-(1 ', 2 ', 3 '-the trihydroxy-propyl group)-5-(2 ", 3 " dihydroxypropyl) pyrazine; 2-(1 ', 2 ', 3 '-the trihydroxy-propyl group)-6-(2 ", 3 " dihydroxypropyl)-pyrazine; 2,6-two (1 ', 2 ', 3 '-the trihydroxy-propyl group) pyrazine; 2,5-two (1 ', 2 ', 3 '-the trihydroxy-propyl group) pyrazine; And the various optically active isomers of above-claimed cpd.Their structure is expressed as follows:
N is a numeral 0 or 1 or 2 or 3
N is that numeral 0 or 1 or 2 n are numeral 0 or 1 or 2
In the actual membrane sepn process, can be according to whether earlier feed liquid being filtered with secondary filter is smart before decision nanofiltration of supplied materials situation or the ultrafiltration.The purpose of smart filter is the large particulate matter of removing in the feed liquid, to prevent their damage nanofiltration membrane or ultra-filtration membranes, guarantees the normal work-ing life of membrane module.Feed liquids all in the embodiment of the invention are clear liquor, do not see suspended substance, and all filter with the G4 sand core funnel before the experiment, not with the smart filter of secondary filter.
Method with membrane separation process purifying polyhydroxy alkyl pyrazine from sugared ammonium (amine or ammonia) reaction solution disclosed by the invention compares with traditional method, has many good qualities.According to traditional method, if straight run distillation anhydrates, use organic solvent extraction again, very thickness, caking of system then, polyhydroxy-alkyl-pyrazine covered by macromolecular substance and the organic solvent contact area little, extraction efficiency is very low, and extracting solution contains more dark colour macromolecular substance, and the dark colour thick substances is arranged after the sedimentation; As use ion chromatography, and then need repeated multiple times to handle, and the concentration of polyhydroxy-alkyl-pyrazine is extremely low in the chromatographic eluents with chromatography of ions, polyhydroxy-alkyl-pyrazine is dissolved in the big water gaging, needs a large amount of pure water, also needs a large amount of energy distillations to anhydrate after handling.As use gel chromatography, and also there are many similar problems, handle inconvenient.According to the method with membrane separation process purifying polyhydroxy alkyl pyrazine from sugared ammonium (amine or ammonia) reaction solution disclosed by the invention, only need by nanofiltration or ultrafiltration reaction mixture, later stage is repeatedly added pure water on a small quantity, just can effectively be removed the night that sees through of macromolecular substance, and dilute strength is little; And organic solvent extraction was simple, convenient, effective, economical after distillation was anhydrated, and polyhydroxy-alkyl-pyrazine does not have macromolecular substance to cover the product purity height that obtains substantially.
Description of drawings
Accompanying drawing is a process schematic representation of the present invention
Embodiment
Embodiment 1
Nano filtering process separates from the reaction mixture of glucosamine and ammoniacal liquor purifies 2,5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine
20000 gram glucosamine hydrochlorides are dissolved in 20000 milliliter of 28% ammoniacal liquor, stirring at room 21 days.At working pressure is under the 3.5MPa, it is 500 tubular type nanofiltration membrane component that the mixture that reaction is obtained feeds molecular weight cut-off from raw material storage tank with pressure, 2,5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) the pyrazine aqueous solution sees through nanofiltration membrane and collects through flow container, and macromolecular substance is held back the back by membrane module and is sent raw material storage tank along with the feed liquid that does not see through membrane module back to through pipeline, and then sends into membrane module and separate, and so circulation separates.Membrane flux is at 20L/m
2.h
-1To 40L/m
2.h
-1Between change 40-50 ℃ of control feed temperature.Carry out along with isolating, the film dialyzate that sees through nanofiltration membrane is more and more, and the feed liquid color is more and more darker in the raw material storage tank, and the viscosity degree is increasing, and macromolecular substance concentration is more and more higher.In the isolating later stage, during about 2 liters of raw material storage liquid storage, add 6 liters of pure water dilutions toward raw material storage tank, continue nanofiltration separation.Add water so repeatedly about 7 times, to seeing through the liquid very slight color, and ultraviolet spectroscopy (wavelength 275 nanometers) quantitatively shows 2,5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine concentration stops nanofiltration when very low.The liquid decompression rotary evaporation of collecting that sees through is anhydrated, adding an amount of dehydrated alcohol azeotropic then anhydrates, extract with the dehydrated alcohol heating again, the extracting solution crystallisation by cooling obtains yellow crystals, crystal gets 2 with the organic solvent recrystallization is dry, 5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine white powder 6770 grams (productive rate about 46%).
13CNMR (D
2O) δ 65.75 (C4 ' and C4 "), 74.03 (C3 ' and C3 "), 74.38 (C1 ' and C1 "), 76.38 (C2 ' and C2 "), 145.12 (C3 and C6), 158.20 (C2 and C5).FAB-MS m/z:321.1289 (M+H)
+, C
12H
21N
2O
8, promptly the molecular formula of product is C
12H
20N
2O
8
From the reaction mixture of glucosamine and ammoniacal liquor, separate purification 2 with ion chromatography, 5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) the pyrazine contrast
25 gram glucosamines and 25 milliliter of 28% ammoniacal liquor stirring at room 21 days.The mixture that obtains neutralizes with dilute hydrochloric acid, separates with ion chromatography then.With Dowex 50W * 4 post (Hydrogens, the 100-200 order), uses the deionized water wash-out, about 20000 milliliters of shared deionized water, collecting corresponding elutriant underpressure distillation anhydrates, extract with the dehydrated alcohol heating, the extracting solution crystallisation by cooling obtains yellow crystals, and crystal gets 2 with the organic solvent recrystallization is dry, 5-two (1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl) pyrazine white powder 7.4 grams (productive rate about 40%).
The present invention and ion chromatography are compared, can find out that the present invention has a clear superiority in than chromatography.
Embodiment 2
Ultrafiltration process is separated the mixture of purification 2-methylol-5-methylpyrazine and 2-methylol-6-methylpyrazine from 1 in the reaction mixture of 3-otan and ammonium acetate
46 grams 1, the 3-otan is dissolved in dehydrated alcohol, is added drop-wise in the 58 gram ammonium acetates, keeps refluxing in the dropping process, drips the back and refluxes 3 hours.The mixture that after having reacted reaction has been obtained in the ultrafiltration cup is 1500 ultra-filtration membrane ultrafiltration with molecular weight cut-off, and as power, adjusting pressure is 0.3MPa with pressurized air, collects ultrafiltrated.This service temperature is 20-30 ℃.The ultrafiltration later stage is added dehydrated alcohol dilution repeatedly and continues ultrafiltration, each 100 milliliters, detects in the ultrafiltrated 2-methylol-5-methylpyrazine and till the 2-methylol-6-methylpyrazine content is very low until GC-MS.The ultrafiltrated reduction vaporization is desolventized, and 75 ℃/8Pa cut is collected in underpressure distillation then, promptly gets the mixture yellow oil of 3.9 gram 2-methylol-5-methylpyrazines and 2-methylol-6-methylpyrazine, productive rate 12%.MS(m/z):124(m
+,91),95(100),66(19),55(27),42(32),39(44)。
1HNMR (D
2O): primary product δ 2.57 (s, 3H, CH
3), 4.78 (s, 2H, CH
2), 8.39 (s, 1H, CH), 8.54 (s, 1H, CH); Secondary product δ 2.57 (s, 3H, CH
3), 4.78 (s, 2H, CH
2), 8.37 (s, 1H, CH), 8.46 (s, 1H, CH).
Embodiment 3
Ultrafiltration process from the reaction mixture of glucose, fructose and Secondary ammonium phosphate preliminary purification 2-(1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl)-5-(2 "; 3 ", 4 " and the trihydroxy-butyl)-pyrazine and 2-(1 ', 2 ', 3 '; 4 '-the tetrahydroxy butyl)-6-(2 ", 3 ", 4 " and the trihydroxy-butyl)-pyrazine
360 gram glucose, 360 gram fructose and 540 gram Secondary ammonium phosphates were dissolved in 2000 ml waters, in 90-95 ℃ of reaction 3 hours.It is 5000 polysulfone hollow fiber ultrafiltration membrane system that the mixture that reaction is obtained feeds molecular weight cut-off from raw material storage tank with pressure, and working pressure is 0.3MPa, and controlled temperature is 30 to 40 ℃.Contain 2-(1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl)-5-(2 ", 3 ", 4 " trihydroxy-butyl) pyrazine and 2-(1 '; 2 '; 3 ', 4 '-the tetrahydroxy butyl)-6-(2 ", 3 "; 4 "-trihydroxy-butyl) aqueous solution of pyrazine is collected through flow container through ultra-filtration membrane, and macromolecular substance is held back the back by membrane module and is sent raw material storage tank along with the feed liquid that does not see through membrane module back to through pipeline, and then sends into membrane module and separate, and so circulation separates.Carry out along with isolating, the feed liquid that sees through nanofiltration membrane is more and more, and the feed liquid color is more and more darker in the raw material storage tank, and the viscosity degree is increasing.In the isolating later stage, during about 0.5 liter of raw material liquid storage, add 1 liter of pure water dilution toward raw material storage tank, continue ultra-filtration and separation.Add water so repeatedly, extremely see through the liquid very slight color, and UV spectrum standard measure (wavelength 275 nanometers) demonstration 2-(1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl)-5-(2 ", 3 ", 4 " trihydroxy-butyl) pyrazine and 2-(1 '; 2 ', 3 ', 4 '-the tetrahydroxy butyl)-6-(2 ", 3 ", 4 " trihydroxy-butyl) pyrazine concentration stops ultrafiltration when very low.
Last remaining material is thick brownish black syrupy shape material in the ultra-filtration equipment.This material is water-soluble, separate and analyze with the exclusion gel chromatography, find that its main component is a hydrophilic polymers, its molecular-weight average is greater than 10000
With not carrying out the reaction solution of ultrafiltration and seeing through the ultrafiltrated sampling of ultra-filtration membrane, carry out compartment analysis relatively with the exclusion gel chromatography respectively, the result shows, with uf processing not relatively, the polymer quality content of solution minimizing 80% after the ultrafiltration.
That collects sees through liquid can be directly used in cigarette charging or other after removing inorganic salt; Also can through aftertreatment, extraction, crystallization recrystallization dry 2-(1 ', 2 ', 3 ', 4 '-the tetrahydroxy butyl)-5-(2 "; 3 ", 4 " and the trihydroxy-butyl) pyrazine and 2-(1 ', 2 ', 3 '; 4 '-the tetrahydroxy butyl)-6-(2 ", 3 ", 4 " and the trihydroxy-butyl) pyrazine mixture white powder.FAB-MS m/z:M+H peak 305.1342, C
12H
21O
7N
2, promptly the molecular formula of product is C
12H
20O
7N
2LC-MS detects and finds have two M+H peak m/z to be 305 chromatographic peak.
Embodiment 4
The ultrafiltration nano filtering process from the reaction mixture of L-sorbose, ammonium formiate, separate purification 2-(1 ' R, 2 ' S, 3 ' S, 4 '-the tetrahydroxy butyl)-6-(2 ' S, 3 ' S, 4 '-the trihydroxy-butyl) pyrazine.
300 gram L-sorboses, 270 gram ammonium formiates are dissolved in 1000 ml waters, back flow reaction 2.5 hours.Ultrafiltration is carried out according to the method for embodiment 3 in the cooling back, removes the most of polymkeric substance in the reaction mixture earlier and the target product dialysis is finished; Then the dialyzate that obtains is carried out nanofiltration according to the method for embodiment 1, remove wherein remaining a spot of polymkeric substance and part molecular weight greater than 400 and less than other by product of 1000.After the dialyzate that nanofiltration is obtained is removed remaining ammonium formiate with proper method at last, reduction vaporization dewaters, the ethanol heating is extracted, crystallisation by cooling, dry 2-(1 ' R, the 2 ' S of getting of organic solvent recrystallization, 3 ' S, 4 '-the tetrahydroxy butyl)-6-(2 ' S, 3 ' S, 4 '-the trihydroxy-butyl) pyrazine 50.6 grams (productive rate 20%).115 ℃ of Mp, FAB-MS m/z:M+H peak 305.1342, C
12H
21O
7N
2, promptly the molecular formula of product is C
12H
20O
7N
2
Nanofiltration disclosed by the invention or ultrafiltration or ultrafiltration and nanofiltration bonded method are adopted in above embodiment explanation, can separate the polymkeric substance of removing in the system effectively from sugared ammonium (amine or ammonia) reaction solution, thereby make further separation and purification become simple.In this way, can realize the batch process preparation of polyhydroxy-alkyl-pyrazine class material more conveniently.This method is different from traditional separating and purifying method, has many good qualities.The low problem of extraction efficiency that this method has been avoided straight run distillation to anhydrate bringing with organic solvent extraction again; This method has also avoided polyhydroxy-alkyl-pyrazine material that ion chromatography and gel chromatography bring by the extremely low problem of polyhydroxy-alkyl-pyrazine concentration in high dilution, the elutriant.Polyhydroxy-alkyl-pyrazine is dissolved in the big water gaging, needs a large amount of pure water, also needs a large amount of energy distillations to anhydrate after handling.As usefulness, also there are many similar problems, handle inconvenient.According to the method with membrane separation process purifying polyhydroxy alkyl pyrazine from sugared ammonium (amine or ammonia) reaction solution disclosed by the invention, only need by nanofiltration or ultrafiltration reaction mixture, later stage is repeatedly added pure water on a small quantity, just can effectively be removed the night that sees through of macromolecular substance, and dilute strength is little; And organic solvent extraction was simple, convenient, effective, economical after distillation was anhydrated, and polyhydroxy-alkyl-pyrazine does not have macromolecular substance to cover the product purity height that obtains substantially
In sum, the invention discloses and a kind ofly from sugared ammonium (amine or ammonia) reactant liquor, purify many with membrane separation process The method of hydroxy alkyl pyrazine, the method that can be combined with nanofiltration with nanofiltration or ultrafiltration or ultrafiltration from sugared ammonium (amine or Ammonia) separate the polymer remove in the system in the reactant liquor, thereby so that further separation and purification become simply, More easily realize the batch production preparation of Polyhydroxyalkylpyraderivatives class material. Use method disclosed by the invention, In the process of purifying polyhydroxy alkyl pyrazine, Polyhydroxyalkylpyraderivatives dilutes from sugared ammonium (amine or ammonia) reactant liquor Degree is little, and distillation anhydrate rear organic solvent extraction and crystallization become simply, convenient, effective, economical, obtain The product purity height.