CN101914022B - Method for producing methyl lactate with high content and high optical purity in two steps - Google Patents
Method for producing methyl lactate with high content and high optical purity in two steps Download PDFInfo
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Abstract
The invention relates to a method for producing methyl lactate with high content and high optical purity from lactide and methanol through ester exchange reaction in two steps. The method comprises the following steps of: adding a catalyst to a lactic acid to carry out polycondensation reaction to obtain the lactate oligomer with the molecular weight of 1,000-2,500; adding a catalyst to the lactate oligmer to carry out depolymerization reaction to obtain the crude lactide; refining the lactide, and carrying out full-reflux reaction on the refined lactide and the absolute methanol to obtain the methyl lactate. The process is simple, the content of synthesized methyl lactate is more than 99.5%, and the optical purity can achieve more than 99%.
Description
Technical field
The invention belongs to field of chemical technology, being specifically related to a kind of is direct material by rac-Lactide and anhydrous methanol, produces the method for high-content and high-optical-purity methyl lactate by the transesterification reaction two step method.
Background technology
Methyl lactate has peat-reek, is a kind of important fine chemical material.Because methyl lactate contains unsymmetrical carbon, therefore have two kinds of optical isomers, it also is a kind of optically active essential industry solvent that has, can be used as the solvent of nitrocotton, acetate fiber, methanolic acid resin, shell pine ester, Manila resin, rosin, shellac, ethenoid resin, paint etc., still is the senior solvent of olivet class simultaneously.Also be used as softening agent at other industrial circle, in asymmetric synthesis, be used for synthetic having optically active carboxylicesters, had extensive use in industries such as food, wine brewing, chemical industry, medicine.
Simultaneously since methyl lactate have nontoxic, solvability good, little characteristics such as volatile, has biodegradable again, so methyl lactate is again to have that exploitation is worth and " green solvent " of application prospect.Along with improving constantly of people's living standard, more and more higher to environment requirement, and mostly be poisonous solvent at the solvent of industrial use at present, environment and the mankind have been caused great harm, as halo class, ethers, chloro-fluorocarbon kind solvent etc., so methyl lactate has broad application prospects as " green solvent ".The at present domestic relevant patent that does not also have methyl lactate to synthesize.
Summary of the invention
The objective of the invention is to overcome the existing existing defective of methyl lactate production technology, provide a kind of two step method to produce the method for high-content and high-optical-purity methyl lactate, this method technology is simple, operates simple and easy, be fit to suitability for industrialized production and use, and do not have " three wastes " discharging.It is the raw material synthesis of lactide from that this method at first adopts lactic acid, is raw material synthesizing lactic acid methyl esters with refined lactide and anhydrous methanol again, and the whole piece operational path can be divided into lactide production and lactate is produced two flow processs, so we are referred to as " two step method ".
Technical solution of the present invention is achieved in that it may further comprise the steps:
A, lactic acid polycondensation: add catalyzer in lactic acid, the weight ratio of catalyzer and lactic acid is 0.1/10000～10/10000, and preferred ratio is 1/10000; Carry out polycondensation after adding, sustained reaction is 1～4 hour under the condition of 80～180 ℃ of temperature, vacuum tightness 20000～2000Pa, namely obtains molecular weight at 1000～2500 lactic acid oligomer.
B, oligopolymer depolymerization: add catalyzer in lactic acid oligomer, the weight ratio of catalyzer and lactic acid oligomer is 0.1/10000～10/10000, and preferred ratio is 1/10000; Add the back in depolymerizing reactor, successive reaction under the condition of 200～250 ℃ of temperature, vacuum tightness 3000～50Pa, namely the sustainable content that obtains is in 80%～95% crude product of lactide.
C, rac-Lactide purifying: crude product of lactide is made with extra care, obtain content more than 99.5%, optical purity is in the refined lactide more than 99%.
D, methyl lactate are synthetic: refined lactide and anhydrous methanol are added reactor by weight 1: 0.45～1: 2.5 ratio, are that 10/1000～100/1000 ratio adds catalyzer then by weight, and preferably weight ratio is that weight ratio is 50/1000; Under the condition of 50～150 ℃ of temperature, normal pressure, continuously stirring was carried out total reflux reaction 1～10 hour, obtained methyl lactate.
E, methyl lactate purifying: methyl lactate is carried out purifies and separates.
The present invention's technical solution preferably is: before the lactic acid polycondensation, under vacuum tightness 10000～500Pa condition, under the condition that distillation temperature is 40～90 ℃ lactic acid is carried out vacuum distilling earlier, remove free-water wherein.
Wherein: the catalyzer that adds in lactic acid polycondensation and oligopolymer depolymerization is at least a in zinc class catalyzer, tin class catalyzer or the organic catalyst, and the weight ratio of its adding is 0.1/10000～5/10000, preferred 1/10000.The composite catalyst of one or more in preferred zinc lactate, zinc oxide, zinc powder, zinc ethyl, lactic acid tin, stannic oxide, tindioxide, tin protoxide, the inferior tin of lactic acid, stannous octoate, tin protochloride, glass putty, propionic acid or the butyl (tetra) titanate.Preferred catalyzer is that zinc oxide, stannic oxide and butyl (tetra) titanate are 1: 1: 1 mixture by weight.
Wherein: the catalyzer that adds in methyl lactate is synthetic is one or both in exchange resin or the high strong acid catalyst of solid, and the weight ratio of its adding is 10/1000～100/1000.Preferred hydrogen type cation exchange resin or SO
4 2-The composite catalyst of one or both in the high strong acid catalyst of/TiO2 solid.Preferred hydrogen type cation exchange resin and SO
4 2-The high strong acid of/TiO2 solid is 1: 1 composite catalyst by weight.
Wherein: the method for among the step C crude product of lactide being made with extra care is recrystallization, rectification under vacuum or fusion-crystallization, or two kinds and two or more combinations in the above-mentioned process for purification.Preferred first recrystallization is fusion-crystallization again.
Wherein: in the step e methyl lactate being carried out purifies and separates is methyl lactate to be joined rectifying tower carry out rectifying; the rectifying tower atmospheric operation; cat head and tower reactor pressure reduction are 1.5～3KPa; the tower reactor temperature is 140 ℃～150 ℃; tower top temperature is 65 ℃; the tower side outlet obtains content at the methyl lactate product more than 99.5%, and cat head obtains the methyl alcohol of content more than 99.5%, overflows content at the bottom of the tower at the lactoyl methyl lactate more than 99.5%.The lactoyl methyl lactate that overflows at the bottom of the tower can return and participate in the methyl lactate building-up reactions in the reactor of step D.The methyl alcohol that cat head obtains can return and participate in the methyl lactate building-up reactions in the reactor of step D.
Compared with prior art, technical superiority of the present invention is:
1, the present invention produces central refined lactide and the anhydrous methanol of adopting of operational path of methyl lactate as direct material, being different from traditional technology adopts lactic acid and methyl alcohol as direct material, comparatively speaking, this technology has following characteristics: one, be raw material production reaction intermediate rac-Lactide with lactic acid, as everyone knows, lactic acid has two kinds of isomerss, the physicochemical characteristic of D-lactic acid and dextrolactic acid is very approaching, adopt common separating technology to be difficult to it is separated, and the optics content of lactic acid will directly influence the optics content of product methyl lactate.Rac-Lactide has two kinds of isomerss, four kinds of different existing waies: left-handed type, dextrorotatory form, racemize type and meso-form, left-handed and the fusing point dextrorotation rac-Lactide is 95 ℃～98 ℃, the fusing point of rac-lactide is 124 ℃～126 ℃, and the fusing point of Study of Meso-Lactide is 50 ℃～52 ℃, four under same temperature in the same solvent solubleness very big difference is also arranged, mesomeric maximum, left-handed and dextrorotation rac-Lactide takes second place, and the rac-Lactide minimum is revolved in export trade, and it is also bigger that four boiling point differs.So just it can be separated by common separate mode, this operational path adopts is one or both and two or more combination in solvent recrystallization, rectification under vacuum, the fusion-crystallization, rac-Lactide after refining, content can reach more than 99.5%, optical purity can reach more than 99%, and water content is below 0.05%.Two, because extremely low as the moisture content of the anhydrous methanol of raw material and refined lactide, and the transesterification reaction of carrying out can not produce reaction water, so entire reaction course need not to be with aqua, and reaction can carry out very thorough.Water content in the product methyl lactate can be accomplished very low.Three, the optical purity of refined lactide can reach more than 99.5%, and the upset of configuration can not take place transesterification reaction, so synthetic methyl lactate optical purity can reach more than 99.5%.
2, the present invention adopts hydrogen type cation exchange resin and SO
4 2-The high strong acid of/TiO2 solid is wherein a kind of as catalyzer or two kinds of composite catalysts that mix with certain proportion, use the vitriol oil to compare as catalyzer with traditional technology, have following advantage: one, efficient, only need to add 10/1000～100/1000 of rac-Lactide weight and can reach the effect that improves speed of reaction.Two, can reuse, through using for a long time, the catalytic effect of catalyzer can reduce, and only needs this moment catalyzer to be taken out by the mode of filtering, and handles through super-dry and simple the activation again, and catalyzer just can be reused.Three, can not cause corrosion to equipment, can significantly reduce investment cost of equipment.Four, this type of catalyzer is in the middle of entire reaction course; only play the effect that accelerated reaction is carried out; and can not make reactant and product that other side reaction takes place; basically the unreacted methanol that only exists in the methyl lactate mother liquor, reaction product methyl lactate, reaction carry out not thoroughly and the lactoyl methyl lactate that produces, reduce the difficulty of rectifying separation greatly.Five, no spent acid discharging can not cause environmental pollution.
3, separation and purification methyl lactate of the present invention can adopt the mode of atmospheric distillation or rectification under vacuum.Because mention in the above-mentioned advantage introduction that component has only three kinds in the methyl lactate mother liquor; excessive methyl alcohol, reaction product methyl lactate and unreacted be the lactoyl methyl lactate completely; and three's separation factor is very big; so only need a rectifying tower just can reach the purpose of separation; tower side discharge port obtains the methyl lactate product; excessive methanol, overflow lactoyl methyl lactate at the bottom of the tower are reclaimed in the cat head cooling.
4, operational path of the present invention is an environmental protection, pollution-free green route.One, the distilled water of lactic acid polycondensation process generation can satisfy the workshop ordinary production fully, cleaning is required, and the whole piece operational path does not have the demand of clean water substantially; Two, catalyzer can be reused, and not can with reactant generation side reaction, do not have the discharging of spent catalyst and byproduct of reaction; Three, three kinds of components are through after the rectifying separation in the reacted mother liquor, and methyl lactate is sold as product, reclaim methyl alcohol and lactoyl methyl lactate and can return the participation reaction of transesterify workshop section, so not waste of raw material can all be converted into product.Just there is not the discharging of waste water,waste gas and industrial residue yet.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail.
Example one:
Raw material is the lactic acid of 88% content of outsourcing, adopts falling-film evaporator that material acid is carried out vacuum distilling, and the temperature of charge of keeping in the falling-film evaporator reaches 50 ℃, and vacuum tightness maintains 8000Pa, the lactic acid after concentrating wherein monomer content more than 99%.Lactic acid 500Kg after concentrating is conveyed into polycondensation vessel by transferpump; be that 5/10000 ratio adds zinc lactate as catalyzer in the weight ratio of zinc lactate and lactic acid; in 2 hours; material is risen to 120 ℃ from 80 ℃; vacuum tightness maintains 5000Pa; entire reaction is carried out having under the condition of stirring; detect the viscosity of lactic acid oligomer by in-line viscometer; according to the viscosity molecular weight contrast relationship; determine that its molecular weight is whether between 1000～2500; if molecular weight is within this scope; by height pressure difference and vacuum pressure reduction lact-acid oligomer is conveyed into the depolymerization still; be that 5/10000 ratio adds zinc lactate as catalyzer in the weight ratio of zinc lactate and lactic acid; entire reaction is carried out having under the condition of stirring; material is warming up to 180 ℃ rapidly; vacuum tightness maintains 1000Pa; after the rac-Lactide vapor condensation that continues to obtain; enrichment in holding tank, in the depolymerization still material depolymerization complete, rac-Lactide go out that speed becomes very slowly the time; depolymerization reaction stops; liquid lactide in the holding tank enters purifying workshop section by transferpump, by recrystallization purifying process, obtains refined lactide 370Kg; content reaches 99.7%, and optical purity reaches 99.7%.Again refined lactide 370Kg is added esterifying kettle by handling equipment, in esterifying kettle, add anhydrous methanol 500Kg simultaneously, be that 60/1000 ratio adds hydrogen type cation exchange resin as catalyzer according to the weight ratio of hydrogen type cation exchange resin and rac-Lactide, 85 ℃ of temperature of charge, under the condition of normal pressure, continuously stirring total reflux transesterification reaction 3 hours, the mother liquor that reaction is finished enters surge tank by height pressure difference, by transferpump mother liquor is imported rectifying tower continuously again, control the rectifier bottoms temperature of charge at 145 ℃～150 ℃, 65 ℃ of tower top temperatures, cat head tower bottom pressure difference is 1.8KPa, cat head continues recovery methyl alcohol, continue the overflow heavy constituent at the bottom of the tower, the tower side outlet continues the methyl lactate product, and rectifying finishes, obtain content 99.5% altogether, optical purity is 99.7% methyl lactate 525Kg.The lactoyl methyl lactate that overflows at the bottom of the tower can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.The methyl alcohol that cat head obtains can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.
Example two:
Lactic acid 500Kg after concentrating is conveyed into polycondensation vessel by transferpump; be that 8/10000 ratio adds zinc oxide as catalyzer in the weight ratio of zinc oxide and lactic acid; in 2 hours; material is risen to 120 ℃ from 80 ℃; vacuum tightness maintains 4000Pa; entire reaction is carried out having under the condition of stirring; detect the viscosity of lactic acid oligomer by in-line viscometer; according to the viscosity molecular weight contrast relationship; determine that its molecular weight is 1600; polycondensation is finished; by height pressure difference and vacuum pressure reduction lact-acid oligomer is conveyed into the depolymerization still; be that 10/10000 ratio adds zinc oxide as catalyzer in the weight ratio of zinc oxide and lactic acid; entire reaction is carried out having under the condition of stirring; material is warming up to 185 ℃ rapidly; vacuum tightness maintains 1500Pa; after the rac-Lactide vapor condensation that continues to obtain; enrichment in holding tank, in the depolymerization still material depolymerization complete, rac-Lactide go out that speed becomes very slowly the time; depolymerization stops; liquid lactide in the holding tank enters purifying workshop section by transferpump, by the fusion-crystallization purifying technique, obtains refined lactide 350Kg; content reaches 99.6%, and optical purity reaches 99.6%.Again refined lactide 350Kg is added esterifying kettle by handling equipment, in esterifying kettle, add anhydrous methanol 600Kg simultaneously, be that 80/1000 ratio adds hydrogen type cation exchange resin as catalyzer according to the weight ratio of hydrogen type cation exchange resin and rac-Lactide, 80 ℃ of temperature of charge, under the condition of normal pressure, continuously stirring total reflux transesterification reaction 6 hours, the mother liquor that reaction is finished enters surge tank by height pressure difference, by transferpump mother liquor is imported rectifying tower continuously again, control the rectifier bottoms temperature of charge at 145 ℃～150 ℃, 65 ℃ of tower top temperatures, cat head tower bottom pressure difference is 2.0KPa, cat head continues recovery methyl alcohol, continue the overflow heavy constituent at the bottom of the tower, the tower side outlet continues the methyl lactate product, and rectifying finishes, obtain content 99.6% altogether, optical purity is 99.8% methyl lactate 500Kg.The lactoyl methyl lactate that overflows at the bottom of the tower can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.The methyl alcohol that cat head obtains can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.
Example three:
Be that 95% lactic acid 500Kg is conveyed into polycondensation vessel by transferpump with the content of outsourcing, be that 10/10000 ratio adds mixed catalyst in the weight ratio of catalyzer and lactic acid, mixed catalyst is that zinc oxide, stannic oxide and butyl (tetra) titanate are 1: 1: 1 mixture by weight.In 2.5 hours, material is risen to 120 ℃ from 80 ℃, vacuum tightness maintains 5000Pa～4000Pa, entire reaction is carried out having under the condition of stirring, detect the viscosity of lactic acid oligomer by in-line viscometer, according to the viscosity molecular weight contrast relationship, determine that its molecular weight is 2000, polycondensation is finished, by height pressure difference and vacuum pressure reduction lact-acid oligomer is conveyed into the depolymerization still, be that 8/10000 ratio adds mixed catalyst in the weight ratio of catalyzer and lactic acid, mixed catalyst is that zinc oxide, stannic oxide and butyl (tetra) titanate are 1: 1: 1 mixture by weight.Entire reaction is carried out having under the condition of stirring, material is warming up to 190 ℃ rapidly, vacuum tightness maintains 1600Pa, after the rac-Lactide vapor condensation that continues to obtain, and enrichment in holding tank, after depolymerization stops, liquid lactide in the holding tank enters purifying workshop section by transferpump, by the rectification under vacuum purifying technique, obtains refined lactide 320Kg, content reaches 99.8%, and optical purity reaches 99.8%.Again refined lactide 320Kg is added esterifying kettle by handling equipment, in esterifying kettle, add anhydrous methanol 400Kg simultaneously, according to SO
4 2-The weight ratio of the high strong acid of/TiO2 solid and rac-Lactide is that 70/1000 ratio adds SO
4 2-The high strong acid of/TiO2 solid is as catalyzer, 90 ℃ of temperature of charge, under the condition of normal pressure, continuously stirring total reflux transesterification reaction 2.5 hours, the mother liquor that reaction is finished enters surge tank by height pressure difference, by transferpump mother liquor is imported rectifying tower continuously again, control the rectifier bottoms temperature of charge at 140 ℃～145 ℃, 65 ℃ of tower top temperatures, cat head tower bottom pressure difference is 2.0KPa, cat head continues recovery methyl alcohol, continue the overflow heavy constituent at the bottom of the tower, the tower side outlet continues the methyl lactate product, and rectifying finishes, obtain content 99.6% altogether, optical purity is 99.9% methyl lactate 455Kg.The lactoyl methyl lactate that overflows at the bottom of the tower can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.The methyl alcohol that cat head obtains can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.
Example four:
The preparation process of rac-Lactide is with embodiment three, again refined lactide 320Kg is added esterifying kettle by handling equipment, in esterifying kettle, add anhydrous methanol 400Kg simultaneously, be that 50/1000 ratio adds composite catalyst according to the weight ratio of composite catalyst and rac-Lactide, wherein composite catalyst is hydrogen type cation exchange resin and SO
4 2-The high strong acid of/TiO2 solid by weight 1: 1 mixture.90 ℃ of temperature of charge, under the condition of normal pressure, continuously stirring total reflux transesterification reaction 2.5 hours, the mother liquor that reaction is finished enters surge tank by height pressure difference, by transferpump mother liquor is imported rectifying tower continuously again, control rectifier bottoms temperature of charge is at 140 ℃～145 ℃, 65 ℃ of tower top temperatures, cat head tower bottom pressure difference is 2.0KPa, and cat head continues recovery methyl alcohol, continues the overflow heavy constituent at the bottom of the tower, the tower side outlet continues the methyl lactate product, rectifying finishes, and obtains content 99.6% altogether, and optical purity is 99.9% methyl lactate 455Kg.The lactoyl methyl lactate that overflows at the bottom of the tower can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.The methyl alcohol that cat head obtains can return in the synthetic reactor of methyl lactate and participate in the methyl lactate building-up reactions.
Claims (6)
1. a two step method is produced the method for high-content and high-optical-purity methyl lactate, and it may further comprise the steps:
A, lactic acid polycondensation: add catalyzer in lactic acid, the weight ratio of catalyzer and lactic acid is 0.1/10000 ~ 10/10000, carries out polycondensation after adding, and obtains molecular weight at 1000 ~ 2500 lactic acid oligomer;
B, oligopolymer depolymerization: add catalyzer in lactic acid oligomer, the weight ratio of catalyzer and lactic acid oligomer is 0.1/10000 ~ 10/10000, carries out depolymerization reaction after adding, and obtains content in 80% ~ 95% crude product of lactide;
C, rac-Lactide purifying: crude product of lactide is made with extra care, obtain content more than 99.5%, optical purity is in the refined lactide more than 99%;
D, methyl lactate are synthetic: with refined lactide and the ratio adding reactor of anhydrous methanol by weight 1:0.45 ~ 1:2.5, be that 10/1000 ~ 100/1000 ratio adds catalyzer then by weight, under the condition of 50 ~ 150 ℃ of temperature, normal pressure, continuously stirring was carried out total reflux reaction 1 ~ 10 hour, obtained methyl lactate;
E, methyl lactate purifying: what methyl lactate was carried out that purifies and separates adopts is rectification process, and rectifying tower is atmospheric operation or decompression operation; Cat head and tower reactor pressure reduction are 1.5 ~ 3kPa during atmospheric operation, the tower reactor temperature is 140 ℃ ~ 150 ℃, tower top temperature is 65 ℃, the tower side outlet obtains content at the methyl lactate product more than 99.5%, cat head obtains the methyl alcohol of content more than 99.5%, overflows content at the bottom of the tower at the lactoyl methyl lactate more than 99.5%;
Before the lactic acid polycondensation, under vacuum tightness 10000 ~ 500Pa condition, under the condition that distillation temperature is 40 ~ 90 ℃ lactic acid is carried out vacuum distilling earlier, remove free-water wherein; The catalyzer that adds in lactic acid polycondensation and oligopolymer depolymerization is at least a in zinc class catalyzer, tin class catalyzer or the organic catalyst; The catalyzer that adds in methyl lactate is synthetic is one or both in exchange resin or the high strong acid catalyst of solid, and the weight ratio of its adding is 10/1000 ~ 100/1000.
2. two step method according to claim 1 is produced the method for high-content and high-optical-purity methyl lactate, and wherein: the catalyzer that adds in lactic acid polycondensation and oligopolymer depolymerization is one or more the composite catalyst in zinc lactate, zinc oxide, zinc powder, zinc ethyl, lactic acid tin, stannic oxide, tindioxide, tin protoxide, the inferior tin of lactic acid, stannous octoate, tin protochloride, glass putty or the butyl (tetra) titanate.
3. two step method according to claim 1 is produced the method for high-content and high-optical-purity methyl lactate, and wherein: the catalyzer that adds in methyl lactate is synthetic is hydrogen type cation exchange resin or SO
4 2-The composite catalyst of one or both in the high strong acid catalyst of/TiO2 solid.
4. two step method according to claim 1 is produced the method for high-content and high-optical-purity methyl lactate, it is characterized in that: the method for among the step C crude product of lactide being made with extra care is recrystallization, rectification under vacuum or fusion-crystallization, or two kinds and two or more combinations in the above-mentioned process for purification.
5. two step method according to claim 1 is produced the method for high-content and high-optical-purity methyl lactate, wherein: the lactoyl methyl lactate that overflows at the bottom of the rectifying Tata is returned in the reactor of step D and participate in the methyl lactate building-up reactions.
6. two step method according to claim 1 is produced the method for high-content and high-optical-purity methyl lactate, and wherein: the recovery methyl alcohol that the rectifying tower cat head is obtained returns in the reactor of step D and participates in the methyl lactate building-up reactions.
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| WO2013159347A1 (en) * | 2012-04-27 | 2013-10-31 | 孝感市易生新材料有限公司 | Method for continuously producing high-content high-optical-purity lactate |
| CN102675103A (en) * | 2012-04-27 | 2012-09-19 | 孝感市易生新材料有限公司 | Method for producing menthyl lactate with high content and high optical purity by using two-step method |
| CN102675102A (en) * | 2012-04-27 | 2012-09-19 | 孝感市易生新材料有限公司 | Continuous production method of high-content high-optical-purity lactate |
| CN111269158A (en) * | 2020-03-11 | 2020-06-12 | 西安玄德医药科技有限公司 | Preparation method of α -hydroxy acid ester compound |
| CN115232102B (en) * | 2022-09-06 | 2024-02-13 | 中国科学院长春应用化学研究所 | Preparation method and production device of lactide |
| CN115504958B (en) * | 2022-10-20 | 2023-12-19 | 山东寿光巨能金玉米开发有限公司 | Method for joint production of lactide and lactate |
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| CN1450046A (en) * | 2002-04-05 | 2003-10-22 | 中国科学院大连化学物理研究所 | Method for synthesizing high-recovery and high-optical purity L-butyl lactate |
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