CN113603671A - Method for improving yield of lactide - Google Patents
Method for improving yield of lactide Download PDFInfo
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- CN113603671A CN113603671A CN202110931111.4A CN202110931111A CN113603671A CN 113603671 A CN113603671 A CN 113603671A CN 202110931111 A CN202110931111 A CN 202110931111A CN 113603671 A CN113603671 A CN 113603671A
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- yield
- lactide
- crude product
- filter cake
- improving
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- 238000000034 method Methods 0.000 title claims abstract description 36
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000012065 filter cake Substances 0.000 claims abstract description 23
- 239000012043 crude product Substances 0.000 claims abstract description 20
- 238000001953 recrystallisation Methods 0.000 claims abstract description 17
- 239000000047 product Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000004537 pulping Methods 0.000 claims abstract description 14
- 238000005406 washing Methods 0.000 claims abstract description 14
- 150000001261 hydroxy acids Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 16
- 239000000706 filtrate Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 238000002390 rotary evaporation Methods 0.000 claims description 9
- 238000000967 suction filtration Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 5
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 abstract description 8
- 238000006297 dehydration reaction Methods 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000003763 carbonization Methods 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 20
- 235000014655 lactic acid Nutrition 0.000 description 10
- 239000004310 lactic acid Substances 0.000 description 10
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 7
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920000747 poly(lactic acid) Polymers 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical compound CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 206010057040 Temperature intolerance Diseases 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000008543 heat sensitivity Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for improving lactide yield, namely, after an oligomer is generated by esterification and dehydration of hydroxy acid, a high-boiling-point solvent is added, and then depolymerization is carried out; and (3) before recrystallization, washing, pulping and filtering the crude product, and recrystallizing the filter cake once again to obtain the high-purity product. The method reduces carbonization in the depolymerization process, improves the conversion rate, reduces the recrystallization times, and maximally improves the utilization rate and the yield of the raw materials.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for improving lactide yield.
Background
The lactide is ester formed by interactive condensation of two molecules of alpha-hydroxy acid inner hydroxyl (-OH) and carboxyl (-COOH) to remove two molecules of water, and is a six-atom heterocyclic compound. Glycolic acid (α -glycolic acid) and lactic acid (α -hydroxypropionic acid) can be heated to give glycolide and lactide, respectively. Polylactide and polyglycolide and related materials polymerized from the lactide have good biodegradability, biocompatibility and mechanical strength, are ideal biodegradable materials, and have wide application prospects in the aspects of human tissue repair, wound suture and controlled release of medicines and pesticides.
The lactide as the intermediate material of polylactide has the characteristics of high boiling point, low freezing point, heat sensitivity, easy water absorption, ring-opening reaction and the like, has high refining and purification difficulty, and is the main technical difficulty of a synthesis process; the preparation cost and purity of the polylactide modified by the modified starch are determined by the cost and quality of the high-molecular-weight polylactide, and are also one of the main factors influencing the industrialization of the polylactide.
The synthesis process of lactide mainly comprises two stages of reaction synthesis and refining purification. The reaction stage is that hydroxy acid is esterified and dehydrated to generate oligomer (molecular weight is 500-. These impurities can affect the molecular weight, molecular weight distribution, and stability and mechanical properties of the polymer in the next step. Therefore, the crude product is purified and refined to the polymerization level. The prior lactide refining method comprises the following steps: among them, the solvent absorption method, the gas-assisted evaporation method, the recrystallization method and the like are most frequently used, and a method of repeatedly recrystallizing glycolide using an organic solvent such as an alcohol or ethyl acetate is more common, and purification of glycolide by recrystallization is reported in, for example, patent US5223630, CN100999516 and the like. The above method mainly has the following problems: on one hand, when the oligomer generated by esterification and dehydration in the lactide synthesis process is subjected to pyrolysis, the reaction liquid is gradually viscous, darkens in color and even carbonizes with the increase of the temperature (higher than 200 ℃), so that the distillation is not easy to occur, and the yield is reduced. On the other hand, the purification and purification process of lactide generally adopts a repeated recrystallization method, and the amount of used solvent is large, so that the product loss is also large, and the yield is also low.
Therefore, how to improve the synthesis process of lactide, increase the yield and reduce the production cost becomes a hot topic of research.
Disclosure of Invention
Aiming at the problems, the invention provides a method for improving the yield of lactide, which reduces carbonization in the depolymerization process, improves the conversion rate, reduces the recrystallization times, and improves the utilization rate and the yield of raw materials to the maximum extent.
The method for improving the yield of the lactide is characterized in that after the hydroxy acid is esterified and dehydrated to generate oligomer, a high-boiling-point solvent is added, and then depolymerization is carried out; and (3) before recrystallization, washing, pulping and filtering the crude product, and recrystallizing the filter cake once again to obtain the high-purity product.
Furthermore, after water and low-boiling-point impurities in the filtrate are removed by rotary evaporation, the hydroxy acid in the filtrate is collected for reuse, and the utilization rate of the raw materials is improved to the maximum extent.
The high boiling point solvent is selected from glycerol or cetyl alcohol or stearyl alcohol or ethylene glycol.
The mass ratio of the high-boiling-point solvent to the hydroxy acid is as follows: 0.5-1:1, preferably 0.7: 1.
The mass ratio of water to the crude product in the washing, pulping and suction filtration processes is 1-3:1, preferably 2.5: 1.
The rotary evaporation temperature of the filtrate is 60-100 ℃, and the preferable temperature is 70-80 ℃.
The solvent adopted in the recrystallization process is ethyl acetate, and the mass ratio of the ethyl acetate to the filter cake is 1-2.5:1, preferably 1.5-2: 1.
The method comprises the following more specific steps:
(1) adding hydroxy acid into a reaction bottle, distilling under reduced pressure to 180 ℃, adding a catalyst and a high-boiling point solvent, stirring and mixing uniformly, depolymerizing at high temperature and in high vacuum, collecting a crude product until no product is distilled off to obtain a crude product I, adding water into the crude product I, pulping, washing and filtering to obtain a filter cake I and a filtrate I;
(2) carrying out rotary distillation on the filtrate I until the volume is not reduced, carrying out reduced pressure distillation on the residues to 180 ℃, depolymerizing at high temperature and in high vacuum, collecting the crude product until no product is distilled off to obtain a crude product II, adding water into the crude product II, pulping, washing and carrying out suction filtration to obtain a filter cake II;
(3) and mixing the filter cake I and the filter cake II, adding ethyl acetate for recrystallization once, and drying in vacuum to obtain the product.
The high temperature is 230-250 ℃.
The high vacuum is-0.1 MPa.
The invention has the following beneficial effects:
(1) according to the invention, after the hydroxy acid is esterified and dehydrated to generate the oligomer, the high-boiling-point solvent is added firstly, and then depolymerization is carried out, so that carbonization in the depolymerization process is reduced, the conversion rate is improved, and the problem of low yield caused by incomplete distillation is avoided.
(2) The crude product is washed, pulped and filtered before recrystallization, and a high-purity product can be obtained by carrying out primary recrystallization on a filter cake, so that the problems of large solvent consumption, large product loss and low yield caused by a repeated recrystallization method are solved.
(3) And (3) after removing water and low-boiling-point impurities by rotary evaporation, collecting hydroxy acid in the filtrate for reuse, and maximally improving the utilization rate of the raw materials.
Detailed Description
Example 1
Weighing 500g of lactic acid, adding the lactic acid into a three-neck flask, carrying out reduced pressure distillation dehydration to 150 ℃, adding a proper amount of catalyst and 350g of glycerol, stirring and mixing uniformly, carrying out high-temperature (230-;
and (3) carrying out rotary evaporation on the filtrate for 2 hours at the temperature of 80 ℃ until the volume is not reduced, removing most of water and other low-boiling-point impurities, repeating the steps of reduced pressure distillation, high-temperature depolymerization, water adding pulping, washing and suction filtration to obtain 220g of crude filter cake, mixing the two filter cakes, adding 1200ml of ethyl acetate to recrystallize once, and carrying out vacuum drying at the temperature of 40 ℃ for 48 hours to obtain 395g of lactide, wherein the yield is 79%, and the purity is 99.97% by detection.
Example 2
Weighing 500g of glycolic acid, adding the glycolic acid into a three-neck flask, carrying out reduced pressure distillation dehydration to 180 ℃, adding a proper amount of catalyst and 400g of hexadecanol, stirring and mixing uniformly, carrying out high-vacuum depolymerization at high temperature (250-270 ℃), collecting crude glycolide until no product is distilled to obtain 530g of crude glycolide, adding 530ml of water into the crude glycolide, pulping, washing and carrying out suction filtration to obtain 460g of filter cake and 850ml of filtrate;
and (3) carrying out rotary evaporation on the filtrate for 2 hours at the temperature of 80 ℃ until the volume is not reduced, removing most of water and other low-boiling-point impurities, repeating the steps of reduced pressure distillation, high-temperature depolymerization, water adding pulping, washing and suction filtration to obtain 200g of crude filter cake, mixing the two filter cakes, adding 660ml of ethyl acetate to recrystallize once, and carrying out vacuum drying at the temperature of 40 ℃ for 48 hours to obtain 375g of lactide, wherein the yield is 75%, and the purity is 99.95% by detection.
Example 3
Weighing 1000g of lactic acid, adding the lactic acid into a three-neck flask, carrying out reduced pressure distillation dehydration to 150 ℃, adding a proper amount of catalyst and 500g of octadecanol, stirring and mixing uniformly, carrying out high-temperature (190-;
and (3) carrying out rotary evaporation on the filtrate at the temperature of 80 ℃ for 3.5h until the volume is not reduced, removing most of water and other low-boiling-point impurities, repeating the steps of reduced pressure distillation, high-temperature depolymerization, pulping by adding water, washing and suction filtration to obtain 450g of crude filter cake, mixing the two filter cakes, adding 2800ml of ethyl acetate to recrystallize once, and carrying out vacuum drying at the temperature of 40 ℃ for 48 hours to obtain 780g of lactide, wherein the yield is 78%, and the purity is 99.93% by detection.
Example 4
Weighing 1000g of lactic acid, adding the lactic acid into a three-neck flask, carrying out reduced pressure distillation dehydration to 150 ℃, adding a proper amount of catalyst and 1000g of octadecanol, stirring and mixing uniformly, carrying out high-vacuum depolymerization at high temperature (190-;
and (3) carrying out rotary evaporation on the filtrate for 4 hours at the temperature of 80 ℃ until the volume is not reduced, removing most of water and other low-boiling-point impurities, repeating the steps of reduced pressure distillation, high-temperature depolymerization, pulping by adding water, washing and suction filtration to obtain 440g of crude filter cake, mixing the two filter cakes, adding 3420ml of ethyl acetate to recrystallize once, and carrying out vacuum drying at the temperature of 40 ℃ for 48 hours to obtain 710g of lactide, wherein the yield is 71%, and the purity is 99.95% by detection.
Comparative example 1
Weighing 500g of lactic acid, adding the lactic acid into a three-neck flask, carrying out reduced pressure distillation dehydration to 150 ℃, adding a proper amount of catalyst, stirring and mixing uniformly, carrying out high-temperature (230 ℃) and high-vacuum depolymerization, collecting a crude lactide product until no product is distilled off to obtain 500g of the crude product, adding 800ml of ethyl acetate for recrystallization, repeating the steps for 4 times, and carrying out vacuum drying at 40 ℃ for 48 hours to obtain 178g of lactide, wherein the yield is 35.6%, and the purity is 99.52% through detection.
Comparative example 2
Weighing 1000g of lactic acid, adding the lactic acid into a three-neck flask, carrying out reduced pressure distillation dehydration to 150 ℃, adding a proper amount of catalyst, stirring and mixing uniformly, carrying out high temperature (230 ℃.) -250 ℃ C., high vacuum depolymerization, collecting crude lactide until no product is distilled off to obtain 1200g of crude lactide, adding 2400ml of ethyl acetate for recrystallization, repeating the steps for 4 times, and carrying out vacuum drying at 40 ℃ for 48 hours to obtain 382g of lactide, wherein the yield is 38.2%, and the purity is 99.65% through detection.
Claims (10)
1. A method for improving lactide yield is characterized in that after hydroxy acid is esterified and dehydrated to generate oligomer, a high-boiling-point solvent is added, and then depolymerization is carried out; and (3) before recrystallization, washing, pulping and filtering the crude product, and recrystallizing the filter cake once again to obtain the high-purity product.
2. The method for improving the yield of lactide according to claim 1, wherein the hydroxy acid in the filtrate is collected for reuse after removing water and low boiling point impurities by rotary evaporation.
3. A method for increasing yield of lactide as claimed in claim 1, wherein the high boiling point solvent is selected from glycerol or cetyl alcohol or stearyl alcohol or ethylene glycol.
4. The method for improving the yield of lactide according to claim 1, wherein the mass ratio of the high-boiling point solvent to the hydroxy acid is: 0.5-1:1.
5. The method for improving the yield of lactide according to claim 1, wherein the mass ratio of water to crude product in the processes of water washing, pulping and suction filtration is 1-3: 1.
6. A method for increasing yield of lactide as claimed in claim 2, wherein the rotary evaporation temperature of the filtrate is 60-100 ℃.
7. The method for improving the yield of lactide according to claim 1, wherein the solvent used in the recrystallization process is ethyl acetate, and the mass ratio of the ethyl acetate to the filter cake is 1-2.5: 1.
8. The method for improving the yield of lactide according to claim 1, characterized by comprising the following steps:
(1) adding hydroxy acid into a reaction bottle, distilling under reduced pressure to 180 ℃, adding a catalyst and a high-boiling point solvent, stirring and mixing uniformly, depolymerizing at high temperature and in high vacuum, collecting a crude product until no product is distilled off to obtain a crude product I, adding water into the crude product I, pulping, washing and filtering to obtain a filter cake I and a filtrate I;
(2) carrying out rotary distillation on the filtrate I until the volume is not reduced, carrying out reduced pressure distillation on the residues to 180 ℃, depolymerizing at high temperature and in high vacuum, collecting the crude product until no product is distilled off to obtain a crude product II, adding water into the crude product II, pulping, washing and carrying out suction filtration to obtain a filter cake II;
(3) and mixing the filter cake I and the filter cake II, adding ethyl acetate for recrystallization once, and drying in vacuum to obtain the product.
9. A method for increasing the yield of lactide according to claim 8, wherein the high temperature is 230 ℃ and 250 ℃.
10. A method for increasing yield of lactide as claimed in claim 8, wherein the high vacuum is-0.1 MPa.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110931111.4A CN113603671A (en) | 2021-08-13 | 2021-08-13 | Method for improving yield of lactide |
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| CN202110931111.4A CN113603671A (en) | 2021-08-13 | 2021-08-13 | Method for improving yield of lactide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115124501A (en) * | 2022-08-30 | 2022-09-30 | 深圳市迈启生物材料有限公司 | Method and device for preparing glycolide |
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Cited By (2)
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| CN115124501A (en) * | 2022-08-30 | 2022-09-30 | 深圳市迈启生物材料有限公司 | Method and device for preparing glycolide |
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