CN101768141A - Method for preparing alpha-acetyl-gamma-butyrolactone - Google Patents
Method for preparing alpha-acetyl-gamma-butyrolactone Download PDFInfo
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- CN101768141A CN101768141A CN201010033349A CN201010033349A CN101768141A CN 101768141 A CN101768141 A CN 101768141A CN 201010033349 A CN201010033349 A CN 201010033349A CN 201010033349 A CN201010033349 A CN 201010033349A CN 101768141 A CN101768141 A CN 101768141A
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- butyrolactone
- gamma
- catalyzer
- add
- toluene
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- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title abstract description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 54
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 30
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 12
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 9
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000005917 acylation reaction Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 239000006227 byproduct Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- -1 α-ethanoyl Chemical group 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 3
- 238000010926 purge Methods 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 238000005191 phase separation Methods 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims description 2
- 230000000007 visual effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 9
- 238000003912 environmental pollution Methods 0.000 abstract description 8
- 230000008901 benefit Effects 0.000 abstract description 4
- 229910052708 sodium Inorganic materials 0.000 abstract description 3
- 239000011734 sodium Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000012345 acetylating agent Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000002485 combustion reaction Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 4
- 150000003016 phosphoric acids Chemical class 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Abstract
The invention provides a method for preparing alpha-acetyl-gamma-butyrolactone. In the method, gamma-butyrolactone and an acetylating agent (ethyl acetate and methyl acetate or a mixture of ethyl acetate and methyl acetate) are used as starting materials, metal sodium is used as a catalyst, and the product is obtained by acylation, neutralization and distillation. The method has the advantages that: the raw materials are used as the solvent at an initial stage of the reaction, so that the environmental pollution brought by the solvent is lowered, the material feeding amount is increased, the production efficiency is improved, and the production cost is lowered; the metal sodium is added into the reaction system continuously or for several times, so that potential safety risks such as outshoot and combustion caused by difficult control of the reaction speed can be effectively avoided when the sodium metal is reacted at a melting temperature; and by adopting the pressure-regulating distillation method, the byproducts are effectively recovered, the environmental pollution is lowered, and the comprehensive economic benefits are improved.
Description
Technical field
The present invention relates to medicine, chemical intermediate, specifically is the preparation method of a kind of α-ethanoyl-gamma-butyrolactone.
Background technology
α-ethanoyl-gamma-butyrolactone is a kind of important medicine and organic chemical industry's intermediate or raw material, especially as the production VITMAIN B1, prolong the intermediate of medicines such as pained and chloroquine.At present, the method for preparing α-ethanoyl-gamma-butyrolactone mainly contains two kinds of routes, and the first is the technology of starting raw material with oxyethane and methyl aceto acetate, and it two is to be the technology of starting raw material with gamma-butyrolactone and ethyl acetate.
US 2443827, CN 135745A, GB 740993, Czechoslovakia's patent 95116, clear 4212662 communiques of secret service have all adopted with oxyethane is the synthesis technique of raw material; but the oxyethane as reaction raw materials belongs to the inflammable and explosive chemical substance of one-level; in accumulating and reaction process, all exist serious potential safety hazard, also be difficult to obtain simultaneously the higher α-ethanoyl of purity-gamma-butyrolactone.
With gamma-butyrolactone and ethyl acetate is the synthesis technique of starting raw material, is solvent with the benzene-like compounds generally, and in the presence of basic metal, the mixed solution that drips gamma-butyrolactone and ethyl acetate reacts.As: CN 101230054A at first adds sodium Metal 99.5, and under the sodium Metal 99.5 molten state, drips gamma-butyrolactone and ethyl acetate mixed solution and react in benzene kind solvent.Because sodium Metal 99.5 is disposable adding, initial reaction stage is carried out under comparatively high temps again, reaction is violent, charging capacity can not running at full capacity, the equipment utilization rate variance, production efficiency is low, however, often occur in the production process towards material, burning and explosive incident, for eliminating this potential safety hazard, patent CN 1548427A report, on the basic basis of invariable of above-mentioned reaction conditions, increase the pool of buffer reflux, but charging capacity still can not running at full capacity, and fail thoroughly to avoid potential safety hazard to take place and benzene kind solvent to the pollution of environment.It is raw material with gamma-butyrolactone and acetic ester that U.S. Pat 5789603 reported a kind of, sodium alkoxide is a catalyzer, corresponding acetic ester or benzene-like compounds are the method for solvent, though avoided the problems referred to above, but its reaction will be carried out in high-pressure reactor, it is had relatively high expectations to reaction unit, and the safety coefficient of operation is also lower.Patent CN 101092407A, openly reported a kind of in the fixed-bed reactor that the load-type solid fluoride catalysts is housed, feed the gamma-butyrolactone of gasification and the method that ethyl acetate is reacted continuously, but this production process, energy consumption is bigger, simultaneously, use the solid alkali fluorochemical to make catalyzer, there are certain hidden danger in product, environmental pollution.
Summary of the invention
The object of the present invention is to provide a kind of reaction temperature and, the preparation method of security is good, production efficiency is high, environmental pollution is little, production cost is low, product yield is high, purity is high α-ethanoyl-gamma-butyrolactone.
The present invention for achieving the above object; the method for preparing α-ethanoyl-gamma-butyrolactone is: with gamma-butyrolactone and acetylizing agent (ethyl acetate, methyl acetate or both mixtures) is starting raw material; sodium Metal 99.5 is made catalyzer, through acidylate, neutralization and distill product.It is characterized in that: the acylation reaction initial stage is made solvent with raw material, has reduced the environmental pollution that solvent brings, and has increased charging capacity, has improved production efficiency, has reduced production cost; Sodium Metal 99.5 gradation or add reaction system continuously, that has effectively avoided reaction under the sodium Metal 99.5 melt temperature to cause speed of response to be difficult to control causing dashes potential safety hazards such as material, burning; Adopt pressure regulation distillatory method, by product has obtained efficient recovery, has reduced environmental pollution, has improved overall economic efficiency.Specifically comprise the steps:
(1) earlier the acylation reaction device is vacuumized, again through nitrogen purging, gamma-butyrolactone that disposable then adding mixes in advance and acetylizing agent mixed solution, under nitrogen atmosphere, stir, heat up, add the 1/5-3/5 of required catalyzer total amount simultaneously, after the system for the treatment of refluxes, stop logical nitrogen;
(2) in the system of completing steps (1), add remaining catalyzer in batches or continuously, add speed visual response speed and decide, do not dash with reacting balance and expect to be as the criterion; After treating that catalyzer adds, under the system reflux temperature, insulation 2～10h;
The add-on of gamma-butyrolactone, acetylizing agent and catalyzer is calculated in molar ratio as 1: 1.2～1.9: 1.0～1.2 in step (1) and (2);
(3) after acylation reaction finished, material changed neutralization reactor over to, and under agitation with the phosphoric acid neutralization, control pH value is between 3～5; Leave standstill after the neutralization, organic phase and aqueous phase separation, water extracts through toluene, merges organic phase; Organic phase reclaims by product ethanol and extracts through the normal pressure distillation uses toluene, and underpressure distillation gets product again; The add-on of phosphoric acid and toluene wherein, the mol ratio 1: 1.0～1.2: 0.5～1.2 of pressing gamma-butyrolactone, phosphoric acid, toluene adds.
Described acetylizing agent is ethyl acetate, methyl acetate or both mixtures; Described catalyzer is a sodium Metal 99.5.
The present invention compares, has the following advantages with existing α-ethanoyl-gamma-butyrolactone preparation method:
1, acylation reaction is carried out under solvent-free situation, has both accelerated speed of response, has reduced production cost again, has reduced the environmental pollution that solvent brings, and has increased charging capacity simultaneously, and production efficiency has improved 0.5 times.
2, catalyzer adds in batches or continuously, has avoided reacting under the sodium Metal 99.5 melt temperature, and what cause speed of response to be difficult to control to cause dashes potential safety hazards such as material, burning.Also avoided simultaneously the disposable adding caking of sodium Metal 99.5 to make the problem of reaction times lengthening.
3, adopt the method for pressure regulation distillation (reducing pressure behind the first normal pressure), by product has obtained efficient recovery, has reduced environmental pollution, has improved overall economic efficiency.
4, adopt phosphoric acid to neutralize, make neutralization reaction milder, be convenient to operation and control, the by product phosphoric acid salt of generation is easy to reclaim.So not only eliminated the pollution of waste water, and by product also can be created good economic benefit to environment.
Specific embodiments
Embodiment 1:
The acetylizing agent that present embodiment uses is ethyl acetate.Acylation reaction device (5L) vacuumizes, and again through nitrogen purging, adds 1232g gamma-butyrolactone, 1894g ethyl acetate and 100g sodium Metal 99.5 then, begins to stir, heat up, and after the system for the treatment of refluxes, stops logical nitrogen.Under the system reflux state, add the 280g sodium Metal 99.5 continuously, the speed that adds sodium Metal 99.5 steadily is advisable to keep reaction system.Finish, continue insulation reaction 8h.Be cooled to 30 ℃, stir and to add 51% the about 2930g of phosphoric acid solution down gradually, be neutralized between the system pH 3-4 till.Neutralization is finished, and standing demix is told organic phase, and water with the extraction of 433g toluene once merges organic phase.First then normal pressure (71 ℃-90 ℃) steams light constituent, and back underpressure distillation is collected product and got 1704.0g, and product purity is greater than 99.1%, and productive rate has reached 92.3%.Water after the extraction is through dewatering to such an extent that phosphoric acid salt 1870 restrains.
Embodiment 2:
The acetylizing agent that present embodiment uses is methyl acetate.The 1894g ethyl acetate, all the other steps are all identical with embodiment 1 in acetylizing agent usefulness 1595g methyl acetate replacement embodiment 1.Get product 1663.6g, product purity is greater than 99.2%, and productive rate has reached 90.0%.Water after the extraction is through dewatering to such an extent that phosphoric acid salt 1878 restrains.
Embodiment 3:
The acetylizing agent that present embodiment uses is the mixed ester of ethyl acetate and methyl acetate.The 1894g ethyl acetate, all the other steps are all identical with embodiment 1 in acetylizing agent usefulness 947g ethyl acetate and 797g methyl acetate replacement embodiment 1.Get product 1674.5g, product purity is greater than 99.1%, and productive rate has reached 90.5%.Water after the extraction is through dewatering to such an extent that phosphoric acid salt 1875 restrains.
Claims (3)
1. the preparation method of α-ethanoyl-gamma-butyrolactone is characterized in that following steps:
(1) earlier the acylation reaction device is vacuumized, again through nitrogen purging, gamma-butyrolactone that disposable then adding mixes in advance and acetylizing agent mixed solution, under nitrogen atmosphere, stir, heat up, add the 1/5-3/5 of required catalyzer total amount simultaneously, after the system for the treatment of refluxes, stop logical nitrogen;
(2) in the system of completing steps (1), add remaining catalyzer in batches or continuously, add speed visual response speed and decide, do not dash with reacting balance and expect to be as the criterion; After treating that catalyzer adds, under the system reflux temperature, insulation 2～10h;
The add-on of gamma-butyrolactone, acetylizing agent and catalyzer is calculated in molar ratio as 1: 1.2～1.9: 1.0～1.2 in step (1) and (2);
(3) after acylation reaction finished, material changed neutralization reactor over to, and under agitation with the phosphoric acid neutralization, control pH value is between 3～5; Leave standstill after the neutralization, organic phase and aqueous phase separation, water extracts through toluene, merges organic phase; Organic phase reclaims by product ethanol and extracts through the normal pressure distillation uses toluene, and underpressure distillation gets product again; The add-on of phosphoric acid and toluene wherein, the mol ratio 1: 1.0～1.2: 0.5～1.2 of pressing gamma-butyrolactone, phosphoric acid, toluene adds.
2. the preparation method of α-ethanoyl as claimed in claim 1-gamma-butyrolactone is characterized in that, described acetylizing agent is ethyl acetate, methyl acetate or both mixtures.
3. the preparation method of α-ethanoyl as claimed in claim 1-gamma-butyrolactone is characterized in that described catalyzer is a sodium Metal 99.5.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2010100333497A CN101768141B (en) | 2010-01-05 | 2010-01-05 | Method for preparing alpha-acetyl-gamma-butyrolactone |
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| CN2010100333497A CN101768141B (en) | 2010-01-05 | 2010-01-05 | Method for preparing alpha-acetyl-gamma-butyrolactone |
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| CN101768141A true CN101768141A (en) | 2010-07-07 |
| CN101768141B CN101768141B (en) | 2011-12-07 |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102030729A (en) * | 2010-11-04 | 2011-04-27 | 山西大学 | Preparation method of alpha-acetyl-gamma-butyrolactone |
| CN102229586A (en) * | 2011-05-13 | 2011-11-02 | 山西三维集团股份有限公司 | Preparation method for alpha-acetyl-gamma-butyrolactone |
| CN102617520A (en) * | 2012-03-06 | 2012-08-01 | 山西大学 | Process for preparing alpha-acetyl-gamma-butyrolactone for co-production of various phosphates |
| CN102992930A (en) * | 2012-12-15 | 2013-03-27 | 福州大学 | Recovery process and separation device of toluene solvent in production process of alpha-acetyl-gamma butyrolactone |
| CN108129423A (en) * | 2018-02-09 | 2018-06-08 | 东北制药集团股份有限公司 | A kind of method for preparing α-acetyl-gamma-butyrolacton |
| CN109111337A (en) * | 2018-10-31 | 2019-01-01 | 福建师范大学福清分校 | A kind of separation equipment and method containing mixed solvents such as toluene, ethyl acetate and ethyl alcohol |
| CN110804031A (en) * | 2019-12-13 | 2020-02-18 | 浙江联盛化学股份有限公司 | Synthesis method of α -acetyl-gamma-butyrolactone |
| CN111018810A (en) * | 2019-12-13 | 2020-04-17 | 浙江联盛化学股份有限公司 | Device and method for continuously producing α -acetyl-gamma-butyrolactone |
| CN114835661A (en) * | 2022-05-07 | 2022-08-02 | 南京杰运医药科技有限公司 | Industrial preparation method of a-acetyl-r-butyrolactone |
| CN115417838A (en) * | 2022-08-16 | 2022-12-02 | 上海博纳赛恩医药研发有限公司 | Process for preparing alpha-acetyl-gamma-butyrolactone |
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| CN107857745A (en) * | 2017-12-12 | 2018-03-30 | 安徽国星生物化学有限公司 | A kind of synthetic method of α acetyl group gamma butyrolactone |
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- 2010-01-05 CN CN2010100333497A patent/CN101768141B/en not_active Expired - Fee Related
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102030729A (en) * | 2010-11-04 | 2011-04-27 | 山西大学 | Preparation method of alpha-acetyl-gamma-butyrolactone |
| CN102030729B (en) * | 2010-11-04 | 2012-05-23 | 山西大学 | Preparation method of alpha-acetyl-gamma-butyrolactone |
| CN102229586A (en) * | 2011-05-13 | 2011-11-02 | 山西三维集团股份有限公司 | Preparation method for alpha-acetyl-gamma-butyrolactone |
| CN102617520A (en) * | 2012-03-06 | 2012-08-01 | 山西大学 | Process for preparing alpha-acetyl-gamma-butyrolactone for co-production of various phosphates |
| CN102992930A (en) * | 2012-12-15 | 2013-03-27 | 福州大学 | Recovery process and separation device of toluene solvent in production process of alpha-acetyl-gamma butyrolactone |
| CN102992930B (en) * | 2012-12-15 | 2014-12-31 | 福州大学 | Recovery process and separation device of toluene solvent in production process of alpha-acetyl-gamma butyrolactone |
| CN108129423A (en) * | 2018-02-09 | 2018-06-08 | 东北制药集团股份有限公司 | A kind of method for preparing α-acetyl-gamma-butyrolacton |
| CN109111337A (en) * | 2018-10-31 | 2019-01-01 | 福建师范大学福清分校 | A kind of separation equipment and method containing mixed solvents such as toluene, ethyl acetate and ethyl alcohol |
| CN109111337B (en) * | 2018-10-31 | 2024-04-09 | 福建技术师范学院 | Separation equipment and method for mixed solvent containing toluene, ethyl acetate, ethanol and the like |
| CN110804031A (en) * | 2019-12-13 | 2020-02-18 | 浙江联盛化学股份有限公司 | Synthesis method of α -acetyl-gamma-butyrolactone |
| CN111018810A (en) * | 2019-12-13 | 2020-04-17 | 浙江联盛化学股份有限公司 | Device and method for continuously producing α -acetyl-gamma-butyrolactone |
| CN110804031B (en) * | 2019-12-13 | 2021-09-14 | 浙江联盛化学股份有限公司 | Synthetic method of alpha-acetyl-gamma-butyrolactone |
| CN111018810B (en) * | 2019-12-13 | 2021-09-14 | 浙江联盛化学股份有限公司 | Device and method for continuously producing alpha-acetyl-gamma-butyrolactone |
| CN114835661A (en) * | 2022-05-07 | 2022-08-02 | 南京杰运医药科技有限公司 | Industrial preparation method of a-acetyl-r-butyrolactone |
| CN115417838A (en) * | 2022-08-16 | 2022-12-02 | 上海博纳赛恩医药研发有限公司 | Process for preparing alpha-acetyl-gamma-butyrolactone |
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| CN101768141B (en) | 2011-12-07 |
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