CN1032855C - new process for producing ethyl lactate - Google Patents
new process for producing ethyl lactate Download PDFInfo
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- CN1032855C CN1032855C CN 93118797 CN93118797A CN1032855C CN 1032855 C CN1032855 C CN 1032855C CN 93118797 CN93118797 CN 93118797 CN 93118797 A CN93118797 A CN 93118797A CN 1032855 C CN1032855 C CN 1032855C
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- Prior art keywords
- ethyl lactate
- lactic acid
- ethanol
- esterification
- acid
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 229940116333 ethyl lactate Drugs 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 87
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 43
- 230000032050 esterification Effects 0.000 claims abstract description 21
- 238000005886 esterification reaction Methods 0.000 claims abstract description 21
- 239000004310 lactic acid Substances 0.000 claims abstract description 20
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 20
- 238000010992 reflux Methods 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 229960004756 ethanol Drugs 0.000 claims description 24
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000010025 steaming Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229940045641 monobasic sodium phosphate Drugs 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 238000005516 engineering process Methods 0.000 abstract description 8
- 235000013305 food Nutrition 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 2
- 235000013599 spices Nutrition 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OSWRVYBYIGOAEZ-UHFFFAOYSA-N acetic acid;2-hydroxypropanoic acid Chemical compound CC(O)=O.CC(O)C(O)=O OSWRVYBYIGOAEZ-UHFFFAOYSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing ethyl lactate from lactic acid and alcohol includes such steps as full-reflux esterification, dewatering esterification of absolute alcohol, recovering alcohol and vacuum rectification. The invention has mature technology and stable operation, and the yield of the lactic acid reaches 97.2 percent. Compared with the prior art. The invention has the advantages of low raw material consumption, low production cost, large equipment production capacity, good product quality and the like. The invention is suitable for the production of ethyl lactate with various purposes such as essence, food, wine brewing, solvent and the like, and is particularly suitable for the production of edible spice grade ethyl lactate.
Description
The present invention relates to the production technique of ethyl lactate, particularly the production technique of flavouring agent level ethyl lactate.
Ethyl lactate claims ethyl again, and colourless transparent liquid has soft fruital, 154 ℃ of boiling points, and relative density (25/25 ℃) 1.030, refractive index (20 ℃) 1.4124 dissolves each other fully with water and part is decomposed, and is soluble in alcohol, ether, ketone and ester class.It is industrial having been widely used such as essence, food, wine brewing, solvents.
U.S. chemical abstract (C.A.), World Patent Index (WPI) and world patent abstract (WPA) before the present invention makes, still find no the production technique similar to the present invention by retrieval.
About the more representational document of ethyl lactate production technique, as: " (" Fenaroli spices handbook third part " synthetic perfume " is turned over Ze Ben to the synthetic flavor handbook in the U.S..Jinan City light industry institute compiling, light industry press, September in 1985 the 1st edition, 597 pages) in introduced the synthetic method of ethyl lactate: lactic acid and ethanol react in benzole soln and prepare in the presence of the vitriol oil or chlorsulfonic acid or Phenylsulfonic acid.
The most technology that adopts traditional sulphuric acid catalysis, benzene dehydration esterification of present domestic ethyl lactate manufacturer.This technology is summarized as follows: lactic acid (content 80%) and ethanol (92～93%) are pressed a certain proportion ingredient, add the vitriol oil as catalyzer, add a large amount of benzene as dewatering agent, then in esterifying kettle (tower) internal heating backflow esterification, form ternary azeotrope and the water that produces in the water that contains in the raw material and the esterification process is removed by benzene, ethanol, water three, to improve the one-tenth ester rate of lactic acid.After esterification finished, the mixture of recovery part ethanol and benzene carried out the electrically heated atmospheric distillation then in rectifying still (tower), and getting 147～157 ℃ of fractions is the ethyl lactate finished product.Because the physical properties and the chemical property of lactic acid and ethyl lactate and lipid acid and fatty-acid ethyl ester have very big difference: (1) lactic acid is typical alpha hydroxy acid, be decomposed into acetaldehyde and formic acid when altogether hot with dilute sulphuric acid, generate rac-Lactide with dewatering agent when altogether hot, the peculiar side reaction of these alcohol acids will reduce the productive rate of lactic acid greatly; (2) ethyl lactate and water dissolve each other fully, and fatty-acid ethyl ester then is slightly soluble in water or water-soluble hardly; (3) lactic raw material itself just contains the water about 20%, and the raw material of fatty acid water content of generally producing fatty-acid ethyl ester is less than 1%, therefore, the subject matter that above-mentioned traditional technology exists is: lactic acid yield only is 55～65%, the raw material consumption height, production cycle is long, equipment capacity is low, poor product quality, and have the smell of tangible benzene by the ethyl lactate of above-mentioned prepared, not only influenced aroma quality, and do not met food hygienic standard, so strictly speaking, the preparation of flavouring agent level ethyl lactate can not be adopted above-mentioned technology.
The object of the present invention is to provide a kind of productive rate height, good economy performance, equipment capacity big, meet the flavouring agent level and require and the reliable new technology for producing ethyl lactate of stable operation.
The objective of the invention is to realize by following technical proposals: this novel process is a raw material with lactic acid (content 80%) and ethanol (content 92～93%), prepare ethyl lactate through batching, total reflux catalytic esterification, dehydration esterification, the processes such as ethanol, rectification under vacuum that reclaim, it is characterized in that: determined that new proportioning raw materials is a lactic acid: ethanol=1: 0.6～1.6 (weight ratio); Catalyzer is for mixing three kinds of acidic cpds that use; The complex compound and the SODIUM PHOSPHATE, MONOBASIC (or potassium primary phosphate) of hydrogen type strong acid resin, glycerol (or ethylene glycol) and boric acid, its weight ratio is 1: 0.5～1.0: 0.1～0.2, its total consumption is 2～6% of a lactic acid weight; Dewatering agent dehydrated alcohol (content 99.1～99.6%) is after the total reflux esterification process finishes, and adds continuously in the reactor, steams light ethanol simultaneously, and it is in a basic balance that dehydrated alcohol add-on and the light ethanol amount of steaming keep.
Above-mentioned whole process of production is carried out in a block response still (tower).
State-Owned Wujiang Perfumery adopt the present invention produced 400 surplus ton ethyl lactate, production practice prove, the present invention compared with prior art, (1) the productive rate height that has the following advantages (lactic acid yield reaches 97.2%, improves 32～42% than prior art); (2) low (the ethyl lactate raw material consumption standard with national-level enterprise [is selected from " light industry national-level enterprise standard (revised edition) " first volume to raw material consumption, Ministry of Light Industry of the People's Republic of China (PRC), in July, 1988,236 pages] compare, the lactic acid unit consumption standard of class-one national enterprises is 1.450 tons/ton, the lactic acid unit consumption standard of second-class state enterprise is 1.500 tons/ton, and lactic acid unit consumption of the present invention is stabilized in 0.973 ton/ton; (3) production cost reduces by 35～40%; (4) equipment capacity (in the reactor of unit volume) improves about 4 times; (5) facility investment reduces about 30%; (6) improved the security of operating; (7) product fragrance is pure, quality be up to state standards GB8319-87 and U.S. FCCIII standard, and meet food hygienic standard.
Accompanying drawing is the process flow diagram that novel process is produced lactic acid acetate.
The capital equipment that new technology is produced ethyl lactate comprises: reactor [1], esterification tower [2], condenser [3], liquid storage device [4], cooler [5], look letter [6], flowmeter [7], [8], [9] and other auxiliary equipment, such as thermometer [T], Pressure gauge [P] etc. [10] are ethyl lactate finished product discharging opening among the figure, and [11] are light ethanol and ethyl lactate chieftain discharging opening, and [12] are the absolute ethyl alcohol charging aperture, and [13] are material inlet.
The present invention is explained in detail by embodiment below in conjunction with accompanying drawing:
1. batching employing lactic acid (content 80%) and ethanol (content 92～93%) are raw material, and its proportioning is a lactic acid: ethanol=1: 0.6～1.6 (weight ratio); Three kinds of acidic cpds that adopt mixing to use are catalyzer, it consists of the complex compound and the SODIUM PHOSPHATE, MONOBASIC (or potassium primary phosphate) of hydrogen type strong acid resin, glycerol (or ethylene glycol) and boric acid, its weight ratio is 1: 0.5～1.0: 0.1～0.2, and its total consumption is 2～6% of a lactic acid weight.
2. the total reflux esterification drops into the raw material (containing catalyzer) of ammonium said ratio preparation in 1200 liters of reactors [1], feeds steam in the chuck of reactor [1], and the total reflux esterification is about 3 hours.In this process, about vapor pressure 0.04MPa (gauge pressure), the liquid temperature is 88 ± 1 ℃ in the still in the control chuck, 88 ± 0.5 ℃ of top temperature.
3. dehydrated alcohol dehydration esterification, adds reactor [1] bottom with dehydrated alcohol (content 99.1～99.6%), and opens bleeder valve [11] simultaneously after the total reflux esterification process finishes in order to improve the one-tenth ester rate of lactic acid, steams light ethanol, the esterification of dewatering.The dehydrated alcohol add-on keeps light ethanol amount of steaming and dehydrated alcohol add-on in a basic balance by under meter [8] control.In this process, about the interior vapor pressure 0.04MPa (gauge pressure) of control chuck, and the reflux ratio different according to different steps control, keep the top temperature and steam corresponding relation between the alcohol concn, have water as much as possible in the ethanol and have ethyl lactate as few as possible to reach to steam.Through dehydration esterification in 20～22 hours, 94～96 ℃ of liquid temperature, 78.0～78.5 ℃ of top temperature steamed alcohol concn and reach at 98.8～99.0% o'clock in still, and the dehydration esterification finishes.
Annotate: steam ethanol after dehydrated alcohol is made in concentrated, dehydration, reply and use.
4. reclaim resin and normal pressure recovery ethanol and in the chuck of reactor [1], feed water coolant, to isolate the h type resin that is deposited in the still bottom after the thick ester cooling in the still, open jacket steam again, under certain reflux ratio, normal pressure reclaims ethanol to still temperature and reaches end about 110 ℃.
Annotate: the h type resin of recovery with washing with alcohol after, reply and use.
5. decompression recycling ethanol and go out the ethyl lactate chieftain thick ester in the still is cooled to about 50 ℃ is opened vacuum pump, adds last ethyl lactate chieftain, beginning rectification under vacuum operation.Vapor pressure is ascending in the control chuck, reflux ratio is descending, and when cat head not during fluid, decompression recycling ethanol finishes.Then continue to strengthen vapor pressure in the chuck, begin to steam lactic acid acetate chieftain, this moment control tower serious reciprocal of duty cycle-0.092～-0.094MPa (gauge pressure), top temperature 80～83 ℃ and certain reflux ratio, reach a certain amount of and fluid when stablizing when steaming the ethyl lactate chieftain, promptly change out the ethyl lactate finished product over to.
6. go out this process control jacket steam pressure 0.15～0.30MPa (gauge pressure) of ethyl lactate finished product, top vacuum degree-0.093～-0.094MPa (gauge pressure), top temperature 83～84 ℃ and certain reflux ratio.When below the top temperature drop to 75 ℃ and liquid outlet quantity seldom the time, promptly finish finished product.
Annotate: the rectifying residuum answer that contains catalyzer in the still on a small quantity is used in batching esterification next time.
By the ethyl lactate that above-mentioned novel process is produced, through quality of flavoring supervision inspection center of Ministry of Light Industry sampling Detection, detected result is as follows: (table is seen the literary composition back)
Standard GB 8317-87 and U.S.'s FCCIII standard are as follows: look shape≤No. 5 colour code, contain ester amount (%) 〉=98.0, relative density (25/25 ℃) 1.029～1.032, refractive index (20 ℃) 1.410～1.420, (mgkOH/g)≤1.0 are planted in acid, arsenic content (%)≤0.0002, heavy metal (in Pb) (%)≤0.001.
Detected result all meets the regulation of GB8317-87 and U.S. FCCIII standard.
| Test item | Measured result | ||
| Detected (numbering 89-123-1) in 90 years | Detected (numbering 91-124) in 91 years | Detected (numbering 92-13-2) in 92 years | |
| The look shape | ＜No. 5 colour codes | Colourless liquid | Qualified |
| Contain ester amount (%) | ??99.7 | ????98.82 | ???99.6 |
| Relative density (25/25 ℃) | ??1.030 | ????1.0295 | ???1.0295 |
| Refractive index (20 ℃) | ??1.4131 | ????1.4108 | ???1.4130 |
| Acid number (mgKOH/g) | ??0.6 | ????0.18 | ???0.33 |
| Arsenic content (%) | Do not detect | ????＜0.0002 | Qualified |
| Heavy metal (in pb) (%) | ??＜10PPm | ????＜0.001 | Qualified |
Claims (2)
1. novel process of producing ethyl lactate, it comprises that with lactic acid and ethanol be raw material, prepare ethyl lactate through batching, total reflux catalytic esterification, dehydration esterification, the processes such as ethanol, rectification under vacuum that reclaim, it is characterized in that: lactic acid and alcoholic acid weight ratio are 1: 0.6～1.6; Catalyzer is for mixing three kinds of acidic cpds that use: the complex compound of hydrogen type strong acid resin, glycerol or ethylene glycol and boric acid and potassium primary phosphate or SODIUM PHOSPHATE, MONOBASIC, its weight ratio is 1: 0.5～1.0: 0.1～0.2, and its total consumption is 2～6% of a lactic acid weight; Adopting the dehydrated alcohol of content 99.1～99.6% is dewatering agent
2. novel process according to claim 1 is characterized in that dehydrated alcohol is after the total reflux esterification process finishes, and adds continuously in the reactor, steams light ethanol simultaneously, and it is in a basic balance that dehydrated alcohol add-on and the light ethanol amount of steaming keep.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93118797 CN1032855C (en) | 1993-10-28 | 1993-10-28 | new process for producing ethyl lactate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93118797 CN1032855C (en) | 1993-10-28 | 1993-10-28 | new process for producing ethyl lactate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1102180A CN1102180A (en) | 1995-05-03 |
| CN1032855C true CN1032855C (en) | 1996-09-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 93118797 Expired - Lifetime CN1032855C (en) | 1993-10-28 | 1993-10-28 | new process for producing ethyl lactate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1032855C (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2876379B1 (en) * | 2004-10-08 | 2008-09-05 | Isochem Sa | PROCESS FOR POLYMERIZING O-CARBOXY ANHYDRIDES |
| EP2470494B1 (en) * | 2009-09-07 | 2013-12-11 | Council of Scientific & Industrial Research | Process for preparation of pure alkyl esters from alkali metal salt of carboxylic acid |
| 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 |
| PL229904B1 (en) | 2015-01-08 | 2018-09-28 | Wroclawskie Centrum Badan Eit Spolka Z Ograniczona Odpowiedzialnoscia | Method for obtaining lactic acid esters and lactate lactic acid esters in the reaction of aliphatic polyester alcoholysis |
| CN107033000A (en) * | 2016-02-03 | 2017-08-11 | 天津中福工程技术有限公司 | A kind of continuous liquid of fixed bed method that catalysis prepares lactate admittedly |
| CN106220497A (en) * | 2016-07-13 | 2016-12-14 | 盐城华德（郸城）生物工程有限公司 | A kind of ethyl lactate continuous esterification technique |
| CN106220501A (en) * | 2016-08-25 | 2016-12-14 | 江苏九天高科技股份有限公司 | A kind of water vapour penetration dehydration technique is for the method and apparatus of Synthesis of ethyl lactate |
-
1993
- 1993-10-28 CN CN 93118797 patent/CN1032855C/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| CN1102180A (en) | 1995-05-03 |
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