CN106966901A - A kind of preparation method of 6- hydroxyls -8- Lipase Catalyzed Resolution of Racemic Ethyl - Google Patents
A kind of preparation method of 6- hydroxyls -8- Lipase Catalyzed Resolution of Racemic Ethyl Download PDFInfo
- Publication number
- CN106966901A CN106966901A CN201610018183.9A CN201610018183A CN106966901A CN 106966901 A CN106966901 A CN 106966901A CN 201610018183 A CN201610018183 A CN 201610018183A CN 106966901 A CN106966901 A CN 106966901A
- Authority
- CN
- China
- Prior art keywords
- kodalk
- filter
- racemic ethyl
- lipase catalyzed
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F9/00—Multistage treatment of water, waste water or sewage
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/001—Processes for the treatment of water whereby the filtration technique is of importance
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2301/00—General aspects of water treatment
- C02F2301/08—Multistage treatments, e.g. repetition of the same process step under different conditions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a kind of lipoic acid intermediate, i.e. structural formula such as formula(Ⅰ)The preparation method of shown 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl, described 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl is with structure such as formula(Ⅱ)Shown 6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl is initiation material, is made by reduction.The present invention is compared with prior art, it is succinct that its advantage is mainly synthesis step, reduce the use of organic solvent, avoid direct discharging of waste water, so that the kodalk produced is easily isolated, it will not successfully reclaim kodalk solid with other substance reactions, also ammoniacal liquor recycled in addition.Particularly, it is that industrially further recovery prepares sodium borohydride by boron element by reclaiming kodalk, recycles boron element acquisition and create possibility.Whole technique meets green syt and technology requirement, suitable for large-scale industrial production.
Description
Technical field
The invention belongs to organic synthetic route design and industrial waste water treatment, more particularly to a kind of 6- hydroxyls -8
The preparation method and waste water containing boron processing method of Lipase Catalyzed Resolution of Racemic Ethyl.
Background technology
6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl is that one of intermediate of lipoic acid is prepared by initiation material of adipic acid, wherein with 6- oxygen
Generation -8- Lipase Catalyzed Resolution of Racemic Ethyl prepares 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl by reducing.Lipoic acid has powerful oxidation resistance,
The country is mainly used in the treatment of diabete peripheral herve pathology;Abroad in addition to as medicine, dietary supplements and change are also served as
Cosmetic raw material is widely used.
The reduction of 6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl prepares 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl techniques, main using 6- oxos -8-
Lipase Catalyzed Resolution of Racemic Ethyl obtains 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl, instead by selective reducing agent such as sodium borohydride, the carbonyl of reduction the 6th
Answer equation as follows:
US2792406 reports a kind of method for preparing 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl when description prepares lipoic acid route.6-
Oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl is dissolved in tetrachloroethanes, is cooled to less than 10 DEG C, and ethanol solution of sodium borohydride is added dropwise(1:20),
Completion of dropping, is reacted at room temperature 1.5~2 hours, adjusts pH=1~2 with hydrochloric acid, add water layering, organic layer sodium acid carbonate, anhydrous
Magnesium sulfate is dried, and is concentrated in vacuo and is obtained 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl.
In above-mentioned patent description, after the layering that adds water, organic layer obtains product, and water layer processing is not described further.
In actual production, because above-mentioned water layer contains sodium borohydride and ethanol synthesis mixture, it is impossible to separate, recycling difficulty is big,
Waste water can only be worked as and make harmless treatment.
And the method report for handling waste water containing boron has a lot, patent ZL02158593.5 reports a kind of place of waste water containing boron
Reason method, using two sections of addition oxidants (such as hydrogen peroxide) and oxidation/flocculation treatment of flocculant, is greatly reduced Boron contents
Afterwards, then coordinate ion-exchange-resin process or hyperfiltration to remove residual low concentration part, the waste water containing boron of high concentration is for example sent out
Power plant effluent, which can be processed, reaches the target of discharge standard.But it does not regard boron element as resource recycling.
It is well known that accessory substance is kodalk after preparing hydrogen by sodium borohydride hydrolysis.Industrially, kodalk can pass through carbonization
Method prepares borax;By being acidified neutralisation, two-step method is commonly called as, it is to produce boron both at home and abroad at present that boric acid is prepared by raw material of borax
The method that acid is generally used;Boric acid is the industrial raw material for preparing sodium borohydride again;Boron element is followed by above-mentioned steps
Ring is utilized.Easier,《Sodium borohydride synthesizes the current situation with preparation method》(《Power technology》3 phases in 2008)Report
By electrochemical techniques, the method that sodium borohydride is directly prepared with kodalk.It can be seen that, produced as long as sodium borohydride is reacted
Accessory substance kodalk separate, industrially just there is method carry out boron element and recycle.
From green syt and cleanly production angle, it is necessary to seek a kind of new 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl
Preparation method so that after the completion of reaction, sodium borohydride participates in obtaining kodalk after reduction reaction and is dissolved in the material of water layer
Separation is readily able to, reduction environmental pollution is reached, the purpose of production cost is reduced, for promoting 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl
Economic technology development have important realistic meaning.
The content of the invention
It is new there is provided one kind according to the synthesis theory of Green Chemistry it is an object of the invention to overcome the defect of prior art
6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl preparation methods, and handle reaction produced by waste water containing boron.This method economy, environmental protection, have
Beneficial to the industrialized production of the product, and the economic technology of 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl can be promoted to develop.
For achieving the above object, the present invention is adopted the following technical scheme that:
6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl is dissolved in dichloroethanes, and temperature is maintained at 10~30 DEG C, adds phase transfer catalyst, drop
Plus sodium borohydride ammonia spirit, react 2~4 hours, filtering layering, organic layer salt acid for adjusting pH=5~6 are concentrated in vacuo to obtain 6-
Hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl.Water layer obtains the kodalk separated out by filter, filtrate concentration and recovery ammoniacal liquor, crystallisation by cooling,
Filtering obtains kodalk again.
The phase transfer catalyst, is the quaternary ammonium salt phase such as TBAB, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate
Transfer catalyst, preferably TBAB.
6- oxos -8- the Lipase Catalyzed Resolution of Racemic Ethyl:TBAB:Sodium borohydride mass ratio is:1:0.01~0.05:
0.05~0.08
The ammonia concn is:5%~17%
Water layer processing method is after the reduction reaction:
1. water layer obtains the kodalk solid separated out by filter after reacting;
2. filtrate is put into the concentration tank equipped with retracting device, 100 DEG C of recovery ammoniacal liquor;
3. water temperature is down to less than 30 DEG C and separates out kodalk solid again;
4. the kodalk that mother liquor is separated out is removed, is merged with the kodalk of 1. middle acquisition and is dried and reclaim;
5. in 2. the filtrated stock for having separated out kodalk being added into next group waste water containing boron process step.
Water layer processing method after the reduction reaction that the present invention is provided, the step boils off water when 1. reclaiming ammoniacal liquor be about every
Criticize the 50%-75% of reduction gained water layer weight.
Present invention also offers the equipment that water layer after a kind of reduction reaction is recycled, the equipment includes:
Filter 1, removes the kodalk solid that water layer has been separated out;
Water layer after concentration and recovery tank, input reduction reaction, reclaims ammoniacal liquor;
Cold analysis tank, is directly connected to filter, will reclaim the concentrate after ammoniacal liquor and has been cooled down;
Filter 2, removes the kodalk solid that mother liquor is separated out;
Circulating line, mother liquor is applied mechanically, and is reclaimed ammoniacal liquor and then returned in reactions steps and use.
Present invention also offers the equipment that water layer after a kind of reduction reaction is recycled, its feature also includes pipeline and connects suitable
Sequence is:Filter 1, concentration and recovery tank(Connect condenser, receiving tank, spray absorption tower), cold analysis tank, filter 2;Filter is used
Pipeline is connected with concentration and recovery tank, for Recycling Mother Solution.
The present invention is due to using above technical scheme, compared to prior art, and its advantage is mainly synthesis step succinctly, subtracts
The use of organic solvent is lacked, it is to avoid direct discharging of waste water so that the kodalk of generation is easily isolated, will not be with other things
Qualitative response, has successfully reclaimed kodalk solid, also ammoniacal liquor has been recycled in addition.Particularly, it is inclined by reclaiming
Boratex, is that industrially by boron element, further recovery prepares sodium borohydride, obtains boron element and recycles that create can
Energy.Whole technique meets green syt and technology requirement, suitable for large-scale industrial production.
Brief description of the drawings
For the above objects, features and advantages of the present invention can be become apparent, below in conjunction with tool of the accompanying drawing to the present invention
Body embodiment elaborates, wherein:
Fig. 1 is present invention process flow chart;
Fig. 2 is reduction reaction water layer processing equipment figure of the present invention;
The mark inventory of accompanying drawing 2 is as follows:
1st, filter 1,2, concentration and recovery tank, 3, cold analysis tank, 4, filter 2,5, drier, 6, condenser, 7, receiving tank, 8, spray
Pouring formula absorption tower.
Embodiment
Embodiment 1:
100Kg 6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl is dissolved in 500Kg dichloroethanes, temperature is maintained at 10~30 DEG C, adds 1Kg
TBAB, is added dropwise 17% ammonia spirit 100Kg of the sodium borohydride containing 5Kg, reacts 4 hours, filtering layering, organic layer
Concentrated with hydrochloric acid regulation pH=5~6,0.1MPa heating under reduced pressure, to 110 DEG C of end of temperature, obtain the 6- hydroxyl -8- chlorine of purity 92%
Ethyl caprilate concentrate 98Kg.Water layer obtains the kodalk separated out by filter, and the ammoniacal liquor 75Kg of filtrate concentration and recovery 10% is returned
With crystallisation by cooling, filtering obtains kodalk again, and mother liquor returns set, merges gained kodalk 13.8Kg, 100 DEG C dry
7.6Kg, purity 95%.
Embodiment 2:
100Kg 6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl is dissolved in 500Kg dichloroethanes, temperature is maintained at 10~30 DEG C, adds 1Kg
TBAB, is added dropwise 10% ammonia spirit 100Kg of the sodium borohydride containing 8Kg, wherein 75Kg ammoniacal liquor is that embodiment 1 is reclaimed
Gained, reacts 2 hours, and filtering layering, organic layer adjusts pH=5~6,0.1MPa heating under reduced pressure with hydrochloric acid and concentrated, to temperature 110
DEG C terminate, obtain the 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl concentrates 99Kg of purity 90%.Water layer obtains the inclined boron separated out by filter
Sour sodium, filtrate merges with the mother liquor of embodiment 1, the ammoniacal liquor 60Kg of concentration and recovery 7%, crystallisation by cooling, and filtering obtains kodalk again, merges
Gained kodalk 21.5Kg, 100 DEG C dry to obtain 11Kg, purity 98%.
Embodiment 3:
100Kg 6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl is dissolved in 500Kg dichloroethanes, temperature is maintained at 10~30 DEG C, adds 5Kg
TBAB, is added dropwise 5% ammonia spirit 100Kg of the sodium borohydride containing 8Kg, reacts 4 hours, and filtering layering, organic layer is used
Hydrochloric acid regulation pH=5~6,0.1MPa heating under reduced pressure concentrations, to 110 DEG C of end of temperature, the 6- hydroxyl -8- chlorine for obtaining purity 94% is pungent
Acetoacetic ester concentrate 95Kg.Water layer obtains the kodalk separated out by filter, and filtrate reclaims 4% ammoniacal liquor 50Kg, while mother liquor
Concentration, crystallisation by cooling, filtering obtains kodalk again, merges gained kodalk 20.7Kg, 100 DEG C dry to obtain 11.1Kg, purity
94%。
It is pointed out that the technical concepts and features of above-mentioned preferred embodiment only to illustrate the invention, its object is to
Person skilled in the art can understand present disclosure and implement according to this, the protection of the present invention can not be limited with this
Scope.Any equivalent change or modification in accordance with the spirit of the invention, should all be included within the scope of the present invention.
Claims (7)
1. a kind of lipoic acid intermediate 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl(Ⅰ)Preparation method:
,
It is characterized in that the preparation method following steps:By 6- oxo -8- Lipase Catalyzed Resolution of Racemic Ethyl(Ⅱ)It is dissolved in dichloroethanes, temperature
Degree is maintained at 10~30 DEG C, adds phase transfer catalyst, and sodium borohydride ammonia spirit is added dropwise, and reacts 2~4 hours, filtering layering,
Organic layer salt acid for adjusting pH=5~6, are concentrated in vacuo to obtain 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl(Ⅰ);Water layer is obtained by filter and analysed
The kodalk gone out, filtrate concentration and recovery ammoniacal liquor, crystallisation by cooling, filtering obtains kodalk again,
。
2. the preparation method of lipoic acid intermediate according to claim 1, it is characterised in that:The phase used in reduction reaction turns
Shifting catalyst is the quaternary ammonium salts, preferably TBAB such as TBAB, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate.
3. the preparation method of lipoic acid intermediate according to claim 1, it is characterised in that:Material 6- oxygen in reduction reaction
Generation -8- Lipase Catalyzed Resolution of Racemic Ethyl:TBAB:Sodium borohydride mass ratio is 1:0.01~0.05:0.05~0.08.
4. the preparation method of lipoic acid intermediate according to claim 1, it is characterised in that:Configure sodium borohydride ammonia spirit
The ammonia concn used is 5%~17%.
5. the preparation method of lipoic acid intermediate according to claim 1, it is characterised in that:There is provided a kind of reduction reaction
Post-processing approach, including:
1. water layer obtains the kodalk solid separated out by filter after reacting;
2. filtrate is put into the concentration tank equipped with retracting device, 100 DEG C of recovery ammoniacal liquor;
3. water temperature is down to less than 30 DEG C and separates out kodalk solid again;
4. the kodalk that mother liquor is separated out is removed, is merged with the kodalk of 1. middle acquisition and is dried and reclaim;
5. in 2. the filtrated stock for having separated out kodalk being added into next group waste water containing boron process step;
Above-mentioned steps boil off the 50%-75% that water is about every batch of reduction gained water layer weight when 1. reclaiming ammoniacal liquor.
6. the post-processing approach of reduction reaction according to claim 5, it is characterised in that:Use after a set of reduction reaction
The equipment that water layer is recycled, equipment includes:
1. filter 1, removes the kodalk solid that water layer has been separated out;
2. concentration and recovery tank, inputs water layer after reduction reaction, reclaims ammoniacal liquor;
3. cold analysis tank, is directly connected to filter, will reclaim the concentrate after ammoniacal liquor and has been cooled down;
4. filter 2, remove the kodalk solid that mother liquor is separated out;
5. circulating line, mother liquor is applied mechanically, and is reclaimed ammoniacal liquor and then returned in reactions steps and use.
7. the equipment that water layer is recycled after reduction reaction according to claim 6, it is characterised in that:The pipeline order of connection
For:Filter 1, concentration and recovery tank(Connect condenser, receiving tank, spray absorption tower), cold analysis tank, filter 2;Filter is managed
Road is connected with concentration and recovery tank, for Recycling Mother Solution.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610018183.9A CN106966901B (en) | 2016-01-13 | 2016-01-13 | A kind of preparation method of 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610018183.9A CN106966901B (en) | 2016-01-13 | 2016-01-13 | A kind of preparation method of 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106966901A true CN106966901A (en) | 2017-07-21 |
CN106966901B CN106966901B (en) | 2019-11-26 |
Family
ID=59334205
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610018183.9A Active CN106966901B (en) | 2016-01-13 | 2016-01-13 | A kind of preparation method of 6- hydroxyl -8- Lipase Catalyzed Resolution of Racemic Ethyl |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106966901B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108373411A (en) * | 2017-12-16 | 2018-08-07 | 山东新华制药股份有限公司 | The preparation method of high-purity 4- chloro-3-hydroxyl ethyl butyrates |
CN114149324A (en) * | 2021-12-07 | 2022-03-08 | 厦门金达威维生素有限公司 | Synthesis method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2877235A (en) * | 1954-05-28 | 1959-03-10 | Du Pont | Alpha-lipoic acid process |
US2975198A (en) * | 1954-07-08 | 1961-03-14 | Research Corp | Lipoic acid intermediates |
CN101157614A (en) * | 2007-09-30 | 2008-04-09 | 浙江工业大学 | Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate |
CN102531299A (en) * | 2012-03-06 | 2012-07-04 | 江苏同禾药业有限公司 | Method for treating addition wastewater in production process of lipoic acid |
CN102731307A (en) * | 2012-07-17 | 2012-10-17 | 江苏同禾药业有限公司 | Preparation method of ethyl 6-oxo-8-chloro-caprylate |
CN104261629A (en) * | 2014-10-11 | 2015-01-07 | 江苏同禾药业有限公司 | Combined treatment method for addition waste water and cyclization waste water in production process of lipoic acid |
CN104671570A (en) * | 2014-12-24 | 2015-06-03 | 江苏同禾药业有限公司 | Method for treating aluminum-containing wastewater in preparation process of 6-oxo-8-chloro ethyl caprylate |
CN105087681A (en) * | 2015-08-18 | 2015-11-25 | 苏州富士莱医药股份有限公司 | Preparation method and application of ethyl (S)-6-hydroxy-8-chlorocaprylate |
-
2016
- 2016-01-13 CN CN201610018183.9A patent/CN106966901B/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2877235A (en) * | 1954-05-28 | 1959-03-10 | Du Pont | Alpha-lipoic acid process |
US2975198A (en) * | 1954-07-08 | 1961-03-14 | Research Corp | Lipoic acid intermediates |
CN101157614A (en) * | 2007-09-30 | 2008-04-09 | 浙江工业大学 | Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate |
CN102531299A (en) * | 2012-03-06 | 2012-07-04 | 江苏同禾药业有限公司 | Method for treating addition wastewater in production process of lipoic acid |
CN102731307A (en) * | 2012-07-17 | 2012-10-17 | 江苏同禾药业有限公司 | Preparation method of ethyl 6-oxo-8-chloro-caprylate |
CN104261629A (en) * | 2014-10-11 | 2015-01-07 | 江苏同禾药业有限公司 | Combined treatment method for addition waste water and cyclization waste water in production process of lipoic acid |
CN104671570A (en) * | 2014-12-24 | 2015-06-03 | 江苏同禾药业有限公司 | Method for treating aluminum-containing wastewater in preparation process of 6-oxo-8-chloro ethyl caprylate |
CN105087681A (en) * | 2015-08-18 | 2015-11-25 | 苏州富士莱医药股份有限公司 | Preparation method and application of ethyl (S)-6-hydroxy-8-chlorocaprylate |
Non-Patent Citations (1)
Title |
---|
REED, LESTER J.;等,: "Syntheses of DL-α-lipoic acid", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108373411A (en) * | 2017-12-16 | 2018-08-07 | 山东新华制药股份有限公司 | The preparation method of high-purity 4- chloro-3-hydroxyl ethyl butyrates |
CN114149324A (en) * | 2021-12-07 | 2022-03-08 | 厦门金达威维生素有限公司 | Synthesis method of 6-hydroxy-8-chloro ethyl caprylate, 6, 8-dichloro ethyl caprylate and lipoic acid |
CN114149324B (en) * | 2021-12-07 | 2023-08-22 | 厦门金达威维生素有限公司 | Synthesis method of 6-hydroxy-8-chlorooctanoic acid ethyl ester, 6, 8-dichloro octanoic acid ethyl ester and lipoic acid |
Also Published As
Publication number | Publication date |
---|---|
CN106966901B (en) | 2019-11-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101058853A (en) | Method of reclaiming chemical industry products by using industrial slag containing vanadium, chromium, iron and phosphorous | |
CN111018221B (en) | Method for recycling smelting waste acid wastewater | |
CN108439438A (en) | The method that nickel cobalt mn sulphate and lithium carbonate are prepared by waste and old ternary battery material | |
CN105293454B (en) | A kind of method that spent solder stripper prepares dust technology, spongy tin and aluminium polychlorid | |
CN106185852A (en) | A kind of method utilizing phosphorus ore to prepare purifying phosphoric acid | |
CN102557085A (en) | Method for producing cesium salt and rubidium salt based on zero discharge and continuous extraction | |
CN103663505B (en) | Method for treating potassium feldspar according to sub-molten salt method to prepare potassium carbonate | |
CN111086977B (en) | Method for preparing MCP and MDCP (Madin-Darby Canine phosphate) by using raffinate acid | |
CN104773748B (en) | A kind of method for preparing low iron polyaluminium sulfate using the acid mother liquor of sulfur waste containing aluminium | |
CN110790235B (en) | Comprehensive utilization method of fluorine-containing potassium chloride as organic synthesis byproduct | |
CN104003428A (en) | Method for producing lithium hydroxide by dissolving spodumene out of pipeline reactor | |
CN102731357B (en) | Preparation method of high purity N,N'-dicyclohexylthiourea | |
CN104340967A (en) | High stability graphite purification method | |
CN106966901A (en) | A kind of preparation method of 6- hydroxyls -8- Lipase Catalyzed Resolution of Racemic Ethyl | |
CN104909489B (en) | A kind of process for producing of trichloro-isocyanuric acid sewage water treatment method | |
CN104086439A (en) | Method for recovering pregabalin intermediate resolving agent (R)-(+)-alpha-phenylethylamine | |
CN113955753A (en) | Method for recovering waste lithium iron phosphate battery powder | |
CN103241720B (en) | Method for preparing amorphous iron phosphate by using phosphate sludge | |
CN103193253B (en) | Pressurized acid-leaching potassium extracting technology for potassium feldspar | |
CN109627183B (en) | Preparation method of chloroacetaldehyde oxime | |
CN102992288B (en) | Method for preparing high pure phosphoric acid from calcium hydrogen phosphate | |
CN103073458A (en) | Method for recovering trifluoromethanesulfonic acid in wastewater | |
CN106316956A (en) | Industrial production method for pyrazole | |
CN103664527A (en) | Clean preparation method for 2,4-dichloro-alpha-chloromethyl benzyl alcohol | |
CN106316755A (en) | Method for treating waste sulfuric acid through extraction separation coupled ammonium chloride reaction |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |