CN106008244B - A kind of synthetic method of 4 dimethylamino valeric acid - Google Patents
A kind of synthetic method of 4 dimethylamino valeric acid Download PDFInfo
- Publication number
- CN106008244B CN106008244B CN201610339014.5A CN201610339014A CN106008244B CN 106008244 B CN106008244 B CN 106008244B CN 201610339014 A CN201610339014 A CN 201610339014A CN 106008244 B CN106008244 B CN 106008244B
- Authority
- CN
- China
- Prior art keywords
- acid
- solution
- reaction
- valeric acid
- dimethylaminos
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/10—Formation of amino groups in compounds containing carboxyl groups with simultaneously increasing the number of carbon atoms in the carbon skeleton
Abstract
A kind of synthetic method of 4 dimethylamino valeric acid, is related to 4 dimethylamino valeric acids.Comprise the following steps：1) reactant levulic acid is mixed in proportion with reaction solution, after heating response, obtains solution A；The reaction solution is N, N dimethylformamides, formic acid and water；2) by solution A vacuum distillation recovered solvent, and residue is diluted with acetone, obtains solution B；3) solution B is separated by column chromatography, obtains the 4 dimethylamino valeric acid.Using levulic acid as reactant, with N, the mixed liquor of N dimethylformamides and formic acid or water is reaction solution, heating response after mixing, 180~285 DEG C of reaction temperature, heat time is 1~20h, the dimethylamino valeric acid of product 4 can be obtained, one kettle way production simple efficient with reaction, it is easy to purification, develops a kind of effective way for preparing 4 dimethylamino valeric acid products.
Description
Technical field
The present invention relates to 4- dimethylamino valeric acids, more particularly to a kind of synthetic method of 4- dimethylaminos valeric acid.
Background technology
In recent years, with the increase of energy field risk, efficiently prepared through chemical conversion by reproducible biomass high attached
Value added compound turns into the study hotspot that biomass converts field.Biomass mainly includes cellulose, hemicellulose and wood
The big component of quality three.The biomass-based raw material such as hexose such as glucose, fructose and downstream intermediate 5 hydroxymethyl furfural pass through also
Former amination can obtain 5- [(dimethylamino) methyl] -2- furancarbinols, be that synthesis common drug H2- receptor antagonist thunder Buddhist nuns replace
The important intermediate of fourth.Patent CN104059036A discloses a kind of synthesis of 5- [(dimethylamino) methyl] -2- furancarbinols
Method, it is raw material using monose, disaccharides and hydroxymethylfurfural, and purpose product is generated in a mild condition.Patent US8669383
Disclose a kind of method that furan derivative is prepared by carbohydrate, it is characterised in that solid acid is with hydrogenation catalyst in hydrogen
Concerted catalysis carbohydrate prepares furan derivative under the conditions of gas.Patent US6743819B1, US6900337B2,
US20040192933A1 is disclosed by the distinct methods of bio-based levulic acid reduction amination synthesis of pyrrolidine ketone compounds,
It synthesizes the five-membered ring pyrrolidones of different nitrogen substituents using noble metal catalyst under an atmosphere of hydrogen.
By cellulose platform chemicals levulic acid can be relatively easily obtained by sour water solution.Utilize levulic acid intramolecular
Active carbonyl and carboxyl can further obtain the fuel and fine chemicals of high added value.Because biomass-based material has well
Biological degradability and bio-compatibility make it have very significant environmental benefit and economic benefit.
The reduction amination of levulic acid has been subjected to the extensive concern of scientific research circle, and its current research direction is concentrated mainly on system
The pyrrolidones that standby nitrogenous five member ring heterocyclic compound-N bases replace.Prepared by occurring reductive amination process with primary amine
Pyrrolidinone compounds product is considered as that can substitute the effective way of petroleum base pyrrolidinone compounds product.The pyrrolidines of N bases substitution
Ketone compounds can be widely applied in industry, can be as industrial solvent, cleaning agent, eluant, eluent etc., and application field is quite varied.
4- dimethylaminos butyric acid, 5- dimethylamino valeric acids are widely used in synthesis fine chemicals, can also be used as biological doctor
Medicine and material intermediate.Intramolecular is containing activity high basic group dimethylamino and acidic-group carboxyl so that such compound
It can be applied to the research of the characteristics such as biologic antibiosis and the synthesis of medicine.γ-aminobutyric acid is even more a kind of conventional nerve suppression
Medicine.(the Chinese feeds of study on the synthesis [J] of the red γ-aminobutyric acids of Yang Dongyuan, Chen Kaixun, Wang Ya, 2010 such as Yang Dongyuan
(1):27-28,41.) a kind of method for preparing γ-aminobutyric acid is reported, this method is needed by open loop chloro, esterification, amine
Change the steps such as hydrolysis, process is complex, process is difficult to control.(Wang Jinling, Yuan Jun, Liu step on ability gamma-amino fourths to Wang Jinling etc.
Synthesis [J] chemistry and bioengineering of acid, 2010 (3):40-42.) using 2-Pyrrolidone as raw material, through calcium hydroxide and carbon
Sour hydrogen ammonium hydrolyzes to obtain γ-aminobutyric acid, adds the difficulty of later stage salt and target product separation.4- dimethylamino valeric acids also belong to
In one kind of amino acid, its purposes awaits further excavation, and the synthetic method of 4- dimethylamino valeric acids has turned into important
Research and develop problem.But at present it is not yet found that synthetic method with identical 4- dimethylamino valeric acids of the present invention.
The synthetic method of report 4- dimethylamino valeric acids is had no at present.
The content of the invention
It is an object of the invention to provide a kind of side of synthesis that 4- dimethylamino valeric acids are prepared by biomass-based levulic acid
Method.The synthetic method has reaction simple efficient, one kettle way production, it is easy to the technique effect such as purification.
The present invention comprises the following steps：
1) reactant levulic acid is mixed in proportion with reaction solution, after heating response, obtains solution A；The reaction
Solution is N,N-dimethylformamide (DMF), formic acid (FA) and water；
2) by solution A vacuum distillation recovered solvent, and residue is diluted with acetone, obtains solution B；
3) solution B is separated by column chromatography, obtains the 4- dimethylaminos valeric acid.
In step 1) in, in the solution A, the mass concentration fraction of reactant levulic acid is 1%~57.5%, N,
The mass concentration fraction of dinethylformamide (DMF) is 3.15%~97.02%, and the mass concentration fraction of formic acid (FA) is 0
~49.5%, the mass concentration fraction of water is 0~91.85%；The temperature of the heating response can be 180~285 DEG C, and heating is anti-
The time answered can be 1~20h.
In step 3) in, the column chromatography can use methanol and ethyl acetate volume ratio for 1: 5 mixed liquor as washing
De- agent, 200 mesh silica gel are stationary phase.
Compared with the prior art, beneficial effects of the present invention are as follows：
The present invention is using levulic acid as reactant, and the mixed liquor using DMF and formic acid or water is molten as reaction
Heating response after liquid, mixing, 180~285 DEG C of reaction temperature, the heat time is 1~20h, you can obtain product 4- dimethylaminos
Valeric acid, one kettle way production, it is easy to purify simple efficient with reaction develops a kind of 4- dimethylamino valeric acid products that prepare
Effective way.
Embodiment
The present invention is further illustrated for following examples.
Embodiment 1
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
Agitating and heating is reacted, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, in 140 DEG C, 2000Pa pressure
Lower vacuum distillation recovered solvent, after being diluted with 2ml acetone, mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 is as washing
De- agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 48.7%.
Embodiment 2
0.2g levulic acids (1wt%), 0.396g formic acid, 19.404gN, N- dimethyl methyls are added in 100ml reactors
Acid amides (DMF) (97.02wt%), agitating and heating reaction, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction,
The vacuum distillation recovered solvent under 140 DEG C, 2000Pa pressure, after being diluted with 2ml acetone, with methanol and ethyl acetate volume ratio
For 1: 5 mixed liquor as eluant, eluent, 200 mesh silica gel are stationary phase, by the isolated 4- dimethylaminos valeric acid of column chromatography,
Product yield is 39.2%.
Embodiment 3
The addition 9.21g levulic acids (57.5wt%) in 100ml reactors, 5.8gN, dinethylformamide (DMF),
1g water, agitating and heating reaction, 200 DEG C of temperature, reaction time 6h.Reaction solution is taken out after completion of the reaction, at 140 DEG C, 2000Pa's
Vacuum distillation recovered solvent under pressure, after being diluted with 2ml acetone, is made using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
For eluant, eluent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is
18.8%.
Embodiment 4
5g levulic acids, 9.9g formic acid (49.5wt%), 5.1gN, dinethylformamide are added in 100ml reactors
(DMF), agitating and heating is reacted, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, in 140 DEG C, 2000Pa
Pressure under vacuum distillation recovered solvent, after being diluted with 2ml acetone, the mixed liquor using methanol and ethyl acetate volume ratio as 1: 5
As eluant, eluent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is
15.5%.
Embodiment 5
The addition 1g levulic acids in 100ml reactors, 0.63gN, dinethylformamide (DMF) (3.15wt%),
18.37g water (91.85wt%), agitating and heating reaction, 240 DEG C of temperature, reaction time 2h.Reaction solution is taken out after completion of the reaction,
140 DEG C, vacuum distillation recovered solvent under 2000Pa pressure, after being diluted with 2ml acetone, using methanol and ethyl acetate volume ratio as
1: 5 mixed liquor is as eluant, eluent, and 200 mesh silica gel are stationary phase, passes through the isolated 4- dimethylaminos valeric acid of column chromatography, production
Product yield is 7.4%.
Embodiment 6
1g levulic acids are added in 100ml reactors, 0.4g formic acid, 18.6gN, dinethylformamide (DMF) is stirred
Mix heating response, 180 DEG C of temperature, reaction time 1h.Reaction solution is taken out after completion of the reaction, is subtracted under 140 DEG C, 2000Pa pressure
Pressure is distilled to recover solvent, after being diluted with 2ml acetone, the mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 as eluant, eluent,
200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 8.6%.
Embodiment 7
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
Agitating and heating is reacted, 180 DEG C of temperature, reaction time 20h.Reaction solution is taken out after completion of the reaction, in 140 DEG C, 2000Pa pressure
Lower vacuum distillation recovered solvent, after being diluted with 2ml acetone, mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 is as washing
De- agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 53.9%.
Embodiment 8
1g levulic acids are added in 100ml reactors, 0.4g formic acid, 18.6gN, dinethylformamide (DMF) is stirred
Mix heating response, 285 DEG C of temperature, reaction time 1h.Reaction solution is taken out after completion of the reaction, is subtracted under 140 DEG C, 2000Pa pressure
Pressure is distilled to recover solvent, after being diluted with 2ml acetone, the mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 as eluant, eluent,
200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 4.4%.
Embodiment 9
1g levulic acids are added in 100ml reactors, 0.4g formic acid, 18.6gN, dinethylformamide (DMF) is stirred
Mix heating response, 200 DEG C of temperature, reaction time 1h.Reaction solution is taken out after completion of the reaction, is subtracted under 140 DEG C, 2000Pa pressure
Pressure is distilled to recover solvent, after being diluted with 2ml acetone, the mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 as eluant, eluent,
200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 19%.
Embodiment 10
1g levulic acids are added in 100ml reactors, 0.4g formic acid, 18.6gN, dinethylformamide (DMF) is stirred
Mix heating response, 230 DEG C of temperature, reaction time 1h.Reaction solution is taken out after completion of the reaction, is subtracted under 140 DEG C, 2000Pa pressure
Pressure is distilled to recover solvent, after being diluted with 2ml acetone, the mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 as eluant, eluent,
200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 37.7%.
Embodiment 11
The addition 2g levulic acids in 100ml reactors, 3.96g formic acid, 14.04gN, dinethylformamide (DMF),
Agitating and heating is reacted, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, in 140 DEG C, 2000Pa pressure
Lower vacuum distillation recovered solvent, after being diluted with 2ml acetone, mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 is as washing
De- agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 52.7%.
Embodiment 12
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
Agitating and heating is reacted, 180 DEG C of temperature, reaction time 4h.Reaction solution is taken out after completion of the reaction, under 140 DEG C, 2000Pa pressure
Vacuum distillation recovered solvent, after being diluted with 2ml acetone, elution is used as using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
Agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 35.8%.
Embodiment 13
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
Agitating and heating is reacted, 200 DEG C of temperature, reaction time 4h.Reaction solution is taken out after completion of the reaction, under 140 DEG C, 2000Pa pressure
Vacuum distillation recovered solvent, after being diluted with 2ml acetone, elution is used as using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
Agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 55.3%.
Embodiment 14
The addition 1g levulic acids in 100ml reactors, 3.96g formic acid, 15.04gN, dinethylformamide (DMF),
Agitating and heating is reacted, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, in 140 DEG C, 2000Pa pressure
Lower vacuum distillation recovered solvent, after being diluted with 2ml acetone, mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 is as washing
De- agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 51.4%.
Embodiment 15
The addition 1g levulic acids in 100ml reactors, 5.94g formic acid, 17.02gN, dinethylformamide (DMF),
Agitating and heating is reacted, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, in 140 DEG C, 2000Pa pressure
Lower vacuum distillation recovered solvent, after being diluted with 2ml acetone, mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 is as washing
De- agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 54.5%.
Embodiment 16
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
1g water, agitating and heating reaction, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, at 140 DEG C, 2000Pa's
Vacuum distillation recovered solvent under pressure, after being diluted with 2ml acetone, is made using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
For eluant, eluent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is
48.4%.
Embodiment 17
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
5g water, agitating and heating reaction, 180 DEG C of temperature, reaction time 12h.Reaction solution is taken out after completion of the reaction, at 140 DEG C, 2000Pa's
Vacuum distillation recovered solvent under pressure, after being diluted with 2ml acetone, is made using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
For eluant, eluent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is
35.2%.
Embodiment 18
The addition 1g levulic acids in 100ml reactors, 1.98g formic acid, 17.02gN, dinethylformamide (DMF),
Agitating and heating is reacted, 240 DEG C of temperature, reaction time 1h.Reaction solution is taken out after completion of the reaction, under 140 DEG C, 2000Pa pressure
Vacuum distillation recovered solvent, after being diluted with 2ml acetone, elution is used as using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
Agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 43%.
Embodiment 19
The addition 1g levulic acids in 100ml reactors, 7.92g formic acid, 11.08gN, dinethylformamide (DMF),
Agitating and heating is reacted, 200 DEG C of temperature, reaction time 4h.Reaction solution is taken out after completion of the reaction, under 140 DEG C, 2000Pa pressure
Vacuum distillation recovered solvent, after being diluted with 2ml acetone, elution is used as using methanol and ethyl acetate volume ratio as 1: 5 mixed liquor
Agent, 200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 51.5%.
Embodiment 20
1g levulic acids, 6.3gN, dinethylformamide (DMF), 18.37g water, stirring are added in 100ml reactors
Heating response, 240 DEG C of temperature, reaction time 2h.Reaction solution is taken out after completion of the reaction, is depressurized under 140 DEG C, 2000Pa pressure
Be distilled to recover solvent, after being diluted with 2ml acetone, the mixed liquor using methanol and ethyl acetate volume ratio as 1: 5 as eluant, eluent,
200 mesh silica gel are stationary phase, and by the isolated 4- dimethylaminos valeric acid of column chromatography, product yield is 33.3%.
Claims (2)
1. a kind of synthetic method of 4- dimethylaminos valeric acid, it is characterised in that comprise the following steps：
1) reactant levulic acid is mixed in proportion with reaction solution, after heating response, obtains solution A；The reaction solution
For N,N-dimethylformamide, formic acid and water；
In the solution A, the mass concentration fraction of reactant levulic acid is 1%~57.5%, DMF
Mass concentration fraction be 3.15%~97.02%, the mass concentration fraction of formic acid is 0~49.5%, the mass concentration point of water
Number is 0~91.85%；
The temperature of the heating response is 180~285 DEG C, and the time of heating response is 1~20h；
2) by solution A vacuum distillation recovered solvent, and residue is diluted with acetone, obtains solution B；
3) solution B is separated by column chromatography, obtains the 4- dimethylaminos valeric acid.
2. a kind of synthetic method of 4- dimethylaminos valeric acid as claimed in claim 1, it is characterised in that in step 3) in, it is described
Column chromatography use methanol and ethyl acetate volume ratio for 1: 5 mixed liquor as eluant, eluent, 200 mesh silica gel are stationary phase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610339014.5A CN106008244B (en) | 2016-05-20 | 2016-05-20 | A kind of synthetic method of 4 dimethylamino valeric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610339014.5A CN106008244B (en) | 2016-05-20 | 2016-05-20 | A kind of synthetic method of 4 dimethylamino valeric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106008244A CN106008244A (en) | 2016-10-12 |
| CN106008244B true CN106008244B (en) | 2017-10-03 |
Family
ID=57095327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610339014.5A Active CN106008244B (en) | 2016-05-20 | 2016-05-20 | A kind of synthetic method of 4 dimethylamino valeric acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106008244B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681913A (en) * | 1951-11-24 | 1954-06-22 | Searle & Co | Esters of nu, nu-disubstituted amino acids and hydrogenated 4, 7-methanoinden-6-ols and their salts |
| CN1753888A (en) * | 2003-03-01 | 2006-03-29 | 阿斯利康(瑞典)有限公司 | Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents |
| CN101798274A (en) * | 2010-01-06 | 2010-08-11 | 中国石油化工股份有限公司胜利油田分公司地质科学研究院 | Application of amphoteric surfactant in tertiary oil recovery, preparation method and application method of surfactant |
| CN102086158A (en) * | 2009-12-31 | 2011-06-08 | 杭州广林生物医药有限公司 | Method for synthesizing 3-(N,N-2-substituted amino)-2-substituted acrylic esters |
-
2016
- 2016-05-20 CN CN201610339014.5A patent/CN106008244B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681913A (en) * | 1951-11-24 | 1954-06-22 | Searle & Co | Esters of nu, nu-disubstituted amino acids and hydrogenated 4, 7-methanoinden-6-ols and their salts |
| CN1753888A (en) * | 2003-03-01 | 2006-03-29 | 阿斯利康(瑞典)有限公司 | Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents |
| CN102086158A (en) * | 2009-12-31 | 2011-06-08 | 杭州广林生物医药有限公司 | Method for synthesizing 3-(N,N-2-substituted amino)-2-substituted acrylic esters |
| CN101798274A (en) * | 2010-01-06 | 2010-08-11 | 中国石油化工股份有限公司胜利油田分公司地质科学研究院 | Application of amphoteric surfactant in tertiary oil recovery, preparation method and application method of surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106008244A (en) | 2016-10-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2014150387A1 (en) | Method of manufacturing dicarboxylic acids and derivatives from compositions comprising ketocarboxylic acids | |
| CN105111170B (en) | A kind of preparation method of furfuran compound | |
| CN106008244B (en) | A kind of synthetic method of 4 dimethylamino valeric acid | |
| CN107417648B (en) | Synthetic method of 3-aminomethyl tetrahydrofuran | |
| CN107935970A (en) | A kind of preparation method of 3 methylamine tetrahydrofuran of high-purity low water content | |
| CN102827015B (en) | Preparation method of 5-aminolevulinic acid (ALA) hydrochloride | |
| CN105523783A (en) | Method for producing high-additional value chemical co-production slow release fertilizer by straws | |
| CN104293860A (en) | Comprehensive utilization method of furfural slag | |
| CN105801474B (en) | A kind of method of refined 3,6 lontrel | |
| CN108084121A (en) | It is a kind of by the carbohydrate-modifying method for furfural of cellulose family | |
| CN104513170B (en) | A kind of trans production technology to cyclohexane-carboxylic acid | |
| CN109251168B (en) | Method for preparing pyridine-2-formic acid by using 2-OP rectification residues | |
| CN102010345A (en) | Method for preparing D-phenylalanine through dynamic kinetic resolution | |
| CN107382772B (en) | Process for synthesizing high-purity dodecanitrile by pressure catalysis | |
| CN113372306A (en) | Preparation method of 2, 5-furandimethanol di-tert-butyl ether | |
| CN102344378B (en) | Amino alcohol preparation method using aqueous amino acid | |
| CN114478446B (en) | Method for preparing chromogen III by converting D-acetamido glucose | |
| CN108203455B (en) | Method for preparing finasteride by deiodinating dihydrofinasteride iodide | |
| CN110305083B (en) | Process for preparing 5-chloromethyl furfural from fructose | |
| CN106119307B (en) | Preparation method of alpha-ketoglutaric acid | |
| CN106749131B (en) | Racemization prepares ramelteon intermediate method | |
| CN108147988A (en) | A kind of preparation method of high chiral purity lactam compound | |
| CN106699638B (en) | A kind of preparation method of argatroban intermediate | |
| Jiang et al. | Pd (II)/Lewis Acid Catalyzed Intramolecular Oxidative C− H Amination to Construct Carbazoles with Dioxygen | |
| CN106380439A (en) | A Pd/C reduction method adopting water as a solvent for preparing indole-2-carboxylic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |