CN108383776A - It is a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct - Google Patents
It is a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct Download PDFInfo
- Publication number
- CN108383776A CN108383776A CN201810406721.0A CN201810406721A CN108383776A CN 108383776 A CN108383776 A CN 108383776A CN 201810406721 A CN201810406721 A CN 201810406721A CN 108383776 A CN108383776 A CN 108383776A
- Authority
- CN
- China
- Prior art keywords
- triacetonamine
- acetone
- synthesis
- product
- ammonia
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to triacetonamine synthesis technology fields, and in particular to a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct.Its main technical schemes into reaction kettle that is, be added acetone, synthesis triacetonamine process byproduct and catalyst successively；Stirring is started, and heats reaction kettle temperature to 45 65 DEG C；Lead to ammonia into reaction kettle, and controls 60 75 DEG C of its kettle temperature；Reaction kettle kettle temperature is kept for 36 hours at 60 75 DEG C；Temperature lowering water is opened, kettle temperature is made to be less than 45 DEG C；Stop stirring, standing after 15 30 minutes, triacetonamine crude product is obtained through treatment process；Crude product enters rectifying column through processing, is rectifying to obtain high-purity triacetonamine product.This using acetone and synthesis triacetonamine process byproduct prepare triacetonamine have the characteristics that process conditions simply, be conveniently operated and with short production cycle quick from raw material to product.
Description
Technical field
The present invention relates to belong to triacetonamine synthesis technology field, and in particular to a kind of to utilize acetone and synthesis 3 third
Ketoamine process byproduct prepares triacetonamine.
Background technology
Entitled 2,2,6, the 6- tetramethylpiperidone of triacetonamine chemistry, is a kind of important hindered amine light stabilizer intermediate
And medicine intermediate, especially in hindered amine light stabilizer field, triacetonamine be hindered amine light stabilizer piperidine derivative only
One parent nucleus is the important source material for synthesizing tetramethylpiperidinol, tetramethyl piperidine amine, polymerization inhibitor 702.The synthetic method of triacetonamine
Mainly there are one-step method and two-step method.
One-step method uses acetone and ammonia for raw material, and triacetonamine is synthesized under acidic catalyst effect.One-step method yield compared with
Two-step method is relatively low, but catalyst is cheap and easily-available, raw material is easy recovery, has larger cost advantage compared with two-step method.One
Footwork synthesis triacetonamine process will produce serial by-product, including isopropylidene acetone, diacetone alcohol, diacetonamine, acetonines,
Dimer, tripolymer and the dimer of the acetone such as phorone and the ammonia products of tripolymer.In addition, since technique cannot be simultaneously
The optimal yield condition for matching differential responses starting material, causes yield losses considerable；It is above-mentioned in the high area of some fuel costs
Being formed by by-product can use as fuel oil, not only cause greatly waste, more important is can cause environmental pollution.
Two-step method is first using acetone and ammonia as intermediates such as Material synthesis diacetone alcohol, acetonines, phorone, then again in
Mesosome, acetone, ammonia are Material synthesis triacetonamine：Added as raw material using phorone and liquefied ammonia as disclosed in patent US3943139
Triacetonamine is synthesized under hot pressurized conditions, patent US3960875 is disclosed with acetonines and excessive acetone or acetone and two
The mixture of pyruvic alcohol is Material synthesis triacetonamine.In the technique of above-mentioned synthesis triacetonamine, reaction raw materials phorone, dipropyl
Keto-alcohol, acetonines there is synthesis with detach that difficulty, step is long, the higher defect of production cost.
Invention content
It is an object of the invention to provide a kind of triacetonamine is prepared using acetone and synthesis triacetonamine process byproduct
Technique.
Technical solution is used by realizing the object of the invention：
A kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct, specific process step is：
Acetone, synthesis triacetonamine process byproduct and catalyst is added in the first step into reaction kettle successively；
Second step starts stirring, and heats the reaction kettle temperature to 45-65 DEG C；
Third walks, and ammonia is led into the reaction kettle, and control 60-75 DEG C of kettle temperature；
4th step, the reaction kettle kettle temperature are kept for 3-6 hours at 60-75 DEG C；
5th step, opens temperature lowering water, and the kettle temperature is made to be less than 45 DEG C；
6th step obtains triacetonamine crude product through treatment process；
7th step, crude product enter rectifying column through processing, are rectifying to obtain high-purity triacetonamine product.
It constitutes in the above-mentioned technique for preparing triacetonamine：
--- in the first step, synthesis triacetonamine process byproduct is generated by Material synthesis triacetonamine process of acetone
Serial by-product；The series by-product includes that isopropylidene acetone, diacetone alcohol, diacetonamine, acetonines or phorone are constituted
Acetone dimer, tripolymer and dimer or tripolymer ammonia products, these by-products are in triacetonamine crude product essence
Process processed can be separated and individually storage is handled；
--- the catalyst in the first step is lewis acid substance；Including homogeneous catalyst and heterogeneous catalysis,
The ammonium salt or amine salt of phase catalyst such as hydrochloric acid, sulfuric acid, nitric acid, organic carboxyl acid, organic sulfonic acid and above-mentioned acid, heterogeneous catalysis
Such as acid-exchange resin, acidic molecular sieve and their doping vario-property body；
--- the amount of catalyst is the 1% to 10% of the synthesis triacetonamine process byproduct weight in the first step, preferably
It is 4.0% to 6.0%.
--- the ammonia in the third step is one or both of liquefied ammonia or gas ammonia, and amine component is free of in the ammonia；
--- the treatment process in the 6th step includes
Its alkalinity of 1.0 to 1.2 times of alkali metal hydroxides or alkaline earth metal hydroxide that weight is homogeneous catalyst is added
More than the alkaline matter of ammonium hydroxide, stop the split-phase processing after 15-30 minutes of stirring, standing；Or
For heterogeneous catalysis, catalyst and crude product liquid are detached using filter, filter selects duct type, basket
Formula, filter stick formula, press filtration, filter plate or filter bag type are, it is preferable to use filter candle filter；
--- it is preferable to use NaOH for the alkaline matter.
A kind of technique preparing triacetonamine using acetone and synthesis triacetonamine process byproduct provided by the present invention
Compared with prior art, it has the following advantages：It is directly applied mechanically using one-step method, is reacted after acetone and by-product are mixed in proportion
Individually being applied mechanically compared to one-step method has the characteristics that process conditions are simple；It applies mechanically compared to two-step method and individually, has process conditions simple
It is single, be conveniently operated and the quick feature with short production cycle from raw material to product.
Specific implementation mode
Below by specific implementation mode to preparing triacetonamine using acetone and synthesis triacetonamine process byproduct
Technique is described in further detail：
Embodiment 1：
Acetone 3200kg, by-product 800kg are added into reaction kettle for the first step；
Ammonium nitrate 32kg is added into reaction kettle for second step；
Third walks, and opens stirring, heating kettle temperature is to 45 DEG C；
4th step leads to liquefied ammonia 120kg into kettle, controls 62.5 DEG C of kettle temperature；
5th step, kettle temperature are kept for 5 hours at 62.5 DEG C；
6th step, opens temperature lowering water, and kettle temperature is made to be reduced to 45 DEG C；
7th step puts into NaOH 32kg, stirs 30 minutes and stops, standing 30 minutes, it is thick to obtain triacetonamine after separating water into
Product；Become through gas chromatographic analysis group：Acetone 20.80%, isopropylidene acetone 21.17%, diacetone alcohol 2.12%, diacetonamine
1.67%, acetonines 1.04%, phorone 0.12%, triacetonamine 43.70%, other components 9.38%；
8th step, crude product enter rectifying column, are rectifying to obtain high-purity triacetonamine product, triacetonamine content is through gas-chromatography point
Analysis is 98.01%.
Embodiment 2：
Acetone 3200kg, by-product 800kg are added into reaction kettle for the first step；
Second step, the addition FeCkg into reaction kettle3Processed cation ion exchange resin 32kg；
Third walks, and opens stirring, heating kettle temperature is to 50 DEG C；
4th step leads to liquefied ammonia 120kg into kettle, controls 65 DEG C of kettle temperature；
5th step, kettle temperature are kept for 6 hours at 65 DEG C；
6th step, opens temperature lowering water, and kettle temperature is made to be reduced to 45 DEG C；
7th step stops stirring, and stands 30 minutes, and filtering detaches catalyst with kettle liquid, obtains triacetonamine crude product；Through gas phase color
Spectrum analysis group becomes：Acetone 24.20%, isopropylidene acetone 27.69%, diacetone alcohol 2.70%, diacetonamine 1.32%, acetonines
1.22%, phorone 0.14%, triacetonamine 35.4%, other components 7.33%；
8th step, crude product enter rectifying column, are rectifying to obtain high-purity triacetonamine product, triacetonamine content is through gas-chromatography point
Analysis is 98.21%.
Embodiment 3：
Acetone 2400kg, by-product 1600kg are added into reaction kettle for the first step；
Ammonium nitrate 80kg is added into reaction kettle for second step；
Third walks, and opens stirring, heating kettle temperature is to 45 DEG C；
4th step leads to liquefied ammonia 110kg into kettle, controls 62.5 DEG C of kettle temperature；
5th step, kettle temperature are kept for 5 hours at 62.5 DEG C；
6th step, opens temperature lowering water, and kettle temperature is made to be reduced to 45 DEG C；
7th step puts into NaOH 88kg, stirs 30 minutes and stops, standing 30 minutes, it is thick to obtain triacetonamine after separating water into
Product；Become through gas chromatographic analysis group：Acetone 3.67%, isopropylidene acetone 4.69%, diacetone alcohol 3.79%, diacetonamine
5.73%, acetonines 23.68%, phorone 0.15%, triacetonamine 43.7%, other components 14.59%；
8th step, crude product enter rectifying column, are rectifying to obtain high-purity triacetonamine product, triacetonamine content is through gas-chromatography
Analysis is 97.89%.
Embodiment 4
Acetone 2400kg, by-product 1600kg are added into reaction kettle for the first step；
Second step, the addition FeCkg into reaction kettle3Processed cation ion exchange resin 80kg；
Third walks, and opens stirring, heating kettle temperature is to 50 DEG C；
4th step leads to liquefied ammonia 110kg into kettle, controls 65 DEG C of kettle temperature；
5th step, kettle temperature are kept for 6 hours at 65 DEG C；
6th step, opens temperature lowering water, and kettle temperature is made to be reduced to 45 DEG C；
7th step stops stirring, and stands 30 minutes, and filtering detaches catalyst with kettle liquid, obtains triacetonamine crude product；Through gas phase color
Spectrum analysis group becomes：Acetone 19.88%, isopropylidene acetone 5.34%, diacetone alcohol 2.79%, diacetonamine 4.37%, acetonines
13.09%, phorone 0.11%, triacetonamine 37.50%, other components 16.93%；
8th step, crude product enter rectifying column, are rectifying to obtain high-purity triacetonamine product, triacetonamine content is through gas-chromatography point
Analysis is 97.91%.
Embodiment 5：
Acetone 2000kg, by-product 2000kg are added into reaction kettle for the first step；
Ammonium nitrate 120kg is added into reaction kettle for second step；
Third walks, and opens stirring, heating kettle temperature is to 45 DEG C；
4th step leads to liquefied ammonia 100kg into kettle, controls 62.5 DEG C of kettle temperature；
5th step, kettle temperature are kept for 5 hours at 62.5 DEG C；
6th step, opens temperature lowering water, and kettle temperature is made to be reduced to 45 DEG C；
7th step puts into NaOH 144kg, stirs 30 minutes and stops, standing 30 minutes, it is thick to obtain triacetonamine after separating water into
Product become through gas chromatographic analysis group：Acetone 12.63%, isopropylidene acetone 17.23%, diacetone alcohol 2.57%, diacetonamine
2.36%, acetonines 25.39%, phorone 0.14%, triacetonamine 29.74%, other components 19.94%；
8th step, crude product enter rectifying column, are rectifying to obtain high-purity triacetonamine product, triacetonamine content is through gas-chromatography point
Analysis is 97.42%.
Embodiment 6：
Acetone 2000kg, by-product 2000kg are added into reaction kettle for the first step；
Second step, the addition FeCkg into reaction kettle3Processed cation ion exchange resin 120kg；
Third walks, and opens stirring, heating kettle temperature is to 50 DEG C；
4th step leads to liquefied ammonia 100kg into kettle, controls 65 DEG C of kettle temperature；
5th step, kettle temperature are kept for 6 hours at 65 DEG C；
6th step, opens temperature lowering water, and kettle temperature is made to be reduced to 45 DEG C；
7th step stops stirring, and stands 30 minutes, and filtering detaches catalyst with kettle liquid, triacetonamine crude product is obtained, through gas phase color
Spectrum analysis group becomes：Acetone 15.90%, isopropylidene acetone 21.44%, diacetone alcohol 2.01%, diacetonamine 2.14%, acetonines
11.93%, phorone 0.09%, triacetonamine 25.97%, other components 20.52%；
8th step, crude product enter rectifying column, are rectifying to obtain high-purity triacetonamine product, triacetonamine content is through gas-chromatography
Analysis is 97.45%.
The technique of triacetonamine is prepared using acetone and synthesis triacetonamine process byproduct above-mentioned, wherein
--- heating kettle temperature is to 45-65 DEG C：It is exothermic reaction to fill ammonia process, in order to make to fill ammonia after to reach reaction as early as possible suitable
Temperature, kettle temperature need to be heated to 45-65 DEG C, heat temperature raising is also wanted after then filling ammonia less than 45 DEG C, then fill ammonia knot more than 65 DEG C
Beam can overtemperature；
--- 60-75 DEG C of kettle temperature of control：It is most strongly active in order to allow catalyst to have during the reaction, fully reacts, temperature
It is too low or excessively high can all prevent the activity of catalyst from playing to best；
--- kettle temperature is kept for 3-6 hours at 60-75 DEG C：Reaction duration plays the yield of product very crucial effect --- and it is anti-
It is low to have little time reaction, product yield for short, raw material between seasonable, and the reaction time is long, product can be converted to by-product, in order to make to react
It is few to the more by-products of product, so the reaction time was at 3-6 hours；
--- temperature lowering water is opened, kettle temperature is made to be less than 45 DEG C：Because after reaction, also most of acetone unreacted, temperature are excessively high
It can make acetone volatilization loss, so cooling to the lower temperature of acetone volatilization in the shortest time, reduce the loss of acetone；
--- stop stirring, stands 15-30 minutes：There is water generation in reaction, stands 15-30 minutes, make water and 3 third enough
Ketoamine crude product is layered, and triacetonamine crude product is can be obtained after moisture is fallen.
--- synthesis triacetonamine process generate serial by-product include isopropylidene acetone, diacetone alcohol, diacetonamine,
Dimer, tripolymer and the dimer of the acetone such as acetonines, phorone or the ammonia products of tripolymer, these by-products are three
Acetone amine crude product refining process can be separated and individually storage is handled, therefore be easy to use；
--- the homogeneous catalyst includes the ammonium salt of hydrochloric acid, sulfuric acid, nitric acid, organic carboxyl acid, organic sulfonic acid and above-mentioned acid
Or amine salt, it may be incorporated for acetone and synthesize in the technique that triacetonamine process byproduct prepares triacetonamine；And including
Heterogeneous catalysis as acid-exchange resin, acidic molecular sieve and their doping vario-property body are constituted can be used for
Acetone and synthesis triacetonamine process byproduct are prepared in the technique of triacetonamine.
Claims (7)
1. a kind of preparing triacetonamine using acetone and synthesis triacetonamine process byproduct, specific step of preparation process includes：
Acetone, synthesis triacetonamine process byproduct and catalyst is added in the first step into reaction kettle successively；
Second step starts stirring, and heats the reaction kettle temperature to 45-65 DEG C；
Third walks, and ammonia is led into the reaction kettle, and control 60-75 DEG C of kettle temperature；
4th step, the reaction kettle kettle temperature are kept for 3-6 hours at 60-75 DEG C；
5th step, opens temperature lowering water, and the kettle temperature is made to be less than 45 DEG C；
6th step obtains triacetonamine crude product through treatment process；
7th step, crude product enter rectifying column through processing, are rectifying to obtain high-purity triacetonamine product.
2. preparation process as described in claim 1, it is characterised in that：In the first step, triacetonamine process by-product is synthesized
Object is the serial by-product generated as Material synthesis triacetonamine process using acetone；The series by-product includes the dimerization of acetone
The ammonia products of body, tripolymer and dimer or tripolymer, the by-product can be detached in triacetonamine crude product refining process
Out and individually storage is handled.
3. preparation process as described in claim 1, it is characterised in that：Catalyst in the first step is Louis's acids object
Matter；Including homogeneous catalyst and heterogeneous catalysis：Homogeneous catalyst such as hydrochloric acid, sulfuric acid, nitric acid, organic carboxyl acid, organic sulfonic acid
And the ammonium salt or amine salt of above-mentioned acid, heterogeneous catalysis such as acid-exchange resin, acidic molecular sieve and they mix
Miscellaneous modified body.
4. preparation process as described in claim 1, it is characterised in that：The amount of catalyst is the synthesis three in the first step
The 1% to 10% of acetone amine process byproduct weight, preferably 4.0% to 6.0%.
5. preparation process as described in claim 1, it is characterised in that：Ammonia in the third step is one in liquefied ammonia or gas ammonia
Kind or two kinds, amine component is free of in the ammonia.
6. preparation process as described in claim 1, it is characterised in that：Treatment process in 6th step includes
Its alkalinity of 1.0 to 1.2 times of alkali metal hydroxides or alkaline earth metal hydroxide that weight is homogeneous catalyst is added
More than the alkaline matter of ammonium hydroxide, stop the split-phase processing after 15-30 minutes of stirring, standing；Or
For heterogeneous catalysis, catalyst and crude product liquid are detached using filter, filter selects duct type, basket
Formula, filter stick formula, press filtration, filter plate or filter bag type are, it is preferable to use filter candle filter.
7. preparation process as claimed in claim 6, which is characterized in that it is preferable to use NaOH for the alkaline matter.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810406721.0A CN108383776A (en) | 2018-05-01 | 2018-05-01 | It is a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810406721.0A CN108383776A (en) | 2018-05-01 | 2018-05-01 | It is a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108383776A true CN108383776A (en) | 2018-08-10 |
Family
ID=63066429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810406721.0A Pending CN108383776A (en) | 2018-05-01 | 2018-05-01 | It is a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108383776A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3663284A1 (en) | 2018-12-07 | 2020-06-10 | Evonik Operations GmbH | Improved method for the preparation of triacetonamine |
| EP3750877A1 (en) | 2019-06-13 | 2020-12-16 | Evonik Operations GmbH | Method for preparing triacetone amine and 2,2,4,6-tetramethylpiperidine |
| CN113999165A (en) * | 2021-11-29 | 2022-02-01 | 利安隆凯亚(河北)新材料有限公司 | Method for efficiently utilizing byproducts in triacetonamine synthesis process |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960875A (en) * | 1973-06-29 | 1976-06-01 | Ciba-Geigy Corporation | Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine |
| CN103664745A (en) * | 2012-09-07 | 2014-03-26 | 赢创工业集团股份有限公司 | Method for preparing and treating triacetonamine-containing reaction mixture |
| CN106866503A (en) * | 2017-02-23 | 2017-06-20 | 武汉理工大学 | A kind of method that low temperature liquid phase reaction fixed bed continuously synthesizes triacetonamine |
-
2018
- 2018-05-01 CN CN201810406721.0A patent/CN108383776A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960875A (en) * | 1973-06-29 | 1976-06-01 | Ciba-Geigy Corporation | Process for the preparation of 2,2,6,6-tetramethyl-4-oxopiperidine |
| CN103664745A (en) * | 2012-09-07 | 2014-03-26 | 赢创工业集团股份有限公司 | Method for preparing and treating triacetonamine-containing reaction mixture |
| CN106866503A (en) * | 2017-02-23 | 2017-06-20 | 武汉理工大学 | A kind of method that low temperature liquid phase reaction fixed bed continuously synthesizes triacetonamine |
Non-Patent Citations (3)
| Title |
|---|
| 俞俊棠: "《抗生素生产设备》", 31 October 1994 * |
| 全民强等: "阳离子交换树脂催化三丙酮胺的合成", 《华东理工大学学报（自然科学版）》 * |
| 隋昭德等: "《光稳定剂及其应用技术》", 31 January 2010 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3663284A1 (en) | 2018-12-07 | 2020-06-10 | Evonik Operations GmbH | Improved method for the preparation of triacetonamine |
| US10807954B2 (en) | 2018-12-07 | 2020-10-20 | Evonik Operations Gmbh | Method for preparing triacetone amine |
| EP3750877A1 (en) | 2019-06-13 | 2020-12-16 | Evonik Operations GmbH | Method for preparing triacetone amine and 2,2,4,6-tetramethylpiperidine |
| EP3750876A1 (en) | 2019-06-13 | 2020-12-16 | Evonik Operations GmbH | Method for preparing triacetone amine, 2,2,4,6-tetramethylpiperidine and/or the salts of 2,2,4,6-tetramethylpiperidine |
| CN113999165A (en) * | 2021-11-29 | 2022-02-01 | 利安隆凯亚(河北)新材料有限公司 | Method for efficiently utilizing byproducts in triacetonamine synthesis process |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108383776A (en) | It is a kind of to prepare triacetonamine using acetone and synthesis triacetonamine process byproduct | |
| CN106045834B (en) | A kind of preparation method of ambrotone | |
| CN100395243C (en) | Improved systhesizing process for dicyclohexyl-18-crown-6 | |
| CN117209361B (en) | Bisphenol F preparation method | |
| CN108484482A (en) | A method of preparing triacetonamine using synthesis triacetonamine process byproduct | |
| CN101857550B (en) | Method for producing 6-aminocaproic acid hydrochloride and 6-aminocaproic acid by using nylon-6 waste through depolymerization | |
| CN106397481A (en) | Synthesis method of triethyl phosphonoacetate | |
| CN101844992B (en) | Preparation process of Beta lactamine | |
| CN102050725A (en) | Method for preparing Alpha-keto-phenylalanine calcium | |
| CN107879987A (en) | A kind of preparation method of 2,3,5,6 Tetramethylpyrazine | |
| CN110590601B (en) | Synthesis method of malononitrile | |
| CN111808129A (en) | Preparation method of trimethylsilanol | |
| CN102060816A (en) | Synthesis method of gamma-nonalactone | |
| CN109836344B (en) | Method for producing glycine by organic solvent | |
| CN102030631A (en) | Method for synthesizing alpha-ketoleucine calcium | |
| CN109438360B (en) | Preparation method of creatinine | |
| CN113666807A (en) | Preparation method of 1, 1-diethoxypropane | |
| CN101723816B (en) | Method for preparing 2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-yl)-but-2-enal | |
| CN113292597B (en) | Method for preparing triethyl phosphate compound by recovering sodium diethylphosphate and ethyl chloride | |
| JPH0273033A (en) | Production of 4, 4-dimethyl-1-(p-chlorophenyl) pentane-3-one | |
| CN108069897B (en) | Method for synthesizing nicotinic acid by using carbon dioxide | |
| CN108017671A (en) | The method of phosphorous acid glycine synthesizing glyphosate | |
| CN109867608A (en) | A kind of process for cleanly preparing of glycine co-producing potassium chloride | |
| CN114315577A (en) | Synthesis method of 2-ethoxymethylene-4, 4-difluoroacetoacetic acid ethyl ester | |
| SU891631A1 (en) | Method of producing methacrylic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180810 |