CN109369423A - The preparation method of 3- ethoxy propylamine - Google Patents
The preparation method of 3- ethoxy propylamine Download PDFInfo
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- CN109369423A CN109369423A CN201811545962.XA CN201811545962A CN109369423A CN 109369423 A CN109369423 A CN 109369423A CN 201811545962 A CN201811545962 A CN 201811545962A CN 109369423 A CN109369423 A CN 109369423A
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- catalyst
- ethoxy
- preparation
- hydrogenation
- propionitrile
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- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- DCWQZPJHHVLHSV-UHFFFAOYSA-N 3-ethoxypropanenitrile Chemical compound CCOCCC#N DCWQZPJHHVLHSV-UHFFFAOYSA-N 0.000 claims abstract description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000019441 ethanol Nutrition 0.000 claims abstract description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 230000006837 decompression Effects 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910000570 Cupronickel Inorganic materials 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 238000007599 discharging Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000012797 qualification Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- ZSTYQALWKOGXOV-UHFFFAOYSA-N 2-methoxy-2-methylpropan-1-amine Chemical compound COC(C)(C)CN ZSTYQALWKOGXOV-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- -1 primary amine compound Chemical class 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation method of 3- ethoxy propylamine, preparation steps are as follows: 1) catalyst A, ethyl alcohol is added in reactor；2) temperature of reactor is controlled, acrylonitrile is added dropwise；3) the 3- ethoxy propionitrile that content is greater than 97% is made；4) 3- ethoxy propionitrile made from is in catalyst B, hydrogen, in the presence of inhibitor, hydrogenation；5) after hydrogenation qualification, then the finished product to obtain content and be greater than 99.5% is distilled through vacuum decompression.Preparation method selectivity is high, in the process excessive ethyl alcohol, catalyst A, B can recovery, further decrease production cost, reduce waste liquid discharging amount.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of preparation method of 3- ethoxy propylamine.
Background technique
3- ethoxy propylamine, English: 3-Ethoxy-1-propanamine, molecular formula: C5H13NO, No. CAS: 6291-
85-6 is colourless transparent liquid, is dissolved in water, there is stronger corrosivity.
3- ethoxy propylamine is a kind of primary amine compound that purposes is relatively broad.He may act as synthesis disperse dyes
The red intermediate of 90#, but as a kind of external novel corrosion inhibitor introduced and ionization emulsifier petrochemical industry gradually
It promotes and applies, now in integrated circuit, the field OLED, mobile phone display screen is also widely used, and market is widely used.
Nitrile is made under catalyst A effect using with ethyl alcohol and acrylonitrile in company, and nitrile is urged under the action of catalyst again
Change one step of hydrogenation and obtain crude product, qualified products is obtained by rectifying, the total selectivity of two step of production technology can achieve 92%, three
It is useless less, it is high income, at low cost, basic no three wastes generates, and belongs to green clean manufacturing.
Summary of the invention
The object of the present invention is to provide a kind of simple process and the preparation methods of environmental-friendly 3- ethoxy propylamine.
In order to solve the above technical problems, the technical solution adopted by the present invention is that: a kind of 1. preparation sides of 3- ethoxy propylamine
Method, which comprises the following steps:
1) catalyst A, ethyl alcohol are added in reactor；
2) temperature of reactor is controlled, acrylonitrile is added dropwise；
3) the 3- ethoxy propionitrile that content is greater than 97% is made after keeping the temperature a period of time；
4) gained 3- ethoxy propionitrile is in catalyst B, hydrogen, in the presence of inhibitor, gives certain temperature and pressure hydrogenation；
5) after hydrogenation is qualified, then through vacuum decompression finished product is distilled to obtain.
Further, the molar ratio of the ethyl alcohol and acrylonitrile is 1.0 ~ 1.5:1.
Further, the catalyst A is that sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, highly basic are multiple
Close one of catalyst, aluminium oxide or two kinds of mixtures.
Further, the dropwise addition acrylonitrile temperature is 20 ~ 80 degree, preferably 30 ~ 60 degree.
Further, the catalyst B is that one of Raney's nickel, thunder Buddhist nun cobalt, cupro-nickel, nickel aluminum catalyst or two kinds are mixed
Object is closed by the modified gained of strong alkaline substance；The strong alkaline substance is sodium hydroxide, potassium hydroxide, ammonium hydroxide, liquefied ammonia, phosphoric acid hydrogen
One of disodium or two kinds of mixtures, the strong alkaline substance dosage are the 1--5% of catalyst B weight.
Further, the inhibitor is one of sodium hydroxide, potassium hydroxide, ammonium hydroxide, liquefied ammonia, disodium hydrogen phosphate
Or two kinds of mixtures.
Further, the hydrogenation temperature is 70-150 degree.
Further, the hydrogenation pressure is 3.0-6.0Mpa.
Further, the additional amount of the catalyst A is the 0.2% -2% of reaction solution total weight, catalyst B's
Additional amount is the 2% -10% of reaction solution total weight.
The reaction equation of above-mentioned reaction process is as follows:
Technical problem solved by the present invention is nitrile is made in 1. ethyl alcohol and acrylonitrile under catalyst A effect, catalyst A is highly basic
Property catalyst, can be with rapid synthesis 3- ethoxy propionitrile, selectivity is greater than 97%, and catalyst A can be applied repeatedly；2. hydrogen
Change catalyst B, is hydrogenated in the presence of inhibitor, hydrogen, selectively reach 95%.
The beneficial effects of the present invention are:
1, the addition of catalyst A can greatly improve reaction speed, improve product selectivity, obtain the 3- ethoxy-c of high-content
Nitrile, and catalyst A can be generated without the three wastes in the process with recovery.
2, catalyst B is modified through super-alkaline substance, and catalyst surface lattice changes, and catalyst is to hydrogen adsorption capacity
Enhancing, so, the available effective control of deamination by-product, to improve product selectivity.
Specific embodiment:
Below by specific embodiment, the invention will be further described, but the present invention should not be limited only to these examples.
Embodiment 1:
200g ethyl alcohol is taken, 1.8g sodium ethoxide is added in the four-hole bottle of 500ml, opens stirring, and 210g is added dropwise with constant pressure funnel
Heat release is added dropwise in acrylonitrile, and temperature slowly rises, and controls at 45 DEG C, after drop finishes, after heat preservation 3 hours, and GC analysis, ethyl alcohol: 1.1%,
Acrylonitrile: 0.3%, 3- ethoxy propionitrile: 98.3%.
20g catalyst Raney's nickel is added in the potassium hydroxide solution of 100g0.5% and stirs two hours, then topples over upper layer
Clear liquid, gained catalyst is cleaned after 2 times with 100ml ionized water obtains modified Raney's nickel catalyst B, gained catalyst B and upper step
Obtained 3- ethoxy propionitrile is added in autoclave, nitrogen 0.1MPa, 0.2MPa, 0.3MPa displacement 3 times, then hydrogen
After 0.1MPa, 0.2MPa, 0.3MPa are replaced 3 times, 80g liquefied ammonia is poured, 85 degree is warming up to, pours hydrogen, in the pressure of 3.6Mpa
Hydrogen is not eaten in lower hydrogenation substantially after 5 hours, sampling, GC analysis: 3- ethoxy propionitrile 0.02%, 3- ethoxy propylamine 94.6%.Then
It is cooling, inhibitor liquefied ammonia is laid down to another autoclave, can be covered and be used lower batch.It is then allowed to stand, filters, rectifying obtains
The 3- ethoxy propylamine finished product of 375g99.7%, yield 92%.
Embodiment 2:
200g ethyl alcohol is taken, 0.82g sodium methoxide is added in the four-hole bottle of 500ml, opens stirring, and 210g is added dropwise with constant pressure funnel
Heat release is added dropwise in acrylonitrile, and temperature slowly rises, and controls at 50 DEG C, after drop finishes, after heat preservation 6 hours, and GC analysis, ethyl alcohol: 2.5%,
Acrylonitrile: 0.5%, 3- ethoxy propionitrile: 96.5%.
20g catalyst thunder Buddhist nun's cobalt be added 100g1.5% disodium phosphate soln in stir two hours, then topple on
Layer clear liquid, gained catalyst is cleaned after 2 times with 100ml ionized water obtains thunder Buddhist nun Co catalysts B, gained catalyst B and upper step obtains
To 3- ethoxy propionitrile be added autoclave in, nitrogen 0.1MPa, 0.2MPa, 0.3MPa replace 3 times, then hydrogen 0.1MPa,
After 0.2MPa, 0.3MPa are replaced 3 times, 60g liquefied ammonia is poured, 150 degree is warming up to, pours hydrogen, the hydrogen under the pressure of 4.0Mpa
Change, do not eat hydrogen substantially after 5 hours, samples, GC analysis: 3- ethoxy propionitrile 0.03%, 3- ethoxy propylamine 92.6%.Then cold
But, inhibitor liquefied ammonia is laid down to another autoclave, can be covered and be used lower batch.It is then allowed to stand, filters, rectifying obtains
The 3- ethoxy propylamine finished product of 367.2g99.5%, yield 90%.
Embodiment 3:
200g ethyl alcohol is taken, 8.2g sodium hydroxide is added in the four-hole bottle of 500ml, is opened stirring, is added dropwise with constant pressure funnel
Heat release is added dropwise in 210g acrylonitrile, and temperature slowly rises, and temperature is controlled at 50 DEG C, after drop finishes, after heat preservation 3 hours, and GC analysis, second
Alcohol: 0.8%, acrylonitrile: 0.6%, 3- ethoxy propionitrile: 98.0%.
20g catalyst Raney's nickel is added in 100g26% ammonia spirit and stirs two hours, gained Raney's nickel catalyst B and upper
It walks obtained 3- ethoxy propionitrile to be added in autoclave, nitrogen 0.1MPa, 0.2MPa, 0.3MPa displacement 3 times, then hydrogen
After 0.1MPa, 0.2MPa, 0.3MPa are replaced 3 times, 70g liquefied ammonia is poured, 90 degree is warming up to, pours hydrogen, in the pressure of 6.0Mpa
Hydrogen is not eaten in lower hydrogenation substantially after 5 hours, sampling, GC analysis: 3- ethoxy propionitrile 0.04%, 3- ethoxy propylamine 93.8%.Then
It is cooling, inhibitor liquefied ammonia is laid down to another autoclave, can be covered and be used lower batch.It is then allowed to stand, filters, rectifying obtains
The 3- ethoxy propylamine finished product of 371g99.5%, yield 91%.
The preparation method of 3- ethoxy propylamine of the present invention is applied in the industrial production, the steps include:
1) by catalyst A, ethyl alcohol investment kettle, acrylonitrile enters head tank, after reacting kettle nitrogen replacement, is not required to heat up, and is added dropwise
Acrylonitrile leans on self-heat generation, is warming up to 30-60 DEG C, drips within 2-8 hours acrylonitrile, and 1-6 hours obtained contents of heat preservation are greater than
The reaction solution of 97% 3- ethoxy propionitrile；
2) after above-mentioned reaction solution being removed catalyst A, autoclave is put into, catalyst B is added, nitrogen displacement adds after hydrogen displacement
Enter a small amount of inhibitor, after heating, be passed through hydrogen, makes Hydrogen Vapor Pressure to 3.0-6.0MPa, given birth to controlled at 70-150 DEG C of reaction
At 3- ethoxy propylamine crude product, then it is rectifying to obtain finished product, product content is greater than 99.5%.
Claims (9)
1. a kind of preparation method of 3- ethoxy propylamine, which comprises the following steps:
1) catalyst A, ethyl alcohol are added in reactor；
2) temperature of reactor is controlled, acrylonitrile is added dropwise；
3) the 3- ethoxy propionitrile that content is greater than 97% is made after keeping the temperature a period of time；
4) gained 3- ethoxy propionitrile is in catalyst B, hydrogen, in the presence of inhibitor, gives certain temperature and pressure hydrogenation；
5) after hydrogenation is qualified, then through vacuum decompression finished product is distilled to obtain.
2. the preparation method of 3- ethoxy propionitrile according to claim 1, it is characterised in that: the ethyl alcohol and acrylonitrile
Molar ratio is 1.0 ~ 1.5:1.
3. the preparation method of 3- ethoxy propionitrile according to claim 1, it is characterised in that: the catalyst A is hydrogen
One of sodium oxide molybdena, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, highly basic composite catalyst, aluminium oxide or two kinds of mixing
Object.
4. the preparation method of 3- ethoxy propionitrile according to claim 1, it is characterised in that: the dropwise addition acrylonitrile temperature
Degree is 20 ~ 80 degree, preferably 30 ~ 60 degree.
5. the preparation method of 3- ethoxy propylamine according to claim 1, it is characterised in that: the catalyst B is thunder
One of Buddhist nun's nickel, thunder Buddhist nun cobalt, cupro-nickel, nickel aluminum catalyst or two kinds of mixtures are by the modified gained of strong alkaline substance；It is described strong
Alkaline matter is one of sodium hydroxide, potassium hydroxide, ammonium hydroxide, liquefied ammonia, disodium hydrogen phosphate or two kinds of mixtures, the highly basic
Property substance dosage be catalyst B weight 1--5%.
6. the preparation method of 3- ethoxy propylamine according to claim 1, it is characterised in that: the inhibitor is hydrogen-oxygen
Change one of sodium, potassium hydroxide, ammonium hydroxide, liquefied ammonia, disodium hydrogen phosphate or two kinds of mixtures.
7. the preparation method of 3- ethoxy propylamine according to claim 1, it is characterised in that: the hydrogenation temperature is
70-150 degree.
8. the preparation method of 3- ethoxy propylamine according to claim 1, it is characterised in that: the hydrogenation pressure is
3.0-6.0Mpa。
9. the preparation method of 3- ethoxy propylamine according to claim 1, it is characterised in that: the catalyst A's
Additional amount is the 0.2% -2% of reaction solution total weight, and the additional amount of catalyst B is the 2% -10% of reaction solution total weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811545962.XA CN109369423B (en) | 2018-12-18 | 2018-12-18 | Preparation method of 3-ethoxy propylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811545962.XA CN109369423B (en) | 2018-12-18 | 2018-12-18 | Preparation method of 3-ethoxy propylamine |
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| Publication Number | Publication Date |
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| CN109369423A true CN109369423A (en) | 2019-02-22 |
| CN109369423B CN109369423B (en) | 2021-11-02 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113004171A (en) * | 2021-03-09 | 2021-06-22 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
| CN113563210A (en) * | 2021-07-26 | 2021-10-29 | 山东汉鸿新材料科技有限公司 | Synthesis process of methoxypropylamine |
| CN114276254A (en) * | 2021-12-31 | 2022-04-05 | 万华化学集团股份有限公司 | Synthetic method of 3-methoxypropylamine |
| CN115246778A (en) * | 2022-08-15 | 2022-10-28 | 江苏万盛大伟化学有限公司 | Preparation method of fatty alkoxy propylamine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3372195A (en) * | 1964-05-04 | 1968-03-05 | Dow Chemical Co | Reduction of nitriles to primary amines |
| DE1921467B2 (en) * | 1969-04-26 | 1974-09-19 | Basf Ag, 6700 Ludwigshafen | Process for the catalytic! Hydrogenation of organic compounds |
| DD280963A1 (en) * | 1989-03-29 | 1990-07-25 | Akad Wissenschaften Ddr | METHOD FOR THE PRODUCTION OF HIGH-PURITY BETA-ALKOXYPROPIONITRILES BY CATALYTIC ATTACHMENT OF ALCOHOLS TO ACRYLNITRILE |
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2018
- 2018-12-18 CN CN201811545962.XA patent/CN109369423B/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113004171A (en) * | 2021-03-09 | 2021-06-22 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
| CN113004171B (en) * | 2021-03-09 | 2022-09-16 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
| CN113563210A (en) * | 2021-07-26 | 2021-10-29 | 山东汉鸿新材料科技有限公司 | Synthesis process of methoxypropylamine |
| CN114276254A (en) * | 2021-12-31 | 2022-04-05 | 万华化学集团股份有限公司 | Synthetic method of 3-methoxypropylamine |
| CN114276254B (en) * | 2021-12-31 | 2023-09-19 | 万华化学集团股份有限公司 | Synthesis method of 3-methoxypropylamine |
| CN115246778A (en) * | 2022-08-15 | 2022-10-28 | 江苏万盛大伟化学有限公司 | Preparation method of fatty alkoxy propylamine |
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