CN107118118A - The method that pipelineization continuously produces N n-propyl acetamides - Google Patents
The method that pipelineization continuously produces N n-propyl acetamides Download PDFInfo
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- CN107118118A CN107118118A CN201710384232.5A CN201710384232A CN107118118A CN 107118118 A CN107118118 A CN 107118118A CN 201710384232 A CN201710384232 A CN 201710384232A CN 107118118 A CN107118118 A CN 107118118A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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Abstract
The invention discloses a kind of method that pipelineization continuously produces N n-propyl acetamides, used pipelineization reaction process units includes reaction coil pipe, and the outlet of reaction coil pipe is connected after passing through cooling coil with the import of pressure pan, and the exit of pressure pan is provided with valve；This method comprises the following steps：1), make to be full of acetate esters in reaction coil pipe；2), the temperature that the pressure reacted in coil pipe is charged in 3 ± 0.2MPa, and regulation reaction coil pipe with inert gas is 170~200 DEG C；3), the mixed solution of acetate esters and n-propylamine is entered with certain flow as reaction raw materials and reacted in reaction coil pipe, the reaction solution of gained is flowed into pressure pan after the cooling of cooling coil, when the pressure in pressure pan is higher than 5MPa, opens valve and discharge the reaction solution in pressure pan；4) unreacting material and the alcohol as product are sloughed in the reaction solution distillation, discharged from pressure pan, obtain N n-propyl acetamides.
Description
Technical field
The invention belongs to organic synthesis field, it is related to a kind of method that pipelineization continuously produces N- n-propyl acetamides.
Background technology
N- n-propyl acetamides (CAS：5331-48-6), its molecular formula is C5H11NO, is 101.15 with respect to protonatomic mass, point
Minor structure is as follows：
N- n-propyl acetamides are a kind of important amide-type organic synthesis intermediates, while can also be used as a kind of dissolubility
High boiling solvent that can be good is used in organic synthesis.
That reports at present has following several production methods：
Method 1：Tao Chen,Gaofeng Zeng,Zhiping Lai,Kuowei Huan,Journal of
Membrane Science,2016,515:212-218, it is raw material to inform with ethanol and n-propylamine, Isosorbide-5-Nitrae-dioxane, four
Hydrogen furans or toluene are solvent, Millstein catalyst, potassium tert-butoxide, in the ceramic membrane reactor of palladium/silver, 140-160 DEG C
Reacted 5 hours under reaction condition, according to the difference of reaction dissolvent, yield can reach 52-70%.This method reaction vessel, catalysis
Agent is expensive, and yield is not also high, it is difficult to realize industrial production.
Method 2：Maryam Mirza-Aghayan,Mahdieh Molaee Tavana,Rabah Boukherroub,
Ultrasonics Sonochemistry,2016,29:371-379, is informed using acetic acid and n-propylamine as raw material, with sulfonation also
Former graphene oxide (rGO-SO3H) is catalyst, and under ultrasound condition, is reacted 20 minutes, generates N- n-propyl acetamides,
Its yield is up to 95%.This method high conversion rate, reaction speed is fast, but catalyst preparation is difficult, expensive, and ultrasound is anti-
Answer device complicated.
Method 3：Using ethyl acetate and n-propylamine, (mol ratio is 2.8:1) it is raw material, using sodium methoxide as catalyst, methanol is
Reaction dissolvent, heating reflux reaction 24 hours, 60 DEG C of reflux temperature, cold filtration sodium methoxide, and distill out unreacted raw material
And the ethanol of generation, yield is up to 65% (A1 of US 20120277444).This method reaction condition is gentle, and catalyst is cheap
It is easy to get；But the time is long, yield is low.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of method that pipelineization continuously produces N- n-propyl acetamides.
In order to solve the above-mentioned technical problem, the present invention provides the side that a kind of pipelineization continuously produces N- n-propyl acetamides
Method, used pipelineization reaction process units includes reaction coil pipe, react the outlet of coil pipe by after cooling coil with high pressure
The import of tank is connected, and the exit of pressure pan is provided with valve；
This method comprises the following steps：
1), make to be full of acetate esters in reaction coil pipe；
2) pressure reacted in coil pipe (for pressure in system), is charged to 3 ± 0.2MPa with inert gas (such as nitrogen),
And the temperature in regulation reaction coil pipe is 170~200 DEG C；
3), the mixed solution of acetate esters and n-propylamine as reaction raw materials with certain flow enter in reaction coil pipe in
170~200 DEG C are reacted, and control the flow so that residence time of the mixed solution in reaction coil pipe for 119.5~
627min；
The mol ratio of acetate esters and n-propylamine is 1 in the mixed solution:0.5~2；
The reaction solution of gained is flowed into pressure pan after the cooling of cooling coil, when the pressure in pressure pan is higher than 5MPa
When, open valve and discharge the reaction solution in pressure pan, until pressure drops to same step 2 in pressure pan) in it is set anti-
When answering the pressure in coil pipe, valve is closed；
4) unreacting material (a small amount of unreacting material is sloughed in the reaction solution distillation, discharged from pressure pan；That is, acetic acid esters
Class and n-propylamine) and as the alcohol of product, obtain N- n-propyl acetamides.
The improvement of the method for N- n-propyl acetamides is continuously produced as the pipelineization of the present invention：
Acetate esters are ethyl acetate, methyl acetate or propyl acetate.
Corresponding product is ethanol, methanol, normal propyl alcohol.
The further improvements in methods of N- n-propyl acetamides are continuously produced as the pipelineization of the present invention：
The total measurement (volume) for reacting coil pipe is 251mL, step 3) in the mixed solution of acetate esters and n-propylamine enter reaction tray
Flow during pipe is 0.40~2.10mL/min.
The method that the pipelineization of the present invention continuously produces N- n-propyl acetamides, reaction raw materials are ethyl acetate or acetic acid first
The mixed solution of ester, propyl acetate and n-propylamine, solvent-free, no catalyst.
The present invention specifically includes following steps using reaction unit as described in Figure 1, this method：
(1) ethyl acetate (methyl acetate, propyl acetate) is added in graduated cylinder 1, by system inner valve standard-sized sheet, using big flow velocity
10mL/min makes to be full of ethyl acetate (methyl acetate, propyl acetate) in reaction coil pipe；By residual acetic acid ethyl ester (acetic acid in graduated cylinder
Methyl esters, propyl acetate) reclaim, add the ethyl acetate (methyl acetate, propyl acetate) and n-propylamine as reaction raw materials, acetic acid
The mol ratio of ethyl ester (methyl acetate, propyl acetate) and n-propylamine is 1:0.5-2.
(2) pressure in system is charged to 3 ± 0.2MPa with nitrogen, closes the valve in pressure pan exit.Open oil bath pan,
Design temperature is 170-200 DEG C, opens agitating paddle, and waiting temperature rises to reaction temperature.
(3) flow 0.40-2.10mL/min is set at plunger pump, starts charging reaction.Note at observation pressure pan
Manometric registration, when pressure is higher than 5MPa, opens the valve in pressure pan exit, reaction solution is put into collecting tank, directly
Into pressure pan, pressure drops to 3 ± 0.2MPa, closes the valve in pressure pan exit.
(4) question response raw material after completion of the reaction, adds ethyl acetate (methyl acetate, propyl acetate) in graduated cylinder, makes anti-
Answer and ethyl acetate (methyl acetate, propyl acetate) is full of in coil pipe, turn off pump, valve, oil bath pan, agitating paddle etc. is equipped.
(5) valve in pressure pan exit is opened, the reaction solution in pressure pan is collected.Under normal pressure, distillation removing is a small amount of not
Reaction raw materials and cleaning ethyl acetate (methyl acetate, propyl acetate) etc., you can obtain reaction product N- n-propyl acetamides.
The synthetic reaction equation of the N- n-propyl acetamides of the present invention is as follows：
The present invention be it is a kind of it is solvent-free, continuously produce N- n-propyl second without catalyst, high income, the pipelineization of no coupling product
The method of acid amides.N- n-propyl acetamides are produced using pipeline reaction technology, are similar to piston flow reactor, back-mixing is small；It is raw
Production capacity power is big；Online reacting dose is small, production safety；Equipment investment is small；Product quality is stable；It is suitable for large-scale production.
In summary, the method that pipelineization of the invention continuously produces N- n-propyl acetamides, with following advantage：
1st, reaction is carried out in pipeline reactor, and the institute reacted with pipelineization is advantageous such as：Back-mixing is small；Production capacity
Greatly；Online reacting dose is small, production safety；Equipment investment is small；Product quality is stable.
2nd, react solvent-free, no catalyst is added, and without side reaction, reaction conversion ratio is high, and environmental protection is almost without three
It is useless to produce.
3rd, product and raw material boiling-point difference can be separated away from big by modes such as simple distillations, and post processing is simple.
Brief description of the drawings
The embodiment to the present invention is described in further detail below in conjunction with the accompanying drawings.
Fig. 1 is the process units schematic diagram that pipeline reactor is connected with other equipment.
1- graduated cylinders, 2- plunger pumps, 3- oil bath pans, 4- reaction coil pipes, 5- agitating paddles, 6- cooling coils, 7- pressure pans, 8- is received
Collect tank, 9~11- pressure gauges, 12~14- needle valves, 15- valves.
Embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This：
A kind of pipeline makeup of continuous production N- n-propyl acetamides is put, as shown in figure 1, including graduated cylinder 1, plunger pump 2, oil
Bath 3, reacts coil pipe 4, agitating paddle 5, cooling coil 6, pressure pan 7, collecting tank 8, pressure gauge 9~11, needle valve 12~14, valve
Door 15, the valve 15 is also needle valve.React coil pipe 4 to be located in oil bath pan 3, agitating paddle 5 is provided with oil bath pan 3；Pressure pan 7
On be provided with pressure gauge 11.
Import of the graduated cylinder 1 by plunger pump 2 with reacting coil pipe 4 is connected, between plunger pump 2 and the reaction import of coil pipe 4
On connecting line pressure gauge 9, needle valve 12 are disposed with along flow direction of material；Plunger pump 2 be used for convey reaction raw materials and
The flow velocity of control material.
The outlet of reaction coil pipe 4 is connected with the import of cooling coil 6, the outlet of cooling coil 6 and the import phase of pressure pan 7
Even, the outlet of pressure pan 7 is connected with collecting tank 8；Connecting tube between the outlet of reaction coil pipe 4 and the import of cooling coil 6
Road is provided with pressure gauge 10；On connecting line between the outlet of cooling coil 6 and the import of pressure pan 7 along flow direction of material according to
It is secondary to be provided with needle valve 13, needle valve 14, it is provided with valve on the connecting line between the outlet of pressure pan 7 and collecting tank 8
15。
Pipeline is the stainless steel tubes (internal diameter 2mm) of Ф 3 in pipelineization reaction process units, reacts the long 80m of coil pipe 4, instead
It is 251mL to answer the total measurement (volume) of coil pipe 4.The long 1m of cooling coil 6.
In pipelineization reaction process units, the stabilization of pressure is the stable key factor of maintenance reaction；High pressure is set
The purpose of tank 7 is can be stored temporarily in reaction solution in pressure pan 7, and system is maintained more than certain pressure.As removed
The pressure pan 7, only by the aperture of valve come maintenance system pressure, such as valve opening is too small, then hypertonia in system, even
Generation security incident；As aperture it is too big, then pressure is low in system, and raw material is in high-temperature evaporation, and its saturated vapor pressure is larger, can will instead
Answer liquid to go out reaction coil pipe 4, cause flowing instability.Moreover, such as the not no pressure pan 7, then system stability is very poor, environment temperature
The fluctuation of degree, oil bath temperature etc. all can cause tremendous influence to system.
The effect of cooling coil 6 is to make the near room temperature of reacting liquid temperature, and organic steam can be reduced during kettle etc. is driven
Generation.
Needle valve 12-14 act as pipeline dismantle or need pump be vented etc. during, system each several part can be broken
Drive row processing into used.Valve 12-14 is in open mode in course of normal operation.
What pressure gauge 10 was determined is the terminal pressure (it is reaction pressure to be approximately considered) for reacting coil pipe 4, and pressure gauge 11 is determined
Be pressure pan 6 pressure.
What pressure gauge 9 was determined is the import end pressure for reacting coil pipe 4, and the purpose for determining the pressure is can to monitor reaction tray
The forefront pressure of pipe 4, prevents hypertonia from being caused damage to pump；The data of pressure drop in reaction tray pipe 4 can be obtained.
A kind of method that embodiment 1, pipelineization continuously produce N- n-propyl acetamides, using device shown in Fig. 1, with second
Acetoacetic ester and n-propylamine are raw material, are followed the steps below successively：
(1) ethyl acetate 300mL is added in graduated cylinder 1, by system inner valve (including needle valve 12-14, valve 15) standard-sized sheet,
Make to be full of ethyl acetate in reaction coil pipe 4 using big flow velocity 10mL/min；Remaining ethyl acetate in graduated cylinder 1 is reclaimed, added
The mixed liquor 450mL of ethyl acetate and n-propylamine is as reaction raw materials liquid, and the mol ratio of ethyl acetate and n-propylamine is 1:1.
(2) pressure in system (that is, reacting the pressure in coil pipe 4) is charged to 3MPa (now, pressure gauge 9, pressure with nitrogen
The reading of table 10 is 3MPa), close valve 15.Oil bath pan 3 is opened, design temperature is 170 DEG C, opens agitating paddle 5, waits temperature
Degree rises to reaction temperature.
Remarks explanation：Nitrogen is filled with mode and for example can be：The pipeline after valve 15 is dismantled, and is accessed at this valve 15
Nitrogen cylinder, removes nitrogen cylinder after being charged to setting pressure, reinstalls original pipeline again.
(3) flow 0.40-0.90mL/min is set at plunger pump 2, starts charging reaction.Note observing pressure gauge 11
Registration, when pressure is higher than 5MPa, opens valve 15, reaction solution is put into collecting tank 8, until pressure drops in pressure pan
3MPa, closes valve 15.
(4) reaction of question response raw material is finished after (that is, the reaction raw materials liquid discharge in graduated cylinder 1 is finished), is added in graduated cylinder 1
Ethyl acetate, ethyl acetate enters reaction coil pipe 4 with same setting flow, makes to be full of ethyl acetate in reaction coil pipe 4, so that
All reaction solutions are made to be discharged into pressure pan 7.
All valves (needle valve 12~14, valve 15) in plunger pump 2 and system are turned off, make oil bath pan 3, agitating paddle
5 grades equipment is stopped.
(5) valve 15 is opened, the reaction solution in pressure pan 7 is collected.
After reaction solution in pressure pan 7 and collecting tank 8 is collected, vacuum distillation removing (15torr, 50 DEG C) is not a small amount of anti-
Answer the ethanol of raw material (ethyl acetate, n-propylamine) and cleaning ethyl acetate and generation；It can obtain reaction product N- positive third
Yl acetamide.
Under different flow conditions, reaction yield is as shown in table 1 below：
Table 1,170 DEG C, raw material compares 1:1 reaction result
A kind of method that embodiment 2, pipelineization continuously produce N- n-propyl acetamides,
The mol ratio of ethyl acetate and n-propylamine is 1:0.5；
Flow 0.40-1.00mL/min is set at plunger pump 2,
Remaining is equal to embodiment 1.
Under different flow conditions, reaction yield is as shown in table 2 below：
Table 2,170 DEG C, raw material compares 1:0.5 reaction result
A kind of method that embodiment 3, pipelineization continuously produce N- n-propyl acetamides,
The mol ratio of ethyl acetate and n-propylamine is 1:2；
Flow 0.40-1.00mL/min is set at plunger pump 2；
Remaining is equal to embodiment 1.
Under different flow conditions, reaction yield is as shown in table 3 below：
Table 3,170 DEG C, raw material compares 1:2 reaction results
A kind of method that embodiment 4, pipelineization continuously produce N- n-propyl acetamides；
Design temperature is 200 DEG C；
Flow 0.60-2.10mL/min is set at plunger pump 2；
Remaining is equal to embodiment 1.
Under different flow conditions, reaction yield is as shown in table 4 below：
Table 4,200 DEG C, raw material compares 1:1 reaction result
A kind of method that embodiment 5, pipelineization continuously produce N- n-propyl acetamides,
Design temperature is 185 DEG C；
Flow 0.40-1.40mL/min is set at plunger pump 2；
Remaining is equal to embodiment 1.
Under different flow conditions, reaction yield is as shown in table 4 below：
Table 5,185 DEG C, raw material compares 1:1 reaction result
A kind of method that embodiment 6, pipelineization continuously produce N- n-propyl acetamides, using methyl acetate and n-propylamine as original
Material,
The mol ratio of methyl acetate and n-propylamine is 1:1；
Accordingly, ethyl acetate used in embodiment 1 is made into methyl acetate accordingly；
Remaining is equal to embodiment 1.
Under different flow conditions, reaction yield is as shown in table 6 below：
Table 6,170 DEG C, raw material compares 1:1 reaction result
A kind of method that embodiment 7, pipelineization continuously produce N- n-propyl acetamides, using propyl acetate and n-propylamine as original
Material,
The mol ratio of propyl acetate and n-propylamine is 1:1；
Accordingly, ethyl acetate used in embodiment 1 is made into propyl acetate accordingly；
Remaining is equal to embodiment 1.
Under different flow conditions, reaction yield is as shown in table 7 below：
Table 7,170 DEG C, raw material compares 1:1 reaction result
Comparative example 1,
Step 1) in, in the mixed solution of ethyl acetate and n-propylamine, the mol ratio of ethyl acetate and n-propylamine is 2.8:
1；
Step 2) in, oil bath pan 3 is opened, design temperature is 60 DEG C；
Step 3) in flow velocity it is as described in Table 8.
Remaining is equal to embodiment 1.
Acquired results are as shown in table 8.
(60 DEG C, raw material compares 2.8 for table 8, comparative example 1:1) reaction result
Finally, in addition it is also necessary to it is noted that listed above is only several specific embodiments of the invention.But it is of the invention
Above example is not limited to, there can also be many other equivalent embodiments.One of ordinary skill in the art is public from the present invention
Woollen goods direct derivation opened or other the equivalent embodiments associated, are considered as protection scope of the present invention.
Claims (3)
1. the method that pipelineization continuously produces N- n-propyl acetamides, it is characterized in that：
Used pipelineization reaction process units includes reaction coil pipe (4), and the outlet of reaction coil pipe (4) passes through cooling coil
(6) import afterwards with pressure pan (7) is connected, and the exit of pressure pan (7) is provided with valve (15)；
This method comprises the following steps：
1), make to be full of acetate esters in reaction coil pipe (4)；
2), the pressure reacted in coil pipe (4) be charged to the temperature in 3 ± 0.2MPa, and regulation reaction coil pipe (4) with inert gas
For 170~200 DEG C；
3), the mixed solution of acetate esters and n-propylamine as reaction raw materials with certain flow enter in reaction coil pipe (4) in
170~200 DEG C are reacted, and control the flow, so that residence time of the mixed solution in reaction coil pipe (4) is 119.5
~627min；
The mol ratio of acetate esters and n-propylamine is 1 in the mixed solution:0.5~2；
The reaction solution of gained is flowed into after the cooling of cooling coil (6) in pressure pan (7), when the pressure in pressure pan (7) is higher than
During 5MPa, open valve (15) and discharge the reaction solution in pressure pan (7), until pressure drops to same step in pressure pan (7)
2) in during pressure in set reaction coil pipe (4), valve (15) is closed；
4), unreacting material and the alcohol as product are sloughed in the reaction solution distillation of discharge from pressure pan (7), obtain N- n-propyl second
Acid amides.
2. the method that pipelineization according to claim 1 continuously produces N- n-propyl acetamides, it is characterized in that：
Acetate esters are ethyl acetate, methyl acetate or propyl acetate；
Corresponding product is ethanol, methanol, normal propyl alcohol.
3. the method that pipelineization according to claim 2 continuously produces N- n-propyl acetamides, it is characterized in that：
React coil pipe (4) total measurement (volume) be 251mL, step 3) in acetate esters and n-propylamine mixed solution enter reaction coil pipe
(4) flow when is 0.40~2.10mL/min.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110091609A (en) * | 2018-01-29 | 2019-08-06 | 纪州技研工业株式会社 | Ink-jet printer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120277444A1 (en) * | 2011-04-27 | 2012-11-01 | Shivkumar Mahadevan | Synthesis of hydroxyalkyl amides from esters |
| CN105330559A (en) * | 2015-10-14 | 2016-02-17 | 宿迁新亚科技有限公司 | Electronic-grade formamide compound preparation method |
| CN205035303U (en) * | 2015-10-12 | 2016-02-17 | 宿迁新亚科技有限公司 | Consecutive reaction device of N - methyl carboxamide |
-
2017
- 2017-05-26 CN CN201710384232.5A patent/CN107118118B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120277444A1 (en) * | 2011-04-27 | 2012-11-01 | Shivkumar Mahadevan | Synthesis of hydroxyalkyl amides from esters |
| CN205035303U (en) * | 2015-10-12 | 2016-02-17 | 宿迁新亚科技有限公司 | Consecutive reaction device of N - methyl carboxamide |
| CN105330559A (en) * | 2015-10-14 | 2016-02-17 | 宿迁新亚科技有限公司 | Electronic-grade formamide compound preparation method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110091609A (en) * | 2018-01-29 | 2019-08-06 | 纪州技研工业株式会社 | Ink-jet printer |
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