CN110283091A - The synthetic method of amides defoaming agent - Google Patents
The synthetic method of amides defoaming agent Download PDFInfo
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- CN110283091A CN110283091A CN201910728884.5A CN201910728884A CN110283091A CN 110283091 A CN110283091 A CN 110283091A CN 201910728884 A CN201910728884 A CN 201910728884A CN 110283091 A CN110283091 A CN 110283091A
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- octodrine
- defoaming agent
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- amides
- dehydration condensation
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to defoaming agent technical fields, are specifically related to a kind of synthetic method of amides defoaming agent.Using isononanoic acid and octodrine as raw material, under tin catalyst effect, substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.The synthetic method of amides defoaming agent of the present invention, using isononanoic acid and octodrine as raw material, under tin catalyst effect, octodrine is added stage by stage carries out dehydration condensation, conversion ratio is stepped up by dehydration condensation stage by stage, significant loss is reduced, obtained amides defoaming agent purity is high；And distillation fraction is mainly water and octodrine, after separation, octodrine continues to carry out using raising product yield as raw material.
Description
Technical field
The invention belongs to defoaming agent technical fields, are specifically related to a kind of synthetic method of amides defoaming agent.
Background technique
Foam is a kind of dispersion of gas in a liquid, is a kind of system of thermodynamic instability.In many industry
Can all there be foam in production process, as paper pulp papermaking, textile printing and dyeing, coating processing, sewage treatment, biofermentation, petroleum are opened
It adopts and refines, building industry, adhesive etc..Subtract however, the foam in these industrial processes is likely to result in production capacity
The problems such as small, wastage of material, reaction time extend, product quality declines.Therefore, how research suppresses or eliminates unwanted bubbles
Defoaming agent has great economic significance and significance of scientific research.Amides defoaming agent belongs to first generation defoaming agent, such defoaming agent poison
Property it is relatively small, it is good fluidity, easy to use, cheap, but the original that the typical synthetic method of amide compound tradition uses
Material and relevant technique are relatively complicated, and conversion ratio and yield are limited, and obtained product purity is not high.
Summary of the invention
The purpose of the present invention is overcome the deficiencies of the prior art and provide a kind of synthetic method of amides defoaming agent.The conjunction
More simple and safe at method process, significant loss is few, and the defoaming agent of preparation purity is high, defoaming effect is good, be suitable for textile auxiliary,
The fields such as papermaking, petrochemical industry.
The synthetic method of amides defoaming agent of the present invention is catalyzed using isononanoic acid and octodrine as raw material in tin class
Under agent effect, substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.
Wherein:
Room temperature under nitrogen protection state, isononanoic acid and tin catalyst is sequentially added in reactor and stirred evenly, different pungent
Amine is added in two steps, carries out two stages dehydration condensation.
The molar ratio 1:1.1-1.3 of isononanoic acid and octodrine；Tin catalyst accounts for isononanoic acid mole percent
0.1%-0.3%.
Specific step is as follows for two stages dehydration condensation:
(1) first stage: being added the octodrine for accounting for octodrine gross mass 40-60%, is warming up to 110-130 DEG C, reacts 1-3
Hour, carry out first stage dehydration condensation；
(2) second stage: being added remaining octodrine, is warming up to 130-150 DEG C, reacts 4-8 hours, carries out second stage
Dehydration condensation.
The vacuum degree of first stage dehydration condensation is 600-800mbar.
The vacuum degree of second stage dehydration condensation is 400-600mbar.
Vacuum distillation is specifically, and after second stage dehydration condensation, will react temperature with the heating rate of 10 DEG C/h
Degree is warming up to 150-170 DEG C, in 2 hours, slowly adjusts vacuum degree to 0mbar, carries out vacuum distillation 4-8 hours.
The slowly adjustment vacuum degree is specifically: being adjusted to absolute pressure from the 400-600mbar of second stage dehydration
0mbar can not be lowered during the adjustment with certain rate, when pressure is from 600mabr to 400mabr, regardless of with which kind of
Rate is lowered, and material is all not in that situation is splashed in boiling, but when pressure is from 400mabr to 0mabr, pressure will be gradually decreased,
During downward, the rate of pressure reduction is gradually decreased, and closer to 0mabr, speed change rate is lower under pressure, and pressure is gradually lowered
Rate standard be reactant do not occur boiling splash situation.
Tin catalyst is dibutyl tin dilaurate, Bis(lauroyloxy)dioctyltin, stannous octoate or bis-acetylacetonate
One of base dibutyl tin.
As a preferred technical solution, the synthetic method of amides defoaming agent of the present invention, including following step
It is rapid:
(1) under room temperature under nitrogen guard mode, isononanoic acid is added in reactor, it is equal that tin catalyst stirring is then added
It is even；
(2) octodrine for accounting for octodrine gross mass 40-60% is added, is warming up to 110-130 DEG C, reacts 1-3 hours, carries out
First stage dehydration condensation；
(3) remaining octodrine is added, is warming up to 130-150 DEG C, reacts 4-8 hours, carries out second stage dehydrating condensation
Reaction；
(4) after second stage dehydration condensation, reaction temperature is increased to by 150- with the heating rate of 10 DEG C/h
170 DEG C, vacuum degree is slowly adjusted to 0mbar in 2 hours, vacuum distillation 4-8 hours is carried out, obtains high-purity amides
Close object.
The reactive chemistry equation of amides defoaming agent preparation of the present invention is as follows:
This reaction is a reversible reaction, and reversible reaction is needed in reaction process to possess higher conversion ratio
There are a kind of raw material excess or product (such as water) endlessly to be removed system, just can guarantee reaction towards positive and negative in this way
Should carry out.
It is added amine stage by stage, the first stage, excessive acid in system, second stage, amine is excessive in system, the stage each in this way
All ensure that a kind of raw material be it is excessive, be conducive to improve conversion ratio；If disposable be all added amine, it is excessive for just having started amine
, but with the reaction of high-temperature vacuum, amine loss is steamed than comparatively fast, can may finally remain more acid in system
The stage is evaporated, acid is not easy to be distilled out of；The purpose of this patent is to want sour total overall reaction, and excessive amine can be moved in the distillation stage
It removes, and can be used again.
As for the condition of control, temperature and vacuum and reaction time, at the beginning in excessive acid, the enough situations of catalyst
Under, reaction is opposite to be easier positive progress, so temperature and vacuum degree can be with more relatively mild, the time does not need too long；The
Two-stage is the key reaction stage, needs to improve temperature, improves vacuum, it is therefore an objective in the maximum water for removing reaction and generating
While to control amine and cannot excessively lose, while also to guarantee that reaction system raw material acid has been reacted as far as possible, time needs to the greatest extent may be used
It can be long.
And the distillation stage has been arrived, main purpose is purifying, and water, unreacted amine, even acid and catalyst are intended to be steamed
It distillates, so needing higher temperature and vacuum degree, this process certainly can also some material under high temperature high vacuum
It is reacted, unreacted (mainly amine) will be distilled, finally obtain the higher product of purity --- amides compound.
Compared with prior art, the invention has the following advantages:
(1) synthetic method of amides defoaming agent of the present invention, technique and the relatively easy safety of raw material, stage by stage
It is reacted and is evaporated in vacuo, obtained amides defoaming agent purity reaches 97% or more, and defoaming effect is good, is suitable for weaving
The fields such as auxiliary agent, papermaking, petrochemical industry.
(2) synthetic method of amides defoaming agent of the present invention is urged using isononanoic acid and octodrine as raw material in tin class
Under agent effect, octodrine is added stage by stage carries out dehydration condensation, is stepped up and is turned by dehydration condensation stage by stage
Rate reduces significant loss, obtained amides defoaming agent purity is high；And distillation fraction is mainly water and octodrine, after separation,
Octodrine continuation is used as raw material, improves product yield.
Specific embodiment
The invention will be further described with reference to embodiments.
Embodiment 1
A kind of synthetic method of amides defoaming agent, using isononanoic acid and octodrine as raw material, under tin catalyst effect,
Substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.
Isononanoic acid and octodrine are reacted using the molar ratio of 1:1.1, isononanoic acid 30.00g, octodrine 26.96g,
Octodrine is added in two steps by the mass ratio of 1:1 to be reacted；Specifically includes the following steps:
(1) 30.00g isononanoic acid is added in clean 100ml flask, addition accounts for the 0.1% of isononanoic acid mole percent
Catalyst dibutyltin dilaurylate, stirring；
(2) first stage dehydration condensation: being added octodrine 13.48g, be warming up to 110 DEG C, under vacuum 600mbar, instead
It answers 3 hours；
(3) second stage dehydration condensation: being added octodrine 13.48g, be warming up to 130 DEG C, under vacuum 400mbar, instead
It answers 8 hours；
(4) after second stage dehydration condensation, reaction temperature is increased to 170 with the heating rate of 10 DEG C/h
DEG C, vacuum degree is slowly improved in 2 hours to 0mbar, is carried out vacuum distillation 4 hours, is obtained amides compound 49.55g, gas phase
Product effective component 97.02% is detected, yield is 97.29%.
Embodiment 2
A kind of synthetic method of amides defoaming agent, using isononanoic acid and octodrine as raw material, under tin catalyst effect,
Substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.
Isononanoic acid and octodrine are reacted using the molar ratio of 1:1.2, isononanoic acid 30.00g, octodrine 29.40g,
Octodrine is added in two steps by the mass ratio of 2:3 to be reacted；Specifically includes the following steps:
(1) 30.00g isononanoic acid is added in clean 100ml flask, addition accounts for the 0.2% of isononanoic acid mole percent
Catalyst dibutyltin cinnamic acid dioctyltin, stirring；
(2) first stage dehydration condensation: being added octodrine 11.76g, be warming up to 120 DEG C, under vacuum 700mbar, instead
It answers 2 hours；
(3) second stage dehydration condensation: being added octodrine 17.64g, be warming up to 140 DEG C, under vacuum 500mbar, instead
It answers 6 hours；
(4) after second stage dehydration condensation, reaction temperature is increased to 160 with the heating rate of 10 DEG C/h
DEG C, vacuum degree is slowly improved in 2 hours to 0mbar, is carried out vacuum distillation 6 hours, is obtained amides compound 49.82g, gas phase
Product effective component 97.56% is detected, yield is 97.83%.
Embodiment 3
A kind of synthetic method of amides defoaming agent, using isononanoic acid and octodrine as raw material, under tin catalyst effect,
Substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.
Isononanoic acid and octodrine are reacted using the molar ratio of 1:1.3, isononanoic acid 30.00g, octodrine 31.86g,
Octodrine is added in two steps by the mass ratio of 3:2 to be reacted；Specifically includes the following steps:
(1) 30.00g isononanoic acid is added in clean 100ml flask, addition accounts for the 0.3% of isononanoic acid mole percent
Octoate catalyst stannous, stirring；
(2) first stage dehydration condensation: being added octodrine 19.12g, be warming up to 130 DEG C, under vacuum 800mbar, instead
It answers 1 hour；
(3) second stage dehydration condensation: being added octodrine 12.74g, be warming up to 150 DEG C, under vacuum 600mbar, instead
It answers 4 hours；
(4) after second stage dehydration condensation, reaction temperature is increased to 150 with the heating rate of 10 DEG C/h
DEG C, vacuum degree is slowly improved in 2 hours to 0mbar, is carried out vacuum distillation 8 hours, is obtained amides compound 49.39g, gas phase
Product effective component 98.03% is detected, yield is 96.97%.
Embodiment 4
A kind of synthetic method of amides defoaming agent, using isononanoic acid and octodrine as raw material, under tin catalyst effect,
Substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.
Isononanoic acid and octodrine are reacted using the molar ratio of 1:1.2, isononanoic acid 30.00g, octodrine 29.40g,
Octodrine is added in two steps by the mass ratio of 1:1 to be reacted；Specifically includes the following steps:
(1) 30.00g isononanoic acid is added in clean 100ml flask, addition accounts for the 0.2% of isononanoic acid mole percent
Catalyst bis-acetylacetonate base dibutyl tin, stirring；
(2) first stage dehydration condensation: being added octodrine 14.70g, be warming up to 120 DEG C, under vacuum 600mbar, instead
It answers 2 hours；
(3) second stage dehydration condensation: being added octodrine 14.70g, be warming up to 150 DEG C, under vacuum 500mbar, instead
It answers 4 hours；
(4) after second stage dehydration condensation, reaction temperature is increased to 170 with the heating rate of 10 DEG C/h
DEG C, vacuum degree is slowly improved in 2 hours to 0mbar, is carried out vacuum distillation 6 hours, is obtained amides compound 49.59g, gas phase
Product effective component 97.37% is detected, yield is 97.57%.
Using the product of embodiment 1-4 and commercial like product as the application effect contrast test of defoaming agent:
The detection method introduction of air pump method:
(1) 1000ml beaker is taken, 500ml prepare liquid is measured, air pump is bubbled ball and places beaker bottom central part, and is put
The steel ruler for reading height is set, air pump and timing are opened, different time foam height is recorded, evaluates the foam inhibition ability of defoaming agent.
(2) termination of pumping after 5min continues to record different time foam height, evaluates the defoaming capacity of defoaming agent.
Table 1 is experiment surfactant solution, i.e. bubble solution, and the high foam surfactants of selection are secondary alkyl sulfonic acid
Sodium SAS60.
Table 1 compares surfactant solution used in application effect
Table 2 compares solution to be measured used in application effect
The blistering defoaming effect comparison of table 3
As can be seen from Table 3, amides defoaming agent prepared by the present invention, can satisfy textile industry specific adjuvant
Defoaming requires.
Claims (8)
1. a kind of synthetic method of amides defoaming agent, it is characterised in that: using isononanoic acid and octodrine as raw material, be catalyzed in tin class
Under agent effect, substep carries out dehydration condensation, and amides defoaming agent is obtained after vacuum distillation.
2. the synthetic method of amides defoaming agent according to claim 1, it is characterised in that: room temperature, nitrogen protection state
Under, isononanoic acid and tin catalyst are sequentially added in reactor and stirred evenly, octodrine is added in two steps, and it is de- to carry out two stages
Water condensation reaction.
3. the synthetic method of amides defoaming agent according to claim 1, it is characterised in that: isononanoic acid and octodrine rub
You are ratio 1:1.1-1.3；Tin catalyst accounts for the 0.1%-0.3% of isononanoic acid mole percent.
4. the synthetic method of amides defoaming agent according to claim 2, it is characterised in that: two stages dehydration condensation
Specific step is as follows:
(1) first stage: being added the octodrine for accounting for octodrine gross mass 40-60%, is warming up to 110-130 DEG C, reaction 1-3 is small
When, carry out first stage dehydration condensation；
(2) second stage: being added remaining octodrine, is warming up to 130-150 DEG C, reacts 4-8 hours, carries out second stage dehydration
Condensation reaction.
5. the synthetic method of amides defoaming agent according to claim 4, it is characterised in that: first stage dehydrating condensation is anti-
The vacuum degree answered is 600-800mbar；The vacuum degree of second stage dehydration condensation is 400-600mbar.
6. the synthetic method of amides defoaming agent according to claim 4, it is characterised in that: second stage dehydrating condensation is anti-
After answering, reaction temperature is warming up to 150-170 DEG C with the heating rate of 10 DEG C/h, in 2 hours, adjustment vacuum degree is arrived
0mbar carries out vacuum distillation 4-8 hours.
7. the synthetic method of amides defoaming agent according to claim 1, it is characterised in that: tin catalyst is two laurels
One of sour dibutyl tin, Bis(lauroyloxy)dioctyltin, stannous octoate or bis-acetylacetonate base dibutyl tin.
8. the synthetic method of amides defoaming agent according to claim 1, it is characterised in that: the following steps are included:
(1) under room temperature under nitrogen guard mode, isononanoic acid is added in reactor, tin catalyst is then added and stirs evenly；
(2) octodrine for accounting for octodrine gross mass 40-60% is added, is warming up to 110-130 DEG C, reacts 1-3 hours, carries out first
Stage dehydration condensation；
(3) remaining octodrine is added, is warming up to 130-150 DEG C, reacts 4-8 hours, carries out second stage dehydration condensation；
(4) after second stage dehydration condensation, reaction temperature is increased to by 150-170 with the heating rate of 10 DEG C/h
DEG C, vacuum degree is adjusted to 0mbar in 2 hours, vacuum distillation 4-8 hours is carried out, obtains high-purity amides compound.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113651709A (en) * | 2021-07-27 | 2021-11-16 | 佳化化学（茂名）有限公司 | Fatty amide propyl dimethyl tertiary amine and preparation method and application thereof |
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2019
- 2019-08-08 CN CN201910728884.5A patent/CN110283091A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113651709A (en) * | 2021-07-27 | 2021-11-16 | 佳化化学（茂名）有限公司 | Fatty amide propyl dimethyl tertiary amine and preparation method and application thereof |
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Application publication date: 20190927 |