CN106117137A - A kind of method utilizing micro-reaction device to prepare anti-aging agent RD monomer continuously - Google Patents
A kind of method utilizing micro-reaction device to prepare anti-aging agent RD monomer continuously Download PDFInfo
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- CN106117137A CN106117137A CN201610495393.7A CN201610495393A CN106117137A CN 106117137 A CN106117137 A CN 106117137A CN 201610495393 A CN201610495393 A CN 201610495393A CN 106117137 A CN106117137 A CN 106117137A
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- micro
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- acetone
- aniline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a kind of method preparing anti-aging agent RD monomer in micro passage reaction continuously, it is under catalyst action, aniline and acetone prepare anti-aging agent RD monomer in micro passage reaction.Compared with prior art, the course of reaction of the present invention need not add toluene, and reduce the consumption of acetone in reaction, effectively saved raw material.The inventive method has the advantages such as simple flow, reaction-ure conversion-age height and target product selectivity are good.Meanwhile, the inventive method cost is relatively low, and environmental pollution is little, and can serialization uninterruptedly produce, and has good prospects for commercial application.
Description
Technical field
The invention belongs to chemical industry synthesis field, be specifically related to one and utilize micro-reaction device to prepare anti-aging agent RD monomer continuously
Method.
Background technology
Rubber antiager RD monomer (2,2,4-trimethyl-1,2-dihyaroquinoline) is that a kind of important organic chemical industry is former
Material, its polymer is the rubber antioxidants that a kind of performance is remarkable.As a kind of ketone amines antioxidants, it is old that hot oxygen is caused by RD
Changing and have splendid protective benefits, metal is catalyzed oxidation simultaneously also extremely strong inhibitory action.Processability to rubber simultaneously
Can, the physical property of vulcanization characteristics and vulcanizate does not affect, and is widely used in neoprene, butadiene-styrene rubber, cis-butadiene cement, isoamyl glue etc.
In the various products of synthetic rubber and natural rubber.Anti-aging agent RD function admirable, and low toxicity, without carcinogen, have huge
Big market demand.
United States Patent (USP) US4515570 be relatively early disclose with aniline with acetone as raw material, use large porous strong acid sulfonic acid type ion
Exchanger resin makees catalyst and prepares the technical literature of RD monomer.But this kind of catalyst effective acid content is low, poor heat resistance, instead
Between Ying Shi longer, and catalyst is not easily recycled, and is not easy to commercial production.
At present, commercial production anti-aging agent RD has one-step method and two kinds of approach of two-step method.One-step method is exactly aniline and acetone
Condensation polymerization is carried out in same reactor, directly obtains the polymer of RD.Two-step method is then that aniline and acetone are first in catalysis
It is condensed under agent effect, forms RD monomer, then by RD monomer fractional distillation, add acid catalyzed polymerisation.
When using two-step method to produce, during the polymerization of RD monomer, do not contact the raw material such as aniline, acetone, so its side reaction is few, produce
Quality is good.Japan Patent JP55040661 describes condensation reaction technique: aniline, p-methyl benzenesulfonic acid are added reactor and added
Heat, added acetone in 8 hours at 95～100 DEG C, steams the water that the dehydration containing unreacted acetone generates, reactant
By dilution with toluene, keeping 85～95 DEG C, neutralize with sodium hydroxide solution, branch vibration layer after standing, oil reservoir washes with water several times, extremely
Solution is neutrality, divides and takes toluene layer, toluene is distilled off, then rectification under vacuum obtains RD monomeric fraction, gained RD monomeric fraction warp
Chromatography, containing 2,2,4-trimethyl-1,2-dihyaroquinoline is 97%.
One-step method is simple relative to two-step method reaction process, but side reaction is many, and post processing is more complicated, and domestic industry produces
The isopropyl diphenyl amine that the reaction that in middle one-step method products therefrom, active component dimer content is relatively low and adjoint generates
(IBA) content is higher, due to the strong carcinogen of IBA, causes the of low quality of product.
In sum, the technique utilizing prior art synthesis anti-aging agent RD, there is effective product content low, product quality
Difference, produces and consumes big, that production garbage is many defect.Although two-step method is relative to one-step method complex operation, but the product prepared is pure
Degree height, steady quality, it is possible to meet the high-quality requirement in rubber industry.Therefore, a kind of simple to operate, low cost, product are found
Quality is high, the monomer production new technique of environmental protection has very important significance.
Summary of the invention
The technical problem to be solved in the present invention is to provide and a kind of utilizes micro-reaction device to prepare anti-aging agent RD monomer continuously
Method, to solve the poor product quality that prior art exists, produce consume big, garbage is many and the problem such as complex operation.
For solving above-mentioned technical problem, the technical solution used in the present invention is as follows:
A kind of method utilizing micro-reaction device to prepare anti-aging agent RD monomer continuously, it comprises the steps:
Under conditions of lucifuge, acetone, aniline and catalyst pump are entered in the micro-mixer in micro-reaction device, the most mixed
Pump into after conjunction in the microreactor in micro-reaction device and react；After having reacted, gained reactant liquor is through Distillation recovery acetone
After, residual reaction liquid is adjusted pH value to neutral, decompression distillation obtains anti-aging agent RD monomer.
Wherein, the mol ratio of aniline and acetone is 1:2～6.
Wherein, the mol ratio of aniline and catalyst is 1:0.05～1.
Wherein, described catalyst is hydrochloric acid, anilinechloride, p-methyl benzenesulfonic acid, trifluoroacetic acid, formic acid, acetic acid and three
Any one or a few combination in boron fluoride；Wherein, catalyst is preferably hydrochloric acid, anilinechloride, trifluoroacetic acid or three
Boron fluoride.
Wherein,
When catalyst is anilinechloride, catalyst is dissolved in aniline, then with acetone by material inlet pump respectively
Enter in micro-reaction device；
When catalyst is hydrochloric acid, catalyst is dissolved in aniline, the moisture being distilled off in hydrochloric acid, then passes through with acetone
Material inlet pumps in micro-reaction device respectively；
When selecting other catalyst in addition to anilinechloride and hydrochloric acid, catalyst is dissolved in acetone, then and benzene
Amine is pumped in micro-reaction device respectively by material inlet；
When selecting the combination of anilinechloride and other catalyst, anilinechloride is dissolved in aniline, other is urged
Agent is dissolved in acetone, then is pumped into respectively in micro-reaction device by material inlet.
Wherein, in microreactor, reaction temperature is 100～160 DEG C, preferably 130～150 DEG C；The time of staying be 1～
120min, preferably 1～60min.
Wherein,
Vapo(u)rizing temperature when reclaiming acetone is 80～120 DEG C.
Regulation pH agents useful for same is sodium hydroxide, sodium carbonate or sodium phosphate.
The temperature of decompression distillation is 160～220 DEG C.
Wherein, described micro-reaction device includes micro-mixer and the microreactor being connected by connecting tube；Wherein, micro-mixed
The charging aperture of clutch is connected by connecting tube 1～3 material inlet, and the discharging opening of micro-mixer connects counterbalance valve.
Wherein, described micro-mixer is Y type, T-shaped or J-type blender, and described microreactor is tubular microreactors,
Internal diameter is 0.5～5.0mm, a length of 0.5～40m.
Wherein, described flow velocity is blended device mixed mixed liquor flow velocity, and flow velocity is 0.04～10mL/min.
The flow velocity of micro-mixer discharging is 0.04～5mL/min.
Wherein, preferred reaction conditions is as follows:
Catalyst be anilinechloride, reaction temperature be 140 DEG C, the time of staying is 10min, and flow velocity is 1mL/min, micro-instead
Answering device internal diameter is 1mm；
Wherein, the reaction equation of the present invention is as follows:
Beneficial effect:
Compared with prior art, the present invention has the advantage that
The raw material acetone amount that the present invention reacts required is few, and reaction-ure conversion-age is higher, and by-product is few, and the selectivity of reaction is relatively
Height, product quality is outstanding.Loss to equipment is low simultaneously, can the most continual produce.Meanwhile, the method for the present invention
Simple to operate, environmental pollution is little, has good prospects for commercial application.
Accompanying drawing explanation
Fig. 1 is preparation technology schematic diagram of the present invention.
Detailed description of the invention
According to following embodiment, the present invention be may be better understood.But, as it will be easily appreciated by one skilled in the art that reality
Execute the content described by example and be merely to illustrate the present invention, and should be also without limitation on basis described in detail in claims
Invention.
Embodiment 1
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 2mL/min.Reactant liquor time of staying in reactor is 5min.
Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 2
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 1mL/min.Reactant liquor time of staying in reactor is 10min.
Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 3
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 0.334mL/min.Reactant liquor time of staying in reactor is
30min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 4
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 0.167mL/min.Reactant liquor time of staying in reactor is
60min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 5
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 0.1mL/min.Reactant liquor time of staying in reactor is
100min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 6
Take 2.81g hydrochloric acid to be dissolved in 26.89g acetone, then take 14.34g aniline.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 1mL/min.Reactant liquor time of staying in reactor is 10min.
Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 7
Take 10.26g trifluoroacetic acid to be dissolved in 31.36g acetone, then take 16.76g aniline.With syringe pump, two phase liquid is led to
Crossing T-shaped blender, be passed through in the reactor that caliber is 1mm, flow velocity is 2mL/min.Reactant liquor time of staying in reactor is
5min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 8
Take 10.26g trifluoroacetic acid to be dissolved in 31.36g acetone, then take 16.76g aniline.With syringe pump, two phase liquid is led to
Crossing T-shaped blender, be passed through in the reactor that caliber is 1mm, flow velocity is 1mL/min.Reactant liquor time of staying in reactor is
10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 9
Take 10.26g trifluoroacetic acid to be dissolved in 31.36g acetone, then take 16.76g aniline.With syringe pump, two phase liquid is led to
Crossing T-shaped blender, be passed through in the reactor that caliber is 1mm, flow velocity is 0.334mL/min.When reactant liquor stops in reactor
Between be 30min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 10
Take 7.18g trifluoroacetic acid to be dissolved in 31.36g acetone, then take 16.76g aniline.With syringe pump, two phase liquid is passed through
T-shaped blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 1mL/min.Reactant liquor time of staying in reactor is
10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 11
The formic acid taking 1.26g is dissolved in 9.53g acetone, then takes the aniline of 5.09g.With syringe pump, two phase liquid is passed through T
Type blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 2mL/min.Reactant liquor time of staying in reactor is
5min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 12
The formic acid taking 1.26g is dissolved in 9.53g acetone, then takes the aniline of 5.09g.With syringe pump, two phase liquid is passed through T
Type blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 1mL/min.Reactant liquor time of staying in reactor is
10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 13
The acetic acid taking 1.64g is dissolved in 9.53g acetone, then takes the aniline of 5.09g.With syringe pump, two phase liquid is passed through T
Type blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 1mL/min.Reactant liquor time of staying in reactor is
10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 14
The boron trifluoride (boron trifluoride ether solution) taking 0.64g is dissolved in 15.68g acetone, then takes the benzene of 8.38g
Amine.With syringe pump by two phase liquid by T-shaped blender, being passed through in the reactor that caliber is 1mm, flow velocity is 1mL/min.Reaction
Liquid time of staying in reactor is 10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 15
The boron trifluoride (boron trifluoride ether solution) taking 1.28g is dissolved in 15.68g acetone, then takes the benzene of 8.38g
Amine.With syringe pump by two phase liquid by T-shaped blender, being passed through in the reactor that caliber is 1mm, flow velocity is 1mL/min.Reaction
Liquid time of staying in reactor is 10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 16
Take 2.05g trifluoroacetic acid and be dissolved in 15.68g acetone, then taking 2.33g anilinechloride and be dissolved in 6.71g aniline
In.With syringe pump by two phase liquid by T-shaped blender, being passed through in the reactor that caliber is 1mm, flow velocity is 1mL/min.Reaction
Liquid time of staying in reactor is 10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 17
Take 3.07g trifluoroacetic acid and be dissolved in 15.68g acetone, then taking 3.50g anilinechloride and be dissolved in 5.87g aniline
In.With syringe pump by two phase liquid by T-shaped blender, being passed through in the reactor that caliber is 1mm, flow velocity is 1mL/min.Reaction
Liquid time of staying in reactor is 10min.Temperature is 140 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 18
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 1mL/min.Reactant liquor time of staying in reactor is 10min.
Temperature is 130 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
Embodiment 19
Take 10g anilinechloride to be dissolved in 7.17g aniline, take 26.89g acetone.With syringe pump by two phase liquid by T-shaped
Blender, is passed through in the reactor that caliber is 1mm, and flow velocity is 2mL/min.Reactant liquor time of staying in reactor is 10min.
Temperature is 150 DEG C.Reaction carries out a cycle and is followed by extracting reaction solution.
By the reaction result of embodiment 1～19 to illustrate evaluation, the results are shown in Table 1.
Table 1
Claims (8)
1. one kind utilizes the method that micro-reaction device prepares anti-aging agent RD monomer continuously, it is characterised in that it comprises the steps:
Acetone, aniline and catalyst pump are entered in the micro-mixer in micro-reaction device, after being sufficiently mixed, pump into micro-reaction device
In microreactor in react；After having reacted, residual reaction liquid, after Distillation recovery acetone, is adjusted pH by gained reactant liquor
Value is to neutral, and decompression distillation obtains anti-aging agent RD monomer.
Preparation method the most according to claim 1, it is characterised in that the mol ratio of aniline and acetone is 1:2～6.
Preparation method the most according to claim 1, it is characterised in that the mol ratio of aniline and catalyst is 1:0.05～1.
Preparation method the most according to claim 1, it is characterised in that described catalyst is hydrochloric acid, anilinechloride, right
Any one or a few combination in toluenesulfonic acid, trifluoroacetic acid, formic acid, acetic acid and boron trifluoride.
Preparation method the most according to claim 1, it is characterised in that in microreactor, reaction temperature is 100～160 DEG C,
The time of staying is 1～120min.
Preparation method the most according to claim 1, it is characterised in that described micro-reaction device includes by connecting tube phase
Micro-mixer even and microreactor；Wherein, the charging aperture of micro-mixer is connected by connecting tube 1～3 material inlet.
Preparation method the most according to claim 1, it is characterised in that described microreactor is tubular microreactors, interior
Footpath is 0.5～5.0mm, a length of 0.5～40m.
Obtain preparation method the most according to claim 1, it is characterised in that the flow velocity of micro-mixer discharging is 0.04～5mL/
min。
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106831515A (en) * | 2017-01-13 | 2017-06-13 | 山东斯递尔化工科技有限公司 | The method that tetra-benzyl thiram disulfide is continuously prepared using micro-reaction device |
| CN106831564A (en) * | 2016-12-21 | 2017-06-13 | 山东斯递尔化工科技有限公司 | A kind of method that utilization micro-reaction device continuously prepares antioxidant 224 |
| CN106995396A (en) * | 2017-03-30 | 2017-08-01 | 山东斯递尔化工科技有限公司 | A kind of method that utilization micro-reaction device continuously prepares SDD |
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Cited By (3)
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| CN106831564A (en) * | 2016-12-21 | 2017-06-13 | 山东斯递尔化工科技有限公司 | A kind of method that utilization micro-reaction device continuously prepares antioxidant 224 |
| CN106831515A (en) * | 2017-01-13 | 2017-06-13 | 山东斯递尔化工科技有限公司 | The method that tetra-benzyl thiram disulfide is continuously prepared using micro-reaction device |
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Inventor after: Guo Kai Inventor after: Wan Li Inventor after: Wang Jincai Inventor after: Fan Bingbing Inventor after: Zhao Xinyuan Inventor after: Ouyang Pingkai Inventor before: Guo Kai Inventor before: Wan Li Inventor before: Fan Bingbing Inventor before: Ouyang Pingkai |
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Effective date of registration: 20170601 Address after: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Applicant after: Nanjing University of Technology Applicant after: SHANDONG STAIR CHEMICAL&TECHNOLOGY CO., LTD. Address before: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Applicant before: Nanjing University of Technology |
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Application publication date: 20161116 |