CN109438341A - Anti-aging agent TMQ and preparation method thereof - Google Patents
Anti-aging agent TMQ and preparation method thereof Download PDFInfo
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- CN109438341A CN109438341A CN201811245995.2A CN201811245995A CN109438341A CN 109438341 A CN109438341 A CN 109438341A CN 201811245995 A CN201811245995 A CN 201811245995A CN 109438341 A CN109438341 A CN 109438341A
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
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Abstract
The invention belongs to rubber chemicals field, it is specifically related to a kind of anti-aging agent TMQ and preparation method thereof.Preparation method includes the following steps: using aniline, acetone as raw material, in the presence of a solvent, prepares anti-aging agent TMQ under the effect of the catalyst, the catalyst is highly acid molecular sieve H-MCM-22, and silica alumina ratio controls between 10-100.Compared with prior art, using highly acid molecular sieve H-MCM-22 catalyst preparation rubber antioxidant TMQ, there is simple production process, reaction time is short, and the three wastes generate few, raw material conversion per pass height, the advantages that effective body content of product is high is a kind of new technology of more industrialization value.
Description
Technical field
The invention belongs to rubber chemicals field, it is specifically related to a kind of anti-aging agent TMQ and preparation method thereof.
Background technique
Rubber antioxidant TMQ is a kind of ketone amines antioxidants, highly effective to the protection of thermo-oxidative ageing, the catalysis to metal
Oxidation also has extremely strong inhibiting effect, and small toxicity is widely used in neoprene, butadiene-styrene rubber, butadiene rubber, isoprene rubber etc.
In the various products of synthetic rubber and natural rubber.Due to its light yellow in color, it may also be used in sanitary rubber product.
Anti-aging agent TMQ is suitable for almost all types of elastomers under various applicable cases, temperature applicable range
Extensively.- the duration in rubber makes rubber size have long-term resistant to thermal aging effect.- sizing material can be prevented to be urged by heavy metal
It is high to change oxidation-molecular weight, is migrated slowly in sizing material matrix, is not easy bloom.
Anti-aging agent TMQ, using acid as catalyst, at 130-140 DEG C of temperature, is condensed and is gathered using aniline and acetone as raw material
Close reaction synthesis.One-step method and two-step method can be divided by technology mode.Two-step method is to be condensed that monomer is made first, is recycled remaining anti-
After answering object, then monomer polymerization is carried out in acid condition；And one-step method is to be completed at the same time monomer preparation and polymerization reaction, then
The remaining reactant of recycling.Two-step process process is long, and consumption is big, but the substance content in products obtained therefrom is high；An and step
Method process is simple, and consumption is small, but substance content is low.
The acid catalyst of anti-aging agent TMQ can be divided into bronsted acid catalyst and lewis acid catalyst two major classes, and in list
The different phase of body condensation and polymerization needs to select different catalyst to reach ideal reaction effect.As RD is traditional
Production method often uses hydrochloric acid as liquid catalyst, but needs to consume hydrochloric acid using sodium hydroxide in post-processing, can not
It is recycled.In addition, as the hydrochloric that is commonly used of RD preparation there are aniline conversions low, poor product quality,
Three-waste pollution is serious, the disadvantage of the high requirements on the equipment, production cycle length.
Also document and patent report are able to maintain the high conversion of aniline using strong-acid ion exchange resin.It is this
The use of catalyst is conducive to the separation of catalyst and the raising of yield, and meets the requirement of environmental protection.But this highly acid sun
The content of ion exchange resin effective acid is low, and heat resistance is poor, and the reaction time is very long, and longest was set up to 25 hours or more
The easily broken inconvenient recycling of rouge, loss is big, is unfavorable for industrialized production.
Japan Patent JP55-40661, which is disclosed, a kind of uses p-methyl benzenesulfonic acid for the aniline of catalyst and condensation of acetone
The method that technique produces anti-aging agent TMQ, although reactivity is relatively good, catalyst amount is big and is not easily recycled, production process
Present in high temperature link catalyst can also decomposed generate sulfur dioxide gas, and reaction yield is low, high production cost, monomer
Production is not easy to control, and product composition is complicated, and environmental pollution is serious, is unfavorable for industrialized production.
The anti-aging agent TMQ of above-mentioned technology synthesis, secondly polymer content is low, product prevents that old effect is poor, produces serious three wastes,
It is at high cost, non-green chemical industry skill.
Summary of the invention
The purpose of the present invention is to overcome the defects in the prior art, provides a kind of anti-aging agent TMQ and preparation method thereof.
The present invention to achieve the above object, using following technical scheme:
A kind of preparation method of anti-aging agent TMQ, which is characterized in that using aniline, acetone as raw material, solvent there are the case where
Under, anti-aging agent TMQ is prepared under the effect of the catalyst, and the catalyst is highly acid molecular sieve；Highly acid molecular sieve is H-
MCM-22, the silica alumina ratio of the highly acid molecular sieve H-MCM-22 is between 10-100.Preferably, the highly acid molecular sieve H-
The silica alumina ratio of MCM-22 is between 30-60.
Wherein, the solvent is one of benzene,toluene,xylene, hexamethylene, trimethylbenzene.
For the mass ratio that feeds intake of the aniline and acetone for 1:1-10, the mass ratio that feeds intake of aniline and solvent is 1:1-10,
100-200 DEG C of reaction temperature, reaction pressure 0.1-3Mpa, the charging gross mass air speed of raw material is 0.1h-1-26h-1。
Preferably, it is 1:2-5 reaction that the mass ratio that feeds intake of aniline and acetone, which is the mass ratio that feeds intake of 1:2-5 aniline and solvent,
Temperature is 130-150 DEG C, reaction pressure 0.5-1.5Mpa, and the charging gross mass air speed of raw material is 0.7h-1-14h-1。
Reaction, which feeds intake, to be fed intake using fair current or is countercurrently fed intake；Reaction is using fair current when being fed intake, in advance by aniline, acetone and molten
Agent disposably feeds intake after mixing according to ingredient proportion；When reaction is fed intake using adverse current, in advance by aniline and solvent according to throwing
Material ratio is put into reactor using reflux type after mixing, with acetone steam.
Using continuous production technology.
Treatment process is that the product of autoreactor outflow first passes through the water that liquid separation separation generates, and upper layer solvent is mutually through depressurizing
After being distilled to recover solvent and surplus stock and unconverted monomer, finished product TMQ can be obtained.
Vacuum distillation recovered solvent and surplus stock, vacuum degree control control gas phase temperature in 80-180 in -0.09Mpa
℃。
Vacuum distillation recycling unconverted monomer, control vacuum degree are less than -0.098Mpa, distill 240-280 DEG C of gas phase temperature.
The invention also includes a kind of anti-aging agent TMQ, are obtained by the preparation method.
Compared with prior art, the beneficial effects of the present invention are: applying the technical scheme of the present invention, it is with aniline and acetone
Raw material under solid acid catalysis, prepares rubber antioxidant TMQ in the presence of solvent, aniline conversion per pass up to 90-95%,
Effective body (two, three, the tetramer) content is up to 85-90% in product RD, wherein dimer content 60-70%.
Technology involved in this patent, because, as catalyst, comparing, urging compared with liquid hydrochloric acid catalysis using highly acid molecular sieve
Agent is recyclable, reusable, simultaneously because not having alkali neutralization step, almost without waste water generation, technique is more environmentally protective；
Meanwhile molecular sieve catalyst is non-breakable, the service life is longer for strong acidity cation exchange resin, it is easier to carry out production and turn
Change, solves easily broken in Ion exchange resins solid acid catalyst production process, the not high problem of service life.
Technology involved by this patent is taking full advantage of molecular sieve highly acid using highly acid molecular sieve as catalyst
While with reusable property, by the design feature of molecular sieve itself, by its channel diameter to TMQ monomer polymerization process
It is screened.Catalyst carrier H-MCM-22 molecular sieve pore passage structure is mainly distributed on 0.4-1.82nm, allows in catalytic process
Raw material, TMQ monomer and dimer pass through, and without allowing tripolymer and the above product to pass through, consider from molecular diameter angle, this is specially
Catalyst involved in benefit can effectively control TMQ monomer polymerization degree, because product more than dimer can not be in catalyst
Generate and deviate from duct, so can be effectively controlled the product degree of polymerization using catalyst TMQ polymerization, prevent dimer into
One step and monomer are polymerize, to control the generation of the three, tetramer in product, and then improve product quality.
In conclusion compared with prior art, it is anti-old using highly acid molecular sieve H-MCM-22 catalyst preparation rubber
Agent TMQ has simple production process, and the reaction time is short, and the three wastes generate few, raw material conversion per pass height, the effective body content of product
The advantages that high is a kind of new technology of more industrialization value.
Specific embodiment
In order to make those skilled in the art more fully understand technical solution of the present invention, implement below with reference to best
The present invention is described in further detail for example.
Embodiment 1
A kind of synthetic method of new anti-aging agent TMQ.This method includes depositing using aniline, acetone as raw material in solvent toluene
In case, anti-aging agent TMQ is prepared under the effect of the catalyst, and catalyst is H-MCM-22 type molecular sieve, molecular sieve sial
Than being 60.Reaction is fed intake using fair current, is in advance mixed aniline, acetone and solvent toluene according to the ratio of feed ratio 1:3:3 equal
After even, control feedstock quality air speed is 5h-1Carry out continuous dosing；Controlling the temperature in reaction process is 135-140 DEG C, reaction pressure
Power is 1.0Mpa.
The product of autoreactor outflow first passes through the water that liquid separation separation generates, and upper layer solvent returns respectively mutually through being evaporated under reduced pressure
After receiving solvent and surplus stock and unconverted monomer, finished product TMQ can be obtained；Vacuum distillation recovered solvent and surplus stock, very
Reciprocal of duty cycle control controls gas phase temperature at 80-180 DEG C in -0.09Mpa.Vacuum distillation recycling unconverted monomer, control vacuum degree are small
In -0.098Mpa, 240-280 DEG C of gas phase temperature is distilled.(similarly hereinafter)
Through detecting, aniline conversion per pass is 90.5% in the present embodiment, effective body (two, three, the tetramer) in product TMQ
Content is up to 88.6%, wherein dimer content 62.3%.
Embodiment 2:
A kind of synthetic method of new anti-aging agent TMQ.This method includes using aniline, acetone as raw material, in solvent xylene
In the presence of, anti-aging agent TMQ is prepared under the effect of the catalyst, and catalyst is H-MCM-22 type molecular sieve, molecular sieve silicon
Aluminium ratio is 100.Reaction is fed intake using fair current, is in advance mixed aniline, acetone and dimethylbenzene according to the ratio of feed ratio 1:3:3 equal
After even, control feedstock quality air speed is 5h-1Carry out continuous dosing；Controlling the temperature in reaction process is 130-135 DEG C, reaction pressure
Power is 0.5Mpa；
Through detecting, aniline conversion per pass is 75.8% in the present embodiment, effective body (two, three, the tetramer) in product TMQ
Content is up to 57.1%, and wherein dimer contains 45.8%.
A kind of embodiment 3: synthetic method of new anti-aging agent TMQ.This method includes using aniline, acetone as raw material, molten
In the presence of agent trimethylbenzene, anti-aging agent TMQ is prepared under the effect of the catalyst, catalyst is H-MCM-22 type molecular sieve,
Molecular sieve silica alumina ratio is 10.Reaction is fed intake using fair current, in advance by aniline, acetone and solvent toluene according to feed ratio 1:3:3's
After mixing, control feedstock quality air speed is 0.7h to ratio-1Carry out continuous dosing；Controlling the temperature in reaction process is 145-
150 DEG C, reaction pressure 1.0Mpa；
Through detecting, aniline conversion per pass is 89.9% in the present embodiment, effective body (two, three, the tetramer) in product TMQ
Content is up to 41.1%, wherein dimer content 27.6%.
A kind of embodiment 4: synthetic method of new anti-aging agent TMQ.This method includes using aniline, acetone as raw material, molten
In the presence of agent toluene, anti-aging agent TMQ is prepared under the effect of the catalyst, catalyst is H-MCM-22 type molecular sieve, point
Son sieve silica alumina ratio is 60.Reaction is fed intake using adverse current, in advance mixes aniline, solvent toluene according to the ratio of feed ratio 1:2:2
After uniformly, inversely and in acetone steam (being 1:3 with aniline mass ratio) investment reactor.Control feedstock quality air speed is 14h-1
Carry out continuous dosing；Controlling the temperature in reaction process is 135 DEG C, reaction pressure 0.5Mpa；
Through detecting, aniline conversion per pass is 93.1% in the present embodiment, effective body (two, three, the tetramer) in product TMQ
Content is up to 86.4%, wherein dimer content 66.8%.
A kind of embodiment 5: synthetic method of new anti-aging agent TMQ.This method includes using aniline, acetone as raw material, molten
In the presence of agent toluene, anti-aging agent TMQ is prepared under the effect of the catalyst, catalyst is H-MCM-22 type molecular sieve, point
Son sieve silica alumina ratio is 40.Reaction is fed intake using fair current, in advance by aniline, acetone and solvent toluene according to the ratio of feed ratio 1:5:5
After mixing, control feedstock quality air speed is 0.1h to example-1Carry out continuous dosing；Controlling the temperature in reaction process is 100 DEG C,
Reaction pressure is 0.1Mpa；Through detecting, aniline conversion per pass is 84.8% in the present embodiment, in product TMQ effectively body (two,
Three, the tetramer) content is up to 45.2%, wherein dimer content 29.7%.
A kind of embodiment 6: synthetic method of new anti-aging agent TMQ.This method includes using aniline, acetone as raw material, molten
In the presence of agent toluene, anti-aging agent TMQ is prepared under the effect of the catalyst, catalyst is H-MCM-22 type molecular sieve, point
Son sieve silica alumina ratio is 30.Reaction is fed intake using fair current, in advance by aniline, acetone and solvent toluene according to feed ratio 1:10:10's
After mixing, control feedstock quality air speed is 26h to ratio-1Carry out continuous dosing；Controlling the temperature in reaction process is 200
DEG C, reaction pressure 3.0Mpa；Through detecting, aniline conversion per pass is 68.5% in the present embodiment, effective body in product TMQ
(two, three, the tetramer) content is up to 40.8%, wherein dimer content 22.5%.
The above is only a preferred embodiment of the present invention, for those of ordinary skill in the art, according to the present invention
Thought, there will be changes in the specific implementation manner and application range, and the content of the present specification should not be construed as to the present invention
Limitation.
Claims (10)
1. a kind of preparation method of anti-aging agent TMQ, which is characterized in that using aniline, acetone as raw material, solvent there are the case where
Under, anti-aging agent TMQ is prepared under the effect of the catalyst, and the catalyst is highly acid molecular sieve H-MCM-22, silica alumina ratio
Control is between 10-100.
2. the preparation method of anti-aging agent TMQ according to claim 1, which is characterized in that the solvent be benzene, toluene,
One of dimethylbenzene, hexamethylene, trimethylbenzene.
3. the preparation method of anti-aging agent TMQ according to claim 1, which is characterized in that the throwing of the aniline and acetone
Material mass ratio is 1:1-10, and the mass ratio that feeds intake of aniline and solvent is 1:1-10, and 100-200 DEG C of reaction temperature, reaction pressure is
0.1-3Mpa, the charging gross mass air speed of raw material are 0.1h-1-26h-1.
4. the preparation method of anti-aging agent TMQ according to claim 1, which is characterized in that the quality that feeds intake of aniline and acetone
Than for 1:2-5, the mass ratio that feeds intake of aniline and solvent is 1:2-5, reaction temperature is 130-150 DEG C, reaction pressure 0.5-
1.5Mpa, the charging gross mass air speed of raw material are 0.7h-1-14h-1.
5. the preparation method of anti-aging agent TMQ according to claim 1, which is characterized in that reaction feeds intake to be fed intake using fair current
Or adverse current feeds intake；It is in advance that aniline, acetone and solvent is primary after mixing according to ingredient proportion when reaction is fed intake using fair current
Property feeds intake；Reaction using adverse current feed intake when, in advance by aniline and solvent according to ingredient proportion after mixing, adopted with acetone steam
With in reflux type investment reactor.
6. the preparation method of anti-aging agent TMQ according to claim 1, which is characterized in that use continuous production technology.
7. the preparation method of anti-aging agent TMQ according to claim 1, which is characterized in that last handling process is autoreactor
The product of outflow first passes through the water that liquid separation separation generates, and upper layer solvent does not gather through vacuum distillation recovered solvent and surplus stock and mutually
After closing monomer, finished product TMQ can be obtained.
8. the preparation method of anti-aging agent TMQ according to claim 7, which is characterized in that vacuum distillation recovered solvent and surplus
Remaining raw material, vacuum degree control control gas phase temperature at 80-180 DEG C in -0.09Mpa.
9. the preparation method of anti-aging agent TMQ according to claim 7, which is characterized in that unpolymerized list is recycled in vacuum distillation
Body, control vacuum degree are less than -0.098Mpa, distill 240-280 DEG C of gas phase temperature.
10. a kind of anti-aging agent TMQ, which is characterized in that obtained using the described in any item preparation methods of claim 1-9.
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Cited By (3)
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| CN112657488A (en) * | 2019-10-15 | 2021-04-16 | 中石化南京化工研究院有限公司 | Polyacid type solid catalyst |
| CN113402457A (en) * | 2021-07-13 | 2021-09-17 | 宁波海利化工有限公司 | Preparation method of efficient antioxidant RD |
| CN114149366A (en) * | 2021-10-26 | 2022-03-08 | 中国石油化工股份有限公司 | Preparation method of rubber antioxidant TMQ |
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