CN105481688B - A kind of butyl methacrylate production technology of high-efficiency environment friendly - Google Patents
A kind of butyl methacrylate production technology of high-efficiency environment friendly Download PDFInfo
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- CN105481688B CN105481688B CN201510855496.5A CN201510855496A CN105481688B CN 105481688 B CN105481688 B CN 105481688B CN 201510855496 A CN201510855496 A CN 201510855496A CN 105481688 B CN105481688 B CN 105481688B
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- kettle
- esterification
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- polymerization inhibitor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Abstract
The invention discloses a kind of production technology of butyl methacrylate, comprise the following steps：(1) by reaction raw materials n-butanol and methyl methacrylate, catalyst, polymerization inhibitor, which are put into esterifying kettle, carries out esterification；(2) esterification products enter esterification column in the form of azeotropic mixture, the overhead of esterification column, are layered after condensed device condensation into phase-splitter, obtain ester phase methyl methacrylate and be back to esterification column, collect methanol；(4) the kettle liquid part in esterification column is returned esterifying kettle through pump and flowed back again, and another part is neutralized, rectifying, obtains the butyl methacrylate that content is 99.0%~99.8%.After the process implementing, because technique is simpler, it can effectively reduce the occurrence probability of side reaction and avoid the difficulty of later stage wastewater treatment, energy saving technology reaches 5 10%, and production capacity can improve 10 20%, economic and environment-friendly, remarkable benefit.
Description
Technical field
The present invention relates to a kind of production technology of the butyl methacrylate of high-efficiency environment friendly.
Background technology
Butyl methacrylate (BMA) is the important methacrylate vinegar class for being only second to methyl methacrylate, is
A kind of important organic chemical industry's intermediate.Mainly for the preparation of various polymer, production acrylic coating, adhesive are widely used in
And paper, the finishing agent of leather and textile, emulsifying agent, glazing agent, deodorant etc..With China's coating, adhesive, spinning
Knit, papermaking, the industry such as plastics develop rapidly, BMA demand will increasingly be increased, especially the use of East China and south China priming paint
Amount will increase by a fairly big margin, according to the insiders, it is expected that the product market demand will be increased in the coming years with 20% speed.
At present, China produces high-purity BMA (≤99.5% needed for high-grade acrylic coating) largely rely on import, China's high-purity
BMA production technology is still needed further exploitation.
BMA synthesis technique can also use alcoholic acid esterification method and ester-interchange method in addition to Acetone cyanohydrin method.For acrylic acid
Requirement of the industries such as coating to BMA purity and acidity, BMA is synthesized advantageously using ester-interchange method.At present, some producers of China
The concentrated sulfuric acid is used to produce BMA for the ester exchange process of catalyst, although this catalyst is cheap and easy to get, because it has corrosivity,
Harsh is required to equipment, equipment and operating condition, and the reaction time is grown, and side reaction is more, and postprocessing working procedures are cumbersome, and the three wastes are tight
Weight.
The content of the invention
The problem of existing for prior art, the present invention provide a kind of continuous production processes of butyl methacrylate.It is logical
The method for crossing ester exchange, traditional catalyst is reduced to equipment, the corrosion of equipment, and side reaction is more, polymer is difficult etc. asks
The problems such as inscribing, while avoiding the generation, processing, discharge of waste water, reduces material cost consumption needed for production, so as to reach energy-conservation
Put forward the purpose of effect.
In order to solve the above-mentioned technical problem, the present invention uses following technical scheme：
The butyl methacrylate production technology of a kind of high-efficiency environment friendly, it is characterised in that comprise the following steps：
(1) it is 1 in molar ratio by reaction raw materials n-butanol and methyl methacrylate:1.5~1:4, catalyst is by charging
The 0.5%~5% of gross mass, by 0.01%~0.1% input esterifying kettle of charging gross mass, esterifying kettle temperature is polymerization inhibitor
85 DEG C~115 DEG C, pressure be normal pressure, form esterification products through steam heating response in esterifying kettle, esterifying kettle material component presses
Weight ratio meter is：Methanol 1-3%, methyl methacrylate 10-20%, butanol 5-15%, butyl methacrylate 55-70%,
The degree of polymerization of butyl methacrylate is 3ppm~30ppm；
(2) esterifying kettle material enters esterification column in the form of azeotropic mixture, is unreacted methyl methacrylate in esterifying kettle
Ester and reaction generation methanol distillated from the tower top of esterification column, esterification column temperature is 85 DEG C~105 DEG C, pressure be 75kpa~
90kpa, the tower top temperature of esterification column is 50 DEG C~80 DEG C, is layered after condensed device condensation into phase-splitter, obtains ester phase
Methyl methacrylate, polymerization inhibitor is added, be back to esterification column, collect methanol；
(3) the kettle liquid part in esterification column is returned esterifying kettle through pump and flowed back again, and another part is neutralized, essence
Evaporate, obtain the butyl methacrylate that content is 99.0%~99.8%, wherein, be back in esterification column the kettle liquid of esterifying kettle with
Neutralized, the kettle liquid of rectifying than volume flow be 0.5:1-5:1.
Preferably, the neutralization described in step (3) refers to that kettle liquid enters neutralizing tower, carries out solid caustic soda neutralization.
It is further preferred that described solid caustic soda is solid NuaO, dosage is the 1-10 into the thick ester quality of neutralizing tower
Times, and regularly replace supplement.
Preferably, the rectifying in step (3), comprises the following steps：Into lightness-removing column, the bottom temperature of lightness-removing column is 85 DEG C
~115 DEG C, pressure be 10kPa~25kPa, the tower top temperature of lightness-removing column is 50 DEG C~80 DEG C, and pressure be 20kPa~30kPa, de-
The overhead distillate of light tower, adds polymerization inhibitor, is back to esterifying kettle；Lightness-removing column kettle material enters weight-removing column, the tower of weight-removing column
Kettle temperature degree is 85 DEG C~115 DEG C, Stress control is 5kPa~10kPa, and the tower top temperature of weight-removing column is 90 DEG C~105 DEG C, pressure
For 10kPa~20kPa, the overhead distillate of weight-removing column, polymerization inhibitor is added, be back to the addition of esterifying kettle, wherein polymerization inhibitor
For the 0.01%~0.1% of distillate.
Preferably, described catalyst is selected from p-methyl benzenesulfonic acid, pyrovinic acid, ion exchange resin, p-methyl benzenesulfonic acid
In one kind；Described polymerization inhibitor is selected from methylnaphthohydroquinone THQ, 1,4-benzoquinone PBQ, MEHQ HQMME, 2- tert-butyl group to benzene
One or more in diphenol MTBHQ, 2,5 di tert butyl hydroquinone 2,5-DTBHQ.
Preferably, the input fresh feed flow of esterifying kettle control input amount hourly for total feed 40%~
90%.
Preferably, the kettle liquid circular flow of esterifying kettle is the 20-80% that flow hourly is total feed.
Preferably, esterifying kettle, the temperature of reboiler need to be back to first after reboiler heats by being back to the solution of esterifying kettle
For 90-120 DEG C.
Beneficial effects of the present invention：
The present invention is with traditional alkyd reaction advantage：
(1) synthesis phase is using ester exchange reaction as general principle, and raw material is the methyl methacrylate being easy to get, effectively
The situation of a large amount of technique waste waters can be produced by avoiding in traditional acid alcohol reaction, while on a catalyst, be taken using new catalyst
For traditional concentrated sulfuric acid, reaction condition is gentle, and side reaction is few, while low to equipment corrosion degree and easy recovery, extends so as to reach
Service life of equipment, energy-saving purpose.
(2) present invention gained byproduct methanol has higher economic value, and the mesh of coproduction is can reach with reference to other techniques
, so as to which further increase is taken in.
(3) input of each section of polymerization inhibitor of whole production technology, controls the generation of polymer to greatest extent so that raw material profit
Improved with rate, cost-effective, additional income.
(4) esterifying kettle bottom phegma heats into reboiler, by boiling the adjustment of system again, can not only ensure raw material
Fully reaction, while kettle temperature can also be effectively controlled to a certain extent, have the function that to avoid side reaction.
The present invention through over-churning, neutralization stage control, while yield is improved, compared with low reaction temperatures, kettle liquid circulate with
And the reasonable employment of polymerization inhibitor so that side reaction occurrence probability is effectively controlled.The present invention has effectively evaded tradition simultaneously
The generation problem of waste water, greatly reduces cost for wastewater treatment in technique, also advantageously in the protection to environment.
After the process implementing, because technique is simpler, it can effectively reduce the occurrence probability of side reaction and avoid the later stage
The difficulty of wastewater treatment, energy saving technology reach 5-10%, and production capacity can improve 10-20%, economic and environment-friendly, remarkable benefit.
Brief description of the drawings
Fig. 1 is the process chart of the production technology of the butyl methacrylate of the present invention；
Wherein：1-reaction mass；2-esterifying kettle；3-esterification column；4-esterification overhead condenser；5-esterification tower top point
Phase device；6-supplement polymerization inhibitor；7-recovery tower reclaims methanol；8-thick ester removes rectifying column；9-esterifying kettle reboiler.
Embodiment
Embodiment 1
, will in molar ratio 1 as shown in figure 1, the equipment of the production method of butyl methacrylate uses continuous feed：1.5
Add raw material n-butanol and methyl methacrylate and account for the catalyst pyrovinic acid of charging gross mass 0.5%, account for the total matter of charging
The polymerization inhibitor phenthazine of amount 0.05% is directly added in esterifying kettle 2, feeds the flow velocity addition with 800L/h.Raw material is by heating
Esterification is carried out in esterifying kettle 2 afterwards, for the temperature of esterifying kettle 2 at 95 DEG C~115 DEG C, pressure is normal pressure.Keep esterifying kettle circulation
Flow 560L/h or so, 93 DEG C or so of 9 temperature of reboiler.Product passes through azeotropic distillation after reaction, and azeotropic mixture is entered with binary form
Enter esterification column 3 to be separated, the tower top temperature of esterification column 3 is at 64 DEG C or so.The overhead distillate of esterification column 3 is cold through being esterified tower top
Condenser 4 condenses, be esterified the split-phase of tower top phase-splitter 5 after, ester and water return esterification with a small amount of supplement polymerization inhibitor phenthazine in phase-splitter 5
Tower 3 is used as backflow；A kettle liquid part in esterification column 3 is returned esterifying kettle through pump and circulated again, during another part is carried out
With, rectifying, be recycled in esterification column esterifying kettle and neutralized, the kettle liquid of rectifying ratio is 0.8:1, keep thick ester in esterification column to contain
Amount 65% or so.After the thick neutralized tower of ester neutralizes in esterification column 3, handled through rectifying section, rectifying section mainly divides lightness-removing column and de- weight
Tower, it is rear to obtain the finished product butyl methacrylate that content is 99.55%.
Esterification Stage stability contorting kettle water content between 60%~70%, is esterified in overhead reflux and inhibited in thick ester content
The input of agent has been greatly reduced esterification side reaction odds, and the content of heavy constituent is effectively controlled in thick ester and kettle liquid
System.
Thus, this technique substitution classical acid alcohol esterification reaction, effectively prevent the production of traditional handicraft waste water, poisonous hydrochlorate
It is raw, while raw material methyl methacrylate is cheap and easy to get, production cost reduces 30%~50%.Simultaneously compared with the weight of low polymer
Component also make it that cracking required quantity of steam substantially reduces by 20%~45%, and energy consumption is greatlyd save while ability yield is improved.
Embodiment 2
As shown in figure 1, the equipment of the production method of butyl methacrylate uses continuous feed, in molar ratio 1：2 add
Raw material n-butanol and methyl methacrylate, with accounting for the catalyst pyrovinic acid of charging gross mass 2%, accounting for charging gross mass
0.07% polymerization inhibitor phenthazine is directly added in esterifying kettle 2, and the flow velocity that charging total amount is 800L/h adds.Raw material is by adding
Esterification is carried out after heat in esterifying kettle 2, the temperature of esterifying kettle 2 is at 95 DEG C~115 DEG C.Keep tower reactor circular flow 560L/h left
The right side, 93 DEG C or so of 9 temperature of reboiler.Product passes through azeotropic distillation after reaction, and azeotropic mixture is carried out with binary form into esterification column 3
Separation, the tower top temperature of esterification column 3 is at 64 DEG C or so.The overhead distillate of esterification column 3 condenses through being esterified overhead condenser 4, ester
After changing the split-phase of tower top phase-splitter 5, ester and water return the work backflow of esterification column 3 with a small amount of supplement polymerization inhibitor phenthazine in phase-splitter 5
With the kettle liquid part in esterification column 3 is returned esterifying kettle through pump and circulated again, and another part is neutralized, rectifying, esterification
Ta Neinei is recycled to esterifying kettle and neutralized, the kettle liquid of rectifying ratio is 1.5:1, keep thick ester content 65% in esterification column left
It is right.After the thick neutralized tower of ester neutralizes in esterification column 3, handled through rectifying section, rectifying section mainly divides lightness-removing column and weight-removing column, rear to obtain
Content is 99.55% finished product butyl methacrylate
Esterification Stage stability contorting kettle water content is esterified the input of polymerization inhibitor in overhead reflux between 60%~75%
Greatly reduce and be esterified side reaction odds, the content of heavy constituent is effectively controlled in thick ester and kettle liquid.
Thus, this technique substitution classical acid alcohol esterification reaction, effectively prevent the production of traditional handicraft waste water, poisonous hydrochlorate
It is raw, while raw material methyl methacrylate is cheap and easy to get, production cost reduces 30%~50%.Simultaneously compared with the weight of low polymer
Component also make it that cracking required quantity of steam substantially reduces by 20%~45%, and energy consumption is greatlyd save while ability yield is improved.
Claims (5)
1. the butyl methacrylate production technology of a kind of high-efficiency environment friendly, it is characterised in that comprise the following steps：
(1) it is 1 in molar ratio by reaction raw materials n-butanol and methyl methacrylate：1.5~1：4, catalyst is by the total matter of charging
The 0.5%~5% of amount, polymerization inhibitor is put into esterifying kettle by the 0.01%~0.1% of charging gross mass, through steam heating response shape
Into esterification products, esterifying kettle temperature is 85 DEG C~115 DEG C, pressure is normal pressure；
(2) esterifying kettle material enters esterification column in the form of azeotropic mixture, and wherein azeotropic mixture component is using weight ratio meter as methanol 1-
3%, methyl methacrylate 10-20%, butanol 5-15%, wherein butyl methacrylate 55-70%, butyl methacrylate
The content of polymer be 3ppm~30ppm, the methanol of unreacted methyl methacrylate and reaction generation is from esterification column
Tower top distillates, and esterification column temperature is 85 DEG C~105 DEG C, pressure is 75KPa~90KPa, the tower top temperature of esterification column for 50 DEG C~
80 DEG C, it is layered after condensed device condensation into phase-splitter, obtains ester phase methyl methacrylate, add polymerization inhibitor, backflow
To esterification column, methanol is collected；
(3) the kettle liquid part in esterification column is returned esterifying kettle through pump and circulated again, and another part enters neutralizing tower, carries out
Solid caustic soda neutralizes, rectifying, obtains the butyl methacrylate that content is 99.0%~99.8%, wherein, through pump circulation in esterification column
To esterifying kettle kettle liquid and neutralized, the kettle liquid of rectifying ratio be by volume flowmeter 0.5:1-5:1；
Described solid caustic soda is solid NuaO, and dosage is and the regular replenishment replacing into 1-10 times of the thick ester quality of neutralizing tower；
Rectifying wherein in step (3), comprises the following steps：Into lightness-removing column, the bottom temperature of lightness-removing column is 85 DEG C~115
DEG C, pressure be 10KPa~25KPa, the tower top temperature of lightness-removing column is 50 DEG C~80 DEG C, and pressure is 20KPa~30KPa, lightness-removing column
Overhead distillate, add polymerization inhibitor, be back to esterifying kettle；Lightness-removing column kettle material enters weight-removing column, the tower reactor temperature of weight-removing column
It is 5KPa~10KPa to spend for 85 DEG C~115 DEG C, Stress control, and the tower top temperature of weight-removing column is 90 DEG C~105 DEG C, and pressure is
10KPa~20KPa, the overhead distillate of weight-removing column, polymerization inhibitor is added, is back to esterifying kettle, the addition of wherein polymerization inhibitor is
The 0.01%~0.1% of distillate.
2. production technology according to claim 1, it is characterised in that described catalyst is selected from pyrovinic acid, ion is handed over
The one kind changed in resin, p-methyl benzenesulfonic acid；Described polymerization inhibitor is selected from methylnaphthohydroquinone THQ, 1,4-benzoquinone PBQ, MEHQ
One or more in HQMME, 2- TBHQ MTBHQ, 2,5 di tert butyl hydroquinone 2,5-DTBHQ.
3. production technology according to claim 1, it is characterised in that the input fresh feed flow of esterifying kettle is controlled every
The 40%~90% of the total feed of hour.
4. production technology according to claim 1, it is characterised in that the kettle liquid circular flow of esterifying kettle is stream hourly
Measure the 20-80% for total feed.
5. production technology according to claim 1, it is characterised in that esterifying kettle circulation kettle liquid all needs first to heat through reboiler
Afterwards, esterifying kettle is recycled to, reboiler outlet temperature is 90-120 DEG C.
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| CN201510855496.5A CN105481688B (en) | 2015-11-27 | 2015-11-27 | A kind of butyl methacrylate production technology of high-efficiency environment friendly |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109988066A (en) * | 2018-12-21 | 2019-07-09 | 江门谦信化工发展有限公司 | A kind of n-butyl acrylate industrialized producing technology reducing brine waste |
| WO2020261720A1 (en) * | 2019-06-28 | 2020-12-30 | 旭化成株式会社 | Method for producing methyl methacrylate |
| CN113457186B (en) * | 2020-03-30 | 2022-10-04 | 中石油吉林化工工程有限公司 | Method for improving separation effect of crude MMA (methyl methacrylate) separation tower |
| CN114195300B (en) * | 2021-12-08 | 2023-12-05 | 珠海谦信新材料有限公司 | Treatment system for waste residue liquid of acetate esterification kettle |
| CN115490590A (en) * | 2022-08-29 | 2022-12-20 | 平湖石化有限责任公司 | Butyl acrylate continuous production process with acrylic acid circulation |
| CN115350727B (en) * | 2022-10-21 | 2023-01-24 | 河北工业大学 | Modified sulfonic acid resin catalyst and preparation method and application thereof |
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| US5183930A (en) * | 1992-06-17 | 1993-02-02 | Rohm And Haas Company | Transesterification catalyst |
| CN101274890A (en) * | 2007-03-27 | 2008-10-01 | 罗姆有限公司 | Continuous preparation of alkyl esters of (meth) acrylic acid |
| CN104610059A (en) * | 2015-01-15 | 2015-05-13 | 吉林化工学院 | Method for synthesizing methyl-acrylate through ester exchange and adsorption removal of methanol |
-
2015
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183930A (en) * | 1992-06-17 | 1993-02-02 | Rohm And Haas Company | Transesterification catalyst |
| CN101274890A (en) * | 2007-03-27 | 2008-10-01 | 罗姆有限公司 | Continuous preparation of alkyl esters of (meth) acrylic acid |
| CN104610059A (en) * | 2015-01-15 | 2015-05-13 | 吉林化工学院 | Method for synthesizing methyl-acrylate through ester exchange and adsorption removal of methanol |
Non-Patent Citations (1)
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