CN107406364A - Method and apparatus for the production of diaryl carbonate - Google Patents
Method and apparatus for the production of diaryl carbonate Download PDFInfo
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- CN107406364A CN107406364A CN201680016660.6A CN201680016660A CN107406364A CN 107406364 A CN107406364 A CN 107406364A CN 201680016660 A CN201680016660 A CN 201680016660A CN 107406364 A CN107406364 A CN 107406364A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
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Abstract
This application describes the method for producing diaryl carbonate.Method, which is included in the first destilling tower, makes the step of dialkyl carbonate, aromatic alcohol and catalyst precarsor reaction are to produce diaryl carbonate.The step of method includes being used to make aromatic alcohol react to produce catalyst with catalyst precarsor in the first destilling tower.The step of method also includes being included in the first top stream of the alkylol gradually formed in the first destilling tower from the recovery of the first destilling tower.Application also describes the system of the production for diaryl carbonate.System includes the first destilling tower, and it includes one or more entrances.
Description
Related application
It is entitled " to be used for the method and dress of the production of diaryl carbonate this application claims European application number 15382138.4
Put (Method And Apparatus For The Production Of Diaryl Carbonate) " (March 23 in 2015
Day submit) priority and rights and interests, for any and whole purposes, the entire disclosure of which is incorporated herein by reference.
Technical field
The method and apparatus that present disclosure is generally directed to the production of diaryl carbonate.More specifically, the application
It is related to the method and apparatus of the production for diphenyl carbonate (" DPC ").
Background technology
Makrolon is useful material, its physics and optical property due to them and be taken seriously.Diaryl carbonate,
Such as DPC, it is important reactant in the production of makrolon.For example, can be by making bisphenol-A be reacted with DPC to manufacture
Makrolon.In early days, the method for the production of diaryl carbonate is used as reactant by the use of phosgene.However, the toxicity of phosgene promotees
Make the research and development of the non-phosgene process of the production based on intermediate dialkyl carbonate.
The production of diaryl carbonate generally includes two-step method.In the first step, dialkyl carbonate and aromatic alcohol are in ester
Reaction is to produce alkyl aryl carbonate in the presence of exchange catalysts, e.g., phenyl methyl carbonic ester and alkylol (alkanol),
Such as methanol (Fig. 1).Then, in the second step described in fig. 2, the alkyl aryl carbonate experience disproportionation of two molecules is anti-
Should be with the diaryl carbonate of one molecule of generation, such as DPC, and the dialkyl carbonate of a molecule, such as DMC.
Although the reaction shown in Fig. 1 and Fig. 2 is the reaction that it is generally desirable to, numerous side reactions occur, generation is not wished
The accessory substance of prestige.These accessory substances can disturb the continuous production of desired product, reduce the efficiency of overall process, and one
Waste stream is even produced in a little situations, it needs the special disposal for disposal.This is the situation of alkyl aryl ether, such as fennel
Ether, it is accessory substance caused by the reaction of dialkyl carbonate and aromatic alcohol.
Four phenol titaniums (titanium tetra phenoxide) (TTP) catalyst is used in the reaction described in fig. 2.
Because TTP high-melting-point and its relatively low solubility in phenol, TTP：The processing of phenol mixture is troublesome.This is again
Cause the catalyst of difference to be replaced, and also result in process piping blocking and pump operation problem, it causes equipment to stop work and produce
Loss.
Because TTP is not commercially available, it can be by tetraisopropoxy titanium (TPT) produced in situ of outsourcing.It is specific and
Speech, synthesizes TTP based on the reaction described in Fig. 3, wherein TPT and phenol reactant to produce TTP and isopropyl alcohol (IPA) by TPT.
In view of the relatively low fusing point and liquid of TPT at room temperature, can be caused in principle more as cocatalyst using TPT
Good treatment conditions.However, by forming isopropyl alcohol (IPA), TPT has the shortcomings that pollution products stream.Due to equipment topology
Structurally and operationally condition, IPA can reach DMC reactors (methanol e.g., produced in DPC equipment and the DMC end in equipment
Point), and IPA can damage DMC and subsequent DPC amount and purity.
Therefore, the method and apparatus for the production diaryl carbonate that byproduct of reaction is easily processed to offer in the art be present
Needs.
Also exist has by needs of the alkylol compared with the method and apparatus of the diaryl carbonate of of low pollution to recovery.
The content of the invention
The content of the invention is provided to introduce the selection of concept in simplified form, in its embodiment below further
Description.The content of the invention is not intended to be limiting the scope of claimed main body.By be related to for produce diaryl carbonate device,
The application of method and system largely meets foregoing needs.
In one aspect, this disclosure provides the method for producing diaryl carbonate.Method is included in the first steaming
Evaporating makes the step of dialkyl carbonate, aromatic alcohol and catalyst precarsor reaction are to produce diaryl carbonate in tower.Method is included in
The step of making aromatic alcohol be reacted with catalyst precarsor to produce catalyst in first destilling tower.Method also includes reclaiming from destilling tower
The step of first top is flowed, the first top stream is included in the alkylol gradually formed in the first destilling tower.Method can also include
The step of the first top is flowed is sent to after-fractionating tower.Method may further include from after-fractionating tower and reclaim second, the
It is second-rate including at least some alkylols and azeotropic mixture.Method includes the alkylol and azeotropic in separation second with being further adapted for
The step of thing.
On the other hand, this disclosure provides the system of the production for diaryl carbonate.System includes the first tower,
First tower includes one or more entrances.One or more entrances are received in dialkyl carbonate, aromatic alcohol and catalyst precarsor
One or more.Destilling tower also includes outlet.One or more entrances are with being used for dialkyl carbonate, aromatic alcohol and catalyst
One or more one or more intake pipelines connection in precursor.In embodiments, export to reclaim from the first destilling tower and wrap
Flow at the first top for including alkylol.In another embodiment, the after-fractionating tower included an inlet and an outlet is positioned at the first distillation
The downstream of tower.The entrance of after-fractionating tower is in fluid communication with the first top stream from the first destilling tower.After-fractionating tower goes out
Mouth recovery includes the second of alkylol and azeotropic mixture；Azeotropic mixture can include the first alkylol (methanol) and the second alkylol
(IPA).In still another embodiment, including the 3rd destilling tower of entrance and outlet at bottom is located at the downstream of after-fractionating tower.
The entrance of 3rd destilling tower and the second of after-fractionating tower are in fluid communication.Moreover, the outlet at bottom recovery alkane of the 3rd destilling tower
Base alcohol.
Some aspects of the application are so rather broadly summarised, so as to more fully understand its specific implementation
Mode, and so as to preferably recognize the contribution to prior art.Certainly, exist appended by will be described below and being formed
The another aspect of the application of claimed subject matter.
Brief description of the drawings
In order to contribute to the stronger understanding of the application, with reference now to accompanying drawing, wherein identical element is with same numbers mark
Note.These accompanying drawings are not necessarily to be construed as limiting the application and are only intended to be illustrative.
Fig. 1 illustrates dimethyl carbonate (DMC) and phenol to phenyl methyl carbonic ester PMC ester exchange reaction.
Fig. 2 illustrates PMC to diphenyl carbonate (DPC) disproportionated reaction.
Fig. 3 illustrates the reaction from titanium isopropoxide (TTP) and the phenol titanium (TPT) of phenol synthesis four.
Fig. 4 is illustrated according to example system of the present aspects for producing DPC.
Fig. 5 is illustrated according to example system of the another aspect of the application for producing DPC.
Embodiment
The detailed description of illustrative aspect will be discussed with reference to each accompanying drawing herein.Although this description provides possible reality
The detailed example applied, it should be noted that details is intended to illustrate and therefore do not limit scope of the present application.
By reference to accompanying drawing can obtain part disclosed herein, method and apparatus more complete understanding.Based on side
Just and easily present disclosure, these accompanying drawings (also referred herein as " scheming ") are only to schematically show, and therefore,
Its relative size for being not intended to indicate its device or part and size and/or the scope for defining or limiting embodiment.Although it is
Clear, in the following description using concrete term, but these terms are intended to only refer to and selected in the accompanying drawings for explanation
The specific structure of embodiment, it is not intended that define or limit scope of the present disclosure.In accompanying drawing and following subsequent description
In, it should be understood that identical numerical designation refers to the part of identical function.
Refer to that " one side ", " aspect ", " one or more aspects " etc. are meant with reference to embodiment party in this specification
Special characteristic, structure or the characteristic of formula description are included at least one aspect of present disclosure.It is moreover, each in the description
Term " aspect " not necessarily refers to identical aspect in individual place.That is, description can be showed by some aspects rather than other aspects
Each feature.Any range provided herein includes all medians and is also what be can be combined.
Content disclosed herein discusses the purity for the product for improving recovery, improves catalyst treatment and therefore improve equipment
Reliability, improve whole efficiency, reduce energy consumption and reduce the new paragon of the holistic cost related to the production of diaryl carbonate.
The reactant being especially desired to used at industrial scale is DMC and phenol, and it reacts to produce DPC.Note
Meaning, for the ease of reference and as just non-limiting and exemplary materials, it is specific anti-to refer primarily to these in the de-scription below
Answer thing.
Various charging, product and recycle streams are disclosed in figure.It should be understood by one skilled in the art that as herein
Various stream/the pipelines of described positioning are, e.g., in " top " of particular column, " centre ", " top " or " side " be it is relative,
Because being introduced into or the physical location of salvage material depends on the condition that is kept in particular column.For example, " the bottom into tower
The stream in portion " can actually enter some levels above collecting tank, include the reboiler of tower, and leave the pipe at " top " of tower
Line/stream can actually leave some levels below top stage, include the condenser of tower.Therefore, including herein this kind of term,
For the general orientation being convenient for reference to describe on each tower and pipeline/stream, and this kind of term is not intended to limitation one really
Cut position.
Moreover, tower mentioned in this article can be connected with each other by a series of chargings/pipeloop, it, which plays conveying, includes
The effect of the stream of reactant and/or product.The direction flowed in figure indicated by an arrow.The design aspect of specific installation is being adapted to,
Various valves, heater, pumping equipment, instrument, filter, analyzer and other accessories can be optionally included in shown in it
On pipeline.Although moreover, for illustration purposes, figure and their description can describe odd number container, such as reaction vessel or
Stainless steel, but it is to be understood that can use the multiple containers of serial or parallel connection in the place being adapted to.
Fig. 4 is illustrated according to system 400 of the embodiment for producing diaryl carbonate.System can in batch mode or
Continuous mode is run.System 400 can also be run with laboratory scale or commercial scale.
In particular aspects, diaryl carbonate is diphenyl carbonate (DPC).DPC is useful in the other applications such as PC synthesis
's.In one embodiment, having via the diaryl carbonate of the present processes and system production for recovery is less than about
1.0wt% or even less than 0.5wt% alkylol and/or its derivative.In a preferred embodiment, the virtue of carbonic acid two of recovery
Ester has less than alkylol and/or its derivative present in its of about 0.25wt%.
System 400 includes being used for the one or more intake pipelines for introducing reactant.It is at least one in intake pipeline to be used for
Introduce aromatic alcohol.Aromatic alcohol can include but is not limited to fragrant monohydroxy compound.Fragrant monohydroxy compound is not limited, as long as
Hydroxyl is bonded directly to aromatic group：The compound can be represented by the formula (1) being provided below.
Ar1OH (1)
Wherein Ar1Represent the aromatic group with 5 to 30 carbon atoms.
With this kind of Ar1The example of fragrant monohydroxy compound include phenol；Various alkylphenols, such as cresols are (different
Structure body), xylenols (isomers), pseudocuminol (isomers), tetramethyl phenol (isomers), ethyl -phenol (isomery
Body), propylphenol (isomers), butylphenol (isomers), diethyl phenol (isomers), Methylethyl phenol (isomery
Body), methyl-propyl phenol (isomers), dipropyl phenol (isomers), methyl butyl phenol (isomers), amyl phenol it is (different
Structure body), hexylphenol (isomers) and cyclohexylphenol (isomers)；Various alkoxy phenols, such as metoxyphenol (isomery
Body) and thanatol (isomers)；Aryl alkyl phenol, such as phenyl propyl phenol (isomers)；Naphthols (isomers) and
Various substituted naphthols；With heteroaryl perfume (or spice) monohydroxy compound, such as pyridone (isomers), Hydroxycoumarin (isomers) and
Oxyquinoline (isomers).Those more preferably used in this application are wherein Ar1It is the fragrance with 6 to 10 carbon atoms
The unsubstituted phenol and fortified phenol of group.Unsubstituted phenol is especially preferred.Moreover, in these fragrant monohydroxy compounds
In, in this application preferably using the fragrant monohydroxy compound for not including halogen substantially.
According to still another embodiment, aromatic alcohol can include cresols, xylenols, phenol, pseudocuminol, tetramethyl
Phenol, ethyl -phenol, propylphenol, butylphenol, diethyl phenol, Methylethyl phenol, methyl-propyl phenol, dipropyl benzene
Phenol, methyl butyl phenol, amyl phenol, hexylphenol, cyclohexylphenol, metoxyphenol, thanatol, phenyl propyl benzene
Phenol, naphthols, ortho-homosalicylic acid ester and its combination.
As depicted in figure 4, phenol is introduced via pipeline 10 in system 400.Phenol is also referred to as carbolic acid and had to divide
Minor C6H5OH.That is, oh group is attached to unsaturated aromatic rings, such as phenyl ring.Therefore, because conjugate base passes through in aromatic rings
The stabilization of resonance, phenol have the acidity bigger than usual alcohol.Individually, at heat exchanger 12, the phenol from pipeline 10
Mixed with the phenol (PhOH circulations) from pipeloop.Then, the phenol of mixing enters tower 210.
Another intake pipeline can be used for introducing dialkyl carbonate to system 400.The example of dialkyl carbonate is general
Including the carbonate group being placed between two alkyl groups.Example includes but is not limited to dimethyl carbonate, diethyl carbonate, carbon
Sour dipropyl, diallyl carbonate, carbonic acid dibutene ester, dibutyl carbonate, diamyl carbonate, carbonic acid dihexyl, carbonic acid two heptan
Ester, carbonic acid dioctyl ester, the nonyl ester of carbonic acid two, carbonic acid didecyl, the ring pentyl ester of carbonic acid two, dicyclohexyl carbonate, the cycloheptyl ester of carbonic acid two, carbon
Acid benzhydryl ester, dipheryl carbonate ethyl ester, two (phenyl propyl) carbonic esters, two (phenyl butyl) carbonic esters, two (chlorophenylmethyl) carbon
Acid esters, two (mehtoxybenzyl) carbonic esters, two (methoxy) carbonic esters, two (methoxy ethyl) carbonic esters, two (chloroethenes
Base) carbonic ester, two (cyano ethyl) carbonic esters and its combination.
As depicted in figure 4, DMC is introduced via pipeline 30 in system 400.Moreover, at heat exchanger 32, from following
The DMC of endless tube line 120 mixes with the DMC from pipeline 30.Then the DMC mixed enters tower 210.
The dialkyl carbonate used in the present invention is the compound represented by formula (2).
R1OCOOR1 (2)
Wherein R1Represent the alkyl group with 1 to 10 carbon atom, the alicyclic group with 3 to 10 carbon atoms or
Aromatic alkyl group with 6 to 10 carbon atoms.
R1Example include alkyl group, such as methyl, ethyl, propyl group (isomers), pi-allyl, butyl (isomers),
Cyclobutenyl (isomers), amyl group (isomers), hexyl (isomers), heptyl (isomers), octyl group (isomers), nonyl (isomery
Body), decyl (isomers) and cyclohexyl methyl；Alicyclic group, such as cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl and cycloheptyl
Base；And aromatic alkyl group, such as benzyl, phenethyl (isomers), phenyl propyl (isomers), phenyl butyl (isomers) and
Methylbenzyl (isomers).Alkyl group, alicyclic group and aromatic alkyl group above-mentioned can be substituted by other
Base --- such as low-grade alkyl group, lower alkoxy groups, cyano group or halogen atom --- substitutes, and wherein may be used also
To include unsaturated bond.
It is (different that the example of dialkyl carbonate with this kind of R1 includes dimethyl carbonate, diethyl carbonate, dipropyl carbonate
Structure body), diallyl carbonate, carbonic acid dibutene ester (isomers), dibutyl carbonate (isomers), diamyl carbonate (isomery
Body), carbonic acid dihexyl (isomers), the heptyl ester of carbonic acid two (isomers), carbonic acid dioctyl ester (isomers), the nonyl ester (isomery of carbonic acid two
Body), carbonic acid didecyl (isomers), the ring pentyl ester of carbonic acid two, dicyclohexyl carbonate, the cycloheptyl ester of carbonic acid two, dipheryl carbonate methyl esters, carbon
Sour two phenethyl esters (isomers), two (phenyl propyl) carbonic esters (isomers), two (phenyl butyl) carbonic esters (isomers), two
(chlorophenylmethyl) carbonic ester (isomers), two (mehtoxybenzyl) carbonic esters (isomers), two (methoxy) carbonic esters,
Two (methoxy ethyl) carbonic esters (isomers), two (chloroethyl) carbonic esters (isomers) and two (cyano ethyl) carbonic esters are (different
Structure body).
In these dialkyl carbonates, such dialkyl carbonate, wherein R are preferably used in the application1It is
Alkyl group with not more than four carbon atom and not comprising halogen atom.Particularly preferred one kind is dimethyl carbonate.
Moreover, in preferable dialkyl carbonate, it is especially preferred those be not include the carbon that the state of halogen produces substantially
Acid dialkyl ester, for example, by not including the alkylene carbonate of halogen substantially and not including the alcohol production of halogen substantially
Those.
The mol ratio of dialkyl carbonate and fragrant monohydroxy compound can be in the range of 0.1 to 10.It is highly preferred that
Mol ratio above can be in the range of 0.5 to 5, and in the range of more preferably 0.5 to 3.Outside the scope, relative to
The desired amount of alkyl aryl carbonate, the quantitative change of remaining unreacted material are high.This is probably inefficient.In addition, need
Significantly more energy is wanted to reclaim the unreacted material.
In the one side of the application, tower 210 can have bottom reaction segmentation and top reaction segmentation.Chemical reaction can
It is segmented with occurring to react in bottom.Reactive moieties can be equipped with filling or fixing internals, so as to provide at least three theoretical distillation
Level, also referred to as tower tray.For example, the reaction segmentation of tower 210, which can have, is than or equal to 10 tower trays.It is highly preferred that tower 210 can
With with the tower tray between 10 and 60.On the other hand, tower 210 can have the distillation level (tower tray) between 15 and 40.
It can use and not advise filler and/or whole block filler.Specifically, can use with big surface area, good wet
Profit and the filler of liquid phase residence time, such as, for example, Novalax rings, CY fillers etc..Fixed internals can also be used, such as
Tray tower, and instantiation includes but is not limited to sieve aperture tower tray, float valve tray and bubble cap tray.It can also be urged to multiphase
The tower of agent bed or other units addition soluble catalyst.
Another intake pipeline into system can be used for catalyst.The example of catalyst includes but is not limited to be catalyzed
Into destilling tower 210 reactant be used for produce diaryl carbonate those.Catalyst or catalyst precarsor can be included but not
It is limited to iron, copper, nickel, cobalt, zinc, ruthenium, rhodium, palladium, silver, cadmium, rhenium, osmium, iridium, platinum, gold, mercury, zinc, tin, lead and including in aforementioned metal
At least one combination, and foregoing metal-organic complex.Specifically, catalyst can include titanium.More specifically, catalysis
Agent can be titanium isopropoxide (TPT), titanium tetrachloride, isobutyl group titanium, four titanium butoxides (TBT) and combinations thereof.Such as table 1 below institute
Show, TPT has the treatment characteristic of the raising better than TTP.
Table 1
Catalyst concn should be sufficiently high to produce acceptable yield, but compatibly below such concentration：Its
The solid for causing catalyst in destilling tower 210 is settled or equipment blocks.When homogeneous, catalyst can be with the shape that dissolves or suspend
Formula is introduced into reactant mixture together with the stream comprising aromatic alcohol.Alternatively, for example, reaction alcohol or suitable lazy can be introduced
Catalyst in property solvent.Heterogeneous catalyst can be used in packed bed, tower or special distillation arrangement.
As shown in Figure 4, catalyst enters system by pipeline 20.Moreover, catalyst circulation can be with brand-new catalyst
Mixing.As shown in Figure 4, brand-new catalyst can be cocatalyst, e.g., TPT.In one aspect, the catalyst of circulation can
With including TTP, TPT or its combination.On the other hand, the catalyst for mixing being introduced to reactive distillation column 210 is located at phenol input
The downstream of pipeline 10.In illustrative, non-limiting embodiment, the catalyst of mixing is introduced in the downstream of heat exchanger 12,
Although catalyst can be introduced in other positions.Precursor is also selected from titanium isopropoxide, titanium tetrachloride, isobutyl group titanium, four fourths
Epoxide titanium, with and combinations thereof.
In an illustrative embodiments, the tower 210 that phenol and DMC are reacted in the presence of a catalyst can include
Multiple various types of tower trays.Reboiler (e.g., kettle type reboiler) can be used, for heating tower.It can also make if desired
Use condenser.
The amount of the catalyst used in the present invention is according to catalyst type, the type of parent material compound and the ratio used
Example and reaction condition --- such as reaction temperature and reaction pressure --- and change.Gross weight based on parent material, catalysis
The amount of agent is usually by weight about 0.0001 to 30wt.%, preferably by weight 0.005 to 10wt.%, and more
In the range of preferably by weight 0.01 to 5wt.%.
On the other hand, for example, can in scope from a temperature of about 50 DEG C to 250 DEG C, in the presence of a catalyst,
Carry out the reaction between DMC and phenol.Destilling tower 210 may remain under 15 bars of gauge pressure (barg) to 35barg pressure, e.g.,
1,500 kPas (kPa) is to 3,500kPa.Within the range, can use more than or equal to 20barg's (2,000kPa)
Pressure.Also within the range, the pressure less than or equal to 28barg (2,800kPa) can be used.
In this application, according to still another embodiment, reaction time of ester exchange reaction in destilling tower equivalent to reacting
The mean residence time of liquid.Reaction time is according to the parent material in the form and series of internals in destilling tower, charging to tower
Amount, the type of catalyst and amount, reaction condition and other machined parameters and change.Reaction time is typically small 0.01 to 10
When, preferably 0.05 to 5 hour and in the range of more preferably 0.1 to 3 hour.
The top of unit 210 can include following product：Alkylol, DMC, methanol and anisole.In an exemplary reality
Apply in mode, methanol can be included by leaving 210 pipeline 40：DMC：Anisole, and other relatively light/heavier components.These are secondary
Product provides via pipeline 40, and pipeline 40 is divided into single pipeline 40a and 40b by separator 41 in downstream.
Pipeline 40a conveyings anisole, DMC and methanol.Pipeline 40a is fed to tower 810, and it can include stripping level, cold
Condenser and reboiler.810 bottom product is rich in anisole and including a small amount of phenol, DMC and methanol.810 bottom includes
Pipeline 42 is to remove the product.810 top product is relative rich in DMC and including a small amount of anisole, phenol and methanol.810
Top product is recycled to unit 410 to be combined with pipeline 40b via pipeline 130.
Pipeline 40b includes alkylol, DMC and methanol and enters destilling tower 410 by top or by side.As above
Explained, the concentration of product in being depended on into the position of destilling tower into each gravity flow of destilling tower.
Destilling tower can include reboiler and condenser.Methanol and DMC mixture are defeated from 410 top via pipeline 55
Go out.In one embodiment, DMC and carbinol mixture can be azeotropic.
As depicted in figure 4,410 are left according to even another embodiment, the pipeline 60 that sides stream.The pipeline 60 that sides stream wraps
Include alkylol, DMC and methanol.The pipeline that sides stream is connected to tower 420.420 are located at 210 and 410 downstream.From 420, obtain
The azeotropic mixture of DMC/ methanol is as top product.Top product is left by pipeline 65 and is recycled to 410.In one aspect, wrap
The top product for including the azeotropic mixture of DMC/ methanol is combined with pipeline 130 or combined with stream 55.Meanwhile 420 bottom product includes
Stream rich in alkylol and at least some DMC.This, which is flowed through, is left 420 by pipeline 70 and is then abandoned from system 400.In a reality
Apply in mode, the stream is forwarded for burning.
It is discussed more fully below now via pipeline 47 from 210 bottom products left.Specifically, 210 are left
Pipeline 47 include PMC, phenol, DMC, production DPC, catalyst and other higher boiling products.In embodiments, leave
210 pipeline 47 can include DMC：Phenol：PMC：DPC, and remaining as heavy constituent and catalyst.Pipeline 47 is introduced into distillation
Tower 310.Therefore, 310 include PMC, phenol, DPC, titanium catalyst and HB.In one aspect, 310 can be rectifying column.The tower can
To carry out the separation of material based on boiling point, without driving simultaneous chemical reaction.
Export pipeline 49a and intake pipeline 49b connect with 410.DMC can be by pipeline 49a from or through between 410
310 pipeline 49b enter.DMC can also be sent to heat exchanger via the pipeloop 120 connected with pipeline 49a/b
32, the DMC of circulation is mixed with brand-new DMC before being moved to 210.It is as indicated above, in the presence of a catalyst, DMC
Initial reaction between phenol occurs in 210.
Export pipeline 48 includes DPC, PMC, phenol and titanium catalyst, and titanium catalyst includes catalyst and/or precursor.One
Individual aspect, DMC can be included from 310 export pipeline 48:Phenol:PMC:DPC, and remaining as heavy constituent and catalyst.
Export pipeline 48 connects with reaction tower 320.320 top product is phenol and left by pipeline 100.Pipeline 100 is phenol
Pipeloop, it is sent to heat exchanger 12, thus, the phenol of circulation is made before being sent to 210 and comes from pipeline 10
Brand-new phenol mixing.
320 bottom product includes PMC, DPC and catalyst.These products are sent to recovery unit via pipeline 50
200, it can be described as DPC/ catalyst recovery units.Recovery unit 200 includes the outlet 51 for PMC.PMC is circulated
It is sent back to pipeline 48 and then 320.DPC is sent to outlet for finally reclaiming or subsequent via pipeline 150
During use.Catalyst can be sent back to 210 via pipeloop.Preferably, enter 210 before, pipeloop with
Brand-new titanium tube line 20 connects.
Further embodiment is illustrated in Figure 5.Using as mentioned above for the similar structures key element of Fig. 4 discussion and introduction
Reactant.In Fig. 5 system 500, alkoxy titanates are introduced into reactive distillation column 210 as phenol and DMC
The catalyst of reaction.
By using alkoxy titanates, it is not necessary to sideed stream from 410.Therefore, in Figure 5 without diagram pipeline
55.Therefore, pipeline 60 includes methanol and the azeotropic mixture of DMC and alkylol.Pipeline 60 extends between 410 and 420.420 can be with
Including multiple levels and can be with equal to about 1:1 reflux ratio operation, although other reflux ratios be also it is suitable and according to
User's needs to set.Bottom product stream includes alkylol and methanol, and it leaves 420 via pipeline 70.Top product stream bag
Methanol and DMC azeotropic mixture are included, it leaves via pipeline 65.Azeotropic mixture can be recycled 410 or be reclaimed as just product.
Here is illustrative embodiment and does not play a part of limiting present disclosure or scope of the following claims.
Embodiment 1
The titanium butoxide of 13183kg/h brand-new phenol, 10274kg/h DMC and 25.5kg/h is fed into Fig. 4 institute
The DPC production equipments shown.Reaction occurs 210.The butanol of maximum concentration is along 410 towers, and it needs to use destilling tower, and processing is clearly
Wash stream.410 side draw stream includes mainly having DMC (93.5wt% DMC, 5.0wt% methanol and 1.5wt% butanol)
Stream.The stream is subjected to separating in 420 via distillation.The product of new destilling tower 420 is：Top azeotropic mixture methanol and DMC, together
When bottom will include the mixture of butanol and DMC.The bottom stream for being kept completely separate butanol is obtained, it mainly has 22kg/h butanol
With 1172kg DMC stream.The embodiment produces 14944kg/h high quality DPC.
Embodiment 2
The titanium isopropoxide of 13025kg/h brand-new phenol, 8293kg/h DMC and 20kg/h is fed and retouched into Fig. 5
The DPC production equipments stated.In this case, the isopropanol (IPA) of maximum concentration is in the top at 410 tops.6,472kg/h quilts
From with (69.9wt% methanol, 29.1wt% DMC, 0.7wt% CO2With 0.3wt% isopropanol) composition
410 distill.The stream is sent to new destilling tower.Newly the product of destilling tower is：The top azeotropic mixture of methanol and DMC, together
When bottom will include IPA and methanol mixture.Specifically, isopropanol of the bottom stream comprising 17kg/h and 23kg/h methanol.
Cleaning and burning bottom product stream.The DPC of equipment production 14925kg/h high quality.
Although method and system has been described in terms of specific aspect is counted as at present, present disclosure is not required to
It is limited in disclosed aspect.It is intended to include various modifications and similar cloth in the spirit and scope of the claims
Put, the scope of claim should be explained unanimously with most wide, so as to including all this kind of modifications and similar structures.Present disclosure
Any and all aspect including appended claims.
Further disclosure
Aspect 1. is used for the method for producing diaryl carbonate, and it includes：Make dialkyl carbonate, virtue in the first destilling tower
Aromatic and catalyst precarsor reaction, to produce diaryl carbonate.Method, which is additionally included in the first destilling tower, makes aromatic alcohol and catalysis
Agent precursors reaction is to produce catalyst.Method also includes flowing from the top of the first destilling tower recovery first, and it includes the first destilling tower
In the alkylol that gradually forms.
Method also includes sending the first top and flow to after-fractionating tower and include alkylol and common from after-fractionating tower recovery
Boil at least some of second in thing.Method can include at least some from the second flow separation alkylol.Diaryl carbonate can
With including diphenyl carbonate.In some embodiments, alkylol includes isopropyl alcohol, butanol, methanol or its combination.
In another embodiment, method includes the step of stream of the diaryl carbonate of remanufacture, the carbonic acid two of production
Aromatic ester has less than alkylol present in its of about 0.5wt.%.In the exemplary embodiment, the virtue of carbonic acid two of production
Ester has less than alkylol present in its of about 0.25wt.%.Wherein azeotropic mixture includes dialkyl carbonate and methanol.
The method of the aspect of aspect 2. 1, wherein reactions steps include dialkyl carbonate, aromatic alcohol and catalyst precarsor and produced
Aryl alkyl carbonic ester.
The method of the aspect of aspect 3. 2, further comprises making aryl alkyl carbonate reaction in the presence of catalyst precarsor
To produce diaryl carbonate.
The method of any one of 4. foregoing aspect of aspect, the step of further comprising to the 3rd destilling tower transmission second,
It is with 1:0.1 to 1:10 reflux ratio is run with from Azeotrope separation alcohol.
The method of the aspect of aspect 5. 4, wherein azeotropic mixture are communicated to dialkyl carbonate production unit.
The method of any one of 6. foregoing aspect of aspect, wherein second are reclaimed and connected from after-fractionating tower via sideing stream
Pass to the 3rd destilling tower.
The method of any one of 7. foregoing aspect of aspect, wherein second reclaim via the overhead of after-fractionating tower
And it is communicated to the 3rd destilling tower.
The method of any one of 8. foregoing aspect of aspect, wherein the alkylol selection according to present in second evaporates via side
Divide or overhead reclaims second.
The method of the aspect of aspect 9. any one of 6 or 7, further comprise circulation from the azeotropic mixture of the 3rd destilling tower recovery to
After-fractionating tower.
The method of any one of 10. foregoing aspect of aspect, wherein method, which produce, includes dialkyl carbonate part product stream, institute
State the alkylol that product stream includes being less than 1wt%.
The method of any one of 11. foregoing aspect of aspect, wherein second are sent to the 3rd destilling tower, and wherein
Three distillation operations include the stream of the alkylol less than 1wt% to produce.
The method of any one of 12. foregoing aspect of aspect, wherein dialkyl carbonate are selected from dimethyl carbonate, carbonic acid diethyl
Ester, dipropyl carbonate, diallylcarbonate, carbonic acid dibutene ester, dibutyl carbonate, diamyl carbonate, carbonic acid dihexyl, carbon
Sour two heptyl esters, carbonic acid dioctyl ester, the nonyl ester of carbonic acid two, carbonic acid didecyl, the ring pentyl ester of carbonic acid two, dicyclohexyl carbonate, the ring of carbonic acid two
Heptyl ester, dipheryl carbonate methyl esters, dipheryl carbonate ethyl ester, two (phenyl propyl) carbonic esters, two (phenyl butyl) carbonic esters, two (chlorobenzenes
Methyl) carbonic ester, two (mehtoxybenzyl) carbonic esters, two (methoxy) carbonic esters, two (methoxy ethyl) carbonic esters,
Two (chloroethyl) carbonic esters, two (cyano ethyl) carbonic esters, and combinations thereof.
The method of any one of 13. foregoing aspect of aspect, wherein aromatic alcohol are selected from cresols, xylenols, phenol, trimethyl
Phenol, tetramethyl phenol, ethyl -phenol, propylphenol, butylphenol, diethyl phenol, Methylethyl phenol, methyl-propyl benzene
Phenol, dipropyl phenol, methyl butyl phenol, amyl phenol, hexylphenol, cyclohexylphenol, metoxyphenol, ethoxybenzene
Phenol, phenyl propyl phenol, naphthols, ortho-homosalicylic acid ester, and combinations thereof.
The method of any one of 14. foregoing aspect of aspect, wherein catalyst precarsor be selected from titanium isopropoxide, titanium tetrachloride,
Isobutyl group titanium, four titanium butoxides, and combinations thereof.
The method of any one of 15. foregoing aspect of aspect, further comprises：Recovery includes the product stream of diaryl carbonate,
Product stream has less than alkylol present in its of 0.5wt.%.
The method of the aspect of aspect 16. 15, wherein product stream have less than alkylol present in its of 0.25wt.%.
The method of any one of 17. foregoing aspect of aspect, wherein diaryl carbonate include diphenyl carbonate.
The method of any one of 18. foregoing aspect of aspect, wherein alkylol include isopropyl alcohol, butanol, methanol or its
Meaning combination.
The method of any one of 19. foregoing aspect of aspect, wherein azeotropic mixture include dialkyl carbonate and methanol.
The method of any one of 20. foregoing aspect of aspect, wherein azeotropic mixture include the methanol less than 1wt%.
The method 1 of the aspect of aspect 21., wherein azeotropic mixture include the alkylol less than 1wt%.
The method 1 of the aspect of aspect 22., wherein azeotropic mixture include the alkylol less than 0.5wt%.
The system that aspect 23. is used for the production of diaryl carbonate, it includes：First destilling tower, including configure to receive carbon
One or more one or more entrances in acid dialkyl ester, aromatic alcohol and catalyst precarsor, and outlet.It is one or more
Entrance compatibly with for one or more input pipes one or more in dialkyl carbonate, aromatic alcohol and catalyst precarsor
Line connects.Outlet is suitably adapted to flow from the top of the first destilling tower recovery first, and the first top stream includes alkylol.
System also includes the after-fractionating tower positioned at the downstream of the first destilling tower, and after-fractionating tower includes an inlet and an outlet,
The entrance of after-fractionating tower includes alkyl with being in fluid communication, and exporting to be suitable to reclaim at the top of first from the first destilling tower
The second of alcohol and azeotropic mixture.System may further include the 3rd destilling tower positioned at the downstream of after-fractionating tower, and the 3rd steams
Evaporating tower includes entrance and outlet at bottom, and the entrance of the 3rd destilling tower and the second of after-fractionating tower are in fluid communication, and the 3rd
The outlet at bottom of destilling tower is suitable to recovery alkylol.
The system of the aspect of aspect 24. 23, the wherein outlet of after-fractionating tower is located in its side wall.
The system of the aspect of aspect 25. 23 or 24, wherein the 3rd destilling tower includes about 25 levels and with about 1:0.1 to
About 1:10 reflux ratio operation.
Any one of the aspect 23-25 of aspect 26. system, further comprises：The outlet of 3rd destilling tower is connected to
The pipeloop of the entrance of two destilling towers.
Any one of the aspect 23-26 of aspect 27. system, further comprises：Separation positioned at the downstream of after-fractionating tower
Device, separator are configured to the catalyst for separating diaryl carbonate and being formed by catalyst precarsor.
Any one of the aspect 23-27 of aspect 28. system, further comprises：For the pipeloop of catalyst, circulation pipe
It is to be in fluid communication with the entrance of the first destilling tower that line, which places separator,.
Any one of the aspect 23-28 of aspect 29. system, wherein system configuration are that azeotropic mixture is communicated into dialkyl carbonate
Ester production unit.
The system of the aspect of aspect 30. 24, wherein system can pass through the sidewall exit or after-fractionating tower of after-fractionating tower
Any of overhead recovery second.
To produce azeotropic mixture, it includes being less than for any one of the aspect 23-28 of aspect 31. system, wherein system configuration
1wt% alkylol.
Any one of the aspect 23-31 of aspect 31. system, wherein the 3rd destilling tower is configured to operation to produce including small
In the stream of 1wt% alkylol.
Aspect 32. is used for the method for producing diaryl carbonate, and it includes：It is catalyzed in the first destilling tower in tetraalkoxy titanium
Dialkyl carbonate is set to be reacted with aromatic alcohol in the presence of agent precursor, to produce including diaryl carbonate, the catalysis of four phenol titaniums
The product mixtures of agent and alkylol --- corresponding to alkyl of catalyst precarsor ---；And from described in product mixtures removal
Alkylol it is at least some, wherein what is removed at least some is influenceed by after-fractionating tower.
The method of the aspect of aspect 33. 32, further comprise any carbonic acid two that separation gradually forms in the first destilling tower
Arrcostab it is at least some.
Any one of the aspect 32-33 of aspect 34. method, wherein after-fractionating tower are run to produce including azeotropic mixture
Stream, azeotropic mixture include alcohol and dialkyl carbonate.
The method of the aspect of aspect 35. 34, wherein azeotropic mixture connect with the 3rd destilling tower, and the 3rd destilling tower is configured to separation altogether
Thing and alkylol are boiled, it is connected with further distillation unit.
The method of the aspect of aspect 36. 32, wherein alkylol are communicated to the as the overhead product of after-fractionating tower
Three destilling towers.
The method of the aspect of aspect 37. 32, wherein alkylol are communicated to the 3rd destilling tower as sideing stream for after-fractionating tower.
The method of the aspect of aspect 38. 36 or aspect 37, wherein the 3rd destilling tower is run to produce including less than 1wt%'s
The stream of alkylol.
The method of the aspect of aspect 39. 32, wherein method produce the product stream for including dialkyl carbonate, the product stream bag
Include the alkylol less than 1wt%.
Any one of the aspect 32-37 of aspect 40. or 39 method, wherein dialkyl carbonate include dimethyl carbonate or carbon
Diethyl phthalate.Provide other suitable dialkyl carbonates elsewhere herein.
Any one of the aspect 32-37 of aspect 41. or 39 method, wherein aromatic alcohol include cresols, xylenols, phenol,
Or its any combination.Provide other suitable aromatic alcohols elsewhere herein.
Any one of the aspect 32-37 of aspect 42. or 39 method, wherein catalyst precarsor are selected from titanium isopropoxide, tetrachloro
Change titanium, isobutyl group titanium, four titanium butoxides and combinations thereof.
Any one of the aspect 32-37 of aspect 43. or 39 method, further comprise that recovery includes the product of diaryl carbonate
Stream, product stream have less than alkylol present in its of 0.5wt.%.
The method of the aspect of aspect 44. 43, wherein product stream have less than alkylol present in its of 0.25wt.%.
The method of the aspect of aspect 45. 35, wherein the 3rd destilling tower is run to produce being total to including the alkylol less than 1wt%
Boil product stream.
The system that aspect 46. is used for the production of diaryl carbonate, it includes：First reactive distillation column, it includes being configured to
One or more entrances one or more in dialkyl carbonate, aromatic alcohol and tetraalkoxy titanium catalyst precarsor are received, with
And outlet, one or more entrances with for a kind of in dialkyl carbonate, aromatic alcohol and tetraalkoxy titanium catalyst precarsor or
A variety of one or more intake pipelines connections, outlet is suitable to receive from the first destilling tower flows at the top of first, the first top stream bag
Alkylol is included, reactive distillation column is configured to make dialkyl carbonate and aromatic alcohol anti-in the presence of tetraalkoxy titanium catalyst precarsor
Should, to produce the alkyl for including diaryl carbonate, corresponding four phenol titanium catalyst and alkyl corresponding to catalyst precarsor
The product mixtures of alcohol；After-fractionating tower positioned at the downstream of the first destilling tower, after-fractionating tower include an inlet and an outlet, and second
The entrance of destilling tower is in fluid communication with the first top stream from the first destilling tower, and the outlet of after-fractionating tower is suitable to recovery
Second including alkylol；And the 3rd destilling tower is located at the downstream of after-fractionating tower, the 3rd destilling tower includes entrance and bottom
Portion exports, and the entrance of the 3rd destilling tower and the second of after-fractionating tower are in fluid communication, and the outlet at bottom of the 3rd destilling tower
Suitable for reclaiming alkylol.
The system of the aspect of aspect 47. 46, further comprises：The outlet of 3rd destilling tower is connected to entering for after-fractionating tower
The pipeloop of mouth.
Any one of the aspect 46-47 of aspect 48. system, further comprises：Separation positioned at the downstream of after-fractionating tower
Device, separator are configured to the catalyst for separating diaryl carbonate and being formed by catalyst precarsor.
Any one of the aspect 46-47 of aspect 49. system, further comprises：For the pipeloop of catalyst, for urging
It is to be in fluid communication with the entrance of the first destilling tower that the pipeloop of agent, which places separator,.
Any one of the aspect 46-47 of aspect 50. system, wherein system configuration are to circulate the aromatic alcohol reclaimed in system
Return the first reactive distillation column.
Any one of the aspect 46-47 of aspect 51. system, wherein system configuration include the alkyl less than 1wt% for generation
The azeotropic mixture product of alcohol.
Claims (20)
1. a kind of method for producing diaryl carbonate, it includes：
In the first destilling tower react in the presence of tetraalkoxy titanium catalyst precarsor dialkyl carbonate and aromatic alcohol with
Just produce include diaryl carbonate, four phenol titanium catalysts and corresponding to the catalyst precarsor alkyl alkylol product
Mixture；With
At least some alkylols are removed from the product mixtures, are removed described in wherein at least some by after-fractionating tower
Influence.
2. it is any according to the method for claim 1, to further comprise that separation gradually forms in first destilling tower
It is at least some in dialkyl carbonate.
3. according to the method for claim 1, wherein the after-fractionating tower is run to produce the stream including azeotropic mixture, institute
Stating azeotropic mixture includes alcohol and dialkyl carbonate.
4. according to the method for claim 3, wherein the azeotropic mixture is communicated to the 3rd destilling tower, the 3rd destilling tower
Separating azeotrope and alkylol are configured to, the alkylol is communicated to further distillation unit.
5. according to the method for claim 1, wherein the alkylol produces as the overhead of the after-fractionating tower
Thing is communicated to the 3rd destilling tower.
6. according to the method for claim 1, wherein the alkylol is connected as sideing stream for the after-fractionating tower
To the 3rd destilling tower.
7. according to the method described in claim 5 or claim 6, wherein the 3rd destilling tower is run to produce including small
In the stream of 1wt% alkylol.
8. according to the method for claim 1, wherein methods described produces the product stream for including dialkyl carbonate, the production
Logistics includes the alkylol less than 1wt%.
9. according to the method any one of claim 1-6 or 8, wherein the dialkyl carbonate is selected from carbonic acid diformazan
Ester, diethyl carbonate, dipropyl carbonate, diallyl carbonate, carbonic acid dibutene ester, dibutyl carbonate, diamyl carbonate, carbonic acid
Dihexyl, the heptyl ester of carbonic acid two, carbonic acid dioctyl ester, the nonyl ester of carbonic acid two, carbonic acid didecyl, the ring pentyl ester of carbonic acid two, dicyclohexyl carbonate,
The cycloheptyl ester of carbonic acid two, dipheryl carbonate methyl esters, dipheryl carbonate ethyl ester, two (phenyl propyl) carbonic esters, two (phenyl butyl) carbonic esters,
Two (chlorophenylmethyl) carbonic esters, two (mehtoxybenzyl) carbonic esters, two (methoxy) carbonic esters, two (methoxy ethyls)
Carbonic ester, two (chloroethyl) carbonic esters, two (cyano ethyl) carbonic esters, and combinations thereof.
10. according to the method any one of claim 1-6 or 8, wherein the aromatic alcohol be selected from cresols, xylenols,
Phenol, pseudocuminol, tetramethyl phenol, ethyl -phenol, propylphenol, butylphenol, diethyl phenol, ethyl methyl benzene
Phenol, methyl-propyl phenol, dipropyl phenol, methyl butyl phenol, amyl phenol, hexylphenol, cyclohexylphenol, methoxybenzene
Phenol, thanatol, phenyl propyl phenol, naphthols, ortho-homosalicylic acid ester, and combinations thereof.
11. according to the method any one of claim 1-6 or 8, wherein the catalyst precarsor be selected from titanium isopropoxide,
Titanium tetrachloride, isobutyl group titanium, four titanium butoxides, and combinations thereof.
12. according to the method any one of claim 1-6 or 8, further comprise that recovery includes the diaryl carbonate
Product stream, the product stream have less than 0.5wt.% its present in alkylol.
13. according to the method for claim 12, wherein the product stream has less than alkane present in its of 0.25wt.%
Base alcohol.
14. according to the method for claim 4, wherein the 3rd destilling tower is run to produce including the alkane less than 1wt%
The azeotropic product stream of base alcohol.
15. a kind of system of production for diaryl carbonate, it includes：
First reactive distillation column, it includes being configured to receive dialkyl carbonate, aromatic alcohol and tetraalkoxy titanium catalyst precarsor
Middle one or more one or more entrances, and outlet,
One or more of entrances with for dialkyl carbonate, one of aromatic alcohol and tetraalkoxy titanium catalyst precarsor or
Multiple intake pipeline connections,
The outlet is suitable to flow from the top of first destilling tower recovery first, and first top stream includes alkylol,
The reactive distillation column is configured to make dialkyl carbonate and aromatic alcohol in the presence of tetraalkoxy titanium catalyst precarsor
React to produce including diaryl carbonate, corresponding four phenol titanium catalyst and the alkyl corresponding to the catalyst precarsor
The product mixtures of alkylol；
After-fractionating tower, it is located at the downstream of first destilling tower, and the after-fractionating tower includes an inlet and an outlet,
The entrance of the after-fractionating tower is in fluid communication with first top stream from first destilling tower, and
The outlet of the after-fractionating tower is suitable to the second that recovery includes the alkylol；With
3rd destilling tower, its position include entrance and outlet at bottom in the downstream of the after-fractionating tower, the 3rd destilling tower,
The entrance of 3rd destilling tower is in fluid communication with the second of the after-fractionating tower, and
The outlet at bottom of 3rd destilling tower is suitable to reclaim the alkylol.
16. system according to claim 15, it further comprises：
Pipeloop, the outlet of the 3rd destilling tower is connected to the entrance of the after-fractionating tower by it.
17. according to the system any one of claim 15-16, it further comprises：
Separator, it is located at the downstream of the after-fractionating tower, the separator be configured to separate diaryl carbonate with by described
The catalyst that catalyst precarsor is formed.
18. according to the system any one of claim 15-16, it further comprises：
For the pipeloop of catalyst, it is to be steamed with described first that the pipeloop for catalyst, which places the separator,
The entrance for evaporating tower is in fluid communication.
19. according to the system any one of claim 15-16, wherein the system configuration is to return in the system
The aromatic alcohol of receipts is recycled back to first reactive distillation column.
20. according to the system any one of claim 15-16, wherein the system configuration includes being less than to produce
The azeotropic mixture product of 1wt% alkylol.
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| PCT/IB2016/051644 WO2016151508A1 (en) | 2015-03-23 | 2016-03-23 | Method and apparatus for the production of diaryl carbonate |
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| CN112759525A (en) * | 2020-12-14 | 2021-05-07 | 扬州市普林斯医药科技有限公司 | Preparation method of 2-methoxy ethylamine |
| CN113979865A (en) * | 2021-11-29 | 2022-01-28 | 中国成达工程有限公司 | Method for separating ternary system of butanol, diphenyl carbonate and phenol |
Citations (4)
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|---|---|---|---|---|
| US5284965A (en) * | 1992-03-12 | 1994-02-08 | Bayer Aktiengesellschaft | Process for preparing aromatic carbonates |
| JP2000072721A (en) * | 1998-08-31 | 2000-03-07 | Mitsubishi Gas Chem Co Inc | Supply of catalyst |
| CN101723834A (en) * | 2008-10-29 | 2010-06-09 | 深圳市飞扬实业有限公司 | Method for continuously producing carbonate mixed ester |
| CN104395279A (en) * | 2012-06-29 | 2015-03-04 | 沙特基础创新塑料Ip私人有限责任公司 | Method and apparatus for the production of diaryl carbonate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100305125B1 (en) * | 1994-02-08 | 2001-11-30 | 빌프리더 하이더 | Manufacturing Method of Diaryl Carbonate |
| JP2000191596A (en) * | 1998-12-25 | 2000-07-11 | Ge Plastics Japan Ltd | Production of aromatic carbonate |
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2016
- 2016-03-23 KR KR1020177026703A patent/KR102021812B1/en active IP Right Grant
- 2016-03-23 CN CN201680016660.6A patent/CN107406364A/en active Pending
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284965A (en) * | 1992-03-12 | 1994-02-08 | Bayer Aktiengesellschaft | Process for preparing aromatic carbonates |
| JP2000072721A (en) * | 1998-08-31 | 2000-03-07 | Mitsubishi Gas Chem Co Inc | Supply of catalyst |
| CN101723834A (en) * | 2008-10-29 | 2010-06-09 | 深圳市飞扬实业有限公司 | Method for continuously producing carbonate mixed ester |
| CN104395279A (en) * | 2012-06-29 | 2015-03-04 | 沙特基础创新塑料Ip私人有限责任公司 | Method and apparatus for the production of diaryl carbonate |
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| KR102021812B1 (en) | 2019-09-17 |
| WO2016151508A1 (en) | 2016-09-29 |
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