CN109651152A - A kind of method of unsaturated compound in removal Ester - Google Patents
A kind of method of unsaturated compound in removal Ester Download PDFInfo
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- CN109651152A CN109651152A CN201910036370.3A CN201910036370A CN109651152A CN 109651152 A CN109651152 A CN 109651152A CN 201910036370 A CN201910036370 A CN 201910036370A CN 109651152 A CN109651152 A CN 109651152A
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- unsaturated compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
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Abstract
The present invention provides a kind of methods of unsaturated compound in removal Ester, comprising: the mass ratio of pretreatment of raw material stage, oxidation reaction and refinement treatment, the oxidation reaction, oxidant and unsaturated compound is 0.6-25:1, reaction time 15S-3h；The pretreatment of raw material stage, 120-130 DEG C of pretreater column bottom temperature, 90-100 DEG C of tower top temperature, tower pressure interior force 1-3kpa.The refinement treatment, lightness-removing column pressure 3-5kpa, 100-110 DEG C of tower top temperature, 120-130 DEG C of column bottom temperature；Weight-removing column pressure 1-3kpa, 105-115 DEG C of tower top temperature, 130-140 DEG C of column bottom temperature.Using method of the invention, the processing for needing not move through higher reflux when more column plate number of plies rectifying column is just completely removed the unsaturated compounds such as dimethyl fumarate, obtains the higher dibasic acid dimethyl ester product of purity, quality reaches European Union requirements.
Description
Technical field
The present invention relates to a kind of methods of unsaturated compound in removal Ester, belong to technical field of fine.
Background technique
Dibasic acid dimethyl ester refer mainly to dimethyl succinate, dimethyl glutarate, dimethyl adipate single-component product or
Any mixture product, be esterified by binary acid and methanol, distill purification after obtain, be excellent plasticizer, and again
The high boiling solvent wanted, the substance are readily biodegradable, and have the good feature of environmental protection.
In addition to a kind of or more containing dimethyl succinate, dimethyl glutarate, dimethyl adipate in dibasic acid dimethyl ester
Outside kind main component, a small amount of unsaturated compounds are further comprised.European Union, which claims, in recent years forbids in the consumer goods using richness
Substances, this regulation such as horse dimethyl phthalate class unsaturated compounds seriously limit the application field of the product.
Chinese patent CN103965040B discloses a kind of method for preparing dibasic acid dimethyl ester, and this method is by binary
Acid, the dibasic acid half-ester recycled and methanol are added to the heated dissolution of mixing channel and obtain charging mixing after mixing
Object；Enter after incoming mixture is preheated by preheater from esterifier bottom, it is anti-that esterification occurs under catalyst
Reaction mixture should be made；Reaction mixture obtained is discharged from reactor head, successively passes through methanol rectifying tower, crystal evaporate tower
With dibasic acid dimethyl ester rectifying column, it respectively is isolated by methanol, water and dibasic acid dimethyl ester；Obtained dibasic acid dimethyl ester total content
99.6% or so.
Chinese patent CN101525446B discloses a kind of method for refining dibasic acid dimethyl ester plasticizer, for using continuous
Rectification under vacuum removes the mode of light component and heavy constituent to refine dibasic acid dimethyl ester plasticizer crude product, is by plasticizer crude product
First enter lightness-removing column after filtering, lightness-removing column decompression operation, removed overhead light component, lightness-removing column substrate material enters weight-removing column removing recombination
Point, weight-removing column is decompression operation, and weight-removing column removes the monoesters and a small amount of tar in plasticizer crude product, and weight-removing column tower top extracts essence
Plasticizer product after system.Dimethyl succinate 25%, dimethyl glutarate 52%, dimethyl adipate 22% in obtained product.
Chinese patent document CN102553124B discloses a kind of ozone treatment method of isooctyl ester nitrate, technical points
It is to be dissolved in water using ozone to generate the stronger hydroxyl radical free radical of oxidability, hydroxyl radical free radical and isooctyl ester nitrate in PH4-11
The principle of progress is not destroying original bituminous pavement using the method for isooctyl ester nitrate in ozone treatment bituminous pavement oil leak
On the basis of, it decomposes isooctyl ester nitrate completely, ultimately generates the carbon dioxide, water and nitrate that cannot corrode bituminous pavement
Class.
In conclusion the prior art has the disadvantage that
All Esters are all calculated in Chinese patent CN103965040B in mixed dibasic acid dimethyl ester not to fourth,
Penta, other ester impurities except oneself are removed；Chinese patent CN101525446B carries out impurity using the method for rectifying
Processing, since there are azeotropism, product purity is not high.Chinese patent document CN102553124B needs ozone being first dissolved in water
In be configured to certain ozone water solution and to guarantee the certain pH value of aqueous solution, use process is relatively complicated.
Summary of the invention
The present invention in order to solve the above technical problems, provides a kind of method for removing unsaturated compound in Ester,
To realize following goal of the invention:
(1) method of the invention is used, the processing for needing not move through higher reflux when more column plate number of plies rectifying column can obtain
To the higher dibasic acid dimethyl ester product of purity；
(2) method of the invention is used, the quality level of product is made to reach the standard of European Union requirements；
(3) method of the invention is used, the unsaturated compounds such as dimethyl fumarate in product can be completely removed, be made most
Finished product can be applied directly to can in the product of skin contact.
In order to solve the above technical problems, The technical solution adopted by the invention is as follows:
A kind of method of unsaturated compound in removal Ester, which is characterized in that unsaturated in the removal Ester
The method of compound, comprising: pretreatment of raw material stage, oxidation reaction and refinement treatment.
It is to the preferred technical solution of the present invention below:
The mass ratio of the oxidation reaction, oxidant and unsaturated compound is 0.6-25:1, reaction time 15S-3h.
The oxidant is the group of any one of potassium permanganate, hydrogen peroxide, ozone, sodium hypochlorite or wantonly two kinds or more
It closes.
The Ester is dibasic acid dimethyl ester, preferably dimethyl succinate, dimethyl glutarate, adipic acid diformazan
Ester single-component product or any mixture product.
The oxidation reaction, reaction vessel are any one of kettle, tower, pail pack, reservoir, pipeline reactor.
The oxidation reaction, after reaction, unsaturated compound content is 0ppm.
The unsaturated compound is the substance containing unsaturated chemical combination key, preferably butene dioic acid dimethyl ester, fumaric acid
Any one of dimethyl ester, glutaconate dimethyl ester, hexene diacid dimethyl ester or wantonly two kinds or more of combination.
The pretreatment of raw material stage, 120-130 DEG C of pretreater column bottom temperature, 90-100 DEG C of tower top temperature, tower internal pressure
Power 1-3kpa.
The refinement treatment, lightness-removing column pressure 3-5kpa, 100-110 DEG C of tower top temperature, 120-130 DEG C of column bottom temperature；It is de-
Heavy pressure tower 1-3kpa, 105-115 DEG C of tower top temperature, 130-140 DEG C of column bottom temperature.
The refinement treatment, after refinement treatment, ester content >=98.5%, unsaturated content of organics 0ppm, other impurities:
0.001-1.5%。
The pretreatment of raw material stage:
The dibasic acid dimethyl ester esterified material that esterification is obtained squeezes into pretreater by product pump by esterification column tower bottom, and tower top is de-
Except methanol and a small amount of light component, tower bottom removes heavy constituent, side take-off treated mixed dibasic acid dimethyl ester, pretreater
For negative-pressure operation, 120-130 DEG C of pretreater column bottom temperature is controlled, 90-100 DEG C of tower top temperature, tower pressure interior force 1-3kpa.
Principal component 99.14-98.26%, unsaturated compounds 8-3126ppm, other impurities in pretreated raw material
0.86-1.43%。
Reaction mechanism between this technology utilization unsaturated carbon carbon bond and oxidant, to realize in removal Ester
Unsaturated compound.
Carbon-carbon double bond is reacted with liquor potassic permanganate, and double bond is broken to obtain alcohol, ketone, acid and dioxy under different conditions
Change the different product of carbon；It reacts with ozone, carbon-carbon double bond can be fully disconnected, and be rearranged into ozonide；Then with hydrogen peroxide
Corresponding epoxides can be generated.
Triple carbon-carbon bonds are broken at three keys of carbochain after ozone or potassium permanganate oxidation, then through hydrolysis process, generate phase
The carboxylic acid answered.
Specific reaction is as follows
The oxidation reaction:
By ozone obtained, 4% acid permanganate soln, hydrogen peroxide, material carries out mutually in a reservoir with treated respectively
Contact is to achieve the purpose that remove unsaturated materials in product.Used oxidant in treated dibasic acid dimethyl ester
Unsaturated organic matter mass ratio be 0.6-25:1, reaction time 15S-3h, 20-35 DEG C of reaction temperature.Used reaction
Container includes but is not limited to the container that reaction kettle, pipeline, tubular reactor, material barrel, cup-shaped object etc. can hold material.
Unsaturated compounds 0ppm in material after oxidation.
The method of unsaturated compound in the removal Ester, further includes: the recycling of oxidant:
In the oxidation process for carrying out material, the dosage of oxidant is excessive, it is therefore desirable to access one in the end of reactor
A separator realizes the separation to material after oxidant and oxidation, is again introduced into reactor after the oxidant after separation is purified
It is recycled, the material after oxidation enters the next step and carries out refinement treatment.
The refinement treatment:
Material after reaction successively squeezes into lightness-removing column through product pump with weight-removing column, and the lightness-removing column and weight-removing column are negative pressure tower,
Lightness-removing column pressure 3-5kpa is kept, 100-110 DEG C of tower top temperature, 120-130 DEG C of column bottom temperature, removes the light component in product,
Lightness-removing column materials at bottom of tower squeezes into weight-removing column, keeps weight-removing column pressure 1-3kpa, and 105-115 DEG C of tower top temperature, column bottom temperature 130-
140 DEG C, so that tower top obtains final products.
The unsaturated content of organics 0ppm of obtained final products, principal component content >=98.5%.
Using above technical scheme, compared with the method for the prior art, the present invention is had the beneficial effect that:
(1) the method for the present invention is used, unsaturated compound in dibasic acid dimethyl ester product is thoroughly removed.
(2) the method for the present invention is used, is decomposed one of two kinds of substances similar in boiling point by way of oxidation,
Reduce the energy consumption in distillation process.
Specific embodiment
Hereinafter, preferred embodiments of the present invention will be described, it should be understood that preferred embodiment described herein is only used
In the description and interpretation present invention, it is not intended to limit the present invention.
The present invention is specifically described in the form of embodiment below:
The method of unsaturated compound in a kind of removal Ester of embodiment 1
The following steps are included:
(1) the pretreatment of raw material stage:
The dibasic acid dimethyl ester raw material that esterification is obtained, squeezes into pretreater, removed overhead by product pump by esterification column tower bottom
Methanol and a small amount of light component, tower bottom remove heavy constituent, and side take-off treated dibasic acid dimethyl ester, pretreater is negative pressure
Operation, 121 DEG C of pretreater column bottom temperature of control, 93 DEG C of tower top temperature, tower pressure interior force 1.2kpa.
Dimethyl succinate 12.06%, dimethyl glutarate 65.15%, dimethyl adipate in treated raw material
21.36%, unsaturated compounds 8ppm, other impurities 1.43%.
Reaction mechanism between this technology utilization unsaturated carbon carbon bond and oxidant, to realize in removal Ester not
Saturated compounds.
Carbon-carbon double bond is reacted with liquor potassic permanganate, and double bond is broken to obtain alcohol, ketone, acid and dioxy under different conditions
Change the different product of carbon；It reacts with ozone, carbon-carbon double bond can be fully disconnected, and be rearranged into ozonide；Then with hydrogen peroxide
Corresponding epoxides can be generated.
Triple carbon-carbon bonds are broken at three keys of carbochain after ozone or potassium permanganate oxidation, then through hydrolysis process, generate phase
The carboxylic acid answered.
Specific reaction is as follows:
(2) oxidation reaction:
Pretreated dibasic acid dimethyl ester raw material and oxidant are carried out by way of being mutually mixed contact in production process
The mass ratio of unsaturated compounds is 0.6:1, reaction time in reaction, ozone and pretreated dibasic acid dimethyl ester raw material
For 20S, 20 DEG C of reaction temperature, under the structure of the micro- flux of tubular reactor, two kinds of materials are in reactor by adequately connecing
Touching mass transfer is to achieve the purpose that remove unsaturated compounds in material.
Unsaturated compounds 0ppm in material after oxidation.
(3) recycling of oxidant:
In the oxidation process for carrying out material, the dosage of ozone is excessive, it is therefore desirable to access one in the end of reactor
Gas-liquid separator realizes separation to ozone and material, and the mixed gas gas containing ozone not reacted completely is from separator
Top outflow, is again introduced into reactor after purified and is recycled, and the material after oxidation is flowed out from separator bottom, under
One step process carries out refinement treatment.
(4) refinement treatment:
Material after reaction successively squeezes into lightness-removing column through product pump with weight-removing column, and the lightness-removing column and weight-removing column are negative pressure tower,
Lightness-removing column pressure 4.1kpa is kept, 109 DEG C of tower top temperature, 126 DEG C of column bottom temperature, removes the light component in product, lightness-removing column tower
Substrate material squeezes into weight-removing column, keeps weight-removing column pressure 2.3kpa, and 113 DEG C of tower top temperature, 136 DEG C of column bottom temperature, so that tower top obtains
To final products.
Dimethyl succinate 12.62%, dimethyl glutarate 65.13%, dimethyl adipate in obtained final products
21.04%, unsaturated compounds 0ppm, other impurities 1.21%.
The method of unsaturated compound in a kind of removal Ester of embodiment 2
The following steps are included:
(1) the pretreatment of raw material stage:
The dibasic acid dimethyl ester esterified material that will be obtained squeezes into pretreater, removed overhead first by product pump by esterification column tower bottom
Alcohol and a small amount of light component, tower bottom remove heavy constituent, side take-off treated dibasic acid dimethyl ester, and pretreater is that negative pressure is grasped
Make, 123 DEG C of pretreater column bottom temperature of control, 96 DEG C of tower top temperature, tower pressure interior force 1.5kpa.
Dimethyl succinate 26.32%, dimethyl glutarate 62.92%, dimethyl adipate in treated raw material
9.73%, unsaturated compounds 1135ppm, other impurities 0.92%.
Reaction mechanism between this technology utilization unsaturated carbon carbon bond and oxidant, to realize in removal Ester not
Saturated compounds.
Carbon-carbon double bond is reacted with liquor potassic permanganate, and double bond is broken to obtain alcohol, ketone, acid and dioxy under different conditions
Change the different product of carbon；It reacts with ozone, carbon-carbon double bond can be fully disconnected, and be rearranged into ozonide；Then with hydrogen peroxide
Corresponding epoxides can be generated.
Triple carbon-carbon bonds are broken at three keys of carbochain after ozone or potassium permanganate oxidation, then through hydrolysis process, generate phase
The carboxylic acid answered.
Specific reaction is as follows:
(2) oxidation reaction:
Pretreated dibasic acid dimethyl ester raw material and oxidant are carried out by way of being mutually mixed contact in production process
Reaction, the mass ratio of 4% acid permanganate soln and unsaturated compounds in pretreated dibasic acid dimethyl ester raw material are
5:1, reaction time 2h, are shaken in closed container by external force by 25 DEG C of reaction temperature, and two kinds of materials are in reactor
By sufficient mass transfer to achieve the purpose that remove unsaturated compounds in material.
Unsaturated compounds 0ppm in material after oxidation.
(3) recycling of oxidant:
In the oxidation process for carrying out material, the dosage of 4% acid potassium permanganate is excessive, it is therefore desirable at the end of reactor
The separation into an oil water separator realization to acid permanganate soln and material is terminated, acid permanganate soln is by separating
The dewatering outlet of device releases, and is again introduced into reactor and is recycled after re-processed, and the material after oxidation is gone out by separator
Hydraulic fluid port extraction enters the next step and carries out refinement treatment.
(4) refinement treatment:
Material after reaction successively squeezes into lightness-removing column through product pump with weight-removing column, and the lightness-removing column and weight-removing column are negative pressure tower,
Lightness-removing column pressure 3.2kpa is kept, 102 DEG C of tower top temperature, 125 DEG C of column bottom temperature, removes the light component in product, lightness-removing column tower
Substrate material squeezes into weight-removing column, keeps weight-removing column pressure 2.1kpa, and 111 DEG C of tower top temperature, 136 DEG C of column bottom temperature, so that tower top obtains
To final products.
Dimethyl succinate 26.11%, dimethyl glutarate 63.15%, dimethyl adipate in obtained final products
9.97%, unsaturated compounds 0ppm, other impurities 0.77%.
The method of unsaturated compound in a kind of removal Ester of embodiment 3
The following steps are included:
(1) the pretreatment of raw material stage:
Obtained mixed dibasic acid dimethyl ester esterified material squeezes into pretreater, removed overhead by product pump by esterification column tower bottom
Methanol and a small amount of light component, tower bottom remove heavy constituent, side take-off treated mixed dibasic acid dimethyl ester, and pretreater is
Negative-pressure operation, 129 DEG C of pretreater column bottom temperature of control, 97 DEG C of tower top temperature, tower pressure interior force 2.0kpa.
Dimethyl succinate 18.44%, dimethyl glutarate 54.85%, dimethyl adipate in treated raw material
25.54%, unsaturated compounds 3126ppm, other impurities 0.86%.
Reaction mechanism between this technology utilization unsaturated carbon carbon bond and oxidant, to realize in removal Ester not
Saturated compounds.
Carbon-carbon double bond is reacted with liquor potassic permanganate, and double bond is broken to obtain alcohol, ketone, acid and dioxy under different conditions
Change the different product of carbon；It reacts with ozone, carbon-carbon double bond can be fully disconnected, and be rearranged into ozonide；Then with hydrogen peroxide
Corresponding epoxides can be generated.
Triple carbon-carbon bonds are broken at three keys of carbochain after ozone or potassium permanganate oxidation, then through hydrolysis process, generate phase
The carboxylic acid answered.
Specific reaction is as follows:
(2) oxidation reaction:
Pretreated dibasic acid dimethyl ester raw material and hydrogen peroxide are carried out by way of being mutually mixed contact in production process
Reaction, the mass ratio of unsaturated compounds is 25:1 in hydrogen peroxide and pretreated dibasic acid dimethyl ester raw material, when reaction
Between be 3h, 35 DEG C of reaction temperature, phosphate-tungstic acid quaternary ammonium salt (Q3PW4O14, wherein Q be cetyltrimethyl ammonium contracting
Write) dosage be hydrogen peroxide 3 ‰, with stirring reaction kettle in, passed through in reactor by two kinds of materials of drive of stirring
Sufficient mass transfer is crossed to achieve the purpose that remove unsaturated compounds in material.
Unsaturated compounds 0ppm in material after oxidation.
(3) oxidant recycles:
In the oxidation process for carrying out material, the dosage of hydrogen peroxide is excessive, it is therefore desirable to access one in the end of reactor
A oil water separator realizes the separation to hydrogen peroxide and material, and hydrogen peroxide is released by the dewatering outlet of separator, after simple process
It is again introduced into reactor and is recycled, the material after oxidation enters the next step by the oil outlet extraction of separator and carries out essence
System processing.
(4) refinement treatment:
Material after reaction successively squeezes into lightness-removing column through product pump with weight-removing column, and the lightness-removing column and weight-removing column are negative pressure tower,
Lightness-removing column pressure 4.8kpa is kept, 110 DEG C of tower top temperature, 130 DEG C of column bottom temperature, removes the light component in product, lightness-removing column tower
Substrate material squeezes into weight-removing column, keeps weight-removing column pressure 3.0kpa, and 115 DEG C of tower top temperature, 140 DEG C of tower bottom temperature, so that tower top obtains
Final products.
Dimethyl succinate 18.83%, dimethyl glutarate 54.97%, dimethyl adipate in obtained final products
25.61%, unsaturated compounds 0ppm, other impurities 0.59%.
In this step oxidant be the substance with oxidation characteristic, including but not limited to ozone, hydrogen peroxide, potassium permanganate,
Sodium hypochlorite etc..
The reactor of oxidation reaction described in this step is the container that can hold material, including but not limited to reaction kettle, anti-
Answer tower, pail pack, tank, pipeline reactor etc..
The effect of technique: the unsaturated compounds as present in product are close with the boiling point of product, using traditional steaming
The effective of unsaturated compounds can not be realized in the lower situation of energy consumption for its effective removal, the oxidation technology by evaporating technique
Removal, realizes the raising of product purity.
Technical target of the product: color number≤10#, moisture≤0.01%, acid value≤0.13mgKOH/g, content >=98.57%, no
Saturation content of organics: 0.
Unless otherwise indicated, percentage employed in the present invention is weight percent, ratio of the present invention,
For mass ratio.
Finally, it should be noted that the foregoing is only a preferred embodiment of the present invention, it is not intended to restrict the invention,
Although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features.
All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in of the invention
Within protection scope.
Claims (10)
1. a kind of method of unsaturated compound in removal Ester, which is characterized in that
The method of unsaturated compound in the removal Ester, comprising: at pretreatment of raw material stage, oxidation reaction and purification
Reason.
2. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The mass ratio of the oxidation reaction, oxidant and unsaturated compound is 0.6-25:1, reaction time 15S-3h.
3. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The oxidant is the combination of any one of potassium permanganate, hydrogen peroxide, ozone, sodium hypochlorite or wantonly two kinds or more.
4. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The Ester is dibasic acid dimethyl ester, preferably dimethyl succinate, dimethyl glutarate, dimethyl adipate list
Component product or any mixture product.
5. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that described
Oxidation reaction, reaction vessel are any one of kettle, tower, pail pack, reservoir, pipeline reactor.
6. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that described
Oxidation reaction, after reaction, unsaturated compound content is 0ppm.
7. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The unsaturated compound is the substance containing unsaturated chemical combination key, preferably butene dioic acid dimethyl ester, fumaric acid diformazan
Any one of ester, glutaconate dimethyl ester, hexene diacid dimethyl ester or wantonly two kinds or more of combination.
8. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The pretreatment of raw material stage, 120-130 DEG C of pretreater column bottom temperature, 90-100 DEG C of tower top temperature, tower pressure interior force 1-
3kpa。
9. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The refinement treatment, lightness-removing column pressure 3-5kpa, 100-110 DEG C of tower top temperature, 120-130 DEG C of column bottom temperature；Weight-removing column
Pressure 1-3kpa, 105-115 DEG C of tower top temperature, 130-140 DEG C of column bottom temperature.
10. the method for unsaturated compound in a kind of removal Ester according to claim 1, which is characterized in that
The refinement treatment, after refinement treatment, ester content >=98.5%, unsaturated content of organics 0ppm, other impurities:
0.001-1.5%。
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| CN201910036370.3A CN109651152A (en) | 2019-01-15 | 2019-01-15 | A kind of method of unsaturated compound in removal Ester |
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| CN201910036370.3A CN109651152A (en) | 2019-01-15 | 2019-01-15 | A kind of method of unsaturated compound in removal Ester |
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