CN106699554A - Finish machining method of di(2-propylheptyl)ester adipate - Google Patents
Finish machining method of di(2-propylheptyl)ester adipate Download PDFInfo
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- CN106699554A CN106699554A CN201611164148.4A CN201611164148A CN106699554A CN 106699554 A CN106699554 A CN 106699554A CN 201611164148 A CN201611164148 A CN 201611164148A CN 106699554 A CN106699554 A CN 106699554A
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- Prior art keywords
- adipic acid
- ester
- propyl group
- group heptan
- propyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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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
Abstract
The invention discloses a finish machining method of a di(2-propylheptyl)ester adipate. The finish machining method comprises the following steps: step 1, introducing nitrogen gas into a reaction kettle, feeding 2-propyl heptanol and adipic acid into the reaction kettle, heating the materials to 150-180 DEG C, adding a metallic tin compound catalyst, and performing reaction for 2-3 hours; heating the materials to 200-225 DEG C, and when the acid value of the materials in the system is less than or equal to 0.25mgKOH/g, finishing reaction; step 2, removing excessive 2-propyl heptanol obtained in the step 1; step 3, introducing the nitrogen gas into the reaction kettle, cooling a product of the step 2 to 95-105 DEG C, performing neutralization, and purifying products by use of steam; and step 4, adding a porous adsorbing material into the reactant obtained in the step 3, stirring the materials, and filtering the mixture to obtain a finished product. The finish machining method has the advantages of suitability for industrial production and high purity; the prepared di(2-propylheptyl)ester adipate product has transparent appearance and no visible impurities.
Description
Technical field
The present invention relates to belong to technical field of fine, more particularly to adipic acid two（2- propyl group heptan）The finishing side of ester
Method.
Background technology
In plasticizer product, phthalate is to develop more early, most widely used class plasticizer.Due to it
With the advantage that plasticization effect is good and application performance is good, very big ratio is occupied in the production and consumption of plasticizer product.But
Due to the problem of its security for existing, in recent years nontoxic, the environmentally friendly plasticising of high-carbon alkoxide, vegetable oil base class and biological base class
Development, exploitation and the production of agent, show the situation accelerated development.With dioctyl adipate and di-n-octyl sebacate as representative
Dicarboxylic acids esters plasticizer, with the good transparency, cold resistance and cryogenic property.
And as obtained in adipic acid and 2- propyl enanthols are raw material adipic acid two（2- propyl group heptan）Ester product, with adipic acid two
Monooctyl ester is compared with di-n-octyl sebacate, with more preferable volatility resistance, cold resistance, heat resistance, resistance to extractable and durability, anti-fog
The property changed, combination property is more superior.It is a kind of new environmentally friendly class plasticizer.Due to the raw material 2- propyl enanthol early stages of the product
Only produced by the foreign countries such as BASF fewer companies, domestic whole dependence on import used, therefore to 2- propyl enanthols and its product of correlation
The research of product is less, makes slow progress.The adipic acid two of patent application 200910040889.5（2- propyl group heptan）Ester and preparation method thereof
And application, although the patent disclose adipic acid two（2- propyl group heptan）The synthetic method of ester, but the method is only limited to laboratory
The adipic acid two of small lot, low-purity（2- propyl group heptan）Ester study, but for industrial production, high-volume, high-purity oneself two
Acid two（2- propyl group heptan）Ester method for fine finishing is also to be studied.
The content of the invention
The present invention is in view of the shortcomings of the prior art, there is provided one kind is applied to that industrial production, purity is high, obtained adipic acid two
（2- propyl group heptan）The outward appearance of ester product is the transparent adipic acid two without visible foreign（2- propyl group heptan）The method for fine finishing of ester.
Chemical equation of the invention is as follows：
The present invention realizes solving above-mentioned technical problem by following technological means：A kind of adipic acid two（2- propyl group heptan）The essence of ester
Processing method, comprises the following steps：
Step one：To being passed through nitrogen in reactor, and 2- propyl enanthols and adipic acid put into the reactor；It is warmed up to
150~180 DEG C, metal tin compound catalyst is added, carry out 2 ~ 3h of reaction；200~225 DEG C are warmed up to, when material in system
Acid number be less than or equal to 0.25mgKOH/g when, reaction terminates；
Step 2：Excessive 2- propyl enanthols in removing step one；
Step 3：To nitrogen is passed through in reactor, the product of step 2 is cooled to 95~105 DEG C, neutralized, then by steam pair
Product is purified；
Step 4：To porous sorbing material is added in the reactant of step 3, finished product is filtered in stirring.
Preferably, 2- propyl enanthols in the step one：The mol ratio of adipic acid is 2.8 ~ 3.1:1.0,2- propyl enanthols,
After adipic acid is added, after maintaining 1 ~ 2h at 150~180 DEG C, then catalyst is added.
Preferably, 2- propyl enanthols in the step one：The mol ratio of adipic acid is 2.9:1.0.
Preferably, the removing in the step 2 includes two stages：First stage：At 185~200 DEG C, carry out
Normal pressure dealcoholysis, the dealcoholysis time is 0.5 ~ 1.5h；Second stage：Open vacuum carry out decompression dealcoholysis, control vacuum be-
0.075~-0.090Mpa, the dealcoholysis time is 0.5 ~ 2h.
Preferably, neutralized in the step 3 and using the NaOH aqueous solution of 3.5%wt, after standing, in separating
Water phase with after；Steam pressure is 0.70~0.80Mpa, and temperature is 175~190 DEG C, and the time of purification is 3.5~4.5 hours.
Preferably, the acid number for material being purified in the step 3 reaches 0.1mgKOH/g or below 0.1mgKOH/g.
Preferably, the porous sorbing material in the step 4 is activated carbon.
Preferably, the metallic tin chemical combination includes the one kind or several among stannous oxide, stannous oxalate, Dibutyltin oxide
The combination planted.
Preferably, the addition quality of the catalyst is the 0.5% of the quality that feeds intake of adipic acid.
It is a kind of to use above-mentioned adipic acid two（2- propyl group heptan）The adipic acid two of the method for fine finishing processing of ester（2- propyl group
Heptan）Ester, it is characterised in that：The adipic acid two（2- propyl group heptan）Colourity pt-co≤20 of ester, density are 0.915 ± 0.005g/
Cm3, flash-point（Opening agar diffusion method）>=203 DEG C, purity（GC methods）≥99.60%；Acid number≤0.10mgKOH/g.
The advantage of the invention is that：Method for fine finishing of the invention, compared to existing technology, in esterification process, N-process
In add inert gas, reaction mass is fully completely cut off with air, reduce reaction mass amount of oxidation, improve the matter of finished product
Amount, purity.Reacted stage by stage using two-step method, 150~180 DEG C is second stage for a stage, 200~225 DEG C；
So as to control reaction rate well so that carry out reacting balance.The generation by the way of steam purification, porous adsorbent absorption
Washed for tradition, reduce the consumption of raw water and the discharge capacity of sewage, energy consumption can be effectively reduced.
There is process of the invention preparation process to be easily controlled, and complete degree of reaction is high, the characteristics of product yield is high.It is made
Standby product has the advantages that high income, purity be high, quality better.The adipic acid two of preparation is processed through mode of the invention（2- third
Base heptan）Ester, its colourity（Pt-co) number≤20；Density（20℃）It is 0.915 ± 0.005g/cm3；Flash-point（Opening agar diffusion method）≥203
DEG C, purity（GC methods）≥99.60%；Acid number≤0.10mgKOH/g.Excellent product quality, purity is high.The yield of product reaches
More than 98.0%.
Specific embodiment
To further describe the present invention, it is described further with reference to embodiment.
Embodiment 1
A kind of adipic acid two（2- propyl group heptan）The preparation method of ester, comprises the following steps：
First, esterification reaction process：
To being passed through nitrogen in reactor（N2）, adipic acid and 2- propyl enanthols are pressed 1.0 under nitrogen protection:2.8 weight ratio,
During the 2- propyl enanthols of 3080kg are put into the reactor of 6m3, adipic acid 1100kg is put into again under agitation, heat up.
When temperature is raised to 150 DEG C, maintain 2.0 hours, add stannous oxide catalyst 5.5kg, be warmed up to 225 DEG C,
Maintenance reaction 3.5 hours.Sampling, measures acid number for 0.21mgKOH/g, and esterification terminates.
2nd, dealcoholysis process
At 185 DEG C, normal pressure dealcoholysis 1.5 hours, then under -0.090Mpa, decompression dealcoholysis 1.0 hours.Alcohol excess is removed altogether
With part Ester 630kg.
3rd, subtractive process
To being passed through nitrogen in reactor（N2）, the material that step 2 is obtained is cooled to 95 DEG C under nitrogen protection, add 120kg
Mass concentration be 3.5% NaOH solution；Stirring 30 minutes, stands 40 minutes, separation water phase.Again with the NaOH that 120kg is same
The aqueous solution carries out secondary N-process, separation water phase.
Directly to steam is passed through in product, the purification of product is carried out.Control steam pressure for 0.80Mpa, temperature is 185
DEG C, after 3.5 hours, sampling measures acid number for 0.09mgKOH/g, and flash-point is 205 DEG C.
4th, absorption and filter process
Material is cooled to 105 DEG C, 5Kg activated carbons are added, filtered after stirring.Collection filtrate is adipic acid two（2- propyl group heptan）
Ester product.Product 3155kg is obtained altogether.
After testing, product is the transparent oily liquids without visible foreign.Colourity（pt-Co):No. 20, density（20℃）,
0.913g/cm³；Flash-point（Opening agar diffusion method）：205℃；Acid number：0.07mgKOH/g, purity（GC methods）It is 99.66%；Product yield
It is 98.25%.
The present invention uses liquid chemical product colour measurement method（GB3143）Test colourity.
Embodiment 2
A kind of adipic acid two（2- propyl group heptan）The preparation method of ester, comprises the following steps：
First, esterification reaction process：
To being passed through nitrogen in reactor（N2）, adipic acid and 2- propyl enanthols are pressed 1.0 under nitrogen protection:3.1 weight ratio,
During the 2- propyl enanthols of 3100kg are put into the reactor of 6m3, the adipic acid of 1000kg is put into again under agitation.Heat up.
When temperature is raised to 180 DEG C, maintain 1.0 hours, add stannous oxide catalyst 3.0kg, stannous oxalate
2.0kg.It is warmed up to 210 DEG C, maintenance reaction 4.5 hours；Sampling, measures acid number for 0.19mgKOH/g, and esterification terminates.
2nd, dealcoholysis process
At 200 DEG C, normal pressure dealcoholysis is carried out 1.0 hours, then carry out the removed under reduced pressure 0.5 hour that vacuum is -0.085Mpa.Altogether
Removing alcohol excess and part Ester 832kg.
3rd, subtractive process
To being passed through nitrogen in reactor（N2）, the material that step 2 is obtained is cooled to 100 DEG C under nitrogen protection, add
The mass concentration of 120kg is 3.5% NaOH solution；Stirring 30 minutes, stands 40 minutes, separation water phase.It is same with 120kg again
The NaOH aqueous solution carry out secondary N-process, separation water phase.
Directly to steam is passed through in product, the purification of product is carried out.Control steam pressure for 0.70Mpa, temperature is 190
DEG C, after 4.5 hours, sampling measures acid number for 0.08mgKOH/g, flash-point（Opening agar diffusion method）It is 206 DEG C.
4th, absorption and pressure-filtering process
Material is cooled to 105 DEG C, 5Kg activated carbons are added, filtered after stirring.Collection filtrate is adipic acid two（2- propyl group heptan）
Ester product.Product 2870kg is obtained altogether.
After testing, product appearance is limpid, is the oily liquids without visible foreign.Color and luster（pt-Co):No. 20, density（20
℃）, 0.916g/cm3；Flash-point（Opening agar diffusion method）：207℃；Acid number：0.06mgKOH/g, purity（GC methods）It is 99.70%；Product
Yield is 98.35%.
Embodiment 3
A kind of adipic acid two（2- propyl group heptan）The preparation method of ester, comprises the following steps：
First, esterification reaction process：
To being passed through nitrogen in reactor（N2）, adipic acid and 2- propyl enanthols are pressed 1.0 under nitrogen protection:2.9 weight ratio,
During the 2- propyl enanthols of 3190kg are put into the reactor of 6m3, the adipic acid of 1100kg is put into again under agitation.Heat up.
When temperature is raised to 175 DEG C, maintain 1.5 hours, add stannous oxide catalyst 2.0kg, dibutyl tin
2.0kg, stannous oxalate 1.0kg.It is warmed up to 220 DEG C, maintenance reaction 4.0 hours；Sampling, measures acid number for 0.22mgKOH/g, ester
Change reaction to terminate.
2nd, dealcoholysis process
At 195 DEG C, normal pressure dealcoholysis is carried out 0.5 hour, then it is dealcoholysis 2 hours of being depressurized under -0.075Mpa to carry out vacuum.It is de- altogether
Except alcohol excess and part Ester 716kg.
3rd, subtractive process
To being passed through nitrogen in reactor（N2）, the material that step 2 is obtained is cooled to 105 DEG C under nitrogen protection, add
The mass concentration of 120kg is 3.5% NaOH solution；Stirring 30 minutes, stands 40 minutes, separation water phase.It is same with 120kg again
The NaOH aqueous solution carry out secondary N-process, separation water phase.
To steam is passed directly into product, the purification of product is carried out.Control steam pressure for 0.75Mpa, temperature is 175
DEG C, after 4 hours, sampling measures acid number for 0.09mgKOH/g, flash-point（Opening agar diffusion method）It is 204 DEG C.
4th, adsorption process
Material is cooled to 105 DEG C, 5Kg activated carbons are added, filtered after stirring.Collection filtrate is adipic acid two（2- propyl group heptan）
Ester product.Product 3163kg is obtained altogether.
After testing, product is the transparent oily liquids without visible foreign.Color and luster（pt-Co):No. 15, density（20℃）,
0.912g/cm³；Flash-point（Opening agar diffusion method）It is 204 DEG C；Acid number：0.08mgKOH/g, purity（GC methods）It is 99.71%；Product yield
It is 98.71%.
Comparative example 1
Comparative example preparation method uses method disclosed in patent application 200910040889.5, wherein adipic acid and 2- propyl enanthols
By 1.0:2.9 weight ratio, during the 2- propyl enanthols of 3190kg are put into the reactor of 6m3, puts into again under agitation
The adipic acid of 1100kg, catalyst uses butyl titanate, according to adipic acid, 0.2% preparation of 2- propyl enanthol gross masses, ester
It is 180 DEG C to change temperature, and the reaction time is 4h.
After testing, the color and luster of product（pt-Co):No. 25, density（20℃）, 0.925g/cm3；Acid number：0.15mgKOH/g,
Purity（GC methods）It is 92.71%；Product yield is 89.71%.
From the above mentioned knowable to embodiment, the adipic acid two prepared by method for fine finishing of the invention（2- propyl group heptan）Ester is compared
The adipic acid two of prior art synthesis（2- propyl group heptan）Ester, with purity is high, high income, the low advantage of density, acid number.
The preferred embodiment of the invention is these are only, creation is not intended to limit the invention, it is all in the present invention
Any modification, equivalent and improvement made within the spirit and principle of creation etc., should be included in the guarantor of the invention
Within the scope of shield.
Claims (10)
1. a kind of adipic acid two（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that comprise the following steps：
Step one：To being passed through nitrogen in reactor, and 2- propyl enanthols and adipic acid put into the reactor；It is warmed up to
150~180 DEG C, metal tin compound catalyst is added, carry out 2 ~ 3h of reaction；200~225 DEG C are warmed up to, when material in system
Acid number be less than or equal to 0.25mgKOH/g when, reaction terminates；
Step 2：Excessive 2- propyl enanthols in removing step one；
Step 3：To nitrogen is passed through in reactor, the product of step 2 is cooled to 95~105 DEG C, neutralized, then by steam pair
Product is purified；
Step 4：To porous sorbing material is added in the reactant of step 3, finished product is filtered in stirring.
2. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
2- propyl enanthols in step one：The mol ratio of adipic acid is 2.8 ~ 3.1:After 1.0,2- propyl enanthols, adipic acid are added, 150
After maintaining 1 ~ 2h at~180 DEG C, then add catalyst.
3. a kind of adipic acid two according to claim 2（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
2- propyl enanthols in step one：The mol ratio of adipic acid is 2.9:1.0.
4. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
Removing in step 2 includes two stages：First stage：At 185~200 DEG C, normal pressure dealcoholysis is carried out, the dealcoholysis time is
0.5~1.5h；Second stage：Opening vacuum carries out decompression dealcoholysis, vacuum is controlled for -0.075~-0.090Mpa, during dealcoholysis
Between be 0.5 ~ 2h.
5. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
Neutralized in step 3 and using the NaOH aqueous solution of 3.5%wt, after standing, separated the water phase after neutralizing；Steam pressure
It is 0.70~0.80Mpa, temperature is 175~190 DEG C, the time of purification is 3.5~4.5 hours.
6. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
The acid number that material is purified in step 3 reaches 0.1mgKOH/g or below 0.1mgKOH/g.
7. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
Porous sorbing material in step 4 is activated carbon.
8. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
Metallic tin chemical combination includes the combination of one or more among stannous oxide, stannous oxalate, Dibutyltin oxide.
9. a kind of adipic acid two according to claim 1（2- propyl group heptan）The method for fine finishing of ester, it is characterised in that described
The addition quality of catalyst is the 0.5% of the quality that feeds intake of adipic acid.
10. a kind of adipic acid two using as described in claim any one of 1-9（2- propyl group heptan）The method for fine finishing processing of ester
Adipic acid two（2- propyl group heptan）Ester, it is characterised in that：The adipic acid two（2- propyl group heptan）Colourity pt-co≤No. 20 of ester,
Density is 0.915 ± 0.005g/cm3, flash-point >=203 DEG C, purity >=99.60%；Acid number≤0.10mgKOH/g.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112724016A (en) * | 2020-12-31 | 2021-04-30 | 潍坊加易加生物科技有限公司 | Method for recycling esterification catalyst stannous oxide |
| CN113214079A (en) * | 2021-05-26 | 2021-08-06 | 浙江皇星化工股份有限公司 | Production method of DPHP |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101602666A (en) * | 2009-07-07 | 2009-12-16 | 佛山市顺德区天晟贸易有限公司 | Hexanodioic acid two (2-propyl group heptan) ester and its production and application |
| CN104284932A (en) * | 2012-08-23 | 2015-01-14 | Lg化学株式会社 | Plasticizer composition |
| CN104411674A (en) * | 2012-07-06 | 2015-03-11 | 巴斯夫欧洲公司 | The use of carboxylic acid esters as lubricants |
| CN104945607A (en) * | 2015-07-24 | 2015-09-30 | 山东万图高分子材料有限公司 | Environment-friendly polyester plasticizer as well as preparation method and application thereof |
-
2016
- 2016-12-16 CN CN201611164148.4A patent/CN106699554A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101602666A (en) * | 2009-07-07 | 2009-12-16 | 佛山市顺德区天晟贸易有限公司 | Hexanodioic acid two (2-propyl group heptan) ester and its production and application |
| CN104411674A (en) * | 2012-07-06 | 2015-03-11 | 巴斯夫欧洲公司 | The use of carboxylic acid esters as lubricants |
| CN104284932A (en) * | 2012-08-23 | 2015-01-14 | Lg化学株式会社 | Plasticizer composition |
| CN104945607A (en) * | 2015-07-24 | 2015-09-30 | 山东万图高分子材料有限公司 | Environment-friendly polyester plasticizer as well as preparation method and application thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112724016A (en) * | 2020-12-31 | 2021-04-30 | 潍坊加易加生物科技有限公司 | Method for recycling esterification catalyst stannous oxide |
| CN113214079A (en) * | 2021-05-26 | 2021-08-06 | 浙江皇星化工股份有限公司 | Production method of DPHP |
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Application publication date: 20170524 |