CN112876358A - Method for preparing isooctyl acetate - Google Patents
Method for preparing isooctyl acetate Download PDFInfo
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- CN112876358A CN112876358A CN202110147378.4A CN202110147378A CN112876358A CN 112876358 A CN112876358 A CN 112876358A CN 202110147378 A CN202110147378 A CN 202110147378A CN 112876358 A CN112876358 A CN 112876358A
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- DICUPLXUNISGAQ-UHFFFAOYSA-N Isooctyl acetate Chemical compound CC(C)CCCCCOC(C)=O DICUPLXUNISGAQ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 89
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 75
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229920001429 chelating resin Polymers 0.000 claims abstract description 37
- 239000002245 particle Substances 0.000 claims abstract description 37
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 238000005886 esterification reaction Methods 0.000 claims abstract description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 17
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000003729 cation exchange resin Substances 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 4
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 229940011051 isopropyl acetate Drugs 0.000 claims description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
- 229920000557 Nafion® Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- -1 isooctyl ester Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing isooctyl acetate, and relates to the technical field of chemical synthesis. The preparation method comprises the following steps: acetic acid and isooctyl alcohol are used as raw materials, and esterification reaction is carried out in the presence of a catalyst and a water-carrying agent to obtain isooctyl acetate; in the implementation process of the invention, the mass ratio of D72 to Amberlite IR-120 is controlled to be 1:2-5, and the particle size of the D72 catalyst is 0.85-1.20 mm; the Amberlite IR-120 catalyst has the particle size of 0.75-0.85mm and the volume ratio of cyclohexane to carbon tetrachloride of 5-10:1, and the yield and purity of isooctyl acetate are obviously improved by controlling the types of the catalyst and the water-carrying agent and the particle size of the catalyst.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a method for preparing isooctyl acetate.
Background
The isooctyl acetate is a colorless transparent liquid, is insoluble in water, is dissolved in organic solvents such as ethanol and acetone, and has strong permeability and good adhesive force. Isooctyl acetate is an important chemical raw material, is used as a water-insoluble high-boiling point solvent, is widely applied to the industries of organic synthesis, coatings, plastics, spices, adhesives, leather and the like, can also be used as a good solvent in the synthesis process of nitrocellulose and a plurality of natural resins, and can also be used in the application of coating brushing, dip coating, spray coating and paint baking. The isooctyl acetate is added into the paint for the main purpose of improving the flow and the film forming effect, and can also be used as a good coalescing aid for emulsion paint, and is an additive of a cleaning agent and a paint remover. In the traditional process, acetic acid and isooctyl alcohol are mainly used as raw materials, sulfuric acid is used as a catalyst to directly catalyze and esterify, but the sulfuric acid is used as the catalyst to have the defects of serious equipment corrosion, more side reactions, complex post-treatment process, serious environmental pollution and the like. In recent years, efforts have been made to develop green catalysts for esterification reactions to overcome the disadvantages of sulfuric acid catalysts; in the prior literature, Amerlyst15 strong-acid cation exchange resin is used as a catalyst, the reaction process of synthesizing isooctyl acetate by the esterification of acetic acid and isooctyl ester in a reaction kettle is researched, the influence of the stirring speed, the particle size of the catalyst, the reaction temperature, the catalyst dosage and the molar ratio of acid and alcohol on the esterification reaction rate is considered, and Amerlyst15 strong-acid cation exchange resin is used as a catalyst, toluene is used as an entrainer, and the isooctyl acetate is prepared by directly esterifying the acetic acid and isooctyl alcohol.
Researches show that the cation exchange resin has the advantages of good catalytic activity and selectivity, higher chemical stability, no corrosion to equipment, no pollution, easy separation, regeneration and reutilization and the like in the esterification reaction, and the defects of the traditional esterification catalyst are overcome.
However, the cation exchange resin catalysts which are applied to esterification reaction are Amerlyst15 strong acid cation exchange resin and NKC-9 strong acid cation exchange resin.
For example, Liu Yong et al studied the reaction process of esterifying acetic acid and isooctyl alcohol to synthesize isooctyl acetate in an intermittent stirred tank reactor by using Amerlyst15 strong-acid cation exchange resin as a catalyst. The influence of the stirring speed, the catalyst particle size, the reaction temperature, the catalyst dosage and the acid-alcohol molar ratio on the esterification reaction rate is investigated; intrinsic reaction kinetics experiments were performed under conditions that eliminate the effect of internal and external diffusion. In the range of 343.15-363.15K, experimental data are correlated by using a pseudo-homogeneous kinetic model, index pre-factors of forward and reverse reaction rate constants are 5061 and 12.78L/(mol.g.min), and activation energies of forward and reverse reactions are 54.43 and 37.68kJ/mol respectively (kinetics of isooctyl acetate synthesized by catalysis of strong-acid cation exchange resin, Liuyong et al, petrochemical industry, 42 vol. 6 of 2013).
For example, isooctyl acetate is synthesized by using NKC-9 strong-acid cation exchange resin as a catalyst in the research of Ilna, and the product is qualitatively and quantitatively researched (synthesis of isooctyl acetate by ester exchange, Ilna, Shuoshi paper, university of Dalian industries, 2014).
However, according to the research of the prior art, the yield of isooctyl acetate prepared by esterification reaction using amberlyst 15 and NKC-9 strong acid cation exchange resin as catalysts can reach about 90%, the purity is about 97%, the requirement cannot be met better, and the addition amount of the NKC-9 strong acid cation exchange resin catalyst disclosed in the prior art is 20%, because the catalyst is a resin which can adsorb the product, the yield of the final product is influenced.
Therefore, it is required to develop a preparation method capable of improving the yield and purity of isooctyl acetate.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for preparing isooctyl acetate, which takes acetic acid and isooctyl alcohol as raw materials, takes the same cation exchange resin as a catalyst, and takes a mixture solvent as a water-carrying base, so that the conversion rate of the acetic acid in the reaction process can be obviously improved, and the purity and the yield of the obtained isooctyl acetate are obviously improved.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention discloses a method for preparing isooctyl acetate, which uses acetic acid and isooctyl alcohol as raw materials to carry out esterification reaction in the presence of a catalyst and a water-carrying agent to obtain the isooctyl acetate.
Wherein the catalyst is cation exchange resin catalyst, and the cation exchange resin catalyst is selected from one or more of EX 146H, D61, D72, Amberlyst-15, NKC-9, Nafion 511 and Amberlite IR-120;
preferably, the cation exchange resin catalyst is selected from one or more of D61, D72, Amberlyst-15, NKC-9 or Amberlite IR-120;
still preferably, the cation exchange resin catalyst is selected from one or more of D61, D72 or Amberlite IR-120;
further preferably, the cation exchange resin catalyst is a mixture of D72 and Amberlite IR-120.
The mass ratio of D72 to Amberlite IR-120 is 1: 2-5;
preferably, the mass ratio of D72 to Amberlite IR-120 is 1: 3-4;
still more preferably, the mass ratio of D72 to Amberlite IR-120 is 1: 3.
The water-carrying agent is one or more of benzene, toluene, cyclohexane, n-propyl acetate, isopropyl acetate, chloroform and carbon tetrachloride;
preferably, the water-carrying agent is one or more of toluene, cyclohexane, n-propyl acetate, isopropyl acetate, chloroform and carbon tetrachloride;
preferably, the water-carrying agent is one or more of cyclohexane, n-propyl acetate, isopropyl acetate, chloroform and carbon tetrachloride;
further preferably, the water-carrying agent is a mixture of cyclohexane and carbon tetrachloride; the volume ratio of cyclohexane to carbon tetrachloride is 5-10: 1; the volume ratio of cyclohexane to carbon tetrachloride is 5:1, 6: 1. 7: 1. 8: 1. 9: 1 or 10: 1; preferably 10: 1.
The particle size of the catalyst is 0.75-1.20 mm; the particle size of the catalyst is 0.75mm, 0.80mm, 0.85mm, 0.90mm, 1.0mm, 1.1mm and 1.2 mm.
In the implementation process, the invention unexpectedly discovers that the catalyst with different particle sizes can be used for promoting the conversion rate of isooctyl alcohol;
in some preferred embodiments, the D72 catalyst has a particle size of 0.85 to 1.20 mm; the particle size of the Amberlite IR-120 catalyst is 0.75-0.85 mm;
preferably, the particle size of the D72 catalyst is 1.0-1.20 mm; the particle size of the Amberlite IR-120 catalyst is 0.80-0.85 mm;
more preferably, the particle size of the D72 catalyst is 1.0 mm; the particle size of the Amberlite IR-120 catalyst is 0.8 mm.
The molar ratio of the acetic acid to the isooctyl alcohol is 1: 1-2; preferably, the molar ratio of acetic acid to isooctanol is 1:1.2 to 1.8; still more preferably, the molar ratio of acetic acid to isooctanol is 1: 1.5.
The mass ratio of the catalyst to the acetic acid is 2-5: 100; preferably 3 to 5:100, respectively; still more preferably 4: 100.
The mass ratio of the acetic acid to the water-carrying agent is 100: 1.5-3; preferably 100: 2.0 to 3; more preferably 100: 2.5.
the reaction temperature of the esterification reaction is 80-95 ℃; preferably, the reaction temperature is 85-95 ℃; more preferably, the reaction temperature is 90-95 ℃; further preferably, the reaction temperature is 95 ℃.
And purifying the product to obtain the finished product of isooctyl acetate.
Compared with the prior art, the invention has the beneficial effects that:
(1) the invention uses cation exchange resin as catalyst, which can obviously improve the conversion rate of acetic acid, and the invention unexpectedly discovers that the mixed catalyst can accelerate the reaction rate, the catalyst used in the invention is the mixture of D72 and Amberlite IR-120, and the mass ratio of the D72 to the Amberlite IR-120 is controlled to be 1:2-5, which can obviously improve the purity of the product;
(2) according to the invention, the particle size of the catalyst is researched, and the discovery that the two catalysts with different particle sizes are used simultaneously can effectively weaken the internal diffusion of reactants in the cation exchange resin catalyst in the reaction process and improve the reaction efficiency; the use amount of the catalyst can be reduced, and the product waste caused by adsorption is reduced;
(3) in the implementation process, the mixture of two solvents is used as a water-carrying agent, and the esterification reaction is better carried out in the positive direction by controlling the volume ratio of the two solvents, so that the yield of the product is improved.
(4) By selecting the catalyst and the water-carrying agent, the invention obviously improves the reaction efficiency, reduces the reaction temperature and ensures that the yield and the purity of the obtained isooctyl acetate are higher than those of the prior art.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The source of the reagent used in the present invention is not limited, and the reagents used in the present invention are all commercially available products in the art, and all the reagents used are AR, unless otherwise specified.
Example 1 preparation method of isooctyl acetate
30g of acetic acid (0.5mol), 65g of isooctanol (0.5mol), 0.6g of catalyst and 450mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 10 hours at 80 ℃, and after the reaction is finished, reduced pressure distillation is carried out to obtain the isooctyl acetate.
The catalyst comprises D72 and Amberlite IR-120 in a mass ratio of 1:2, and the particle size of the D72 catalyst is 0.85 mm; the particle size of the Amberlite IR-120 catalyst is 0.75 mm;
the water-carrying agent is cyclohexane and carbon tetrachloride in a volume ratio of 5: 1.
Example 2 preparation method of isooctyl acetate
30g of acetic acid (0.5mol), 130g of isooctanol (1mol), 1.5g of catalyst and 900mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 95 ℃, and after the reaction is finished, reduced pressure distillation is carried out to obtain the isooctyl acetate.
The catalyst comprises D72 and Amberlite IR-120 in a mass ratio of 1:5, and the particle size of the D72 catalyst is 1.20 mm; the particle size of the Amberlite IR-120 catalyst is 0.85 mm;
the water-carrying agent is cyclohexane and carbon tetrachloride in a volume ratio of 10: 1.
Example 3 preparation method of isooctyl acetate
30g of acetic acid (0.5mol), 97.5g of isooctanol (0.75mol), 1.2g of catalyst and 750mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 90 ℃, and after the reaction is finished, reduced pressure distillation is carried out to obtain the isooctyl acetate.
The catalyst comprises D72 and Amberlite IR-120 in a mass ratio of 1:3, and the particle size of the D72 catalyst is 1.0 mm; the particle size of the Amberlite IR-120 catalyst is 0.8 mm;
the water-carrying agent is cyclohexane and carbon tetrachloride in a volume ratio of 10: 1.
Example 4
30g of acetic acid (0.5mol), 97.5g of isooctanol (0.75mol), 1.2g of catalyst and 750mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 90 ℃, and after the reaction is finished, reduced pressure distillation is carried out to obtain the isooctyl acetate.
The catalyst is D72, and the particle size of the D72 catalyst is 0.8 mm;
the water-carrying agent is cyclohexane and carbon tetrachloride in a volume ratio of 10: 1.
Example 5
30g of acetic acid (0.5mol), 97.5g of isooctanol (0.75mol), 1.2g of catalyst and 750mg of water-carrying agent are uniformly mixed, esterification reaction is carried out for 12 hours at 90 ℃, and after the reaction is finished, reduced pressure distillation is carried out to obtain the isooctyl acetate.
The catalyst is Amberlite IR-120, and the particle size of the Amberlite IR-120 catalyst is 1.0 mm;
the water-carrying agent is carbon tetrachloride.
Comparative example 1
The difference from example 3 is that: the catalysts were D72 and Amberlite IR-120 in a mass ratio of 1:1, and the other operations and steps were the same as in example 3.
Comparative example 2
The difference from example 3 is that: the catalysts were D72 and Amberlite IR-120 in a mass ratio of 1:7, and the other operations and steps were the same as in example 3.
Comparative example 3
The difference from example 3 is that: catalyst D72 and Amberlite IR-120 both had a particle size of 0.85mm, and the other operations and procedures were the same as in example 3.
Comparative example 4
The difference from example 3 is that: the water-carrying agent is a mixture of cyclohexane and carbon tetrachloride in a volume ratio of 3:1, and other operations and steps are the same as those in example 3.
Comparative example 5
The difference from example 3 is that: the operation and the steps of the water-carrying agent cyclohexane are the same as those of the embodiment 3.
Test example 1 yield and purity of isooctyl acetate product
The yield and purity of the obtained isooctyl acetate product are shown in table 1 below.
The yield was ═ (actual yield ÷ theoretical yield) × 100%
Purity ═ purity (content of isooctyl acetate in product ÷ actual yield) × 100%
TABLE 1
| Purity of％ | Yield% | |
| Example 1 | 98.5 | 95.3 |
| Example 2 | 98.8 | 95.0 |
| Example 3 | 99.8 | 97.8 |
| Example 4 | 95.8 | 92.2 |
| Example 5 | 96.0 | 91.4 |
| Comparative example 1 | 96.5 | 91.8 |
| Comparative example 2 | 97.0 | 92.0 |
| Comparative example 3 | 97.5 | 92.6 |
| Comparative example 4 | 96.8 | 92.8 |
| Comparative example 5 | 96.2 | 92.1 |
According to the detection data in the table 1, the yield and purity of isooctyl acetate obtained by the preparation method of isooctyl acetate provided by the invention are higher, the yield and purity of isooctyl acetate are obviously improved by controlling the catalysts to be D72 and Amberlite IR-120 with the mass ratio of 1:2-5, the water-carrying agent to be cyclohexane and carbon tetrachloride with the volume ratio of 5-10:1 and controlling the particle size of the catalysts to obviously improve the conversion rate of acetic acid, especially D72 and Amberlite IR-120 with the mass ratio of 1:3 in the embodiment 3, and the particle size of the D72 catalyst is 1.0 mm; the particle size of the Amberlite IR-120 catalyst is 0.8 mm; and the volume ratio of cyclohexane to carbon tetrachloride is 10:1, the yield of the finally obtained isooctyl acetate is 97.8%, the purity is 99.8%, and the yield and the purity of the isooctyl acetate are obviously reduced by changing the type, the mass ratio or the particle size of the catalyst.
Test example 2 detection of Water content and acidity in isooctyl acetate
The detection method is a method conventional in the art.
In order to further illustrate the relatively high purity of isooctyl acetate prepared by the present invention, the impurities, moisture and acidity obtained in the product were examined and the results are shown in table 2 below.
TABLE 2
| Water content% | Acidity% | |
| Example 1 | 0.08 | 0.02 |
| Example 2 | 0.08 | 0.02 |
| Example 3 | 0.05 | 0.01 |
| Example 4 | 0.09 | 0.03 |
| Example 5 | 0.10 | 0.03 |
| Comparative example 1 | 0.09 | 0.04 |
| Comparative example 2 | 0.09 | 0.04 |
| Comparative example 3 | 0.09 | 0.03 |
| Comparative example 4 | 0.09 | 0.03 |
| Comparative example 5 | 0.10 | 0.03 |
According to the detection data in the table 2, the purity of isooctyl acetate obtained by the preparation method of isooctyl acetate provided by the invention is higher, the conversion rate of acetic acid can be obviously improved by controlling the catalysts to be D72 and Amberlite IR-120 in a mass ratio of 1:2-5, the water carrying agent is controlled to be cyclohexane and carbon tetrachloride in a volume ratio of 5-10:1, water can be effectively carried out, the conversion rate of acetic acid is further improved, the water content and acidity in the obtained product are lower, particularly, the D72 and Amberlite IR-120 in a mass ratio of 1:3 in the embodiment 3 are controlled, and the particle size of the D72 catalyst is 1.0 mm; the particle size of the Amberlite IR-120 catalyst is 0.8 mm; and the volume ratio of cyclohexane to carbon tetrachloride is 10:1, the finally obtained isooctyl acetate has the lowest moisture and acidity values, so that the purity of the isooctyl acetate obtained in example 3 is the highest; when the type, the mass ratio or the particle size of the catalyst and the volume ratio of the components in the water-carrying agent are not in the range claimed by the invention, the water content and the acidity of the isooctyl acetate product are obviously improved.
The present invention has been further described with reference to specific embodiments, which are only exemplary and do not limit the scope of the present invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (10)
1. A method for preparing isooctyl acetate, use acetic acid and isooctyl alcohol as raw materials, take place esterification reaction under the existence of catalyst and water-carrying agent, get isooctyl acetate, characterized by that: the catalyst is cation exchange resin catalyst, and the cation exchange resin catalyst is selected from one or more of EX 146H, D61, D72, Amberlyst-15, NKC-9, Nafion 511 and Amberlite IR-120.
2. The method of claim 1, wherein: the cation exchange resin catalyst is a mixture of D72 and Amberlite IR-120; the mass ratio of the D72 to the Amberlite IR-120 is 1: 2-5.
3. The method of claim 2, wherein: the mass ratio of D72 to Amberlite IR-120 was 1: 3.
4. The method of claim 1, wherein: the water-carrying agent is one or more of benzene, toluene, cyclohexane, chloroform, n-propyl acetate, isopropyl acetate and carbon tetrachloride.
5. The method of claim 4, wherein: the water-carrying agent is a mixture of cyclohexane and carbon tetrachloride; the volume ratio of cyclohexane to carbon tetrachloride is 5-10: 1.
6. The method of claim 5, wherein: the volume ratio of cyclohexane to carbon tetrachloride is 10: 1.
7. The method of claim 1, wherein: the particle size of the catalyst is 0.75-1.20 mm.
8. The method of claim 7, wherein: the particle size of the D72 catalyst is 0.85-1.20 mm; the particle size of the Amberlite IR-120 catalyst is 0.75-0.85 mm.
9. The method of claim 8, wherein: the particle size of the D72 catalyst is 1.0 mm; the particle size of the Amberlite IR-120 catalyst is 0.8 mm.
10. The method of claim 1, wherein: the mass ratio of the catalyst to the acetic acid is 2-5: 100; the mass ratio of the acetic acid to the water-carrying agent is 100: 1.5-3.
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| 徐红等: "反应精馏制备醋酸异辛酯新工艺的模拟研究", 《现代化工》 * |
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Application publication date: 20210601 |