CN114014870A - Preparation method of isosorbide ester bio-based plasticizer, product and application thereof - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- 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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
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- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Abstract
The invention discloses a preparation method of an isosorbide ester bio-based plasticizer, and a product and application thereof, and belongs to the technical field of plastic processing aids. The preparation method of the isosorbide ester bio-based plasticizer comprises the following steps: isosorbide and monocarboxylic acid are used as raw materials, esterification reaction is carried out under the action of a catalyst to obtain isosorbide ester, and then oxidation reaction is carried out by using the isosorbide ester as the raw material to obtain epoxy isosorbide ester. The isosorbide ester and epoxy isosorbide ester bio-based plasticizer prepared by the invention can be applied to the preparation of PVC composite materials, can replace part of the traditional o-benzene plasticizers, and the prepared PVC composite materials have excellent mechanical properties and processability. In addition, the ionic liquid is selected as the catalyst for the esterification reaction, the ionic liquid and the esterification product can be subjected to self-phase separation after the reaction is finished, the catalyst can be recycled and post-treated at the same time, no waste liquid is generated, and the method is simple, convenient and environment-friendly.
Description
Technical Field
The invention relates to the technical field of plastic processing aids, in particular to a preparation method of an isosorbide ester bio-based plasticizer, and a product and application thereof.
Background
PVC is one of the most commonly used traditional plastics, has poor processing flowability and thermal stability, and PVC materials are decomposed to generate hydrogen chloride at the temperature of more than 100 ℃ or after being irradiated by sunlight for a long time, and the decomposition speed becomes faster under the catalysis of the hydrogen chloride, so that a stabilizer and a plasticizer must be added in the actual processing production to improve the stability and the processing flowability of the PVC. There are many types of plasticizers used to plasticize PVC, with the phthalate esters accounting for approximately 80% of the total usage. In recent years, the influence of o-benzene plasticizers on human bodies and the environment is receiving more and more attention, and researches show that the migrating o-benzene plasticizers cause serious harm to the health of the human bodies and the social environment.
Therefore, the synthesis of a novel ester plasticizer taking a bio-base as a raw material to replace part of the traditional o-benzene plasticizer becomes a research hotspot in the field. The esterification reaction usually adopts strong acid as a catalyst, such as concentrated sulfuric acid, p-toluenesulfonic acid and the like, after the reaction is finished, the p-toluenesulfonic acid, the sulfuric acid and the like can be mutually dissolved with an esterification product, the strong acid in the product can be completely removed only by multi-step washing and separation in the product purification process, the post-treatment process is complex and tedious, and a lot of acidic waste liquid can be generated, so that the method is not environment-friendly. How to prepare a novel ester plasticizer and optimize the preparation method becomes a technical problem to be solved urgently by the technical personnel in the field.
Disclosure of Invention
The invention aims to provide a preparation method of an isosorbide ester bio-based plasticizer, a product and an application thereof, aiming at solving the problems in the prior art, isosorbide ester is prepared by taking isosorbide, monocarboxylic acid and a catalyst as raw materials, and an oxidation reaction is carried out to obtain epoxy isosorbide ester, so that the bio-based plasticizer with excellent performance is prepared.
In order to achieve the purpose, the invention provides the following scheme:
one of the technical schemes of the invention is as follows: a method for preparing isosorbide ester bio-based plasticizer comprises the following steps: the isosorbide ester is obtained by taking isosorbide and monocarboxylic acid as raw materials and carrying out esterification reaction under the action of a catalyst.
Further, the monocarboxylic acid includes any one of oleic acid, ricinoleic acid, or myristic acid.
Further, the catalyst is 1-propyl sulfonic acid-3-methyl imidazole bisulfate.
Further, the molar ratio of the isosorbide to the monocarboxylic acid to the catalyst is 0.5-2: 2-4: 0.05 to 1.
Further, the preparation method of the isosorbide ester bio-based plasticizer further comprises the steps of taking the isosorbide ester as a raw material, adding hydrogen peroxide, acetic acid and a catalyst for oxidation reaction to obtain epoxy isosorbide ester; the catalyst is concentrated sulfuric acid.
Further, the molar ratio of the isosorbide ester to the hydrogen peroxide to the acetic acid to the catalyst is 0.5-2: 15-25: 2-4: 0.01 to 0.05.
The second technical scheme of the invention is as follows: the isosorbide ester bio-based plasticizer prepared by the preparation method of the isosorbide ester bio-based plasticizer.
The third technical scheme of the invention is as follows: the application of the isosorbide ester bio-based plasticizer in preparing a PVC composite material.
Further, the preparation of the PVC composite material comprises the following steps: uniformly mixing the isosorbide ester bio-based plasticizer, the epoxidized soybean oil and the PVC, banburying, stirring at room temperature for 15min, then heating to 175 ℃, and continuing to stir for 10min to obtain the PVC composite material.
Further, the mass ratio of the epoxy isosorbide ester bio-based plasticizer to the epoxidized soybean oil to the PVC is 5-10: 10-30: 100.
further, the structural formula of the 1-propylsulfonic acid-3-methylimidazole bisulfate is shown as the formula (1):
the invention discloses the following technical effects:
(1) the isosorbide ester and epoxy isosorbide ester bio-based plasticizer prepared by the invention is compounded with the epoxy soybean oil and added into PVC, and can replace part of the traditional o-benzene plasticizers, so that the prepared PVC composite material has excellent mechanical property and processability.
(2) The method adopts the 1-propylsulfonic acid-3-methylimidazole bisulfate ionic liquid as the catalyst, can simplify the preparation process of the isosorbide ester, can be automatically separated from the esterification product after the reaction is finished, can simultaneously realize the recycling and post-treatment of the catalyst, is environment-friendly and does not generate waste liquid;
(3) compared with the traditional method of plastifying PVC by adopting an open mixing method, the internal mixing method adopted by the invention can effectively shorten the mixing time and better overcome the dust flying in the mixing process.
(4) The raw materials adopted by the invention are all from plants, and are green, environment-friendly and healthy.
(5) According to the invention, 1-propylsulfonic acid-3-methylimidazole hydrogen sulfate ionic liquid is used as a catalyst, isosorbide ester is prepared on the premise of omitting concentrated sulfuric acid, and epoxy isosorbide ester can be prepared by further taking isosorbide ester as a raw material and only dropwise adding a very small amount of concentrated sulfuric acid, so that excessive waste liquid is not generated in the treatment process, and the method is environment-friendly and efficient.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without creative efforts.
FIG. 1 is an infrared spectrum of isosorbide oleate and isosorbide epoxy oleate prepared by the present invention;
FIG. 2 is an infrared spectrum of isosorbide ricinoleate and isosorbide epoxy ricinoleate prepared according to the present invention;
FIG. 3 is an infrared spectrum of isosorbide myristate prepared according to the present invention;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of isosorbide oleate and isosorbide epoxy oleate prepared by the invention;
FIG. 5 is the nuclear magnetic resonance hydrogen spectrum of the isosorbide ricinoleate and the isosorbide epoxy ricinoleate prepared by the invention;
FIG. 6 is the NMR spectrum of isosorbide myristate prepared by the invention.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but as a more detailed description of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Further, for numerical ranges in this disclosure, it is understood that each intervening value, between the upper and lower limit of that range, is also specifically disclosed. Every smaller range between any stated value or intervening value in a stated range and any other stated or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
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. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference herein for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The specification and examples are exemplary only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are open-ended terms that mean including, but not limited to.
The "parts" described in the following examples are all "parts by mass".
The synthetic routes for isosorbide esters and epoxy isosorbide esters are shown below:
example 1
Adding a mixture of 1: 2.1: 0.07 of isosorbide, oleic acid and 1-propylsulfonic acid-3-methylimidazole bisulfate, then 60mL of toluene is added, the mixture is stirred and reacted for 5 hours at the temperature of 120 ℃, the temperature is raised to 150 ℃ and the reaction is carried out for 1 hour, after the reaction is finished, the ionic liquid (1-propylsulfonic acid-3-methylimidazole bisulfate) and the esterification product are layered, and the isosorbide oleate (OA-ISB) is obtained after separation, wherein the yield is 85 percent.
Example 2
Adding a mixture of 1: 2.1: 0.07 of isosorbide, ricinoleic acid and 1-propylsulfonic acid-3-methylimidazole bisulfate, then 60mL of toluene is added, the mixture is stirred and reacted for 5 hours at the temperature of 120 ℃, then the temperature is raised to 150 ℃ for reaction for 1 hour, after the reaction is finished, the ionic liquid and the esterification product are layered, and the ricinoleic acid isosorbide ester (RA-ISB) is obtained after separation, wherein the yield is 88%.
Example 3
Adding a mixture of 1: 2.1: 0.07 of isosorbide, myristic acid and 1-propylsulfonic acid-3-methylimidazole bisulfate, then 60mL of toluene is added, the mixture is stirred and reacted for 5 hours at the temperature of 120 ℃, the temperature is raised to 150 ℃ and the mixture is reacted for 1 hour, after the reaction is finished, the ionic liquid and the esterification product are layered, and the isosorbide myristate (MA-ISB) is obtained after separation, wherein the yield is 90%.
Example 4
Adding a mixture of 1: 20: 3: isosorbide oleate (OA-ISB), hydrogen peroxide, acetic acid and concentrated sulfuric acid of 0.01 are stirred and reacted for 5 hours at 65 ℃ to obtain epoxy isosorbide oleate (EOA-ISB) with the yield of 95%.
Example 5
Adding a mixture of 1: 20: 3: 0.01 percent of ricinoleic acid isosorbide ester (RA-ISB), hydrogen peroxide, acetic acid and concentrated sulfuric acid are stirred and reacted for 5 hours at 65 ℃ to obtain epoxy oleic acid isosorbide ester (ERA-ISB), and the yield is 85 percent.
The infrared spectrum of OA-ISB, RA-ISB, MA-ISB, EOA-ISB and ERA-ISB prepared in examples 1 to 5 is shown in figures 1 to 3, and the hydrogen spectrum of nuclear magnetic resonance is shown in figures 4 to 6.
Preparing a PVC composite material:
adding the raw materials into an internal mixer according to the raw material ratio of Table 1, stirring for 15min at room temperature, then heating to 175 ℃, continuing stirring for 10min, opening the internal mixer and taking out the materials to obtain the PVC composite material; and (3) pressing the PVC composite film at 170 ℃ by using a press machine, and testing the subsequent mechanical properties.
The following examples or comparative examples used MA-ISB prepared for example 3, EOA-ISB prepared for example 4, and ERA-ISB prepared for example 5.
TABLE 1
The elongation at break and tensile strength of the PVC composite films prepared in examples 6-10 and comparative examples 1-3 were measured according to the measurement of tensile properties of GB/T1040.3 plastics, and the results are shown in Table 2.
TABLE 2 mechanical Properties of PVC composite films
| Examples | Name of sample prepared | Elongation at Break (%) | Tensile Strength (MPa) |
| Example 6 | PVC/20ESO/5MA-ISB | 126.95±13.94 | 20.3±1.24 |
| Example 7 | PVC/20ESO/5EOA-ISB | 352.08±3.25 | 30.12±0.77 |
| Example 8 | PVC/20ESO/10EOA-ISB | 367.32±12.63 | 25.37±0.68 |
| Example 9 | PVC/10ESO/10EOA-ISB | 156.48±34.59 | 40.11±2.03 |
| Example 10 | PVC/10ESO/5ERA-ISB | 44.73±8.51 | 43.43±2.18 |
| Comparative example 1 | PVC/10ESO | / | / |
| Comparative example 2 | PVC/20ESO | 199.21±47.02 | 36.75±2.14 |
| Comparative example 3 | PVC/25ESO | 223±11.38 | 28.32±1.15 |
As can be seen from Table 2, the isosorbide ester or epoxy isosorbide ester bio-based plasticizer prepared by the invention and epoxidized soybean oil are compounded and added into PVC, so that the mechanical property and the processing property are excellent. When only 10 parts of epoxidized soybean oil (comparative example 1) is added, the PVC composite film cannot be obtained by an internal mixing method, but when 10 parts of epoxidized soybean oil and 5-10 parts of epoxy isosorbide ester compound plasticizer are added, the PVC composite film with the tensile strength of 40-43 MPa and the elongation at break of 44-156% can be prepared, and the prepared film has the characteristics of high strength and good toughness.
When only 20 parts of epoxidized soybean oil (comparative example 2) was added, the resulting PVC composite film had a tensile strength of 36MPa and an elongation at break of 199%. However, after 20 parts of epoxidized soybean oil and 5-10 parts of epoxy oleic acid isosorbide ester are added to compound the plasticizer, the PVC composite film with the tensile strength of 30-25 MPa and the elongation at break of 352-367 percent can be prepared. When only 25 parts of epoxidized soybean oil (comparative example 3) is added, the tensile strength of the prepared PVC composite membrane is 28MPa, and the elongation at break is 223%; compared with the composite film prepared by adding 20 parts of epoxidized soybean oil and 5 parts of epoxidized isosorbide oleate into the composite film, the PVC composite film (example 7) with the tensile strength of 30MPa and the elongation at break of 352% can be prepared, and compared with the composite film prepared by adding 25 parts of pure epoxidized soybean oil, the plasticizing effect of the composite film prepared by compounding the same parts of epoxidized soybean oil and epoxidized isosorbide is obviously better than that of the composite film prepared by adding 25 parts of pure epoxidized soybean oil.
When 20 parts of epoxidized soybean oil and 5 parts of isosorbide myristate compounded plasticizer were added, the tensile strength and elongation at break of the composite film were both reduced compared to those of comparative example 2 (example 6), mainly due to the fact that isosorbide myristate has no epoxy functional group in its structure and is poor in compatibility with epoxidized soybean oil, resulting in poor plasticizing effect on PVC after compounding.
When the epoxidized soybean oil accounts for 20 parts and the epoxy isosorbide oleate accounts for 10 parts, the PVC composite material prepared by compounding the plasticizer has the most excellent mechanical property. Due to the similar compatibility principle, the compatibility of epoxy isosorbide esters (EOA-ISB and ERA-ISB) and epoxidized soybean oil is better, and the migration resistance performance in the composite material is also better than that of the isosorbide ester prepared in the first step.
Example 11
The same as example 1, except that the molar ratio of isosorbide, oleic acid and 1-propylsulfonic acid-3-methylimidazolium hydrogen sulfate was 1: 2.1: 0.05. isosorbide oleate (OA-ISB) was obtained in a yield of 70%, resulting in a decrease in yield due to a decrease in the amount of the catalyst.
Example 12
The same as example 1, except that the molar ratio of isosorbide, oleic acid and 1-propylsulfonic acid-3-methylimidazolium hydrogen sulfate was 2: 4: 1. isosorbide oleate (OA-ISB) was obtained in 87% yield.
The above-described embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solutions of the present invention can be made by those skilled in the art without departing from the spirit of the present invention, and the technical solutions of the present invention are within the scope of the present invention defined by the claims.
Claims (10)
1. The preparation method of the isosorbide ester bio-based plasticizer is characterized by comprising the following steps: the isosorbide ester is obtained by taking isosorbide and monocarboxylic acid as raw materials and carrying out esterification reaction under the action of a catalyst.
2. The method for preparing an isosorbide ester bio-based plasticizer according to claim 1, wherein the monocarboxylic acid comprises any one of oleic acid, ricinoleic acid or myristic acid.
3. The method of preparing an isosorbide ester biobased plasticizer according to claim 1, wherein the catalyst is 1-propylsulfonic acid-3-methylimidazolium hydrogen sulfate.
4. The method for preparing isosorbide ester bio-based plasticizer according to claim 1, wherein the molar ratio of isosorbide, monocarboxylic acid and catalyst is 0.5 to 2: 2-4: 0.05 to 1.
5. The method for preparing isosorbide ester bio-based plasticizer according to claim 1, further comprising adding hydrogen peroxide, acetic acid and a catalyst to the isosorbide ester as a raw material to perform an oxidation reaction to obtain epoxy isosorbide ester; the catalyst is concentrated sulfuric acid.
6. The method for preparing the isosorbide ester bio-based plasticizer according to claim 5, wherein the molar ratio of isosorbide ester, hydrogen peroxide, acetic acid and catalyst is 0.5-2: 15-25: 2-4: 0.01 to 0.05.
7. An isosorbide ester bio-based plasticizer prepared according to the method for preparing an isosorbide ester bio-based plasticizer in any one of claims 1 to 6.
8. Use of an isosorbide ester bio-based plasticizer according to claim 7 in the preparation of a PVC composite.
9. Use according to claim 8, characterized in that the preparation of the PVC composite comprises the following steps: uniformly mixing the isosorbide ester bio-based plasticizer, the epoxidized soybean oil and the PVC, banburying, stirring at room temperature for 15min, then heating to 175 ℃, and continuing to stir for 10min to obtain the PVC composite material.
10. The use according to claim 9, wherein the mass ratio of the epoxy isosorbide ester bio-based plasticizer to the epoxy soybean oil to the PVC is 5-10: 10-30: 100.
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| CN114539619A (en) * | 2022-03-03 | 2022-05-27 | 昕亮科技（深圳）有限公司 | Preparation method of bio-based environment-friendly plasticizer for polyethylene resin |
| CN114539619B (en) * | 2022-03-03 | 2023-09-29 | 浙江鑫鼎塑业股份有限公司 | Preparation method of bio-based environment-friendly plasticizer for polyethylene resin |
| CN115746011A (en) * | 2022-12-09 | 2023-03-07 | 河南省科学院化学研究所有限公司 | Isosorbide isooctanoate bio-based plasticizer and preparation method and application thereof |
| CN115746011B (en) * | 2022-12-09 | 2024-03-15 | 河南省科学院化学研究所有限公司 | Isosorbide isooctyl ester bio-based plasticizer and preparation method and application thereof |
| CN116425766A (en) * | 2023-04-18 | 2023-07-14 | 北京工商大学 | Epoxy isosorbide plasticizer and preparation method thereof |
| CN116731033A (en) * | 2023-08-14 | 2023-09-12 | 烟台舜康生物科技有限公司 | Preparation method of epoxy isosorbide plasticizer |
| CN116731033B (en) * | 2023-08-14 | 2023-10-03 | 烟台舜康生物科技有限公司 | Preparation method of epoxy isosorbide plasticizer |
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