CN115784849A - Method for synthesizing high-melting-point alcohol propoxylate - Google Patents
Method for synthesizing high-melting-point alcohol propoxylate Download PDFInfo
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- CN115784849A CN115784849A CN202211546113.2A CN202211546113A CN115784849A CN 115784849 A CN115784849 A CN 115784849A CN 202211546113 A CN202211546113 A CN 202211546113A CN 115784849 A CN115784849 A CN 115784849A
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- reaction
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- point alcohol
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- propylene oxide
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- 238000000034 method Methods 0.000 title claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 71
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims abstract description 41
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 23
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000002844 melting Methods 0.000 claims abstract description 17
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 16
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000008018 melting Effects 0.000 claims abstract description 16
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 3
- 239000007858 starting material Substances 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000001308 synthesis method Methods 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000006227 byproduct Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- -1 propylene alcohol Chemical compound 0.000 description 6
- 239000002904 solvent Substances 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010146 3D printing Methods 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical group [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing high-melting-point alcohol propoxylate, belonging to the technical field of organic compound synthesis. The invention relates to a method for synthesizing high-melting-point alcohol propoxylate, which comprises the following steps: bisphenol A, bisphenol F, neopentyl glycol, bisphenol fluorene or pentaerythritol with high melting point are taken as starting materials, N-diisopropylethylamine catalyst is added, and propylene carbonate and propylene oxide are taken as reaction monomers to synthesize propoxylate. The invention provides a method for synthesizing propoxylate by using N, N-diisopropylethylamine as a catalyst and using high-melting-point alcohol, propylene carbonate and propylene oxide.
Description
Technical Field
The invention relates to a method for synthesizing high-melting-point alcohol propoxylate, belonging to the technical field of organic compound synthesis.
Background
A method for synthesizing high-melting-point alcohol propoxylate is mainly used for synthesizing propoxylated pentaerythritol ether, propoxylated bisphenol F ether, propoxylated bisphenol fluorene ether, propoxylated bisphenol A ether, propoxylated neopentyl glycol ether and the like. The carbon-oxygen chain and the aromatic ring or branched chain structure in the molecule of the product can endow the material with certain toughness and rigidity, thereby improving the structure and the property of the polymer. Can synthesize various functional high molecular substances such as polyester, polyurethane, polycarbonate and the like, and can be widely applied to polyurethane glue, UV (ultraviolet) photocuring paint, polyurethane elastomer and the like. The method can be applied to various fields, such as chemical coatings, 3D printing, automobile manufacturing, electronics, aerospace and the like.
The melting point of raw materials such as pentaerythritol, bisphenol F, bisphenol fluorene, bisphenol A, neopentyl glycol and the like is high. In the propoxylation reaction, the product is synthesized mostly by a solvent method or a melting method. The solvent method brings a series of problems of energy consumption, application times, complex device and the like caused by solvent recovery, and the synthesis method causes high production cost. When a melting method is adopted to synthesize propoxylate products from pentaerythritol, bisphenol F, bisphenol fluorene and bisphenol A with high melting points, the problems of decomposition of raw materials, deepening of color and the like can be caused, and the product quality is influenced.
In addition, in the synthesis of propoxylated pentaerythritol ether, propoxylated bisphenol F ether, propoxylated bisphenol fluorene ether, propoxylated bisphenol a ether, propoxylated neopentyl glycol ether and other products, published literature reports that the product is prepared by using alkali metal hydroxide such as KOH, naOH and the like as a catalyst, but the method needs product refining to obtain a finished product, and the production cost of the product is increased.
The existing method has the problems of high production cost of synthetic products or product quality and the like, which reduces the added value and market competitiveness of the products.
Disclosure of Invention
Aiming at the defects of the existing production method, the invention provides a synthesis method for synthesizing a propoxylate by using N, N-diisopropylethylamine catalyst and high-melting-point alcohol, propylene carbonate and propylene oxide.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a method for synthesizing a high melting point alcohol propoxylate comprises the following steps: bisphenol A, bisphenol F, neopentyl glycol, bisphenol fluorene or pentaerythritol with high melting point (the melting point temperature is higher than 120 ℃) are taken as initiator raw materials, N-diisopropylethylamine catalyst is added, and propylene carbonate and propylene oxide are taken as reaction monomers to synthesize the propoxylate.
The dosage of the catalyst is 0.1 to 10 per mill of the sum of the mass of the initiator raw material, the propylene carbonate and the propylene oxide.
The dosage of the catalyst is 3 per mill of the sum of the mass of the initiator raw material, the propylene carbonate and the propylene oxide.
In the synthesis process, the reaction temperature is 85 to 140 ℃, and the reaction pressure is-0.098 to 0.50Mpa.
During the synthesis, the reaction temperature is 105 ℃.
The molar ratio of the initiator to the propylene carbonate is (2) - (1) - (3).
The mole ratio of the initiator to the propylene carbonate is 1.
The molar ratio of the initiator to the propylene oxide is 1.
A method for synthesizing high-melting-point alcohol propoxylates comprises the following specific steps:
(1) Adding an initiator, a catalyst and propylene carbonate into a reaction kettle, and replacing air in the reaction kettle with nitrogen;
(2) Starting stirring, controlling the reaction temperature to be 85-140 ℃, controlling the pressure to be-0.080-0.098 Mpa, and reacting for 2-5 h;
(3) Introducing a required amount of propylene oxide into the reaction kettle, and carrying out polymerization reaction for 2-10 h under the conditions that the reaction temperature is 85-140 ℃ and the reaction pressure is 0-0.35 MPa;
(4) And after the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product.
Compared with the prior art, the invention has the following outstanding advantages and positive effects:
1. the propylene carbonate not only serves as a propylene oxide reagent, but also can serve as a dispersant in the reaction process of synthesizing the propoxylate because the propylene carbonate is liquid at room temperature, so that the initiator can react with the propylene carbonate and the propylene oxide under stirring.
2. N, N-diisopropylethylamine is used as a catalyst, and the side reaction can be inhibited due to the large steric hindrance of the N, N-diisopropylethylamine. The excellent catalytic property of N, N-diisopropylethylamine, the propylene alcohol by-product generated by propylene oxide isomerization of the prepared propoxylate product is less than 10ppm, the color is light, and the color (Pt-Co) is less than or equal to 20.
3. The boiling point of the N, N-diisopropylethylamine is 127 ℃, the N, N-diisopropylethylamine can be removed in vacuum after the reaction is finished, a refining step is not needed, and the production cost is saved.
Specific examples
The analysis method comprises the following steps:
number average molecular weight (Mn) of the product was measured by gel chromatography using Agilent 1200 liquid chromatograph G1328B.
The content of the by-product of acrylic alcohol was measured by using high performance liquid chromatography RID-10a, manufactured by Shimadzu corporation, japan.
Preparation of the reaction kettle before implementation: washing a 2.5L high-pressure glass reaction kettle with distilled water for 3 times, drying the reaction kettle, and cooling to normal temperature for later use.
Example 1
The propoxylated pentaerythritol ether product was designed to be synthesized with a design molecular weight of 254.
Adding 544g of pentaerythritol, 3g of N, N-diisopropylethylamine catalyst and 408g of propylene carbonate into a reaction kettle, and replacing air in the reaction kettle with nitrogen for 3 times. Stirring is started, the reaction temperature is 105 ℃, the pressure is controlled to be-0.080 to 0.098Mpa, and the reaction is carried out for 4 hours. And (3) introducing 232g of propylene oxide into the reaction kettle, and carrying out polymerization reaction for 3 hours at the reaction temperature of 105 ℃ and the reaction pressure of 0-0.35 MPa. And after the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product. Product analysis: the content of the propylene alcohol by-product is 2.8ppm; the color (Pt-Co) of the product is 8, and the number average molecular weight is 252.
Example 2
The propoxylated bisphenol F ether product was designed to be synthesized with a design molecular weight of 548.
Adding 3g of bisphenol F400g, 3g of N, N-diisopropylethylamine catalyst and 204g of propylene carbonate into a reaction kettle, and replacing air in the reaction kettle with nitrogen for 3 times. Stirring is started, the reaction temperature is 120 ℃, the pressure is controlled to be-0.080 to 0.098Mpa, and the reaction is carried out for 2 hours. And (3) introducing 580g of propylene oxide into the reaction kettle, and carrying out polymerization reaction for 6 hours at the reaction temperature of 120 ℃ and the reaction pressure of 0-0.35 MPa. And after the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product. Product analysis: the content of the propylene alcohol by-product is 3.5ppm; the color (Pt-Co) of the product is 9, and the number average molecular weight is 546.
Example 3
The designed molecular weight of the product is 582.
700g of bisphenol fluorene, 8g of N, N-diisopropylethylamine catalyst and 306g of propylene carbonate are added into the reaction kettle, and nitrogen is replaced for 3 times by replacing air in the reaction kettle with nitrogen. Stirring is started, the reaction temperature is 110 ℃, the pressure is controlled to be-0.080 to 0.098Mpa, and the reaction is carried out for 3 hours. 290g of propylene oxide is pumped into the reaction kettle, and polymerization reaction is carried out for 4 hours under the conditions that the reaction temperature is 110 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product. Product analysis: the content of the propylene alcohol by-product is 4.1ppm; the color (Pt-Co) of the product is 7, and the number average molecular weight is 580.
Example 4
The propoxylated bisphenol a ether product was designed to be synthesized with a design molecular weight of 408.
570g of bisphenol A, 3g of N, N-diisopropylethylamine catalyst and 204g of propylene carbonate were added to a reaction vessel, and the atmosphere in the reaction vessel was replaced with nitrogen gas for 3 times. Stirring is started, the reaction temperature is 110 ℃, the pressure is controlled to be-0.080 to 0.098Mpa, and the reaction is carried out for 3.5h. 319g of propylene oxide is introduced into the reaction kettle, and polymerization reaction is carried out for 4 hours under the conditions that the reaction temperature is 110 ℃ and the reaction pressure is 0-0.35 MPa. After the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product. Product analysis: the content of the propylene alcohol by-products is 3.2ppm; the color (Pt-Co) of the product is 12, and the number average molecular weight is 406.
Example 5
The propoxylated neopentyl glycol ether product was designed to be synthesized with a designed molecular weight of 221.
The neopentyl glycol 520g, the N, N-diisopropylethylamine catalyst amount 3g and the propylene carbonate 255g were added to the reaction kettle, and the air in the reaction kettle was replaced with nitrogen gas for 3 times. Stirring is started, the reaction temperature is 110 ℃, the pressure is controlled to be-0.080 to 0.098Mpa, and the reaction is carried out for 3 hours. 435g of propylene oxide is pumped into the reaction kettle, and polymerization reaction is carried out for 4.5h under the conditions that the reaction temperature is 110 ℃ and the reaction pressure is 0-0.35 MPa. And after the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product. Product analysis: the content of the propylene alcohol by-products is 3.5ppm; the color (Pt-Co) of the product is 10, and the number average molecular weight is 220.
The foregoing is illustrative of the preferred embodiments of the present invention, and it should be noted that it is apparent to those skilled in the art that a number of modifications and adaptations to the formulation or reaction conditions may be made without departing from the principles of the present invention and are intended to be within the scope of the present invention.
Claims (9)
1. The synthesis method of the high-melting-point alcohol propoxylate is characterized by comprising the following steps of: high-melting point bisphenol A, bisphenol F, neopentyl glycol, bisphenol fluorene or pentaerythritol are used as starting materials, N-diisopropylethylamine catalysts are added, and propylene carbonate and propylene oxide are used as reaction monomers to synthesize propoxylates.
2. The method of claim 1 for synthesizing a high melting point alcohol propoxylate wherein: the dosage of the catalyst is 0.1 to 10 per mill of the sum of the mass of the initiator raw material, the propylene carbonate and the propylene oxide.
3. The method of claim 2 wherein the high melting point alcohol propoxylate is prepared by: the dosage of the catalyst is 3 per mill of the sum of the mass of the initiator raw material, the propylene carbonate and the propylene oxide.
4. The method of claim 1 for synthesizing a high melting point alcohol propoxylate wherein: in the synthesis process, the reaction temperature is 85 to 140 ℃, and the reaction pressure is-0.098 to 0.50Mpa.
5. The method of claim 4 wherein the high melting point alcohol propoxylate is prepared by: during the synthesis, the reaction temperature was 105 ℃.
6. The method of claim 1 for synthesizing a high melting point alcohol propoxylate wherein: the molar ratio of the initiator to the propylene carbonate is (2) - (1) - (3).
7. The method of claim 6 for synthesizing a high melting point alcohol propoxylate wherein: the mole ratio of the initiator to the propylene carbonate is 1.
8. The method of claim 1 for synthesizing a high melting point alcohol propoxylate wherein: the molar ratio of the initiator to the propylene oxide is 1.
9. The method for synthesizing a high melting point alcohol propoxylate as defined in claim 1 comprising the steps of:
(1) Adding an initiator, a catalyst and propylene carbonate into a reaction kettle, and replacing air in the reaction kettle with nitrogen;
(2) Stirring is started, the reaction temperature is 85 to 140 ℃, the pressure is controlled to be minus 0.080to 0.098Mpa, and the reaction is carried out for 2 to 5 hours;
(3) Introducing a required amount of propylene oxide into a reaction kettle, and carrying out polymerization reaction for 2-10 h under the conditions that the reaction temperature is 85-140 ℃ and the reaction pressure is 0-0.35 MPa;
(4) And after the reaction is finished, removing the N, N-diisopropylethylamine catalyst and a small amount of unreacted propylene oxide in vacuum, and cooling the materials to obtain a finished product.
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| CN115784849B CN115784849B (en) | 2024-04-05 |
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| WO2022044477A1 (en) * | 2019-12-25 | 2022-03-03 | サカタインクス株式会社 | Inkjet textile-printing ink composition, method for inkjet textile printing, and inkjet textile-printed material |
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| WO2022044477A1 (en) * | 2019-12-25 | 2022-03-03 | サカタインクス株式会社 | Inkjet textile-printing ink composition, method for inkjet textile printing, and inkjet textile-printed material |
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