WO2024146158A1 - Procédé de préparation d'antioxydant 3052 - Google Patents
Procédé de préparation d'antioxydant 3052 Download PDFInfo
- Publication number
- WO2024146158A1 WO2024146158A1 PCT/CN2023/117360 CN2023117360W WO2024146158A1 WO 2024146158 A1 WO2024146158 A1 WO 2024146158A1 CN 2023117360 W CN2023117360 W CN 2023117360W WO 2024146158 A1 WO2024146158 A1 WO 2024146158A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- antioxidant
- reaction
- tert
- methylphenol
- butyl
- Prior art date
Links
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 63
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 17
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 43
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- 239000011973 solid acid Substances 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000012768 molten material Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000004408 titanium dioxide Substances 0.000 claims description 11
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 30
- 150000001263 acyl chlorides Chemical class 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000002910 solid waste Substances 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000002085 irritant Substances 0.000 abstract 1
- 231100000021 irritant Toxicity 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007791 liquid phase Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 10
- 229930185605 Bisphenol Natural products 0.000 description 7
- 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 description 7
- 238000001914 filtration Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101001121408 Homo sapiens L-amino-acid oxidase Proteins 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 102100026388 L-amino-acid oxidase Human genes 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- INKDAKMSOSCDGL-UHFFFAOYSA-N [O].OC1=CC=CC=C1 Chemical compound [O].OC1=CC=CC=C1 INKDAKMSOSCDGL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- -1 olefin anhydride Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 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
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- 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
Definitions
- step S2 After the reaction of step S1 is completed, methylal and a catalyst are added to the reactor of step S1 under nitrogen protection, and 2-tert-butyl-4-methylphenol is slowly added dropwise to the reactor under stirring conditions for reflux reaction. After the reaction is completed, the antioxidant 3052 product is obtained through post-treatment.
- step S2 the molar ratio of 2-tert-butyl-4-methylphenol to methylal in step S2 is 1:(2-3);
- the entire preparation process does not require high temperature and high pressure conditions, the reaction process conditions are mild, the post-treatment is simple, and the operation cost is low.
- the preparation method of the present invention can obtain a high-yield antioxidant 3052 product.
- the solvent is any one of toluene and high-boiling-point petroleum ether or a mixture of the two.
- the high-boiling-point petroleum ether is petroleum ether with a boiling point of 90°C-120°C.
- step S1 the molar ratio of 2-tert-butyl-4-methylphenol to acrylic anhydride is: (1-1.1): 1;
- the molar ratio of 2-tert-butyl-4-methylphenol in step S2 to 2-tert-butyl-4-methylphenol in step S1 is 1:1;
- step S2 Under nitrogen protection, add methylal (1.1 mol 83.6 g), concentrated sulfuric acid (2.5 g) and titanium dioxide SO 4 2- /TiO 2 solid acid catalyst (2.5 g) into the reactor of step S1. Under stirring, slowly add 2-tert-butyl-4-methylphenol (0.55 mol 90.2 g) dropwise into the reactor. During the reaction, the liquid phase tracks the progress of the reaction. The reaction is kept warm for 3 hours. After the reaction is completed, the solid acid catalyst is separated by filtration. The solvent is then removed by distillation under reduced pressure to obtain a molten material. The molten material is recrystallized with ethanol and dried to obtain an antioxidant 3052 product. The purity of the antioxidant 3052 product is 99.3% and the yield is 86.5% as determined by liquid phase.
- step S2 Under nitrogen protection, add methylal (1.05mol 79.8g), concentrated sulfuric acid (4.3g) and titanium dioxide SO42- / TiO2 solid acid catalyst (4.3g) into the reactor of step S1. Under stirring, slowly add 2-tert-butyl-4-methylphenol (0.525mol 86.1g) dropwise into the reactor. During the reaction, the liquid phase tracks the progress of the reaction. The reaction is kept warm for 2.5h. After the reaction is completed, the solid acid catalyst is separated by filtration. The solvent is then removed by distillation under reduced pressure to obtain a molten material. The molten material is recrystallized with methanol and dried to obtain an antioxidant 3052 product. The purity of the antioxidant 3052 product is 78.6% and the yield is 35.2% as determined by liquid phase.
- the antioxidant 3052 product was prepared by the same method as in Example 1, except that concentrated sulfuric acid was not added in step S2.
- the final antioxidant 3052 product has a purity of 83.2% and a yield of 50.2%.
- step S2 From the comparison of the experimental data of Comparative Example 3 and Example 1, it can be seen that no more concentrated sulfuric acid is added in step S2, which will lead to a decrease in product yield, because in step S2, concentrated sulfuric acid can provide an acidic environment, which is more conducive to the catalytic reaction.
- the antioxidant 3052 product was prepared by the same method as in Example 1, except that the amount of methylal added in step S2 was 39.9 g (0.525 mol).
- the final antioxidant 3052 product had a purity of 96.1% and a yield of 58.9%.
- step S2 reducing the amount of methylal added in step S2 will cause the purity and yield of the product to decrease.
- Methylal plays the role of a bridging agent in the reaction, and the presence of methylal is conducive to the smooth progress of the reaction. If the amount of methylal is reduced, the reaction yield will be significantly reduced. However, if methylal is excessive, resulting in a reaction residue, methylal will be removed from the system in the vacuum distillation of the post-treatment, which will not affect the purity of the final product.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention relève du domaine technique de la synthèse organique, et concerne en particulier un procédé de préparation d'un antioxydant 3052. Le procédé de préparation comprend les étapes suivantes : S1, qui consiste à ajouter, sous une protection d'azote, du 2-tert-butyl-4-méthylphénol, un solvant et un catalyseur acide à un réacteur, faire chauffer et agiter le mélange, puis ajouter lentement un anhydride acrylique goutte à goutte au réacteur, et après achèvement de l'addition, soumettre le mélange à une réaction de conservation de chaleur; et S2, qui consiste à ajouter, après la fin de la réaction de l'étape S1, du méthylal et un catalyseur au réacteur de l'étape S1, ajouter lentement du 2-tert-butyl-4-méthylphénol goutte à goutte au réacteur dans une condition d'agitation, soumettre le mélange à une réaction de reflux, et après achèvement de la réaction, soumettre le produit de réaction à un post-traitement pour obtenir un produit antioxydant 3052. L'utilisation de matières premières irritantes et dangereuses telles que le chlorure d'acyle peut être évitée dans le procédé de préparation ; en outre, aucun sel organique n'est généré pendant le procédé de préparation, ce qui permet d'éviter la génération de déchets solides, de telle sorte que le procédé de préparation est plus respectueux de l'environnement et mieux approprié pour une utilisation industrielle.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310013379.9 | 2023-01-05 | ||
CN202310013379.9A CN116217390B (zh) | 2023-01-05 | 2023-01-05 | 一种抗氧剂3052的制备方法 |
Publications (1)
Publication Number | Publication Date |
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WO2024146158A1 true WO2024146158A1 (fr) | 2024-07-11 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/CN2023/117360 WO2024146158A1 (fr) | 2023-01-05 | 2023-09-07 | Procédé de préparation d'antioxydant 3052 |
Country Status (2)
Country | Link |
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CN (1) | CN116217390B (fr) |
WO (1) | WO2024146158A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116217390B (zh) * | 2023-01-05 | 2024-04-19 | 安徽新秀化学股份有限公司 | 一种抗氧剂3052的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5214193A (en) * | 1991-02-18 | 1993-05-25 | Sumitomo Chemical Company, Limited | Production of bisphenol monoester |
CN101693662A (zh) * | 2009-10-14 | 2010-04-14 | 山西万化科技有限公司 | 一种双酚单丙烯酸酯类耐热稳定剂的制备方法 |
CN105523899A (zh) * | 2015-07-06 | 2016-04-27 | 中国科学院宁波材料技术与工程研究所 | 一种双酚类化合物抗氧剂的清洁生产方法及应用 |
CN116217390A (zh) * | 2023-01-05 | 2023-06-06 | 安徽新秀化学股份有限公司 | 一种抗氧剂3052的制备方法 |
-
2023
- 2023-01-05 CN CN202310013379.9A patent/CN116217390B/zh active Active
- 2023-09-07 WO PCT/CN2023/117360 patent/WO2024146158A1/fr unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5214193A (en) * | 1991-02-18 | 1993-05-25 | Sumitomo Chemical Company, Limited | Production of bisphenol monoester |
CN101693662A (zh) * | 2009-10-14 | 2010-04-14 | 山西万化科技有限公司 | 一种双酚单丙烯酸酯类耐热稳定剂的制备方法 |
CN105523899A (zh) * | 2015-07-06 | 2016-04-27 | 中国科学院宁波材料技术与工程研究所 | 一种双酚类化合物抗氧剂的清洁生产方法及应用 |
CN116217390A (zh) * | 2023-01-05 | 2023-06-06 | 安徽新秀化学股份有限公司 | 一种抗氧剂3052的制备方法 |
Non-Patent Citations (2)
Title |
---|
JUN-LIN GUO, TONG XI-WAN, ;XIN MING, YU LI-YING, NING BO: "Synthesis of Antioxidant 3052 by Multi-component One-pot Reaction", SULIAO KEJI - PLASTICS SCIENCE AND TECHNOLOGY, DALIAN SULIAO YANJIUSUO, DALIAN, CN, vol. 48, no. 4, 27 March 2020 (2020-03-27), CN , pages 99 - 102, XP093189466, ISSN: 1005-3360, DOI: 10.15925/j.cnki.issn1005-3360.2020.04.025 * |
TIAN-YONG ZHANG, CHI LI-FENG, XIA WEN-JUAN, CHAI YI, ZHANG YOU-LAN: "Synthesis of Antioxidant 2246", CHEMICAL INDUSTRY AND ENGINEERING, vol. 26, no. 1, 15 January 2009 (2009-01-15), pages 19 - 22, XP093189464 * |
Also Published As
Publication number | Publication date |
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CN116217390A (zh) | 2023-06-06 |
CN116217390B (zh) | 2024-04-19 |
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