CN115160138A - Method for preparing antioxidant 1076 - Google Patents
Method for preparing antioxidant 1076 Download PDFInfo
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- CN115160138A CN115160138A CN202210980700.6A CN202210980700A CN115160138A CN 115160138 A CN115160138 A CN 115160138A CN 202210980700 A CN202210980700 A CN 202210980700A CN 115160138 A CN115160138 A CN 115160138A
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- organic solvent
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000001816 cooling Methods 0.000 claims abstract description 32
- 239000013078 crystal Substances 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 14
- 238000004321 preservation Methods 0.000 claims abstract description 13
- 239000012043 crude product Substances 0.000 claims abstract description 12
- 238000007670 refining Methods 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000002156 mixing Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 12
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 11
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000011946 reduction process Methods 0.000 claims description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000011790 ferrous sulphate Substances 0.000 claims description 2
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 7
- 238000007873 sieving Methods 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
Abstract
The invention discloses a method for preparing an antioxidant 1076, which comprises the following steps: the method comprises the steps of firstly, pretreating the antioxidant 1076 crude product, secondly, refining the antioxidant 1076, reducing the synthesized antioxidant 1076 crude product in the scheme, and then, performing measures such as two-stage cooling, heat preservation, seed crystal addition and the like in a compound solvent, so that a needle crystal form can be quickly crystallized, the processes of later crushing, sieving and the like are reduced, and the drying and the addition are easy.
Description
Technical Field
The invention relates to the technical field of antioxidants, and particularly relates to a method for preparing an antioxidant 1076.
Background
The antioxidant 1076 is hindered phenol type antioxidant, is excellent non-pollution and non-toxic antioxidant, has good intermiscibility, no coloration, washing resistance, small volatility and better heat resistance and water resistance extraction performance, and is widely applied to polyolefin, polyamide, polyester, polyvinyl chloride, ABS resin and various rubber and petroleum products. Conventionally, 3, 5-methyl ester and n-octadecanol are used as raw materials for synthesizing the antioxidant 1076, a crude product is obtained through ester exchange reaction, then the antioxidant 1076 is obtained through refining, and the improvement of the synthesis mostly focuses on parameter optimization or screening of a catalyst for synthesis.
The existing antioxidant 1076 has the defects that the crystal form of a prepared product is indefinite, a conventional cooling supersaturated recrystallization mode cannot obtain a crystal form product, and the defects exist in post-treatment: if sticky materials are formed in the centrifugation, the drying is difficult, and the procedures of sieving, crushing and the like are required to be added, so that the cost is increased. In contrast, patent application publication No. CN107417528 discloses a method for forming needle-like crystal form, but there is a disadvantage of long cooling crystallization time during the use process, and improvement is needed.
Disclosure of Invention
In order to solve at least one technical defect, the invention provides the following technical scheme:
the application document discloses a method for preparing an antioxidant 1076, comprising the following steps:
first, pretreatment of crude antioxidant 1076
Mixing the crude antioxidant 1076 product with a reducing agent in an organic solvent, reacting at 20-70 ℃ for 0.5-3.5h, adding acid into the reaction solution to neutralize until the pH value is 6-7, and then recovering the organic solvent to obtain the pretreated antioxidant 1076;
second, refining of antioxidant 1076
Mixing the pretreated antioxidant 1076 with a compound solvent at the temperature of 50-55 ℃, crystallizing by adopting a first-stage cooling, heat preservation and second-stage cooling mode, drying a crystallized product to obtain the refined antioxidant 1076, wherein the first-stage cooling is carried out to 38-40 ℃, seed crystals are added, then the heat preservation is carried out for 0.5-0.8h, and the second-stage cooling is carried out to-5-10 ℃; the compound solvent is formed by mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1-1.5.
In the scheme, the synthetic crude product of the antioxidant 1076 is subjected to reduction treatment, and then the needle crystal form can be quickly crystallized by measures such as two-section cooling, heat preservation, seed crystal addition and the like in a compound solvent, so that the later processes of crushing, sieving and the like are reduced, and the drying and the addition are easy.
Further, the temperature is reduced at the speed of 3-3.5 ℃/10min in the first-stage temperature reduction process, and the temperature is reduced at the speed of 4-5 ℃/10min in the second-stage temperature reduction process. And the temperature is reduced at a specific temperature, so that the crystallization time is shortened, and the required crystal form is prepared.
Further, the mass ratio of the pretreated antioxidant 1076 to the compound solvent is 4-6, the mass ratio of the crude antioxidant 1076 to the organic solvent is 3-4. The pretreatment process of the antioxidant 1076 refers to the patent with the publication number of CN 103724202B.
Further, the acid is hydrochloric acid, sulfuric acid or acetic acid.
Further, the crystallized product is dried under vacuum at 38-42 ℃.
Further, the crude antioxidant 1076 is mixed with sodium thiosulfate, sodium sulfite, ferrous sulfate, sodium borohydride or potassium borohydride in an organic solvent, which is ethyl acetate or toluene.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention improves the refining process of the antioxidant, promotes the reduction of cooling crystallization time through processes such as reduction pretreatment, multi-stage cooling, heat preservation, seed crystal addition and the like, and prepares a needle crystal product which is convenient to use.
Detailed Description
The present invention will be further described with reference to the following specific examples.
In the following examples, the crude antioxidant 1076 is obtained by transesterification of methyl β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate (3, 5-methyl ester) with octadecanol under the action of a catalyst, and the catalyst, solvent, amount ratio, process parameters and the like are referred to conventional techniques, which are not described herein.
The seed crystal is solid antioxidant 1076 in powder form, and the dosage of the seed crystal is 0.6 percent of the mass of the pretreated antioxidant 1076.
Example 1
A method of preparing an antioxidant 1076, comprising the steps of:
first, pretreatment of crude antioxidant 1076
Mixing the antioxidant 1076 crude product with sodium thiosulfate in ethyl acetate, wherein the using amount of the sodium thiosulfate is 10 mol%, the sodium thiosulfate is prepared into 10wt% aqueous solution to be added, the mass of the ethyl acetate is 4 times of that of the antioxidant crude product, controlling the reaction temperature at 35 ℃, and stirring and reacting for 1.5h. Neutralizing the reaction solution with 20wt% of dilute hydrochloric acid until the pH value is 7, washing with water, separating, drying with anhydrous sodium sulfate, filtering, distilling to recover the organic solvent, and obtaining the pretreated antioxidant 1076.
Second, refining of antioxidant 1076
Mixing ethyl acetate, methanol, ethanol and water according to a volume ratio of 1.
Mixing the pretreated antioxidant 1076 with a compound solvent at 50 ℃, stirring to dissolve and uniformly mixing.
And (3) carrying out first-stage cooling on the mixed solution of the compound solvent, cooling to 38 ℃ from 50 ℃ at the speed of 3 ℃/10min, then adding crystal seeds, carrying out heat preservation for 0.5h, then carrying out second-stage cooling, cooling to 0 ℃ from the temperature during heat preservation at the speed of 4 ℃/10min, filtering, and carrying out vacuum drying on a filter product at 40 ℃ to obtain the refined antioxidant 1076.
Example 2
A method of preparing an antioxidant 1076, comprising the steps of:
first, pretreatment of crude antioxidant 1076
Mixing the antioxidant 1076 crude product with sodium thiosulfate in ethyl acetate, wherein the using amount of the sodium thiosulfate is 11 mol%, the sodium thiosulfate is prepared into 10wt% aqueous solution to be added, the mass of the ethyl acetate is 3 times of that of the antioxidant crude product, controlling the reaction temperature at 45 ℃, and stirring for reaction for 2 hours. Neutralizing the reaction solution with 20wt% of dilute hydrochloric acid until the pH value is 7, washing with water, separating, drying with anhydrous sodium sulfate, filtering, distilling to recover the organic solvent, and obtaining the pretreated antioxidant 1076.
Second, refining of antioxidant 1076
Mixing ethyl acetate, methanol, ethanol and water according to a volume ratio of 1.2.3.
Mixing the pretreated antioxidant 1076 with a compound solvent at the temperature of 52 ℃, stirring to dissolve and uniformly mixing.
And (3) carrying out first-stage cooling on the mixed solution of the compound solvent, cooling the mixed solution from 52 ℃ to 39 ℃ at the speed of 3.2 ℃/10min, then adding crystal seeds, carrying out heat preservation for 0.6h, then carrying out second-stage cooling, cooling the mixed solution from the temperature during heat preservation to 5 ℃ at the speed of 4.5 ℃/10min, filtering, and carrying out vacuum drying on a filter product at 40 ℃ to obtain the refined antioxidant 1076.
Example 3
A method of preparing an antioxidant 1076, comprising the steps of:
first, pretreatment of crude antioxidant 1076
Mixing the antioxidant 1076 crude product with sodium thiosulfate in ethyl acetate, wherein the using amount of the sodium thiosulfate is 8 mol%, the sodium thiosulfate is prepared into 10wt% aqueous solution to be added, the mass of the ethyl acetate is 3.5 times of that of the antioxidant crude product, controlling the reaction temperature at 40 ℃, and stirring for reaction for 2 hours. Neutralizing the reaction solution with 20wt% of dilute hydrochloric acid until the pH value is 7, washing with water, separating, drying with anhydrous sodium sulfate, filtering, distilling to recover the organic solvent, and obtaining the pretreated antioxidant 1076.
Second, refining of antioxidant 1076
Mixing ethyl acetate, methanol, ethanol and water according to a volume ratio of 1.5.
Mixing the pretreated antioxidant 1076 with a compound solvent at the temperature of 55 ℃, stirring to dissolve and uniformly mixing.
And (3) carrying out first-stage cooling on the mixed solution of the compound solvent, cooling to 40 ℃ from 55 ℃ at the speed of 3.5 ℃/10min, then adding crystal seeds, carrying out heat preservation for 0.6h, then carrying out second-stage cooling, cooling to 2 ℃ from the temperature during heat preservation at the speed of 5 ℃/10min, filtering, and carrying out vacuum drying on a filter product at 40 ℃ to obtain the refined antioxidant 1076.
Comparative example 1
(1) 97.5% methanol (methanol: water =97.5 v) 2250L was charged in a kettle for crystallization, and heated to 50 ℃ with stirring with the stirring blade;
(2) And (3) cooling the reaction liquid of the antioxidant 1076 after the reaction in the reaction kettle in the synthesis procedure, pressing the reaction liquid into the crystal kettle from the reaction kettle when the temperature is reduced to 120 ℃, and continuously keeping the stirring paddle at 70 r/min.
(3) And opening the condenser of the crystallization kettle, ensuring the condensation reflux of the evaporated methanol, cooling the crystallization kettle to 42 ℃ for 2.5h, and keeping the temperature.
(4) 5kg of dried 1076 crystals (needle crystals) was charged into the reactor, the temperature was lowered to 41 ℃ and the temperature was maintained for 1 hour.
(5) And (4) opening the cold brine in the jacket, cooling the crystal kettle, and performing centrifugal drying when the temperature is reduced to below 5 ℃ for 4 hours.
(7) And transferring the centrifuged product into a vacuum drier, heating to 40 ℃ for drying, sampling every hour in the drying process for volatile matter testing, and determining that the product is qualified when the volatile matter is less than 0.1% according to the Q/SH0067-2007 standard. See example 2 of patent specification publication No. CN 107417528.
Comparative example 2
(1) 97.5% methanol (methanol: water =97.5 v) 2250L was charged in a kettle for crystallization, and heated to 50 ℃ with stirring with the stirring blade;
(2) And (3) cooling the reaction liquid of the antioxidant 1076 after the reaction in the reaction kettle in the synthesis procedure, pressing the reaction liquid into the crystal kettle from the reaction kettle when the temperature is reduced to 120 ℃, and continuously keeping the stirring paddle at 70 r/min.
(3) And opening the condenser of the crystallization kettle, ensuring the condensation reflux of the evaporated methanol, cooling the crystallization kettle to 42 ℃ for 2.5h, and keeping the temperature.
(4) 5kg of dried 1076 crystals (needle crystals) was charged in an autoclave, the temperature was lowered to 41 ℃ and the temperature was maintained for 0.6 hour.
(5) And (4) opening the cold brine in the jacket, cooling the crystal kettle, and performing centrifugal drying when the temperature is reduced to below 5 ℃ for 2.5 h.
(7) And transferring the centrifuged product into a vacuum drier, heating to 40 ℃ for drying, sampling every hour in the drying process for volatile matter testing, and determining that the product is qualified when the volatile matter is less than 0.1% according to the Q/SH0067-2007 standard.
Comparative example 3
In this example, the methanol was removed from the compounded solvent, and the remainder was unchanged from example 3.
The antioxidant 1076 prepared above was tested as shown in the following table:
as can be seen from the data in the table, the antioxidant 1076 prepared by the scheme has excellent performances in purity, light transmittance, melting range and the like, and the needle-shaped crystal form is beneficial to reducing post-treatment procedures and reducing cost.
The above are only preferred embodiments of the present invention, and the scope of the present invention is not limited to the above examples, and all technical solutions that fall under the spirit of the present invention belong to the scope of the present invention. It should be noted that modifications and embellishments within the scope of the invention may occur to those skilled in the art without departing from the principle of the invention, and are considered to be within the scope of the invention.
Claims (6)
1. A method of preparing an antioxidant 1076, comprising the steps of:
first, pretreatment of crude antioxidant 1076
Mixing the crude antioxidant 1076 product with a reducing agent in an organic solvent, reacting at 20-70 ℃ for 0.5-3.5h, adding acid into the reaction solution to neutralize until the pH value is 6-7, and then recovering the organic solvent to obtain the pretreated antioxidant 1076;
second, refining of antioxidant 1076
Mixing the pretreated antioxidant 1076 with a compound solvent at the temperature of 50-55 ℃, crystallizing by adopting a first-stage cooling, heat preservation and second-stage cooling mode, drying a crystallized product to obtain the refined antioxidant 1076, wherein the first-stage cooling is carried out to 38-40 ℃, seed crystals are added, then the heat preservation is carried out for 0.5-0.8h, and the second-stage cooling is carried out to-5-10 ℃; the compound solvent is formed by mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1-1.5.
2. The method of preparing the antioxidant 1076 according to claim 1, wherein: the temperature is reduced at the speed of 3-3.5 ℃/10min in the first-stage temperature reduction process, and the temperature is reduced at the speed of 4-5 ℃/10min in the second-stage temperature reduction process.
3. The method of preparing the antioxidant 1076 according to claim 1, wherein: the mass ratio of the pretreated antioxidant 1076 to the compound solvent is 4-6, the mass ratio of the antioxidant 1076 crude product to the organic solvent is 3-4.
4. The method of preparing the antioxidant 1076 according to claim 1, wherein: the acid is hydrochloric acid, sulfuric acid or acetic acid.
5. The method of preparing the antioxidant 1076 according to claim 1, wherein: the crystallized product is dried under vacuum at 38-42 deg.C.
6. The method of preparing the antioxidant 1076 according to claim 1, wherein: mixing the antioxidant 1076 crude product with sodium thiosulfate, sodium sulfite, ferrous sulfate, sodium borohydride or potassium borohydride in an organic solvent, wherein the organic solvent is ethyl acetate or toluene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210980700.6A CN115160138B (en) | 2022-08-16 | 2022-08-16 | Method for preparing antioxidant 1076 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210980700.6A CN115160138B (en) | 2022-08-16 | 2022-08-16 | Method for preparing antioxidant 1076 |
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| CN115160138A true CN115160138A (en) | 2022-10-11 |
| CN115160138B CN115160138B (en) | 2024-01-02 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206390A (en) * | 1988-05-27 | 1993-04-27 | Ciba-Geigy Corporation | Substituted bisacyloxynaphthacenes |
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| CN101955430A (en) * | 2009-11-26 | 2011-01-26 | 营口市风光化工有限公司 | Method for producing antioxygen 1076 through noncrystalline method |
| CN102746154A (en) * | 2012-07-03 | 2012-10-24 | 山东省临沂市三丰化工有限公司 | Crystallizing method of solid antioxidant |
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| CN103724202A (en) * | 2014-01-10 | 2014-04-16 | 上海华谊（集团）公司 | Refining method of antioxidant 1076 |
| CN107417528A (en) * | 2017-05-02 | 2017-12-01 | 沈阳化工大学 | A kind of method that antioxidant 1076 obtains the crystallization of needle-like crystalline form in methanol solvate |
| CN109896956A (en) * | 2017-12-09 | 2019-06-18 | 山东斯递尔化工科技有限公司 | A kind of synthetic method of antioxidant 1076 |
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-
2022
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|---|---|---|---|---|
| US5206390A (en) * | 1988-05-27 | 1993-04-27 | Ciba-Geigy Corporation | Substituted bisacyloxynaphthacenes |
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| CN109896956A (en) * | 2017-12-09 | 2019-06-18 | 山东斯递尔化工科技有限公司 | A kind of synthetic method of antioxidant 1076 |
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| Title |
|---|
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| Publication number | Publication date |
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| CN115160138B (en) | 2024-01-02 |
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