CN115160138B - Method for preparing antioxidant 1076 - Google Patents
Method for preparing antioxidant 1076 Download PDFInfo
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- CN115160138B CN115160138B CN202210980700.6A CN202210980700A CN115160138B CN 115160138 B CN115160138 B CN 115160138B CN 202210980700 A CN202210980700 A CN 202210980700A CN 115160138 B CN115160138 B CN 115160138B
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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 64
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000001816 cooling Methods 0.000 claims abstract description 33
- 239000013078 crystal Substances 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000007670 refining Methods 0.000 claims abstract description 8
- 238000004321 preservation Methods 0.000 claims abstract description 7
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000012043 crude product Substances 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 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
- 238000001035 drying Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 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
- 239000003638 chemical reducing agent 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
- 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 8
- 230000009467 reduction Effects 0.000 abstract description 4
- 238000007873 sieving Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000010438 heat treatment 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
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011259 mixed solution Substances 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
- 230000006872 improvement Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 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
- 238000005809 transesterification reaction 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
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 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
- 238000002834 transmittance Methods 0.000 description 1
- 238000003809 water extraction 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 first, the preliminary treatment of antioxidant 1076 crude, the second, the refining of antioxidant 1076, the synthetic crude to antioxidant 1076 carries out the reduction treatment in this scheme, later in the compound solvent with two-stage cooling combine measures such as heat preservation, seed crystal interpolation, can crystallize out needle type crystal form fast, reduced processes such as crushing, sieving of later stage, easily stoving and interpolation.
Description
Technical Field
The invention relates to the technical field of antioxidants, in particular to a method for preparing an antioxidant 1076.
Background
The antioxidant 1076 is a hindered phenol antioxidant, is an excellent non-pollution and non-toxic antioxidant, has good compatibility, no coloring, low volatility, good heat resistance and water extraction resistance, and can be widely applied to polyolefin, polyamide, polyester, polyvinyl chloride, ABS resin and various rubber and petroleum products. Conventionally, the synthesis of the antioxidant 1076 takes 3, 5-methyl ester and n-stearyl alcohol as raw materials, a crude product is obtained through transesterification, then the antioxidant 1076 is obtained through refining, and the improvement of the synthesis is mostly focused on optimization of parameters or screening of catalysts for synthesis.
The existing synthesis of the antioxidant 1076 has the defects that the crystal form of the prepared product is variable, the crystal form product cannot be obtained by a conventional cooling supersaturated recrystallization mode, and the defects exist in the post-treatment: if the adhesive is formed in the centrifugation, the drying is difficult, and the procedures of sieving, crushing and the like are needed to be added, so that the cost is increased. In this regard, a method for forming needle-like crystals is disclosed in the patent application publication No. CN107417528, but there are drawbacks in that the cooling crystallization time is long during use, and the like, and improvement is required.
Disclosure of Invention
In order to solve at least one technical defect, the invention provides the following technical scheme:
the application discloses a method for preparing an antioxidant 1076, which comprises the following steps:
pretreatment of first antioxidant 1076 crude product
Mixing the crude antioxidant 1076 with a reducing agent in an organic solvent, reacting for 0.5-3.5h at 20-70 ℃, adding acid into the reaction solution to neutralize to pH value of 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 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 reduced to 38-40 ℃ and seed crystals are added, then the heat preservation is carried out for 0.5-0.8h, and then the second-stage cooling is reduced to-5-10 ℃; the compound solvent is formed by mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1-1.5:2-3:5-6:0.5-0.8.
In the scheme, the synthetic crude product of the antioxidant 1076 is subjected to reduction treatment, and then the needle-shaped crystal form can be rapidly crystallized by adopting measures of two-stage cooling, heat preservation, seed crystal addition and the like in the compound solvent, so that the processes of later crushing, sieving and the like are reduced, and the drying and the addition are easy.
Further, the temperature is reduced at a speed of 3-3.5 ℃/10min in the first-stage temperature reduction process, and the temperature is reduced at a speed of 4-5 ℃/10min in the second-stage temperature reduction process. Cooling at a specific temperature to reduce crystallization time and obtain the required crystal form.
Further, the mass ratio of the pretreated antioxidant 1076 to the compound solvent is 4-6:1, the mass ratio of the crude antioxidant 1076 to the organic solvent is 3-4:1, and the consumption of the reducing agent is 5-15mol%. The pretreatment process of the antioxidant 1076 is referred to in the patent publication No. 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, wherein the organic solvent is ethyl acetate or toluene.
Compared with the prior art, the invention has the beneficial effects that:
1. the improved refining process of the antioxidant promotes the reduction of cooling crystallization time through the processes of reduction pretreatment, multistage cooling, heat preservation, seed crystal addition and the like, prepares a needle-shaped crystal form product, and is convenient to use.
Detailed Description
The invention will be further illustrated with reference to specific examples.
In the following examples, crude antioxidant 1076 is obtained by transesterification of beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate (3, 5-methyl ester) and stearyl alcohol under the action of a catalyst, and the catalyst, the solvent, the amount ratio, the process parameters and the like refer to conventional technologies, and are not described in detail.
The seed crystal is solid antioxidant 1076 and is in powder form, and the dosage of the seed crystal is 0.6% of the mass of the antioxidant 1076 after pretreatment.
Example 1
A method of preparing an antioxidant 1076 comprising the steps of:
pretreatment of first antioxidant 1076 crude product
Mixing the antioxidant 1076 crude product with sodium thiosulfate in ethyl acetate, wherein the dosage of the sodium thiosulfate is 10 mol percent, the sodium thiosulfate is prepared into 10wt% aqueous solution, the mass of the ethyl acetate is 4 times that of the antioxidant crude product, the reaction temperature is controlled to be 35 ℃, and stirring reaction is carried out for 1.5 hours. The reaction solution was neutralized to pH 7 with 20% by weight of diluted hydrochloric acid, then washed with water, separated, dried over anhydrous sodium sulfate, filtered and distilled to recover the organic solvent, and then the pretreated antioxidant 1076 was obtained.
Second, refining of antioxidant 1076
Mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1:2:5:0.5 to form a compound solvent.
The pretreated antioxidant 1076 and the compound solvent are mixed at 50 ℃ and stirred to be dissolved and uniformly mixed.
And (3) carrying out first-stage cooling on the compound solvent mixed solution, cooling to 38 ℃ from 50 ℃ at a speed of 3 ℃/10min, adding seed crystal, preserving heat for 0.5h, then carrying out second-stage cooling, cooling to 0 ℃ from the temperature at the time of preserving heat at a speed of 4 ℃/10min, filtering, and carrying out vacuum drying on the filtrate at 40 ℃ to obtain the refined antioxidant 1076.
Example 2
A method of preparing an antioxidant 1076 comprising the steps of:
pretreatment of first antioxidant 1076 crude product
Mixing the antioxidant 1076 crude product with sodium thiosulfate in ethyl acetate, wherein the dosage of the sodium thiosulfate is 11 mol percent, the sodium thiosulfate is prepared into 10wt% aqueous solution, the mass of the ethyl acetate is 3 times that of the antioxidant crude product, the reaction temperature is controlled to be 45 ℃, and stirring reaction is carried out for 2 hours. The reaction solution was neutralized to pH 7 with 20% by weight of diluted hydrochloric acid, then washed with water, separated, dried over anhydrous sodium sulfate, filtered and distilled to recover the organic solvent, and then the pretreated antioxidant 1076 was obtained.
Second, refining of antioxidant 1076
Mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1.2:2.3:5.4:0.6 to form the compound solvent.
The pretreated antioxidant 1076 and the compound solvent are mixed at the temperature of 52 ℃ and stirred to be dissolved and uniformly mixed.
And (3) carrying out first-stage cooling on the compound solvent mixed solution, cooling to 39 ℃ from 52 ℃ at a speed of 3.2 ℃/10min, adding seed crystals, preserving heat for 0.6h, then carrying out second-stage cooling, cooling to 5 ℃ from the temperature at the time of preserving heat at a speed of 4.5 ℃/10min, filtering, and carrying out vacuum drying on the filtrate at 40 ℃ to obtain the refined antioxidant 1076.
Example 3
A method of preparing an antioxidant 1076 comprising the steps of:
pretreatment of first antioxidant 1076 crude product
Mixing the antioxidant 1076 crude product with sodium thiosulfate in ethyl acetate, wherein the dosage of the sodium thiosulfate is 8 mol percent, the sodium thiosulfate is prepared into 10wt% aqueous solution, the mass of the ethyl acetate is 3.5 times that of the antioxidant crude product, the reaction temperature is controlled to be 40 ℃, and stirring reaction is carried out for 2 hours. The reaction solution was neutralized to pH 7 with 20% by weight of diluted hydrochloric acid, then washed with water, separated, dried over anhydrous sodium sulfate, filtered and distilled to recover the organic solvent, and then the pretreated antioxidant 1076 was obtained.
Second, refining of antioxidant 1076
Mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1.5:3:6:0.8 to form a compound solvent.
The pretreated antioxidant 1076 and the compound solvent are mixed at the temperature of 55 ℃ and stirred to be dissolved and uniformly mixed.
And (3) carrying out first-stage cooling on the compound solvent mixed solution, cooling to 40 ℃ from 55 ℃ at a speed of 3.5 ℃/10min, then adding seed crystal, preserving heat for 0.6h, then carrying out second-stage cooling, cooling to 2 ℃ from the temperature at the time of preserving heat at a speed of 5 ℃/10min, filtering, and carrying out vacuum drying on the filtrate at 40 ℃ to obtain the refined antioxidant 1076.
Comparative example 1
(1) Adding 2250L of 97.5% methanol (methanol: water=97.5:2.5 v: v) into the crystallizer in advance, heating to 50 ℃ and stirring by a stirring paddle;
(2) And cooling the reaction solution of the antioxidant 1076 reacted in the reaction kettle in the synthesis process, and when the temperature is reduced to 120 ℃, pressing the reaction solution from the reaction kettle into the crystal reactor, and continuously maintaining the stirring paddle at 70 revolutions per minute.
(3) Opening a condenser of the crystallizer to ensure the condensation and reflux of the evaporated methanol, cooling the crystallizer to 42 ℃ for 2.5h, and preserving heat.
(4) 5kg of dried 1076 crystals (needle crystals) was added to the reactor, the temperature was lowered to 41℃and the temperature was kept for 1 hour.
(5) And (3) starting cold brine in the jacket, cooling the crystallization kettle, and centrifugally drying when the temperature is reduced to below 5 ℃ for 4 hours.
(7) And transferring the centrifuged product into a vacuum dryer, heating to 40 ℃ for drying, sampling every hour in the drying process, and carrying out volatile testing, wherein the volatile is qualified when less than 0.1% according to Q/SH0067-2007 standard. See example 2 in the patent specification with application publication number CN 107417528.
Comparative example 2
(1) Adding 2250L of 97.5% methanol (methanol: water=97.5:2.5 v: v) into the crystallizer in advance, heating to 50 ℃ and stirring by a stirring paddle;
(2) And cooling the reaction solution of the antioxidant 1076 reacted in the reaction kettle in the synthesis process, and when the temperature is reduced to 120 ℃, pressing the reaction solution from the reaction kettle into the crystal reactor, and continuously maintaining the stirring paddle at 70 revolutions per minute.
(3) Opening a condenser of the crystallizer to ensure the condensation and reflux of the evaporated methanol, cooling the crystallizer to 42 ℃ for 2.5h, and preserving heat.
(4) 5kg of dried 1076 crystals (needle crystals) was added to the reactor, the temperature was lowered to 41℃and the temperature was kept for 0.6 hour.
(5) And (3) starting cold brine in the jacket, cooling the crystallization kettle, and centrifugally drying when the temperature is reduced to below 5 ℃ for 2.5 hours.
(7) And transferring the centrifuged product into a vacuum dryer, heating to 40 ℃ for drying, sampling every hour in the drying process, and carrying out volatile testing, wherein the volatile is qualified when less than 0.1% according to Q/SH0067-2007 standard.
Comparative example 3
Compared with example 3, the methanol is removed from the compound solvent in this example, and the rest is unchanged.
The antioxidant 1076 prepared above was tested as shown in the following table:
from the data in the table, the antioxidant 1076 prepared by the scheme has excellent performances of 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 is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above examples, and all technical solutions belonging to the concept of the present invention belong to the protection scope of the present invention. It should be noted that modifications and adaptations to the present invention may occur to one skilled in the art without departing from the principles of the present invention and are intended to be within the scope of the present invention.
Claims (4)
1. A method of preparing an antioxidant 1076 comprising the steps of:
pretreatment of first antioxidant 1076 crude product
Mixing the crude antioxidant 1076 with a reducing agent in an organic solvent, reacting for 0.5-3.5h at 20-70 ℃, adding acid into the reaction solution to neutralize to pH value of 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 50-55 ℃, crystallizing by adopting a first-stage cooling, heat preservation and second-stage cooling mode, drying the crystallized product to obtain a refined needle-shaped crystal antioxidant 1076, wherein the first-stage cooling is reduced to 38-40 ℃ and seed crystals are added, then the heat preservation is carried out for 0.5-0.8h, and then the second-stage cooling is reduced to 0-5 ℃; the compound solvent is formed by mixing ethyl acetate, methanol, ethanol and water according to the volume ratio of 1-1.5:2-3:5-6:0.5-0.8;
the temperature is reduced at a speed of 3-3.5 ℃/10min in the first-stage temperature reduction process, and at a speed of 4-5 ℃/10min in the second-stage temperature reduction process;
the mass ratio of the pretreated antioxidant 1076 to the compound solvent is 4-6:1, the mass ratio of the crude antioxidant 1076 to the organic solvent is 3-4:1, and the consumption of the reducing agent is 5-15mol%.
2. A method of preparing an antioxidant 1076 according to claim 1 wherein: the acid is hydrochloric acid, sulfuric acid or acetic acid.
3. A method of preparing an antioxidant 1076 according to claim 1 wherein: the crystallized product is dried under vacuum at 38-42 ℃.
4. A method of preparing an 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.
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|---|---|---|---|
| CN202210980700.6A CN115160138B (en) | 2022-08-16 | 2022-08-16 | Method for preparing antioxidant 1076 |
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| CN202210980700.6A CN115160138B (en) | 2022-08-16 | 2022-08-16 | Method for preparing antioxidant 1076 |
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| CN115160138A CN115160138A (en) | 2022-10-11 |
| CN115160138B true CN115160138B (en) | 2024-01-02 |
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|---|---|---|---|---|
| US5206390A (en) * | 1988-05-27 | 1993-04-27 | Ciba-Geigy Corporation | Substituted bisacyloxynaphthacenes |
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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 |
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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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| WO2003042136A2 (en) * | 2001-11-13 | 2003-05-22 | Teva Pharmaceutical Industries, Ltd. | Process for the production of l-dopa ethyl ester |
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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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| CN115160138A (en) | 2022-10-11 |
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