CN110759815A - Processing method of BHT (butylated hydroxytoluene) competitive product - Google Patents
Processing method of BHT (butylated hydroxytoluene) competitive product Download PDFInfo
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- CN110759815A CN110759815A CN201911049559.2A CN201911049559A CN110759815A CN 110759815 A CN110759815 A CN 110759815A CN 201911049559 A CN201911049559 A CN 201911049559A CN 110759815 A CN110759815 A CN 110759815A
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 235000010354 butylated hydroxytoluene Nutrition 0.000 title claims abstract description 70
- 239000004322 Butylated hydroxytoluene Substances 0.000 title claims abstract description 51
- 229940095259 butylated hydroxytoluene Drugs 0.000 title claims abstract description 51
- 238000003672 processing method Methods 0.000 title claims abstract description 8
- 230000002860 competitive effect Effects 0.000 title claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims abstract description 27
- 230000008025 crystallization Effects 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000001816 cooling Methods 0.000 claims abstract description 21
- 239000013078 crystal Substances 0.000 claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 18
- 239000012452 mother liquor Substances 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 239000011780 sodium chloride Substances 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 238000007599 discharging Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000004806 packaging method and process Methods 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 4
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 21
- 239000012267 brine Substances 0.000 claims description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- WYSSJDOPILWQDC-UHFFFAOYSA-N 2,4-ditert-butyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C WYSSJDOPILWQDC-UHFFFAOYSA-N 0.000 description 1
- ZZZRZBIPCKQDQR-UHFFFAOYSA-N 2,4-ditert-butyl-6-methylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O ZZZRZBIPCKQDQR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000009920 food preservation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012629 purifying agent Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a processing method of a BHT (butylated hydroxytoluene) competitive product, which comprises the following specific steps of: adding a certain amount of crude BHT, water and sodium chloride into a crystallization kettle, heating to 50-52 ℃, then cooling to 40-42 ℃, rapidly crystallizing to separate BHT crystals, and then cooling to 28-30 ℃; standing for layering, discharging mother liquor, and retaining upper-layer crystals; then heating to 68-70 ℃ for melting; transferring upper layer crystals (melted materials) into a secondary crystallization kettle through a metering pump, quantitatively adding ethanol and water, starting stirring, heating to 68-70 ℃, then cooling to 58-60 ℃, adding crystal seeds into the crystallization kettle to promote rapid crystallization, keeping the temperature for 1.8-2.2h, then cooling to 48-50 ℃ at the temperature of 2 ℃ per hour, cooling to 23-25 ℃ at the temperature of 5 ℃ per hour, then enabling the materials to pass through a self-discharging centrifuge to realize rapid separation, and enabling the solids to enter a drying and packaging system to obtain the BHT fine product. The method has high yield, the mass fraction of the obtained 2, 6-di-tert-butyl-4-methylphenol is as high as more than 99.99 percent, and the color retention can be realized for more than three years.
Description
Technical Field
The invention relates to the field of fine chemicals preparation, in particular to a processing method of a BHT (butylated hydroxytoluene) competitive product.
Background
BHT has the chemical name 2, 6-di-tert-butyl-4-methylphenol, also called dibutylhydroxytoluene, BHT for short, and is also called as follows: an antioxidant 264. The method takes m-cresol, p-cresol and isobutene as raw materials, takes concentrated sulfuric acid as a catalyst, takes alumina as a dehydrating agent, and generates a 2, 6-di-tert-butyl-p-cresol crude product through alkylation reaction. BHT has antioxidant effects in cosmetics, pharmaceuticals, aircraft fuels, rubber, petroleum products, and specimens. Antioxidants are organic compounds that inhibit or retard the thermal oxidation of polymers and other organic compounds in air. In general terms, it is a substance that prevents the deterioration of a polymer material due to oxidation. Is used as antioxidant in food processing. BHT was patented in 1947. BHT was approved by the U.S. Food and Drug Administration (FDA) in 1954 for food preservation. BHT and free radicals produce chemical reactions and slow the rate of redox reactions (i.e., rancidity reactions) in food. Thereby maintaining the color, smell and taste of the food. White crystals turn yellow in color with light and gradually darken. Dissolving in benzene, toluene, solvent, methyl ethyl ketone, ethanol, isopropanol, petroleum ether, and oleum Lini, and dissolving in water and 10 deg.C caustic soda solution. BHT may also be added to avoid the production of harmful peroxidized organics in the production of certain materials such as tetrahydrofuran and diethyl ether.
The crude BHT had the following composition: 2-t-butyl-p-cresol, 6-t-butyl-m-cresol, 4, 6-di-t-butyl-o-cresol, 4, 6-di-t-butyl-m-cresol, 2, 6-di-t-butyl-4-methylphenol, and the like. Wherein the mass fraction of the 2, 6-di-tert-butyl-4-methylphenol is 80-95%.
In the prior art, a solvent crystallization method is generally adopted for purifying a BHT crude product, the yield of the BHT crude product is lower than 40%, the safety risk is high, the energy consumption of a recovered solvent is high, the mass fraction of the produced product is lower than 99.9%, the product is easy to deteriorate, and the color is difficult to maintain.
Disclosure of Invention
The invention aims to: provides a processing method of BHT fine product.
In order to achieve the above purpose, the invention provides the following technical scheme:
a processing method of a BHT (butylated hydroxytoluene) competitive product comprises the following specific steps:
(1) primary brine crystallization: adding the BHT crude product, water and sodium chloride into a crystallization kettle, heating to 50-52 ℃, then cooling at 2 ℃ per hour to 40-42 ℃, rapidly crystallizing to separate BHT crystals, and then cooling to 28-30 ℃;
(2) standing and layering: standing for layering, centrifuging to discharge mother liquor, and retaining upper-layer crystals; then heating to 68-70 ℃ for complete melting;
(3) and (3) secondary alcohol water crystallization: adding the product obtained in the step (2), ethanol and water into a secondary crystallization kettle, starting stirring, heating to 68-70 ℃, cooling to 58-60 ℃ at the rate of 4 ℃ per hour, adding powdery seed crystals into the crystallization kettle, quickly crystallizing, preserving heat for 1.8-2.2 hours, cooling to 48-50 ℃ at the temperature of 2 ℃ per hour, cooling to 23-25 ℃ at the temperature of 5 ℃ per hour, using a self-discharging centrifuge, enabling the materials to pass through the self-discharging centrifuge to realize quick separation, and enabling the solid to enter a drying and packaging system to obtain a BHT (butylated hydroxytoluene) refined product.
Preferably, in step (1), the crude BHT: water: the mass ratio of sodium chloride is 1:0.5: (0.005-0.025).
Preferably, the standing and layering time in the step (2) is 25-35 min.
Preferably, the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in the mother liquor of the lower layer after the layering in the step (2) is less than 40%, and the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in the crystal of the upper layer is more than 99.0%.
Preferably, the lower mother liquor after layering in the step (2) is directly packaged and sold as one of raw materials of antioxidant BHA.
Preferably, the stirring speed in step (3) is 50-60 r/min.
Preferably, the mass ratio of the product of the step (2) in the step (3) to ethanol to water is 1: 0.3:0.1.
Preferably, the mass fraction of the 2, 6-di-tert-butyl-4-methylphenol in the BHT refined product in the step (3) is more than 99.99%.
Preferably, the powder seed crystal in the step (3) is BHT with the mass fraction of more than 99.5%, and the adding amount of the powder seed crystal accounts for 0.01-0.02% of the mass of the crude BHT.
The invention has the beneficial effects that:
1) in the first step, a brine crystallization method is adopted, so that high yield can be realized, material waste is reduced, and the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in the mother liquor is reduced to the maximum extent and is less than 40%. In a normal solvent purifying agent crystallization method, the mass fraction of the 2, 6-di-tert-butyl-4-methylphenol in the mother liquor reaches more than 70 percent.
2) Sodium chloride is added into pure water to become brine, so that the specific gravity of water can be properly increased, the materials can be quickly layered, the solubility of 2, 6-di-tert-butyl-4-methylphenol in the water phase is greatly reduced, and the yield is improved.
3) By adopting the alcohol water crystallization, high-purity 2, 6-di-tert-butyl-4-methylphenol and high-quality BHT can be realized, the long-term storage is facilitated, and the risk of color change is avoided. Most of the shelf life of BHT in the current market can not exceed half a year, and the BHT fine product prepared by adopting brine crystallization and an alcohol-water method can not change color for more than three years due to high mass fraction.
Drawings
FIG. 1 is a process flow diagram of the present invention.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
A processing method of a BHT (butylated hydroxytoluene) competitive product comprises the following specific steps:
(1) primary brine crystallization: mixing a BHT crude product, water and sodium chloride according to a mass ratio of 1:0.5:0.02, adding the mixture into a crystallization kettle, heating to 50 ℃ within 1 hour, then cooling to 2 ℃ per hour, cooling to 40 ℃, quickly crystallizing and separating BHT crystals, and then cooling to 30 ℃;
when brine is crystallized for the first time, the specific gravity of the solution is adjusted by adding sodium chloride, so that the method is favorable for quick layering, the production period is shortened, the productivity is improved, the solubility of organic matters in a water layer is reduced by adding sodium chloride, and the yield is improved.
(2) Standing and layering: standing for layering for 30min, centrifuging to discharge mother liquor, and retaining upper layer crystals; then heating to 70 ℃ to completely melt;
wherein, the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in the layered mother liquor at the lower layer is below 40%, and the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in the crystal at the upper layer is above 99.0%.
Through standing and layering, the mother liquor is effectively separated from the crystallized 2, 6-di-tert-butyl-4-methylphenol, and the mother liquor is reduced to be brought into the next secondary crystallization process.
(3) And (3) secondary alcohol water crystallization: adding the product obtained in the step (2), ethanol and water into a secondary crystallization kettle according to the mass ratio of 1:0.5:0.025, starting stirring at the stirring speed of 55r/min, heating to 70 ℃, cooling to 60 ℃ at the speed of 4 ℃ per hour, adding powdered seed crystal BHT (the mass fraction is more than 99.5%) which accounts for one ten thousandth of the mass of a crude BHT product into the crystallization kettle, quickly crystallizing, keeping the temperature for 2 hours, cooling to 50 ℃ at the temperature of 2 ℃ per hour, cooling to 25 ℃ at the temperature of 5 ℃ per hour, allowing the material to pass through a self-discharging centrifuge to realize quick separation, and allowing the solid to enter a drying and packaging system to obtain a fine BHT product.
The 2, 6-di-tert-butyl-4-methylphenol is further purified by secondary alcohol-water crystallization, and the mass fraction is more than 99.99 percent. The mother liquor is centrifugally separated by centrifugation and is used for primary brine crystallization, so that waste is avoided. The residual ethanol and water on the surface layer are dried and volatilized by drying, so that the moisture and residual solvent in the product meet the requirements.
Claims (9)
1. A processing method of a BHT (butylated hydroxytoluene) competitive product is characterized by comprising the following steps: the method comprises the following specific steps:
(1) primary brine crystallization: adding the BHT crude product, water and sodium chloride into a crystallization kettle, heating to 50-52 ℃, then cooling at 2 ℃ per hour to 40-42 ℃, rapidly crystallizing to separate BHT crystals, and then cooling to 28-30 ℃;
(2) standing and layering: standing for layering, centrifuging to discharge mother liquor, and retaining upper-layer crystals; then heating to 68-70 ℃ for complete melting;
(3) and (3) secondary alcohol water crystallization: and (3) adding the product obtained in the step (2), ethanol and water into a secondary crystallization kettle, starting stirring, heating to 68-70 ℃, cooling to 58-60 ℃ at the rate of 4 ℃ per hour, adding powdery seed crystals into the crystallization kettle, quickly crystallizing, preserving heat for 1.8-2.2 hours, cooling to 48-50 ℃ at the temperature of 2 ℃ per hour, cooling to 23-25 ℃ at the temperature of 5 ℃ per hour, allowing the materials to pass through a self-discharging centrifuge, realizing quick separation, and allowing the solid to enter a drying and packaging system to obtain the BHT.
2. The method of claim 1, wherein the method comprises the following steps: crude BHT in step (1): water: the mass ratio of sodium chloride is 1:0.5: (0.005-0.025).
3. The method of claim 1, wherein the method comprises the following steps: and (3) standing and layering for 25-35min in the step (2).
4. The method of claim 1, wherein the method comprises the following steps: the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in the layered mother liquor of the lower layer in the step (2) is below 40%, and the mass fraction of 2, 6-di-tert-butyl-4-methylphenol in crystals of the upper layer is above 99.0%.
5. The method of claim 4, wherein the method comprises the following steps: and (3) directly packaging the layered lower-layer mother liquor obtained in the step (2) for sale, and taking the packaged lower-layer mother liquor as one of raw materials of the antioxidant BHA.
6. The method of claim 1, wherein the method comprises the following steps: in the step (3), the stirring speed is 50-60 r/min.
7. The method of claim 1, wherein the method comprises the following steps: the mass ratio of the product obtained in the step (2) in the step (3) to ethanol to water is 1: 0.3:0.1.
8. The method of claim 1, wherein the method comprises the following steps: the mass fraction of the 2, 6-di-tert-butyl-4-methylphenol in the BHT refined product in the step (3) is more than 99.99%.
9. The method of claim 1, wherein the method comprises the following steps: in the step (3), the powder seed crystal is BHT with the mass fraction of more than 99.5%, and the adding amount of the powder seed crystal accounts for 0.01-0.02% of the mass of the crude BHT product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111233634A (en) * | 2020-02-29 | 2020-06-05 | 陕西宝塔山新材料有限公司 | Method for controlling antioxidant BHT crystallization by program forced cooling |
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| CN1931813A (en) * | 2006-07-15 | 2007-03-21 | 孟祥儒 | Production process of antioxidant 2,6-di-tert-butyl-4-methy phenol |
| CN103694085A (en) * | 2013-12-31 | 2014-04-02 | 江苏迈达投资发展股份有限公司 | Crystallization method of high-purity antioxidant BHT (butylated hydroxytoluene) |
| CN107522597A (en) * | 2016-06-21 | 2017-12-29 | 宁夏海诚电化信息科技有限公司 | A kind of secondary crystallization process of the methylphenol alkane production procedure of 2,6 di-t-butyl 4 |
-
2019
- 2019-10-31 CN CN201911049559.2A patent/CN110759815A/en active Pending
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111233634A (en) * | 2020-02-29 | 2020-06-05 | 陕西宝塔山新材料有限公司 | Method for controlling antioxidant BHT crystallization by program forced cooling |
| CN111233634B (en) * | 2020-02-29 | 2022-10-18 | 陕西宝塔山新材料有限公司 | Method for controlling antioxidant BHT crystallization by program forced cooling |
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