CN113264830A - Preparation method of phenolic ester type antioxidant - Google Patents
Preparation method of phenolic ester type antioxidant Download PDFInfo
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- CN113264830A CN113264830A CN202110585959.6A CN202110585959A CN113264830A CN 113264830 A CN113264830 A CN 113264830A CN 202110585959 A CN202110585959 A CN 202110585959A CN 113264830 A CN113264830 A CN 113264830A
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- reaction
- butyl
- hydroxyphenyl
- tert
- propionate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/76—Esters containing free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
Abstract
The invention discloses a preparation method of a phenolic ester antioxidant, which comprises the following steps: carrying out ester exchange reaction on 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctyl alcohol under the catalytic action of zinc acetate to obtain isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate; wherein the molar ratio of the 3, 5-methyl ester to the isooctyl alcohol is 0.9: 1.2-1.0: 1.2; the mass of the zinc acetate is 0.04-0.55 percent of that of the 3, 5-methyl ester; the reaction temperature of the ester exchange reaction is 172-178 ℃, the reaction time is 6.5-11.5 hours, and the gradient pressure is reduced from the vacuum degree of-0.02 MPa to-0.1 MPa in the reaction process; and adding a refrigerant after the ester exchange reaction is finished, standing at a low temperature, and performing centrifugal operation after the standing is finished to obtain the phenol ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) isooctyl propionate. By adopting the technical scheme of the invention, the prepared product has high purity, high yield, transparent appearance and strong oxidation resistance, and simultaneously, no waste water is generated, thereby being beneficial to environmental protection.
Description
Technical Field
The invention relates to the technical field of oxidant preparation, in particular to a preparation method of a phenolic ester type antioxidant.
Background
Isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate is a commonly used phenolic ester type antioxidant. The lubricating oil has the characteristics of good thermal stability, outstanding oxidation resistance under high temperature, good oil solubility, good compatibility with other additives, no ash and the like, and can be widely used in industrial lubricating oil such as various high-grade internal combustion engine lubricating oil, heat conducting oil, high-temperature chain oil, hydraulic oil, gear oil, steam turbine oil and the like, various lubricating grease and fuel oil.
Various methods for preparing isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate are available. However, in the conventional preparation method, for example, in U.S. Pat. No. 5,5892097, ester exchange reaction between 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctanol is disclosed by using organic tin as a catalyst, the reaction is easy to proceed, but the tin catalyst is not easy to remove, the appearance of the product is turbid due to residue in the product, and the tin catalyst has adverse effect on the environment.
For example, U.S. Pat. No. 4,4716244 discloses a method for transesterification of methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate and isooctanol under reduced pressure with zinc acetate as catalyst, wherein the reaction temperature is controlled at 190 deg.C, but the method does not adopt any method to remove the catalyst, so that the product has turbid appearance, and precipitates are generated after long-term standing.
For example, chinese patent CN1364753A discloses that zinc acetate is used as a catalyst, and 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and excess isooctyl alcohol are subjected to ester exchange reaction under normal pressure to obtain yellow transparent liquid, the product yield is 95% at most, and the product purity is 99.13% at most. The method needs acid washing, water washing and other steps for removing the catalyst at the later stage, generates a large amount of waste water, is not beneficial to environmental protection, and obtains a finished product with a darker color, a lower product yield, a lower product purity and a poorer oxidation resistance.
For example, Chinese patent CN110168508A discloses that aluminum isopropoxide is used as a catalyst, methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate and excess isooctanol are subjected to ester exchange reaction to obtain a water sample transparent liquid, and the product yield is up to 98.6%. The method for removing the catalyst at the later stage needs the steps of adding acid, removing water, filtering and the like, generates acidic wastewater, is not beneficial to environmental protection, and has the advantages of low product yield, low product purity and poor oxidation resistance.
Disclosure of Invention
Aiming at the problems, the invention provides a preparation method of a phenolic ester antioxidant, which comprises the steps of carrying out ester exchange reaction on 3, 5-di-tert-butyl-4-hydroxy phenyl methyl propionate and isooctyl alcohol through the catalytic action of zinc acetate to obtain the phenolic ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxy phenyl) isooctyl propionate, wherein the prepared product has high purity, high yield, transparent appearance and strong oxidation resistance, does not generate waste water, and is favorable for protecting the environment.
In order to achieve the above object, the present invention provides a method for preparing a phenolic ester antioxidant, comprising: carrying out ester exchange reaction on 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctyl alcohol under the catalytic action of zinc acetate to obtain isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate; the molar ratio of the methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate to the isooctyl alcohol is 0.9: 1.2-1.0: 1.2; the mass of the zinc acetate is 0.04-0.55% of that of the 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate; the reaction temperature of the ester exchange reaction is 172-178 ℃, the reaction time is 6.5-11.5 hours, and the gradient pressure reduction is carried out from the vacuum degree of-0.02 MPa to-0.1 MPa in the reaction process; and adding a refrigerant after the ester exchange reaction is finished, standing at a low temperature, and performing centrifugal operation after the standing is finished to obtain the phenol ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) isooctyl propionate.
In the above technical scheme, preferably, the molar ratio of the methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate to the isooctanol is 1: 1.
In the above technical solution, preferably, the refrigerant is dry ice or liquid nitrogen.
In the above technical solution, preferably, a flask equipped with a mechanical stirrer, a thermometer and a nitrogen inlet is used as the reaction vessel for the transesterification reaction, the mechanical stirrer is used for stirring during the reaction, the thermometer is used for controlling the reaction temperature of the transesterification reaction, and the refrigerant is input through the nitrogen inlet.
In the above technical scheme, preferably, a refrigerant is added after the transesterification reaction is finished, so that the reactant is kept standing at a low temperature of 0-10 ℃ for 1-5 hours.
In the above technical solution, preferably, after the low temperature standing after the ester exchange reaction is finished, the centrifugal operation is performed at a rotation speed of 200-700 rpm/sec.
In the above technical solution, preferably, the rotation speed of the centrifugal operation is 300-.
Compared with the prior art, the invention has the beneficial effects that: the ester exchange reaction is carried out on the 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctyl alcohol under the catalysis of zinc acetate to obtain the phenolic ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) isooctyl propionate, and the prepared product has high purity, high yield, transparent appearance, strong oxidation resistance, no waste water and environmental protection.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention is described in further detail below:
the preparation method of the phenolic ester antioxidant provided by the invention comprises the following steps: carrying out ester exchange reaction on 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctyl alcohol under the catalytic action of zinc acetate to obtain isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate; the molar ratio of the methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate to the isooctyl alcohol is 0.9: 1.2-1.0: 1.2; the mass of the zinc acetate is 0.04-0.55 percent of that of the 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate; the reaction temperature of the ester exchange reaction is 172-178 ℃, the reaction time is 6.5-11.5 hours, and the gradient pressure is reduced from the vacuum degree of-0.02 MPa to-0.1 MPa in the reaction process; adding a refrigerant after the ester exchange reaction is finished, standing at a low temperature, and performing centrifugal operation after the standing is finished to obtain the colorless and transparent phenolic ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) isooctyl propionate.
In the embodiment, 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctyl alcohol are subjected to ester exchange reaction under the catalytic action of zinc acetate to obtain phenolic ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) isooctyl propionate, and the prepared product has high purity, high yield, transparent appearance and strong oxidation resistance, does not generate waste water and is favorable for protecting the environment.
Specifically, under the catalytic action of a catalyst zinc acetate, methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate (hereinafter referred to as 3, 5-methyl ester) and isooctyl alcohol are subjected to ester exchange reaction, and the reaction equation is as follows:
compared with the prior art, the preparation method solves the problem of turbid product appearance caused by residual catalyst, does not need acid washing and water washing, does not generate waste water, is favorable for protecting the environment, does not need to add excessive isooctanol, and has high product yield, high effective content and strong oxidation resistance.
In the above examples, the molar ratio of methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate to isooctanol is preferably 1: 1.
In the above embodiment, preferably, the refrigerant is dry ice or liquid nitrogen.
In the above-mentioned examples, it is preferable that a flask equipped with a mechanical stirrer, a thermometer and a nitrogen inlet is used as the reaction vessel for the transesterification reaction, the mechanical stirrer is used for stirring during the reaction, the thermometer is used for controlling the reaction temperature of the transesterification reaction, and the nitrogen inlet is used for introducing a refrigerant.
In the above embodiment, preferably, after the transesterification reaction is completed, a refrigerant is added to keep the reactant at 0-10 ℃ and standing at a low temperature for 1-5 hours.
In the above embodiment, preferably, after the low temperature standing after the ester exchange reaction is finished, the centrifugation operation is performed at a rotation speed of 200-700 rpm.
In the above embodiment, the rotation speed of the centrifugal operation is preferably 300-.
The preparation of the phenolic ester antioxidant according to the above examples is further illustrated in the following examples during the practice.
The first embodiment is as follows:
146.2g (0.5mol) of 3, 5-methyl ester, 65.16g (0.5mol) of isooctanol and 0.731g of zinc acetate are added into a 500mL four-neck flask with a mechanical stirring, a thermometer, a distillation condenser and a nitrogen inlet, the temperature is gradually raised to 173 ℃ under the protection of nitrogen, the temperature is kept for reaction for 8 hours, the vacuum degree is-0.02 MPa for 2 hours before the temperature is kept for reaction, the vacuum degree is-0.05 MPa for 2-4 hours after the temperature is kept for reaction, the vacuum degree is-0.07 MPa for 4-6 hours after the temperature is kept for reaction, and the vacuum degree is-0.1 MPa for 6-8 hours after the temperature is kept for reaction. And adding dry ice after the heat preservation reaction is finished, standing for 2 hours at the temperature of 5 ℃, and centrifuging for 1 hour after the standing is finished, wherein the rotating speed is 350 r/s. Finally, 210.09g of colorless transparent liquid is obtained, namely the product. The product yield is 99.40 percent, and the product purity is 99.60 percent.
Example two:
146.2g (0.5mol) of 3, 5-methyl ester, 65.16g (0.5mol) of isooctanol and 0.731g of zinc acetate are added into a 500mL four-mouth flask with a mechanical stirring, a thermometer, a distillation condenser and a nitrogen inlet, the temperature is gradually raised to 175 ℃ under the protection of nitrogen, the reaction is carried out for 8 hours under heat preservation, the vacuum degree is-0.02 MPa for 2 hours before the reaction is carried out for heat preservation, the vacuum degree is-0.04 MPa for 2-4 hours after the reaction is carried out for heat preservation, the vacuum degree is-0.06 MPa for 4-6 hours after the reaction is carried out for heat preservation, and the vacuum degree is-0.1 MPa for 6-8 hours after the reaction is carried out for heat preservation. And adding dry ice after the heat preservation reaction is finished, standing for 2 hours at the temperature of 2 ℃, and centrifuging for 1 hour after the standing is finished, wherein the rotating speed is 350 r/s. Finally 210.79g of colorless transparent liquid is obtained, namely the product. The product yield is 99.50 percent, and the product purity is 99.70 percent.
Example three:
146.2g (0.5mol) of 3, 5-methyl ester, 65.16g (0.5mol) of isooctanol and 0.731g of zinc acetate are added into a 500mL four-neck flask with a mechanical stirring, a thermometer, a distillation condenser and a nitrogen inlet, the temperature is gradually raised to 177 ℃ under the protection of nitrogen, the temperature is kept for reaction for 10 hours, the vacuum degree is-0.02 MPa for 2 hours before the temperature is kept for reaction, the vacuum degree is-0.04 MPa for 2-5 hours after the temperature is kept for reaction, the vacuum degree is-0.08 MPa for 5-8 hours after the temperature is kept for reaction, and the vacuum degree is-0.1 MPa for 8-10 hours after the temperature is kept for reaction. And adding liquid nitrogen after the heat preservation reaction is finished, standing for 4 hours at the temperature of 3 ℃, and centrifuging for 1 hour after the standing is finished, wherein the rotating speed is 400 r/s. Finally 210.51g of colorless transparent liquid is obtained, namely the product. The product yield is 99.60 percent, and the product purity is 99.80 percent.
Further, a yellow transparent liquid was prepared according to the preparation method of comparative example one, using U.S. Pat. No. 4,4716244 in the background art as comparative example one.
Taking Chinese patent CN1364753A in the background technology as a second comparative example, the yellow transparent liquid is prepared according to the preparation method of the second comparative example, the product yield is 95%, and the product purity is 99.24%.
Taking Chinese patent CN110168508A in the background technology as a third comparative example, the preparation method of the third comparative example is adopted to prepare the water sample transparent liquid, the product yield is 98.6%, and the product purity is 98.9%.
Specifically, the products prepared in the third example and the first comparative example are placed at-10 ℃ for 15 days, so that the product prepared in the third example is colorless and transparent in appearance, and the product prepared in the first comparative example is yellow and turbid, which indicates that the product prepared by the method of the invention is colorless and transparent in appearance and is not turbid after being placed for a long time, and solves the problem of turbid appearance in the prior art. The results are shown in the following table.
Sample (I) | 10 ℃ below zero/1 day | 10 ℃ below zero/15 days |
EXAMPLE three products | Colorless and transparent | Colorless and transparent |
Comparative example A product | Yellow transparent and bright | Yellow turbidity |
Specifically, the oxidation resistance of the product is tested in the examples and the comparative examples, and the oxidation induction period of SH/T0719-2002 PDSC is used for testing, wherein 150N of plastic is used as the base oil, the addition amount is 0.5%, and the test results of the oxidation resistance are as follows:
sample (I) | Product yield% | Product purity% | Adding the amount of | Oxidative induction period, min |
EXAMPLE III | 99.60 | 99.80 | 0.5 | 25 |
Comparative example II | 95.00 | 99.23 | 0.5 | 20 |
Comparative example III | 98.60 | 98.90 | 0.5 | 17 |
As can be seen from the above table, the product prepared by the method for preparing a phenolic ester antioxidant of the present invention has the highest product yield, the highest product purity, the longest oxidation induction period, and the strongest antioxidant ability, compared to the comparative examples.
In addition, in the preparation method, isooctyl alcohol is not excessive, so that raw materials are saved; no waste water is generated, which is beneficial to environmental protection.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A preparation method of a phenolic ester antioxidant is characterized by comprising the following steps:
carrying out ester exchange reaction on 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate and isooctyl alcohol under the catalytic action of zinc acetate to obtain isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate;
the molar ratio of the methyl 3, 5-di-tert-butyl-4-hydroxyphenyl propionate to the isooctyl alcohol is 0.9: 1.2-1.0: 1.2;
the mass of the zinc acetate is 0.04-0.55% of that of the 3, 5-di-tert-butyl-4-hydroxyphenyl methyl propionate;
the reaction temperature of the ester exchange reaction is 172-178 ℃, the reaction time is 6.5-11.5 hours, and the gradient pressure reduction is carried out from the vacuum degree of-0.02 MPa to-0.1 MPa in the reaction process;
and adding a refrigerant after the ester exchange reaction is finished, standing at a low temperature, and performing centrifugal operation after the standing is finished to obtain the phenol ester antioxidant beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) isooctyl propionate.
2. The method for producing a phenol ester type antioxidant according to claim 1, wherein the molar ratio of the methyl 3, 5-di-t-butyl-4-hydroxyphenyl propionate to the isooctyl alcohol is 1: 1.
3. The method for preparing a phenolic ester antioxidant as claimed in claim 1, wherein the refrigerant is dry ice or liquid nitrogen.
4. The method of claim 3, wherein the transesterification reaction is carried out in a flask equipped with a mechanical stirrer, a thermometer and a nitrogen inlet, the mechanical stirrer is used for stirring during the reaction, the thermometer is used for controlling the reaction temperature of the transesterification reaction, and the nitrogen inlet is used for introducing the refrigerant.
5. The method for preparing a phenolic ester antioxidant as claimed in claim 1, wherein a refrigerant is added after the transesterification reaction is finished, so that the reactants are kept standing at a low temperature of 0-10 ℃ for 1-5 hours.
6. The method for preparing a phenolic ester antioxidant as claimed in claim 5, wherein the centrifugation is performed at 200-700 rpm/sec after the low temperature standing after the transesterification reaction.
7. The method for preparing a phenolic ester antioxidant as claimed in claim 6 wherein the rotation speed of the centrifugation operation is 300-400 rpm/sec.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN116332757A (en) * | 2023-03-10 | 2023-06-27 | 南雄志一精细化工有限公司 | Preparation method of liquid hindered phenol antioxidant |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4529809A (en) * | 1983-08-29 | 1985-07-16 | General Electric Company | Method for production of aryl substituted esters |
JP2001011021A (en) * | 1999-07-01 | 2001-01-16 | Yoshitomi Fine Chemicals Ltd | Sterically hindered hydroxyphenylcarboxylic acid ester compound, its production and removal of organic tin compound |
US20050192455A1 (en) * | 2004-02-27 | 2005-09-01 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
US20070060768A1 (en) * | 2003-10-10 | 2007-03-15 | Oxeno Olefinchemie Bmbh | Method for producing benzoic acid esters |
CN102030647A (en) * | 2010-11-05 | 2011-04-27 | 山东省临沂市三丰化工有限公司 | Clean production method for preparing liquid antioxidant |
CN107954863A (en) * | 2017-12-13 | 2018-04-24 | 新乡市瑞丰新材料股份有限公司 | The preparation method of phenolic ester type antioxidant |
CN111484432A (en) * | 2020-05-13 | 2020-08-04 | 新乡市瑞丰新材料股份有限公司 | Preparation method of thioether type hindered phenol antioxidant |
-
2021
- 2021-05-27 CN CN202110585959.6A patent/CN113264830A/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4529809A (en) * | 1983-08-29 | 1985-07-16 | General Electric Company | Method for production of aryl substituted esters |
JP2001011021A (en) * | 1999-07-01 | 2001-01-16 | Yoshitomi Fine Chemicals Ltd | Sterically hindered hydroxyphenylcarboxylic acid ester compound, its production and removal of organic tin compound |
US20070060768A1 (en) * | 2003-10-10 | 2007-03-15 | Oxeno Olefinchemie Bmbh | Method for producing benzoic acid esters |
US20050192455A1 (en) * | 2004-02-27 | 2005-09-01 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
CN102030647A (en) * | 2010-11-05 | 2011-04-27 | 山东省临沂市三丰化工有限公司 | Clean production method for preparing liquid antioxidant |
CN107954863A (en) * | 2017-12-13 | 2018-04-24 | 新乡市瑞丰新材料股份有限公司 | The preparation method of phenolic ester type antioxidant |
CN111484432A (en) * | 2020-05-13 | 2020-08-04 | 新乡市瑞丰新材料股份有限公司 | Preparation method of thioether type hindered phenol antioxidant |
Non-Patent Citations (1)
Title |
---|
王彦军: "从巯基乙酸异辛酯釜底残液中回收异辛醇的工艺研究", 《有色矿冶》, vol. 22, no. 6, pages 60 - 61 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116332757A (en) * | 2023-03-10 | 2023-06-27 | 南雄志一精细化工有限公司 | Preparation method of liquid hindered phenol antioxidant |
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