CN108084025A - A kind of preparation method of 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkyl alcohol ester - Google Patents
A kind of preparation method of 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkyl alcohol ester Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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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
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Abstract
The present invention provides one kind 3 (3,5 di-t-butyl, 4 hydroxy phenyl) propionic acid alkyl alcohol ester preparation method, belong to technical field of organic synthesis, the present invention will 2,6 DI-tert-butylphenol compounds, potassium tert-butoxide and t-butanol solution mix after be heated to reflux obtaining after mixed liquor mix with methyl acrylate after progress addition reaction obtain addition reaction liquid；Ester exchange reaction is carried out after addition reaction liquid is directly mixed with alkylol and obtains 3 (3,5 di-t-butyl, 4 hydroxy phenyl) propionic acid alkyl alcohol esters, alkylol C8~C16Linear chain or branch chain saturated monohydroxy alcohol.The present invention selects co-catalysis agent of the alkali metal compound as two-step reaction, addition reaction liquid directly carries out ester exchange reaction with alkylol without separation and is made 3 (3,5 di-t-butyl, 4 hydroxy phenyl) propionic acid alkyl alcohol ester, improve the preparation efficiency and yield of 3 (3,5 di-t-butyl, 4 hydroxy phenyl) propionic acid alkyl alcohol esters.
Description
Technical field
The present invention relates to technical field of organic synthesis, more particularly to a kind of 3- (3,5- di-tert-butyl-hydroxy phenyl) third
The preparation method of dialkylaminobenzoic acid alcohol ester.
Background technology
With the fast development of the high-end equipment manufacture in China, in numerous technical fields such as aerospace, automobile, ship
The lubricating oil of equal demand environment-friendly type inoxidizability and high temperature resistance.Antioxidant be in lubricating oil main additive it
One, mainly including phenol type antioxidant, amine type antioxidant, sulphur phosphorous antioxidant.It is reported that the antioxidant 2,6- of conventional amount maximum
Di-tert-butyl-4-methy phenol (BHT) gradually subtracts because of the discoloration problem under high volatile and higher processing temperature, demand
Few, and the demand of hindered phenol antioxygen will be increased with average annual 6% speed, wherein antioxidant 1076,1010 etc. are predominantly
Position.
Chinese patent CN105348103A reports a kind of method with new titanium-containing catalyst synthesis antioxidant 1076, by
2,6- phenol and methyl esters carry out addition reaction and 3,5- esters are made, then carry out ester exchange reaction generation antioxygen by 3,5- esters and 16 carbon alcohol
Agent 1076, being finally recrystallized to give product needs first to separate the addition compound product 3 that the first stage is prepared, 5- esters, then carries out ester
Exchange reaction.
The content of the invention
In view of this, present invention aims at provide a kind of 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkylol
The preparation method of ester, the present invention select co-catalysis agent of the potassium tert-butoxide as its two-step reaction, the addition that addition reaction obtains
Reaction solution directly carries out ester exchange reaction with alkylol without separation and 3- is made
(3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester improves 3- (3,5- di-t-butyl -4- hydroxy benzenes
Base) propionic acid alkyl alcohol ester preparation efficiency, while there is higher yield.
In order to realize foregoing invention purpose, the present invention provides following technical scheme：
The present invention provides a kind of preparation method of 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester, including
Following steps：
1) it is heated to reflux after mixing 2,6- DI-tert-butylphenol compounds, potassium tert-butoxide and t-butanol solution in nitrogen atmosphere,
Obtain mixed liquor；
2) addition reaction is carried out after the mixed liquor that the step 1) obtains is mixed with methyl acrylate, obtains addition reaction
Liquid；
3) the addition reaction liquid that the step 2) obtains directly with alkylol is mixed and carries out ester exchange reaction, obtain 3-
(3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkyl alcohol ester；The alkylol is C8~C16Straight_chain single fatty alcohols or branch
Chain saturated monohydroxy alcohol.
Preferably, the temperature being heated to reflux in the step 1) is 75~85 DEG C, the time being heated to reflux for 20~
30min。
Preferably, potassium tert-butoxide described in the step 1) is the 5%~10% of 2,6- DI-tert-butylphenol compounds quality.
Preferably, the temperature of addition reaction is 100~120 DEG C in the step 2), and the time of addition reaction is 2~4h.
Preferably, the molar ratio of 2,6- DI-tert-butylphenol compounds and methyl acrylate is 1.1 in the step 2)：1~1.8：
1。
Preferably, in the step 3) temperature of ester exchange reaction for 120~140 DEG C, time of ester exchange reaction for 2~
4h。
Preferably, the molar ratio of alkylol and 2,6- DI-tert-butylphenol compounds is 0.55 in the step 3)：1~0.9：1.
Preferably, the ester exchange reaction liquid for obtaining the ester exchange reaction is further included in the step 3) successively through cold
But, washing, extraction and crystallisation by cooling, obtain 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester.
Preferably, the extraction is absolute ethyl alcohol with extract liquor.
Advantageous effects：The present invention provides a kind of 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkyl alcohol esters
Preparation method, the present invention select co-catalysis agent of the potassium tert-butoxide as its two-step reaction, the addition that addition reaction obtains is anti-
Liquid is answered directly to carry out ester exchange reaction with alkylol without separation, 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkane is made
Base alcohol ester, improves the preparation efficiency of 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester, while has higher
Yield.Embodiment statistics indicate that, preparation method 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl provided by the invention
The yield of alcohol ester is up to more than 90%.
Description of the drawings
Fig. 1 is the infrared spectrogram of 3- in embodiment 1 (3,5- di-tert-butyl-hydroxy phenyls) propionic acid hexadecane alcohol ester；
Fig. 2 is that lubricating base oils add 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid hexadecane alcohol ester in embodiment 2
Thermal analysis curue after antioxidant；
Fig. 3 is the fortune that the lubricating base oils of antioxidant are added in embodiment 3 and are not added at 40 DEG C of the base oil of antioxidant
Kinetic viscosity variation diagram；
Fig. 4 is the fortune that the lubricating base oils of antioxidant are added in embodiment 3 and are not added at 100 DEG C of the base oil of antioxidant
Kinetic viscosity variation diagram；
Fig. 5 is the infrared spectrogram of 3- in embodiment 4 (3,5- di-tert-butyl-hydroxy phenyls) propionic acid dodecane alcohol ester；
Fig. 6 is the infrared spectrogram of 3- in embodiment 5 (3,5- di-tert-butyl-hydroxy phenyls) propionic acid dodecane alcohol ester.
Specific embodiment
The present invention provides a kind of preparation method of 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester, including
Following steps：
1) it is heated to reflux after mixing 2,6- DI-tert-butylphenol compounds, potassium tert-butoxide and t-butanol solution in nitrogen atmosphere,
Obtain mixed liquor；
2) addition reaction is carried out after the mixed liquor that the step 1) obtains is mixed with methyl acrylate, obtains addition reaction
Liquid；
3) the addition reaction liquid that the step 2) obtains directly with alkylol is mixed and carries out ester exchange reaction, obtain 3-
(3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkyl alcohol ester；The alkylol is C8~C16Straight_chain single fatty alcohols or branch
Chain saturated monohydroxy alcohol.
The present invention heats back after mixing 2,6 di t butyl phenol, potassium tert-butoxide and t-butanol solution in nitrogen atmosphere
Stream, obtains mixed liquor.
In the present invention, the temperature being heated to reflux is preferably 75~85 DEG C, more preferably 80 DEG C；It is described to be heated to reflux
Time be preferably 20~30min, more preferably 22~25min.
In the present invention, the potassium tert-butoxide is the 5%~10% of 2,6- DI-tert-butylphenol compounds quality.
The present invention is to 2,6 di t butyl phenol, potassium tert-butoxide and the method for t-butanol solution mixing after fusing without spy
It is different to limit, hybrid mode well known to those skilled in the art is selected, specifically, the present invention is preferably by 2,6- di-tert-butyls
Phenol, which is warming up to 80 DEG C, makes it be mixed again with potassium tert-butoxide and the tert-butyl alcohol after melting.
In the present invention, it is that several reactants come into full contact with by being heated to reflux effect, while potassium tert-butoxide and 2,6- bis-
Tert-butyl phenol can react, and generate 2,6- di-tert-butylphenol potassium.
After obtaining mixed liquor, the present invention carries out addition reaction after obtained mixed liquor is mixed with methyl acrylate, obtains
Addition reaction liquid.
In the present invention, the temperature of the addition reaction is preferably 100~120 DEG C, more preferably 105~115 DEG C；It is described
The time of addition reaction is preferably 2~4h, more preferably 2.5~4h.
It is mixed again with methyl acrylate in the present invention, it is preferred to which the mixed liquor is warming up to after addition reaction required temperature
It closes.The present invention is not particularly limited heating rate, selects heating rate well known to those skilled in the art.
In the present invention, the molar ratio of 2, the 6- DI-tert-butylphenol compounds and methyl acrylate is preferably 1.1：1~1.8：
1, more preferably 1.3：1~1.6：1.
In the present invention, it is preferred to which the methyl acrylate is added drop-wise in mixed liquor, the present invention is to the rate of the dropwise addition
It is not particularly limited, selects rate of addition well known to those skilled in the art.
After obtaining addition reaction liquid, it is anti-that obtained addition reaction liquid is directly mixed progress transesterification by the present invention with alkylol
Should, obtain 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester；The alkylol is C8~C16Linear chain or branch chain
Saturated monohydroxy alcohol.
Obtained addition reaction liquid directly with alkylol is mixed progress ester exchange reaction and obtains ester exchange reaction by the present invention
Liquid.The alkylol is C8~C16Linear chain or branch chain saturated monohydroxy alcohol, be preferably C12~C16Linear chain or branch chain saturation unitary
Alcohol, more preferably dodecyl alcohol, cetyl alcohol.
In the present invention, the temperature of the ester exchange reaction is preferably 120~140 DEG C, more preferably 125~135 DEG C；Institute
The time for stating ester exchange reaction is preferably 2~4h, more preferably 2.5~3.5h.
In the present invention, it is preferred to progress is mixed with alkylol again after addition reaction liquid is warming up to esterification exchange reaction temperature
Ester exchange reaction.The present invention is not particularly limited heating rate, selects heating rate well known to those skilled in the art.
In the present invention, the molar ratio of the alkylol and 2,6- DI-tert-butylphenol compounds is preferably 0.55：1~0.9：1, more
Preferably 0.6：1~0.8：1.
The present invention is not particularly limited the hybrid mode of addition reaction liquid and alkylol, selects those skilled in the art ripe
The hybrid mode known.In the present invention, it is preferred to alkylol is slowly dropped in addition reaction liquid.In the present invention, institute
It is preferably to be added portionwise to state alkylol.The present invention is not particularly limited the lot number being added portionwise and interval, selects this field skill
Lot number known to art personnel and interval.
In the present invention, the principle of the addition reaction and ester exchange reaction is shown below：
CnH2n+1OH is C8~C16Straight or branched alkyl alcohol.
After obtaining ester exchange reaction liquid, the present invention is preferably by ester exchange reaction liquid successively through cooling down, washing, extracting, cooling down
Crystallization, obtains 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester.
In the present invention, the temperature after cooling is preferably room temperature.
In the present invention, the extractant of the extraction is preferably ethyl alcohol.
The present invention selects those skilled in the art to cooling down, washing, extracting and the method for crystallisation by cooling is not particularly limited
Well known method.
With reference to embodiment to 3- provided by the invention (3,5- di-tert-butyl-hydroxy phenyls) propionic acid alkyl alcohol ester
Preparation method is described in detail, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1
In a nitrogen atmosphere, 2, the 6- DI-tert-butylphenol compounds of 0.05mol are added to and are equipped with thermometer, dropping funel and cold
In the three-necked flask of solidifying pipe, being warming up to 80 DEG C dissolves it；After with 8mL t-butanol solutions, potassium tert-butoxide 0.55g is dissolved, pour into
In three-necked flask.Mixed solution is warming up to 80 DEG C, back flow reaction 20 minutes, solution gradually becomes light green；Solution is heated up
To 120 DEG C, methyl acrylate 4.08mL is slowly added dropwise, be stirred to react 3 it is small when after, solution is in faint yellow；Continue to heat up solution
To 130 DEG C, hexadecanol 6.76g is slowly added portionwise, stir and react 3 it is small when after stop；Reaction product is cooled to room temperature, is passed through
Washing is crossed, is layered, takes upper solution；It is dissolved again with absolute ethyl alcohol and extracts upper solution, gone through supercooling ice-water bath is cold, it is quiet
Put, crystallize, filter out crystal just target product, yield is up to 91%, conversion ratio 94%.Its infrared spectrum as shown in Figure 1, its
Under characterize data figure：
3644.43cm-1Belong to the stretching vibration peak of phenolic hydroxyl group, 2849.42cm-1With 2954.82cm-1Belong to methyl
Stretching vibration absworption peak, 2918.42cm-1Belong to the stretching vibration absworption peak of methylene, 1732cm-1Nearby belong to C=
The stretching vibration absworption peak of O, 1472.08cm-1With 1463.05cm-1Belong to the bending vibration absworption peak of methyl, 1425.84cm-1Belong to the vibration absorption peak of phenyl ring, 1230.08cm-1Belong to the vibration absorption peak of C-O on phenol, 1170.63cm-1With
1143.21cm-1Belong to the vibration absorption peak of ester group C-O, 745.46cm-1Belong to the neck disubstituted-CH in position on phenyl ring3Bending is shaken
Dynamic characteristic peak, 719.45cm-1Belong to multiple-CH2Bending vibration characteristic peak.
Above-mentioned characterize data meets the official of target product 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid hexadecane alcohol ester
Characteristic peak can be rolled into a ball.
Embodiment 2
In a nitrogen atmosphere, 2, the 6- DI-tert-butylphenol compounds of 0.05mol are added to and are equipped with thermometer, dropping funel and cold
In the three-necked flask of solidifying pipe, being warming up to 80 DEG C dissolves it；After with 8mL t-butanol solutions, potassium tert-butoxide 0.55g is dissolved, pour into
In three-necked flask, mixed solution is warming up to 80 DEG C, back flow reaction 20 minutes, solution gradually becomes light green；Solution is heated up
To 110 DEG C, methacrylate 4.08mL is slowly added dropwise, be stirred to react 2 it is small when after, solution is in faint yellow；Continue to heat up solution
To 140 DEG C, hexadecanol 6.76g is slowly added portionwise, stir and react 2 it is small when after stop.Reaction product is cooled to room temperature, is passed through
Washing is crossed, is layered, takes upper solution.It is dissolved again with absolute ethyl alcohol and extracts upper solution.It through supercooling, stands, crystallizes, filtering
Go out crystal and just obtain target product 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid hexadecane alcohol ester.Yield is converted up to 92%
Rate 96%.
The content for being pressed 1w% is added in No. 1427 lubricating base oils TMPTO, using Pressurized Differential Scanning Calorimeter
(PDSC) heat analysis is carried out to the lubricating oil for adding in antioxidant, the results are shown in Figure 2, as shown in Figure 2 the starting of the lubricating oil
Oxidizing temperature is 183 DEG C, this improves 20 than not adding No. 1427 lubricating base oils TMPTO initial oxidation temperatures of antioxidant
℃.As it can be seen that product 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid hexadecane alcohol ester prepared by this method can be obviously improved profit
The antioxygenic property of lubricating oil.
Embodiment 3
In a nitrogen atmosphere, 2, the 6- DI-tert-butylphenol compounds of 0.05mol are added to and are equipped with thermometer, dropping funel and cold
In the three-necked flask of solidifying pipe, being warming up to 80 DEG C dissolves it.After with 8mL t-butanol solutions, potassium tert-butoxide 0.55g is dissolved, pour into
In three-necked flask.Mixed solution is warming up to 80 DEG C, back flow reaction 20 minutes, solution gradually becomes light green.Solution is heated up
To 110 DEG C, methacrylate 4.08mL is slowly added dropwise, be stirred to react 2 it is small when after, solution is in faint yellow；Continue to heat up solution
To 140 DEG C, hexadecanol 6.76g is slowly added portionwise, stir and react 2 it is small when after stop.Reaction product is cooled to room temperature, is passed through
Washing is crossed, is layered, takes upper solution.It is dissolved again with absolute ethyl alcohol and extracts upper solution.It through supercooling, stands, crystallizes, filtering
Go out crystal and just obtain target product 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid hexadecane alcohol ester.Yield is converted up to 91%
Rate 94%.
The content for being pressed 1w% is added in No. 1427 lubricating base oils TMPTO, and than less adding antioxidant and addition
Under antioxidant, the kinematic viscosity variation tendency of lubricating oil, result such as Fig. 3 and Fig. 4 after oven aging experiments at 135 DEG C of constant temperature
It is shown.By thermal oxide 480 it is small when, add antioxidant lubricating base oils move at 40 DEG C and 100 DEG C ratio of viscosities do not add
52% and 59% are reduced during antioxidant respectively.It can be seen that this antioxidant plays an important role of centainly to improve lubricating oil viscosity-temperature performance.
Embodiment 4
In a nitrogen atmosphere, 2, the 6- DI-tert-butylphenol compounds of 0.05mol are added to and are equipped with thermometer, dropping funel and cold
In the three-necked flask of solidifying pipe, being warming up to 80 DEG C dissolves it.After with 8mL t-butanol solutions, potassium tert-butoxide 0.7g is dissolved, pour into
In three-necked flask.Mixed solution is warming up to 80 DEG C, back flow reaction 20 minutes, solution gradually becomes green.Solution is warming up to
110 DEG C, methacrylate 4.08mL is slowly added dropwise, be stirred to react 2.5 it is small when after, solution is in faint yellow；Continue to heat up solution
To 130 DEG C, lauryl alcohol 5.68mL is slowly added portionwise, stir and react 2.5 it is small when after stop.Reaction product is cooled to room
Temperature, by washing, layering takes upper solution.It is dissolved again with absolute ethyl alcohol and extracts upper solution.It through supercooling, stands, knot
Crystalline substance filters out crystal and just obtains target product.Yield is up to 90%, conversion ratio 95%.Fig. 5 is the infrared spectrogram of target product,
It is as follows that it analyzes data：
3649.73cm-1Belong to the stretching vibration peak of phenolic hydroxyl group, 2849.47cm-1With 2955.3cm-1Belong to methyl
Stretching vibration absworption peak, 2918.01cm-1Belong to the stretching vibration absworption peak of methylene, 1732cm-1Nearby belong to C=O
Stretching vibration absworption peak, 1472.10cm-1With 1463.09cm-1Belong to the bending vibration absworption peak of methyl, 1425.94cm-1
Belong to the vibration absorption peak of phenyl ring, 1230.08cm-1Belong to the vibration absorption peak of C-O on phenol, 745.68cm-1It belongs to
The disubstituted CH in position is led on phenyl ring3Bending vibration characteristic peak, 719.54cm-1Belong to multiple-CH2Bending vibration characteristic peak.
The functional group of above-mentioned data fit target product 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid dodecane alcohol ester
Characteristic peak.
Embodiment 5
In a nitrogen atmosphere, 2, the 6- DI-tert-butylphenol compounds of 0.05mol are added to and are equipped with thermometer, dropping funel and cold
In the three-necked flask of solidifying pipe, being warming up to 80 DEG C dissolves it.After with 10mL t-butanol solutions, potassium tert-butoxide 0.8g is dissolved, pour into
In three-necked flask.Mixed solution is warming up to 80 DEG C, back flow reaction 30 minutes, solution gradually becomes green.Solution is warming up to
120 DEG C, methacrylate 4.08mL is slowly added dropwise, be stirred to react 4 it is small when after, solution is in faint yellow；Continue solution being warming up to
140 DEG C, lauryl alcohol 9.09mL is slowly added portionwise, stir and react 3 it is small when after stop.Reaction product is cooled to room temperature, is passed through
Washing is crossed, is layered, takes upper solution.It is dissolved again with absolute ethyl alcohol and extracts upper solution.It through supercooling, stands, crystallizes, filtering
Go out crystal and just obtain target product.Yield is up to 90%, conversion ratio 95%.Fig. 6 is the infrared spectrogram of target product, analyzes number
According to as follows：
3644.19cm-1Belong to the stretching vibration peak of phenolic hydroxyl group, 2849.42cm-1With 2955.59cm-1Belong to methyl
Stretching vibration absworption peak, 2918.67cm-1Belong to the stretching vibration absworption peak of methylene, 1732cm-1Nearby belong to C=
The stretching vibration weak absorbing peak of O, 1425.86cm-1Belong to the vibration absorption peak of phenyl ring, 1230.14cm-1It belongs on phenol
The vibration absorption peak of C-O, 745.55cm-1Belong to the neck disubstituted-CH in position on phenyl ring3Bending vibration characteristic peak.
The functional group of above-mentioned data fit target product 3- (3,5- di-tert-butyl-hydroxy phenyls) propionic acid dodecane alcohol ester
Characteristic peak.
The above of the invention is only the preferred embodiment of the present invention, it is noted that for the common of the art
For technical staff, various improvements and modifications may be made without departing from the principle of the present invention, these are improved and profit
Decorations also should be regarded as protection scope of the present invention.
Claims (9)
1. a kind of preparation method of 3- (3,5- di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester, comprises the following steps：
1) it is heated to reflux after mixing 2,6- DI-tert-butylphenol compounds, potassium tert-butoxide and the tert-butyl alcohol, obtains mixed solution；
2) addition reaction is carried out after the mixed solution that the step 1) obtains is mixed with methyl acrylate, obtains addition reaction
Liquid；
3) the addition reaction liquid that the step 2) obtains directly with alkylol is mixed and carries out ester exchange reaction, obtain 3- (3,5-
Di-tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester；The alkylol is C8~C16Straight_chain single fatty alcohols or branch saturation
Monohydric alcohol.
2. preparation method according to claim 1, which is characterized in that the temperature being heated to reflux in the step 1) for 75~
85 DEG C, the time being heated to reflux is 20~30min.
3. preparation method according to claim 1, which is characterized in that potassium tert-butoxide described in the step 1) is 2,6- bis-
The 5%~10% of tert-butyl phenol quality.
4. preparation method according to claim 1, which is characterized in that the temperature of addition reaction is 100 in the step 2)
~120 DEG C, the time of addition reaction is 2~4h.
5. the preparation method according to claim 1 or 4, which is characterized in that 2,6-, bis- uncles in the step 2) mixed solution
The molar ratio of butylphenol and methyl acrylate is 1.1：1~1.8：1.
6. preparation method according to claim 1, which is characterized in that the temperature of ester exchange reaction is in the step 3)
120~140 DEG C, the time of ester exchange reaction is 2~4h.
7. the preparation method according to claim 1 or 6, which is characterized in that bis- uncle of alkylol and 2,6- in the step 3)
The molar ratio of butylphenol is 0.55：1~0.9：1.
8. preparation method according to claim 1, which is characterized in that further included after the step 3) ester exchange reaction：It will
The ester exchange reaction liquid that the ester exchange reaction obtains through cooling down, washing, extracting and crystallisation by cooling, obtains 3- (3,5- bis- successively
Tert-butyl-hydroxy phenyl) propionic acid alkyl alcohol ester.
9. preparation method according to claim 8, which is characterized in that the extraction is absolute ethyl alcohol with extractant.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111205905A (en) * | 2020-01-31 | 2020-05-29 | 武汉材料保护研究所有限公司 | Polyphenol antioxidant for ester lubricating oil and preparation method thereof |
| CN111321028A (en) * | 2018-12-13 | 2020-06-23 | 中国石油天然气股份有限公司 | Ashless antioxidant lubricating oil additive, compound lubricating oil additive and lubricating oil composition containing additives |
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| CN111205905A (en) * | 2020-01-31 | 2020-05-29 | 武汉材料保护研究所有限公司 | Polyphenol antioxidant for ester lubricating oil and preparation method thereof |
| CN111205905B (en) * | 2020-01-31 | 2022-04-15 | 武汉材料保护研究所有限公司 | Polyphenol antioxidant for ester lubricating oil and preparation method thereof |
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