CN110387002A - A kind of preparation of industrial oleic acid pour-point depressant and its application method - Google Patents
A kind of preparation of industrial oleic acid pour-point depressant and its application method Download PDFInfo
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- CN110387002A CN110387002A CN201810368528.2A CN201810368528A CN110387002A CN 110387002 A CN110387002 A CN 110387002A CN 201810368528 A CN201810368528 A CN 201810368528A CN 110387002 A CN110387002 A CN 110387002A
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- Prior art keywords
- oleic acid
- pour
- industrial oleic
- point depressant
- preparation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0028—Carboxylic acids; Their derivates
Abstract
The present invention discloses preparation and its application method of a kind of industrial oleic acid pour-point depressant, cause equimolar alhpa olefin, maleic anhydride polymerization reaction 2~8 hours with peroxide at 135~200 DEG C, polymerization reaction and dilution alhpa olefin maleic anhydride multipolymer are terminated with industrial oleic acid, and obtains acid value >=185mgKOH/g industrial oleic acid pour-point depressant.The pour-point depressant is used for industrial oleic acid, and the pour-point depressant can reduce the freezing point (congealing point) of industrial oleic acid, improve the low temperature flow of industrial oleic acid.
Description
Technical field
The present invention relates to the preparation of industrial oleic acid pour-point depressant and its application method, in particular to a kind of alhpa olefin maleic two
Acid anhydride copolymer preparation and its industrial oleic acid application method.
Background technique
Industrial oleic acid is C 18 unsaturated fatty acid, wherein the existing fatty acid for containing a unsaturated double-bond, also has and contain
The fatty acid of two unsaturated double-bonds, there are also a small amount of saturated fatty acids and greases.Commodity industrial oleic acid presses its congealing point (freezing point)
Height is generally divided into three kinds of high, medium and low congealing point, and congealing point is respectively no higher than 10 DEG C, 8 DEG C, 4 DEG C.Winter in southern area, gas
Temperature drops to 0~10 DEG C sometimes, these regional winter storage and transportations can be encountered using industrial oleic acid because oleic acid crystallizes precipitation or solidification
Oleic acid is caused to be difficult to the problem of flowing, there are two types of the means for solving the problems, such as this at present, and one is equipped with lagging facility, makes at oleic acid
On its cold point temperature；Second is that being lower than the oleic acid of environment temperature using congealing point, the former needs to increase equipment investment and energy consumption, after
Person needs using the higher low congealing point oleic acid of price.In existing technology, the way for reducing the congealing point of industrial oleic acid is to pass through
The method of freezing separation reduces saturated fatty acid, the fat content in oleic acid.CN104726204A discloses a kind of low congealing point
The production technology of oleic acid, the technique are to be delivered to industrial oleic acid in heating tank by pump heat, keep the temperature, and are then fed into freezing knot
It carries out in brilliant kettle repeatedly cooling down and being stirred continuously step by step, crystallizes the solid fat in industrial oleic acid, the fatty acid of high congealing point is from mixing
It closes and is constantly precipitated in object, mixture is filtered by diaphragm filter press, to obtain low congealing point oleic acid, the congealing point of oleic acid exists
8 DEG C hereinafter, oleic acid is in stable condition under lower temperature, phenomena such as being not in muddiness, be layered.US6342081B1 discloses one kind
The additive of fraction valenta value is reduced, which is the polymer of alhpa olefin and maleic anhydride, and wherein alhpa olefin is C16~
C18Alhpa olefin, the additive be used for distillate, be used for example as the turbidity removal agent of diesel oil.The author is once to the crystallization inhibitor of report, suppression
Brilliant agent, dispersing agent for wax carry out experimental study in industrial oleic acid, do not find its freezing point or low temperature flow to industrial oleic acid
There is substantive improvement.Currently, there is no makes industrial oleic acid have mobility in 0~10 DEG C of environment temperature, to industrial oleic acid
The additive that technical indicator has no adverse effects again.
How the prior art is improved, a kind of side of easily operated improvement industrial oleic acid low temperature mobility is provided
Method, and method has no adverse effects to the technical indicator of industrial oleic acid, is southern area industrial oleic acid storage and transportation and use occasion needs
The technical issues of solution.
Summary of the invention
The purpose of the present invention is, in storage and transportation and the freezing problem of use process, provide for southern area winter industrial oleic acid
A kind of preparation of industrial oleic acid pour-point depressant and its application method.
Technical solution:
A kind of preparation of industrial oleic acid pour-point depressant and its application method cause equimolar α with peroxide at 135~200 DEG C
Alkene, maleic anhydride polymerization reaction 2~8 hours terminate polymerization reaction and dilution alhpa olefin maleic acid with industrial oleic acid
Anhydride copolymer, and obtain acid value >=185mgKOH/g industrial oleic acid pour-point depressant.The pour-point depressant is for reducing industrial oleic acid
Freezing point, improves the low temperature flow of industrial oleic acid, and the pour-point depressant has no adverse effects to the technical indicator of industrial oleic acid.
A kind of preparation method of industrial oleic acid pour-point depressant, 135~200 DEG C with peroxide cause equimolar alhpa olefin,
Maleic anhydride polymerization reaction 2~8 hours, polymerization reaction was terminated with industrial oleic acid and dilution alhpa olefin maleic anhydride is total
Polymers, and obtain acid value >=185mgKOH/g industrial oleic acid pour-point depressant.
A kind of preparation method of industrial oleic acid pour-point depressant, the pour-point depressant are that copolymerization is single with alhpa olefin, maleic anhydride
The molar ratio of body, alhpa olefin and maleic anhydride is 1: 1.
A kind of preparation method of industrial oleic acid pour-point depressant, the alhpa olefin is C18~C28Alhpa olefin, and have following knot
Structure:
CH3(CnH2n)- CH=CH2
N=15~25
A kind of preparation method of industrial oleic acid pour-point depressant, the peroxide are the organic compound containing peroxy (- O-O -)
Object, the peroxide are not less than 1 hour in 120 DEG C of half-life period.
The molar ratio of a kind of preparation method of industrial oleic acid pour-point depressant, the peroxide and maleic anhydride is 1: 20
~1: 15, the peroxide was in 135~200 DEG C of initiation alhpa olefins, maleic anhydride polymerization reaction 2~8 hours.
A kind of preparation method of industrial oleic acid pour-point depressant terminates polymerization reaction and dilution alhpa olefin maleic with industrial oleic acid
The molar ratio of anhydride multipolymer, the industrial oleic acid and maleic anhydride is 1: 0.7~1: 0.3.
A kind of preparation method of industrial oleic acid pour-point depressant, 70 DEG C of the fusing point > of the alhpa olefin maleic anhydride multipolymer.
A kind of preparation method of industrial oleic acid pour-point depressant, acid value >=185mgKOH/g of the pour-point depressant.
A kind of application method of industrial oleic acid pour-point depressant: the pour-point depressant is being higher than 3 DEG C of industrial oleic acid freezing point or more
Temperature be added in industrial oleic acid, and be uniformly mixed, additive amount of the pour-point depressant in industrial oleic acid is industrial oleic acid weight
The 0.5~5% of amount.
The present invention has following advance: prepared by the method industrial oleic acid pour-point depressant and its application method can drop
The freezing point of low industrial oleic acid solves the problems, such as that industrial oleic acid can not flow in the winter of southern area because solidifying, pour-point depressant pair
The technical indicator of industrial oleic acid has no adverse effects, and present invention tool is easy to implement, has operability.
Specific embodiment
In order to make those skilled in the art more fully understand technical solution of the present invention, below by specific embodiment pair
The present invention is described in further detail.
The acid of the fusing point of alhpa olefin maleic anhydride multipolymer, the freezing point of industrial oleic acid and pour-point depressant in the present invention
The measuring method of value is as follows:
1, copolymer fusing point
By copolymer sample in 0~10 DEG C of cold water soaking be not less than 10 minutes, take out use filter paper suck dry moisture, then according to
Standard GB/T/T19466 measurement.
2, the freezing point of industrial oleic acid
It is measured according to standard GB/T/T 618.
3, the acid value of pour-point depressant
Measurement is provided according to the chapter 6 of standard GB/T/T 9104.
Method of the invention is specifically described below by way of specific embodiment.
Example 1
The preparation of industrial oleic acid pour-point depressant A.
C is added in four round flask20~C24108 grams of alhpa olefin, 32 grams of maleic anhydride, load onto blender, temperature
Degree meter, condenser pipe, belt switch charging hopper start stirring, when on temperature of charge with electric jacket by material heating fusing in flask
150~160 DEG C are risen to, starts that 2.8 grams of di-tert-butyl peroxide is added dropwise, the time for adding of di-tert-butyl peroxide is
3.5 hours, during dropwise addition, temperature of charge is controlled at 150~180 DEG C, after being added dropwise, continues to stir at 150~180 DEG C
0.5 hour, copolymer sample is taken, 173 grams of industrial oleic acids are then added and terminate polymerization reaction and dilution copolymer, after mixing evenly
Obtain industrial oleic acid pour-point depressant A.
Fusing point test is carried out to copolymer sample, fusing point is 90 DEG C.
Acid value measuring is carried out respectively to test industrial oleic acid sample, pour-point depressant A sample, industrial oleic acid acid value is
196.3mgKOH/g, pour-point depressant A acid value are 197.5mgKOH/g.
Comparative test industrial oleic acid and pour-point depressant A appearance, the two are suitable.
Example 2
The preparation of industrial oleic acid pour-point depressant B.
C is added in four round flask20~C28110 grams of alhpa olefin, 30.8 grams of maleic anhydride, load onto blender,
Thermometer, condenser pipe, belt switch charging hopper start stirring, work as temperature of charge with electric jacket by material heating fusing in flask
When rising to 155~170 DEG C, start that 2.7 grams of di-tert-butyl peroxide, the time for adding of di-tert-butyl peroxide is added dropwise
It is 4 hours, during dropwise addition, temperature of charge is controlled at 150~180 DEG C, after being added dropwise, continues to stir at 150~180 DEG C
0.5 hour, copolymer sample is taken, 170 grams of industrial oleic acids are then added, obtain industrial oleic acid pour-point depressant B after mixing evenly.
Fusing point test is carried out to copolymer sample, fusing point is 85 DEG C.
Acid value measuring is carried out respectively to test industrial oleic acid sample, pour-point depressant B sample, industrial oleic acid acid value is
196.3mgKOH/g, pour-point depressant B acid value are 197.0mgKOH/g.
Comparative test industrial oleic acid and pour-point depressant B appearance, the two are suitable.
Example 3
It adds the pour-point depressant A of the preparation of example 1 respectively in 15 DEG C of industrial oleic acids one, industrial oleic acid two, is uniformly mixed, measure work
The freezing point of industry oleic acid freezes industrial oleic acid 3 days in 6 DEG C, 3 DEG C of temperature, observes its mobility, test result is listed in table 1, table
2。
Application test of the 1 pour-point depressant A of table in industrial oleic acid one
Note: it is in discrete particles shape that crystallization, which is precipitated,
Application test of the 2 pour-point depressant A of table in industrial oleic acid two
Note: it is in discrete particles shape that crystallization, which is precipitated,
Table 1, table 2 in temperature higher than addition example 1 in 5 DEG C of its own freezing point temperature, 7 DEG C of industrial oleic acid the results show that make
Standby pour-point depressant A, can reduce the freezing point of industrial oleic acid, when pour-point depressant A additional amount is suitable, can make the solidification of industrial oleic acid
Point drops to 1 DEG C, 0 DEG C from 10 DEG C, 8 DEG C respectively, and freezing at 3 DEG C 3 days still has mobility.
Choose No. 1 sample, No. 5 samples carry out other index determinings of industrial oleic acid, be as a result listed in table 3.
Index variation of 3 industrial oleic acid of table before and after adding pour-point depressant A
| Sample number | Iodine number, gI2/100g | Saponification number, mgKOH/g | Acid value, mgKOH/g | Color (Fe-Co) |
| 1 | 119.6 | 199.2 | 196.3 | 2" |
| 5 | 119.1 | 199.8 | 196.9 | 2" |
Example 4
Pour-point depressant B prepared by example 2 is added in 12 DEG C of industrial oleic acid, is uniformly mixed, is measured the freezing point of industrial oleic acid, In
6 DEG C, freeze industrial oleic acid 3 days in 3 DEG C of temperature, observe its mobility, test result is listed in table 4.
Application test of the 4 pour-point depressant B of table in industrial oleic acid
Note: it is in discrete particles shape that crystallization, which is precipitated,
Test result is shown, pour point depression prepared by example 2 is added in the industrial oleic acid that temperature is higher than 4 DEG C of its own freezing point temperature
Agent B can significantly reduce the freezing point of industrial oleic acid, it is made to have mobility at a lower temperature.
Protection scope of the present invention is not limited only to technical solution disclosed in specific embodiment, and the foregoing is merely this hairs
Bright better embodiment, is not intended to limit the present invention, and any trickle amendment made by all technical solutions according to the present invention is equal
Replacement and improvement, all should be included in the scope of protection of the technical solution of the present invention.
Claims (15)
1. a kind of preparation method of industrial oleic acid pour-point depressant, which is characterized in that rubbed at 135~200 DEG C with peroxide initiation etc.
Your alhpa olefin, maleic anhydride polymerization reaction 2~8 hours terminate polymerization reaction and dilution alhpa olefin along fourth with industrial oleic acid
Enedioic acid anhydride copolymer.
2. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the pour-point depressant is with α
Alkene, maleic anhydride are comonomer.
3. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the alhpa olefin is C18
~C28Alhpa olefin.
4. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the alhpa olefin has
With flowering structure:
CH3(CnH2n)- CH=CH2
N=15~25.
5. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the alhpa olefin with it is suitable
The molar ratio of anhydride maleique is 1: 1.
6. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the peroxide is
Organic compound containing peroxy (- O-O -).
7. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the peroxide exists
120 DEG C of half-life period is not less than 1 hour.
8. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the peroxide with
The molar ratio of maleic anhydride is 1: 20~1: 15.
9. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the peroxide exists
135~200 DEG C of initiation alhpa olefins, maleic anhydride polymerization reaction 2~8 hours.
10. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that with industrial oleic acid end
Only polymerization reaction and dilution alhpa olefin maleic anhydride multipolymer.
11. polymerization reaction and dilution alhpa olefin maleic anhydride multipolymer are terminated with industrial oleic acid as claimed in claim 10,
It is characterized in that, the molar ratio of the industrial oleic acid and maleic anhydride is 1: 0.7~1: 0.3.
12. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the alhpa olefin is along fourth
70 DEG C of the fusing point > of enedioic acid anhydride copolymer.
13. a kind of preparation method of industrial oleic acid pour-point depressant as described in claim 1, which is characterized in that the pour-point depressant
Acid value >=185mgKOH/g.
14. a kind of application method of industrial oleic acid pour-point depressant, which is characterized in that the pour-point depressant is being higher than industrial oleic acid freezing point
3 DEG C or more of temperature is added in industrial oleic acid, and is uniformly mixed.
15. a kind of application method of industrial oleic acid pour-point depressant, which is characterized in that additive amount of the pour-point depressant in industrial oleic acid
It is the 0.5~5% of industrial oleic acid weight.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810368528.2A CN110387002A (en) | 2018-04-23 | 2018-04-23 | A kind of preparation of industrial oleic acid pour-point depressant and its application method |
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| CN201810368528.2A CN110387002A (en) | 2018-04-23 | 2018-04-23 | A kind of preparation of industrial oleic acid pour-point depressant and its application method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112280622A (en) * | 2020-11-03 | 2021-01-29 | 江西省天玉油脂有限公司 | Preparation method of low saturated acid and low cloud point oleic acid |
| CN112619901A (en) * | 2020-12-08 | 2021-04-09 | 北矿化学科技(沧州)有限公司 | Preparation method and application of modified oleic acid collecting agent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1064305A (en) * | 1992-04-15 | 1992-09-09 | 抚顺石油学院 | Lubricating oil, oil fuel and pour point depressant for crude oil |
| US6342081B1 (en) * | 1999-07-13 | 2002-01-29 | Equistar Chemicals, Lp | Cloud point depressants for middle distillate fuels |
| CN101812348A (en) * | 2010-05-21 | 2010-08-25 | 北京奥力助兴石化有限公司 | Diesel pour point depressant |
-
2018
- 2018-04-23 CN CN201810368528.2A patent/CN110387002A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1064305A (en) * | 1992-04-15 | 1992-09-09 | 抚顺石油学院 | Lubricating oil, oil fuel and pour point depressant for crude oil |
| US6342081B1 (en) * | 1999-07-13 | 2002-01-29 | Equistar Chemicals, Lp | Cloud point depressants for middle distillate fuels |
| CN101812348A (en) * | 2010-05-21 | 2010-08-25 | 北京奥力助兴石化有限公司 | Diesel pour point depressant |
Non-Patent Citations (1)
| Title |
|---|
| 陈旭堂等: "马来酸酐/α-烯烃二元共聚物及其酯化物对生物柴油降凝效果的研究", 《生物质化学工程》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112280622A (en) * | 2020-11-03 | 2021-01-29 | 江西省天玉油脂有限公司 | Preparation method of low saturated acid and low cloud point oleic acid |
| CN112619901A (en) * | 2020-12-08 | 2021-04-09 | 北矿化学科技(沧州)有限公司 | Preparation method and application of modified oleic acid collecting agent |
| CN112619901B (en) * | 2020-12-08 | 2023-05-02 | 北矿化学科技(沧州)有限公司 | Preparation method and application of modified oleic acid collector |
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Application publication date: 20191029 |