CN105886128A - Method for producing pesticide green solvent from rice bran oil - Google Patents
Method for producing pesticide green solvent from rice bran oil Download PDFInfo
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- CN105886128A CN105886128A CN201610261189.9A CN201610261189A CN105886128A CN 105886128 A CN105886128 A CN 105886128A CN 201610261189 A CN201610261189 A CN 201610261189A CN 105886128 A CN105886128 A CN 105886128A
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- Prior art keywords
- esterification
- reaction
- testa oryzae
- solvent
- methanol
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for producing a pesticide green solvent from rice bran oil, comprising the following steps: (1), by using acidic catalytic esterification and synchronous water removal technology, reducing generated water of a reaction system, promoting forward reaction and improving esterification yield; (2), controlling flow, adding sodium hydroxide alcoholic solution to prevent saponification due to excessive local alkali concentration, reduce material loss and improve product quality; (3), post-treating a product: removing residual methanol solvent from an oil layer by flashing, and distilling in a vacuum distiller to obtain the green solvent. The method has the advantages that methanol for use herein is used as a material for esterification of the green solvent, the methanol is a reactant and is also a diluent and reflux solvent, water is carried in the esterification process by refluxing and circulating, generated water of the reaction system is decreased, and product esterification rate is greatly increased. The technology used herein is a low-cost green integrated novel technology for producing green solvents from biomass.
Description
Technical field
The present invention relates to a kind of Testa oryzae oil produce pesticide green solvent method, be specifically related to
Testa oryzae oil is catalytic material esterification, synchronizes except the series technique such as water, continuous ester interchange produces green
The method of solvent.
Background technology
Testa oryzae is the part (oil-containing 9%-22%) that in the grain of rice, oil content is the highest.Therefore be potential
Large oil sources.China is Oryza sativa L. big producing country of the world, and yield accounts for the 1/3 of world wide production, therefore
Testa oryzae oil raw material is the abundantest.China's Oryza glutinosa annual production about 200,000,000 tons, and secondary as paddy processing
The annual production of product Testa oryzae is more than 18,000,000 tons.At present, a small amount of rice is utilized except south China
Bran carries outside oil, and remaining is all as low-quality feed applications.The Testa oryzae oil almost all in northeast
Do not utilize, greatly waste resource.
The fatty acid methyl ester produced for raw material by esterification, ester exchange reaction with Testa oryzae oil, it is
A kind of mono alkyl ester of long-chain fatty acid, fatty acid methyl ester possesses the advantage of general industry solvent,
And the advantage with many uniquenesses: the strongest solvability；The most nontoxic；3. peace is used
Entirely, it is not required to special Storage Measures；The most biodegradable；5. environment protection health.Therefore, fat
Acid methyl ester is very suitable for replacing organic solvent in pesticide.But it derives from biomass, it is that one can
Biodegradable green solvent, the invention discloses a kind of Testa oryzae oil is that catalytic material is esterified, together
Step produces the pesticide side of green solvent fatty acid methyl ester except the series technique such as water, continuous ester interchange
Method.
The patent that presently disclosed relevant Testa oryzae oil utilizes is few in number, and it is green molten to be esterified preparation
The patent of agent is the most rare.Several and the present invention closely-related technical side is briefly described below
Method.
1, patent CN101319167 relates to high-acid value rice bran oil esterification depickling process, this technique
Can be good at solving refining yield this problem low.High-acid value rice bran oil esterification depickling process includes
Oils and fats pretreatment, i.e. two steps, one is degumming, and two is decolouring, and must decolour after decolouring thing,
Then carrying out esterification deacidification, obtain low acid value Testa oryzae oil, acid number is 5-7mgKOH/g.
2, patent CN102453613A relates to the side of a kind of producing diesel oil by esterification deacidification of rice bran oil
Method.The method utilizes high acid value Rice bran crude oil, and employing zinc oxide is as catalyst, by esterification
Deacidification, becomes biodiesel raw material, Testa oryzae oil acid number can be down to from 38.14mg/g by its deacidification
5.17mg/g。
3, patent CN103131540A provides a kind of based on ionic liquid-catalyzed high acid value Testa oryzae
The method of oil preparation biodiesel, with peracid value rice bran oil and methanol as raw material, described high acid value
Containing free fatty and triglyceride in Testa oryzae oil；Described triglyceride and methanol carry out ester friendship
Changing reaction, described fatty acid and methanol carry out esterification, and described ester exchange reaction and esterification
Reaction is carried out with biodiesel synthesis in same reactor, and described catalyst is sulfonic group merit
Quaternary ammonium salt ionic liquid can be changed, to rustless steel almost without corrosion.
4, patent CN104450209A discloses one solid superacid as catalyst Testa oryzae oil crude oil
The method of deacidification value, adds glycerol and solid superacid as catalyst in the Testa oryzae oil crude oil of high acid value
Agent, heated and stirred, the water that evacuation elimination reaction generates, catalysis is recovered by filtration after having reacted
Agent i.e. obtains low-acid value rice bran oil.
5, patent CN104823969A discloses a kind of fatty acid methyl ester as environmentally friendly solvent in agriculture
Exploitation application in medicine preparation, replaces the most a large amount of high poison solvent used with this.The invention belongs to
In technical field of pesticide, directly add in pesticidal preparations produces as environmentally friendly solvent, its function
Be dissolve, dispersion pesticide active ingredient, then with other additive compounds, by stirring mixing,
Shear or sand milling, prepare qualified pesticidal preparations product, it is adaptable to mineral sources pesticide, life
All Pesticidal products such as thing source pesticide, chemical synthetic pesticide.
6, patent CN104818125A discloses a kind of fatty acid methyl with waste grease as raw material
The preparation method of ester.Key step includes raw oil pretreatment, esterification workshop section, ester exchange, thick
Methyl ester rectification, washing, glycerol purify and reclaim.The utilization rate of the raw oil of the present invention is high, to former
The material miscellaneous content of profit does not limit.Thick Arrcostab is improved by adding boric acid at distillation system
Rectification efficiency.On the premise of meeting ingredient requirement, through the process of above-mentioned technique.
7, the synthetic method of a patent CN102703227A fatty acid methyl ester, belongs to and organises
The synthesis technical field of ester type compound in, with natural oil and methanol as raw material, in catalysis
Carry out ester exchange reaction under the effect of agent and prepare fatty acid methyl ester, be then demultiplex out crude glycerine, so
Rear redistillation goes out unnecessary methanol, and natural oil is Oleum Cocois, palm-kernel oil or Petiolus Trachycarpi oil etc..
Catalyst is Feldalat NM or potassium hydroxide, and the addition of catalyst is oils and fats and methanol gross mass hundred
The 0.5～1.0% of proportion by subtraction, oils and fats can be 1: 3.0～1: 8.0 with the mol ratio of methanol.
Up to the present, relate to method and have solid super strong high acid value Esterification, ionic liquid-catalyzed
Rice bran oil esterification, soda acid combine transesterification technique etc., and solid acid catalyst overcomes traditional handicraft
The problem that the difficulty of sulphuric acid removes, but solid acid catalysis esterification there is also certain shortcoming, as urged
Agent is easily poisoned, regeneration difficulty, and ionic liquid-catalyzed method mild condition contaminative is little, but price
Costliness, it is most common method that soda acid combines transesterification process, but intermediate treatment process
Loaded down with trivial details, wastewater flow rate is big, deals with easy saponification improperly.
Therefore this patent proposition one utilizes acid catalyzed esterification, synchronizes except water, continuous base catalysis ester
Switching technology, utilizes and synchronizes, except water avoids the problem of local saponification, to eliminate existing Acid-Base
The product last handling process that the centre of two-step process is loaded down with trivial details, reduces the production of fatty acid methyl ester
Cost.
Summary of the invention
It is an object of the present invention to provide a kind of method that Testa oryzae oil produces pesticide green solvent.
Technical scheme includes the following:
(1) acid catalyzed esterification
First by Testa oryzae oil and methanol in molar ratio 1: 4～1: 16 ratio add reaction unit,
Add Testa oryzae oil quality 0.1～2.5% concentrated sulphuric acid make catalyst, esterification at 40～70 DEG C
1～4 hour；Can produce water in esterification process, during back flow reaction, solvent serves as water entrainer effect,
Being brought into by moisture in system in exsiccator and be dried, the solvent refluxing being dried enters reaction system
Continue cycling through band water, by synchronizing water removal techniques, reduce the generation water of reaction system, promote ester
Change reaction, improve productivity；
(2) base-catalyzed transesterification
The product being esterified in (1) is entered transesterification device, controls flow 5～30mL/min
Add a certain amount of sodium hydroxide alcoholic solution, it is to avoid locally saponification, control 50～70 DEG C of temperature of reaction
Degree, ester exchange reaction 1～3 hours, it is achieved transesterification reaction；
(3) product post processing
Product after transesterification reaction in (2) is entered separatory tank, and upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until side-product glycerol content therein, whole technique without
Disposal of pollutants.
The present invention is technically characterized in that employing acid catalyzed esterification, synchronizes water removal techniques, reduces
The generation water of reaction system, promotes that reaction forward is carried out, improves esterification yied.
The present invention is technically characterized in that control flow adds sodium hydroxide alcoholic solution, it is possible to keep away
Exempt from local base concentration too high, cause saponification phenomenon, reduce significant loss, improve product quality.
The advance of this patent is:
(1) this patent methanol as the raw material of the esterification of green solvent, methanol is
Reactant, is again diluent and reflux solvent, reflux cycle band water in esterification reaction process, with
Step water removal techniques, reduces the generation water of reaction system, is greatly improved product ester rate.
(2) this patent is using sodium hydroxide alcoholic solution as the catalyst of base catalysis, controls flow
Add, both substantially increased ester exchange catalytic effect, avoid again saponification phenomenon, reduce raw material and damage
The loaded down with trivial details last handling process that mistake and saponification bring, improves product yield.
Detailed description of the invention
Below by detailed description of the invention, the present invention is described, but is not limited to this.
Embodiment 1
1, first by Testa oryzae oil and methanol in molar ratio 1: 6 ratio add reaction unit, in advance
Heat is to 40 DEG C, and the concentrated sulphuric acid adding Testa oryzae oil quality 0.5% makees catalyst, temperature reaction system
To 60 DEG C, esterification 3 hours at 60 DEG C；
2, the product being esterified in 1 is entered transesterification device, control 10mL/min flow and add
Enter a certain amount of sodium hydroxide alcoholic solution, control reaction temperature about 60 DEG C, ester exchange reaction 2
Hour, it is achieved transesterification reaction；
3, product after transesterification reaction in 2 being entered separatory tank, upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until glycerol content therein, whole technique is pollution-free row
Put.
Embodiment 2
1, first by Testa oryzae oil and methanol in molar ratio 1: 6 ratio add reaction unit, in advance
Heat is to 40 DEG C, and the concentrated sulphuric acid adding Testa oryzae oil quality 0.8% makees catalyst, temperature reaction system
To 60 DEG C, esterification 3 hours at 60 DEG C；
2, the product being esterified in 1 is entered transesterification device, control 10mL/min flow and add
Enter a certain amount of sodium hydroxide alcoholic solution, control reaction temperature about 60 DEG C, ester exchange reaction 2
Hour, it is achieved transesterification reaction；
3, product after transesterification reaction in 2 being entered separatory tank, upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until glycerol content therein, whole technique is pollution-free row
Put.
Embodiment 3
1, first by Testa oryzae oil and methanol in molar ratio 1: 8 ratio add reaction unit, in advance
Heat is to 40 DEG C, and the concentrated sulphuric acid adding Testa oryzae oil quality 0.5% makees catalyst, temperature reaction system
To 60 DEG C, esterification 3 hours at 60 DEG C；
2, the product being esterified in 1 is entered transesterification device, control 10mL/min flow and add
Enter a certain amount of sodium hydroxide alcoholic solution, control reaction temperature about 60 DEG C, ester exchange reaction 2
Hour, it is achieved transesterification reaction；
3, product after transesterification reaction in 2 being entered separatory tank, upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until glycerol content therein, whole technique is pollution-free row
Put.
Embodiment 4
1, first by Testa oryzae oil and methanol in molar ratio 1: 8 ratio add reaction unit, in advance
Heat is to 40 DEG C, and the concentrated sulphuric acid adding Testa oryzae oil quality 0.8% makees catalyst, temperature reaction system
To 60 DEG C, esterification 3 hours at 60 DEG C；
2, the product being esterified in 1 is entered transesterification device, control 10mL/min flow and add
Enter a certain amount of sodium hydroxide alcoholic solution, control reaction temperature about 60 DEG C, ester exchange reaction 2
Hour, it is achieved transesterification reaction；
3, product after transesterification reaction in 2 being entered separatory tank, upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until glycerol content therein, whole technique is pollution-free row
Put.
Embodiment 5
1, first by Testa oryzae oil and methanol in molar ratio 1: 6 ratio add reaction unit, in advance
Heat is to 40 DEG C, and the concentrated sulphuric acid adding Testa oryzae oil quality 0.5% makees catalyst, temperature reaction system
To 60 DEG C, esterification 3 hours at 60 DEG C；
2, the product being esterified in 1 is entered transesterification device, control 8mL/min flow and add
Enter a certain amount of sodium hydroxide alcoholic solution, control reaction temperature about 60 DEG C, ester exchange reaction 2
Hour, it is achieved transesterification reaction；
3, product after transesterification reaction in 2 being entered separatory tank, upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until glycerol content therein, whole technique is pollution-free row
Put.
Embodiment 6
1, first by Testa oryzae oil and methanol in molar ratio 1: 8 ratio add reaction unit, in advance
Heat is to 40 DEG C, and the concentrated sulphuric acid adding Testa oryzae oil quality 0.8% makees catalyst, temperature reaction system
To 60 DEG C, esterification 3 hours at 60 DEG C；
2, the product being esterified in 1 is entered transesterification device, control 8mL/min flow and add
Enter a certain amount of sodium hydroxide alcoholic solution, control reaction temperature about 60 DEG C, ester exchange reaction 2
Hour, it is achieved transesterification reaction；
3, product after transesterification reaction in 2 being entered separatory tank, upper strata oil reservoir takes off through flash distillation
Except residue methanol solvate, subsequently into water washing tank, enter back into vacuum distillation tower and carry out distilling green
Color solvent；Lower floor's washing layer enters digestion recycling can, and the hot water entrance water washing tank having reclaimed alcohol returns
With, reach the most afterwards to reclaim glycerol until glycerol content therein, whole technique is pollution-free row
Put.
Above content is that to combine concrete preferred implementation made for the present invention further in detail
Describe in detail bright, it is impossible to assert the present invention be embodied as be confined to these explanations.For this area
Those of ordinary skill for, can according to technical scheme, make corresponding change and
Substitute, and performance or purposes are identical, all should be considered as protection scope of the present invention.
Claims (6)
1. the method that Testa oryzae oil produces pesticide green solvent, it specifically comprises the following steps that
(1) acid catalyzed esterification
First by Testa oryzae oil and methanol in molar ratio 1: 4～1: 16 ratio add reaction unit, add Testa oryzae oil quality 0.1～2.5% concentrated sulphuric acid make catalyst, esterification 1～4 hours at 40～70 DEG C；Esterification process can produce water, during back flow reaction, solvent serves as water entrainer effect, moisture in system is brought in exsiccator and be dried, the solvent refluxing being dried enters reaction system and continues cycling through band water, by synchronizing water removal techniques, reduces the generation water of reaction system, promote esterification, improve productivity；
(2) base-catalyzed transesterification
The product being esterified in (1) is entered transesterification device, controls flow 5～30mL/min and add a certain amount of sodium hydroxide alcoholic solution, it is to avoid locally saponification, control 50～70 DEG C of temperature of reaction, ester exchange reaction 1～3 hours, it is achieved transesterification reaction；
(3) product post processing
Product after transesterification reaction in (2) is entered separatory tank, and upper strata oil reservoir, through flash distillation removing residue methanol solvate, subsequently into water washing tank, enters back into vacuum distillation tower and carries out distilling to obtain green solvent；Lower floor's washing layer enters digestion recycling can, and the hot water having reclaimed alcohol enters water washing tank reuse, reaches the most afterwards to reclaim glycerol, whole technique non-pollution discharge until glycerol content therein.
A kind of Testa oryzae oil the most as claimed in claim 1 produces the method for pesticide green solvent, it is characterised in that: described employing acid-catalyzed esterification reaction, the acid catalyst of employing is concentrated sulphuric acid, and the amount adding sulfuric acid catalyst is Testa oryzae oil quality 0.1～2.5%.
A kind of Testa oryzae oil the most as claimed in claim 1 produces the method for pesticide green solvent, it is characterised in that: described methanol is absolute methanol, Testa oryzae oil and the mol ratio 1: 4～1: 16 of methanol.
A kind of Testa oryzae oil the most as claimed in claim 1 produces the method for pesticide green solvent, it is characterised in that: described esterification temperature is 40～70 DEG C, and reaction time of esterification is 1～4 hour.
A kind of Testa oryzae oil the most as claimed in claim 1 produces the method for pesticide green solvent, it is characterized in that: the catalyst in base-catalyzed transesterification stage is sodium hydroxide alcoholic solution, the ester exchange stage is 5～30mL/min in order to avoid local saponification, the addition speed controlling of sodium hydroxide alcoholic solution.
A kind of Testa oryzae oil the most as claimed in claim 1 produces the method for pesticide green solvent, it is characterised in that: in the base-catalyzed transesterification stage, controlling reaction temperature is 50～70 DEG C, and the ester exchange reaction time is 1～3 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610261189.9A CN105886128A (en) | 2016-04-20 | 2016-04-20 | Method for producing pesticide green solvent from rice bran oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610261189.9A CN105886128A (en) | 2016-04-20 | 2016-04-20 | Method for producing pesticide green solvent from rice bran oil |
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| CN105886128A true CN105886128A (en) | 2016-08-24 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201610261189.9A Pending CN105886128A (en) | 2016-04-20 | 2016-04-20 | Method for producing pesticide green solvent from rice bran oil |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101020864A (en) * | 2007-03-22 | 2007-08-22 | 北京硕泰生物技术有限责任公司 | Stepped high valent acid vegetable oil catalyzing process for preparing fatty acid methyl ester |
| CN101392181A (en) * | 2008-11-04 | 2009-03-25 | 吉林大学 | Novel method for preparing biodiesel by in situ extraction of rice oil |
-
2016
- 2016-04-20 CN CN201610261189.9A patent/CN105886128A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101020864A (en) * | 2007-03-22 | 2007-08-22 | 北京硕泰生物技术有限责任公司 | Stepped high valent acid vegetable oil catalyzing process for preparing fatty acid methyl ester |
| CN101392181A (en) * | 2008-11-04 | 2009-03-25 | 吉林大学 | Novel method for preparing biodiesel by in situ extraction of rice oil |
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Application publication date: 20160824 |