CN103642842A - Enzymatic synthetic method of novel oil condensate - Google Patents
Enzymatic synthetic method of novel oil condensate Download PDFInfo
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- CN103642842A CN103642842A CN201310644089.0A CN201310644089A CN103642842A CN 103642842 A CN103642842 A CN 103642842A CN 201310644089 A CN201310644089 A CN 201310644089A CN 103642842 A CN103642842 A CN 103642842A
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- oil
- fuel thickener
- oil condensate
- vinyl acetate
- lipase
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention relates to an enzymatic synthetic method of a novel oil condensate. The method comprises the following steps: (1) synthesis of an oil condensate: mixing sugar alcohol with a solvent, then, adding an alkyl donor, then, adding an enzyme catalyst and heating at constant temperature under stirring, and centrifugalizing to obtain dissolved liquor of the oil condensate, after filtering by a filter membrane, and rotatably evaporating to remove the solvent to obtain a white oil condensate coarse product; and (2) separation of the oil condensate: separating the white oil condensate crude product by a chromatographic column, and rotatably evaporating the effluent to remove the eluant to obtain the white powder, namely the target oil condensate. The method provided by the invention catalyzes efficiently by means of bio-enzymes, so that the method is simple to operate and environmental, and free from pollution. The oil condensate prepared can condense various oils and organic solvents, and is less in use level and quick in gelling speed. Meanwhile, waste of conventional oil condensates is overcome by using the oil condensate. The oil phase of the novel oil condensate gel is simply heated to be melted, so that the gel can be recycled.
Description
Technical field
The invention belongs to a kind of enzyme catalysis synthesis technology field of fuel thickener, particularly utilize the method for sugar alcohol synthetic fuel thickener under enzyme catalysis.
Background technology
In the last few years, frequently there is .2011 CNOOC Bohai Sea Gulf oil accident in marine oil spill pollution incident, and the marine site sea pollution that causes approximately 6200 square kilometres of Peng Lai 19-3 oil field periphery and northwestward areas thereof wherein 870 square kilometres of seawater is subject to severe contamination.When seawater petroleum class concentration is the highest, surpass 53 times of background values.Cophi Co., Ltd and CNOOC need pay 16.83 hundred million yuan for this reason, for Bohai Sea ecological construction and environment protection, the Bohai Sea, enter extra large petroleum-type pollution reduction, impaired ocean habitat rehabilitation etc.In addition also have a leakage of oil event being caused by oil well eruption that occurs in Gulf, bottom the offshore drilling platform " deep water local horizon " of sinking, oil well leakage of oil every day is up between 3.5 ten thousand barrels to 60,000 barrels.This pollution may cause the littoral 1000 miles of long wetlands in the Gulfian and seabeach to be ruined, fishery is impaired, fragile species extinction, to become the useless sea of a slice reaching the Gulfian in time of 10 years, the financial loss causing will, in hundreds billion of dollars, be called as " the leakage of oil disaster that peacetime (whole world) is the most serious ".The BP of British Petroleum Company p.l.c., except paying record-breaking 4,000,000,000 dollars of fine, also sets up 20,000,000,000 dollar pools, for compensating because of the impaired common people of Gulfian leakage of oil event livelihood for this reason.
Such leakage of oil event remains existing despite repeated prohibition in recent years, the marine ecology safety that not only caused huge financial loss but also serious threat, and its carcinogens is by concentrated accumulating in marine organism, the mankind's the health of also having given serious threat.Therefore, how to remove quickly and efficiently greasy dirt and become major issue urgently to be resolved hurrily.Obviously, we are necessary to find a kind of material that can control Oil spills and can recycle oil.Fuel thickener is a kind of promptly gelling marine oil overflow and make it to form solid-state or semi-solid state is block, floats on the material of the water surface, stops the further diffusion of oil spilling, is easy to recycle, and seldom causes secondary pollution, is therefore very potential oil-spill chemical.In the Chinese patent that is 00110988.X in applicant's patent No., introduced a kind of manufacture lipid acid poly-hydroxy metal complexes and done fuel thickener, although solidifying oily excellent performance, energy consumption is very high, and its optimal reaction temperature is 50-110 ℃.In the Chinese patent that is 200710018131.2 in applicant's patent No., disclose a kind of leather-solid waste that utilizes and prepared fuel thickener, the cheap wide material sources of raw material, but synthetic operation is complicated, and need to be to pretreatment.And take the waste residue of vegetable oil mill in the Chinese patent that is 92115113.6 in applicant's patent No., be the synthetic fuel thickener of raw material, for gel crude oil, after gelling, oil clot viscosity reaches more than 10 ten thousand mpas. but its gel time is long, and to lightweight oil DeGrain.Thereby the actual use of above three kinds of fuel thickeners is all restricted.
A kind of efficient and desirable jelling agent must meet following requirement: 1) can from water surrounding, selectively and efficiently make at ambient temperature oil reservoir generation gel; 2) be easy to synthetic and cost is lower; 3) environmentally friendly; 4) be easy to restore grease from gel; While 5) can recirculation and recycling.Here, we have proposed a kind of new both sexes jelling agent on the basis of the growth of natural sugar alcohol.These amphiprotic substances can play a part optionally curing in oil-water mixture to oil reservoir.They can meet above any requirement, for remedying of oil leakage, are therefore a kind of very promising candidate families.Utilize the oil phase of this fuel thickener gel to have thermal reversibility, by simple heating, its melten gel can be reduced, the pollution that not only solves oil spilling destroys problem, and facilitates recycling, has saved the energy, has reduced cost.There is very high use value.
In order to respond the requirement of national environmental protection, we combine the synthetic of this fuel thickener with enzyme catalysis, started a kind of green, efficient, the synthetic and separating technology of safety.In the preparation process of this fuel thickener, the high reactivity of enzyme and stability are to realize industrialized prerequisite and assurance, and are to realize the basis of the efficient preparation of fuel thickener with crucial based on novel fixation support and technology immobilized lipase.As far as is known, this aspect research, still in the starting stage, has the innovative of uniqueness.
Summary of the invention
The invention provides a kind of enzymatic synthesis method of novel fuel thickener, utilize the extensive glycitols existing of occurring in nature as substrate, with miscellaneous alkyl donor direct reaction, synthesize a kind of novel fuel thickener.This building-up reactions can utilize biological enzyme to carry out efficient catalytic, simple to operate, green non-pollution.The fuel thickener obtaining can solidify multiple oils and organic solvent, and consumption is few, and gelation rate is fast.Utilize this fuel thickener can overcome the wasting phenomenon existing while using traditional fuel thickener, thereby the oil phase of novel fuel thickener gel can be by simply adding hot melt adhesive recycling, save energy when reducing pollution, reduces costs simultaneously.
The present invention solves this technical problem adopted technical scheme:
An enzymatic synthesis method for novel fuel thickener, comprises the steps:
1) fuel thickener is synthetic: by sugar alcohol and solvent, then add alkyl donor, then add enzyme catalyst and under 30～50 ℃ of stirrings after thermostatically heating 24～48h, the centrifugal 5min of 6000～10000r/min, obtains the lysate of fuel thickener; After membrane filtration, rotary evaporation is removed solvent, obtains the thick product of white fuel thickener after filtration; Material proportion is mol ratio sugar alcohol: alkyl donor=1:1～4; Every 0.35g lipase adds 20～60ml solvent; Every 0.55g sugar alcohol adds the solvent of 30～50ml;
2) separation of fuel thickener: utilize the 200-300 order silica gel phase that fixes, the glass chromatography column separation and purification fuel thickener of 2.4 * 40cm, usining methyl alcohol and chloroform mixed solution, as eluent, the thick product of fuel thickener obtained above to be carried out to chromatography column separated; By the effluent liquid accessing below pillar, rotary evaporation is removed eluent wherein, obtains white powder and is target fuel thickener.
Described solvent is acetone or dimethyl formamide;
Described alkyl donor is 1,1-dimethoxy hexanaphthene, 2,2-dimethoxypropane or vinyl acetate;
Described sugar alcohol is specially N.F,USP MANNITOL, Sorbitol Powder, Xylitol or erythritol.
Described vinyl acetate is C
4above vinyl acetate and derivative thereof.
Described vinyl acetate is preferably vinyl butyrate, valeric acid vinyl acetate, sad vinyl acetate or capric acid vinyl acetate.
Described enzyme catalyst is specially the letter N435 (Novozymes435) of Novi, the letter TLIM (Novozymes TL IM) of Novi,
Antarctic candidia lipase A (Candida antarctica Lipase A, CALA), antarctic candidia lipase
B (Candida antarctica Lipase B, CALB), candiyeast subspecies lipase 99-125(Candida sp.99-125) or
Aspergillus oryzae lipase (Thermomyces Lanuginosus Lipase, TLL).
Described eluent is methyl alcohol and chloroform mixed solution, and volume ratio is methyl alcohol: chloroform=1:18～27.
Described filter membrane is the mixed cellulose ester microporous membrane in 0.45 μ m aperture.
The invention has the beneficial effects as follows: 1. the present invention is a kind of enzymatic synthesis method of novel fuel thickener, and substrate raw material is wide material sources not only, at occurring in nature, exist in a large number, and of a great variety, cheap.2. utilize biological enzyme to make catalyzer, reaction conditions is gentle, simple to operate, green non-pollution.3. the fuel thickener output that prepared by present method is high, solidifying oily superior performance, as fast in gelation rate (in 1-3min, can make oil phase reach the salvaged hardness of energy); Amount of gel few (gel 1L oil phase only needs the fuel thickener of about 10-39g); It is applied widely that (oil phase can be lightweight oil, also can be heavy oil and various organic solvent) 4. the solid oil phase of gel after salvaging, by simple direct heating (70-150 ℃), can recover by melten gel, reach the object of oil spilling recycling, in the time of save energy, also can reclaim fund, reduce costs.
Accompanying drawing explanation
Fig. 1 is 93# gasoline in embodiment 1, diesel oil, and sweet oil, edible soybean oil, the photo of toluene and water mixed liquid, wherein, Fig. 1 a) oil phase is 93# gasoline; Fig. 1 b) oil phase is diesel oil; Fig. 1 c) oil phase is sweet oil; Fig. 1 d) oil phase is edible soybean oil; Fig. 1 e) oil phase is toluene.
Fig. 2 adds the photo after fuel thickener 5min in embodiment 1 in different profit two-phases, and Fig. 2 a) oil phase is 93# gasoline; Fig. 2 b) oil phase is diesel oil; Fig. 2 c) oil phase is sweet oil; Fig. 2 d) oil phase is edible soybean oil; Fig. 2 e) oil phase is toluene.
Fig. 3 be in embodiment 1 by the photo being equipped with after the reversing of oil phase test tube after gel, Fig. 3 a) oil phase is 93# gasoline; Fig. 3 b) oil phase is diesel oil; Fig. 3 c) oil phase is sweet oil; Fig. 3 d) oil phase is edible soybean oil; Fig. 3 e) oil phase is toluene.
Embodiment
Example 1:
N.F,USP MANNITOL (0.55g) and acetone (40mL) are mixed, after vibration mixes, add sad vinyl acetate (1.54g, N.F,USP MANNITOL and sad vinyl acetate mol ratio are 1:3) vibration to mix.Add lipase-catalyzed dose (Novozymes435,0.35g).Reactant is placed in to 40 ℃ of thermostat water baths and heats, 200r/min stirs, simultaneously condensing reflux 48h.By reaction mixture 8000r/min centrifugation 5min on table model high speed centrifuge, obtain the lysate of fuel thickener, used the two-layer hybrid fabric ester micro-hole filtering film in 0.45 μ m aperture to filter, by the 70 ℃ of constant temperature rotary evaporations of solution after filtering, until acetone volatilization is clean, now in container, residual white mass is the thick product of fuel thickener.
Select a glass chromatography column that specification is 2.4cm * 40cm, using 45g200-300 order silica gel as stationary phase, (volume ratio is methyl alcohol: chloroform=1:18) as eluent for methyl alcohol and chloroform mixed solution, wet method is filled out post, for guaranteeing there is no bubble between silica gel, when will disposablely pour silica gel into during dress post, with the multi-direction chromatography column that knocks gently of rub bar, with the thick quartz sand of 1cm, cover silica gel upper strata, while preventing application of sample, destroy silicagel column structure.The thick product of fuel thickener obtained above is dissolved in to eluent, after drawing with suction pipe, along tube wall, injects post, normal pressure chromatographic separation.Below pillar, every 20ml accesses effluent liquid one time, and then rotary evaporation is removed eluent wherein, and the white powder obtaining is the fuel thickener after purification.As calculated, fuel thickener productive rate is theoretical yield 62%.
The performance study of fuel thickener:
1) get five glass test tubees, add respectively the aqueous solution of 2ml copper sulfate and the rotor that quality is 0.7g, in every test tube, add successively 1ml sweet oil, toluene, 93# gasoline, diesel oil and edible soybean oil.By glue head dropper difference, inject fuel thickener alcoholic solution (50mg/0.5ml ethanol) in two-phase interface place wherein, the test tube that overturns after the standing 5min of room temperature (25 ℃), observes the solidifying oily effect of fuel thickener to different organic liquids and grease, as Fig. 1～3.In Fig. 1 test tube, be the mixed solution of various oil phases and water, oil phase is positioned at upper strata.By left-to-right (test tube a～e) oil phase, be respectively 93# gasoline, diesel oil, sweet oil, edible soybean oil and toluene.Fig. 2 is the design sketch adding after fuel thickener 5min.All there is obvious gelatin phenomenon in 93# gasoline, diesel oil, sweet oil, edible soybean oil and toluene, become solid and be positioned at above water, during different oil phases there is volumetric expansion in various degree.Fig. 3 is by after 180 ° of test tube upsets, rotor and water be extrusion solid oil phase under action of gravity, it is indeformable and 93# gasoline, diesel oil, sweet oil, edible soybean oil and toluene after gel all has that enough hardness can be born the weight of 2.7g, when oil phase is because of gel in addition, volumetric expansion and tube wall are close to unlikely water leakage, and 5 kinds of oil phases of above result proof all meet the requirement of being salvaged by physics completely in 5min.
2) the solid oil phase of gel is immersed in to slowly heating (3 ℃/15s) in the middle of oil bath, the change of state of observing gel oil phase.Until the fusing of gel oil phase, Current Temperatures is the Gel-sol transition temperature of this gel oil phase.
3) by the solid oil phase refuse after gel, then add successively respectively the liquid oil phase that 0.05ml is identical, room temperature is standing, observes.If organic liquid and grease still solidify, repeat above-mentioned steps and test.Until oil phase resolidification not.Record total consumption of this oil phase now, thus calculate fuel thickener to this oil phase minimum gel strength (%wt/v, mg/100 μ l).
Example 2:
Example 1 N.F,USP MANNITOL and the mole dosage ratio of sad vinyl acetate are changed to 1:2, and temperature of reaction is 40 ℃, and other are synthetic and separation condition is constant, and now this fuel thickener productive rate is theoretical yield 53%.This fuel thickener is oily for solidifying Fructus oleae europaeae, toluene, 93# gasoline, the oil phases such as diesel oil and edible soybean oil also can obtain same effect.
Example 3
Guaranteeing that in example 1, N.F,USP MANNITOL is changed to 1:3 with the mole dosage ratio of sad vinyl acetate, is 45 ℃ by temperature of reaction transposing, according to the same terms is synthetic, all can obtain this fuel thickener with separated, and now productive rate is theoretical yield 65%.Use it for gel sweet oil, toluene, 93# gasoline, the oil phases such as diesel oil and edible soybean oil also can obtain same effect.
Example 4
Guaranteeing that in example 1, N.F,USP MANNITOL is changed to 1:3 with the mole dosage ratio of sad vinyl acetate, is 35 ℃ by temperature of reaction transposing, according to the same terms is synthetic, all can obtain this fuel thickener with separated, and now productive rate is theoretical yield 60%.Use it for gel sweet oil, toluene, 93# gasoline, the oil phases such as diesel oil and edible soybean oil also can obtain same effect.
Example 5:
Guarantee that in example 1, N.F,USP MANNITOL is changed to 1:3 with the mole dosage ratio of sad vinyl acetate, temperature of reaction is 40 ℃, and enzyme dosage is adjusted into 0.7g, and reaction 48h all can obtain this fuel thickener according to the same terms is synthetic with separated, and now productive rate is theoretical yield 73%.Use it for gel sweet oil, toluene, 93# gasoline, the oil phases such as diesel oil and edible soybean oil also can obtain same effect.
Example 6:
Guarantee that in example 1, N.F,USP MANNITOL is changed to 1:3 with the mole dosage ratio of sad vinyl acetate, temperature of reaction is 40 ℃, and enzyme dosage is adjusted into 0.7g, and reaction 24h all can obtain this fuel thickener according to the same terms is synthetic with separated, and now productive rate is theoretical yield 59%.Use it for gel sweet oil, toluene, 93# gasoline, the oil phases such as diesel oil and edible soybean oil also can obtain same effect.
Claims (6)
1. an enzymatic synthesis method for novel fuel thickener, is characterized by and comprise the steps:
1) fuel thickener is synthetic: by sugar alcohol and solvent, then add alkyl donor, then add biological enzyme agent and stir after lower thermostatically heating 24～48h in 30～50 ℃ of 200r/min, the centrifugal 5min of 6000～10000r/min, obtains the lysate of fuel thickener; After membrane filtration, rotary evaporation is removed solvent, obtains the thick product of white fuel thickener after filtration; Material proportion is mol ratio sugar alcohol: alkyl donor=1:1～4; Every 0.35g lipase adds 20～60ml solvent; Every 0.55g sugar alcohol adds the solvent of 30～50ml;
2) separation of fuel thickener: utilize the 200-300 order silica gel phase that fixes, the glass chromatography column separation and purification fuel thickener of 2.4 * 40cm, usining methyl alcohol and chloroform mixed solution, as eluent, the thick product of fuel thickener obtained above to be carried out to chromatography column separated; By the effluent liquid accessing below pillar, rotary evaporation is removed eluent wherein, obtains white powder and is target fuel thickener;
Described solvent is acetone or dimethyl formamide;
Described alkyl donor is 1,1-dimethoxy hexanaphthene, 2,2-dimethoxypropane or vinyl acetate;
Described sugar alcohol is specially N.F,USP MANNITOL, Sorbitol Powder, Xylitol or erythritol.
2. the enzymatic synthesis method of novel fuel thickener as claimed in claim 1, it is characterized by described vinyl acetate is C
4above vinyl acetate and derivative thereof.
3. the enzymatic synthesis method of novel fuel thickener as claimed in claim 1, is characterized by described vinyl acetate and is preferably vinyl butyrate, valeric acid vinyl acetate, sad vinyl acetate or capric acid vinyl acetate.
4. the enzymatic synthesis method of novel fuel thickener as claimed in claim 1, it is characterized by described enzyme catalyst and be specially the letter N435 (Novozymes435) of Novi, the letter TLIM (Novozymes TL IM) of Novi, antarctic candidia lipase A (Candida antarctica Lipase A, CALA), candida antarctica lipase B (Candida antarctica Lipase B, CALB), candiyeast subspecies lipase 99-125 (Candida sp.99-125) or aspergillus oryzae lipase (Thermomyces Lanuginosus Lipase, TLL).
5. the enzymatic synthesis method of novel fuel thickener as claimed in claim 1, it is characterized by described eluent is methyl alcohol and chloroform mixed solution, volume ratio is methyl alcohol: chloroform=1:18～27.
6. the enzymatic synthesis method of novel fuel thickener as claimed in claim 1, it is characterized by described filter membrane is the mixed cellulose ester microporous membrane in 0.45 μ m aperture.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646438A (en) * | 2015-12-22 | 2016-06-08 | 天津大学 | Ketal sugar alcohol-based micromolecular gelator and preparation method and application thereof |
| CN107188806A (en) * | 2017-05-15 | 2017-09-22 | 浙江海洋大学 | A kind of fuel thickener and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1088891A (en) * | 1992-12-27 | 1994-07-06 | 青岛海洋大学 | Sea floating oil gelatinizer |
| CN101096588A (en) * | 2007-06-26 | 2008-01-02 | 陕西科技大学 | Ocean oil spilling gelling agent prepared by leather leftover bits and pieces and preparation method thereof |
-
2013
- 2013-12-03 CN CN201310644089.0A patent/CN103642842B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1088891A (en) * | 1992-12-27 | 1994-07-06 | 青岛海洋大学 | Sea floating oil gelatinizer |
| CN101096588A (en) * | 2007-06-26 | 2008-01-02 | 陕西科技大学 | Ocean oil spilling gelling agent prepared by leather leftover bits and pieces and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 张念湘等: "有机相中脂肪酶催化糖酯合成的研究", 《高等学校化学学报》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646438A (en) * | 2015-12-22 | 2016-06-08 | 天津大学 | Ketal sugar alcohol-based micromolecular gelator and preparation method and application thereof |
| CN107188806A (en) * | 2017-05-15 | 2017-09-22 | 浙江海洋大学 | A kind of fuel thickener and preparation method thereof |
| CN107188806B (en) * | 2017-05-15 | 2020-02-07 | 浙江海洋大学 | Oil gelling agent and preparation method thereof |
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| CN103642842B (en) | 2015-06-10 |
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