CN102976906A - Method for separating phenols from bio-oil - Google Patents
Method for separating phenols from bio-oil Download PDFInfo
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Abstract
The invention provides a method for separating phenols from bio-oil, which relates to a method for separating phenols from oil obtained through pyrolysis of biomass. The method comprises the following steps: distilling bio-oil, intercepting fractions obtained at a temperature below 160 DEG C and adding aqueous alkali for alkalization until the pH value of the fractions is greater than 10; and extracting an alkalized solution with an extractant, acidifying a water phase left after extraction with an acid, then adding a saline solution, carrying out extraction again by using a back-extractant and removing an organic phase through reduced pressure distillation so as to obtain a mixture of phenols. The method provided by the invention both broadens usage and improves the economic value of the bio-oil and opens up a wide prospect for separation and utilization of the bio-oil.
Description
Technical field
The present invention relates to a kind of from biomass pyrolysis oil the method for separating phenols.
Background technology
The energy dilemma that the environmental problem that the use of fossil energy brings and traditional energy exhaustion cause has received increasing concern, therefore, develops the alternative energy and is necessary very much.At present, in various renewable energy sources, biomass are unique environmental friendliness energy that can be converted into liquid fuel, have wide material sources, cheap and easy to get, recyclability is strong, the advantage such as pollution-free.Its trans-utilization can not only be realized CO
2Zero release, but also can utilize the generations such as agriculture and forestry organic waste material, domestic refuse to can be used as the materials such as gas, liquid and solid of the energy, reach the purpose that turns waste into wealth, fully utilizes.Particularly from the liquid that Wood Adhesives from Biomass obtains also further separation and Extraction have the more chemical of high added value, therefore, the exploitation prospect of biomass is wide.At present, biomass utilize approach mainly contain take microbial fermentation as representative the biological chemistry platform and take pyrolysis, gasification as the thermochemistry platform of representative.Compare with biomass gasification technology with microbial fermentation, the biomass fast pyrogenation cost is relatively low, can directly produce the bio oil that exists with liquid form and become the most potential biomass to utilize one of technology.
The biomass fast pyrogenation technology refer to biomass under anaerobic or anoxia condition, adopt high heating rate (500 ~ 1000 ℃/s), utmost point short residence time(SRT) (~ 2s) and medium cracking temperature (~ 500 ℃) obtain bio oil through fast pyrogenation and rapid condensation, produce simultaneously the process of by product charcoal and incondensable gas.Bio oil is a kind of flowable liquids of burgundy, contains hundreds of materials such as comprising acid, alcohol, ester, aldehyde, phenol, ketone, has that acid number height, viscosity are large, water content and a shortcoming such as oxygen level is high, calorific value is low, so it directly utilizes and is restricted.Biological oil properties can substitute or the part substitute fossil fuels in order to improve, and people do a lot of work at aspects such as shortening, catalytic pyrolysis, catalytic esterification, steam reformings.Although these methods can improve calorific value and the stability of bio oil, because treating process needs lot of energy or hydrogen, cause cost to raise.And the separation and Extraction high valuable chemicals not only can improve the economic worth of bio oil from bio oil, promotes the realization of bio oil industrialization, also is simultaneously more promising a kind of in the present bio oil trans-utilization mode.Contain a large amount of phenols such as phenol, 2-methylphenol, 4-methylphenol, 2-methoxyphenol, 4-methyl-2-methoxyphenol, 4-ethyl-2-methoxyphenol, Eugenol, Vanillin etc. in the bio oil, can be used for the aspects such as agricultural chemicals, medicine, explosive, engineering plastics, synthon, softening agent, sanitas, spices and fuel.Yet also less about the research of separating phenols from bio oil so far, the publication report is also few.
Chinese patent CN201210201734.7 discloses a kind of process for purification for each component separation of bio oil, comprises the steps: that (1) bio oil through washing, gets water lotion and rinsing residue; (2) the water lotion underpressure distillation gets carbohydrate and water, uses ethyl acetate extraction after the rinsing residue drying, gets extraction liquid and insoluble sludge; (3) the extraction liquid underpressure distillation gets phenols, and insoluble sludge is dry to be got final product.This invention adopts the simple process processes such as washing, underpressure distillation, extraction that bio oil is divided into water, carbohydrate, phenols and four parts of insoluble sludge, improves the added value of bio oil.
Chinese patent CN200910193381.9 discloses method and the device that a kind of biomass graded pyrolysis prepares bio oil and chemical, this invention has different thermal decomposition characteristics based on each Main chemical component (Mierocrystalline cellulose, hemicellulose and xylogen) of biomass, technical requirements in conjunction with fast pyrogenation, propose a kind of technical scheme of under differing temps, biomass being carried out the classification pyrolysis by spiral pyrolysis reactor, surface bed fluidized-bed and deep fluidized bed three-level system, gradablely prepare different products.Wherein, the first step makes certain amount of organic acid (mainly being acetic acid) and aldehyde product; The second stage makes a certain amount of phenol products; Making pyrolysis gas by the third stage purifies and the condensed high-quality bio oil of main products that obtains native system of spray thrower spray through the two stage cyclone separator.Because the bio oil that the classification pyrolysis finally makes has moisture and amount of acidic substances is low, the characteristics of accumulating good stability.
Chinese patent CN201110089928.8 discloses a kind of molecular distillation separation method of bio oil, comprise: the pretreated bio oil that bio oil crude oil is carried out obtaining after particle and the moisture removal pre-treatment is through the molecular distillation sepn process, be normal temperature to 200 ℃ in distillation temperature, distillation pressure is under the 10Pa to 1800Pa, obtains the bio oil cut; The matter cut is as raw material in the bio oil that obtains, be normal temperature to 200 ℃ in distillation temperature, distillation pressure is under the 10Pa to 1800Pa, through repeatedly molecular distillation sepn process, extracts carboxylic-acid, aldehydes, ketone, alcohols, phenols or saccharide compound in the bio oil cut.This invented technology introduces the separation field of thermo-sensitivity bio oil with the molecular distillation isolation technique, solved descend problem with coking of quality of bio-oil in the sepn process, and the different bio oil cut of characteristic and multiple chemical products with high added-value can be provided.
The applicant provides a kind of at Chinese patent CN201210050527.6 both can extract aldehydes matter from bio oil, again can by-product acetate, and can promote the quality of bio oil, the acidity of bio oil is reduced, and the separation upgrading method of the bio oil of considerable change not occur calorific value.In bio oil, add complexing agent and carry out complex reaction, separate obtaining complex precipitate; In complex precipitate, add acid, obtain aldehydes matter and metal salt solution, filter, remove the impurity such as charcoal particle, obtain the mixing solutions of aldehydes matter and metal-salt; Add extraction agent in mixing solutions, leave standstill, solution is divided into two-layer, and the upper strata is the aldehydes matter extraction phase, and lower floor is the metal salt solution phase, and aldehydes matter extraction phase and metal salt solution are separated, and obtains aldehydes matter and metal salt solution.
Summary of the invention
The object of the present invention is to provide a kind of from bio oil the method for separating phenols.
The present invention includes following steps:
1) bio oil is distilled, the cut of intercepting below 160 ℃ adds alkaline solution and alkalizes to pH〉10;
2) get alkalizing solution and extract with extraction agent, water remaining after the extraction carries out acidifying with acid, adds salts solution again, extracts with strippant again, removes organic phase by underpressure distillation, namely obtains phenol mixture.
In step 1), described bio oil can be wooden class bio oil or draft class bio oil, and described wooden class bio oil can be selected from the bio oil of pine, China fir or poplar etc.; Described draft class bio oil can be selected from the bio oil of stalk, Chinese silvergrass or rice husk etc.;
The method of described distillation can be: bio oil is placed container, air distillation is carried out in elder generation's oil bath heating, heating rate is 10 ℃/min, when reaching 160 ℃, temperature keeps distillation 1h, to guarantee that the bio oil mid-boiling point is lower than 160 ℃ substance and all steams, weigh after residuum to be distilled and the cut cooling, collect and obtain a certain amount of distillation fraction; It is the sodium hydroxide solution of 2.5mol/L that described alkaline solution can adopt concentration; The pH of solution can be 10 ~ 13.5 after the described alkalization, take pH〉12 be best.
In step 2) in, described extraction agent can adopt ethyl acetate etc.; Described acid can be adopted hydrochloric acid etc., and the concentration of described hydrochloric acid can be 2.5mol/L; Described acidifying, to pH be 6; Described salt can be selected from a kind of in sodium-chlor, SODIUMNITRATE, sodium sulfate, magnesium chloride, magnesium nitrate, iron(ic) chloride, iron nitrate, calcium chloride, nitrocalcite, Repone K, saltpetre, the vitriolate of tartar etc., take sodium-chlor as best; Described strippant can be selected from a kind of in ethyl acetate, butylacetate, normal hexane, the sherwood oil etc., take butylacetate as best; The number of times of described extraction can be 2～3 times, and the described again number of times of extraction can be 2～3 times.
The present invention to composition and the detection method of content of sample is: Gas Chromatography-mass Spectrometer (GCMS) (GC-MS).This instrument is available from Japanese Shimadzu company, and model is GC-MS 2010plus.The GC operational condition is: Wax-5MS capillary column, 30m * 0.25mm * 0.25mm; Carrier gas: helium, purity 99.9999%, flow 1.2mL/min.The column temperature rise program: 50 ℃ of initial temperatures keep 5min, are heated to 250 ℃ with the temperature rise rate of 4 ℃/min, and splitting ratio is 30: 1, sample size: 1 μ L.The MS operational condition is: the EI source, and electron energy 70eV, sweep limit 30～550amu, 200 ℃ of ion source temperatures, 270 ℃ of interface temperature, the solvent delay time is 2min.Each detected components is sample introduction behind 4%, the 0.45 μ m PTFE filtering with microporous membrane with acetone diluted to concentration all.
Have the character of weak acid owing to contain a hydroxyl on the phenols phenyl ring, the form that the phenols in the cut ionizes with phenates in strong alkali solution exists; Then get a certain amount of alkalizing solution and use respectively extraction agent (such as ethyl acetate) extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.The non-phenol organic matter that contains the overwhelming majority in the organic phase, and phenates is present in the aqueous phase solution.The purpose of high salt concentration solion is to impel the reaction of phenates formation phenol under the acidic conditions to carry out to the right.Respectively with a certain amount of strippant extraction 3 times, mix concussion again, collect the organic phase that contains phenols after leaving standstill 1h, the temperature underpressure distillation suitable according to the strippant type selecting obtains the phenols component.
The present invention propose a kind of from bio oil the method for separation and Extraction aldehydes matter, it at first alkalizes to the bio oil distillation fraction, then extracts with organic solvent; Salt adding again after remaining water is acidified with acid; Strip with organic solvent at last and obtain the aldehydes matter of higher degree.If choose the higher biomass of content of lignin as the bio oil raw material, simultaneously the biomass pyrolytic condition is optimized, can obtain more high purity and the more aldehydes matter of content.This from bio oil the technique of separating phenols not only expanded the purposes of bio oil, and improved the economic worth of bio oil, for bright prospects have been opened up in biological oil separating utilization.
Embodiment
Embodiment 1
Bio oil is carried out air distillation process the acquisition distillation fraction under 160 ℃ of conditions, polyphenol substance and content in bio oil and the cut are as shown in table 1.Get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 10.5.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL ethyl acetate extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 73.2wt%.
Table 1
Embodiment 2
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 12.0.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL ethyl acetate extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 74.7wt%.
Embodiment 3
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 11.5.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL n-butyl acetate extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 78.1wt%.
Embodiment 4
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 12.5.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL n-butyl acetate extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 79.3wt%.
Embodiment 5
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 12.0.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL n-hexane extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 73.7wt%.
Embodiment 6
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 13.0.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL n-hexane extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 73.4wt%.
Embodiment 7
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 11.0.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL petroleum ether extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 64.03wt%.
Embodiment 8
Similar to Example 1, get 5mL bio oil distillation fraction add concentration be the sodium hydroxide solution of 2.5mol/L alkalize to pH be 12.0.Get the 2mL alkalizing solution and use respectively the 2mL ethyl acetate extraction 3 times, mix concussion and leave standstill 1h, form well-bedded organic phase and water.Get aqueous phase solution 2mL and add concentration to be that the 2.5mol/L hydrochloric acid soln is acidified to pH about 6.0, and to add 2mL concentration be the sodium chloride solution of 2.5mol/L.Use respectively again 2mL petroleum ether extraction 3 times, mix concussion, leave standstill 1h after, collect the organic phase that contains phenols, recording phenols purity is 68.30wt%.
Claims (10)
1. the method for a separating phenols from bio oil is characterized in that may further comprise the steps:
1) bio oil is distilled, the cut of intercepting below 160 ℃ adds alkaline solution and alkalizes to pH〉10;
2) get alkalizing solution and extract with extraction agent, water remaining after the extraction carries out acidifying with acid, adds salts solution again, extracts with strippant again, removes organic phase by underpressure distillation, namely obtains phenol mixture.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 1) described bio oil is wooden class bio oil or draft class bio oil.
As claimed in claim 2 a kind of from bio oil the method for separating phenols, it is characterized in that described wooden class bio oil is selected from the bio oil of pine, China fir or poplar; Described draft class bio oil is selected from the bio oil of stalk, Chinese silvergrass or rice husk.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 1), the method of described distillation is: bio oil is placed container, air distillation is carried out in elder generation's oil bath heating, heating rate is 10 ℃/min, keeps distillation 1h when temperature reaches 160 ℃, to guarantee that the bio oil mid-boiling point is lower than 160 ℃ substance and all steams, weigh after residuum to be distilled and the cut cooling, collect and obtain a certain amount of distillation fraction.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 1) it is the sodium hydroxide solution of 2.5mol/L that described alkaline solution adopts concentration.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 1) the pH of solution is 10～13.5 after the described alkalization, take pH〉12 be best.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 2) in, described extraction agent adopts ethyl acetate.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 2) in, hydrochloric acid is adopted in described acid; The concentration of described hydrochloric acid is 2.5mol/L.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 2) in, the described pH of being acidified to is 6; Described salt can be selected from a kind of in sodium-chlor, SODIUMNITRATE, sodium sulfate, magnesium chloride, magnesium nitrate, iron(ic) chloride, iron nitrate, calcium chloride, nitrocalcite, Repone K, saltpetre, the vitriolate of tartar, take sodium-chlor as best.
As claimed in claim 1 a kind of from bio oil the method for separating phenols, it is characterized in that in step 2) in, described strippant is selected from a kind of in ethyl acetate, butylacetate, normal hexane, the sherwood oil, take butylacetate as best; The number of times of described extraction can be 2～3 times, and the described again number of times of extraction can be 2～3 times.
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Cited By (9)
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| CN103193833A (en) * | 2013-03-28 | 2013-07-10 | 中国林业科学研究院林产化学工业研究所 | Method for preparing monosaccharide ester and polyphenol product from biomasses by pressurizing, liquefying and directionally extracting and separating |
| CN103466873A (en) * | 2013-09-30 | 2013-12-25 | 河南龙成煤高效技术应用有限公司 | Method for processing sewage with high-concentration phenol and ammonia |
| CN104004597A (en) * | 2014-05-14 | 2014-08-27 | 中国科学院广州能源研究所 | Method for modification of biomass pyrolytic oil lightweight components/water phase by using in-situ hydrogenation reaction |
| CN105523895A (en) * | 2015-12-14 | 2016-04-27 | 中国科学技术大学 | Method for recovering phenols in bio-oil |
| WO2017141269A1 (en) | 2016-02-19 | 2017-08-24 | Council Of Scientific & Industrial Research | An eco-friendly process for the isolation of vanillin from ipomea carnea |
| CN107098796A (en) * | 2017-04-27 | 2017-08-29 | 中国科学院青岛生物能源与过程研究所 | The method that guaiacol is obtained from fast pyrogenation bio oil |
| CN111662433A (en) * | 2020-07-16 | 2020-09-15 | 河南省高新技术实业有限公司 | Preparation method of wood tar curing agent |
| CN112755585A (en) * | 2020-12-22 | 2021-05-07 | 北京元泰达环保科技有限公司 | Antioxidant production method |
| CN114736103A (en) * | 2022-05-18 | 2022-07-12 | 天津大学 | Method for separating propyl guaiacol and propyl syringol from lignin oil |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193833A (en) * | 2013-03-28 | 2013-07-10 | 中国林业科学研究院林产化学工业研究所 | Method for preparing monosaccharide ester and polyphenol product from biomasses by pressurizing, liquefying and directionally extracting and separating |
| CN103193833B (en) * | 2013-03-28 | 2016-03-02 | 中国林业科学研究院林产化学工业研究所 | Pressurized liquefied and the directed extracting and separating of biomass prepares the method for methylglycoside and polyphenol product |
| CN103466873A (en) * | 2013-09-30 | 2013-12-25 | 河南龙成煤高效技术应用有限公司 | Method for processing sewage with high-concentration phenol and ammonia |
| CN103466873B (en) * | 2013-09-30 | 2015-09-02 | 河南龙成煤高效技术应用有限公司 | A kind of process is containing the method for high-concentration phenol, ammonia sewage |
| CN104004597A (en) * | 2014-05-14 | 2014-08-27 | 中国科学院广州能源研究所 | Method for modification of biomass pyrolytic oil lightweight components/water phase by using in-situ hydrogenation reaction |
| CN104004597B (en) * | 2014-05-14 | 2016-03-30 | 中国科学院广州能源研究所 | A kind ofly add in-place H-H reaction is utilized to carry out the method for upgrading to biomass pyrolysis oil light component/aqueous phase |
| CN105523895A (en) * | 2015-12-14 | 2016-04-27 | 中国科学技术大学 | Method for recovering phenols in bio-oil |
| WO2017141269A1 (en) | 2016-02-19 | 2017-08-24 | Council Of Scientific & Industrial Research | An eco-friendly process for the isolation of vanillin from ipomea carnea |
| CN107098796A (en) * | 2017-04-27 | 2017-08-29 | 中国科学院青岛生物能源与过程研究所 | The method that guaiacol is obtained from fast pyrogenation bio oil |
| CN111662433A (en) * | 2020-07-16 | 2020-09-15 | 河南省高新技术实业有限公司 | Preparation method of wood tar curing agent |
| CN111662433B (en) * | 2020-07-16 | 2022-07-22 | 河南省高新技术实业有限公司 | Preparation method of wood tar curing agent |
| CN112755585A (en) * | 2020-12-22 | 2021-05-07 | 北京元泰达环保科技有限公司 | Antioxidant production method |
| CN114736103A (en) * | 2022-05-18 | 2022-07-12 | 天津大学 | Method for separating propyl guaiacol and propyl syringol from lignin oil |
| CN114736103B (en) * | 2022-05-18 | 2023-09-22 | 天津大学 | Method for separating propyl guaiacol and propyl syringol from lignin oil |
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