CN106140007A - A kind of oil field sulfomethylated lignin acidic group beet alkali surface activator and preparation method thereof - Google Patents
A kind of oil field sulfomethylated lignin acidic group beet alkali surface activator and preparation method thereof Download PDFInfo
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
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Abstract
The invention discloses the preparation method of a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator belonging to surfactant field, this surfactant is with lignin as raw material, the most oxidized, sulfonation generates oxidation lignosulfonate, synthesize sulfomethylated lignin acidic group glycine betaine through alkylated reaction again, be a kind of amphoteric surfactant.The raw material that the present invention uses is the by-product of the industries such as papermaking, reaction condition is gentle, does not produce public hazards, and the surfactant of preparation has preferable surface activity, < 10 can be formed with Daqing crude oil, xinjiang crude oil and North China crude oil when being used alone as non-base oil-displacing agent in tertiary oil recovery‑3The ultralow interfacial tension of mN/m；Be a kind of can apply in oil field, new and effective, with low cost containing sulfonic lignin amphoteric surfactant.
Description
Technical field
The invention belongs to surfactant preparing technical field, particularly to a kind of oil field sulfomethylated lignin acidic group glycine betaine
The preparation method of surfactant, a kind of can be used for sulfomethylated lignin acidic group glycine betaine oil displacement agent list used for tertiary oil recovery
Body and preparation method thereof.
Technical background
Through primary oil recovery and secondary oil recovery, the oil field of China is overall in recent years enters High water cut, high recovery percent of reserves
Development phase, remaining substantial oil rely on routine techniques be difficult to extraction.For improving oil recovery efficiency further, meet industry raw
The needs produced, tertiary oil recovery technology has played huge effect in terms of high yield is stablized in guarantee oil field.Most potential as one
Oil production method, surfactant flooding technology has become as the study hotspot in tertiary oil recovery technology at present.Adopt around three times
Oil tech, ternary composite driving technology is adopted by vast oil field as a kind of cost-effective oil recovery technique, and the effect obtained.
But due to the existence of alkali in system, causing oil well fouling occur, stratum clay dispersion, migration cause permeability decrease, capillary
The series of problems such as channel blockage and rock forming mineral corrosion, in order to overcome the side effect and defect caused by contained highly basic etc., adopt
Ternary composite driving technology is replaced imperative by alkali-free binary combination flooding system.Considering from oil displacement agent industrialization angle, alkali-free is multiple
Zoarium tie up to require interfacial tension reach ultralow while, wide material sources and cheap raw material to be found as far as possible, drop further
Low cost, making alkali-free compound system reach a standard economically is the main research objective of this technology, so efficiently, cheap novel drive
The development of oil preparation has highly important social meaning and economic implications.
As the by-product of the industries such as papermaking, lignin is typically to discharge with the form of garbage, has both wasted resource, dirty again
Dye environment, has certain economic and social benefit so making full use of it.Owing to lignin and modified product thereof have nothing
The feature such as malicious, with low cost, green, the conventional lignosulfonates with lignin as raw material production are the most the most frequently used wood
Quality based surfactants, but its surface activity is poor so that it is and application performance is subject to certain restrictions, and needs at molecular structure
The typical lipophilic group of middle introducing and hydrophilic group, could prepare the surfactant of function admirable.So, use general lignin
Sulfonate reduces the interfacial tension between profit and is difficult to, and needs to be modified lignosulfonates.But modified lignin
Sulfonate, after introducing lipophilic ingredient in the structure, still can not be formed super with crude oil when being used alone or under the conditions of alkali-free
Low interfacial tension, therefore cannot be directly used to the displacement of reservoir oil.Alkali lignin has been carried out by patent CN1360969A electroxidation, alkylation and
The research of sulfonation modifying, oil after modified lignin surfactant is compounding with petroleum sulfonate under conditions of with the presence of alkali
Water interfacial tension can reach 10‐3mN/m.In patent CN1123620C to lignosulfonates respectively with petroleum carboxylate and alkane
The compound system of base benzene sulfonate has carried out systematic research, finds its compound system oil-water interfaces under conditions of with the presence of alkali
Tension force all can reach 10‐3mN/m.Patent CN1327026A use the fatty acid amide Han Long carbon chain to lignosulfonates
Learn this property, send out oil water interfacial tension when being used alone under conditions of existing now with alkali and can reach 10‐3mN/m。
Sulfomethylated lignin acidic group glycine betaine is a kind of both sexes lignin-base surfactant with high surfaces activity.Deer is triumphant
Deng at " synthesis of a kind of lignosulfonates amphoteric surfactant and sign " (detergents and cosmetic .2012,42 (5): 329-332)
In with calcium lignosulfonate as Material synthesis a kind of lignosulfonates amphoteric surfactant, Xu Yongjian etc. is at " lignin
The synthesis of amphoteric surfactant and surface physical and chemical performance " (fine chemistry industry .2010,27 (8): 765-768) utilizes senior fat
Fat amine lignin quaternary is modified synthesize lignin-base surfactant, but concrete synthetic method or purposes all with
The present invention is different.The present invention, with cheap lignin as raw material, has synthesized a kind of both sexes lignin-base surface activity
Agent--sulfomethylated lignin acidic group glycine betaine, can form ultralow interfacial tension with crude oil when it is used alone under the conditions of alkali-free.
Summary of the invention
It is an object of the invention to provide the preparation method of a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator, its
Being characterised by, described sulfomethylated lignin acidic group beet alkali surface activator is with lignin as raw material, first with oxidising agent, sulfonated reagent
Reaction, introduces hydrophilic group on the side chain of lignin, the most first synthesis oxidation lignosulfonate, passes through alkylated reaction the most again
High fatty amine i.e. lipophilic group are incorporated in lignin molecule, i.e. can get lignin sulfonic acid base glycine betaine surface activity
Agent, specifically uses following steps:
1) lignin reacts with oxidising agent, sulfonated reagent, obtains aoxidizing lignosulfonate；
2) oxidation lignosulfonate prepares sulfomethylated lignin acidic group glycine betaine through alkylated reaction, is i.e. by high fatty amine also
It is exactly that lipophilic group is incorporated in lignin molecule, i.e. can get lignin sulfonic acid base beet alkali surface activator
Described step 1) concrete operation method be: being first according to mass ratio, lignin and oxidising agent are according to 10:
The ratio reaction of 0.05 4, reaction temperature is maintained at 20 100 DEG C, in 0.1 5 hours response time, obtains oxidative lignin；Secondly
It is 10:1 6 by oxidative lignin and sulfonated reagent according to mass ratio, under conditions of temperature is 50 250 DEG C, sulfonating reaction
0.1 10 hours, i.e. obtain aoxidizing lignosulfonate.
Described step 2) concrete operation method be: be first 1 by epoxychloropropane and high fatty amine according to mol ratio:
0.8 1.5, under the conditions of temperature is 30 100 DEG C, reacts 0.1 10 hours, obtain Long carbon chain fatty quaternary ammonium salt intermediate；Then
Oxidation lignosulfonate step (1) obtained and Long carbon chain fatty quaternary ammonium salt intermediate are that 1:0.5 2 is 40 according to mol ratio
React 0.1 10 hours at 100 DEG C, be cooled to room temperature, prepare sulfomethylated lignin acidic group beet alkali surface activator；
3) performance test, is dissolved in distilled water by product after purification, measures surface tension and critical micelle concentration, result table
Bright product can be dissolved in water at 25 DEG C, and its critical micelle concentration is 8 × 10‐3～1 × 10‐2G/L, γcmc< 27.0mN/m i.e. has
There is the highest surface activity.
Described oxidising agent is the one of hydrogen peroxide, nitric acid, sodium hypochlorite and potassium permanganate.
Described sulfonated reagent be sodium pyrosulfite or sodium sulfite, potassium sulfite or potassium metabisulfite or they be re-dubbed
Composite sulfonated reagent.
Described high fatty amine is ten alkyl dimethyl tertiary amide, Dodecyl Dimethyl Amine or dodecyldimethylamine base uncle
Amine.
The application of described surface activity base, as non-base oil-displacing agent, can make Daqing crude oil when being used alone, and North China is former
Oil and xinjiang crude oil reach < 10‐3The ultralow interfacial tension of mN/m.
The invention has the beneficial effects as follows that the raw material of sulfomethylated lignin acidic group beet alkali ampholytic surface active agent of the present invention is for wooden
Quality, is the by-product of paper industry, thus improves the added value of paper industry by-product；Interfacial tension test shows, this type of
Interfacial tension between profit can be made when surfactant is used alone under the conditions of alkali-free to reach ultralow, it is adaptable to surface activity
Agent polymer binary combination flooding improves oil recovery factor, be a kind of can apply in oil field, new and effective, with low cost containing
There is sulfonic lignin amphoteric surfactant.
Accompanying drawing explanation
Fig. 1 is raw material and product infrared spectrum spectrogram, and wherein (a) is raw material wood element；B () is sulfomethylated lignin acidic group Radix Betae
Alkali.
Fig. 2 is the surface tension change with concentration of sulfomethylated lignin acidic group aqueous solutions of betaine, and measuring temperature is 25 DEG C.
Detailed description of the invention
The present invention provides the preparation method of a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator, with paper industry
By-product lignin be raw material, first react with oxidising agent, sulfonated reagent to generate and aoxidizes lignosulfonate, more anti-through alkylation
Sulfomethylated lignin acidic group glycine betaine should be prepared, be a kind of amphoteric surfactant, oil when being used alone under the conditions of alkali-free, can be made
Water interfacial tension reaches ultralow.Below with reference to the drawings and specific embodiments, the present invention is described in further detail.
Embodiment 1:40g lignin and 6g H2O2Aoxidize 2 hours at 60 DEG C, be subsequently adding 6g formaldehyde and 8g Na2SO3
95 DEG C of sulfonation 8 hours, i.e. obtain aoxidizing lignosulfonate；By 9.25g epoxychloropropane and 21.34g dodecyl dimethyl
Tertiary amine reacts 3 hours at 55 DEG C, obtains Long carbon chain fatty quaternary ammonium salt intermediate；The 25.4g obtained is aoxidized lignosulfonate
React 3 hours at 55 DEG C with 33.605g Long carbon chain fatty quaternary ammonium salt intermediate, be cooled to room temperature, prepare lignin sulfonic acid
Base beet alkali surface activator.
Infrared spectrum analysis is done, in result such as Fig. 1 shown in (a, b) after product is purified.Compared with raw material wood element, wooden
Element sulfonic group glycine betaine product is at 2830cm‐1The C H key absworption peak at place is substantially strengthened, and illustrates that the introducing of high fatty amine makes to produce
Methyl and methylene in thing increase；1486cm‐1And 749cm‐1Place is the characteristic absorption peak of C N key in quaternary ammonium salt,
1370cm‐1And 1210cm‐1Near the characteristic absorption peak of S=O all occurs, illustrate successfully to synthesize target product.
The surface activity of product: product after purification is dissolved in distilled water, measures surface tension and critical glue at 25 DEG C
Bundle concentration, result is as shown in Figure 2.Fig. 2 shows, the critical micelle concentration of lignin sulfobetaines is 8 × 10‐3～1 × 10‐ 2G/L, γcmc< 27.0mN/m i.e. has the highest surface activity.
With grand celebration six factory formation water (total salinity 5617mg/L, lower same) configuration containing (mass fraction) oil displacement agent monomer
0.4%, with grand celebration dewatered oil as object, measuring oil water interfacial tension at 45 DEG C is 5.42 × 10‐3mN/m；Use North China Stratigraphic water
(total salinity 10789mg/L) configuration is containing (mass fraction) oil displacement agent monomer 0.4%, with capital, North China-11 crude oil as object, 54 DEG C
Lower mensuration oil water interfacial tension is 2.26 × 10‐3mN/m；With Xinjiang formation water (total salinity 6026mg/L) configuration containing (quality is divided
Number) oil displacement agent monomer 0.4%, with xinjiang crude oil as object, measuring oil water interfacial tension at 40 DEG C is 4.34 × 10‐3mN/m。
Embodiment 2:40g lignin and 6g H2O2Aoxidize 2 hours at 60 DEG C, be subsequently adding 6g formaldehyde and 8g Na2SO3
95 DEG C of sulfonation 8 hours, i.e. obtain aoxidizing lignosulfonate；By 9.25g epoxychloropropane and 24.15g dodecyldimethylamine base
Tertiary amine reacts 3 hours at 55 DEG C, obtains Long carbon chain fatty quaternary ammonium salt intermediate；The 25.4g obtained is aoxidized lignosulfonate
React 3 hours at 55 DEG C with 36.69g Long carbon chain fatty quaternary ammonium salt intermediate, be cooled to room temperature, prepare sulfomethylated lignin acidic group
Beet alkali surface activator.
With grand celebration six factory formation water (total salinity 5617mg/L, lower same) configuration containing (mass fraction) oil displacement agent monomer
0.4%, with grand celebration dewatered oil as object, measuring oil water interfacial tension at 45 DEG C is 1.36 × 10‐3mN/m；Use North China Stratigraphic water
(total salinity 10789mg/L) configuration is containing (mass fraction) oil displacement agent monomer 0.4%, with capital, North China-11 crude oil as object, 54 DEG C
Lower mensuration oil water interfacial tension is 1.19 × 10‐3mN/m；With Xinjiang formation water (total salinity 6026mg/L) configuration containing (quality is divided
Number) oil displacement agent monomer 0.4%, with xinjiang crude oil as object, measuring oil water interfacial tension at 40 DEG C is 4.38 × 10‐4mN/m。
Embodiment 3:40g lignin and 6g H2O2Aoxidize 1 hour at 70 DEG C, be subsequently adding 6g formaldehyde and 8g Na2SO3
80 DEG C of sulfonation 8 hours, i.e. obtain aoxidizing lignosulfonate；By 9.25g epoxychloropropane and 24.15g dodecyldimethylamine base
Tertiary amine reacts 3 hours at 55 DEG C, obtains Long carbon chain fatty quaternary ammonium salt intermediate.The 25.4g obtained is aoxidized lignosulfonate
React 3 hours at 55 DEG C with 43.36g Long carbon chain fatty quaternary ammonium salt intermediate, be cooled to room temperature, prepare sulfomethylated lignin acidic group
Beet alkali surface activator.
With grand celebration six factory formation water (total salinity 5617mg/L, lower same) configuration containing (mass fraction) oil displacement agent monomer
0.4%, with grand celebration dewatered oil as object, measuring oil water interfacial tension at 45 DEG C is 3.42 × 10‐3mN/m；Use North China Stratigraphic water
(total salinity 10789mg/L) configuration is containing (mass fraction) oil displacement agent monomer 0.4%, with capital, North China-11 crude oil as object, 54 DEG C
Lower mensuration oil water interfacial tension is 2.17 × 10‐3mN/m；With Xinjiang formation water (total salinity 6026mg/L) configuration containing (quality is divided
Number) oil displacement agent monomer 0.4%, with xinjiang crude oil as object, measuring oil water interfacial tension at 40 DEG C is 5.62 × 10‐4mN/m。
Embodiment 4:40g lignin and 4g H2O2Aoxidize 2 hours at 60 DEG C, be subsequently adding 8g Na2SO3At 180 DEG C of sulphurs
Change 30 minutes, i.e. obtain aoxidizing lignosulfonate；By 9.25g epoxychloropropane with 21.34g Dodecyl Dimethyl Amine 45
React 4 hours at DEG C, obtain Long carbon chain fatty quaternary ammonium salt intermediate mesosome.By obtain 25.4g oxidation lignosulfonate and
33.605g Long carbon chain fatty quaternary ammonium salt intermediate reacts 2 hours at 65 DEG C, is cooled to room temperature, prepares sulfomethylated lignin acidic group
Beet alkali surface activator.
With grand celebration six factory formation water (total salinity 5617mg/L, lower same) configuration containing (mass fraction) oil displacement agent monomer
0.4%, with grand celebration dewatered oil as object, measuring oil water interfacial tension at 45 DEG C is 1.86 × 10‐3mN/m；Use North China Stratigraphic water
(total salinity 10789mg/L) configuration is containing (mass fraction) oil displacement agent monomer 0.4%, with capital, North China 11 crude oil as object, 54 DEG C
Lower mensuration oil water interfacial tension is 1.17 × 10‐3mN/m；With Xinjiang formation water (total salinity 6026mg/L) configuration containing (quality is divided
Number) oil displacement agent monomer 0.4%, with xinjiang crude oil as object, measuring oil water interfacial tension at 40 DEG C is 3.26 × 10‐4mN/m。
Embodiment 5:40g lignin and 4g H2O2Aoxidize 2 hours at 60 DEG C, be subsequently adding 8g Na2SO3At 180 DEG C of sulphurs
Change 1 hour, i.e. obtain aoxidizing lignosulfonate；By 9.25g epoxychloropropane with 24.15g dodecyldimethylamine base tertiary amine 65
React 2 hours at DEG C, obtain Long carbon chain fatty quaternary ammonium salt intermediate body.By obtain 25.4g oxidation lignosulfonate and
50.02g Long carbon chain fatty quaternary ammonium salt intermediate reacts 2.5 hours at 60 DEG C, is cooled to room temperature, prepares sulfomethylated lignin acidic group
Beet alkali surface activator.
With grand celebration six factory formation water (total salinity 5617mg/L, lower same) configuration containing (mass fraction) oil displacement agent monomer
0.4%, with grand celebration dewatered oil as object, measuring oil water interfacial tension at 45 DEG C is 3.92 × 10‐3mN/m；Use North China Stratigraphic water
(total salinity 10789mg/L) configuration is containing (mass fraction) oil displacement agent monomer 0.4%, with capital, North China-11 crude oil as object, 54 DEG C
Lower mensuration oil water interfacial tension is 4.16 × 10‐3mN/m；With Xinjiang formation water (total salinity 6026mg/L) configuration containing (quality is divided
Number) oil displacement agent monomer 0.4%, with xinjiang crude oil as object, measuring oil water interfacial tension at 40 DEG C is 7.86 × 10‐4mN/m。
Claims (5)
1. the oil field preparation method of sulfomethylated lignin acidic group beet alkali surface activator, it is characterised in that described lignin
Sulfonic group beet alkali surface activator, with lignin as raw material, first reacts with oxidising agent, sulfonated reagent, hydrophilic group is introduced
On the side chain of lignin, the most first synthesis oxidation lignosulfonate, the most again by alkylated reaction by high fatty amine the most namely
Lipophilic group is incorporated in lignin molecule, i.e. can get lignin sulfonic acid base beet alkali surface activator, and concrete employing walks as follows
Rapid:
1) lignin reacts with oxidising agent, sulfonated reagent, obtains aoxidizing lignosulfonate；
2) oxidation lignosulfonate prepares sulfomethylated lignin acidic group glycine betaine through alkylated reaction, is i.e. by high fatty amine namely
Lipophilic group is incorporated in lignin molecule, i.e. obtains sulfomethylated lignin acidic group beet alkali surface activator；
Described step 1) concrete operation method be: being first according to mass ratio, lignin and oxidising agent are according to 10:0.05-4's
Ratio is reacted, and reaction temperature is maintained at 20-100 DEG C, in 0.1-5 hour response time, obtains oxidative lignin；Secondly will oxidation wood
Quality and sulfonated reagent are 10:1-6 according to mass ratio, under conditions of temperature is 50-250 DEG C, and sulfonating reaction 0.1-10 hour,
I.e. obtain aoxidizing lignosulfonate；
Described step 2) concrete operation method be: be first 1:0.8-by epoxychloropropane and high fatty amine according to mol ratio
1.5, under the conditions of temperature is 30-100 DEG C, react 0.1-10 hour, obtain Long carbon chain fatty quaternary ammonium salt intermediate；Then will step
Rapid 1) the oxidation lignosulfonate obtained and Long carbon chain fatty quaternary ammonium salt intermediate are that 1:0.5-2 is at 40-100 DEG C according to mol ratio
Lower reaction 0.1-10 hour, is cooled to room temperature, prepares sulfomethylated lignin acidic group beet alkali surface activator；
3) performance test, is dissolved in distilled water by product after purification, measures surface tension and critical micelle concentration, and result shows to produce
Product can be dissolved in water at 25 DEG C, and its critical micelle concentration is 8 × 10-3～1 × 10-2G/L, γcmc< 27.0mN/m i.e. has very
High surface activity.
The preparation method of a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator, it is special
Levying and be, described oxidising agent is the one of hydrogen peroxide, nitric acid, sodium hypochlorite and potassium permanganate.
The preparation method of a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator, it is special
Levy and be, described sulfonated reagent be sodium pyrosulfite or sodium sulfite, potassium sulfite or potassium metabisulfite or they be re-dubbed
Composite sulfonated reagent.
The preparation method of a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator, it is special
Levying and be, described high fatty amine is ten alkyl dimethyl tertiary amide, Dodecyl Dimethyl Amine or dodecyldimethylamine base uncle
Amine.
5. a kind of oil field sulfomethylated lignin acidic group beet alkali surface activator described in claim 1 an application, its feature
It is, the application of described surfactant, as non-base oil-displacing agent, Daqing crude oil, North China crude oil can be made when being used alone
And xinjiang crude oil reaches < 10-3The ultralow interfacial tension of mN/m.
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Cited By (6)
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| CN110791262A (en) * | 2019-11-07 | 2020-02-14 | 西安石油大学 | Lignin-derived non-foam drilling fluid viscosity reducer and preparation method thereof |
| CN111939833A (en) * | 2020-08-17 | 2020-11-17 | 重庆化工职业学院 | Preparation method of modified lignin sulfobetaine surfactant |
| CN112760089A (en) * | 2021-01-28 | 2021-05-07 | 重庆化工职业学院 | Lignin-based gemini surfactant and preparation method thereof |
| CN113046047A (en) * | 2021-03-12 | 2021-06-29 | 重庆化工职业学院 | Preparation method of temperature-resistant surfactant for oil displacement |
| CN113663598A (en) * | 2021-08-24 | 2021-11-19 | 天津大学 | Preparation of composite lignin-based surfactant and application of composite lignin-based surfactant in treatment of oily sludge |
| CN115466406A (en) * | 2021-06-11 | 2022-12-13 | 华南理工大学 | PH-UCST response type lignin-based zwitterionic compound, preparation method thereof and method for recovering cellulase at room temperature |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110791262A (en) * | 2019-11-07 | 2020-02-14 | 西安石油大学 | Lignin-derived non-foam drilling fluid viscosity reducer and preparation method thereof |
| CN110791262B (en) * | 2019-11-07 | 2021-12-17 | 西安石油大学 | Lignin-derived non-foam drilling fluid viscosity reducer and preparation method thereof |
| CN111939833A (en) * | 2020-08-17 | 2020-11-17 | 重庆化工职业学院 | Preparation method of modified lignin sulfobetaine surfactant |
| CN112760089A (en) * | 2021-01-28 | 2021-05-07 | 重庆化工职业学院 | Lignin-based gemini surfactant and preparation method thereof |
| CN112760089B (en) * | 2021-01-28 | 2022-10-14 | 重庆化工职业学院 | Lignin-based gemini surfactant and preparation method thereof |
| CN113046047A (en) * | 2021-03-12 | 2021-06-29 | 重庆化工职业学院 | Preparation method of temperature-resistant surfactant for oil displacement |
| CN115466406A (en) * | 2021-06-11 | 2022-12-13 | 华南理工大学 | PH-UCST response type lignin-based zwitterionic compound, preparation method thereof and method for recovering cellulase at room temperature |
| CN115466406B (en) * | 2021-06-11 | 2023-08-22 | 华南理工大学 | PH-UCST responsive lignin-based zwitterionic compound and preparation method thereof and method for recycling cellulase at room temperature |
| CN113663598A (en) * | 2021-08-24 | 2021-11-19 | 天津大学 | Preparation of composite lignin-based surfactant and application of composite lignin-based surfactant in treatment of oily sludge |
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