CN102304069B - Method for synthesizing saturated cardanol sulfonate surfactant for oil displacement - Google Patents
Method for synthesizing saturated cardanol sulfonate surfactant for oil displacement Download PDFInfo
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- saturated cardanol
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- cardanol
- sulfonic acid
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- 239000004094 surface-active agent Substances 0.000 title abstract description 29
- -1 saturated cardanol sulfonate Chemical class 0.000 title abstract description 14
- 238000006073 displacement reaction Methods 0.000 title abstract description 13
- 238000000034 method Methods 0.000 title abstract description 7
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical class OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims abstract description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 38
- 239000013543 active substance Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 17
- 238000006386 neutralization reaction Methods 0.000 abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 16
- 238000004821 distillation Methods 0.000 abstract description 12
- 238000006277 sulfonation reaction Methods 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 8
- 229910017053 inorganic salt Inorganic materials 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000019600 saltiness Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011206 ternary composite Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a method for synthesizing saturated cardanol sulfonate surfactant for oil displacement. The synthesis method comprises the following steps: firstly, performing a sulfonation reaction by using saturated cardanol as a raw material, fuming sulfuric acid as a sulfonating agent and dichloromethane as a solvent, and obtaining saturated cardanol sulfonic acid by distillation under a reduced pressure; and secondly, performing a neutralization reaction by using synthesized saturated cardanol sulfonic acid and sodium hydroxide as raw materials and ethanol as solvent, filtering the obtained mixture under negative pressure, and drying to obtain the saturated cardanol sulfonate surfactant. In the synthesis by the method, the reaction conditions are mild, the product purification is easy, the yield is high, and the raw material is cheap biological phenol. The surfactant has high interface activity and high salt resistance and can be used as an environment-friendly oil displacement surfactant.
Description
Technical field
The invention belongs to a kind of displacement of reservoir oil with the synthetic method of saturated cardanol sulfosalt surfactant, specifically take the saturated cardanol of biomass of environmental protection as raw material, at ambient temperature, by sulfonation and the neutralization two synthetic class environmental type surfactant oil displacements of simple organic reaction of step.
Background technology
Tensio-active agent is due to its special amphiphilic structure and character, is widely used in a plurality of industries and the fields such as washing, lubricated, food, makeup, agricultural, oil recovery.Wherein aniorfic surfactant has the advantages such as higher interfacial activity and high thermal resistance, is widely used in tertiary oil recovery technology as oil-displacing agent, is used for improving the recovery ratio of crude oil.Sulfonated lignin are tensio-active agents of recommending the earliest for the displacement of reservoir oil, but because interfacial activity is poor, only use in surfactant flooding as sacrifice agent.Real a large amount of aniorfic surfactant as oil-displacing agent is sulfonated petro-leum and synthesising sulfonate.Wherein to have production technique simple, cheap for sulfonated petro-leum, with the advantage such as the compatibleness of crude oil is good, is widely used in the tertiary oil recovery field as oil-displacing agent; But higher than 3% oil reservoir, its Oil Displacing Capacity reduces greatly for saltiness, and adsorptive capacity and the product performance otherness larger.After the nineties in 20th century, the research and development of external surfactant oil displacement mainly concentrate on heavy alkylbenzene sulfonate.Such tensio-active agent is under alkali-free or weak base condition, all has higher interfacial activity, can be with the interfacial tension lowering of the profit scope to ultra low interfacial tension, increase substantially the recovery ratio of crude oil, but because raw materials for production purity is low, caused the purity of product low, poor stability, price is relatively costly simultaneously.People are seeking substitute products always in recent years, develop relatively inexpensive surfactant oil displacement.
Summary of the invention
In order to solve the problem that exists in background technology, the present invention has synthesized a kind of displacement of reservoir oil with saturated cardanol sulfosalt surfactant.This tensio-active agent is that production technique is simple, and is cheap take the saturated cardanol of biomass as raw material, and the purity of product is higher; And have higher interfacial activity and salt tolerance.
The technical solution adopted in the present invention content is: the displacement of reservoir oil comprises following experimental procedure with saturated cardanol sulfosalt surfactant synthetic, take saturated cardanol as raw material, oleum is sulphonating agent, methylene dichloride is solvent, at 10 ~ 30 ℃ of lower sulfonation reaction 1 ~ 4 h, with reaction product underpressure distillation under 20 ~ 70 ℃, 50 ~ 266.6Pa condition, namely get saturated cardanol sulfonic acid; Then take this saturated cardanol sulfonic acid and sodium hydroxide as raw material, ethanol is solvent, and neutralization is reacted to system pH most 7 ~ 8 under 10 ~ 30 ℃, and reaction product is through negative pressure filtration, and the gained solid is at 40 ~ 80 ℃ of lower vacuum-drying 5 ~ 12h.Namely get the displacement of reservoir oil with saturated cardanol sulfosalt surfactant.
In above-mentioned saturated cardanol sulfosalt surfactant synthetic, the mass ratio of saturated cardanol and oleum is 1:0.8-1.5, is preferably 1:1.05; Described oleum is for containing the free SO of 10-50%
3, preferred 20% free SO
3Oleum, the volume fraction of solvent for use methylene dichloride in whole sulfonation reaction system is 50% ~ 70%; In the sulfonation reaction process, slowly drip oleum, the temperature during dropping is that 0 ~ 30 ℃, time for adding are 1 ~ 4h, and sulfonation temperature is 10 ~ 30 ℃, and the sulfonation time is 1 ~ 4h.In the neutralization reaction process, sodium hydroxide used can be the form of the aqueous solution, and its concentration is 3 ~ 7mol/L, is preferably 5 mol/L; The temperature of neutralization reaction is 10 ~ 30 ℃, and when neutralization reaction stops, the pH of system is 7 ~ 8, and solvent for use ethanol is that the volume fraction of whole neutralization reaction system is 60 ~ 80%.
The invention has the beneficial effects as follows: the present invention proposes and adopting the saturated cardanol of biomass is raw material, utilizes the benzene ring substitution group effect, by simple organic reaction, and a synthetic novel displacement of reservoir oil sulfonate surfactant of class.Be raw material owing to having adopted the saturated cardanol of cheap biomass, oleum is sulphonating agent, therefore this temperature of reaction is gentle, reaction times is shorter, operate also fairly simplely, and purify easily, overcome the problems such as traditional sulfosalt surfactant cost is high, complicated operation.The saturated cardanol sulfosalt surfactant that the present invention synthesizes belongs to typical tensio-active agent, contains the long-chain lipophilic group of 15 carbon in molecule, has higher interfacial activity, can be widely used in three and adopt Surface During surfactant flood and ternary composite driving.
Description of drawings:
Fig. 1 is the building-up reactions equation of saturated cardanol sulfosalt surfactant;
Fig. 2 is that the yield of saturated cardanol sulfonate and active matter content are with the change curve of oleum dropping temperature;
Fig. 3 is that the yield of saturated cardanol sulfonate and active matter content are with the change curve of oleum time for adding;
Fig. 4 is the yield of saturated cardanol sulfonate and the active matter content change curve with the sulfonation time;
Fig. 5 is that the yield of saturated cardanol sulfonate and active matter content are with the change curve of naoh concentration;
Fig. 6 is the dynamic interface tension force of saturated cardanol sulfosalt surfactant in the time of 45 ℃.
Embodiment:
The invention will be further described below in conjunction with embodiment:
Embodiment 1: accurately take saturated cardanol 10g and be dissolved in the 50mL methylene dichloride, slowly drip while stirring 10.5g under 0 ~ 30 ℃ and contain 20% free SO
3Oleum, time for adding is 2h, after dropwising, is warming up under 25 ℃ and reacts 3h, underpressure distillation under 50 ℃, the condition of 133.3Pa gets saturated cardanol sulfonic acid.With 50mL ethanol, saturated cardanol sulfonic acid is dissolved fully, the aqueous sodium hydroxide solution that adds 5mol/L in the ethanolic soln of saturated cardanol sulfonic acid, carry out neutralization reaction under 25 ℃, until the pH of reaction system is 7, remove by filter inorganic salt, 50 ℃, 133.3Pa underpressure distillation, obtain saturated cardanol sulfosalt surfactant.Temperature when dripping oleum on the impact of saturated cardanol sulfonate yield and active matter content as shown in Figure 2.When the temperature when dripping oleum was 10 ℃, its yield surpassed 80%, and active matter content is more than 95%.
Embodiment 2: accurately take saturated cardanol 10g and be dissolved in the 50mL methylene dichloride, slowly drip while stirring 10.5g under 10 ℃ and contain 20% free SO
3Oleum, after dropwising, be warming up under 25 ℃ and react 3h, underpressure distillation under 50 ℃, the condition of 133.3Pa obtains saturated cardanol sulfonic acid.With 50mL ethanol, saturated cardanol sulfonic acid is dissolved fully, the aqueous sodium hydroxide solution that adds 5mol/L in the ethanolic soln of saturated cardanol sulfonic acid, carry out neutralization reaction under 25 ℃, until the pH of reaction system is 7.5, remove by filter inorganic salt, 50 ℃, 133.3Pa underpressure distillation, get saturated cardanol sulfosalt surfactant.The time for adding of oleum on the impact of saturated cardanol sulfonate yield and active matter content as shown in Figure 3.When the oleum time for adding was 1 ~ 2h, its yield was all over 80%, and active matter content is all more than 80%.
Embodiment 3: accurately take saturated cardanol 10g and be dissolved in the 50mL methylene dichloride, slowly drip while stirring 10.5g under 10 ℃ and contain 20% free SO
3Oleum, time for adding is 2h, after dropwising, is warming up to and reacts under 25 ℃ 1 ~ 4 hour, underpressure distillation under 50 ℃, the condition of 133.3Pa obtains saturated cardanol sulfonic acid.With 50mL ethanol, saturated cardanol sulfonic acid is dissolved fully, the aqueous sodium hydroxide solution that adds 5mol/L in the ethanolic soln of saturated cardanol sulfonic acid, carry out neutralization reaction under 20 ~ 30 ℃, until the pH of reaction system is 7, remove by filter inorganic salt, 50 ℃, 133.3Pa underpressure distillation, get saturated cardanol sulfosalt surfactant.The sulfonation reaction time on the impact of saturated cardanol sulfonate yield and active matter content as shown in Figure 4.When the sulfonation time was 3h, its yield was 82.4%, and active matter content is 98.7%.
Embodiment 4: accurately take saturated cardanol 10g and be dissolved in the 50mL methylene dichloride, slowly drip while stirring 10.5g under 10 ℃ and contain 20% free SO
3Oleum, time for adding is 2h, dropwises, and is warming up under 25 ℃ to react 3h, underpressure distillation under 50 ℃, the condition of 133.3Pa gets saturated cardanol sulfonic acid.With 50mL ethanol, saturated cardanol sulfonic acid is dissolved fully, adding concentration in the ethanolic soln of saturated cardanol sulfonic acid is the aqueous sodium hydroxide solution of 3 ~ 7mol/L, carry out under 20 ~ 30 ℃ neutralization reaction and, until the pH of reaction system is 8, remove by filter inorganic salt, 50 ℃, 133.3Pa underpressure distillation, obtain saturated cardanol sulfosalt surfactant.In neutralization reaction, aqueous sodium hydroxide solution concentration on the impact of saturated cardanol sulfonate yield and active matter content as shown in Figure 5.When naoh concentration was 4.5 ~ 5.5mol/L, its yield was more than 80%, and active matter content is all more than 90%.
Embodiment 5: accurately take saturated cardanol 10g and be dissolved in the 50mL methylene dichloride, slowly drip while stirring 10.5g under 10 ℃ and contain 30% free SO
3Oleum, time for adding is 2h, dropwises, and is warming up under 25 ℃ to react 3h, underpressure distillation under 50 ℃, the condition of 133.3Pa obtains saturated cardanol sulfonic acid.With 50mL ethanol, saturated cardanol sulfonic acid is dissolved fully, the sodium hydroxide solution that adds 5mol/L in the ethanolic soln of saturated cardanol sulfonic acid, 20 ~ 30 ℃ carry out neutralization reaction and, until reaction system to pH be 7 ~ 8, remove by filter inorganic salt, 50 ℃, 133.3Pa underpressure distillation, get saturated cardanol sulfosalt surfactant.The pH of neutralization reaction termination system is as shown in table 2 on the impact of saturated cardanol sulfonate yield and active matter content.When system pH was 7 ~ 8, the yield of saturated cardanol sulfonate was more than 80%, and active matter content is more than 98%.
Table 1
| The pH value | 7 | 8 |
| Productive rate/% | 81.9 | 82.4 |
| Active matter content/% | 98.6 | 98.7 |
Embodiment 6: 2 ~ 5 data with reference to the accompanying drawings, and when the mass ratio of saturated cardanol and oleum is 1:1.05, free SO in oleum
3Concentration be 20 ~ 30%, time for adding is 2h, dropping temperature is 10 ℃, sulfonation temperature is 20 ~ 30 ℃, the sulfonation time is 3h; The aqueous sodium hydroxide solution concentration of neutralization reaction is 5mol/L, and the neutralization reaction temperature is 25 ℃, and when neutralization reaction stops, system pH is 7 o'clock, and the yield of the synthetic saturated cardanol sulfosalt surfactant that obtains is 82.4%, and active matter content is 98.7%.And the massfraction of this tensio-active agent in its aqueous solution is 0.3%, the sodium-chlor massfraction is 3.5%, when the sodium hydroxide massfraction is 1.2%, use Model500C type full-automatic rotating to drip interfacial tensimeter dynamic interface tension force between this aqueous solution and oily interface when measuring 45 ℃, the results are shown in Figure 6.Result shows, with this understanding, this tensio-active agent can be reduced to 2.19 * 10 with oil water interfacial tension
-4MN/m's is extremely low-level, thereby shows that this tensio-active agent has good interfacial activity.
Claims (1)
1. the aqueous solution of a saturated cardanol sodium sulfonate is characterized in that: wherein the massfraction of saturated cardanol sodium sulfonate is 0.3%, the sodium-chlor massfraction is 3.5%, the sodium hydroxide massfraction is 1.2%; The aqueous solution of this tensio-active agent can be with the interfacial tension lowering to 2.19 of profit * 10
-4MN/m.
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| CN104194847B (en) * | 2014-08-22 | 2016-04-13 | 常州中南化工有限公司 | A kind of slurries additive agent containing cardanol sulfonate and application thereof |
| CN108164632B (en) * | 2015-10-19 | 2020-06-09 | 甘肃杨何逸科技有限公司 | Modified cardanol derivative water reducing agent and preparation method thereof |
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| CN106987842B (en) * | 2017-04-24 | 2019-03-26 | 西安石油大学 | A kind of high temperature resistant corrosion inhibitor and preparation method thereof |
| CN107021890A (en) * | 2017-04-27 | 2017-08-08 | 西安石油大学 | A kind of preparation method for suppressing oil acid corrosion high-temperature corrosion inhibitor |
| CN109387600A (en) * | 2018-10-31 | 2019-02-26 | 广东丽臣奥威实业有限公司 | The measurement method of effective component in a kind of α olefin sulfonate product |
| CN109972222B (en) * | 2019-03-08 | 2021-12-03 | 裘建庆 | Purification method and application of sulfonate-containing surfactant |
| CN112662387A (en) * | 2020-11-30 | 2021-04-16 | 天津大港油田滨港集团博弘石油化工有限公司 | Green and environment-friendly surfactant oil displacement system for oil exploitation |
| WO2023233273A1 (en) * | 2022-05-31 | 2023-12-07 | 1/1Tata Chemicals Limited | Process for preparing a salt of 4-hydroxy pentadecyl benzene sulfonic acid |
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