CN106810471B - A kind of production method of petroleum sulfonate - Google Patents
A kind of production method of petroleum sulfonate Download PDFInfo
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- CN106810471B CN106810471B CN201510866750.1A CN201510866750A CN106810471B CN 106810471 B CN106810471 B CN 106810471B CN 201510866750 A CN201510866750 A CN 201510866750A CN 106810471 B CN106810471 B CN 106810471B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention discloses a kind of production methods of petroleum sulfonate, and this approach includes the following steps：After sulfonation, using the solvent insoluble in petroleum component as extractant, stratification after being extracted to sulfonation acid-soluble oil, upper layer is that raffinate oil returns to continuation sulfonation, is repeated the above process, until the arene content in raw material is dropped to 5% or less, lower layer is the extractant containing sulfonic acid, extractant is steamed by distillation, sulfonate can further be prepared by obtaining sulfonic acid, and the extractant steamed is recycled.This method is using the solvent insoluble in petroleum component as extractant, sulfonation acid-soluble oil is extracted, sulfonic acid after extraction and separation is directly neutralized into sulfonate, raffinate oil, which returns, continues sulfonation, because being free of sulfonic acid in raffinate oil, when being contacted again with sulfonating agent, would not acid sludge be become by sulfonation again, to achieve the purpose that improve sulfonate yield.
Description
Technical field
The present invention relates to sulfonate production fields, more specifically to a kind of production method of petroleum sulfonate.
Background technology
Petroleum sulfonate is a kind of widely used anion surfactant, is played in agent for improving oilfield recovery etc.
Important role.
Petroleum component is complicated mixture, is had a very wide distribution, containing a large amount of gum asphalt and polycyclic aromatic hydrocarbon etc.,
Contained aromatic hydrocarbons is because of structure difference sulfonation process and asynchronous, and with the progress of sulfonating reaction, the aromatic hydrocarbons of sulfonation at first is particularly easy to
Further sulfonation is more sulfonic acid, to influence the product quality of sulfonate, reduces the yield of petroleum sulfonate and generates to environment
The acid sludge of pollution.
To avoid the sulfonation excessively of sample, existing processing method from being roughly divided into two classes：The first kind passes through the improvement to equipment
Reduce the generation of acid sludge, as CN00240550, CN85109591, CN96107060, CN200510093638,
CN200520118134, CN200610028680, CN200610102153, CN201210262133, CN201320359754 etc.,
These methods are only capable of reducing the production quantity of acid sludge on a small quantity, are influenced on the raising of petroleum sulfonate yield limited.Second class is added molten
The method that dilution agent feedstock oil reduces acid sludge, CN201210384390 disclose a kind of by residual oil progress sulfonation preparation oil field sulphur
The method of Barbiturates surfactant proposes to avoid crossing sulfonation problem in residual oil sulfonation process first by residual oil and solvent
In mass ratio 1: 2~5 dilutions, then cool down, and after sulfonating agent is diluted with solvent in mass ratio 1: 1~3, take opposite residual oil addition
1/2~1/20 complexing agent be added residual oil in, 0.5~2h of aging, after being then gradually added into the dilution of 1~3 times of residual oil quality
Sulfonating agent is added alkali and is neutralized, and sedimentation removing bottom aqueous solution is distilled off solvent, petroleum sulfonate production finally can be obtained
Product.CN201210235703 is disclosed with SO3It is solvent, at a lower temperature sulfonation as sulfonating agent, aprotic alkyl halide
The method for preparing sulfonated humic acid.CN201010271259 and CN201310660630 discloses a kind of petroleum sulfonate surface
The preparation method of activating agent, this method are the crude oil fractions oil using 350~500 DEG C as raw material, with 60~120 DEG C of solvent naphthas, chlorine
It is diluent for aromatic hydrocarbons or chloralkane, using the sulfur trioxide of gas phase as sulfonating agent, and uses falling film reactor, pass through control
Purpose product is made in reaction temperature, aging temperature.CN 201210094872 discloses a kind of tapped oil alkylate sulfonation legal system
The method of standby surfactant, using catalytic cracked oil pulp or the alkylate of recycle oil tapped oil as raw material, with the concentrated sulfuric acid, hair
Cigarette sulfuric acid or SO3It carries out sulfonating reaction using petroleum ether, dichloroethanes, nitrobenzene as solvent for sulfonating agent and prepares sulfonate type table
Face activating agent.Although these above-mentioned methods make sulfonating conditions mitigate, but the acid sludge generated is present in dissolved state in acid-soluble oil,
The quality of sulfonate is affected, in addition, solvent such as halogenated hydrocarbons being added etc. not only damages greatly human body, atmospheric environment is destroyed tight
Weight will also cause the chloride ion corrosion during oil refining working process of downstream after being remained in oil.
Therefore, acid sludge yield is greatly lowered in exploitation one kind, and the method for sulfonating for improving aromatic hydrocarbons utilization rate in oil very must
It wants.
Invention content
It is an object of the invention to solve in petroleum sulfonate production process, acid sludge is easily generated to reduce sulfonation efficiency
The problem of, and then a kind of production method for the yield for preventing the excessive sulfonation of sulfonic acid, improving petroleum sulfonate is provided
The above-mentioned purpose of the present invention is achieved in that a kind of production method of petroleum sulfonate, includes the following steps：
It is extractant that solvent insoluble in petroleum component is added in sulfonating reaction, stratification after being extracted to sulfonation acid-soluble oil, on
Layer is that raffinate oil returns to continuation sulfonation, is repeated the above process, until the arene content in raw material is dropped to 5% hereinafter, lower layer is
Extractant containing sulfonic acid steams extractant by distillation, and sulfonate can further be prepared by obtaining sulfonic acid, and the extractant steamed is again
It recycles.
Petroleum sulfonate production method of the present invention, wherein the temperature of sulfonation the acid-soluble oil extraction and stratification
Preferably 30-70 DEG C of degree, when the extractant containing sulfonic acid distills, pressure is preferably 0~-0.08MPa, and temperature is preferably at 92 DEG C
Below.
Petroleum sulfonate production method of the present invention, wherein the extractant is preferably dimethyl carbonate, carbonic acid two
Ethyl ester or dithyl sulfate.
Petroleum sulfonate production method of the present invention, wherein the sulfonation process is particularly preferred as：Sulfonation raw material is
Petroleum component, sulfonating agent are the SO3 of 98% concentrated sulfuric acid, a concentration of 20% oleum or 3-5%, and sulfonating agent is former with sulfonation
Aromatic hydrocarbons molar ratio in material is 0.1-0.6：1, the volume ratio of sulfonation raw material and extractant is 1：0.2-2, reaction temperature 10-80
℃。
Petroleum sulfonate production method of the present invention, which is characterized in that the volume of the sulfonation raw material and extractant
Than being preferably 1：0.5-1.
Petroleum sulfonate production method of the present invention, which is characterized in that the sulfonating agent and the aromatic hydrocarbons in feedstock oil
Molar ratio is preferably 0.2-0.4：1.
Petroleum sulfonate production method of the present invention, which is characterized in that the reaction temperature is preferably 20-60 DEG C.
Petroleum sulfonate production method of the present invention, which is characterized in that in the petroleum component can sulfonation aromatic hydrocarbons
Content is preferably 10% or more.
Petroleum sulfonate production method of the present invention, which is characterized in that the petroleum component is preferably crude oil, straight run
Fraction, hydrofined oil or furfural extract oil.
Petroleum sulfonate production method of the present invention, which is characterized in that the sulfonating reaction mode be preferably autoclave,
Falling film type or atomizing.
The present invention is using the solvent insoluble in petroleum component as extractant, the sulfonic acid that will be generated during sulfonating reaction in time
It is detached after extraction, it is acid sludge by excessive sulfonation to avoid generated sulfonic acid to be detained in systems, to reduce the production of acid sludge
Raw amount, the yield of petroleum sulfonate are enhanced about more than once, and extractant continues sulfonation extraction reaction after distillation is handled.
Specific implementation mode
It further illustrates the present invention by the following examples, however, the present invention is not limited to these examples.
Embodiment 1：
In autoclave sulfonation reactor, input raw material is transformer oil furfural extract oil, saturated hydrocarbon content 31.58%, virtue
Fragrant hydrocarbon content 66.28%, gum asphaltic content 2.14% are 1 according to the volume ratio of sulfonation raw material and extractant：1 ratio
After dimethyl carbonate stirring is added, the oleum sulfonating agent that 20% is added under the conditions of 50 DEG C carries out sulfonating reaction, sulfonating agent
It is 0.4 with the aromatic hydrocarbons molar ratio in sulfonation raw material：1.After sulfonation, by sulfonation acid-soluble oil stratification, the temperature of separation is
50 DEG C, upper layer is the raffinate oil for removing sulfonic acid, and aromatic hydrocarbon content 45.26%, lower layer is the extractant containing sulfonic acid, by opposite
Pressure -0.02MPa distills at 85 DEG C of temperature and steams extractant, and obtaining sulfonic acid further neutralization can prepare sulfonate, steam
Extractant repeats the above process together with the raffinate oil of removing sulfonic acid back to xanthator that the reaction was continued, in second of raffinate oil
Arene content be 27.62%, the arene content in third time raffinate oil is 15.73%, and the aromatic hydrocarbons in the 4th raffinate oil contains
Amount is 8.54%, and the arene content in the 5th raffinate oil is 3.28%.After five sulfonation, the cumulative yield of acid sludge is
1.87%, the sum yield of sulfonate is 72.35%.
Embodiment 2：
In autoclave sulfonation reactor, input raw material is paraffinic base crude oil, wax content：5.42%, gum level：
6.79%, asphalt content：0.58%, arene content：23.52%, it is 1 according to the volume ratio of sulfonation raw material and extractant：2 add
After entering diethyl carbonate stirring, the concentrated sulfuric acid for being added 98% carries out sulfonating reaction, sulfonating agent and sulfonation raw material under the conditions of 10 DEG C
In aromatic hydrocarbons molar ratio be 0.1：1, after sulfonation, the temperature by sulfonation acid-soluble oil stratification, separation is 15 DEG C, and upper layer is
The raffinate oil of sulfonic acid is removed, aromatic hydrocarbon content 20.56%, lower layer is the extractant containing sulfonic acid, by relative pressure-
0.04MPa distills at 72 DEG C of temperature and steams extractant, and obtaining sulfonic acid further neutralization can prepare sulfonate, the extraction steamed
Agent returns to xanthator together with the raffinate oil of removing sulfonic acid, and sulfonating agent is 0.3 with the aromatic hydrocarbons molar ratio in sulfonation raw material：1,
Repeating the above process that the reaction was continued, the arene content in second of raffinate oil is 15.43%, steams extractant by distillation,
Obtaining sulfonic acid further neutralization can prepare sulfonate, and the extractant steamed fills together with the raffinate oil of removing sulfonic acid back to sulfonation
It sets, sulfonating agent is 0.6 with the aromatic hydrocarbons molar ratio in sulfonation raw material：1, repeat the above process that the reaction was continued, in third time raffinate oil
Arene content be 7.89%, repeat the above process that the reaction was continued, the arene content in the 4th raffinate oil is 2.14%, is passed through
After four sulfonation, the cumulative yield of acid sludge is 1.28%, and the sum yield of sulfonate is 25.37%.
Embodiment 3：
Falling film sulfonation reactor, raw material are naphthenic base second line of distillation, and saturated hydrocarbon content 70.82% in raw material, aromatic hydrocarbon contains
Amount 20.82%, gum asphaltic content 8.36% are 1 according to the volume ratio of sulfonation raw material and extractant：0.2 ratio is added
After dithyl sulfate stirring, the gas phase sulfur trioxide sulfonating agent with 5% under the conditions of 80 DEG C carries out sulfonating reaction, sulfonating agent and sulphur
It is 0.6 to change the aromatic hydrocarbons molar ratio in raw material：1.After sulfonation, the temperature by sulfonation acid-soluble oil stratification, separation is 70 DEG C,
Upper layer is the raffinate oil for removing sulfonic acid, and aromatic hydrocarbon content 10.67%, lower layer is the extractant containing sulfonic acid, by 92 DEG C of normal pressure
Distillation, extractant is steamed, and obtaining sulfonic acid further neutralization can prepare sulfonate, the raffinate of the extractant steamed and removing sulfonic acid
Oil repeats the above process that the reaction was continued back to xanthator together, and the arene content in second of raffinate oil is 4.38%, is passed through
After crossing secondary sulfonation, the cumulative yield of acid sludge is 0.96%, and the sum yield of sulfonate is 21.74%.
Embodiment 4：
It sprays sulfonation reactor, input raw material is paraffinic base subtract three line, saturated hydrocarbon content 89.63%, aromatic hydrocarbon content
9.53%, gum asphaltic content 0.84% is 1 according to the volume ratio of sulfonation raw material and dimethyl carbonate：0.5 ratio is added
Dimethyl carbonate stirring after, be passed through under the conditions of 40 DEG C 5% gas phase sulfur trioxide sulfonating agent carry out sulfonating reaction, sulfonating agent with
Aromatic hydrocarbons molar ratio in sulfonation raw material is 0.2：1.After sulfonation, the temperature by sulfonation acid-soluble oil stratification, separation is 40
DEG C, upper layer is the raffinate oil for removing sulfonic acid, and aromatic hydrocarbon content 7.56%, lower layer is the extractant containing sulfonic acid, by opposite pressure
Power -0.08MPa distills under temperature 45 C and steams extractant, and obtaining sulfonic acid further neutralization can prepare sulfonate, the extraction steamed
Taking agent to be repeated the above process back to xanthator together with the raffinate oil for removing sulfonic acid, the reaction was continued, in second of raffinate oil
Arene content is 5.89%, and the arene content in third time raffinate oil is 3.24%, and after sulfonation three times, the accumulation of acid sludge is produced
Rate is 0.64%, and the sum yield of sulfonate is 10.71%.
Comparative example 1：
It sprays sulfonation reactor, input raw material is paraffinic base subtract three line, saturated hydrocarbon content 89.63%, aromatic hydrocarbon content
9.53%, gum asphaltic content 0.84%, be passed through under the conditions of 40 DEG C 5% gas phase sulfur trioxide sulfonating agent carry out sulfonation it is anti-
It answers, sulfonating agent is 0.6 with the aromatic hydrocarbons molar ratio in sulfonation raw material.After sulfonation, sulfonation acid-soluble oil is subjected to neutralization extraction, acid
Slag yield is 6.49%, and the yield of sulfonate is 4.32%.
Certainly, the present invention can also have other various embodiments, without deviating from the spirit and substance of the present invention, ripe
Various corresponding change and deformations, but these corresponding change and deformations can be made according to the present invention by knowing those skilled in the art
It should all belong to the scope of protection of the present invention.
Claims (8)
1. a kind of production method of petroleum sulfonate, which is characterized in that include the following steps：It is added and does not dissolve in sulfonating reaction
The solvent of petroleum component is extractant, and stratification after being extracted to sulfonation acid-soluble oil, upper layer is that raffinate oil returns to continuation sulphur
Change, repeat the above process, until the arene content in raw material is dropped to 5% hereinafter, lower layer is the extractant containing sulfonic acid, by steaming
It evaporates and steams extractant, sulfonate can further be prepared by obtaining sulfonic acid, and the extractant steamed is recycled；
The extractant is dimethyl carbonate, diethyl carbonate or dithyl sulfate；The volume ratio of sulfonation raw material and extractant is
1：0.5-1.
2. petroleum sulfonate production method according to claim 1, which is characterized in that sulfonation acid-soluble oil extraction and quiet
Set layering temperature be 30-70 DEG C, it is described containing sulfonic acid extractant distillation when, pressure be 0~-0.08MPa, temperature 92 DEG C with
Under.
3. petroleum sulfonate production method according to claim 1 or 2, which is characterized in that the sulfonation process is specially：
Sulfonation raw material is petroleum component, and sulfonating agent is the SO of 98% concentrated sulfuric acid, a concentration of 20% oleum or 3-5%3, sulfonation
Agent is 0.1-0.6 with the aromatic hydrocarbons molar ratio in sulfonation raw material：1, reaction temperature is 10-80 DEG C.
4. petroleum sulfonate production method according to claim 3, which is characterized in that in the sulfonating agent and feedstock oil
Aromatic hydrocarbons molar ratio is 0.2-0.4：1.
5. petroleum sulfonate production method according to claim 3, which is characterized in that the reaction temperature is 20-60 DEG C.
6. petroleum sulfonate production method according to claim 3, which is characterized in that can sulfonation in the petroleum component
Arene content is 10% or more.
7. petroleum sulfonate production method according to claim 3, which is characterized in that the petroleum component is crude oil, directly
Fraction, hydrofined oil or furfural extract oil.
8. petroleum sulfonate production method according to claim 3, which is characterized in that the sulfonating reaction mode is kettle
Formula, falling film type or atomizing.
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| CN108745291A (en) * | 2018-08-13 | 2018-11-06 | 宁夏然尔特工业产业研究院（有限公司） | A kind of biomass carbon and its application based on furfural dregs |
| CN109265376B (en) * | 2018-10-22 | 2021-07-02 | 克拉玛依市先进能源技术创新有限公司 | Method and device for continuously producing petroleum sulfonate |
| CN109824552A (en) * | 2019-01-28 | 2019-05-31 | 高路生 | A kind of petroleum sulfonate and preparation method thereof |
| CN114088797B (en) * | 2021-11-09 | 2024-06-11 | 中国石油大学(北京) | Sulfonation method and analysis method of aromatic hydrocarbon compounds in petroleum products |
| CN115974731A (en) * | 2022-12-02 | 2023-04-18 | 国家能源集团宁夏煤业有限责任公司 | Co-production process method and system of alpha-olefin sulfonate and alkane solvent oil |
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| CN1327979A (en) * | 2001-06-27 | 2001-12-26 | 秦立君 | Process for preparing petroleum sulfonate used in oil field |
| CN1379076A (en) * | 2001-04-06 | 2002-11-13 | 天津开发区鑫淼工贸有限公司 | Process for preparing petroleum sulfonate dedicated for tertiary recovery of petroleum |
| CN101659861A (en) * | 2008-08-29 | 2010-03-03 | 中国石油天然气股份有限公司 | Method for preparing petroleum sulfonate oil displacement agent |
| CN102872750A (en) * | 2012-09-29 | 2013-01-16 | 胜利油田中胜环保有限公司 | Residual oil sulfonation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1379076A (en) * | 2001-04-06 | 2002-11-13 | 天津开发区鑫淼工贸有限公司 | Process for preparing petroleum sulfonate dedicated for tertiary recovery of petroleum |
| CN1327979A (en) * | 2001-06-27 | 2001-12-26 | 秦立君 | Process for preparing petroleum sulfonate used in oil field |
| CN101659861A (en) * | 2008-08-29 | 2010-03-03 | 中国石油天然气股份有限公司 | Method for preparing petroleum sulfonate oil displacement agent |
| CN102872750A (en) * | 2012-09-29 | 2013-01-16 | 胜利油田中胜环保有限公司 | Residual oil sulfonation method |
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