CN105272916B - A kind of new rosin base imidazoline corrosion inhibitor - Google Patents
A kind of new rosin base imidazoline corrosion inhibitor Download PDFInfo
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- CN105272916B CN105272916B CN201510064954.3A CN201510064954A CN105272916B CN 105272916 B CN105272916 B CN 105272916B CN 201510064954 A CN201510064954 A CN 201510064954A CN 105272916 B CN105272916 B CN 105272916B
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Abstract
The present invention relates to the compound synthesis and applied technical field for anticorrosive metal, a kind of new rosin base imidazolines and its synthetic method and application are specifically disclosed.The starting material of Rosin-based Imidazoline class compound of the invention is rosin acid, and raw material is single, and synthetic route is easy to operate.The method that the compound synthesized is prepared corrosion inhibiter is simple, the compound only need to be dissolved in dimethylformamide, then acquired solution is dissolved in the water, add hydroxy ethylene diphosphonic acid, stir evenly to obtain the final product.This corrosion inhibiter safety and environmental protection simultaneously has excellent corrosion mitigating effect.It can be used for oil gas field surface gathering and transferring and storage and transportation pipeline, prevent destruction of the etchant gas to metal materials such as steels, reduce corrosion losses.
Description
Technical field
The present invention relates to the compound synthesis and applied technical field for anticorrosive metal, and in particular to a kind of novel pine
Perfume base imidazolines and its synthetic method and application, the compound can be used as corrosion inhibiter for oil, gas well liquid loading, manage
Anti-corrosion of metal in road transportational process.
Background technique
In recent decades, the oil gas field phase of a variety of corrosive mediums such as sulfide hydrogen, carbon dioxide and highly mineralized formation brines
After appearance.The heavy corrosion of oil gas field equipment, has had attracted more and more attention from people under acidic environment.The corrosion of oil gas field is not
Only huge economic loss is caused, while also directly threaten the living environment and body of the mankind to the exploitation of oil gas field, production
Health.As it can be seen that reinforcing corrosion and protection technical research, implements effectively to monitor and safeguard measure is to the open source section for producing industry
Stream, increases production and improves productivity and is of great significance.
It is a kind of economical and effective and practical anti-corrosion method that corrosion inhibiter is added in corrosive medium, in numerous corrosion inhibiter kinds
In, imidazoline corrosion inhibitor with high-efficiency low-toxicity, without specific stimulation smell, environmental pollution is small the advantages that and be quite popular.Imidazoles
For quinoline class corrosion inhibiter as a kind of simply environmentally friendly corrosion inhibiter of preparation process, application range is very extensive.For synthesizing miaow
The organic acid various types of oxazolines corrosion inhibiter, but natural material is fewer, and China is as rosin production and big export country, naturally
Rosin is resourceful, cheap, synthesizes corrosion inhibiter with it and practice of putting into production will have very big social benefit and economic effect
Benefit.The unique tricyclic diterpene molecular structure of abietyl will make the Rosin-based Imidazoline produced have better inhibition efficiency.It is existing
Have in technology there is not yet relevant report.
Summary of the invention
For the deficiencies in the prior art, the first purpose of this invention is the provision of shown in a kind of formula (4)
Rosin-based Imidazoline class compound:
Second has been designed to provide a kind of synthetic method of Rosin-based Imidazoline class compound shown in above-mentioned formula (4),
Series of compounds inventor synthesizes and confirms for the first time.
The object of the invention is achieved by the following technical programs.
A kind of synthetic method of Rosin-based Imidazoline class compound shown in formula (4), its step are as follows:
Step a: by rosin acid and K2CO3It is dissolved in dimethylformamide, is added iodomethane (MeI), stir 3 hours, TLC
Contact plate fully reacting.Vacuum rotary steam removes MeI, is extracted with ethyl acetate (EA), and concentration, washing removes dimethylformamide, has
Machine layer is washed with saturated sodium-chloride, dried, is concentrated, and remaining ingredient crosses silica gel with ethyl acetate (EA)/petroleum ether (PE) of 1:10
Pillar obtains formula (2) compound after purification, and reaction equation is as follows:
Step b: under the conditions of 0-10 DEG C, ethylenediamine and trimethyl aluminium (AlMe are added into toluene3), it is uniformly mixed, then
Formula (2) compound that step a is obtained is added, reflux 12 hours is sufficiently stirred.It is cooled to 0 DEG C, filtering, filtrate is extracted with ethyl acetate
It takes, organic layer is dry with sodium sulphate, is concentrated, and product silica gel column chromatography is purified (petrol ether/ethyl acetate=1/1), and formula is obtained
(3) compound is white solid, and reaction equation is as follows:
Step c: adding MeI after compound (3) and potassium carbonate is added in DMF, is sufficiently stirred 8 hours under room temperature, so
After filter, filtrate is concentrated to give crude product, then crude product HPLC is purified to obtain target product (4), be white solid.
Third object of the present invention is the provision of a kind of corrosion inhibiter for containing formula (4) compound, and the corrosion inhibiter is main
Anti-corrosion of metal for oil, gas well liquid loading, during pipeline transportation.New rosin base imidazoline inhibitor of the invention is nontoxic,
Inhibition efficiency is high, can reach 90% or more.Corrosion inhibiter of the invention is specifically formulated are as follows:
Above-mentioned formula corrosion inhibiter the preparation method comprises the following steps: formula (4) compound is first dissolved in dimethylformamide (DMF), obtain
Solution, then acquired solution is dissolved in the water, it adds hydroxy ethylene diphosphonic acid, stirs evenly to obtain the final product.
This corrosion inhibiter can be used for oil gas field surface gathering and transferring and storage and transportation pipe-line system, prevent etchant gas to metals such as steels
The destruction of material reduces corrosion losses.
Compared with prior art, the advantages and beneficial effects of the present invention are:
1, Rosin-based Imidazoline class compound, which is used as corrosion inhibiter, not only has good anti-H2S/CO2The corrosion inhibition of corrosion,
Simultaneously have many advantages, such as thermal stability is good, toxicity is low, without specific stimulation smell.The unique tricyclic diterpene molecular structure of abietyl,
New rosin base imidazoline inhibitor is nontoxic, and corrosion inhibition rate is high, can reach 90%.Rosin-based Imidazoline is imitated with better inhibition
Rate is mainly used for oil, gas well liquid loading, the anti-corrosion of metal during pipeline transportation.
2, the synthesis material of Rosin-based Imidazoline class compound of the invention is single, and synthetic route is easy to operate.
3, the method for preparing corrosion inhibiter according to inventive formulation is simple, only formula (4) compound need to be dissolved in dimethyl methyl
Amide (DMF) is re-dissolved in water after dissolution completely, is eventually adding hydroxy ethylene diphosphonic acid and stirs evenly to obtain the final product.While this
Corrosion inhibiter safety and environmental protection has excellent corrosion mitigating effect.It can be used for oil gas field surface gathering and transferring and storage and transportation pipeline, prevent corrosion gas
Destruction of the body to metal materials such as steels reduces corrosion losses.
Specific embodiment
The present invention is described in further detail combined with specific embodiments below.
Unless otherwise indicated, herein presented percentage is all mass percentage.
Embodiment 1:
A kind of synthetic method of formula (4) compound, its step are as follows:
Step a: the synthesis of formula (2) compound:
By 100g rosin acid (0.331mol) and 69g K2CO3(0.497mol) is dissolved in 800ml solvent dimethylformamide
In, 56.4 grams of (0.397mol) MeI are added, stir contact plate confirmation fully reacting in 3 hours.Vacuum rotary steam removes MeI, is extracted with EA
It takes, be concentrated, DMF solvent is removed in washing, and organic layer is washed with saturated sodium-chloride, dried, is concentrated, the EA/ of remaining ingredient 1:10
PE crosses silicon gel column and obtains 100g formula (2) compound after purification.
1H NMR(CDCl3,400MHz):0.75(m,7H)；0.94(m,6H)；1.18(m,7H)；1.50(m,4H),1.73
(m,6H)；2.01(m,4H)；2.14(m,1H)；3.55(s,3H)；5.29(d,1H)；5.70(s,1H).
Step b: the synthesis of formula (3) compound:
Under the conditions of 0-10 DEG C, 57.0g (0.949mol) ethylenediamine and 0.949molAlMe are added into 1L toluene3, mix
It closes uniformly, adds 100g (0.123mol) formula (2) compound that step a is obtained, reflux 12 hours is sufficiently stirred.It is cooled to 0
DEG C, filtering, filtrate is extracted with ethyl acetate, and organic layer is dry with sodium sulphate, concentration, and product silica gel column chromatography purifies (petroleum
Ether/ethyl acetate=1/1) white solid 17g is obtained, be formula (3) compound:
1H NMR:(CDCl3,400MHz):0.88(m,9H)；1.00(m,6H)；1.28(m,10H)；1.66(m,4H),
1.80(m,5H)；2.08(m,4H)；2.20(m,1H)；5.38(d,1H)；5.77(s,1H).
Step c: the synthesis of formula (4) compound:
It is added after 61.36mmol (20g) compound (3) and potassium carbonate 61.36mmol (8.46g) again in the DMF of 200mL
122.7mmol (17.42g) MeI is added, is sufficiently stirred 8 hours under room temperature, then filters, filtrate is concentrated to give crude product,
Crude product HPLC is purified again to obtain target product (4), 6.5g white solid.
1H NMR:(DMSO,400MHz):0.85(m,3H)；1.04(m,6H)；1.23(m,2H)；1.30(m,3H),1.58
(m,3H)；1.92(m,6H)；1.95(m,3H)；2.10(m,1H)；2.98(s,3H)；3.26(m,2H)；3.44(m,2H)；5.39
(s,1H)；5.77(s,1H).
Embodiment 2:
Firstly, formula made from embodiment 1 (4) compound is prepared into corrosion inhibiter, the corrosion inhibiter by formula (4) compound,
Dimethylformamide, hydroxy ethylene diphosphonic acid and water composition, concrete content range are as follows:
More specifically, each corrosion inhibitor formula is as shown in table 1 below:
The test of 1 corrosion inhibitor formula of table
| Number | Formula (4) compound (mg/L) | DMF(g/L) | Hydroxy ethylene diphosphonic acid (g/L) | Water |
| Formula 1 | 15 | 5.0 | 0.5 | Surplus |
| Formula 2 | 30 | 7.5 | 0.75 | Surplus |
| Formula 3 | 45 | 10.0 | 1.0 | Surplus |
| Formula 4 | 60 | 5.0 | 0.5 | Surplus |
| Formula 5 | 75 | 7.5 | 0.75 | Surplus |
| Formula 6 | 90 | 10.0 | 1.0 | Surplus |
The preparation method for the corrosion inhibiter being respectively formulated above is as follows: formula (4) compound being first dissolved in dimethylformamide
(DMF), it then by acquired solution is dissolved in the water, stirs evenly after adding hydroxy ethylene diphosphonic acid up to corrosion inhibiter.
Inhibition efficiency measures under the conditions of acid:
According to SY/T 5405-1996 " acidification corrosion inhibiter method for testing performance and evaluation index ", have by test simulation
Body illustrates corrosion mitigating effect of formula prepared by the present invention (4) compound as corrosion inhibiter, is shown in Table 2.
Table 2
The density of corrosion inhibitor metering being respectively formulated in table 2 is in terms of the corrosion inhibiter that the formula of table 1 prepares.
The unique tricyclic diterpene molecular structure of abietyl, new rosin base imidazoline inhibitor is nontoxic, and corrosion inhibition rate is high, can reach
To 98% or more.Rosin-based Imidazoline has better inhibition efficiency, is mainly used for oil, gas well liquid loading, during pipeline transportation
Anti-corrosion of metal.
The specific embodiments described in this specification only illustrate that spirit of the invention.Skill belonging to the present invention
The technical staff in art field can make various modifications or additions to the described embodiments or using similar side
Formula substitution, however, it does not deviate from the spirit of the invention or beyond the scope of the appended claims.
Claims (3)
1. a kind of synthetic method of Rosin-based Imidazoline class compound shown in formula (4), includes the following steps:
Step a: by rosin acid and K2CO3It is dissolved in dimethylformamide, iodomethane is added, vacuum rotary steam removes after fully reacting
Iodomethane is extracted with ethyl acetate, and concentration, washing removes dimethylformamide, organic layer washs with saturated sodium-chloride, dried,
Concentration, remaining ingredient cross silicon gel column with the ethyl acetate/petroleum ether of 1:10 and obtain formula (2) compound after purification, and reaction equation is such as
Under:
Step b: under the conditions of 0-10 DEG C, ethylenediamine and trimethyl aluminium are added into toluene, is uniformly mixed, adds step a and obtain
Formula (2) compound arrived, is sufficiently stirred back flow reaction, is cooled to 0 DEG C, filtering, filtrate is extracted with ethyl acetate, organic layer sulphur
Sour sodium is dry, is concentrated, and product is purified with silica gel column chromatography, obtains formula (3) compound, reaction equation is as follows:
Step c: iodomethane is added after compound (3) and potassium carbonate is added in dimethylformamide, is sufficiently stirred 8 under room temperature
Hour, it then filters, filtrate is concentrated to give crude product, then crude product HPLC is purified to obtain target product (4), reaction equation
It is as follows:
2. a kind of corrosion inhibiter of the Rosin-based Imidazoline class compound containing the synthesis of synthetic method described in claim 1.
3. corrosion inhibiter according to claim 2, which is characterized in that the formula of the corrosion inhibiter is as follows:
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| CN108727268B (en) * | 2017-04-20 | 2020-08-07 | 中国石油天然气股份有限公司 | Rosin imidazoline quaternary ammonium salt compound, corrosion inhibitor and preparation method |
| CN112048722A (en) * | 2020-09-01 | 2020-12-08 | 武汉思越化学技术有限公司 | Preparation method and preparation system of special corrosion inhibitor for metal equipment |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101687812A (en) * | 2007-07-02 | 2010-03-31 | 弗·哈夫曼-拉罗切有限公司 | The 2-imidazolinium compounds that trace amine associated receptors (TAAR) is had good affinity |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101687812A (en) * | 2007-07-02 | 2010-03-31 | 弗·哈夫曼-拉罗切有限公司 | The 2-imidazolinium compounds that trace amine associated receptors (TAAR) is had good affinity |
Non-Patent Citations (5)
| Title |
|---|
| Corrosion and Corrosion Inhibition Behavior of N80 and P110 Carbon Steels in CO2-Saturated Simulated Formation Water by Rosin Amide Imidazoline;P. C. Okafor，等;《Ind. Eng. Chem. Res.》;20110427;第50卷(第12期);第7273-7281页，第7273页，第7274页表格3，第7280-7281页结论部分 * |
| Mechanistic Studies of the Corrosion Inhibitor Oleic Imidazoline;A. Edwards, et al;《Corrosion Science》;19940228;第36卷(第2期);第315-325页，第318页图3，第319页表1，第319页末段-320页首段 * |
| Novel imidazoline compounds as partial or full agonists of D2-like dopamine receptors inspired by I2-imidazoline binding sites ligand 2-BFI;Gianfabio Giorgioni, et al;《Bioorganic & Medicinal Chemistry》;20100806;第18卷;第7085-7091页，第7088页第5.1.5节 * |
| Rosin-based acid anhydrides as alternatives to petrochemical curing agents;Xiaoqing Liu, et al;《Green Chem.》;20090417;第11卷;第1018–1025页，第1020页右栏第2段和图2 * |
| 水溶性松香基咪唑啉的合成及缓蚀性能;周永红，等;《林产化学与工业》;20031231;第23卷(第4期);第7-10页 * |
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