CN104817193A - Water treatment corrosion inhibitor and preparation method thereof - Google Patents
Water treatment corrosion inhibitor and preparation method thereof Download PDFInfo
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Abstract
The invention provides a water treatment corrosion inhibitor and a preparation method thereof. The water treatment corrosion inhibitor is an imidazoline quaternary ammonium salt. The preparation method comprises a step of subjecting an imidazoline compound and a quaternization reagent to a salt forming reaction so as to produce the imidazoline quaternary ammonium salt; the imidazoline compound is synthesized through a reaction of organic carboxylic acid with organic polyether polyamine; and the quaternization reagent is one or a mixture of more than one selected from the group consisting of dimethyl carbonate, diethyl carbonate and ethylene carbonate. The salt forming reaction comprises the following concrete steps: adding the imidazoline compound and a solvent into a reactor, adding the quaternization reagent into the reactor drop by drop under a stirring condition and carrying out a reaction for 1 to 4 h as reaction temperature is controlled to be 60 to 90 DEG C; and carrying out heating to 95 to 120 DEG C, carrying out a reaction for 3 to 10 h and then carrying out cooling so as to obtain the imidazoline quaternary ammonium salt. The method provided by the invention accords with requirements of the green chemical industry, has low toxicity during synthesis and is simple and convenient to operate; post-treatment of the obtained water treatment corrosion inhibitor is convenient; and the obtained water treatment corrosion inhibitor has excellent corrosion inhibition performance.
Description
Technical field
the present invention relates to a kind of water treatment corrosion inhibitors and preparation method thereof.
Background technology
imidazoline Quatemary-ammonium-salt Corrosion Inhibitor is good water-soluble due to it, is widely used in water treatment corrosion inhibitors field, is mainly used as corrosion inhibitor for oil field, sterilant, restrainer, tensio-active agent, clean-out system etc.At present, a lot of to the synthesis report of imidazoline quaternary ammonium salt both at home and abroad, when quaternized to tetrahydroglyoxaline, adopt Benzyl Chloride, methyl-sulfate, epoxy chloropropane etc. as quaternizing agent, these reagent toxicities are strong, volatile more, not easy to operate, endanger greatly to producers, unfriendly to environment.The preparation method of a kind of metal inhibitor disclosed in: the preparation method of a kind of alkyl imidazoline quaternary ammonium salt disclosed in Chinese patent application 200910305443.0 and Chinese patent application 201110060385.7, adopt Benzyl Chloride or Mono Chloro Acetic Acid as quaternizing agent in aforesaid method, not only there is toxicity, and easily produce the problem of the anticaustic that halide-ions brings.
Summary of the invention
for the problems referred to above, an object of the present invention is under the prerequisite ensureing water treatment corrosion inhibitors sustained release performance, provides a kind of synthesis technique easy, the preparation method of the water treatment corrosion inhibitors of production process environmental protection; Two of object of the present invention is to provide a kind of novel water treatment corrosion inhibitors, and its corrosion inhibition is better.
for achieving the above object, a kind of technical scheme that the present invention adopts is as follows:
a kind of preparation method of water treatment corrosion inhibitors, described water treatment corrosion inhibitors is imidazoline quaternary ammonium salt, described method comprises the step making imidazolines and quaternizing agent generation salt-forming reaction generate described imidazoline quaternary ammonium salt, described quaternizing agent is one or more the combination in methylcarbonate, diethyl carbonate, ethylene carbonate, described salt-forming reaction is implemented as follows: join in reactor by imidazolines and solvent, under the condition stirred, control temperature of reaction 60 ~ 90 DEG C, quaternizing agent is added drop-wise in reactor, reaction 1 ~ 4h; Then be warming up to 95 ~ 120 DEG C, reaction 3 ~ 10h, cools and obtains described imidazoline quaternary ammonium salt.
preferably, the structural formula of described imidazolines is as follows:
in above formula, R is selected from the one in pentadecyl, heptadecyl, 17 carbon-9-thiazolinyls, tridecyl, undecyl, nonyl, hexyl; N=4 ~ 8.
preferably, described solvent is alcoholic solvent.Further, described solvent is preferably selected from one or more the combination in ethanol, ethylene glycol, n-propyl alcohol, Virahol, propyl carbinol, sec-butyl alcohol.
further, the molar ratio of described imidazolines and quaternizing agent is 1:(0.6 ~ 1.4).The quality summation of imidazolines and quaternizing agent and the mass ratio of solvent are 1:0.5 ~ 1.5.
further, described method also comprises the step preparing imidazolines, and this step comprises:
mol ratio is 1:(0.6 ~ 1.3 by amidate action: under nitrogen protection) organic carboxyl acid and organic polyether polyamine mixing, control temperature 90 ~ 110 DEG C, pressure 0.1 ~ 0.2MPa, reaction 1 ~ 4h, isolate amidate action generate water;
cyclization: the temperature 150 ~ 200 DEG C controlling the system after amidate action, pressure 0.2 ~ 0.6MPa, reaction 3 ~ 8h, then control temperature 200 ~ 250 DEG C, pressure 0.6 ~ 0.8MPa, reaction 1 ~ 3h, isolate water in reaction system and the complete raw material of unreacted, cooling obtains described imidazolines.
the preparation reaction equation of imidazolines is expressed as follows:
preferably, described organic carboxyl acid is one or more the combination in Palmiticacid, stearic acid, oleic acid, myristic acid, lauric acid, capric acid, phenylformic acid.
preferably, described organic polyether polyamine is for being selected from NH
2
c
2
h
4
nH (C
2
h
4
o)
4
h, NH
2
c
2
h
4
nH (C
2
h
4
o)
6
h, NH
2
c
2
h
4
nH (C
2
h
4
o)
8
one or more combination in H.
the another technical scheme that the present invention takes is: a kind of water treatment corrosion inhibitors, and it is the imidazoline quaternary ammonium salt be shown below,
wherein, a=1 and b=2 or 3, or a=2 and b=5;
n=4~8。
the present invention adopts above technical scheme, and tool has the following advantages: the present invention adopts quaternizing agent toxicity low, without sharp aroma, meet the requirement of green chemical industry, building-up process low toxicity, easy and simple to handle, product convenient post-treatment, and not halogen-containing element, product can not produce halogen ion etching phenomenon; And the organic polyether polyamine in raw material makes the better water-soluble of imidazoline quaternary ammonium salt product.Water treatment corrosion inhibitors of the present invention can be obtained by the explained hereafter of simple, low toxicity, easily control, and water treatment corrosion inhibitors has excellent water-soluble and corrosion inhibition, has broad application prospects.
Embodiment
below preferred embodiment of the present invention is described in detail, can be easier to make advantages and features of the invention be those skilled in the art will recognize that thus make more explicit defining to protection scope of the present invention.The implementation condition adopted in embodiment can do further adjustment according to specific requirement, and not marked implementation condition is generally the condition in normal experiment.
imidazoline quaternary ammonium salt in following embodiment 1 to 9 is all by following route synthesis:
wherein, R is selected from pentadecyl, heptadecyl, 17 carbon-9-thiazolinyls, tridecyl, undecyl, nonyl, phenmethyl;
a=1 and b=2 or b=3, or a=2, b=5;
n=4~8。
embodiment 1
step one: the synthesis of imidazolines
amidate action, under nitrogen protection, to adding the Palmiticacid and polyether polyamine NH that mol ratio is 1:1.1 in the four-hole bottle reactor of thermometer, agitator, prolong and water trap
2
c
2
h
4
nH (C
2
h
4
o)
4
h also stirs, and is warming up to 100 DEG C and reduces pressure to make vacuum tightness be 0.1MPa in 0.5h, continues reaction 0.5h, isolates the water that amidate action generates;
cyclization, in 5h by the temperature of above-mentioned reactor from 100 DEG C slowly rise to 200 DEG C, vacuum tightness is slowly increased to 0.6MPa, steam the water that cyclization generates, then insulation at 200 DEG C, control vacuum tightness is 0.75MPa, continues reaction 1h, steams moisture unnecessary in reaction system and the complete raw material of unreacted, finally reactant is cooled, obtain imidazolines.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and isopropanol solvent, mechanical stirring, at 80 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:0.6, reactant (imidazolines, methylcarbonate) is 1:1 with the mass ratio of isopropanol solvent, stirring reaction 3h; Be warming up to 100 DEG C ~ 110 DEG C, reaction 6h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 2
step one: the synthesis of imidazolines
synthetic method is with embodiment one.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and isopropanol solvent, mechanical stirring, at 80 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:0.8, reactant (imidazolines, methylcarbonate) is 1:1 with the mass ratio of isopropanol solvent, stirring reaction 3h; Be warming up to 100 DEG C ~ 110 DEG C, reaction 6h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 3
step one: the synthesis of imidazolines
synthetic method is with embodiment one.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and isopropanol solvent, mechanical stirring, at 80 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:1, reactant (imidazolines, methylcarbonate) is 1:1 with the mass ratio of isopropanol solvent, stirring reaction 3h; Be warming up to 100 DEG C ~ 110 DEG C, reaction 6h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 4
step one: the synthesis of imidazolines
synthetic method is with embodiment one.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and isopropanol solvent, mechanical stirring, at 80 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:1.2, reactant (imidazolines, methylcarbonate) is 1:1 with the mass ratio of isopropanol solvent, stirring reaction 3h; Be warming up to 100 DEG C ~ 110 DEG C, reaction 6h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 5
step one: the synthesis of imidazolines
synthetic method is with embodiment one.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and isopropanol solvent, mechanical stirring, at 80 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:1.4, reactant (imidazolines, methylcarbonate) is 1:1 with the mass ratio of isopropanol solvent, stirring reaction 3h; Be warming up to 100 DEG C ~ 110 DEG C, reaction 6h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 6
step one: the preparation of imidazolines
amidate action, under nitrogen protection, to adding the oleic acid and polyether polyamine NH that mol ratio is 1:0.6 in the four-hole bottle reactor of thermometer, agitator, prolong and water trap
2
c
2
h
4
nH (C
2
h
4
o)
4
h also stirs, and is warming up to 90 DEG C and reduces pressure to make vacuum tightness be 0.1MPa in 1h, continues reaction 3h, isolates the water that amidate action generates;
cyclization, in 8h by the temperature of above-mentioned reactor from 90 DEG C slowly rise to 150 DEG C, vacuum tightness is slowly increased to 0.2MPa, steam the water that cyclization generates, then insulation at 150 DEG C, control vacuum tightness is 0.6MPa, continues reaction 3h, steams moisture unnecessary in reaction system and the complete raw material of unreacted, finally reactant is cooled, obtain imidazolines.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and alcohol solvent, mechanical stirring, at 60 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:0.8, reactant (imidazolines, methylcarbonate) is 1:0.5 with the mass ratio of alcohol solvent, stirring reaction 4h; Be warming up to 95 ~ 105 DEG C, reaction 10h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 7
step one: the preparation of imidazolines
amidate action, under nitrogen protection, to adding the stearic acid and polyether polyamine NH that mol ratio is 1:0.8 in the four-hole bottle reactor of thermometer, agitator, prolong and water trap
2
c
2
h
4
nH (C
2
h
4
o)
6
h also stirs, and is warming up to 110 DEG C and reduces pressure to make vacuum tightness be 0.1MPa in 1h, continues reaction 2h, isolates the water that amidate action generates;
cyclization, in 7h by the temperature of above-mentioned reactor from 110 DEG C slowly rise to 160 DEG C, vacuum tightness is slowly increased to 0.4MPa, steam the water that cyclization generates, then insulation at 160 DEG C, control vacuum tightness is 0.7MPa, continues reaction 2h, steams moisture unnecessary in reaction system and the complete raw material of unreacted, finally reactant is cooled, obtain imidazolines.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and ethylene glycol solvent, mechanical stirring, at 70 DEG C, methylcarbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and methylcarbonate is 1:0.8, reactant (imidazolines, methylcarbonate) is 1:0.75 with the mass ratio of ethylene glycol solvent, stirring reaction 3h; Be warming up to 105 ~ 115 DEG C, reaction 8h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 8
step one: the preparation of imidazolines
amidate action, under nitrogen protection, to adding the lauric acid and polyether polyamine NH that mol ratio is 1:1 in the four-hole bottle reactor of thermometer, agitator, prolong and water trap
2
c
2
h
4
nH (C
2
h
4
o)
8
h also stirs, and is warming up to 100 DEG C and reduces pressure to make vacuum tightness be 0.2MPa in 0.5h, continues reaction 1.5h, isolates the water that amidate action generates;
cyclization, in 6h by the temperature of above-mentioned reactor from 100 DEG C slowly rise to 175 DEG C, vacuum tightness is slowly increased to 0.6MPa, steam the water that cyclization generates, then insulation at 175 DEG C, control vacuum tightness is 0.75MPa, continues reaction 1h, steams moisture unnecessary in reaction system and the complete raw material of unreacted, finally reactant is cooled, obtain imidazolines.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and n-butanol solvent, mechanical stirring, at 80 DEG C, diethyl carbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and diethyl carbonate is 1:0.8, reactant (imidazolines, diethyl carbonate) is 1:1.25 with the mass ratio of n-butanol solvent, stirring reaction 2h; Be warming up to 110 ~ 120 DEG C, reaction 5h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
embodiment 9
step one: the preparation of imidazolines
amidate action, under nitrogen protection, to adding the lauric acid and NH that mol ratio is 1:1.3 in the four-hole bottle reactor of thermometer, agitator, prolong and water trap
2
c
2
h
4
nH (C
2
h
4
o)
8
h also stirs, and is warming up to 100 DEG C and reduces pressure to make vacuum tightness be 0.2MPa in 0.5h, continues reaction 0.5h, isolates the water that amidate action generates;
cyclization, in 3h by the temperature of above-mentioned reactor from 100 DEG C slowly rise to 190 DEG C, vacuum tightness is slowly increased to 0.3MPa, steam the water that cyclization generates, then insulation at 190 DEG C, control vacuum tightness is 0.75MPa, continues reaction 3h, steams moisture unnecessary in reaction system and the complete raw material of unreacted, finally reactant is cooled, obtain imidazolines.
step 2: the synthesis of imidazoline quaternary ammonium salt
to with add successively in the four-hole bottle reactor of thermometer, agitator, prolong step one synthesize imidazolines and sec-butyl alcohol solvent, mechanical stirring, at 90 DEG C, ethylene carbonate is slowly added drop-wise in described reactor, wherein the mol ratio of imidazolines and ethylene carbonate is 1:0.8, reactant (imidazolines, ethylene carbonate) is 1:1.5 with the mass ratio of sec-butyl alcohol solvent, stirring reaction 1h; Be warming up to 100 ~ 110 DEG C, reaction 3h, cooling obtains the imidazoline quaternary ammonium salt of brown liquid shape.
the imidazoline quaternary ammonium salt that embodiment 1 to 4 obtains is soluble transparent liquid, can dissolve each other with water with arbitrary proportion.According to People's Republic of China (PRC) oil and gas industry standard SY/T5405-1996 " acidifying inhibiter method for testing performance and evaluation index ", with carbon steel piping pickle solution (hydrochloric acid mass concentration is about 15%) for corrosive medium, adopt the test piece of A3 carbon steel, imidazoline quaternary ammonium salt obtained for embodiment 1 ~ 4 is dissolved in respectively obtained sample 1 ~ 4 in quantitative deionized water, the inhibiter of the OED being by model dissolves in obtained described control sample in quantitative deionized water, by static steel experiment to sample 1 ~ 4 and control sample, check sample is tested, test result is in table 1.Described check sample is deionized water.
table 1 corrosion inhibition test result
as can be seen from table 1, the imidazoline quaternary ammonium salt adopting preparation method of the present invention to synthesize has good corrosion mitigating effect, and corrosion inhibition rate comparatively control sample is high by more than 5%, can be used as water treatment corrosion inhibitors.
above-described embodiment, only for technical conceive of the present invention and feature are described, its object is to person skilled in the art and can understand content of the present invention and implement according to this, can not limit protection scope of the present invention with this.The equivalent transformation that all spirit according to the present invention are done or modification, all should be encompassed within protection scope of the present invention.
Claims (10)
1. the preparation method of a water treatment corrosion inhibitors, described water treatment corrosion inhibitors is imidazoline quaternary ammonium salt, described method comprises the step making imidazolines and quaternizing agent generation salt-forming reaction generate described imidazoline quaternary ammonium salt, it is characterized in that, described tetrahydroglyoxaline quaternizing agent is methylcarbonate, diethyl carbonate, one or more combination in ethylene carbonate, described salt-forming reaction is implemented as follows: join in reactor by imidazolines and solvent, under the condition stirred, control temperature of reaction 60 ~ 90 DEG C, quaternizing agent is added drop-wise in reactor, reaction 1 ~ 4h, then be warming up to 95 ~ 120 DEG C, reaction 3 ~ 10h, cools and obtains described imidazoline quaternary ammonium salt.
2. preparation method according to claim 1, is characterized in that: the structural formula of described imidazolines is as follows:
In above formula, R is C
6~ C
18straight chain group, be selected from the one in pentadecyl, heptadecyl, 17 carbon-9-thiazolinyls, tridecyl, undecyl, nonyl, hexyl; N=4 ~ 8.
3. preparation method according to claim 1 and 2, is characterized in that: described solvent is alcoholic solvent.
4. preparation method according to claim 3, is characterized in that: described solvent is one or more the combination be selected from ethanol, ethylene glycol, n-propyl alcohol, Virahol, propyl carbinol, sec-butyl alcohol.
5. preparation method according to claim 1 and 2, is characterized in that: the molar ratio of described imidazolines and quaternizing agent is 1:(0.6 ~ 1.4).
6. preparation method according to claim 1 and 2, is characterized in that: the quality summation of described imidazolines and quaternizing agent and the mass ratio of solvent are 1:(0.5 ~ 1.5).
7. preparation method according to claim 1 and 2, is characterized in that, described method also comprises the step preparing described imidazolines, and this step comprises:
Mol ratio is 1:(0.6 ~ 1.3 by amidate action: under nitrogen protection) organic carboxyl acid and organic polyether polyamine mixing, control temperature 90 ~ 110 DEG C, pressure 0.1 ~ 0.2MPa, reaction 1 ~ 4h, isolate amidate action generate water;
Cyclization: the temperature 150 ~ 200 DEG C controlling the system after amidate action, pressure 0.2 ~ 0.6MPa, reaction 3 ~ 8h, then control temperature 200 ~ 250 DEG C, pressure 0.6 ~ 0.8MPa, reaction 1 ~ 3h, isolate water in reaction system and the complete raw material of unreacted, cooling obtains described imidazolines.
8. preparation method according to claim 7, is characterized in that: described organic carboxyl acid is one or more the combination in Palmiticacid, stearic acid, oleic acid, myristic acid, lauric acid, capric acid, caproic acid.
9. preparation method according to claim 7, is characterized in that: described organic polyether polyamine is selected from NH
2c
2h
4nH (C
2h
4o)
4h, NH
2c
2h
4nH (C
2h
4o)
6h, NH
2c
2h
4nH (C
2h
4o)
8one or more combination in H.
10. a water treatment corrosion inhibitors, is characterized in that: described water treatment corrosion inhibitors is the imidazoline quaternary ammonium salt be shown below,
Wherein, a=1 and b=2 or 3, or a=2 and b=5;
n=4~8。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110863204A (en) * | 2019-11-29 | 2020-03-06 | 陕西科技大学 | Water-soluble bis-imidazoline corrosion inhibitor and preparation method thereof |
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|---|---|---|---|---|
| CN1163301A (en) * | 1996-04-24 | 1997-10-29 | 胜利石油管理局勘察设计研究院 | Acidifying corrosion inhibitor for oil well and its preparation |
| CN1562960A (en) * | 2004-03-29 | 2005-01-12 | 中国日用化学工业研究院 | Quaternary ammonium salt in ester-amines and synthetic method |
| CN101654303A (en) * | 2008-08-18 | 2010-02-24 | 天津大港油田科远石油工程有限责任公司 | Corrosion inhibitor suitable for complex wastewater of oilfield and preparation method thereof |
-
2015
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1163301A (en) * | 1996-04-24 | 1997-10-29 | 胜利石油管理局勘察设计研究院 | Acidifying corrosion inhibitor for oil well and its preparation |
| CN1562960A (en) * | 2004-03-29 | 2005-01-12 | 中国日用化学工业研究院 | Quaternary ammonium salt in ester-amines and synthetic method |
| CN101654303A (en) * | 2008-08-18 | 2010-02-24 | 天津大港油田科远石油工程有限责任公司 | Corrosion inhibitor suitable for complex wastewater of oilfield and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110863204A (en) * | 2019-11-29 | 2020-03-06 | 陕西科技大学 | Water-soluble bis-imidazoline corrosion inhibitor and preparation method thereof |
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