CN104817193B - A kind of water treatment corrosion inhibitors and preparation method thereof - Google Patents
A kind of water treatment corrosion inhibitors and preparation method thereof Download PDFInfo
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Abstract
A kind of water treatment corrosion inhibitors of the present invention and preparation method thereof.Water treatment corrosion inhibitors is imidazoline quaternary ammonium salt, the step of this method includes making imidazolines that salt-forming reaction generation imidazoline quaternary ammonium salt occur with quaternizing agent, the synthesis of imidazolines is reacted by organic carboxyl acid and organic polyether polyamine to be made, quaternizing agent is one or more combinations in dimethyl carbonate, diethyl carbonate, ethylene carbonate, and salt-forming reaction is implemented as follows：Imidazolines and solvent are added in reactor, under conditions of stirring, 60 ~ 90 DEG C of controlling reaction temperature, quaternizing agent are added drop-wise in reactor, react 1 ~ 4h；95 ~ 120 DEG C are then heated to, 3 ~ 10h is reacted, cools down and produce the imidazoline quaternary ammonium salt.The inventive method meets the requirement of green chemical industry, building-up process low toxicity, easy to operate, product convenient post-treatment, and gained water treatment corrosion inhibitors has excellent corrosion inhibition.
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 widely used in water treatment corrosion inhibitors field, mainly due to its good water solubility
It is used as corrosion inhibitor for oil field, bactericide, restrainer, surfactant, cleaning agent etc..At present, both at home and abroad to imidazoline quaternary ammonium
The synthesis report of salt is a lot, when quaternized to imidazoline, more using conducts such as benzyl chloride, dimethyl suflfate, epoxychloropropane
Quaternizing agent, these reagent toxicities are strong, volatile, not easy to operate, producers endangered greatly, unfriendly to environment.Such as：In
A kind of preparation method of alkyl imidazoline quaternary ammonium salt disclosed in state's patent application 200910305443.0 and Chinese patent Shen
A kind of preparation method of metal inhibitor that please be disclosed in 201110060385.7, benzyl chloride or monoxone are used in the above method
As quaternizing agent, not only with toxicity, and the problem of easily produce the anticaustic that halide ion is brought.
The content of the invention
In view of the above-mentioned problems, an object of the present invention is on the premise of water treatment corrosion inhibitors sustained release performance is ensured, carry
Easy, the preparation method of the green water treatment corrosion inhibitors of production process for a kind of synthesis technique；The second object of the present invention
It is to provide a kind of new water treatment corrosion inhibitors, its corrosion inhibition is more preferable.
To reach above-mentioned purpose, a kind of technical scheme that the present invention uses is as follows：
A kind of preparation method of water treatment corrosion inhibitors, the water treatment corrosion inhibitors are imidazoline quaternary ammonium salt, methods described bag
Including makes imidazolines that the step of salt-forming reaction generates the imidazoline quaternary ammonium salt, described season occur with quaternizing agent
Ammonium reagent is one or more combinations in dimethyl carbonate, diethyl carbonate, ethylene carbonate, and the salt-forming reaction is real
Apply as follows：Imidazolines and solvent are added in reactor, under conditions of stirring, controlling reaction temperature 60 ~ 90
DEG C, quaternizing agent is added drop-wise in reactor, reacts 1 ~ 4h；95 ~ 120 DEG C are then heated to, 3 ~ 10h is reacted, cools down and produce
The imidazoline quaternary ammonium salt.
Preferably, the structural formula of the imidazolines is as follows：
In above formula, R be selected from pentadecyl, heptadecyl, 17 carbon -9- alkenyls, tridecyl, undecyl, nonyl,
One kind in hexyl；n=4~8.
Preferably, the solvent is alcohols solvent.Further, the solvent is preferably selected from ethanol, ethylene glycol, positive third
One or more combinations in alcohol, isopropanol, n-butanol, sec-butyl alcohol.
Further, the molar ratio of the imidazolines and quaternizing agent is 1：（0.6~1.4）.Imidazoles
The mass ratio of the quality summation and solvent of quinoline class compound and quaternizing agent is 1:0.5~1.5.
Further, the step of methods described also includes preparing imidazolines, the step includes：
Amidation process：Under nitrogen protection, it is 1 by mol ratio：（0.6~1.3）Organic carboxyl acid and organic polyether polyols
Amine mixes, and controls 90 ~ 110 DEG C, 0.1 ~ 0.2MPa of pressure of temperature, reacts 1 ~ 4h, isolates the water of amidation process generation；
Cyclization：Control 150 ~ 200 DEG C, 0.2 ~ 0.6MPa of pressure of the temperature of the system after amidation process, reaction 3
~ 8h, 200 ~ 250 DEG C, 0.6 ~ 0.8MPa of pressure of temperature is then controlled, react 1 ~ 3h, isolate water in reaction system and not
The raw material reacted, cooling obtain the imidazolines.
The preparation of imidazolines represents as follows with reaction equation：
Preferably, the organic carboxyl acid is in palmitic acid, stearic acid, oleic acid, myristic acid, laurate, capric acid, benzoic acid
One or more combinations.
Preferably, organic polyether polyamine is selected from NH2C2H4NH(C2H4O)4H、NH2C2H4NH(C2H4O)6H、
NH2C2H4NH(C2H4O)8One or more combinations in H.
The another technical scheme that the present invention takes is：A kind of water treatment corrosion inhibitors, it is the imidazoline season being shown below
Ammonium salt,
Wherein, a=1 and b=2 or 3, or a=2 and b=5；
n=4~8。
The present invention uses above technical scheme, has the following advantages that：The present invention is low using quaternizing agent toxicity, without pungent
Smell, meet the requirement of green chemical industry, building-up process low toxicity, easy to operate, product convenient post-treatment, and be free of halogen member
Element, product will not produce halogen ion corrosion phenomenon；And organic polyether polyamine in raw material causes imidazoline quaternary ammonium salt product
Water solubility it is more preferable.Water treatment corrosion inhibitors of the present invention can be obtained by simple, less toxic, easily-controllable technique productions, and at water
Reason corrosion inhibiter has excellent water solubility and corrosion inhibition, has broad application prospects.
Embodiment
Presently preferred embodiments of the present invention is described in detail below so that advantages and features of the invention can be easier to by
It will be understood by those skilled in the art that apparent clearly defined so as to be made to protection scope of the present invention.Adopted in embodiment
Implementation condition can do further adjustment according to specific requirement, and unreceipted implementation condition is usually the bar in normal experiment
Part.
Imidazoline quaternary ammonium salt in following embodiment 1 to 9 is synthesized by following route：
Wherein, R is selected from pentadecyl, heptadecyl, 17 carbon -9- alkenyls, tridecyl, undecyl, nonyl, benzene
Methyl；
A=1 and b=2 or b=3, or a=2, b=5；
n=4~8。
Embodiment 1
Step 1：The synthesis of imidazolines
Amidation process, it is under nitrogen protection, anti-to the four-hole bottle with thermometer, agitator, condenser pipe and water knockout drum
It is 1 to answer and mol ratio is added in device:1.1 palmitic acid and polyether polyamine NH2C2H4NH(C2H4O)4H is simultaneously stirred, and is risen in 0.5h
Temperature is to 100 DEG C and depressurizing makes vacuum be 0.1MPa, continues to react 0.5h, isolates the water of amidation process generation；
Cyclization, the temperature of above-mentioned reactor is slowly increased to from 100 DEG C to 200 DEG C in 5h, vacuum is slowly increased
To 0.6MPa, the water of cyclization generation is steamed, is then incubated at 200 DEG C, it is 0.75MPa control vacuum, continues reaction 1h,
Moisture unnecessary in reaction system and the complete raw material of unreacted are steamed, finally reactant is cooled down, obtains imidazolines.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and isopropanol solvent, mechanical agitation, at 80 DEG C, dimethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and dimethyl carbonate is 1:0.6, reactant（Imidazolines, carbonic acid diformazan
Ester）Mass ratio with isopropanol solvent is 1:1, stirring reaction 3h；100 DEG C ~ 110 DEG C are warming up to, reacts 6h, cooling obtains palm fibre
The imidazoline quaternary ammonium salt of red liquid shape.
Embodiment 2
Step 1：The synthesis of imidazolines
Synthetic method is the same as embodiment one.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and isopropanol solvent, mechanical agitation, at 80 DEG C, dimethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and dimethyl carbonate is 1:0.8, reactant（Imidazolines, carbonic acid diformazan
Ester）Mass ratio with isopropanol solvent is 1:1, stirring reaction 3h；100 DEG C ~ 110 DEG C are warming up to, reacts 6h, cooling obtains palm fibre
The imidazoline quaternary ammonium salt of red liquid shape.
Embodiment 3
Step 1：The synthesis of imidazolines
Synthetic method is the same as embodiment one.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and isopropanol solvent, mechanical agitation, at 80 DEG C, dimethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and dimethyl carbonate is 1:1, reactant（Imidazolines, dimethyl carbonate）
Mass ratio with isopropanol solvent is 1:1, stirring reaction 3h；100 DEG C ~ 110 DEG C are warming up to, reacts 6h, cooling obtains reddish brown
The liquid imidazoline quaternary ammonium salt of color.
Embodiment 4
Step 1：The synthesis of imidazolines
Synthetic method is the same as embodiment one.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and isopropanol solvent, mechanical agitation, at 80 DEG C, dimethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and dimethyl carbonate is 1:1.2, reactant（Imidazolines, carbonic acid diformazan
Ester）Mass ratio with isopropanol solvent is 1:1, stirring reaction 3h；100 DEG C ~ 110 DEG C are warming up to, reacts 6h, cooling obtains palm fibre
The imidazoline quaternary ammonium salt of red liquid shape.
Embodiment 5
Step 1：The synthesis of imidazolines
Synthetic method is the same as embodiment one.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and isopropanol solvent, mechanical agitation, at 80 DEG C, dimethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and dimethyl carbonate is 1:1.4, reactant（Imidazolines, carbonic acid diformazan
Ester）Mass ratio with isopropanol solvent is 1:1, stirring reaction 3h；100 DEG C ~ 110 DEG C are warming up to, reacts 6h, cooling obtains palm fibre
The imidazoline quaternary ammonium salt of red liquid shape.
Embodiment 6
Step 1：The preparation of imidazolines
Amidation process, it is under nitrogen protection, anti-to the four-hole bottle with thermometer, agitator, condenser pipe and water knockout drum
It is 1 to answer and mol ratio is added in device:0.6 oleic acid and polyether polyamine NH2C2H4NH(C2H4O)4H is simultaneously stirred, and is warming up in 1h
90 DEG C and depressurize make vacuum be 0.1MPa, continue react 3h, isolate amidation process generate water；
Cyclization, the temperature of above-mentioned reactor is slowly increased to from 90 DEG C to 150 DEG C in 8h, vacuum is slowly increased to
0.2MPa, the water of cyclization generation is steamed, be then incubated at 150 DEG C, it be 0.6MPa control vacuum, continues reaction 3h, steaming
Go out moisture unnecessary in reaction system and the complete raw material of unreacted, finally reactant is cooled down, obtains imidazolines.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and alcohol solvent, mechanical agitation, at 60 DEG C, dimethyl carbonate is slowly dropped in the reactor, wherein
The mol ratio of imidazolines and dimethyl carbonate is 1:0.8, reactant（Imidazolines, dimethyl carbonate）
Mass ratio with alcohol solvent is 1:0.5, stirring reaction 4h；95 ~ 105 DEG C are warming up to, reacts 10h, cooling obtains brownish red
Liquid imidazoline quaternary ammonium salt.
Embodiment 7
Step 1：The preparation of imidazolines
Amidation process, it is under nitrogen protection, anti-to the four-hole bottle with thermometer, agitator, condenser pipe and water knockout drum
It is 1 to answer and mol ratio is added in device:0.8 stearic acid and polyether polyamine NH2C2H4NH(C2H4O)6H is simultaneously stirred, and is heated up in 1h
To 110 DEG C and depressurizing makes vacuum be 0.1MPa, continues to react 2h, isolates the water of amidation process generation；
Cyclization, the temperature of above-mentioned reactor is slowly increased to from 110 DEG C to 160 DEG C in 7h, vacuum is slowly increased
To 0.4MPa, the water of cyclization generation is steamed, is then incubated at 160 DEG C, it is 0.7MPa control vacuum, continues reaction 2h,
Moisture unnecessary in reaction system and the complete raw material of unreacted are steamed, finally reactant is cooled down, obtains imidazolines.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and ethylene glycol solvent, mechanical agitation, at 70 DEG C, dimethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and dimethyl carbonate is 1:0.8, reactant（Imidazolines, carbonic acid diformazan
Ester）Mass ratio with ethylene glycol solvent is 1:0.75, stirring reaction 3h；105 ~ 115 DEG C are warming up to, reacts 8h, cooling obtains
The imidazoline quaternary ammonium salt of brown liquid shape.
Embodiment 8
Step 1：The preparation of imidazolines
Amidation process, it is under nitrogen protection, anti-to the four-hole bottle with thermometer, agitator, condenser pipe and water knockout drum
It is 1 to answer and mol ratio is added in device:1 laurate and polyether polyamine NH2C2H4NH(C2H4O)8H is simultaneously stirred, and is heated up in 0.5h
To 100 DEG C and depressurizing makes vacuum be 0.2MPa, continues to react 1.5h, isolates the water of amidation process generation；
Cyclization, the temperature of above-mentioned reactor is slowly increased to from 100 DEG C to 175 DEG C in 6h, vacuum is slowly increased
To 0.6MPa, the water of cyclization generation is steamed, is then incubated at 175 DEG C, it is 0.75MPa control vacuum, continues reaction 1h,
Moisture unnecessary in reaction system and the complete raw material of unreacted are steamed, finally reactant is cooled down, obtains imidazolines.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and n-butanol solvent, mechanical agitation, at 80 DEG C, diethyl carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and diethyl carbonate is 1:0.8, reactant（Imidazolines, carbonic acid diethyl
Ester）Mass ratio with n-butanol solvent is 1:1.25, stirring reaction 2h；110 ~ 120 DEG C are warming up to, reacts 5h, cooling obtains palm fibre
The imidazoline quaternary ammonium salt of red liquid shape.
Embodiment 9
Step 1：The preparation of imidazolines
Amidation process, it is under nitrogen protection, anti-to the four-hole bottle with thermometer, agitator, condenser pipe and water knockout drum
It is 1 to answer and mol ratio is added in device:1.3 laurate and NH2C2H4NH(C2H4O)8H is simultaneously stirred, and 100 DEG C are warming up in 0.5h simultaneously
Decompression makes vacuum be 0.2MPa, continues to react 0.5h, isolates the water of amidation process generation；
Cyclization, the temperature of above-mentioned reactor is slowly increased to from 100 DEG C to 190 DEG C in 3h, vacuum is slowly increased
To 0.3MPa, the water of cyclization generation is steamed, is then incubated at 190 DEG C, it is 0.75MPa control vacuum, continues reaction 3h,
Moisture unnecessary in reaction system and the complete raw material of unreacted are steamed, finally reactant is cooled down, obtains imidazolines.
Step 2：The synthesis of imidazoline quaternary ammonium salt
To with thermometer, agitator, condenser pipe four-hole bottle reactor in sequentially add step 1 synthesis imidazoline
Class compound and sec-butyl alcohol solvent, mechanical agitation, at 90 DEG C, ethylene carbonate is slowly dropped in the reactor, its
The mol ratio of middle imidazolines and ethylene carbonate is 1:0.8, reactant（Imidazolines, carbonic acid Asia second
Ester）Mass ratio with sec-butyl alcohol solvent is 1:1.5, stirring reaction 1h；100 ~ 110 DEG C are warming up to, reacts 3h, cooling obtains palm fibre
The imidazoline quaternary ammonium salt of red liquid shape.
Imidazoline quaternary ammonium salt made from embodiment 1 to 4 is soluble transparent liquid, can be dissolved each other with water with arbitrary proportion.
According to People's Republic of China (PRC) oil and gas industry standard SY/T5405-1996《Acidifying with corrosion inhibiter method for testing performance and
Evaluation index》, with carbon steel piping pickle（Hydrochloric acid mass concentration is about 15%）, will using A3 carbon steel test pieces for corrosive medium
Imidazoline quaternary ammonium salt made from embodiment 1 ~ 4 dissolves in respectively is made sample 1 ~ 4 in quantitative deionized water, by the OED of model
Corrosion inhibiter dissolve in the control sample be made in quantitative deionized water, by static steel experiment to sample 1 ~ 4 and right
It is tested than sample, blank sample, test result is shown in Table 1.The blank sample is deionized water.
The corrosion inhibition test result of table 1
There is the imidazoline quaternary ammonium salt of preparation method synthesis it can be seen from table 1 using the present invention preferable inhibition to imitate
Fruit, corrosion inhibition rate is high compared with control sample by more than 5%, can be used as water treatment corrosion inhibitors.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to person skilled in the art
Present disclosure can be understood and implemented according to this, protection scope of the present invention can not be limited with this.It is all according to the present invention
The equivalent transformation or modification that Spirit Essence is made, should all be included within the scope of the present invention.
Claims (6)
1. a kind of preparation method of water treatment corrosion inhibitors, the water treatment corrosion inhibitors is imidazoline quaternary ammonium salt, and methods described includes
Make imidazolines that the step of salt-forming reaction generates the imidazoline quaternary ammonium salt occur with quaternizing agent, its feature exists
In described imidazoline quaternizing agent is one or more groups in dimethyl carbonate, diethyl carbonate, ethylene carbonate
Close, the salt-forming reaction is implemented as follows：Imidazolines and solvent are added in reactor, under conditions of stirring,
60 ~ 90 DEG C of controlling reaction temperature, quaternizing agent is added drop-wise in reactor, reacts 1 ~ 4h；95 ~ 120 DEG C are then heated to, instead
3 ~ 10h is answered, cools down and produces the imidazoline quaternary ammonium salt；
The structural formula of the imidazolines is as follows：
Imidazoline structure formula
In above formula, R C6~C18Straight chain group, selected from pentadecyl, heptadecyl, 17 carbon -9- alkenyls, tridecyl, ten
One kind in one alkyl, nonyl, hexyl；n=4~8；
The step of methods described also includes preparing the imidazolines, the step includes：
Amidation process：Under nitrogen protection, it is 1 by mol ratio：（0.6~1.3）Organic carboxyl acid and organic polyether polyamine mix
Close, control 90 ~ 110 DEG C, 0.1 ~ 0.2MPa of pressure of temperature, react 1 ~ 4h, isolate the water of amidation process generation；
Cyclization：150 ~ 200 DEG C, 0.2 ~ 0.6MPa of pressure of the temperature of system after control amidation process, reaction 3 ~
8h, 200 ~ 250 DEG C, 0.6 ~ 0.8MPa of pressure of temperature is then controlled, react 1 ~ 3h, isolate water in reaction system and not anti-
The raw material answered, cooling obtain the imidazolines；
The molar ratio of the imidazolines and quaternizing agent is 1：（0.6~1.4）, the imidazolines chemical combination
The mass ratio of the quality summation and solvent of thing and quaternizing agent is 1:（0.5~1.5）.
2. preparation method according to claim 1, it is characterised in that：The solvent is alcohols solvent.
3. preparation method according to claim 2, it is characterised in that：The solvent is selected from ethanol, ethylene glycol, positive third
One or more combinations in alcohol, isopropanol, n-butanol, sec-butyl alcohol.
4. preparation method according to claim 1, it is characterised in that：The organic carboxyl acid is palmitic acid, stearic acid, oil
One or more combinations in acid, myristic acid, laurate, capric acid, caproic acid.
5. preparation method according to claim 1, it is characterised in that：Organic polyether polyamine is selected from NH2C2H4NH
(C2H4O)4H、NH2C2H4NH(C2H4O)6H、NH2C2H4NH(C2H4O)8One or more combinations in H.
6. water treatment corrosion inhibitors made from a kind of preparation method of water treatment corrosion inhibitors as claimed in claim 1, its feature exist
In：The water treatment corrosion inhibitors is the imidazoline quaternary ammonium salt being shown below,
Miaow quaternary salt structural formula
Wherein, a=1 and b=3, or a=2 and b=5；
n=4~8。
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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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2015
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| 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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