CN102277577A - Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof - Google Patents
Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof Download PDFInfo
- Publication number
- CN102277577A CN102277577A CN 201110226689 CN201110226689A CN102277577A CN 102277577 A CN102277577 A CN 102277577A CN 201110226689 CN201110226689 CN 201110226689 CN 201110226689 A CN201110226689 A CN 201110226689A CN 102277577 A CN102277577 A CN 102277577A
- Authority
- CN
- China
- Prior art keywords
- fluorine
- acid
- positively charged
- charged ion
- containing positively
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 54
- 239000011737 fluorine Substances 0.000 title claims abstract description 54
- 239000003112 inhibitor Substances 0.000 title claims abstract description 53
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 title claims abstract description 51
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 230000007797 corrosion Effects 0.000 title claims abstract description 19
- 238000005260 corrosion Methods 0.000 title claims abstract description 19
- 125000002091 cationic group Chemical group 0.000 title abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 159
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 239000002904 solvent Substances 0.000 claims abstract description 56
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 28
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 81
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 78
- -1 perfluoroalkyl sulfonyl fluoride Chemical compound 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 52
- 239000000376 reactant Substances 0.000 claims description 42
- 150000002500 ions Chemical class 0.000 claims description 41
- 238000009413 insulation Methods 0.000 claims description 39
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 8
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 8
- HSDJWNJDPDJOEV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O HSDJWNJDPDJOEV-UHFFFAOYSA-N 0.000 claims description 6
- 229910000975 Carbon steel Inorganic materials 0.000 claims description 6
- 239000010962 carbon steel Substances 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005642 Oleic acid Substances 0.000 claims description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 5
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 5
- 229940073608 benzyl chloride Drugs 0.000 claims description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
- HMRWGKIZOBXNRB-UHFFFAOYSA-N octane-1-sulfonyl fluoride Chemical compound CCCCCCCCS(F)(=O)=O HMRWGKIZOBXNRB-UHFFFAOYSA-N 0.000 claims description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- DNLXFZIXKJOKRM-UHFFFAOYSA-N chloromethane;ethane Chemical compound CC.ClC DNLXFZIXKJOKRM-UHFFFAOYSA-N 0.000 claims description 4
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- FKLSONDBCYHMOQ-UHFFFAOYSA-N 9E-dodecenoic acid Natural products CCC=CCCCCCCCC(O)=O FKLSONDBCYHMOQ-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- XZJZNZATFHOMSJ-KTKRTIGZSA-N cis-3-dodecenoic acid Chemical compound CCCCCCCC\C=C/CC(O)=O XZJZNZATFHOMSJ-KTKRTIGZSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 239000010779 crude oil Substances 0.000 abstract description 3
- 239000003921 oil Substances 0.000 abstract description 3
- 238000001179 sorption measurement Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000002462 imidazolines Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 125000005527 methyl sulfate group Chemical group 0.000 description 4
- 230000000116 mitigating effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Lubricants (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention provides a fluorine-containing cationic imidazoline corrosion inhibitor and a preparation method thereof. The method comprises the following steps: adding an organic carboxylic acid and diethylenetriamine into a reactor in a molar ratio of 1:(0.1-2); adding a benzene solvent, heating, and performing a reaction at the temperature of 130-165 DEG C; heating, and performing a cyclization reaction at the temperature of 190-210 DEG C; cooling to 80-110 DEG C after the cyclization reaction; dripping perfluoroalkglsulfonyl fluoride after cooling, and performing a thermostatic reaction; and dripping a quaternizing reagent after the thermostatic reaction, and performing a thermostatic reaction to prepare the fluorine-containing cationic imidazoline corrosion inhibitor. The corrosion inhibitor is a rufous sticky liquid and can be miscible with water in any proportion, wherein the flash point is more than 60 DEG C, the condensation point is less than minus 10 DEG C, and the density is between 0.86g/ml and 0.99g/ml. The fluorine-containing cationic imidazoline corrosion inhibitor has the advantages of good metal surface adsorption, easily formed oleophobic metal surface, less possibility of dropping and the like, and can be used for reducing the friction of organic media, such as crude oil, finished product oil and the like, to a vessel surface.
Description
Technical field
The present invention relates to a kind of imidazoline inhibitor and preparation method thereof, be specifically related to a kind of fluorine-containing positively charged ion imidazoline inhibitor and preparation method thereof.
Background technology
In recent years, imidazolines is that development is a kind of faster in the organic inhibitor, its molecular structure contains the nitrogen five-membered ring, its effect characteristics are: when metal contacts with acidic solution, imidazolines can form unimolecular film in the metallic surface, change hydrionic redox potential, reach the purpose of inhibition.
At present, the domestic report aspect imidazoline inhibitor includes: Wang Jianhua, Shu Fuchang etc. are raw material with diethylenetriamine, triethylene tetramine, polyethylene polyamine, oleic acid, Benzyl Chloride, Mono Chloro Acetic Acid, dehydrated alcohol etc., synthesizing series imidazolidine derivatives inhibiter.Zhu tames and dociles, Zhou Xiuqin etc. is a raw material with naphthenic acid, diethylenetriamine, Benzyl Chloride, has synthesized the cycloalkyl imidazolidine derivatives.Though imidazolines has certain effect aspect preventing metal corrosion, but all there is certain shortcoming in aspects such as the inhibition efficiency of above all kinds of imidazolines, high thermal resistance, water-soluble, hydrophobic nature, particularly aspects such as corrosion inhibition rate there is bigger disadvantageous effect, causes applying of imidazolines inhibiter to be affected at high temperature corrosion medium, flow media.
Summary of the invention
The objective of the invention is to improve above the deficiencies in the prior art, provide a kind of and had corrosion inhibition rate preferably and organic stream moving medium and keep fluorine-containing positively charged ion imidazoline inhibitor of certain corrosion mitigating effect and preparation method thereof down.
For achieving the above object, the technical solution used in the present invention is:
The preparation method of fluorine-containing positively charged ion imidazoline inhibitor may further comprise the steps:
With organic carboxyl acid and diethylenetriamine according to 1: the mol ratio of 0.1-2 adds reactor and gets reactant, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 0.1-2, add and to heat behind the benzene kind solvent and in 130-165 ℃ of reaction 0.5-5h, heat up then and in 190-210 ℃ of cyclization 0.5-5h, the cyclization postcooling is to 80-110 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.1-2, insulation reaction 0.5-5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.1-2, insulation reaction 0.5-5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Obtain refining fluorine-containing positively charged ion imidazoline inhibitor behind the mixing solutions recrystallization of described fluorine-containing positively charged ion imidazoline inhibitor with acetone and toluene, perhaps through obtaining refining fluorine-containing positively charged ion imidazoline inhibitor behind underpressure distillation separation unreacted reactant and the solvent.
Described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid.
Described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is cocinic acid, lauroleic acid, capric acid, formic acid, acetate, propionic acid, vinylformic acid, lauric acid, oleic acid or stearic acid.
Described benzene kind solvent is toluene, m-xylene, p-Xylol, o-Xylol or xylol.
Described perfluoroalkyl sulfonyl fluoride is perfluoro butyl sulfonic acid fluoride, perfluoro hexyl sulfonic acid fluoride or full-fluorine octyl sulfuryl fluoride.
Described quaternizing agent is organic chloride or methyl-sulfate.
Described organic chloride is Benzyl Chloride, t butyl chloride, Mono Chloro Acetic Acid or chloracetate, and described t butyl chloride is 1, and 1-2 methyl chloride ethane, described chloracetate are sodium chloroacetate.
This inhibiter is a liquid russet, and is miscible with the water arbitrary proportion, and flash-point is greater than 60 ℃, and condensation point is less than-10 ℃, and density is 0.86-0.99g/ml.
This inhibiter corrosion inhibition rate to carbon steel in the aqueous hydrochloric acid of 25 ℃ of following massfractions 6% reaches more than 90%.
The prepared fluorine-containing positively charged ion imidazoline inhibitor of the present invention is introduced by the raw material of fluoro-containing group and is made the imidazoline inhibitor molecule can reduce the interfacial tension of profit corrosive medium and metallic surface greatly, the easier metallic surface that is adsorbed on after quaternized, form fluorine-containing inhibiter adsorption layer, thereby can effectively stop diffusion and reduction corrosive medium (oil or water) frictional coefficient and the resistance to flow of hydrogen ion to the metallic surface, therefore, can be used for Crude Oil Transportation, fields such as refinery, have with the metallic surface and adsorb, and easily form the metallic surface and hate oil, advantages such as difficult drop-off, simultaneously can reduce organic medium such as crude oil, the finished product wet goods has corrosion inhibition rate and the certain corrosion mitigating effect of the following maintenance of organic stream moving medium preferably to the characteristics such as frictional force of vessel surface.
Embodiment
The present invention will be further described below in conjunction with embodiment.
Embodiment 1
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 0.1 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is an oleic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 0.1, described benzene kind solvent is a dimethylbenzene, add and to heat behind the benzene kind solvent and in 130 ℃ of reaction 0.5h, heat up then and in 190 ℃ of cyclization 0.5h, cyclization postcooling to 80 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.1, described perfluoroalkyl sulfonyl fluoride is a perfluoro butyl sulfonic acid fluoride, insulation reaction 0.5h behind the dropping perfluoroalkyl sulfonyl fluoride drips quaternizing agent after the insulation reaction, described quaternizing agent is a methyl-sulfate, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.1, and insulation reaction 0.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 2
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 2 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a stearic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 2, described benzene kind solvent is a m-xylene, heat and 165 ℃ of reaction 5h after adding benzene kind solvent, heat up then and in 210 ℃ of cyclization 5h, cyclization postcooling to 110 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 2, described perfluoroalkyl sulfonyl fluoride is the perfluoro hexyl sulfonic acid fluoride, insulation reaction 5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 2, described quaternizing agent is an organic chloride, described organic chloride is a t butyl chloride, described t butyl chloride is 1,1-2 methyl chloride ethane, insulation reaction 5h gets fluorine-containing positively charged ion imidazoline inhibitor after dripping quaternizing agent, and described fluorine-containing positively charged ion imidazoline inhibitor obtains refining fluorine-containing positively charged ion imidazoline inhibitor after separating unreacted reactant and solvent through underpressure distillation.
Embodiment 3
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 0.4 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a cocinic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 0.4, described benzene kind solvent is a p-Xylol, add and to heat behind the benzene kind solvent and in 140 ℃ of reaction 1.5h, heat up then and in 195 ℃ of cyclization 1.5h, cyclization postcooling to 85 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.4, described perfluoroalkyl sulfonyl fluoride is a full-fluorine octyl sulfuryl fluoride, and insulation reaction 1.5h behind the dropping perfluoroalkyl sulfonyl fluoride drips quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.4, described quaternizing agent is an organic chloride, and described organic chloride is a Mono Chloro Acetic Acid, and insulation reaction 1.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 4
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 0.8 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is an oleic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 0.8, described benzene kind solvent is an o-Xylol, add and to heat behind the benzene kind solvent and in 150 ℃ of reaction 2.5h, heat up then and in 200 ℃ of cyclization 2.5h, cyclization postcooling to 90 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.8, described perfluoroalkyl sulfonyl fluoride is a perfluoro butyl sulfonic acid fluoride, insulation reaction 2.5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.8, and described quaternizing agent is an organic chloride, and described organic chloride is a chloracetate, described chloracetate is a sodium chloroacetate, and insulation reaction 2.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 5
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 1.2 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a lauroleic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 1.2, described benzene kind solvent is an xylol, add and to heat behind the benzene kind solvent and in 160 ℃ of reaction 3.5h, heat up then and in 205 ℃ of cyclization 3.5h, cyclization postcooling to 95 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 1.2, described perfluoroalkyl sulfonyl fluoride is the perfluoro hexyl sulfonic acid fluoride, insulation reaction 3.5h behind the dropping perfluoroalkyl sulfonyl fluoride drips quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 1.2, described quaternizing agent is a methyl-sulfate, and insulation reaction 3.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 6
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 1.6 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a capric acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 1.6, described benzene kind solvent is an xylol, add and to heat behind the benzene kind solvent and in 155 ℃ of reaction 4.5h, heat up then and in 208 ℃ of cyclization 4.5h, cyclization postcooling to 100 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 1.6, described perfluoroalkyl sulfonyl fluoride is a full-fluorine octyl sulfuryl fluoride, insulation reaction 4.5h behind the dropping perfluoroalkyl sulfonyl fluoride drips quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 1.6, described quaternizing agent is a methyl-sulfate, and insulation reaction 4.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 7
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 1.2 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a formic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 1.6, described benzene kind solvent is a toluene, add and to heat behind the benzene kind solvent and in 165 ℃ of reaction 0.5h, heat up then and in 205 ℃ of cyclization 1.5h, cyclization postcooling to 100 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.1, described perfluoroalkyl sulfonyl fluoride is a perfluoro butyl sulfonic acid fluoride, insulation reaction 1.5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.8, and described quaternizing agent is an organic chloride, and described organic chloride is a Benzyl Chloride, insulation reaction 0.5h gets fluorine-containing positively charged ion imidazoline inhibitor after dripping quaternizing agent, obtains refining fluorine-containing positively charged ion imidazoline inhibitor behind the mixing solutions recrystallization of described fluorine-containing positively charged ion imidazoline inhibitor with acetone and toluene.
Embodiment 8
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 0.4 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is an acetate, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 0.8, described benzene kind solvent is a m-xylene, add and to heat behind the benzene kind solvent and in 150 ℃ of reaction 3.5h, heat up then and in 195 ℃ of cyclization 5h, cyclization postcooling to 110 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.4, described perfluoroalkyl sulfonyl fluoride is the perfluoro hexyl sulfonic acid fluoride, insulation reaction 0.5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 1.2, and described quaternizing agent is an organic chloride, described organic chloride is a t butyl chloride, described t butyl chloride is 1,1-2 methyl chloride ethane, and insulation reaction 3.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 9
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 2 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a propionic acid, in reactant, add benzene kind solvent, described benzene kind solvent is a p-Xylol, the mass ratio of reactant and benzene kind solvent is 1: 0.1, add and to heat behind the benzene kind solvent and in 140 ℃ of reaction 1.5h, heat up then and in 210 ℃ of cyclization 3.5h, cyclization postcooling to 90 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 1.2, described perfluoroalkyl sulfonyl fluoride is a full-fluorine octyl sulfuryl fluoride, and insulation reaction 3.5h behind the dropping perfluoroalkyl sulfonyl fluoride drips quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 1.6, described quaternizing agent is an organic chloride, and described organic chloride is a Mono Chloro Acetic Acid, and insulation reaction 1.5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 10
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 1.6 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a vinylformic acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 1.2, described benzene kind solvent is an o-Xylol, add and to heat behind the benzene kind solvent and in 130 ℃ of reaction 4.5h, heat up then and in 200 ℃ of cyclization 0.5h, cyclization postcooling to 85 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.8, described perfluoroalkyl sulfonyl fluoride is a perfluoro butyl sulfonic acid fluoride, insulation reaction 2.5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.1, and described quaternizing agent is an organic chloride, and described organic chloride is a chloracetate, described chloracetate is a sodium chloroacetate, and insulation reaction 5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
Embodiment 11
Organic carboxyl acid and diethylenetriamine are added reactor according to 1: 1.5 mol ratio get reactant, described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid, described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is a lauric acid, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 1.5, described benzene kind solvent is an xylol, add and to heat behind the benzene kind solvent and in 155 ℃ of reaction 3h, heat up then and in 195 ℃ of cyclization 3h, cyclization postcooling to 95 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 1.5, described perfluoroalkyl sulfonyl fluoride is the perfluoro hexyl sulfonic acid fluoride, insulation reaction 3h behind the dropping perfluoroalkyl sulfonyl fluoride drips quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 1.5, described quaternizing agent is a methyl-sulfate, and insulation reaction 3h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
The fluorine-containing positively charged ion imidazoline inhibitor of method for preparing, this inhibiter outward appearance is a viscous liquid russet, and is miscible with the water arbitrary proportion, and flash-point is greater than 60 ℃, and condensation point is less than-10 ℃, and density (20 ℃) is 0.86-0.99g/ml.Corrosion inhibition rate to carbon steel in the aqueous hydrochloric acid of this inhibiter massfraction 6% under 25 ℃ (room temperatures) reaches more than 90%.
The effect contrast test:
With weight-loss method research, material is the Q235 carbon steel, the test before with test piece after abrasive paper for metallograph sanding and polishing, deionized water wash, dehydrated alcohol, acetone degreasing, drying for standby under the room temperature.During experiment it is hung respectively and immerse 25 ℃ and 60 ℃, add (the inhibiter add-on is 200mg/L) or do not add in the HCl aqueous solution of massfraction 6% of inhibiter, take out behind the 24h, clean the surface corrosion product with soft rubber, to constant weight, corrosion inhibition rate is measured and calculated to method routinely with deionized water and acetone cleaning-drying.
Under the normal temperature clean Q235 carbon steel sample is immersed in the aqueous hydrochloric acid of the massfraction 6% that contains the 1g/L inhibiter, takes out after 24 hours, embathe respectively once with deionized water and acetone, 60 ℃ of dryings of baking oven are surveyed its wetting angle.
It is as shown in table 1 to test every index comparing result: as can be seen from Table 1, the fluorine-containing imidazoline inhibitor of present patent application preparation at room temperature (25 ℃) reaches more than 90% the slowly-releasing rate of sample (carbon steel), corrosion mitigating effect is better than existing not fluorine-containing imidazoline inhibitor, simultaneously, the fluorine-containing imidazoline inhibitor of present patent application preparation has significantly reduced the friction of corrosive medium and metallic surface, keeps certain corrosion mitigating effect under the organic stream moving medium.
Table 1
The above only is one embodiment of the present invention, it or not whole or unique embodiment, the conversion of any equivalence that those of ordinary skills take technical solution of the present invention by reading specification sheets of the present invention is claim of the present invention and contains.
Claims (10)
1. the preparation method of a fluorine-containing positively charged ion imidazoline inhibitor is characterized in that may further comprise the steps:
With organic carboxyl acid and diethylenetriamine according to 1: the mol ratio of 0.1-2 adds reactor and gets reactant, in reactant, add benzene kind solvent, the mass ratio of reactant and benzene kind solvent is 1: 0.1-2, add and to heat behind the benzene kind solvent and in 130-165 ℃ of reaction 0.5-5h, heat up then and in 190-210 ℃ of cyclization 0.5-5h, the cyclization postcooling is to 80-110 ℃, the cooling back drips perfluoroalkyl sulfonyl fluoride, the mol ratio of perfluoroalkyl sulfonyl fluoride and organic carboxyl acid is 1: 0.1-2, insulation reaction 0.5-5h behind the dropping perfluoroalkyl sulfonyl fluoride, drip quaternizing agent after the insulation reaction, the mol ratio of quaternizing agent and organic carboxyl acid is 1: 0.1-2, insulation reaction 0.5-5h gets fluorine-containing positively charged ion imidazoline inhibitor behind the dropping quaternizing agent.
2. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1, it is characterized in that: obtain refining fluorine-containing positively charged ion imidazoline inhibitor behind the mixing solutions recrystallization of described fluorine-containing positively charged ion imidazoline inhibitor with acetone and toluene, perhaps through obtaining refining fluorine-containing positively charged ion imidazoline inhibitor behind underpressure distillation separation unreacted reactant and the solvent.
3. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1, it is characterized in that: described organic carboxyl acid is saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid.
4. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 3, it is characterized in that: described saturated or unsaturated C
1-C
22Monobasic fat organic carboxyl acid is cocinic acid, lauroleic acid, capric acid, formic acid, acetate, propionic acid, vinylformic acid, lauric acid, oleic acid or stearic acid.
5. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1, it is characterized in that: described benzene kind solvent is toluene, m-xylene, p-Xylol, o-Xylol or xylol.
6. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1, it is characterized in that: described perfluoroalkyl sulfonyl fluoride is perfluoro butyl sulfonic acid fluoride, perfluoro hexyl sulfonic acid fluoride or full-fluorine octyl sulfuryl fluoride.
7. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1, it is characterized in that: described quaternizing agent is organic chloride or methyl-sulfate.
8. according to the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 7, it is characterized in that: described organic chloride is Benzyl Chloride, t butyl chloride, Mono Chloro Acetic Acid or chloracetate, described t butyl chloride is 1,1-2 methyl chloride ethane, described chloracetate are sodium chloroacetate.
9. according to the fluorine-containing positively charged ion imidazoline inhibitor of the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1 preparation, it is characterized in that: this inhibiter is a liquid russet, miscible with the water arbitrary proportion, flash-point is greater than 60 ℃, condensation point is less than-10 ℃, and density is 0.86-0.99g/ml.
10. according to the fluorine-containing positively charged ion imidazoline inhibitor of the preparation method of the described a kind of fluorine-containing positively charged ion imidazoline inhibitor of claim 1 preparation, it is characterized in that: this inhibiter corrosion inhibition rate to carbon steel in the aqueous hydrochloric acid of 25 ℃ of following massfractions 6% reaches more than 90%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110226689 CN102277577B (en) | 2011-08-09 | 2011-08-09 | Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110226689 CN102277577B (en) | 2011-08-09 | 2011-08-09 | Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102277577A true CN102277577A (en) | 2011-12-14 |
| CN102277577B CN102277577B (en) | 2013-07-24 |
Family
ID=45103301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201110226689 Expired - Fee Related CN102277577B (en) | 2011-08-09 | 2011-08-09 | Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102277577B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102676275A (en) * | 2012-05-07 | 2012-09-19 | 中国石油化工股份有限公司 | Lubricating oil additive as well as preparation method and application thereof |
| CN105968052A (en) * | 2016-05-04 | 2016-09-28 | 辽宁科技学院 | Imidazoline corrosion inhibitor and preparation method thereof |
| CN108728207A (en) * | 2018-06-20 | 2018-11-02 | 中国石油化工股份有限公司 | Rust-inhibiting additive and preparation method thereof and the application in perfluoro polyether oil |
| CN110042398A (en) * | 2019-05-29 | 2019-07-23 | 中国石油化工股份有限公司 | Imidazoline high temperature resistant corrosion inhibitor and preparation method thereof |
| CN112341364A (en) * | 2020-09-29 | 2021-02-09 | 陈力群 | Preparation method and application of surfactant |
| CN114456148A (en) * | 2022-01-11 | 2022-05-10 | 中海油天津化工研究设计院有限公司 | Oil field corrosion inhibitor with good compatibility and preparation method thereof |
| CN116589999A (en) * | 2023-05-17 | 2023-08-15 | 广汉市华星新技术开发研究所（普通合伙） | Composite retarded acid and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020107151A1 (en) * | 1999-08-12 | 2002-08-08 | Ahn Young Soo | Mercaptoalcohol corrosion inhibitors |
| CN1769529A (en) * | 2004-11-05 | 2006-05-10 | 姚凯 | Oil well acidification inhibitor and its preparation method |
| CN101921233A (en) * | 2010-08-10 | 2010-12-22 | 陕西科技大学 | Tree imidazoline quaternary ammonium salt corrosion inhibitor and preparation method thereof |
| CN102070530A (en) * | 2011-01-07 | 2011-05-25 | 陕西省石油化工研究设计院 | N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and preparation method thereof |
-
2011
- 2011-08-09 CN CN 201110226689 patent/CN102277577B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020107151A1 (en) * | 1999-08-12 | 2002-08-08 | Ahn Young Soo | Mercaptoalcohol corrosion inhibitors |
| CN1769529A (en) * | 2004-11-05 | 2006-05-10 | 姚凯 | Oil well acidification inhibitor and its preparation method |
| CN101921233A (en) * | 2010-08-10 | 2010-12-22 | 陕西科技大学 | Tree imidazoline quaternary ammonium salt corrosion inhibitor and preparation method thereof |
| CN102070530A (en) * | 2011-01-07 | 2011-05-25 | 陕西省石油化工研究设计院 | N-alkylamino-2-perfluoroalkylimidazoline quaternary ammonium salt and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 《陕西大学学报》 20030430 张光华等 咪唑啉季铵盐表面活性剂的制备及其缓蚀性能的研究 第15-18页 1-10 第21卷, 第2期 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102676275A (en) * | 2012-05-07 | 2012-09-19 | 中国石油化工股份有限公司 | Lubricating oil additive as well as preparation method and application thereof |
| CN102676275B (en) * | 2012-05-07 | 2014-01-15 | 中国石油化工股份有限公司 | Lubricating oil additive as well as preparation method and application thereof |
| CN105968052A (en) * | 2016-05-04 | 2016-09-28 | 辽宁科技学院 | Imidazoline corrosion inhibitor and preparation method thereof |
| CN108728207A (en) * | 2018-06-20 | 2018-11-02 | 中国石油化工股份有限公司 | Rust-inhibiting additive and preparation method thereof and the application in perfluoro polyether oil |
| CN110042398A (en) * | 2019-05-29 | 2019-07-23 | 中国石油化工股份有限公司 | Imidazoline high temperature resistant corrosion inhibitor and preparation method thereof |
| CN112341364A (en) * | 2020-09-29 | 2021-02-09 | 陈力群 | Preparation method and application of surfactant |
| CN114456148A (en) * | 2022-01-11 | 2022-05-10 | 中海油天津化工研究设计院有限公司 | Oil field corrosion inhibitor with good compatibility and preparation method thereof |
| CN114456148B (en) * | 2022-01-11 | 2024-08-30 | 中海油天津化工研究设计院有限公司 | Oilfield corrosion inhibitor with good compatibility and preparation method thereof |
| CN116589999A (en) * | 2023-05-17 | 2023-08-15 | 广汉市华星新技术开发研究所（普通合伙） | Composite retarded acid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102277577B (en) | 2013-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102277577B (en) | Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof | |
| Deyab et al. | Effect of succinic acid on carbon steel corrosion in produced water of crude oil | |
| Obot et al. | Antifungal drugs as corrosion inhibitors for aluminium in 0.1 M HCl | |
| Touir et al. | Sodium gluconate as corrosion and scale inhibitor of ordinary steel in simulated cooling water | |
| CN102443124A (en) | Preparation method and application of multifunctional polyamine amide for oil field | |
| Mobin et al. | Synergistic influence of polyvinyl alcohol and surfactants on the corrosion inhibition of mild steel in 0.1 M H2SO4 | |
| CN104497216A (en) | Self-crosslinking acrylic emulsion and preparation method thereof | |
| WO2017049699A1 (en) | Water-based environmentally-friendly rust removal and resistance coating liquid and production process thereof | |
| CN105386066A (en) | Carbon steel pickling solution and use thereof | |
| KR20150121426A (en) | Coating Layer Structure For Prevention Of Corrosion And The Manufacturing Method Thereof | |
| CN108754510B (en) | Composite pickling corrosion inhibitor containing Schiff base and preparation method thereof | |
| CN109021648A (en) | A kind of preparation method of the dedicated super-hydrophobic antisepsis erosion chlorinated paraffin of coating | |
| CN117384535A (en) | Anti-sticking anti-corrosion thread coating and preparation method thereof | |
| CN116903539A (en) | CO-resistant 2 /H 2 S/H 2 Gemini type ionic liquid corrosion inhibitor for O corrosion, preparation method and application | |
| CN107829094B (en) | High temperature resistant corrosion inhibitor and preparation method thereof | |
| Yunying et al. | Influence of H2S concentration and pH value on corrosion behavior of weld joint of X65 subsea pipeline steel | |
| CN103613761B (en) | There is preparation method and the application thereof of viscosity reduction pour point depression and corrosion inhibition polyhydrazide | |
| CN104494232A (en) | Organic solid lubrication galvanized steel plate and manufacturing method thereof | |
| Chen et al. | Preparation of multi-functional superhydrophobic lanthanum surface on carbon steel via facile electrochemical method | |
| CN102220072B (en) | Special coating material for aluminium strip insulating coating | |
| CN103254785A (en) | Long-acting anti-rust oil and preparation method thereof | |
| CN104341815A (en) | Anti-corrosion coating | |
| CN107056708A (en) | A kind of utilization gutter oil prepares the method and its compounding metal inhibitor of Imidazoline Quatemary-ammonium-salt Corrosion Inhibitor | |
| Quej-Aké et al. | Electrochemical evaluation of chemical treatment effect on corrosion process of carbon steel in oil atmospheric distillation environments | |
| CN105860060A (en) | Three-dimensional crosslinking attapulgite/graphene/polyaniline composite anti-corrosion material and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| CB03 | Change of inventor or designer information |
Inventor after: Liu Yu Inventor after: Sun Yanwu Inventor after: Zhang Guanghua Inventor after: Liu Guojun Inventor after: Li Junguo Inventor after: Fang Yuhong Inventor after: Zhu Junfeng Inventor before: Zhang Guanghua Inventor before: Liu Guojun Inventor before: Li Junguo Inventor before: Fang Yuhong Inventor before: Zhu Junfeng |
|
| COR | Change of bibliographic data | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20160808 Address after: 710200 Shaanxi city of Xi'an province Jinghe Industrial Park North Jing Qin Lu Patentee after: SHAANXI RIXIN PETROCHEMICAL CO.,LTD. Address before: 710021 Shaanxi province Xi'an Weiyang University Park No. 1 Patentee before: SHAANXI University OF SCIENCE & TECHNOLOGY |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof Effective date of registration: 20180404 Granted publication date: 20130724 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: SHAANXI RIXIN PETROCHEMICAL CO.,LTD. Registration number: 2018990000264 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20181205 Granted publication date: 20130724 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: SHAANXI RIXIN PETROCHEMICAL CO.,LTD. Registration number: 2018990000264 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Fluorine-containing cationic imidazoline corrosion inhibitor and preparation method thereof Effective date of registration: 20181205 Granted publication date: 20130724 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: SHAANXI RIXIN PETROCHEMICAL CO.,LTD. Registration number: 2018990001148 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20210107 Granted publication date: 20130724 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: SHAANXI RIXIN PETROCHEMICAL Co.,Ltd. Registration number: 2018990001148 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A fluorinated cationic Imidazoline Corrosion Inhibitor and its preparation method Effective date of registration: 20210107 Granted publication date: 20130724 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: SHAANXI RIXIN PETROCHEMICAL Co.,Ltd. Registration number: Y2021990000013 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230209 Granted publication date: 20130724 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: SHAANXI RIXIN PETROCHEMICAL CO.,LTD. Registration number: Y2021990000013 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130724 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |