RU2754324C1 - Method for obtaining bis-imidazolines and their derivatives based on tetraethylenepentamines for corrosion protection of oilfield equipment and pipelines - Google Patents
Method for obtaining bis-imidazolines and their derivatives based on tetraethylenepentamines for corrosion protection of oilfield equipment and pipelines Download PDFInfo
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- RU2754324C1 RU2754324C1 RU2020141219A RU2020141219A RU2754324C1 RU 2754324 C1 RU2754324 C1 RU 2754324C1 RU 2020141219 A RU2020141219 A RU 2020141219A RU 2020141219 A RU2020141219 A RU 2020141219A RU 2754324 C1 RU2754324 C1 RU 2754324C1
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- imidazolines
- monocarboxylic acid
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- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical class NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000005260 corrosion Methods 0.000 title claims abstract description 13
- 230000007797 corrosion Effects 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940073608 benzyl chloride Drugs 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004698 Polyethylene Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 6
- 230000003993 interaction Effects 0.000 claims abstract description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 6
- 229920000768 polyamine Polymers 0.000 claims abstract description 6
- -1 polyethylene Polymers 0.000 claims abstract description 6
- 229920000573 polyethylene Polymers 0.000 claims abstract description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012535 impurity Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims abstract description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005642 Oleic acid Substances 0.000 claims abstract description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
- 238000004821 distillation Methods 0.000 claims abstract description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000007789 gas Substances 0.000 abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 102220491117 Putative postmeiotic segregation increased 2-like protein 1_C23F_mutation Human genes 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Изобретение относится к области защиты газо- и нефтепромыслового оборудования и трубопроводов, работающих в сероводородсодержащих высокоминерализованных водных средах, от коррозии и наводораживания, а также при транспортировке нефти и газа.The invention relates to the field of protection of gas and oil field equipment and pipelines operating in hydrogen sulfide-containing highly mineralized aqueous media from corrosion and hydrogen absorption, as well as during the transportation of oil and gas.
Известен ингибитор коррозии, применяемый вKnown corrosion inhibitor used in
сероводородсодержащих средах, который содержит продукт взаимодействия 1 моль жирной кислоты с числом углеродных атомов С10-С20 и (0,1-1) моль аминопарафина с числом углеродных атомов С8-С20 при следующим соотношением компонентов, мас. %:hydrogen sulfide-containing media, which contains the product of the interaction of 1 mol of fatty acid with the number of carbon atoms C 10 -C 20 and (0.1-1) mol of aminoparaffin with the number of carbon atoms C 8 -C 20 with the following ratio of components, wt. %:
продукт взаимодействия 1 моль жирной кислоты с числом углеродных атомов С10-С20 и (0,1-1) моль аминопарафина с числом углеродных атомов С8-С20 - 10-50;the product of the interaction of 1 mol of fatty acid with the number of carbon atoms C 10 -C 20 and (0.1-1) mol of aminoparaffin with the number of carbon atoms C 8 -C 20 - 10-50;
неионогенное поверхностно-активное вещество - 10-30;nonionic surfactant - 10-30;
растворитель - остальное (A.c. №2061091, C23F 11/00,1996).the solvent is the rest (A.c. # 2061091, C23F 11 / 00.1996).
Недостатком применения известного ингибитора коррозии является относительно невысокий защитный эффект (87-94%) при дозировке 50 мг/л. Другим недостатком является применение ядовитого вещества - метанола, последний имеет низкую температуру кипения и применяется в количестве 80 мг на 10 г активной основы и по описанию невозможно установить условия взаимодействия жирной кислоты и аминопарафина.The disadvantage of using the known corrosion inhibitor is a relatively low protective effect (87-94%) at a dosage of 50 mg / l. Another disadvantage is the use of a poisonous substance - methanol, the latter has a low boiling point and is used in an amount of 80 mg per 10 g of active base and it is impossible to establish the conditions for the interaction of fatty acid and aminoparaffin from the description.
Известен ингибитор сероводородной коррозии, состоящий из смеси хлоргидратов аминопарафинов (А.с. №652316, Е21В 43/00,1979). Недостатком известного ингибитора является невысокий эффект при дозировке до 100 мг/л.Known inhibitor of hydrogen sulfide corrosion, consisting of a mixture of hydrochloride aminoparaffins (AS No. 652316, E21B 43 / 00,1979). The disadvantage of the known inhibitor is its low effect at a dosage of up to 100 mg / l.
Задача изобретения - разработка способа получения ингибиторов коррозии, обеспечивающих эффективную защиту металлов газо- и нефтепромыслового оборудования, трубопроводов от коррозии.The objective of the invention is to develop a method for producing corrosion inhibitors that provide effective protection of metals of gas and oil field equipment, pipelines from corrosion.
Технический результат при использовании изобретения выражается в расширении сырьевой базы и ассортимента ингибиторов коррозии. Также результатом изобретения является удешевление конечного продукта.The technical result when using the invention is expressed in the expansion of the raw material base and the range of corrosion inhibitors. Also, the result of the invention is a reduction in the cost of the final product.
Поставленная задача решается заявляемым способом получения ингибиторов коррозии для защиты газо- и нефтепромыслового оборудования и трубопроводов на основе полиэтиленполиаминов и карбоновых кислот, с отгоном реакционной воды и примесей. В качестве полиэтиленполиаминов используют тетраэтиленпентамин (ТЭПА), который взаимодействует с монокарбоновыми кислотами, в качестве которых используют 2-этилгексановую (Эгексан.к.) или олеиновую (Ол.к.) кислоты, сначала при температуре 145-155°С в течение 4,5-5,5 ч, затем при 255°С в течение 2 ч в мольном соотношении ТЭПА: монокарбоновые кислоты равном 1:2 с последующим взаимодействием полученных бис-имидазолинов с бензилхлоридом при температуре 90°С.The problem is solved by the claimed method of producing corrosion inhibitors for the protection of gas and oil field equipment and pipelines based on polyethylene polyamines and carboxylic acids, with distillation of reaction water and impurities. Tetraethylenepentamine (TEPA) is used as polyethylene polyamines, which interacts with monocarboxylic acids, which are 2-ethylhexanoic (Ehexan.k.) Or oleic (OLC) acids, first at a temperature of 145-155 ° C for 4, 5-5.5 h, then at 255 ° C for 2 h in a molar ratio of TEPA: monocarboxylic acids equal to 1: 2, followed by the interaction of the obtained bis-imidazolines with benzyl chloride at a temperature of 90 ° C.
Вышеназванный результат получения ингибиторов коррозии, работающих в минерализованных и сероводородсодержащих средах, достигается особенностью, заключающейся в том, что ТЭПА взаимодействует с 2-этилгексановой (Эгексан.к.) или олеиновой (Ол.к.) кислотами сначала при температуре 145-155°С в течение 4,5-5,5 ч, затем при 255°С в течение 2 ч в мольном соотношении ТЭПА : кислоты=1:2 с образованием бис-имидазолинов (1):The above result of obtaining corrosion inhibitors operating in mineralized and hydrogen sulfide-containing environments is achieved by the feature that TEPA interacts with 2-ethylhexanoic (Ehexan.k.) Or oleic (Ol.k.) acids first at a temperature of 145-155 ° C for 4.5-5.5 h, then at 255 ° C for 2 h in a molar ratio of TEPA: acid = 1: 2 with the formation of bis-imidazolines (1):
R=С7Н15, С17Н33.R = C 7 H 15 , C 17 H 33 .
Полученные бис-имидазолины (1) взаимодействуют с бензилхлоридом (БХ) при температуре 90°С в мольном соотношении бис-имидазолин (1) : БХ=1:1 в течение 4-4,5 ч.The obtained bis-imidazolines (1) interact with benzyl chloride (BC) at a temperature of 90 ° C in a molar ratio of bis-imidazoline (1): BC = 1: 1 for 4-4.5 h.
Сущность изобретения поясняется следующими примерами.The essence of the invention is illustrated by the following examples.
Пример 1. В реактор с перемешивающим устройством, термометром, холодильником и капельной воронкой загружают 18,9 г (0,1 моль) тетраэтиленпентамина (ТЭПА) и 28,8 г (0,2 моль) 2-этилгексановой кислоты (Эгексан.к.) в мольном соотношении ТЭПА : Эгексан.к.=1:2. Реакционную смесь нагревают сначала при температуре 145°С в течение 4,5 ч, затем при температуре 255°С в течение 2 ч и непрерывно производят отгон реакционной воды и примесей, содержащихся в исходных продуктах.Example 1. In a reactor with a stirring device, a thermometer, a refrigerator and a dropping funnel, 18.9 g (0.1 mol) of tetraethylenepentamine (TEPA) and 28.8 g (0.2 mol) of 2-ethylhexanoic acid (Ehexan.k. ) in the molar ratio of TEPA: Ehexan.c. = 1: 2. The reaction mixture is heated first at a temperature of 145 ° C for 4.5 hours, then at a temperature of 255 ° C for 2 hours, and the reaction water and impurities contained in the starting products are continuously distilled off.
Получают 39,04 г (96,4%) бис-имидазолина (2).39.04 g (96.4%) of bis-imidazoline (2) are obtained.
Найдено, %: N 16,94. C24H47N5.Вычислено, %: N 17,28.Found,%: N 16.94. C 24 H 47 N 5. Calculated,%: N 17.28.
Полученное соединение (2) 40,5 (0,1 моль) взаимодействует с 12,65 г (0,1 моль) бензилхлорида (БХ) при температуре 90°С в течение 4 ч в мольном соотношении соединение (2) : БХ=1:1.The resulting compound (2) 40.5 (0.1 mol) interacts with 12.65 g (0.1 mol) of benzyl chloride (BC) at a temperature of 90 ° C for 4 h in a molar ratio of compound (2): BC = 1 :1.
Получают 51,30 г (95,9%) N-бензил-бис-(имидазолин)хлорида (3).51.30 g (95.9%) of N-benzyl bis (imidazoline) chloride (3) are obtained.
Найдено, %: N 12,74. C31H54N6Cl. Вычислено, %: N 13,17.Found,%: N 12.74. C 31 H 54 N 6 Cl. Calculated,%: N 13.17.
Пример 2. В условиях примера 1 в реактор загружают 18,9 г (0,1 моль) ТЭПА и 56,4 г (0,2 моль) олеиновой кислоты (Ол.к.) в мольном соотношении ТЭПА : Ол.к.=1:2. Реакционную смесь нагревают сначала при температуре 155°С в течение 5,5 ч, затем при температуре 255°С в течение 2 ч и непрерывно производят отгон реакционной воды и примесей, содержащихся в исходных продуктах.Example 2. Under the conditions of example 1, 18.9 g (0.1 mol) of TEPA and 56.4 g (0.2 mol) of oleic acid (Ol.k.) are loaded into the reactor in a molar ratio of TEPA: Ol.k. = 1: 2. The reaction mixture is heated first at a temperature of 155 ° C for 5.5 hours, then at a temperature of 255 ° C for 2 hours, and the reaction water and impurities contained in the starting products are continuously distilled off.
Получают 66,94 г (98,3%) бис-имидазолина (4).66.94 g (98.3%) of bis-imidazoline (4) are obtained.
Найдено, %: N 9,56. C46H83N5. Вычислено, %: N 9,92.Found,%: N 9.56. C 46 H 83 N 5 . Calculated,%: N 9.92.
Полученное соединение (4) 68,1 (0,1 моль) взаимодействует с 12,65 г (0,1 моль) БХ при температуре 90°С в течение 4,5 ч в мольном соотношении бис-имидазолин (4) : БХ=1:1.The resulting compound (4) 68.1 (0.1 mol) interacts with 12.65 g (0.1 mol) BC at a temperature of 90 ° C for 4.5 h in a molar ratio of bis-imidazoline (4): BC = 1: 1.
Получают 78,0 г (96,6%) N-бензил-бис(имидазолин)хлорида (5).78.0 g (96.6%) of N-benzyl bis (imidazoline) chloride (5) are obtained.
Найдено, %: N 9,06. C51H90N5Cl. Вычислено, %: N 9,49.Found,%: N 9.06. C 51 H 90 N 5 Cl. Calculated,%: N 9.49.
где R=Н (4), (НС1)СН2Н5С6 (5)where R = H (4), (HC1) CH 2 H 5 C 6 (5)
Примеры 1-2 подтверждают высокий выход бис-имидазолинов - 95,9-98,3%, а также высокий показатель защитного эффекта - 96,9-99,2% при условии выдерживания заявленных параметров процесса получения.Examples 1-2 confirm the high yield of bis-imidazolines - 95.9-98.3%, as well as a high protective effect - 96.9-99.2%, provided that the declared parameters of the production process are maintained.
При условии отклонения заявленных параметров процесса получения бис-имидазолинов и их производных, нагревание реакционной смеси тетраэтиленпентамина и этилгексановой кислоты при температуре 125°С в течение 1,5 ч демонстрирует снижение выхода продукта, а также понижение защитного эффекта.Subject to the deviation of the declared parameters of the process of obtaining bis-imidazolines and their derivatives, heating the reaction mixture of tetraethylenepentamine and ethylhexanoic acid at a temperature of 125 ° C for 1.5 h demonstrates a decrease in the yield of the product, as well as a decrease in the protective effect.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2350689C2 (en) * | 2007-03-09 | 2009-03-27 | Открытое акционерное общество "Каустик" (ОАО "Каустик") | Method for making acid corrosion inhibitors |
| RU2394941C1 (en) * | 2008-12-29 | 2010-07-20 | Общество с ограниченной ответственностью "Промышленно-торговая компания ТАНТАНА" | Procedure for production of corrosion inhibitors |
| RU2710700C1 (en) * | 2019-02-13 | 2020-01-09 | Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") | Corrosion inhibitor and method of its production |
| WO2020046967A1 (en) * | 2018-08-28 | 2020-03-05 | Kao Corporation | Oil and gas field corrosion inhibitor compositions |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2350689C2 (en) * | 2007-03-09 | 2009-03-27 | Открытое акционерное общество "Каустик" (ОАО "Каустик") | Method for making acid corrosion inhibitors |
| RU2394941C1 (en) * | 2008-12-29 | 2010-07-20 | Общество с ограниченной ответственностью "Промышленно-торговая компания ТАНТАНА" | Procedure for production of corrosion inhibitors |
| WO2020046967A1 (en) * | 2018-08-28 | 2020-03-05 | Kao Corporation | Oil and gas field corrosion inhibitor compositions |
| RU2710700C1 (en) * | 2019-02-13 | 2020-01-09 | Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") | Corrosion inhibitor and method of its production |
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