CN105085402A - 一种松香基咪唑啉季铵盐化合物及其制备方法 - Google Patents
一种松香基咪唑啉季铵盐化合物及其制备方法 Download PDFInfo
- Publication number
- CN105085402A CN105085402A CN201510578805.9A CN201510578805A CN105085402A CN 105085402 A CN105085402 A CN 105085402A CN 201510578805 A CN201510578805 A CN 201510578805A CN 105085402 A CN105085402 A CN 105085402A
- Authority
- CN
- China
- Prior art keywords
- rosin
- ammonium salt
- imidazoline
- salt compound
- quarternary ammonium
- 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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 179
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 179
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 179
- -1 imidazoline quaternary ammonium salt compound Chemical class 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims abstract description 123
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 57
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 28
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 17
- 230000018044 dehydration Effects 0.000 claims description 16
- 238000006297 dehydration reaction Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
- 239000008187 granular material Substances 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 229910052725 zinc Inorganic materials 0.000 claims description 14
- 239000011701 zinc Substances 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 claims description 7
- 229940057847 polyethylene glycol 600 Drugs 0.000 claims description 7
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 claims description 5
- 229940085675 polyethylene glycol 800 Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 abstract description 10
- 238000005260 corrosion Methods 0.000 abstract description 10
- 230000005764 inhibitory process Effects 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000003112 inhibitor Substances 0.000 abstract description 7
- 150000002500 ions Chemical class 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000001012 protector Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004176 ammonification Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229930004069 diterpene Natural products 0.000 description 3
- 150000004141 diterpene derivatives Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000000274 adsorptive effect Effects 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
-
- 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
- C23F11/16—Sulfur-containing compounds
- C23F11/163—Sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201510578805.9A CN105085402B (zh) | 2015-09-11 | 2015-09-11 | 一种松香基咪唑啉季铵盐化合物及其制备方法 |
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CN201510578805.9A CN105085402B (zh) | 2015-09-11 | 2015-09-11 | 一种松香基咪唑啉季铵盐化合物及其制备方法 |
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CN105085402A true CN105085402A (zh) | 2015-11-25 |
CN105085402B CN105085402B (zh) | 2017-11-21 |
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CN201510578805.9A Active CN105085402B (zh) | 2015-09-11 | 2015-09-11 | 一种松香基咪唑啉季铵盐化合物及其制备方法 |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105859627A (zh) * | 2016-04-27 | 2016-08-17 | 陕西科技大学 | 一种硫脲基松香咪唑啉季铵盐化合物及其制备方法 |
CN107385450A (zh) * | 2017-07-24 | 2017-11-24 | 陕西科技大学 | 一种聚乙二醇油酸基咪唑啉水溶性缓蚀剂及其制备方法 |
CN108192342A (zh) * | 2018-02-05 | 2018-06-22 | 罗宇强 | 一种免喷涂尼龙材料及其生产工艺 |
CN108727268A (zh) * | 2017-04-20 | 2018-11-02 | 中国石油天然气股份有限公司 | 一种松香咪唑啉季铵盐化合物、缓蚀剂及制备方法 |
CN109233777A (zh) * | 2018-08-30 | 2019-01-18 | 赵晴晴 | 一种油井用固体缓蚀剂 |
CN109355662A (zh) * | 2018-04-28 | 2019-02-19 | 天津市职业大学 | 镁合金缓蚀剂及其制备方法和应用 |
CN111087347A (zh) * | 2018-10-23 | 2020-05-01 | 中国石油化工股份有限公司 | 烃基咪唑啉磺酸盐两性离子表面活性剂、组合物及其制备方法和应用 |
CN111850568A (zh) * | 2020-06-30 | 2020-10-30 | 中国石油天然气集团有限公司 | 一种油田地面集输管线防垢下腐蚀用缓蚀剂及其制备方法 |
CN112694443A (zh) * | 2019-10-22 | 2021-04-23 | 中国石油化工股份有限公司 | 烃基咪唑啉聚醚磺酸盐表面活性剂及其制备方法 |
CN114507187A (zh) * | 2020-11-16 | 2022-05-17 | 中国石油天然气股份有限公司 | 改性咪唑啉季铵盐型沥青温拌剂及其制备方法 |
CN117343014A (zh) * | 2023-12-05 | 2024-01-05 | 东北大学 | 松香基硫脲咪唑季铵盐的制备方法及其应用 |
-
2015
- 2015-09-11 CN CN201510578805.9A patent/CN105085402B/zh active Active
Non-Patent Citations (2)
Title |
---|
王倩: "松香基咪唑啉季铵盐的合成及其缓蚀性能研究", 《中国优秀硕士学位论文全文数据库,工程科技Ⅰ辑》 * |
陶亮亮等: "咪唑啉季铵盐合成研究进展", 《皮革与化工》 * |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105859627A (zh) * | 2016-04-27 | 2016-08-17 | 陕西科技大学 | 一种硫脲基松香咪唑啉季铵盐化合物及其制备方法 |
CN108727268B (zh) * | 2017-04-20 | 2020-08-07 | 中国石油天然气股份有限公司 | 一种松香咪唑啉季铵盐化合物、缓蚀剂及制备方法 |
CN108727268A (zh) * | 2017-04-20 | 2018-11-02 | 中国石油天然气股份有限公司 | 一种松香咪唑啉季铵盐化合物、缓蚀剂及制备方法 |
CN107385450A (zh) * | 2017-07-24 | 2017-11-24 | 陕西科技大学 | 一种聚乙二醇油酸基咪唑啉水溶性缓蚀剂及其制备方法 |
CN108192342A (zh) * | 2018-02-05 | 2018-06-22 | 罗宇强 | 一种免喷涂尼龙材料及其生产工艺 |
CN109355662A (zh) * | 2018-04-28 | 2019-02-19 | 天津市职业大学 | 镁合金缓蚀剂及其制备方法和应用 |
CN109233777A (zh) * | 2018-08-30 | 2019-01-18 | 赵晴晴 | 一种油井用固体缓蚀剂 |
CN111087347A (zh) * | 2018-10-23 | 2020-05-01 | 中国石油化工股份有限公司 | 烃基咪唑啉磺酸盐两性离子表面活性剂、组合物及其制备方法和应用 |
CN111087347B (zh) * | 2018-10-23 | 2021-06-22 | 中国石油化工股份有限公司 | 烃基咪唑啉磺酸盐两性离子表面活性剂、组合物及其制备方法和应用 |
CN112694443A (zh) * | 2019-10-22 | 2021-04-23 | 中国石油化工股份有限公司 | 烃基咪唑啉聚醚磺酸盐表面活性剂及其制备方法 |
CN111850568A (zh) * | 2020-06-30 | 2020-10-30 | 中国石油天然气集团有限公司 | 一种油田地面集输管线防垢下腐蚀用缓蚀剂及其制备方法 |
CN114507187A (zh) * | 2020-11-16 | 2022-05-17 | 中国石油天然气股份有限公司 | 改性咪唑啉季铵盐型沥青温拌剂及其制备方法 |
CN114507187B (zh) * | 2020-11-16 | 2024-04-30 | 中国石油天然气股份有限公司 | 改性咪唑啉季铵盐型沥青温拌剂及其制备方法 |
CN117343014A (zh) * | 2023-12-05 | 2024-01-05 | 东北大学 | 松香基硫脲咪唑季铵盐的制备方法及其应用 |
CN117343014B (zh) * | 2023-12-05 | 2024-03-01 | 东北大学 | 松香基硫脲咪唑季铵盐的制备方法及其应用 |
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Effective date of registration: 20231215 Address after: 710000, 3rd Floor, Building E, Zhijing Future Port, Caotan 10th Road, Xi'an Economic and Technological Development Zone, Shaanxi Province Patentee after: Shaanxi Yuteng Chemical Holdings Development Co.,Ltd. Address before: 509 Kangrui Times Square, Keyuan Business Building, 39 Huarong Road, Gaofeng Community, Dalang Street, Longhua District, Shenzhen, Guangdong Province, 518000 Patentee before: Shenzhen lizhuan Technology Transfer Center Co.,Ltd. Effective date of registration: 20231215 Address after: 509 Kangrui Times Square, Keyuan Business Building, 39 Huarong Road, Gaofeng Community, Dalang Street, Longhua District, Shenzhen, Guangdong Province, 518000 Patentee after: Shenzhen lizhuan Technology Transfer Center Co.,Ltd. Address before: No. 1, Weiyang District university garden, Xi'an, Shaanxi Province, Shaanxi Patentee before: SHAANXI University OF SCIENCE & TECHNOLOGY |
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