CN112138604B - Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof - Google Patents
Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof Download PDFInfo
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- CN112138604B CN112138604B CN202011003307.9A CN202011003307A CN112138604B CN 112138604 B CN112138604 B CN 112138604B CN 202011003307 A CN202011003307 A CN 202011003307A CN 112138604 B CN112138604 B CN 112138604B
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000001914 filtration Methods 0.000 claims abstract description 23
- 239000012286 potassium permanganate Substances 0.000 claims abstract description 22
- 239000000047 product Substances 0.000 claims abstract description 21
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001035 drying Methods 0.000 claims abstract description 16
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims abstract description 16
- 150000003949 imides Chemical class 0.000 claims abstract description 15
- 229910010084 LiAlH4 Inorganic materials 0.000 claims abstract description 10
- 239000012467 final product Substances 0.000 claims abstract description 10
- 239000012280 lithium aluminium hydride Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 235000010265 sodium sulphite Nutrition 0.000 claims abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 238000003379 elimination reaction Methods 0.000 claims abstract description 7
- 239000012535 impurity Substances 0.000 claims abstract description 7
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 7
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 6
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 6
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- HAUDLKKUHAFHRO-UHFFFAOYSA-N 2-oxaspiro[3.3]hept-6-ene-1,3-dione Chemical compound O=C1OC(=O)C11C=CC1 HAUDLKKUHAFHRO-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 229910010082 LiAlH Inorganic materials 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000005067 remediation Methods 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000007865 diluting Methods 0.000 abstract description 2
- ZJFOZWUVVZAYGJ-UHFFFAOYSA-N C(=O)OC=O.C1CC=C1 Chemical compound C(=O)OC=O.C1CC=C1 ZJFOZWUVVZAYGJ-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 230000006872 improvement Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN202011003307.9A CN112138604B (en) | 2020-09-22 | 2020-09-22 | Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof |
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CN202011003307.9A CN112138604B (en) | 2020-09-22 | 2020-09-22 | Double-carboxyl surfactant with anion-cation reversal capability and preparation method thereof |
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CN112138604A CN112138604A (en) | 2020-12-29 |
CN112138604B true CN112138604B (en) | 2022-06-10 |
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Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3238235A (en) * | 1963-04-29 | 1966-03-01 | Pennsalt Chemicals Corp | Fluorinated amido carboxylic acids and salts thereof |
US3985722A (en) * | 1973-12-12 | 1976-10-12 | Ajinomoto Co., Inc. | Process for preparing N-higher aliphatic acyl derivatives of amino acids, peptides or proteins |
JP4210879B2 (en) * | 1999-01-29 | 2009-01-21 | 中京油脂株式会社 | Multi-chain bipolar group compound and method for producing the same |
JP4051269B2 (en) * | 2002-11-14 | 2008-02-20 | ジョンソンディバーシー株式会社 | Liquid disinfectant cleaning composition |
CN101037570A (en) * | 2007-03-23 | 2007-09-19 | 广西民族大学 | Preparation method of multi-carboxyl colophony oxidation product |
CN101683601B (en) * | 2008-09-28 | 2012-01-25 | 郑州轻工业学院 | Alkyl-iminodisuccinate chelating surfactant and method for synthesizing same |
CN102101837A (en) * | 2010-12-06 | 2011-06-22 | 张家港田由新材料科技有限公司 | Preparation method of cis-hexahydroisoindoline |
CN103242216A (en) * | 2013-05-07 | 2013-08-14 | 兰州梦唐精细化工有限公司 | Synthesis method of N-Boc-hexahydro-5-oxo-cyclopenta (C) pyrrole |
CN103772333A (en) * | 2014-02-19 | 2014-05-07 | 吉林众鑫化工集团有限公司 | Method for synthesizing cis-4-cyclohexene-1, 2-dimethylbenzene anhydride |
CN104311821B (en) * | 2014-10-15 | 2016-08-31 | 江南大学 | A kind of preparation with the polymer drug-carried nano-micelle of dual responsiveness |
CN106473948B (en) * | 2015-09-02 | 2021-08-27 | 花王株式会社 | Detergent composition |
CN111229121B (en) * | 2020-02-26 | 2021-05-04 | 江南大学 | pH-responsive amphiphilic-strong-polarity intelligently-switched emulsion and preparation method thereof |
CN112125830A (en) * | 2020-09-22 | 2020-12-25 | 陕西科技大学 | Polyamide compound and preparation method thereof |
CN112142640B (en) * | 2020-09-22 | 2022-07-22 | 陕西科技大学 | Bola type surfactant with anion-cation reversal capability and preparation method thereof |
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Effective date of registration: 20240102 Address after: 745112 Fucheng street, sanliupu Town, Qingcheng County, Qingyang City, Gansu Province Patentee after: Gansu Kerino New Materials Technology Co.,Ltd. Address before: 745112 Fucheng street, sanliupu Town, Qingcheng County, Qingyang City, Gansu Province Patentee before: Gansu Zhilun New Material Technology Co.,Ltd. |
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