CN108250426B - 脂肪仲醇聚氧乙烯醚的制备方法以及精制方法 - Google Patents
脂肪仲醇聚氧乙烯醚的制备方法以及精制方法 Download PDFInfo
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- CN108250426B CN108250426B CN201810184285.7A CN201810184285A CN108250426B CN 108250426 B CN108250426 B CN 108250426B CN 201810184285 A CN201810184285 A CN 201810184285A CN 108250426 B CN108250426 B CN 108250426B
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- Prior art keywords
- secondary alcohol
- polyoxyethylene ether
- alcohol polyoxyethylene
- preparation
- kettle
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- 150000003333 secondary alcohols Chemical class 0.000 title claims abstract description 162
- 229940051841 polyoxyethylene ether Drugs 0.000 title claims abstract description 118
- 229920000056 polyoxyethylene ether Polymers 0.000 title claims abstract description 118
- 238000002360 preparation method Methods 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000007670 refining Methods 0.000 title abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 69
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- -1 aliphatic secondary alcohol Chemical class 0.000 claims abstract description 46
- 230000002378 acidificating effect Effects 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 238000003756 stirring Methods 0.000 claims abstract description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 64
- 229910015900 BF3 Inorganic materials 0.000 claims description 50
- 239000003377 acid catalyst Substances 0.000 claims description 35
- 239000008139 complexing agent Substances 0.000 claims description 24
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 23
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 claims description 23
- 230000000536 complexating effect Effects 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000012670 alkaline solution Substances 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 84
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 42
- 230000000052 comparative effect Effects 0.000 description 25
- 239000000463 material Substances 0.000 description 22
- 239000012043 crude product Substances 0.000 description 21
- 238000011049 filling Methods 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- 239000007789 gas Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 239000012224 working solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- ADKFPZYATUZKCR-UHFFFAOYSA-N anisole;trifluoroborane Chemical group FB(F)F.COC1=CC=CC=C1 ADKFPZYATUZKCR-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- UWAXDPWQPGZNIO-UHFFFAOYSA-N benzylsilane Chemical compound [SiH3]CC1=CC=CC=C1 UWAXDPWQPGZNIO-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002761 deinking Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- JDVIRCVIXCMTPU-UHFFFAOYSA-N ethanamine;trifluoroborane Chemical group CCN.FB(F)F JDVIRCVIXCMTPU-UHFFFAOYSA-N 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Abstract
Description
实施例 | PEG含量 | 二恶烷 |
实施例1 | 0.31 | 2.69 |
实施例2 | 0.36 | 2.58 |
实施例3 | 0.28 | 3.1 |
实施例4 | 0.31 | 2.11 |
实施例5 | 0.43 | 2.45 |
实施例6 | 0.34 | 2.01 |
实施例7 | 0.36 | 1.85 |
实施例8 | 0.28 | 0.38 |
实施例9 | 0.05 | 0.22 |
实施例10 | 0 | 0 |
实施例11 | 0.12 | 0.52 |
对比例1 | 1.85 | 3.45 |
对比例2 | 1.82 | 3.86 |
对比例3 | 1.87 | 3.62 |
对比例4 | 0.89 | 3.56 |
对比例5 | 0.85 | 3.22 |
对比例6 | 3.2 | 4.51 |
对比例7 | 2.5 | 4.18 |
对比例8 | 1.15 | 3.56 |
对比例9 | 1.02 | 3.17 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201810184285.7A CN108250426B (zh) | 2018-03-07 | 2018-03-07 | 脂肪仲醇聚氧乙烯醚的制备方法以及精制方法 |
Applications Claiming Priority (1)
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CN201810184285.7A CN108250426B (zh) | 2018-03-07 | 2018-03-07 | 脂肪仲醇聚氧乙烯醚的制备方法以及精制方法 |
Publications (2)
Publication Number | Publication Date |
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CN108250426A CN108250426A (zh) | 2018-07-06 |
CN108250426B true CN108250426B (zh) | 2020-09-18 |
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CN201810184285.7A Active CN108250426B (zh) | 2018-03-07 | 2018-03-07 | 脂肪仲醇聚氧乙烯醚的制备方法以及精制方法 |
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CN (1) | CN108250426B (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109503825B (zh) * | 2018-11-19 | 2022-02-01 | 上海多纶化工有限公司 | 高环氧乙烷加成数仲醇聚氧乙烯醚的生产方法 |
CN109534969B (zh) * | 2018-11-19 | 2022-06-21 | 上海多纶化工有限公司 | 低环氧乙烷加成数仲醇聚氧乙烯醚的制备方法 |
CN111269093B (zh) * | 2018-12-05 | 2022-10-11 | 上海多纶化工有限公司 | 仲醇聚氧乙烯醚的制备方法 |
CN111393631B (zh) * | 2020-05-29 | 2022-09-09 | 上海多纶化工有限公司 | 仲醇聚氧乙烯醚的合成方法 |
CN111440306B (zh) * | 2020-05-29 | 2022-10-11 | 上海多纶化工有限公司 | 用于仲醇聚氧乙烯醚合成的催化剂及其应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
US3359331A (en) * | 1965-11-10 | 1967-12-19 | Exxon Research Engineering Co | Secondary alcohol ethoxylation |
US3372201A (en) * | 1966-06-17 | 1968-03-05 | Gen Aniline & Film Corp | Alkoxylation of secondary alcohols |
JPS50159595A (zh) * | 1974-06-17 | 1975-12-24 | ||
JP2003183383A (ja) * | 2001-12-14 | 2003-07-03 | Nippon Shokubai Co Ltd | 低臭気なアルコールの環状エーテル付加物の製造方法 |
CN106916056A (zh) * | 2017-04-13 | 2017-07-04 | 上海多纶化工有限公司 | 仲醇聚氧乙烯醚的精制方法 |
-
2018
- 2018-03-07 CN CN201810184285.7A patent/CN108250426B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
US3359331A (en) * | 1965-11-10 | 1967-12-19 | Exxon Research Engineering Co | Secondary alcohol ethoxylation |
US3372201A (en) * | 1966-06-17 | 1968-03-05 | Gen Aniline & Film Corp | Alkoxylation of secondary alcohols |
JPS50159595A (zh) * | 1974-06-17 | 1975-12-24 | ||
JP2003183383A (ja) * | 2001-12-14 | 2003-07-03 | Nippon Shokubai Co Ltd | 低臭気なアルコールの環状エーテル付加物の製造方法 |
CN106916056A (zh) * | 2017-04-13 | 2017-07-04 | 上海多纶化工有限公司 | 仲醇聚氧乙烯醚的精制方法 |
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Publication number | Publication date |
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CN108250426A (zh) | 2018-07-06 |
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PB01 | Publication | ||
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CB03 | Change of inventor or designer information | ||
CB03 | Change of inventor or designer information |
Inventor after: Li Dichuan Inventor after: Zhu Haiquan Inventor after: Li Shaomin Inventor before: Zhu Haiquan Inventor before: Li Shaomin Inventor before: Li Dichuan |
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TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20200630 Address after: Room 206, office building, Donggang sewage treatment plant, southwest of Gangqian Avenue and Zoushan Road, Xuwei New District, Lianyungang City, Jiangsu Province Applicant after: JISANGSU SECOL CHEMICAL Co. Address before: 201306 Nanjing West Road, Jingan District, Jingan District, Shanghai, 24 Applicant before: SHANGHAI WOOLEN CHEMICAL TECHNOLOGY Co.,Ltd. |
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Denomination of invention: Preparation method and refining method of fatty secondary alcohol polyoxyethylene ether Granted publication date: 20200918 Pledgee: Lianyungang branch of Bank of Jiangsu Co.,Ltd. Pledgor: JISANGSU SECOL CHEMICAL Co. Registration number: Y2024980013564 |