CN106431909B - 无酸催化合成季戊四醇油酸酯的方法 - Google Patents
无酸催化合成季戊四醇油酸酯的方法 Download PDFInfo
- Publication number
- CN106431909B CN106431909B CN201610842533.3A CN201610842533A CN106431909B CN 106431909 B CN106431909 B CN 106431909B CN 201610842533 A CN201610842533 A CN 201610842533A CN 106431909 B CN106431909 B CN 106431909B
- Authority
- CN
- China
- Prior art keywords
- pentaerythrite
- pentaerythritol oleate
- vacuum
- oleic acid
- anacidity
- 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.)
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 title claims abstract description 58
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 55
- 229940049964 oleate Drugs 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 18
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 18
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000005642 Oleic acid Substances 0.000 claims abstract description 18
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000032050 esterification Effects 0.000 claims abstract description 7
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 9
- 230000008092 positive effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 7
- 235000021322 Vaccenic acid Nutrition 0.000 description 7
- -1 Pentaerythrite vaccenic acid ester Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000009628 steelmaking Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201610842533.3A CN106431909B (zh) | 2016-09-22 | 2016-09-22 | 无酸催化合成季戊四醇油酸酯的方法 |
Applications Claiming Priority (1)
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CN201610842533.3A CN106431909B (zh) | 2016-09-22 | 2016-09-22 | 无酸催化合成季戊四醇油酸酯的方法 |
Publications (2)
Publication Number | Publication Date |
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CN106431909A CN106431909A (zh) | 2017-02-22 |
CN106431909B true CN106431909B (zh) | 2019-02-12 |
Family
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Family Applications (1)
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CN201610842533.3A Active CN106431909B (zh) | 2016-09-22 | 2016-09-22 | 无酸催化合成季戊四醇油酸酯的方法 |
Country Status (1)
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CN (1) | CN106431909B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109293510A (zh) * | 2018-09-30 | 2019-02-01 | 浙江皇马科技股份有限公司 | 一种季戊四醇酯的制备方法 |
CN111621103B (zh) * | 2020-06-09 | 2022-04-15 | 石家庄市德塑助剂有限公司 | 一种以脂肪酸酯为主的固体增塑剂及其制作方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1449374A (zh) * | 2000-09-11 | 2003-10-15 | 日本油脂株式会社 | 酯的制造方法 |
CN103936695A (zh) * | 2014-01-29 | 2014-07-23 | 张典华 | 一种无毒环保增塑剂及其制备方法 |
-
2016
- 2016-09-22 CN CN201610842533.3A patent/CN106431909B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1449374A (zh) * | 2000-09-11 | 2003-10-15 | 日本油脂株式会社 | 酯的制造方法 |
CN103936695A (zh) * | 2014-01-29 | 2014-07-23 | 张典华 | 一种无毒环保增塑剂及其制备方法 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
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Denomination of invention: Synthesis of pentaerythritol oleate without acid catalysis Effective date of registration: 20211221 Granted publication date: 20190212 Pledgee: Liaocheng high tech Zone Luxi small loan Co.,Ltd. Pledgor: SHANDONG RUIJIE NEW MATERIAL CO.,LTD. Registration number: Y2021980015524 |
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Date of cancellation: 20220111 Granted publication date: 20190212 Pledgee: Liaocheng high tech Zone Luxi small loan Co.,Ltd. Pledgor: SHANDONG RUIJIE NEW MATERIAL CO.,LTD. Registration number: Y2021980015524 |
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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: Synthesis of pentaerythritol oleate without acid catalysis Effective date of registration: 20220113 Granted publication date: 20190212 Pledgee: China Everbright Bank Ji'nan branch Pledgor: SHANDONG RUIJIE NEW MATERIAL CO.,LTD. Registration number: Y2022980000427 |
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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: 20230104 Granted publication date: 20190212 Pledgee: China Everbright Bank Ji'nan branch Pledgor: SHANDONG RUIJIE NEW MATERIAL CO.,LTD. Registration number: Y2022980000427 |
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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: Synthesis of pentaerythritol oleate by acid-free catalysis Effective date of registration: 20230110 Granted publication date: 20190212 Pledgee: China Everbright Bank Ji'nan branch Pledgor: SHANDONG RUIJIE NEW MATERIAL CO.,LTD. Registration number: Y2023980030826 |