CN101229998A - 三羟甲基丙烷脂肪酸酯的合成方法 - Google Patents
三羟甲基丙烷脂肪酸酯的合成方法 Download PDFInfo
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- CN101229998A CN101229998A CNA200710164788XA CN200710164788A CN101229998A CN 101229998 A CN101229998 A CN 101229998A CN A200710164788X A CNA200710164788X A CN A200710164788XA CN 200710164788 A CN200710164788 A CN 200710164788A CN 101229998 A CN101229998 A CN 101229998A
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- Prior art keywords
- fatty acid
- trimethylolpropane
- acid ester
- synthetic method
- solid catalyst
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 31
- 239000000194 fatty acid Substances 0.000 title claims abstract description 31
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 31
- -1 trimethylolpropane fatty acid ester Chemical class 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title description 9
- 230000002194 synthesizing effect Effects 0.000 title 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 13
- 238000010189 synthetic method Methods 0.000 claims abstract description 12
- 239000011949 solid catalyst Substances 0.000 claims abstract description 8
- 230000018044 dehydration Effects 0.000 claims abstract description 7
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 24
- 150000002632 lipids Chemical class 0.000 claims description 16
- 235000019865 palm kernel oil Nutrition 0.000 claims description 10
- 239000003346 palm kernel oil Substances 0.000 claims description 10
- 239000003240 coconut oil Substances 0.000 claims description 9
- 235000019864 coconut oil Nutrition 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical group [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 abstract 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 235000021360 Myristic acid Nutrition 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229960004232 linoleic acid Drugs 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012360 testing method Methods 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
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CNA200710164788XA CN101229998A (zh) | 2007-12-21 | 2007-12-21 | 三羟甲基丙烷脂肪酸酯的合成方法 |
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CNA200710164788XA CN101229998A (zh) | 2007-12-21 | 2007-12-21 | 三羟甲基丙烷脂肪酸酯的合成方法 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20121189A1 (it) * | 2012-07-06 | 2014-01-07 | Cnr Consiglio Naz Delle R Icerche | Processo per la sintesi di esteri di acidi grassi |
CN104672085A (zh) * | 2014-12-12 | 2015-06-03 | 诺泰生物科技(合肥)有限公司 | 三羟甲基丙烷有机酸酯的合成及在特种油中的应用 |
CN106975475A (zh) * | 2017-04-26 | 2017-07-25 | 中国石油化工股份有限公司 | 一种用于合成三羟甲基丙烷酯的催化剂及其制备方法以及应用 |
CN109652213A (zh) * | 2019-01-18 | 2019-04-19 | 重庆大学 | 一种酯类绝缘油及其制备方法 |
CN111018713A (zh) * | 2019-12-19 | 2020-04-17 | 联泓(江苏)新材料研究院有限公司 | 一种季戊四醇环氧改性蓖麻油封端的聚合物及其制备方法和应用 |
CN112778527A (zh) * | 2021-01-05 | 2021-05-11 | 吉林大学 | 一种多元醇脂肪酸酯/苯基/聚醚共改性硅油、制备方法及碳纤维专用低硅油剂 |
CN113088363A (zh) * | 2021-04-14 | 2021-07-09 | 海南热带海洋学院 | 一种椰子油脂肪酸复合酯的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3162616A (en) * | 1959-06-10 | 1964-12-22 | Nopco Chem Co | Esterification process |
US4113642A (en) * | 1976-11-11 | 1978-09-12 | Henkel Kommanditgesellschaft Auf Aktien | High viscosity neutral polyester lubricants |
EP0331280A1 (en) * | 1988-01-29 | 1989-09-06 | Pitman-Moore, Inc. | Method for esterifying hindered carboxylic acids |
WO1993024588A1 (en) * | 1992-06-03 | 1993-12-09 | Henkel Corporation | Polyol ester lubricants for high efficiency refrigerators |
CN1984980A (zh) * | 2004-05-27 | 2007-06-20 | 考格尼斯知识产权管理有限责任公司 | 适用于变压器的多元醇酯 |
-
2007
- 2007-12-21 CN CNA200710164788XA patent/CN101229998A/zh active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3162616A (en) * | 1959-06-10 | 1964-12-22 | Nopco Chem Co | Esterification process |
US4113642A (en) * | 1976-11-11 | 1978-09-12 | Henkel Kommanditgesellschaft Auf Aktien | High viscosity neutral polyester lubricants |
EP0331280A1 (en) * | 1988-01-29 | 1989-09-06 | Pitman-Moore, Inc. | Method for esterifying hindered carboxylic acids |
WO1993024588A1 (en) * | 1992-06-03 | 1993-12-09 | Henkel Corporation | Polyol ester lubricants for high efficiency refrigerators |
CN1984980A (zh) * | 2004-05-27 | 2007-06-20 | 考格尼斯知识产权管理有限责任公司 | 适用于变压器的多元醇酯 |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20121189A1 (it) * | 2012-07-06 | 2014-01-07 | Cnr Consiglio Naz Delle R Icerche | Processo per la sintesi di esteri di acidi grassi |
WO2014006595A1 (en) * | 2012-07-06 | 2014-01-09 | Cnr - Consiglio Nazionale Delle Ricerche | Process or the synthesis of esters of fatty acids |
CN104672085A (zh) * | 2014-12-12 | 2015-06-03 | 诺泰生物科技(合肥)有限公司 | 三羟甲基丙烷有机酸酯的合成及在特种油中的应用 |
CN104672085B (zh) * | 2014-12-12 | 2016-08-24 | 诺泰生物科技(合肥)有限公司 | 三羟甲基丙烷有机酸酯的合成及在特种油中的应用 |
CN106975475A (zh) * | 2017-04-26 | 2017-07-25 | 中国石油化工股份有限公司 | 一种用于合成三羟甲基丙烷酯的催化剂及其制备方法以及应用 |
CN106975475B (zh) * | 2017-04-26 | 2019-12-20 | 中国石油化工股份有限公司 | 一种用于合成三羟甲基丙烷酯的催化剂及其制备方法以及应用 |
CN109652213A (zh) * | 2019-01-18 | 2019-04-19 | 重庆大学 | 一种酯类绝缘油及其制备方法 |
CN111018713A (zh) * | 2019-12-19 | 2020-04-17 | 联泓(江苏)新材料研究院有限公司 | 一种季戊四醇环氧改性蓖麻油封端的聚合物及其制备方法和应用 |
CN112778527A (zh) * | 2021-01-05 | 2021-05-11 | 吉林大学 | 一种多元醇脂肪酸酯/苯基/聚醚共改性硅油、制备方法及碳纤维专用低硅油剂 |
CN112778527B (zh) * | 2021-01-05 | 2022-05-27 | 吉林大学 | 一种多元醇脂肪酸酯/苯基/聚醚共改性硅油、制备方法及碳纤维专用低硅油剂 |
CN113088363A (zh) * | 2021-04-14 | 2021-07-09 | 海南热带海洋学院 | 一种椰子油脂肪酸复合酯的制备方法 |
CN113088363B (zh) * | 2021-04-14 | 2022-10-21 | 海南热带海洋学院 | 一种椰子油脂肪酸复合酯的制备方法 |
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Owner name: HUANGMA CHEMICAL GROUP CO., ZHEJIANG Free format text: FORMER OWNER: WANG WEISONG Effective date: 20120614 |
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Effective date of registration: 20120614 Address after: 312363, Shangyu, Zhejiang Province town industrial zone, Zhejiang Real Madrid Chemical Group Co., Ltd. Applicant after: Huangma Chemical Group Co., Zhejiang Address before: 312363, Shangyu, Zhejiang Province town industrial zone, Zhejiang Real Madrid Chemical Group Co., Ltd. Applicant before: Wang Weisong |
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Application publication date: 20080730 |