KR20020090124A - 폴리하이드록시 알콜의 모노에스테르 제조방법 - Google Patents
폴리하이드록시 알콜의 모노에스테르 제조방법 Download PDFInfo
- Publication number
- KR20020090124A KR20020090124A KR1020020026266A KR20020026266A KR20020090124A KR 20020090124 A KR20020090124 A KR 20020090124A KR 1020020026266 A KR1020020026266 A KR 1020020026266A KR 20020026266 A KR20020026266 A KR 20020026266A KR 20020090124 A KR20020090124 A KR 20020090124A
- Authority
- KR
- South Korea
- Prior art keywords
- polyhydroxyalcohol
- monoesters
- alcohol
- catalyst
- glycerol
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 108
- 239000000203 mixture Substances 0.000 claims abstract description 44
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 26
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- -1 glyceride ester Chemical class 0.000 claims abstract description 16
- 239000012429 reaction media Substances 0.000 claims abstract description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
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- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 3
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 3
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- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
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- 239000011593 sulfur Substances 0.000 description 10
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 5
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- 238000010348 incorporation Methods 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
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- UPWGQKDVAURUGE-KTKRTIGZSA-N 2-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(CO)CO UPWGQKDVAURUGE-KTKRTIGZSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0112557.4 | 2001-05-23 | ||
| GBGB0112557.4A GB0112557D0 (en) | 2001-05-23 | 2001-05-23 | A process for manufacturing monoesters of polyhydroxyalcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020090124A true KR20020090124A (ko) | 2002-11-30 |
Family
ID=9915155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020020026266A Ceased KR20020090124A (ko) | 2001-05-23 | 2002-05-13 | 폴리하이드록시 알콜의 모노에스테르 제조방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6664404B2 (enExample) |
| EP (1) | EP1260497A3 (enExample) |
| JP (1) | JP4143331B2 (enExample) |
| KR (1) | KR20020090124A (enExample) |
| CA (1) | CA2386054A1 (enExample) |
| GB (1) | GB0112557D0 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007038025A2 (en) * | 2005-09-23 | 2007-04-05 | Stepan Company | High purity polyol monoester compositions and methods for producing the same |
| US9260372B2 (en) | 2012-02-28 | 2016-02-16 | Petroliam Nasional Berhad | Method for the production of polyols and uses thereof |
| SG11201405265QA (en) | 2012-02-28 | 2014-09-26 | Petroliam Nasional Berhad | Method for the production of esters and uses thereof |
| CN104302614B (zh) * | 2012-02-28 | 2017-03-08 | 马来西亚国家石油公司 | 用于生物润滑剂和生物聚合物的生物多元醇及其制备方法 |
| WO2013129909A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| KR102212416B1 (ko) | 2012-02-28 | 2021-02-05 | 페트롤리암 내셔널 버하드 (페트로나스) | 폴리우레탄 적용을 위한 폴리올의 조성물 |
| ITMI20130156A1 (it) * | 2013-02-05 | 2014-08-06 | Consiglio Nazionale Ricerche | Procedimento "one-pot" per la produzione di miscele di biodiesel e eteri del glicerolo utili come biocarburanti |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
| EP3184616B1 (en) * | 2014-08-22 | 2021-06-09 | Kao Corporation | Method for producing monoglyceride-containing composition |
| US10993704B2 (en) | 2017-09-25 | 2021-05-04 | Verathon Inc. | System and method for calibration of mechanical three-dimensional ultrasound probe |
| CN111685362B (zh) * | 2019-03-12 | 2022-05-13 | 湖南中烟工业有限责任公司 | 一种含有5-羟基酸醇酯的烟草薄片及其制备方法和应用 |
| KR20220162154A (ko) * | 2020-03-30 | 2022-12-07 | 카아길, 인코포레이팃드 | 폴리올의 지방산 에스테르의 제조 방법 및 제조 시스템 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789119A (en) * | 1954-02-09 | 1957-04-16 | Boake Roberts & Co Ltd | Production of fatty acid monoglycerides |
| DE1099520B (de) * | 1957-01-04 | 1961-02-16 | E F Drew & Co Inc | Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen |
| DE1133713B (de) * | 1960-07-13 | 1962-07-26 | Leybold Hochvakuum Anlagen | Verfahren zur Herstellung waermestabiler monoglyceridhaltiger Glyceridgemische |
| DK152358C (da) * | 1979-11-01 | 1988-07-25 | Nexus Aps | Fremgangsmaade til fremstilling af et produkt indeholdende emulgatorvirkning-udvisende partielle estere af glycerolkondensater med c4-26-fedtsyrer |
-
2001
- 2001-05-23 GB GBGB0112557.4A patent/GB0112557D0/en not_active Ceased
-
2002
- 2002-05-13 KR KR1020020026266A patent/KR20020090124A/ko not_active Ceased
- 2002-05-13 CA CA002386054A patent/CA2386054A1/en not_active Abandoned
- 2002-05-14 EP EP02076878A patent/EP1260497A3/en not_active Withdrawn
- 2002-05-14 US US10/145,049 patent/US6664404B2/en not_active Expired - Fee Related
- 2002-05-14 JP JP2002138604A patent/JP4143331B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1260497A3 (en) | 2003-10-22 |
| CA2386054A1 (en) | 2002-11-23 |
| JP2003012602A (ja) | 2003-01-15 |
| GB0112557D0 (en) | 2001-07-11 |
| JP4143331B2 (ja) | 2008-09-03 |
| US20030013907A1 (en) | 2003-01-16 |
| EP1260497A2 (en) | 2002-11-27 |
| US6664404B2 (en) | 2003-12-16 |
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