JPS59213799A - トリグリセライド油のエステル交換方法およびその装置 - Google Patents
トリグリセライド油のエステル交換方法およびその装置Info
- Publication number
- JPS59213799A JPS59213799A JP59068369A JP6836984A JPS59213799A JP S59213799 A JPS59213799 A JP S59213799A JP 59068369 A JP59068369 A JP 59068369A JP 6836984 A JP6836984 A JP 6836984A JP S59213799 A JPS59213799 A JP S59213799A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- mixture
- catalyst solution
- catalyst
- transesterification
- 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.)
- Granted
Links
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 230000032050 esterification Effects 0.000 title claims 2
- 238000005886 esterification reaction Methods 0.000 title claims 2
- 239000003054 catalyst Substances 0.000 claims abstract description 83
- 238000000034 method Methods 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 229910001868 water Inorganic materials 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000001694 spray drying Methods 0.000 claims abstract description 11
- 239000007921 spray Substances 0.000 claims abstract description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 28
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 9
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 235000021588 free fatty acids Nutrition 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 230000003068 static effect Effects 0.000 claims description 4
- 235000013310 margarine Nutrition 0.000 claims description 3
- 239000003264 margarine Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract description 18
- 230000008569 process Effects 0.000 abstract description 13
- 238000000265 homogenisation Methods 0.000 abstract description 10
- 238000010923 batch production Methods 0.000 abstract description 6
- 238000010924 continuous production Methods 0.000 abstract description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 2
- 238000009884 interesterification Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 91
- 235000019198 oils Nutrition 0.000 description 90
- 239000000243 solution Substances 0.000 description 35
- 238000007792 addition Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000002156 mixing Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000011049 filling Methods 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 235000019486 Sunflower oil Nutrition 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002600 sunflower oil Substances 0.000 description 6
- 238000011437 continuous method Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 150000004665 fatty acids Chemical group 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 240000005572 Syzygium cordatum Species 0.000 description 1
- 235000006650 Syzygium cordatum Nutrition 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005639 glycero group Chemical group 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
-
- 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
- C11C3/10—Ester interchange
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8309143 | 1983-04-05 | ||
| GB8309143 | 1983-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59213799A true JPS59213799A (ja) | 1984-12-03 |
| JPH0229717B2 JPH0229717B2 (https=) | 1990-07-02 |
Family
ID=10540639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59068369A Granted JPS59213799A (ja) | 1983-04-05 | 1984-04-05 | トリグリセライド油のエステル交換方法およびその装置 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4790962A (https=) |
| EP (1) | EP0121440B1 (https=) |
| JP (1) | JPS59213799A (https=) |
| AT (1) | ATE44760T1 (https=) |
| AU (1) | AU555590B2 (https=) |
| CA (1) | CA1224484A (https=) |
| DE (1) | DE3479036D1 (https=) |
| ZA (1) | ZA842521B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61141796A (ja) * | 1984-12-12 | 1986-06-28 | 植田製油株式会社 | 油脂類のエステル交換反応の方法および装置 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0320043B1 (en) * | 1987-12-11 | 1994-04-13 | Unilever N.V. | Process for the synthesis of polyol fatty acid esters |
| US4966876A (en) * | 1989-08-22 | 1990-10-30 | Viswanatha Sankaran | Transesterification of triglycerides |
| US5585506A (en) * | 1994-07-22 | 1996-12-17 | Lonza Inc. | One phase production of polyglycerol esters |
| WO1997033956A1 (en) * | 1996-03-14 | 1997-09-18 | Cargill B.V. | Homogeneous catalyst, process and apparatus for the interesterification of a triglyceride oil |
| ES2277727B1 (es) * | 2005-03-21 | 2008-06-16 | Biocombustibles Vascos S.A. | Transesterificacion de trigliceridos mediante nuevos sistemas cataliticos. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175261A (en) * | 1981-04-21 | 1982-10-28 | Mitsubishi Electric Corp | Detecting circuit for fluctuation of power supply |
| JPS5879098A (ja) * | 1981-10-06 | 1983-05-12 | ユニリ−バ−・ナ−ムロ−ゼ・ベンノ−トシヤ−プ | 油脂類のエステル交換法およびその装置 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2309949A (en) * | 1939-05-23 | 1943-02-02 | Best Foods Inc | Preparation of mixed esters of polyhydric alcohols |
| US2474740A (en) * | 1946-04-12 | 1949-06-28 | Colgate Palmolive Peet Co | Process of preparing partial esters of glycerine and fatty acids |
| GB779464A (en) * | 1954-04-28 | 1957-07-24 | Hedley Thomas & Co Ltd | Catalytic interesterification |
| US2738278A (en) * | 1954-04-28 | 1956-03-13 | Procter & Gamble | Catalytic interesterification |
| US2878274A (en) * | 1955-07-01 | 1959-03-17 | Swift & Co | Neutralizing and decolorizing lard interesterification reaction mixture |
| BE572839A (https=) * | 1958-02-12 | |||
| US3095431A (en) * | 1959-06-17 | 1963-06-25 | Lever Brothers Ltd | Interesterification process |
| US2999021A (en) * | 1960-04-27 | 1961-09-05 | Anderson Clayton & Company | Process for treatment of fats |
| US3170798A (en) | 1961-11-22 | 1965-02-23 | Procter & Gamble | Interesterification process |
| GB1403903A (en) * | 1972-04-13 | 1975-08-28 | Unilever Ltd | Process for the directed interesterification of glycerides |
| US4419291A (en) * | 1978-09-14 | 1983-12-06 | Safinco | Process for the directed interesterification of a triglyceride oil or oil mixture and triglyceride oils or oil mixture thus interesterified |
| BE870481A (nl) * | 1978-09-14 | 1979-01-02 | Vandemoortele Nv | Werkwijze voor het gericht heresteren van een triglyceride-olie of -oliemengsel en triglyceride-olie of -oliemengsel aldus heresterd |
| US4263216A (en) * | 1978-10-20 | 1981-04-21 | The Procter & Gamble Company | Diglyceride manufacture |
| US4335156A (en) * | 1980-09-19 | 1982-06-15 | Nabisco Brands, Inc. | Edible fat product |
| US4430276A (en) | 1981-10-02 | 1984-02-07 | Westinghouse Electric Corp. | Method of making stable UO2 fuel pellets |
-
1984
- 1984-03-30 CA CA000451010A patent/CA1224484A/en not_active Expired
- 1984-04-02 AU AU26331/84A patent/AU555590B2/en not_active Ceased
- 1984-04-03 AT AT84302266T patent/ATE44760T1/de not_active IP Right Cessation
- 1984-04-03 EP EP84302266A patent/EP0121440B1/en not_active Expired
- 1984-04-03 DE DE8484302266T patent/DE3479036D1/de not_active Expired
- 1984-04-04 ZA ZA842521A patent/ZA842521B/xx unknown
- 1984-04-05 JP JP59068369A patent/JPS59213799A/ja active Granted
-
1985
- 1985-12-23 US US06/814,154 patent/US4790962A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175261A (en) * | 1981-04-21 | 1982-10-28 | Mitsubishi Electric Corp | Detecting circuit for fluctuation of power supply |
| JPS5879098A (ja) * | 1981-10-06 | 1983-05-12 | ユニリ−バ−・ナ−ムロ−ゼ・ベンノ−トシヤ−プ | 油脂類のエステル交換法およびその装置 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61141796A (ja) * | 1984-12-12 | 1986-06-28 | 植田製油株式会社 | 油脂類のエステル交換反応の方法および装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE44760T1 (de) | 1989-08-15 |
| ZA842521B (en) | 1985-11-27 |
| DE3479036D1 (en) | 1989-08-24 |
| EP0121440A1 (en) | 1984-10-10 |
| US4790962A (en) | 1988-12-13 |
| JPH0229717B2 (https=) | 1990-07-02 |
| CA1224484A (en) | 1987-07-21 |
| AU2633184A (en) | 1984-10-11 |
| EP0121440B1 (en) | 1989-07-19 |
| AU555590B2 (en) | 1986-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |