JPH01246293A - Method for purifying sugaralcohol ester of fatty acid - Google Patents
Method for purifying sugaralcohol ester of fatty acidInfo
- Publication number
- JPH01246293A JPH01246293A JP31118287A JP31118287A JPH01246293A JP H01246293 A JPH01246293 A JP H01246293A JP 31118287 A JP31118287 A JP 31118287A JP 31118287 A JP31118287 A JP 31118287A JP H01246293 A JPH01246293 A JP H01246293A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- soap
- reaction product
- ester
- solvent
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 24
- 239000000194 fatty acid Substances 0.000 title claims abstract description 24
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 24
- -1 sugaralcohol ester Chemical class 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 18
- 150000004665 fatty acids Chemical class 0.000 title abstract description 5
- 239000000344 soap Substances 0.000 claims abstract description 36
- 239000012528 membrane Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 5
- 230000007717 exclusion Effects 0.000 claims abstract description 4
- 238000000593 microemulsion method Methods 0.000 claims abstract description 4
- 239000000376 reactant Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 14
- 229930006000 Sucrose Natural products 0.000 description 14
- 239000005720 sucrose Substances 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- 239000004695 Polyether sulfone Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920006393 polyether sulfone Polymers 0.000 description 5
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000845 maltitol Substances 0.000 description 4
- 235000010449 maltitol Nutrition 0.000 description 4
- 229940035436 maltitol Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006418 Brown reaction Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000000463 material Substances 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
- 239000008117 stearic acid Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［従来技術］
糖アルコール脂肪酸エステル、特にショ糖脂肪酸エステ
ルは、食品用の乳化剤として多量に使用されているが、
その製造方法は公知のごとく溶媒法と呼ばれる。例えば
、ジメチルスルホオキシド、ジメチルホルムアミドの様
な溶媒を用いて反応する方法、ショ糖の溶媒としてプロ
ピレングリコールを用いるミクロエマルジョン法及び溶
媒を使用せず、ショ糖、脂肪酸エステル、及び石鹸を加
えて加熱溶融し、１３０〜１８０℃で反応させる無溶媒
法（直接法）がある。これ等の方法はいずれも触媒とし
て、水酸化カリウム、水酸化ナトリウム、炭酸カリウム
、炭酸ナトリウム、炭酸カリウム等を使用する為、反応
物中には石鹸が含まれる。特に、％Ｗｔ媒法（直接法）
では多量の石鹸を使用する為、当然反応物中には、通常
１０〜４０％の石鹸が含まれている。この石鹸を取り除
く為に種々の工夫（例えば時開、６２−２１２５９３の
ごとく反応後、反応物に塩酸を加え、石鹸を分解し、脂
肪酸としたのち、分子蒸留して取り除く方法）がされて
いる。[Detailed Description of the Invention] [Prior Art] Sugar alcohol fatty acid esters, especially sucrose fatty acid esters, are used in large quantities as emulsifiers for foods.
The manufacturing method is known as the solvent method. For example, a reaction method using a solvent such as dimethyl sulfoxide or dimethylformamide, a microemulsion method using propylene glycol as a solvent for sucrose, and a method in which sucrose, fatty acid ester, and soap are added and heated without using a solvent. There is a solventless method (direct method) in which the material is melted and reacted at 130 to 180°C. Since all of these methods use potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, potassium carbonate, etc. as catalysts, soap is included in the reactants. In particular, %Wt medium method (direct method)
Since a large amount of soap is used in this process, the reaction product usually contains 10 to 40% soap. Various methods have been used to remove this soap (for example, as in Jikai, 62-212593, after the reaction, hydrochloric acid is added to the reactant to decompose the soap and turn it into fatty acids, which is then removed by molecular distillation). .
しかしながら、現在市販されているショ糖脂肪酸エステ
ルには１〜５％の石鹸分が含まれており、この石鹸分は
、食品用又は化粧品用等の乳化剤として使用した場合種
々の欠点が生し る。However, currently commercially available sucrose fatty acid esters contain 1 to 5% soap, and this soap content causes various drawbacks when used as an emulsifier for food or cosmetics. .
［本発明の目的］
本発明の発明者は無溶媒法（直接法）又はミクロエマル
ジョン法で得られる反応物を糖アルコール脂肪酸エステ
ル（例えば、ショ糖脂肪酸エステル、マルチトール脂肪
酸エステル、マンニトール脂肪酸エステル、ラクチトー
ル脂肪酸エステル、ソルビトール脂肪酸エステル）を溶
解し、反応物中に含まれる石鹸例えば、ナトリウム、カ
リウム、リチウム等の脂肪酸石鹸を溶解しないか、又は
、溶解しにくい溶媒、例えばヘキサン、シクロヘキサン
、ヘプタン、オクタン、イソオクタン、ベンゼン、キシ
レン、 トルエン等の炭化水素類又はこれらの混液に溶
解した後、分画分子量２．０００〜ｔｏｏ、ｏｏｏの限
外濾過膜により限外濾過する事により、極めて高率的に
石鹸分を除去出来る事を発見し、本発明を完成した。[Objective of the present invention] The inventor of the present invention has prepared a reaction product obtained by a solvent-free method (direct method) or a microemulsion method into a sugar alcohol fatty acid ester (e.g., sucrose fatty acid ester, maltitol fatty acid ester, mannitol fatty acid ester, lactitol fatty acid ester, sorbitol fatty acid ester), and does not dissolve the soaps contained in the reaction product, such as sodium, potassium, lithium, etc., or does not dissolve them easily, such as hexane, cyclohexane, heptane, octane. , isooctane, benzene, xylene, toluene, etc., or a mixture thereof, and then ultrafiltered with an ultrafiltration membrane with a molecular weight cutoff of 2.000~too, ooo, to achieve extremely high efficiency. He discovered that soap can be removed and completed the present invention.
本発明に使用出来る限外濾過膜は、例えばポリイミド、
ポリ（エーテル）スルホン、アセチルセルロース等があ
り、これに限定されるものでない。又膜の排除限界分子
量は２．０００〜ｔｏｏ、０００の範囲、好ましくは５
，０００〜５０．０００の範囲の半透膜が好適に使用出
来る。Ultrafiltration membranes that can be used in the present invention include, for example, polyimide,
Examples include, but are not limited to, poly(ether) sulfone and acetyl cellulose. The exclusion limit molecular weight of the membrane is in the range of 2.000 to 5,000, preferably 5.
,000 to 50,000 can be suitably used.
排除限界公刊ｆｉ ２，０００以下になると、液の透過
速度が極端に遅くなり、又１００，０００以上になると
石鹸の除去等が悪くなり、実用上好まし く ない。When the exclusion limit fi is less than 2,000, the liquid permeation rate becomes extremely slow, and when it exceeds 100,000, soap removal becomes difficult, which is not preferred in practice.
実施例−１
内容ｔＪＬ５００ｎ＋Ｉの撹拌機付反応器にショ糖５７
ｇ、ステアリン酸メチル４９ｇ、ステアリン酸ナトリウ
ム５．５ｇを加え、Ｎ２ガスを流しながら、１５０℃に
加温して溶融する０次に炭酸カリウムＩＯｇを加え、１
５０℃、２０〜３０ａｍＨｇにて４時間反応し、茶かっ
色の反応物ｉ＋＋ｇが得られた。Example-1 Sucrose 57% in a reactor with a stirrer with contents tJL500n+I
g, 49 g of methyl stearate, and 5.5 g of sodium stearate, and heated to 150°C to melt while flowing N2 gas. Next, add IOg of potassium carbonate, and add 10 g of potassium carbonate.
The reaction was carried out at 50° C. and 20 to 30 amHg for 4 hours, and a brownish reaction product i++g was obtained.
この反応物には、ショ糖脂肪酸エステル４２．９％、石
鹸２２．８％が含まれていた。この反応物をシクロヘキ
サン及びｎ−ヘキサンの等容量混液５００１に溶解し、
５０℃圧力３ｋｇ／ｃｓ２にて、ポリエーテルスルホン
平膜分画分子量２０．０００による膜処理を行ない、得
られたろ液を溶媒回収し、石鹸含量を分析した結果、０
．２％含まれていた０石鹸の除去率は９９．１２％であ
った。This reaction product contained 42.9% sucrose fatty acid ester and 22.8% soap. This reactant was dissolved in an equal volume mixture of cyclohexane and n-hexane 5001,
At 50°C and a pressure of 3 kg/cs2, membrane treatment was performed using a polyether sulfone flat membrane with a molecular weight cutoff of 20.000, the resulting filtrate was recovered as a solvent, and the soap content was analyzed.
．． The removal rate of 0 soap, which contained 2%, was 99.12%.
実施例−２
内容Ｊ１５００１１１１の撹拌備付反応器にステアリン
酸３３．７ｇ、炭酸カリウム１６．５ｇを加え、１３０
℃にて加温撹拌し、石鹸を生成させる０次にショ糖１２
６ｇ、ステアリン酸メチル９４．０ｇを加えた後Ｎ２ガ
スを流しながら１４０℃、８０ＩＩＩＩＩＩＨｇにて３
時間反応し、茶かつ色の反応物２４５ｇが得られた。こ
の反応物にはショ糖脂肪酸エステル４３．５％、石ａ６
１７．２％が含まれていた。この反応物をキシレン７７
０１に溶解し、５０℃、圧力３ ｋｇ ／ ａｒｍ”に
てポリエーテルスルホン平膜分画分子ｆｆ１５０，００
０による膜処理を行ない、得られたろ潅を溶媒回収し、
石鹸含量を分析した結果０．３１％含まれていた０石鹸
の除去率は、９８．２％であった。Example-2 33.7 g of stearic acid and 16.5 g of potassium carbonate were added to a reactor with stirring equipment of contents J15001111.
Heat and stir at ℃ to produce soap.
After adding 6g of methyl stearate and 94.0g of methyl stearate, the mixture was heated at 140°C and 80IIIHg while flowing N2 gas.
The reaction was carried out for a period of time, and 245 g of a brown reaction product was obtained. This reaction product contains 43.5% sucrose fatty acid ester, stone a6
It contained 17.2%. This reaction product was converted into xylene 77
Polyether sulfone flat membrane fractionated molecules ff150,00 dissolved in 01 at 50°C and pressure 3 kg/arm
0 membrane treatment, the obtained filtration was collected as a solvent,
As a result of analyzing the soap content, the removal rate of 0.31% soap was 98.2%.
実施例−３
内容ｆ１５００ｍｌの撹拌機付反応器にマルチ）−ル５
７８ステアリン酸メチル４９ｇ、ステアリン酸ナトリウ
ム１５ｇを加え、Ｎ２ガスをン流しながら、１５０℃に
加温して溶融する、次に炭酸カリウムＩＯｇを加え１５
０℃、２０〜３０ｍｍＪにて４時間反応し、茶かっ色の
反応物１２４ｇが得られた。この反応物にはマルチトー
ル脂肪酸エステル３６．２％、石ａａ ２６ 、７％が
含まれていた。この反応物をｎ−ヘキサン５５０ｍ ｌ
に溶解し５０℃、圧力３ ｋｇ ／ 艶２にてポリエー
テルスルホン平膜分画分子量２０，０００による膜処理
を行なう。得られたろ液を溶媒回収し、石鹸含量を分析
した結果０，１５％含まれていた、石鹸の除去率７は９
９．４％であった。Example-3 Multi)-ru 5 in a reactor with a stirrer with a content of 1500 ml
78 Add 49 g of methyl stearate and 15 g of sodium stearate, and heat to 150°C to melt while flowing N2 gas. Next, add 10 g of potassium carbonate.
The reaction was carried out at 0° C. and 20 to 30 mmJ for 4 hours, and 124 g of a brownish reaction product was obtained. The reaction product contained 36.2% maltitol fatty acid ester and 7% aa26. This reaction product was added to 550 ml of n-hexane.
A membrane treatment was performed using a polyethersulfone flat membrane with a molecular weight cutoff of 20,000 at 50° C. and a pressure of 3 kg/gloss 2. The resulting filtrate was collected as a solvent and the soap content was analyzed, and the soap content was 0.15%.The soap removal rate was 9.
It was 9.4%.
比較ｆ５１−１
内容量５００１の撹拌機付反応器に、ショ糖５７ｇ、ス
テアリン酸メチル４９ｇ、ステアリン酸ナトリウム５．
５ｇｔｉ：加え、Ｎ２ガスを流しながら１５０℃に加温
して溶融する０次に炭酸カリウムｌｏｇを加え１５０℃
、２０〜３０ＩｌｌＩＩＨｇにて４時間反応し、茶かつ
色の反応物１１７ｇが得られた。Comparison f51-1 In a reactor equipped with a stirrer with an internal capacity of 5001, 57 g of sucrose, 49 g of methyl stearate, and 5.0 g of sodium stearate were added.
5gti: Add and melt by heating to 150°C while flowing N2 gas. Next, add log potassium carbonate and bring to 150°C.
, 20 to 30 IllIIHg for 4 hours to obtain 117 g of a brown reaction product.
この反応物には、ショ糖脂肪酸エステル４３．１％、石
鹸２３．０％が含まれていた。この反応物をシクロヘキ
サン及びｎ−ヘキサンの等容ｆｌ混液５００ｍ１に溶解
し５０℃、圧力３ ｋｇ ／ ｃｍ ２ポリエーテルス
ルホン平膜、分画分子量１２０．０００による膜処理を
行ない、得られたろ）αを溶媒回収し、石鹸含量を分析
した結果、２．９％含まれていた石鹸の除去率は８７．
４％てあった。This reaction product contained 43.1% sucrose fatty acid ester and 23.0% soap. This reaction product was dissolved in 500 ml of an equal volume mixture of cyclohexane and n-hexane, and subjected to membrane treatment at 50°C and a pressure of 3 kg/cm using a 2-polyethersulfone flat membrane with a molecular weight cutoff of 120.000. As a result of recovering the solvent and analyzing the soap content, the removal rate of soap contained 2.9% was 87.
It was 4%.
比較例−２
内容量５００ｍ１の撹拌機付反応器にステアリン酸３３
．７ｇ、炭酸カリウム１６．５ｇを加え、１３０℃にて
加温撹拌し、石鹸を生成させる０次にショ糖１２６ｇ、
ステアリン酸メチル９４．Ｏｇを加えた後、Ｎ２ガスを
流しながら８０ｍ＋ｗｌ１ｇにて３時間反応し、茶かつ
色の反応物２４９ｇが得られた。Comparative Example-2 Stearic acid 33 was added to a reactor with a stirrer with an internal capacity of 500 m1.
．． Add 7g of potassium carbonate and 16.5g of potassium carbonate, heat and stir at 130°C to produce soap.126g of 0-order sucrose,
Methyl stearate94. After adding Og, the reaction was carried out for 3 hours at 80 m + 1 g of wl while flowing N2 gas, and 249 g of a brown reaction product was obtained.
この反応物には、ショ糖脂肪酸エステル４５．２％、石
鹸１８．９％が含まれていた。この反応物をキシレン７
７０１に溶解し、５０℃、圧力３ ｋｇ ／ ａｗｅ
２にてポリエーテルスルホン平膜、分画分子ａｔ、ｏｏ
ｏにより膜処理を行なったが、ろ液の透過速度が極めて
遅く、膜処理する事が出来なかった。This reaction product contained 45.2% sucrose fatty acid ester and 18.9% soap. This reaction product is converted into xylene 7
Dissolved in 701, 50℃, pressure 3kg/awe
2, polyethersulfone flat membrane, fractionated molecules at, oo
Although membrane treatment was carried out using O, the permeation rate of the filtrate was extremely slow and membrane treatment was not possible.
比較例−３
内容ｆｆ１５００ｎ＋ｌの撹拌機付反応器にショ糖５７
ｇ、ステアリン酸メチル４９ｇ、ステアリン酸ナトリウ
ム５．５ｇを加え、Ｎ２ガスを流しながら、１５０°Ｃ
に加温して溶融する０次に炭酸カリウムＬｏｇを加え１
５０℃、２０〜３０ｍｍＨｇにて４時間反応し、茶かっ
色の反応物１１４ｇが得られた。この反応物には、シヨ
糖脂肪酸エステル４１．５％、石鹸２４．０％が含まれ
ていた。この反応物にメチルエチルケトン５００ｍ１を
加え加温溶解した後、濾過助剤としてケイソウ土５ｇを
加え撹拌分散した後、濾過を行なう、得られた濾液は、
溶剤を回収し、石鹸含量を分析した結果３．６％含まれ
ていた、石鹸の除去率は８５．０％であった。Comparative Example-3 Sucrose 57% in a reactor with a stirrer with contents ff1500n+l
g, 49 g of methyl stearate, and 5.5 g of sodium stearate, and heated to 150°C while flowing N2 gas.
Heat to melt 0 Next, add potassium carbonate Log 1
The reaction was carried out at 50° C. and 20 to 30 mmHg for 4 hours, and 114 g of a brownish reaction product was obtained. This reaction product contained 41.5% sucrose fatty acid ester and 24.0% soap. After adding 500 ml of methyl ethyl ketone to this reaction product and dissolving it by heating, 5 g of diatomaceous earth was added as a filter aid, stirred and dispersed, and then filtered. The obtained filtrate was
The solvent was collected and analyzed for soap content, which was 3.6%, and the soap removal rate was 85.0%.
比較例−４
内容ｆｆｉ５００ｍｌの撹拌機付反応器にマルチトール
５７ｇ、ステアリン酸メチル４９ｇ、ステアリン酸ナト
リウム１５ｇを加え、Ｎ２ガスを流しながら、＋５０°
Ｃに加温して溶融する、次に炭酸カリウムｌｏｇを加え
、１５０℃、２０〜３０ｍｍ１１ｇにて４時間反応し、
茶かっ色の反応物１２６ｇが得られた。この反応物には
マルチトール脂肪酸エステル３７．５％、石鹸２６．０
％が含まれていた。この反応物メチルイソブチルケトン
６００ｍ１を加え加温溶解した後、濾過助剤として、ケ
イソウ±５ｇを加え撹拌分散した後、濾過を行なう。Comparative Example-4 57 g of maltitol, 49 g of methyl stearate, and 15 g of sodium stearate were added to a reactor with a stirrer and the content ffi was 500 ml, and the mixture was heated at +50° while flowing N2 gas.
Melt by heating to C, then add log potassium carbonate and react at 150°C, 20-30mm, 11g for 4 hours,
126 g of a brownish reaction product was obtained. This reaction product contained 37.5% maltitol fatty acid ester and 26.0% soap.
% was included. After adding 600 ml of this reactant methyl isobutyl ketone and dissolving it by heating, ±5 g of diatomaceous material was added as a filter aid and stirred and dispersed, followed by filtration.
得られた濾液は溶剤を回収し、石鹸含量を分析した結果
４．２％含まれていた。石鹸の除去率は８３．８％であ
った。The solvent was recovered from the resulting filtrate, and the soap content was analyzed and found to be 4.2%. The soap removal rate was 83.8%.
Claims (2)
で糖アルコール脂肪酸エステルを製造するにあたり、反
応終了後含有する脂肪酸石鹸を除去する方法として糖脂
肪酸エステルを溶解し、石鹸を溶解しないか又は、溶解
しにくい溶媒に溶解した後、限外濾過を行ない、反応物
に含まれる石鹸を除去する精製方法。(1) When producing sugar alcohol fatty acid esters by a solvent-free method (direct method) or a microemulsion method, the sugar fatty acid ester is dissolved and the soap is not dissolved, or A purification method in which soap contained in the reactant is removed by ultrafiltration after dissolving it in a difficult-to-dissolve solvent.
量が２，０００〜１００，０００の範囲内である事を特
徴とする精製方法(2) A purification method characterized in that the ultrafiltration membrane has at least an exclusion limit molecular weight within the range of 2,000 to 100,000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62311182A JP2807460B2 (en) | 1987-12-09 | 1987-12-09 | Method for purifying fatty acid ester of sugar alcohol or sucrose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62311182A JP2807460B2 (en) | 1987-12-09 | 1987-12-09 | Method for purifying fatty acid ester of sugar alcohol or sucrose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01246293A true JPH01246293A (en) | 1989-10-02 |
| JP2807460B2 JP2807460B2 (en) | 1998-10-08 |
Family
ID=18014075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62311182A Expired - Fee Related JP2807460B2 (en) | 1987-12-09 | 1987-12-09 | Method for purifying fatty acid ester of sugar alcohol or sucrose |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2807460B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008239658A (en) * | 2007-03-26 | 2008-10-09 | Kao Corp | Method for producing oil and fat with reduced free fatty acid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6681284B2 (en) * | 2016-06-23 | 2020-04-15 | 信越化学工業株式会社 | Method for reducing metal of sugar alcohol compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61212593A (en) * | 1985-03-15 | 1986-09-20 | Dai Ichi Kogyo Seiyaku Co Ltd | Purification of sucrose fatty acid ester |
-
1987
- 1987-12-09 JP JP62311182A patent/JP2807460B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61212593A (en) * | 1985-03-15 | 1986-09-20 | Dai Ichi Kogyo Seiyaku Co Ltd | Purification of sucrose fatty acid ester |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008239658A (en) * | 2007-03-26 | 2008-10-09 | Kao Corp | Method for producing oil and fat with reduced free fatty acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2807460B2 (en) | 1998-10-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0288539A (en) | Production of esterified propoxylated glycerine by interestrification | |
| ZA200602133B (en) | Novel salt of donepezil and its polymorphs (donepezi oxalate) | |
| JPS6054945B2 (en) | Plasticizer manufacturing method | |
| JPH01246293A (en) | Method for purifying sugaralcohol ester of fatty acid | |
| JPH02222731A (en) | Recovery method of catalyser | |
| JPH07505623A (en) | Purification of p-aminophenol compositions and direct conversion to N-acetyl-p-aminophenol | |
| EP0747344A1 (en) | Process for the purification and crystallisation of iopamidol | |
| JPH02247151A (en) | Cyclopentenone derivative and preparation thereof | |
| JP3001097B1 (en) | Method for producing sorbic acid | |
| US5206430A (en) | Method for obtaining high-purity cinnamic acid | |
| JP3168263B2 (en) | Novel polymer and drug using the same | |
| JP2618433B2 (en) | Purification method of crude 4-aminophenol | |
| JPS60105664A (en) | Production of 4-methylimidazole | |
| JPS63132868A (en) | Separation of n-vinylacetamide | |
| JP2774076B2 (en) | Method for producing formic acid | |
| JPH0780809B2 (en) | Method of treating methacrylic acid aqueous solution | |
| JPH07330755A (en) | Production of piperonal | |
| JPS63115845A (en) | Manufacture of beta-oxybutyric acid and salt of same by hydrolysis of oligomer of beta-oxybutyric acid in basic medium | |
| WO2006125801A1 (en) | Process for the preparation of adipic acid from n-pentenoic acid | |
| US20050002972A1 (en) | Process of making D-panthenyl triacetate | |
| JPH101494A (en) | Production of colorless and odorless glucopyranoside derivative | |
| JPH0717943A (en) | Production of taurine | |
| JP2946944B2 (en) | Method for producing alkylaminophenols | |
| JPH09278706A (en) | Production of gondoic acid | |
| JPH0670012B2 (en) | Process for producing 2- or 3-aminomethylpiperidine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |