PL133768B2 - Process for preparing esters of sorbitans - Google Patents
Process for preparing esters of sorbitans Download PDFInfo
- Publication number
- PL133768B2 PL133768B2 PL24427483A PL24427483A PL133768B2 PL 133768 B2 PL133768 B2 PL 133768B2 PL 24427483 A PL24427483 A PL 24427483A PL 24427483 A PL24427483 A PL 24427483A PL 133768 B2 PL133768 B2 PL 133768B2
- Authority
- PL
- Poland
- Prior art keywords
- catalyst
- sorbitol
- sorbitans
- temperature
- esters
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 9
- 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 claims description 7
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 7
- 229960002920 sorbitol Drugs 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000001488 sodium phosphate Substances 0.000 claims description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 2
- 235000011008 sodium phosphates Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania estrów sorbitanów, niejonowych zwiazków powierzchniowo czynnych, które maja szerokie zastosowanie w wielu galeziach przemyslu chemi¬ cznego, glównie jako emulgatory typu woda — olej.Znany sposób otrzymywania estrów sorbitanów opisany w czasopismie „Wiadomoscichmie- czne", rocznik XXIII, zeszyt 5 (263), 1969 polega na ogrzewaniu w czasie 4-5 godzin w temperatu¬ rze 200 do 240°C w atmosferze gazu obojetnego równomolowych ilosci D-sorbitu z kwasem tluszczowym w obecnosci katalizatora w postaci mocnej zasady lub mocnego kwasu. W zaleznosci od rodzaju uzytego katalizatora powstaje mieszanina estrów róznych anhydrosorbitów oraz niewielkie ilosci niezestryfikowanych anhydrosorbitów, kwasu tluszczowego, D-sorbitu. Uzycie jako katalizatora kwasu siarkowego lub kwasu fosforowego powoduje powstawanie przewazajacej ilosci estru dwuanhydrosorbitu, gdy tymczasem w obecnosci wodorotlenkusodu tworzy sie przede wszystkim ester 1,4-monoanhydrosorbitu. Podczas estryfikacji D-sorbitu równomolowa iloscia kwasu mirystynowego, polmitynowego, stearynowego otrzymuje sie odpowiednie monoestry róz¬ nych anhydrosorbitów.Tesurowe estry sa woskowatymi cialami stalymi o zabarwieniu przewaznie ciemnobrazowym. Odbarwienie ich przy pomocy wegla aktywnego czy tez utleniaczy takich jak podchloryn sodowy lub nadtlenek wodoru nie daje zadawalajacych wyników i tym samym unie¬ mozliwiaja stosowanie tych estrów do wyrobów farmaceutycznych czy tez kosmetycznych.Wynalazek dotyczy sposobu wytwarzania estrów sorbitanów przez ogrzewanie w temperatu¬ rze 200 do 250°C w atmosferze gazu obojetnego D-sorbit z kwasem tluszczowym w obecnosci katalizatora.Istota wynalazku polega na tym, ze stosuje sie katalizator w postaci fosforanu sodowego w ilosci od 0,1% do 5% masowych w stosunku do calkowitej ilosci wsadu.Zaleta wynalazku jest to, ze otrzymuje sie produkt o zadanych wlasciwosciach przy pomocy latwo dostepnego i taniego katalizatora.Przedmiot wynalazku przedstawiony jest w dwóch przykladach wykonania.Przyklad I. Do93g (0,5 mola) D-sorbitu pólwodnego wprowadza sie 142,2g (0,5 mola) czystego kwasu stearynowego, ogrzewa sie, a po stopieniu substratów miesza sie i przepuszcza azot.Intensywnosc ogrzewania reguluje sie tak, aby temperatura mieszaniny reakcyjnej wynosila 230°C2 133 768 po uplywie 0,5 godziny. W tej temperaturze wprowadza sie nastepnie 1,6 g fosforanu jednosodo- wego jednowodnego i ogrzewa sie 2 godziny. W czasie trwania reakcji odbiera sie wode reakcyjna i kntroluje liczbe kwasowa mieszaniny reakcyjnej. Po uplywie okreslonego wyzej czasu przerywa sie ogrzewanie i schladza wytworzony produkt do temperatury pokojowej. Otrzymuje sie 210g produktu w postaci bialego wosku o LK= 13,0, LE= 134,0, LOH= 190,0.Przyklad II. Do 93 g (0,5 mola) D-sorbitu pólwodnego wprowadza sie 141,2g (0,5 mola) czystego kwasu oleinowego. Nastepnie przy mieszaniu i przepuszczaniu azotu, temperature mie¬ szaniny reakcyjnej podnosi sie do 230°C w ciagu 0,5 godziny, wprowadza sie l,4g fosforanu jednosodowego jednowodnego i dalej proces prowadzi sie jak w przykladzie I. Otrzymuje sie 208 g produktu w postaci brazowej cieczy o LK= 14,2, LE= 129,8, LOH= 190.Zastrzezenie patentowe Sposób wytwarzania estrów sorbitanów polegajacy na ogrzewaniu w atmosferze gazu obojet¬ nego, w temperaturze 200 do 250°C D-sorbitu z kwasem tluszczowym w obecnosci katalizatora, znamienny tym, ze stosuje sie katalizator w postaci fosforanu sodowego w ilosci od 0,1% do 5% masowych w stosunku do calkowitej ilosci wsadu.Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 100 zl PLThe subject of the invention is a method for the production of sorbitan esters, non-ionic surfactants, which are widely used in many branches of the chemical industry, mainly as water-oil emulsifiers. Issue 5 (263), 1969 consists of heating for 4-5 hours at 200 to 240 ° C in an inert gas atmosphere of equimolar amounts of D-sorbitol with fatty acid in the presence of a strong base or strong acid catalyst. the type of catalyst used results in a mixture of esters of various anhydrosorbits and small amounts of non-esterified anhydrosorbits, fatty acid, D-sorbitol. -monoanhydrosorbitol With the esterification of D-sorbitol with equimolar amounts of myristic, polymithic, and stearic acids, the corresponding monoesters of various anhydrosorbits are obtained. The test esters are waxy solids, usually dark brown in color. Discoloration of them with the use of activated carbon or oxidants such as sodium hypochlorite or hydrogen peroxide does not give satisfactory results and thus make it impossible to use these esters in pharmaceutical or cosmetic products. The invention relates to a method of producing sorbitan esters by heating at a temperature of 200 to 250 ° C in an inert gas atmosphere of D-sorbitol with fatty acid in the presence of a catalyst. The essence of the invention is that a sodium phosphate catalyst is used in the amount of 0.1% to 5% by weight in relation to the total amount of charge. According to the invention, a product with the desired properties is obtained with the aid of an easily available and cheap catalyst. The subject of the invention is presented in two examples of implementation. Example I. Do93g (0.5 mol) of D-sorbitol as a half-water is introduced into 142.2 g (0, 5 moles) of pure stearic acid, heated, and after the substrates have melted, it is stirred and nitrogen is passed through. it is so that the temperature of the reaction mixture is 230 ° C 133 768 after 0.5 hour has elapsed. At this temperature, 1.6 g of monosodium phosphate monohydrate are then introduced and the mixture is heated for 2 hours. During the course of the reaction, the reaction water is withdrawn and the acid number of the reaction mixture is controlled. After the time specified above has elapsed, the heating is stopped and the product formed is cooled to room temperature. 210 g of the product are obtained in the form of a white wax with LK = 13.0, LE = 134.0, LOH = 190.0. Example II. 141.2 g (0.5 mol) of pure oleic acid are introduced into 93 g (0.5 mol) of D-sorbitan hemihydrate. Then, while stirring and passing nitrogen, the temperature of the reaction mixture was raised to 230 ° C in 0.5 hours, 1.4 g of monosodium phosphate monohydrate were introduced and the process was continued as in Example I. 208 g of product were obtained in the form of brown liquid with LK = 14.2, LE = 129.8, LOH = 190. Patent claim A method of producing sorbitan esters based on heating in an inert gas at a temperature of 200 to 250 ° C D-sorbitol with fatty acid in the presence of a catalyst, characterized in that the sodium phosphate catalyst is used in an amount from 0.1% to 5% by weight in relation to the total amount of charge. Pracownia Poligraficzna UP PRL. Mintage 100 copies Price PLN 100 PL
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL24427483A PL133768B2 (en) | 1983-10-22 | 1983-10-22 | Process for preparing esters of sorbitans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL24427483A PL133768B2 (en) | 1983-10-22 | 1983-10-22 | Process for preparing esters of sorbitans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL244274A2 PL244274A2 (en) | 1984-08-27 |
| PL133768B2 true PL133768B2 (en) | 1985-06-29 |
Family
ID=20018924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL24427483A PL133768B2 (en) | 1983-10-22 | 1983-10-22 | Process for preparing esters of sorbitans |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL133768B2 (en) |
-
1983
- 1983-10-22 PL PL24427483A patent/PL133768B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL244274A2 (en) | 1984-08-27 |
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