PL77802B2 - - Google Patents
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- Publication number
- PL77802B2 PL77802B2 PL15123971A PL15123971A PL77802B2 PL 77802 B2 PL77802 B2 PL 77802B2 PL 15123971 A PL15123971 A PL 15123971A PL 15123971 A PL15123971 A PL 15123971A PL 77802 B2 PL77802 B2 PL 77802B2
- Authority
- PL
- Poland
- Prior art keywords
- butyl ester
- double bond
- surfactants
- solvents
- dioxane
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 claims description 2
- HGWAKQDTQVDVRP-OKULMJQMSA-N butyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCCC HGWAKQDTQVDVRP-OKULMJQMSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- -1 Alkylbenzene sulfonates Chemical class 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 241001580017 Jana Species 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
Pierwszenstwo: 25.10.1971 (P. 151239) Zgloszenie ogloszono: 30.05.1973 Opis patentowy opublikowano: 30.05.1975 77802 KI. 12o,23/03 MKP C07c 143/90 Urzedu Pcri*ito* \ Twórcywynalazku: Kazimierz Kozlowski, Grazyna Politowicz, Antoni Rózyczka Uprawniony z patentu tymczasowego: Wyzsza Szkola Inzynierska im. Jana i Jedrzeja Sniadeckich, Bydgoszcz (Polska) Sposób otrzymywania zwiazków powierzchniowo-czynnych Przedmiotem wynalazku jest sposób otrzymywania zwiazków powierzchniowo-czynnych.Znane sa zwiazki powierzchniowo-czynne otrzymywane przez dzialanie srodkami sulfonujacymi lub siarczanujacymi na oleje i tluszcze.Srodki powierzchniowo-czynne posiadaja grupe alkjlosulfonowa na koncu, wzglednie przy koncu lancucha alifatycznego. Alkilobenzenosulfoniany posiadaja grupe sulfonowa w pierscieniu aromatycznym; takie srodki powierzchniowo-czynne maja dobre wlasnosci piorace. Jezeli grupa sulfonowa znajduje sie w srodku lancucha ali¬ fatycznego, to zwiazek taki posiada dobre wlasnosci zwilzajace.Sulfonowanie przy pomocy kwasu siarkowego, kwasu chlorosulfonowego lub oleum nie prowadzi do otrzymania pochodnej sulfonowej zawierajacej podwójne wiazanie, poniewaz wymienione srodki sulfonujace przylaczaja sie latwo do wiazania podwójnego.Przeprowadzone dotychczasowo próby przy pomocy kwasu siarkowego czy oleum, nie daly zwiazku powierzchniowo-czynnego z podwójnym wiazaniem, o lagodnym dzialaniu; produkty reakcji ulegly zesmoleniu.Celem wynalazku jest usuniecie znanych wad przez opracowanie nowego sposobu otrzymywania zwiazków powierzchniowo-czynnych na bazie oleju rycynowego i aminoalkoholi.Istota wynalazku polega na tym, ze przeprowadza sie siarczanowanie estru buty Iowego kwasu rycynolowe- go za pomoca kompleksów; S03-dioksan lub S03-pirydyna w rozpuszczalnikach organicznych takich, jak: chlorek etyleniu, chloroform, czterochlorek wegla, czterochloroetan, dwuchloroetylen, bez naruszenia wiazania podwójnego. Temperature reakcji utrzymuje sie w zakresie od -10 do +20°C, najlepiej 0—5°C. Nastepnie na otrzymyna pochodna sulfonowa, zawierajaca podwójne wiazanie dziala sie aminoalkoholami takimi, jak: etanoloaminy, propanoloaminy, butanoloaminy.Nowy sposób otrzymywania zwiazku powierzchniowo-czynnego na bazie oleju rycynowego i aminoalkoho¬ li, z zachowaniem wiazania podwójnego w kwasie rycynolowym i posiadajacym alkilowa grupe sulfamidowa w srodku lancucha, zapewnia lagodne dzialanie wymienionego srodka.Zalkilowany butylan rycynolowy posiada dobre wlasnosci zwilzajace i emulgujace.Zaleta techniczna sposobu wedlug wynalazku jest stosunkowo prosta synteza, która nie wymaga aparatów cisnieniowych.Przyklad. W kolbie trójszyjnej na 250 ml umieszcza sie 100 g rycynolanu butylu i dodaje sie zwkraplacza 52 g kompleksu S03-dioksan (o zawartosci S03 okolo 48%) w 94 ml chlorku etylenu. Podczas2 77 802 mieszania mechanicznego zawartosc kolby utrzymuje sie w zakresie temperatur 0 — 5°C do czasu, az caly trójtlenek siarki nie przereaguje, co trwa okolo 6 godzin. Nastepnie do otrzymanej pochodnej sulfonowej wkrapla sie 42 g trójetanoloaminy, podczas energicznego mieszania. Wydajnosc reakcji jest niemal ilosciowa. PLPriority: October 25, 1971 (P. 151239) Application announced: May 30, 1973 Patent description was published: May 30, 1975 77802 KI. 12o, 23/03 MKP C07c 143/90 Pcri * ito * Office \ Creators of the invention: Kazimierz Kozlowski, Grazyna Politowicz, Antoni Rózyczka Temporary patent holder: Wyższa Szkoła Inżynierska im. Jana i Jedrzeja Sniadeckich, Bydgoszcz (Poland) Method for the preparation of surfactants The subject of the invention is a method of obtaining surfactants. There are known surfactants obtained by treating oils and fats with sulphating or sulphating agents. Surfactants have an alkylsulfonate group. at the end or at the end of an aliphatic chain. Alkylbenzene sulfonates have a sulfone group in the aromatic ring; such surfactants have good detergency properties. If the sulfonate group is in the middle of an aliphatic chain, the compound has good wetting properties. Sulfonation with sulfuric acid, chlorosulfonic acid or oleum does not result in a sulfone derivative containing a double bond, since the sulfonating agents mentioned bind easily to the double bond . The tests carried out so far with sulfuric acid or oleum have not produced a double-bonded surfactant with a mild effect; the reaction products became salted. The aim of the invention is to eliminate the known drawbacks by developing a new method for the preparation of surfactants based on castor oil and amino alcohols. The essence of the invention consists in the sulphation of the butyl ester of ricinoleic acid by means of complexes; S03-dioxane or SO3-pyridine in organic solvents such as: ethyl chloride, chloroform, carbon tetrachloride, tetrachlorethane, dichloroethylene, without breaking the double bond. The reaction temperature is in the range of -10 to + 20 ° C, preferably 0-5 ° C. Then, the obtained sulfone derivative, containing the double bond, is treated with amino alcohols such as: ethanolamine, propanolamine, butanolamine. A new method of obtaining a surfactant based on castor oil and aminoalcohols, maintaining the double bond in ricinoleic acid and having a sulfamide alkyl group in the middle of the chain, it ensures a gentle action of the agent mentioned. The alkylated ricinole butylate has good wetting and emulsifying properties. The technical advantage of the method according to the invention is a relatively simple synthesis, which does not require pressure apparatus. 100 g of butyl ricinoleate are placed in a 250 ml three-necked flask and a condenser is added of 52 g of the SO3-dioxane complex (with an SO3 content of about 48%) in 94 ml of ethylene chloride. During the mechanical agitation, the contents of the flask are kept in the temperature range of 0-5 ° C until all the sulfur trioxide has reacted, which takes about 6 hours. Then 42 g of triethanolamine are added dropwise to the obtained sulfone derivative while stirring vigorously. The yield of the reaction is almost quantitative. PL
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15123971A PL77802B2 (en) | 1971-10-25 | 1971-10-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15123971A PL77802B2 (en) | 1971-10-25 | 1971-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL77802B2 true PL77802B2 (en) | 1975-04-30 |
Family
ID=19956045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15123971A PL77802B2 (en) | 1971-10-25 | 1971-10-25 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL77802B2 (en) |
-
1971
- 1971-10-25 PL PL15123971A patent/PL77802B2/pl unknown
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