BE457532A - - Google Patents
Info
- Publication number
- BE457532A BE457532A BE457532DA BE457532A BE 457532 A BE457532 A BE 457532A BE 457532D A BE457532D A BE 457532DA BE 457532 A BE457532 A BE 457532A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- carboxylic acids
- agents
- products
- functional derivatives
- Prior art date
Links
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 for example Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- LXVAEMFXVFEJNV-UHFFFAOYSA-N decanedioic acid;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.OC(=O)CCCCCCCCC(O)=O LXVAEMFXVFEJNV-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/02—Formation or introduction of functional groups containing sulfur of sulfo or sulfonyldioxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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La société dite : Böhme Fettchemie-Gesellschaft mit beschränkter Haftung à Chemnitz, Saxe (Allemagne). Procédé de fabrication de produits de sulfonation à activité superificielle. Convention Internationale : Demande de brevet allemand déposée le 20 septembre 1943.
On a trouvé qu'on peut obtenir des produits de sulfonation à activité superficielle lorsqu'on traite des hydropyranalcànols conjointement avec des acides carboxyliques ou leurs dérivés fonctionnels ou avec des combinaisons contenant des radicaux'hydroxyles, par des agents de sulfonation qui contiennent éventuellement des additions capables de fixer l'eau et qu'on neutral is e les produits de réaction par des bases inorganiques ou organiques. Au lieu de cela, on peut aussi faire.réagir les hydropyranalcanols tout d'abord avec des acides car- boxyliques ou leurs dérivés fonctionnels ou encore avec des combinaisons contenant des radicaux hydroxyles et traiter alors les produits intermédiaires formés par des agents de sulfonation.
Les hydropyranalcanols servant de matière pre- mière peuvent par exemple être obtenus par cyclisation des dérivés du dîol-1,5 ou de diols à radicaux hydroxyles encore plus éloignés l'un'de l'autre qui contiennent en outre encore un troisième radical hydroxyle ou un radical réactionnel échangeable contre un hydroxyle, ou à partir
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EMI2.1
de d-formyldihydropyrane obtenu par dimérisati on de l'acroléine, et qu'on soumet à l'hydrogénation tel c,uel ou après condensation avec des aldéhydes saturées ou non saturées, telles que l'acétaldéhyde et ses homologues,
EMI2.2
la crotonaldéhyde, 1 tocte.trienal, etc.., ou avec 6S cétones.
Comme acides carboxyliques, entrent eu li :..;ne de compte tous les acides carboxyliques satures et non. saturés à chaîne ouverte ou cyclée, ramifiée ou non et le cas échéant une chaine d'hydrocarbures portant des subetituants, en particulier ceux à plus de 6 atomes de carbone, tels que les acides des graisses naturelles ou de
EMI2.3
l'oxydation de la paraffine, l'acide montanique, les aïdes résiniques, les acides naphtéliques, l'scide adipique l'acide sébacique, l'acide phtalique, l'acide salicylique, l'acide 12-oxyst6arique, l'acide lêvulinicue, l'acide ct. -romolaurique. En tant que dérivés fonctionnels de ceux-ci, on peut utiliser les esters des alcools monoou polyvalents tels que par exemple les esters cireux et les glycérides, de plus, les haloGénures et les anhydrides d'acides.
Comme suostances hydroxylées, entrent en ligne
EMI2.4
de compte les alcools mono- ou polyvalents correspoudcnts aux acides cités, ainsi que les phénols. Pour la fabriaction des produits intermédiaires acylés ou éthérifiés, on
EMI2.5
peut le cas échéant avoir recours auxhalogénures, aux es- ters sulfuriques, aux combinaisons avec les alcalis, etc.. Exemple :
EMI2.6
Du -tétrahydropyryl] méthanol obtenu ;,r h;;Tdrogénation d'aorolsine dimère est avec m indice de saponification d'environ 240, à l'aide d'acides gras de l'oxydation de la paraffine.
Une mole de l'ester estmélangée à 1,1 mole d'acide chlorosulfonique technique à
EMI2.7
température peu élevée et o.[:;i tée, usCJ.u' 2l dissolution lipide du produit de réaction, une chauffe au oiin-..ioie étant utilisée pour accélérer la réaction. On neutralise ensuite
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par coulée sous réfrigération dans une lessive de soude.
La neutralisation eut également se faire à l'aide d'ammo- niaque ou de bases organiques.
Selon le choix des matières premières, les produits sont plus ou moins solubles dans l'eau. Leurs solutions aqueuses présentent des propriétés à activité'superficielle. Par conséquent, les produits peuvent servir comme mouillants, détergents, agents de dispersion, agents, de lavage, et pour d'autres buts semblables.
Revend!cations.
1. Procédé de fabrication de produits de sulfonation à activité superficielle, caractérisé en ce que l'on trame des hydropyranaloanols conjointement avec des acides car-' boxyliques ou leurs'dérivés fonctionnels ou encore avec des combinaisons contenant des radicaux hydroxyles, par des, agents de sulfonation qui contiennent éventuellement des additions capables de fixer l'eau, et'qu'on neutralise les produits de réaction par des bases inorganiques ou organi- ques.
<Desc / Clms Page number 1>
The company known as: Böhme Fettchemie-Gesellschaft mit beschränkter Haftung in Chemnitz, Saxony (Germany). Process for the production of surface activity sulfonation products. International Convention: German patent application filed on September 20, 1943.
It has been found that surface active sulfonation products can be obtained when hydropyranalkanols are treated together with carboxylic acids or their functional derivatives or with combinations containing hydroxyl radicals, with sulfonating agents which optionally contain additions. capable of fixing water and that the reaction products are neutralized with inorganic or organic bases. Instead, the hydropyranalkanols can also be reacted first with carboxylic acids or their functional derivatives or alternatively with combinations containing hydroxyl groups and then treated the intermediates formed with sulfonating agents.
The hydropyranalkanols serving as raw material can, for example, be obtained by cyclization of derivatives of 1,5-dlol or of diols with hydroxyl groups even further apart from each other which additionally contain a third hydroxyl group or a reaction radical exchangeable against a hydroxyl, or from
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EMI2.1
of d-formyldihydropyran obtained by dimerization of acrolein, and which is subjected to hydrogenation such as or after condensation with saturated or unsaturated aldehydes, such as acetaldehyde and its homologues,
EMI2.2
crotonaldehyde, 1 tocte.trienal, etc., or with 6S ketones.
As carboxylic acids, enter had li: ...; do not count all saturated carboxylic acids and not. saturated open or cycled chain, branched or not and, where appropriate, a hydrocarbon chain carrying subetituents, in particular those with more than 6 carbon atoms, such as the acids of natural fats or of
EMI2.3
oxidation of paraffin, montanic acid, resin aids, naphthelic acids, adipic acid sebacic acid, phthalic acid, salicylic acid, 12-oxyst6aric acid, levulinic acid , acid ct. -romolauric. As functional derivatives thereof, esters of mono or polyvalent alcohols such as, for example, waxy esters and glycerides, furthermore, halides and acid anhydrides can be used.
As hydroxylated suostances, come in line
EMI2.4
of account the mono- or polyvalent alcohols corresponding to the acids mentioned, as well as the phenols. For the manufacture of acylated or etherified intermediates, we
EMI2.5
can if necessary have recourse to halides, sulfuric esters, combinations with alkalis, etc. Example:
EMI2.6
From -tetrahydropyryl] methanol obtained;, r h ;; The dimeric aorolsin hydrogenation has a saponification number of about 240, using fatty acids from the oxidation of paraffin.
One mole of the ester is mixed with 1.1 moles of technical chlorosulfonic acid
EMI2.7
low temperature and low temperature dissolving lipid from the reaction product, heating with oiin - .. ioie being used to accelerate the reaction. We then neutralize
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by pouring under refrigeration in a sodium hydroxide solution.
Neutralization could also be carried out using ammonia or organic bases.
Depending on the choice of raw materials, the products are more or less soluble in water. Their aqueous solutions exhibit properties with superficial activity. Therefore, the products can serve as wetting agents, detergents, dispersing agents, washing agents, and for other similar purposes.
Resells! Cations.
1. A method of manufacturing sulfonation products with surface activity, characterized in that hydropyranaloanols are woven together with carboxylic acids or their functional derivatives or alternatively with combinations containing hydroxyl radicals, by agents which optionally contain additions capable of fixing water, and which neutralizes the reaction products with inorganic or organic bases.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE457532A true BE457532A (en) |
Family
ID=110981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE457532D BE457532A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE457532A (en) |
-
0
- BE BE457532D patent/BE457532A/fr unknown
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