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US 6,593,376 B1Granted
Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups on a di-,oligo- or polyene base
AssigneeSasol Germany GmbH
InventorsMark Rüsch gen. Klaas, Klaus Kwetkat, Siegfried Warwel
Life of this patent
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Abstract
A process for preparing amphiphilic compounds having at least two hydrophilic and at least two hydrophobic groups by reacting an olefinic substrate having at least two double bonds with an organic hydroperoxide to form an oxirane ring, opening, the oxirane ring with an alcohol in the presence of a catalyst system comprising a molybdenum compound as a first catalyst component and a second catalyst component selected from the group consisting of boron trifluoride, alumina, 1,8-diazzabicyclo-(5.4.0)-undec-7-ene, 1,4-diazabicyclo-(2,2,2)-octane.
Claims21
A one-stage process for preparing amphiphilic compounds corresponding to the following formulas I and II:
- comprising oxidizing compounds having hydrocarbyl groups with at least two double bonds with an organic peroxide to form a compound having an oxirane ring, opening said oxirane ring with an alcohol in the presence of a catalyst system comprising a molybdenum compound as a first catalyst component and a second catalyst component selected from the class consisting of boron trifluoride, alumina, 1,8-diazabicyclo-(5.4.0)-undec-7-ene, and 1,4-diazabicyclo-(2.2.2)-octane, wherein R1 and R3, independently of one another, are selected from the group consisting of:
- (A) unbranched saturated hydrocarbon radicals having from 1 to 22 carbon atoms,
- (B) branched saturated hydrocarbon radicals having from 1 to 22 carbon atoms,
- (C) partially fluorinated derivatives of (A),
- (D) partially fluorinated derivatives of (B),
- (E) perfluorinated derivatives of (A),
- (F) perfluorinated derivatives of (B), and mixtures thereof;
- R2 is a spacer selected from the group consisting of:
- (i) an unbranched or branched alkylene chain of formula III
- —CaH2a— (III)
- wherein a is 2 to 18,
- (ii) alicyclic compounds of formula IV
- —CfH2f-cycloC6H10—CgH2g— (IV)
- wherein f and g are independently from 1 to 6,
- (iii) a grouping of formula V
- -3(4),8(9)-di(methylene)-tricyclo [5.2.1.02.6]-decane- (V)
- (iv) a grouping of formula VI
- —CmH2m—(OCnH2n)p—CqH2q— (VI)
- wherein m is 1 to 4, n is 2 to 4, p is 1 to 20, q is 1 to 4 and wherein, optionally, the alkoxide units are mixed alkoxide units, in any arbitrary sequence are present in the group,
- X and Y, independently of one another, are selected from the group consisting of:
- substituents of the formula XV:
- —(C2H4O)α(C3H6O)βH (XV)
- wherein α=0 to 50, β=0 to 60, and α+β=1 to 100;
- and
- substituents of the formula XVI:
- —(C2H4O)γ(C3H6O)δ—FR (XVI)
- wherein γ=0 to 20, δ=0 to 20, and γ+δ=0 to 40, and FR represents a functional radical selected from the group consisting of —CH2COOM, —SO3M, —P(O)(OM)2, —C3H6—SO3M, or —C(O)—C2H3(SO3M)—CO2M′, and M, M′ are alkali, ammonium, alkanol ammonium, or {fraction (1/2 )}alkaline earth metal.
24 more elements
A process for preparing amphiphilic compounds, comprising:
- preparing hydroxyethers of the formula:
- wherein
- R1 and R3 are selected from the group consisting of:
- (A) unbranched saturated hydrocarbon radicals having from 1 to 22 carbon atoms,
- (B) branched saturated hydrocarbon radicals having from 1 to 22 carbon atoms,
- (C) partially fluorinated derivatives of (A),
- (D) partially fluorinated derivatives of (B),
- (E) perfluorinated derivatives of (A),
- (F) perfluorinated derivatives of (B), and mixtures thereof;
- R2 is a spacer selected from the group consisting of:
- (v) an unbranched or branched alkylene chain of formula III
- —CaH2a— (III)
- wherein a is 2 to 18,
- (vi) alicyclic compounds of formula IV
- —CfH2f-cycloC6H10—CgH2g— (IV)
- wherein f and g are independently from 1 to 6,
- (vii) a grouping of formula V
- -3(4),8(9)-di(methylene)-tricyclo [5.2.1.02.6]-decane- (V)
- (viii) a grouping of formula VI
- —CmH2m—(OCnH2n)p—CqH2q— (VI)
- wherein m is 1 to 4, n is 2 to 4, p is 1 to 20, q is 1 to 4 and wherein, optionally, the alkoxide units are mixed alkoxide units, in any arbitrary sequence are present in the group;
- by:
- (1) reacting an olefinic substrate having hydrocarbyl groups with at least two double bonds with an organic hydroperoxide to form an oxirane ring,
- (2) opening said oxirane ring with an alcohol in the presence of a molybdenum compound as a first catalyst component and a second catalyst component selected from the group consisting of boron trifluoride, an alumina, 1,8-diazabicyclo-(5.4.0)-undec-7-ene, and 1,4-diazabicyclo-(2.2.2)-octane, and
- (3) preparing the amphiphilic compounds by
- (3.1) alkoxylating the hydroxyethers with an alkoxylating agent to yield an amphiphilic nonionic compound, or
- (3.2) reacting the hydroxyethers to form an amphiphilic ionic compound.
24 more elements
Dependencies are inferred from the claim text.