WO1996036586A1 - Esters d'acide pivalique d'alcools aliphatiques alcoxyles - Google Patents

Esters d'acide pivalique d'alcools aliphatiques alcoxyles Download PDF

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Publication number
WO1996036586A1
WO1996036586A1 PCT/EP1996/002029 EP9602029W WO9636586A1 WO 1996036586 A1 WO1996036586 A1 WO 1996036586A1 EP 9602029 W EP9602029 W EP 9602029W WO 9636586 A1 WO9636586 A1 WO 9636586A1
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WO
WIPO (PCT)
Prior art keywords
pivalic acid
acid esters
esters
pivalic
alcohol
Prior art date
Application number
PCT/EP1996/002029
Other languages
German (de)
English (en)
Inventor
Richard Baur
Helmut GÜMBEL
Bernd Burkhart
Alfred Oftring
Gerhard Wolf
Johannes Perner
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to JP8534535A priority Critical patent/JPH11505235A/ja
Priority to EP96919771A priority patent/EP0825973A1/fr
Publication of WO1996036586A1 publication Critical patent/WO1996036586A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds

Definitions

  • the present invention relates to new pivalic acid esters of alkoxylated aliphatic alcohols of the general formula I
  • R is the remainder of an aliphatic alcohol with 6 to 30 C atoms
  • n an average value from 1 to 20
  • m an average value from 0 to 6.
  • the invention relates to the preparation of the compounds I, their use as surface-active substances, especially as a surfactant with foam-suppressing properties, and formulations with these surface-active substances.
  • DE-A 1 243 312 discloses esters of alkoxylated aliphatic alcohols, for example acetic acid or hydroxyisobutyric acid, as low-foaming nonionic surface-active compounds. However, they leave something to be desired when used as foam-suppressing surfactants. In particular, strong foaming is observed in machine cleaning processes.
  • the invention was therefore based on esters of alkoxylated aliphatic alcohols with improved foam-suppressing properties.
  • esters I defined at the outset were found.
  • Preferred alcohols R-OH from which the compounds I according to the invention are derived are preferably:
  • unbranched primary alkanols with 6 to 30 C atoms such as hexyl, heptyl, octyl, nonyl, decyl, undecyl alcohol and especially lauryl, myristyl, cetyl and stearyl alcohol
  • unbranched primary alkenols with 6 to 30 carbon atoms such as linolyl and linolenyl alcohol, especially oleyl alcohol.
  • These alcohols which are also called fatty alcohols, are mostly of natural origin and are therefore preferred. Mixtures of these alcohols, as in their natural occurrence, e.g. the coconut fatty alcohol, which is a mixture of lauryl alcohol and myristyl alcohol as main components.
  • alcohols and alcohol mixtures of synthetic provenance come into consideration, e.g. branched alkanols and alkenols such as 2-ethylhexyl, isooctyl, isononyl, 3-propylheptyl, isodecyl and isotridecyl alcohol.
  • branched alkanols and alkenols such as 2-ethylhexyl, isooctyl, isononyl, 3-propylheptyl, isodecyl and isotridecyl alcohol.
  • oxo alcohols which are obtained by hydroformylation of ⁇ -olefins and further reactions, are particularly suitable.
  • the degree of ethoxylation is preferably 4 to 12.
  • the polypropylene glycol ether group has an average degree of propoxylation of 0 to 6.
  • To prepare the compounds I 1 mol of the alcohol R-OH is reacted with n mol of ethylene oxide in a manner known per se and the esterification product is then esterified with pivalic acid or one of its functional derivatives.
  • the reaction with ethylene oxide takes place under the known alkoxylation conditions, preferably in the presence of an alkaline catalyst such as alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, in particular alkaline earth metal hydroxides such as calcium hydroxide, barium hydroxide and strontium hydroxide and hydrotalcite (Al 2 Mg 6 (OH) ⁇ 6 C0 3 -4H 2 0). If appropriate, it is then reacted with m mol of propylene oxide.
  • an alkaline catalyst such as alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, in particular alkaline earth metal hydroxides such as calcium hydroxide, barium hydroxide and strontium hydroxide and hydrotalcite (Al 2 Mg 6 (OH) ⁇ 6 C0 3 -4H 2 0).
  • pivalic anhydride and pivalic acid esters are suitable for acid-catalyzed esterification or transesterification, the numerous configurations of which are generally known with regard to the acid, the removal of the water of reaction, the temperature and the reaction time, so that further explanations are unnecessary.
  • the acid chloride is preferably used as the starting component.
  • the reaction can be carried out in the presence of an inert solvent such as toluene, acetone, diethyl ether, hexane, decane and petroleum ether, but is preferably solvent-free.
  • an inert solvent such as toluene, acetone, diethyl ether, hexane, decane and petroleum ether, but is preferably solvent-free.
  • the acid chloride in an equimolar amount to the alkoxylated alcohol, and the range from 40 to 80 ° C. is recommended for the reaction temperature.
  • the released hydrogen chloride can be bound with a base such as triethylamine or pyridine, but it is preferably removed by means of an inert gas stream, e.g. of a nitrogen stream.
  • reaction product is expediently freed from traces of acid, for example with sodium carbonate.
  • the pivalic acid esters I according to the invention have good surface-active properties, which enables their use in many areas of application. They are particularly notable for their considerably reduced foaming power and very good foam-suppressing action, compared to known esters of alkoxylated aliphatic alcohols. These properties enable use in areas of application in which foam formation is undesirable. They are therefore particularly suitable as agents for machine cleaning in the household and industry, either alone or in a mixture with other surface-active agents.
  • esters of the alkoxylated alcohols with other aliphatic carboxylic acids were prepared for comparison, specifically according to DE-A 1 243 312, Example 3.
  • the cloud point, the foaming power, the surface tension and the foam damping in the dishwasher were investigated as the application properties of the esters.
  • the cloud point was determined in accordance with DIN 53917. The temperature above which the solution becomes cloudy and is therefore present as a mixture of two liquid phases is determined. The lower the cloud temperature, the lower the foam capacity.
  • the foaming power was determined in accordance with DIN 53902 by measuring the foam volume in ml one minute after the end of foam generation.
  • the surface tension was determined in accordance with DIN 53924 by measuring the force in mN / m which is necessary to pull a horizontally suspended ring or bracket out of the liquid surface.
  • Foam is produced in a commercial household dishwasher by adding an egg, with a twelve-minute heating phase being carried out. During this time, the average number of revolutions of the spray arm per minute is determined. Foam formation reduces the number of revolutions due to the reduced recoil force and thus represents a measure of the suitability of surfactants in cleaning machines.
  • esters according to the invention are superior to those of the prior art (according to DE-A 1 243 312) in all their application properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Esters d'acide pivalique d'alcools aliphatiques alcoxylés répondant à la formule (I), dans laquelle R désigne le reste d'un alcool aliphatique ayant 6 à 30 atomes de carbone, A désigne le groupement 1,2-propylène, n désigne une valeur moyenne comprise entre 1 et 20 et m désigne une valeur moyenne comprise entre 0 et 6. Ces composés (I) sont utiles comme agents tensioactifs peu moussants et antimousse.
PCT/EP1996/002029 1995-05-19 1996-05-11 Esters d'acide pivalique d'alcools aliphatiques alcoxyles WO1996036586A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP8534535A JPH11505235A (ja) 1995-05-19 1996-05-11 アルコキシル化脂肪族アルコールのピバル酸エステル
EP96919771A EP0825973A1 (fr) 1995-05-19 1996-05-11 Esters d'acide pivalique d'alcools aliphatiques alcoxyles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1995118476 DE19518476A1 (de) 1995-05-19 1995-05-19 Pivalinsäureester alkoxylierter aliphatischer Alkohole
DE19518476.9 1995-05-19

Publications (1)

Publication Number Publication Date
WO1996036586A1 true WO1996036586A1 (fr) 1996-11-21

Family

ID=7762391

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/002029 WO1996036586A1 (fr) 1995-05-19 1996-05-11 Esters d'acide pivalique d'alcools aliphatiques alcoxyles

Country Status (4)

Country Link
EP (1) EP0825973A1 (fr)
JP (1) JPH11505235A (fr)
DE (1) DE19518476A1 (fr)
WO (1) WO1996036586A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1243312B (de) * 1962-10-04 1967-06-29 Roehm & Haas Gmbh Schaumarme grenzflaechenaktive Verbindungen
DE2257546A1 (de) * 1971-11-29 1973-06-07 Dow Chemical Co Hydraulik-fluessigkeit
DE4225236A1 (de) * 1992-07-30 1994-02-03 Henkel Kgaa Endgruppenverschlossene Antischaummittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1243312B (de) * 1962-10-04 1967-06-29 Roehm & Haas Gmbh Schaumarme grenzflaechenaktive Verbindungen
DE2257546A1 (de) * 1971-11-29 1973-06-07 Dow Chemical Co Hydraulik-fluessigkeit
DE4225236A1 (de) * 1992-07-30 1994-02-03 Henkel Kgaa Endgruppenverschlossene Antischaummittel

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 69, no. 5, 29 July 1968, Columbus, Ohio, US; abstract no. 18556v, HENRY F. LEDERLE: "Preparation and physical properties of some trialkylacetic acid esters." page 1733; column R; XP002010476 *
HENRY F. LEDERLE: "Preparation and physical properties of some trialkylacetic acid esters.", IND.ENG.CHEM.,PROCESS DES.DEVELOP., vol. 7, no. 2, 1968, pages 94 - 96 *

Also Published As

Publication number Publication date
DE19518476A1 (de) 1996-11-21
EP0825973A1 (fr) 1998-03-04
JPH11505235A (ja) 1999-05-18

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