AU592695B2 - A process for the removal of ethylene oxide and/or propylene oxide from surface-active derivatives - Google Patents

A process for the removal of ethylene oxide and/or propylene oxide from surface-active derivatives Download PDF

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Publication number
AU592695B2
AU592695B2 AU13209/88A AU1320988A AU592695B2 AU 592695 B2 AU592695 B2 AU 592695B2 AU 13209/88 A AU13209/88 A AU 13209/88A AU 1320988 A AU1320988 A AU 1320988A AU 592695 B2 AU592695 B2 AU 592695B2
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AU
Australia
Prior art keywords
steam
active derivatives
ethylene oxide
active
fatty
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Ceased
Application number
AU13209/88A
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AU1320988A (en
Inventor
Franz Buttgen
Klaus Dr. Friedrich
Klaus Herrmann
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Epoxy Compounds (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Manufacturing Of Printed Wiring (AREA)
  • Peptides Or Proteins (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

Abstract

1. A process for the removal of ethylene oxide and/or propylene oxide and, optionally, dioxane from surface-active derivatives - prepared by ethoxylation and/or propoxylation - of organic compounds containing at least one active hydrogen atom, characterized in that the surface-active derivatives are treated with steam, optionally in vacuo, at temperatures of 70 to 130 degrees C and the steam treated product is optionally dried.

Description

592695 S F Ref: 48198 FORM COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Class Int Class Complete Specification Lodged: Accepted: Published Priority: Related Art: Name and Address of Applicant: Address for Service: Henkel Kommanditgesellschaft auf Aktien Henkelstrasse 67 4000 Dusseldorf FEDERAL REPUBLIC OF GERMANY Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia Complete Specification for the invention entitled: A Process for the Removal of Ethylene Oxide and/or Propylene Oxide from Surface-Active Derivatives The following statement is a full description of this invention, including the best method of performing it known to me/us 5845/3
-III
D 7748
ABSTRACT
Ethylene oxide and/or propylene oxide and, optionally, dioxane may be removed from surface-active derivatives of organic compounds containing at least one active hydrogen t o J I atom obtained by thoxylation andor propoxylation to residual contents below the detection limit by treating the I surface-active derivatives with steam at temperatures of to 130 0 C, optionally in vacuo, and optionally drying the steam-treated product.
I 4- 4 e c i A.SS V r 1 1 Henkel KGaA TFP/Patente 21.12.1987 Dr. Gla/Pt Patent Application D 7844 A process for the removal of ethylene oxide and/or propylene lei# oxide from surface-active derivatives St I This invention relates to a process for the removal of ,ft( ethylene oxide and/or propylene oxide and, optionally, dioxane from surface-active derivatives of organic compounds containing at least one active hydrogen atom obtained by 5 ethoxylation and/or -propoxylation.
Surface-active derivatives of compounds containing at least one active hydrogen atom obtained by ethoxylation and/or propoxylation may contain traces of ethylene oxide and/or propylene oxide and of dioxane from their production.
According to a recommendation of the Bundesgesundheitsamtes (Federal Health Office), published in Bundesgesundheitsblatt 29, 21 to 22 (1986), the residual content of ethylene oxide in pharmaceutical base materials should be limited to less than 1 ppm.
US-PS 4,443,634 describes a process of the type mentioned at the beginning in which the surface-active derivatives to be purified are sprayed, optionally several times, into a chamber filled with an inert gas and the impurities to be eliminated are removed as vapors.
It has now been found that ethylene oxide and/or propylene oxide and, optionally, dioxane can be removed from the surface-active derivatives mentioned by a much simpler method providing the derivatives are subjected to a treat- 2 1 ment with steam.
Accordingly, the present invention relates to a process for the removal of ethylene oxide and/or propylene oxide and, optionally, dioxane from surface-active derivatives of organic compounds containing at least one active hydrogen atom obtained by ethoxylation and/or propoxylat\ion, characterized in that the surface-active derivatives are treated with steam at temperatures of 70 to 130°C, optionally in vacuo, and the steam-treated product is optionally dried.
The surface-active derivatives to be purified in accordance with the invention are known substances which may be obtained by conventional methods of organic synthesis.
They are all produced by the ethoxylation and/or propoxylation of organic compounds containing at least one active hydrogen atom, such as for example fatty acids, fatty acid amides, fatty alcohols, normal and hardened castor oils, glycerol mono- and diesters, alkylphenols, polyglycols, Sfatty amines, fatty acid alkanolamides and carbohydrate esters. Typical representatives of this class of compounds include, for example, an adduct of 9 moles ethylene oxide with coconut oil fatty acid, an adduct of 2 moles ethylene oxide with a mixture of C 12
-C
14 fatty alcohols, an adduct of 3 i moles ethylene oxide and 8 moles propylene oxide with a mixture of C 12
-C
18 fatty alcohols, an adduct of 41 moles ethylene oxide with castor oil, an adduct of 25 moles ethylene oxidq with hardened castor oil, an adduct of 7 parts by weight ethylene oxide with 10 parts by weight of a mixture of palmitit acid and stearic acid mono and diglycerides containing 40 to 45% by weight monoglyceride, an adduct of 30 10 moles ethylene oxide with nonylphenol, an adduct of 7.3 moles ethylene oxide with glycerol, an adduct of 10 moles ethylene oxide with a diol mixture obtained by reaction of a mixture of C 12 -C 6 1,2-epoxyalkanes with ethylene glycol, an adduct of 12 moles ethylene oxide with a mixture of Ci0-C18 fatty amines, an adduct of 4 moles ethylene oxide with coco- C- 3-CC -^i.-o^tenatt^.
3 1 nut fatty acid monoethanolamide and an addu"t of 20 moles ethylene oxide with sorbitan monostearate.
In one preferred embodiment of the invention, the surface-active derivatives are treated with steam at 100 to 130 0
C.
The purification of the surface-active derivatives in accordance with the invention is best carried out by blowing steam into the products heated to 70 to 130°C. It may be necessary to dry the purified substances after the treatment with steam. There are essentially two ways of doing this.
Where the treatment with steam is carried out with saturated steam at normal pressure, the product is dried in vacuo.
Where the treatment with steam is carried out under reduced pressure, the product is left standing under the vacuum applied on completion of the steam treatment until the desired water content has been reached.
In order to increase the efficiency of the steam treatment, the steam is introduced into the surface-active derivativea to be purified preferably in finely dispersed form, for example through nozzle heads. It is also preferred to carry out the steam treatment and, optionally, the drying step with stirring.
In another preferred embodiment of the invention, steam under a pressure of 4 bar is introduced into the surfaceactive derivatives to be purified in a quantity of at least kg per metric tonne of derivative per hour and preferably in a quantity of from 30 to 50 kg per metric tonne of derivative per hour.
In another advantageous embodiment of the invention, the surface-active derivatives are subjected tc a neutralizing treatment before the treatment with steam. This neutralizing treatment has a particularly favorable effect on f ethoxylated and/or prQpoxylated fatty acid alkanolamides because otherwise relatively heavily colored products would be obtained.
hi.
L 4 1 By means of the process according to the invention, ethylene oxide and/or propylene oxide and/or dioxane can each be removed from the surface-active derivatives to a residual content of 1 ppm and preferably of 0.1 ppm.
The invention is illustrated by the following preferred examples of embodiment.
EXAMPLE 1 A fatty alcohol alkoxylate prepared by reaction of a 10 mixture of C12 and C14 fatty alcohols (quantitative ratios C12 C14 70 30) with 2 moles ethylene oxide was purified as follows: 20,000 kg ethoxylate were introduced into a m 3 stirring vessel and heated to 110 0 C. After this temperature had been reached, steam under a pressure of 4 bar was fed to the alkoxylate through a distributor ring at the bottom of the vessel in a quantity of 40 kg per metric tonne of product per hour. The temperature rose to 120 130°C in this phase. Steam, ethylene oxide and dioxane were passed through a vapor tube to a heat exchanger surmounting the stirring vessel and condensed therein. The distillate was transferred to a collecting vessel. The distillation process was terminated after an empirically determined time of hours. The residual alkoxylate contained ethylene oxide and dioxane in quantities below the detection limit ppm).
S 25 The product was then dried to a residual moisture content of less than 0.3% by weight at a temperature of approximately with continued stirring and with simultaneous application of vacuum to approx. 100 mbar.
The distillate obtained was discarded after the destruction of ethylene oxide and purification.
EXAMPLE 2 An alkoxylate prepared by reaction of a C 16 -C18 fatty alcohol (50 50) with 20 moles ethylene oxide was treated as described in Example 1. After the treatment, the ethyl-
F>
r 1' c~ 5 1 ene oxide and dioxane contents were below the detection limit.
EXAMPLE 3 An .alkoxylate obtained from a C12/C14/C16 olefin epoxide, which had been reacted first with glycol and then with 1.2 moles propylene oxide and thereafter with 9 moles ethylene oxide, was treated as described in Example 1. The purified product contained ethylene oxide, propylene oxide 10 and dioxane in quantities below the detection limit.
t

Claims (7)

  1. 2. A process as claimed in claim 1, characterized in that surface-active derivatives of compounds from the group com- prising fatty acids, fatty acid amides, fatty alcohols, normal and hardened castor oils, glycerol mono- and diesters, i kylphenols, polyglycols, fatty amnines, fatty acid alkanol- amides and carbohydrate esters are treated with steam.
  2. 3. A process, as claimed in claim 2 or 3, characterized in that the surface-active derivatives are treated with steamn at 100 to 130 0 C.
  3. 4. A process as claimed in at least one of claims I to 3, characterized in that steam is introduced into the surface- active derivatives in finely divided form. A process as claimed in at least one of claims 1 to 4, characterized in that the treatment with steam is carried out with stirring.
  4. 6. A process as claimed in at least one of claims 1 to characterized in that at least 10 1,g steam under a pressure of 4 bar is introduced per tonne surface-active derivative per hour.
  5. 7. A process as claimed In at least one of claims I to 6, characterized in that from 30 to 50 kg steam under a, pressure of 4 bar is introduced per tonne surface-active derivative per hour.
  6. 8. A proocess as claimed in at least one of claims 1 to 7, characterized in that the surface-active derivatives, miore especially ethoxylatedl and/or propoxylated ratty acid I 7 alkanolamides, are neutralized before the treatment with steam.
  7. 9. A process as claimed in at leaFL one of claims 1 to 8, characterized in that ethylene oxide and/or propylene oxide and/or dioxane are each removed to a residual content of 1 ppm and more especially of 0.1 ppm. DATED this FIFTEENTH day of MARCH 1988 Henkel Kommanditgesellschaft auf Aktien Patent Attorneys for the Applicant SPRUSON FERGUSON i: I laoaie, aenurlze eoetetetetwt D 7748 RT/EN
AU13209/88A 1987-03-18 1988-03-17 A process for the removal of ethylene oxide and/or propylene oxide from surface-active derivatives Ceased AU592695B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19873708813 DE3708813A1 (en) 1987-03-18 1987-03-18 METHOD FOR REMOVING ETHYLENE AND / OR PROPYLENE OXIDE FROM SURFACE-ACTIVE DERIVATIVES
DE3708813 1987-03-18

Publications (2)

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AU1320988A AU1320988A (en) 1988-09-22
AU592695B2 true AU592695B2 (en) 1990-01-18

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AU13209/88A Ceased AU592695B2 (en) 1987-03-18 1988-03-17 A process for the removal of ethylene oxide and/or propylene oxide from surface-active derivatives

Country Status (13)

Country Link
EP (1) EP0283862B1 (en)
JP (1) JPS63252537A (en)
KR (1) KR880011051A (en)
AT (1) ATE57370T1 (en)
AU (1) AU592695B2 (en)
BR (1) BR8801215A (en)
DE (2) DE3708813A1 (en)
ES (1) ES2018585B3 (en)
GR (1) GR3001305T3 (en)
MX (1) MX170299B (en)
NO (1) NO168819C (en)
TR (1) TR24020A (en)
ZA (1) ZA881910B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3811319A1 (en) * 1988-04-02 1989-10-19 Henkel Kgaa ALCOHOL ETHOXYLATE WITH REDUCED REST EO CONTENT REST PO CONTENT
US5268510A (en) * 1992-10-08 1993-12-07 Vista Chemical Company Process for purification of alkoxylated alcohols
DE4312009C2 (en) * 1993-04-13 1995-06-08 Henkel Kgaa Process for the production of sugar surfactants with improved odor quality
DE4340093A1 (en) * 1993-11-24 1995-06-01 Cognis Bio Umwelt Process for the simplified separation of multi-component mixtures of at least a proportion of organic origin
DE4402883A1 (en) * 1994-02-01 1995-08-03 Henkel Kgaa Optimized process for the treatment of vapor-based vapor streams
EP1640401A3 (en) * 2004-09-24 2006-04-12 Clariant Produkte (Deutschland) GmbH Polyethylenglycol and alcoholethoxylates - Process for their preparation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2755089C3 (en) * 1977-12-10 1982-05-13 Bayer Ag, 5090 Leverkusen Process for cleaning raw polyethers
US4443634A (en) * 1983-03-29 1984-04-17 Conoco Inc. Removal of impurities

Also Published As

Publication number Publication date
DE3708813A1 (en) 1988-09-29
ATE57370T1 (en) 1990-10-15
MX170299B (en) 1993-08-16
AU1320988A (en) 1988-09-22
JPS63252537A (en) 1988-10-19
DE3860766D1 (en) 1990-11-15
BR8801215A (en) 1988-10-25
NO881184L (en) 1988-09-19
GR3001305T3 (en) 1992-08-31
KR880011051A (en) 1988-10-26
NO168819B (en) 1991-12-30
NO881184D0 (en) 1988-03-17
TR24020A (en) 1991-02-01
ZA881910B (en) 1989-08-30
EP0283862B1 (en) 1990-10-10
EP0283862A1 (en) 1988-09-28
ES2018585B3 (en) 1991-04-16
NO168819C (en) 1992-04-08

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