DE3609735A1 - Method for purifying tetraacetylethylene diamine - Google Patents

Method for purifying tetraacetylethylene diamine

Info

Publication number
DE3609735A1
DE3609735A1 DE19863609735 DE3609735A DE3609735A1 DE 3609735 A1 DE3609735 A1 DE 3609735A1 DE 19863609735 DE19863609735 DE 19863609735 DE 3609735 A DE3609735 A DE 3609735A DE 3609735 A1 DE3609735 A1 DE 3609735A1
Authority
DE
Germany
Prior art keywords
taed
method according
drying
acetic acid
wash
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
DE19863609735
Other languages
German (de)
Inventor
Klaus Dr Koester
Franz-Josef Dr Carduck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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
Family has litigation
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19863609735 priority Critical patent/DE3609735A1/en
Priority claimed from DE19873770666 external-priority patent/DE3770666D1/en
Publication of DE3609735A1 publication Critical patent/DE3609735A1/en
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6297039&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE3609735(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/32Amides; Substituted amides

Description

The compound N, N, N ', N'-tetraacetylethylenediamine, in the following referred to more simply as tetraacetylethylenediamine or TAED of recent practical importance as an activator in peroxide-containing Bleaching liquors and detergents obtained. Most important The manufacturing process is the acetylation of N, N'-diacetylethylenediamine (DAED) with the help of acetic anhydride. Of this Process by which TAED was first manufactured in 1911 numerous variants have become known (e.g. DE 21 33 458, DE 21 18 281, DE 30 24 694, GB 20 96 133, EP 4 919, EP 51 739 and EP 79 671).

The implementation of DAED with acetic anhydride, which is commonly used in Temperatures between 120 and 170 ° C with excess acetic anhydride performed, TAED delivers in an equilibrium reaction, so that the reaction mixtures next to the desired one End product of unreacted DAED and triacetylethylenediamine contain. Furthermore, dark colored ones are formed during the reaction By-products of unknown nature. Raw TAED like it from these reaction mixtures, for example by crystallization, is isolated, always contains a certain amount By-products and in this form can generally not be direct continue to be used as for most areas of application a product that is as pure, colorless and odorless as possible is required becomes. The TAED must therefore be manufactured with a Cleaning procedures are connected.  

Numerous suggestions have also been made for cleaning the TAED been made by a simple wash with acetic anhydride (DE 21 33 458, DE 21 18 281) on the use of adsorbents before crystallization (EP 4 919) up to fractional Distillation of the TAED (EP 8 369) are sufficient. Furthermore is have been proposed (EP 70 432), the crude TAED in a suspending agent disperse finely and after a longer period of time isolate again. However, none of these cleaning procedures is free of disadvantages, be it low effectiveness or product loss or else high energy and / or device expenditure.

The task was still simple and simple to develop effective cleaning procedures for TAED. In particular there was the task of such a cleaning process to develop a TAED in the for use in detergents suitable purity.

According to the invention, this object is achieved by a cleaning process, which is the raw, crystalline TAED first (a) wash with acetic acid, then (b) wash with water wash and finally (c) dry. Preferably too partial drying between the two washing steps performed. In particularly preferred process variants several successive substeps in the same Apparatus carried out and / or drying in one or two drying steps with the help of gases, preferably Air that is blown through the product.

The method according to the invention surprisingly allows without significant losses of valuable materials with extremely low Amounts of washing liquids a colorless and odorless Winning product. The need for time, energy and equipment is also minor, so the procedure despite the need of three or four individual steps a faster and  enables cheaper cleaning than other processes same effectiveness.

The cleaning method according to the invention is not specific Manufacturing process bound by the TAED. Especially it is advantageous, however, after such manufacturing processes, where acetic acid is part of the reaction mixture is applied, because then the first washing liquid worked up easily together with the mother liquors of the reaction and can be returned if necessary. Preferably the cleaning method according to the invention therefore closes to a manufacturing process in which TAED by acetylation is obtained by means of acetic anhydride.

The individual stages of the cleaning process according to the invention can be individually in separate equipment, as they are for Filtration, washing and drying processes are known will. However, preferably several, in particular all steps carried out in the same apparatus. examples for Devices in which both washing operations and drying single-layer filters, such as pressure filters, can be carried out and filter dryers, belt filters and drum filters.

Of these, the rotary pressure filters are preferred, which allow continuously in several successive Work segments not only all stages of the invention Cleaning process, but on which also the previous final step of the manufacturing process, filtering of the crystalline TAED.

The design of the individual stages of the cleaning process depends on the quality of the raw TAED as well according to the desired quality of the cleaned material. At  the process according to the invention can be described in both circumstances adapt wide limits.

The first wash (a) is preferably at temperatures between 17 and 30 ° C, but possibly also by use of warm TAED and / or warmed acetic acid elevated temperatures, but preferably not above 50 ° C. The amounts of acetic acid used, if any can also contain small amounts of water, are preferably at 0.2 to 2 l, in particular between 0.5 to 1.2 l per kg TAED (calculated as pure substance). The laundry can be slurried and moving the TAED in acetic acid be, but is preferably on the more or less immobile TAED filter cake made. The contact times from the addition of acetic acid to the end of filtering, or the flow times are between about 0.001 and 6, preferably between 0.01 and 2 seconds.

The drying step that follows the acetic acid wash in the preferred embodiment of the process is preferably carried out on the filter used for the previous step. If this drying can also be achieved in the usual way under vacuum, if necessary with heating, it has proven to be more advantageous to blow gases which are inert for drying, such as nitrogen or carbon dioxide, but preferably air, through the product under pressure. Moving the product during this process can be useful, but is not necessary. Gas quantities of 0.05 to 2 m 3 , preferably 0.1 to 1 m 3 per kg TAED are generally sufficient for the partial drying required according to the invention. The inlet temperatures of the gases are preferably 10 to 100 ° C, in particular between 15 and 70 ° C.

The second wash cycle (b) is carried out with water of preferably 5- 50 ° C, especially 10-30 ° C and can also  supported by slurrying and moving the TAED in the water will. However, the washing liquid is also preferred here passed through the still filter cake. The Amounts of wash water are preferably between 0.5 and 8 l, in particular between 1 and 5 l per kg TAED. You align yourself primarily, as well as the contact or flow times, preferably between about 0.001 and 6 seconds, in particular be between 0.01 and 2 seconds after the acetic acid content of the TAED.

The final drying step (c) is generally carried out in a manner similar to the drying step after washing with acetic acid. The conditions are chosen so that, in combination with the previous washing process, the acetic acid is removed as far as required, preferably until the product is odorless, and the water content of the material corresponds to the specified specification. This drying step is also preferably carried out with the aid of gases, in particular air, which are blown through the moist material at temperatures of preferably 10 to 100 ° C., in particular between 15 and 70 ° C. As in the first drying step, the amounts of gas required are preferably between 0.05 and 2 m 3 , in particular between 0.1 and 1 m 3, per kg of TAED.

The cleaning method according to the invention allows the resulting TAED directly for further use, especially in Add detergents, bleaches and disinfectants. Usually the finely crystalline TAED, however, to ensure storage stability increase in the presence of alkaline materials, first in an agglomeration process, for example according to DE 30 11 998 in a granulate transferred. The necessary in this process The amount of water can be controlled by appropriately guiding stages b and c of the cleaning method according to the invention already readily be given to the cleaned TAED.

example 1

In a stirred tank with a reflux condenser and bottom drain 360 kg of diacetylethylenediamine with 1275 kg of acetic anhydride for 3 hours heated to reflux temperature. The resulting brown solution was rapidly cooled to about 30 ° C. with stirring, TAED failed in crystalline form. The crystal suspension was adjusted to a Drained rotary filter with six segments on which continuously the following processes were carried out in succession (data referenced to 1 kg of TAED pure substance):

  • - extensive separation of the mother liquor,
  • - Wash the raw TAED with 0.8 l acetic acid (water content 0.6% by weight, temperature 25 ° C, pressure 0.8-1 bar) at a contact time of approx. 0.05 sec,
  • Blowing through 0.2 m 3 of air (temperature 20 ° C., pressure 1.5 bar), which was recycled via a liquid separator,
  • - Wash with 1.8 l water (temperature 15 ° C, pressure 1 bar) with a contact time of approx. 0.05 sec,
  • - blowing through 0.3 m 3 of air (temperature 20 ° C, pressure 1.8 bar),
  • - Mechanical discharge of the end product.

A total of 364 kg of a colorless and odorless TAED was obtained. The water content was 5.4% by weight, based on dry matter, which in turn had a TAED content of 99.4%. The so cleaned TAED was suitable for use in detergents and could easily be incorporated into a granulation process will. The loss of acetic acid with the wash water  were carried out were low (acetic acid content of the Wash water 4%).

Example 2

The procedure was the same as in Example 1, but was on intermediate drying after washing with acetic acid is dispensed with. Around To get an odorless product, the filter cake had to 5 l of water can be washed per kg of TAED. The loss of acetic acid, that were created by leaving the wash water three times as high as in Example 1. Otherwise, it was suitable the cleaned TAED is just as good for use in detergents like that obtained in Example 1.

Example 3

The execution of this example also corresponded to example 1, however, acetic anhydride was used instead of Acetic acid used as a washing liquid. Despite increasing the Amount of water in the following washing process to over 8 l per kg TAED the final product contained more than 1% acetic acid so it did not was suitable for use in detergents. To remove the The TAED had another, intense, acetic acid Be subjected to drying process.

Claims (10)

1. Process for the purification of crystalline N, N, N ', N'-tetraacetylethylenediamine (TAED), consisting of the following process steps:
  • a) Wash with acetic acid
  • b) Wash with water
  • c) drying.
2. The method according to claim 1, in which between the method steps a and b made a partial drying becomes.
3. The method according to any one of claims 1 or 2, in which one or both drying steps consist of passing gases through to blow the moist product.
4. The method according to claim 3, in which air is used as the gas becomes.
5. The method according to any one of claims 1 to 4, in which several successive steps in the same apparatus be performed.
6. The method according to claim 5, wherein all process steps be carried out continuously in a rotary pressure filter.
7. The method according to any one of claims 1 to 6, in which per kg TAED 0.2-2 l acetic acid used as washing liquid will.
8. The method according to any one of claims 1 to 7, in which per kg TAED 0.5-8 l water used as washing liquid will.  
9. The method according to any one of claims 1 to 8, in which 0.05 to 2 m 3 of air with an inlet temperature of 10 to 100 ° C are used for drying.
10. Use of one of the methods according to claims 1 to 9 cleaned TAED in washing, bleaching or Disinfectants.
DE19863609735 1986-03-22 1986-03-22 Method for purifying tetraacetylethylene diamine Withdrawn DE3609735A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19863609735 DE3609735A1 (en) 1986-03-22 1986-03-22 Method for purifying tetraacetylethylene diamine

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE19863609735 DE3609735A1 (en) 1986-03-22 1986-03-22 Method for purifying tetraacetylethylene diamine
EP87103737A EP0238958B1 (en) 1986-03-22 1987-03-14 Method for the purification of tetraacetylethylenediamine
ES87103737T ES2022182B3 (en) 1986-03-22 1987-03-14 Procedure for the purification of tetraacetiletilenodiamina.
DE19873770666 DE3770666D1 (en) 1986-03-22 1987-03-14 Method for purifying tetraacetylethylene diamine.
AT87103737T AT64410T (en) 1986-03-22 1987-03-14 Method for purifying tetraacetylethylene diamine.
IE73487A IE59879B1 (en) 1986-03-22 1987-03-20 Process for the purification of tetraacetylethylene diamine

Publications (1)

Publication Number Publication Date
DE3609735A1 true DE3609735A1 (en) 1987-09-24

Family

ID=6297039

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19863609735 Withdrawn DE3609735A1 (en) 1986-03-22 1986-03-22 Method for purifying tetraacetylethylene diamine

Country Status (5)

Country Link
EP (1) EP0238958B1 (en)
AT (1) AT64410T (en)
DE (1) DE3609735A1 (en)
ES (1) ES2022182B3 (en)
IE (1) IE59879B1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1245724B (en) * 1990-11-09 1994-10-14 Caffaro Spa Ind Chim TAED of the purification process
CN103121960B (en) * 2013-02-22 2015-04-01 浙江金科日化原料有限公司 Efficient recrystallization method of tetraacetylethylenediamine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051739A1 (en) * 1980-11-08 1982-05-19 BASF Aktiengesellschaft Process for the preparation of tetraacetylethylene diamine

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3824286A (en) 1970-07-07 1974-07-16 Lever Brothers Ltd Preparation of polyacetylalkylene diamines
DE2118281C3 (en) 1971-04-15 1974-11-21 Basf Ag, 6700 Ludwigshafen
ES479375A1 (en) 1978-04-14 1979-07-16 Hoechst Ag Improved process for the preparation of n, n, n ', n'-te traacetiletilendiamina.
DE2832021A1 (en) 1978-07-21 1980-01-31 Basf Ag Method for producing tetraacetylaethylenediamin
DE2906606A1 (en) * 1979-02-21 1980-09-04 Hoechst Ag Colourless tetra:acetyl-ethylene di:amine prepn. - by di:acetyl ethylene di:amine acetylation with acetic anhydride opt. with ketene addn.
DE3011998C2 (en) 1980-03-28 1982-06-16 Henkel Kgaa, 4000 Duesseldorf, De
DE3024694C2 (en) 1980-06-30 1991-03-07 Warwick International Ltd., Leeds, Gb
GB2096133B (en) 1981-04-03 1985-04-24 Croda Chemicals Ltd Production of tetraacetylethylene diamine
DE3127435A1 (en) 1981-07-11 1983-02-03 Bayer Ag Method for producing purified tetraacetylethylene diamine (taed)
EP0079671A3 (en) 1981-09-28 1984-03-21 Albright & Wilson Limited Process for preparing tetraacetyl alkylene diamines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051739A1 (en) * 1980-11-08 1982-05-19 BASF Aktiengesellschaft Process for the preparation of tetraacetylethylene diamine

Also Published As

Publication number Publication date
EP0238958A3 (en) 1988-08-17
AT64410T (en) 1991-06-15
EP0238958A2 (en) 1987-09-30
ES2022182B3 (en) 1991-12-01
EP0238958B1 (en) 1991-06-12
IE870734L (en) 1987-09-22
IE59879B1 (en) 1994-04-20

Similar Documents

Publication Publication Date Title
US4357475A (en) Process for the production and the recovery of terephthalic acid
CA2426745C (en) Methods for producing nateglinide b-type crystals
US3452088A (en) Terephthalic acid recovery
DE60110973T2 (en) Process for recovering crystals from a slurry
AU624392B2 (en) Imidoperoxycarboxylic acids, processes for their preparation and their use
EP0682554B2 (en) Filtration process
US5200557A (en) Process for preparation of crude terephthalic acid suitable for reduction to prepare purified terephthalic acid
EP0579716B1 (en) Process for preparation of terephthalic acid
US5527957A (en) Process for the production of terephthalic acid
US4219669A (en) Method of treating mother liquor of reaction in terephthalic acid production
US5004558A (en) Sulfone peroxycarboxylic acids
DE102004034316B4 (en) A process for the preparation of (meth) acrylic acid
JP4272704B2 (en) Process and apparatus for producing purified terephthalic acid
CA2307783C (en) Method and apparatus for preparing purified terephthalic acid
US7470370B2 (en) Process for removal of impurities from mother liquor in the synthesis of carboxylic acid using pressure filtration
EP1349826B1 (en) Continuous method for the production and purification of (meth)acrylic acid
US7339072B2 (en) Process for production of a carboxylic acid/diol mixture suitable for use in polyester production
EP2450342B1 (en) Process for production of a dried carboxylic acid cake suitable for use in polyester production
KR100210181B1 (en) Process for recovery of purified terephthalic acid
EP0818434B1 (en) Process for the production of high-purity isophthalic acid
EP1492755B1 (en) (meth)acrylic acid crystal and method for the production and purification of aqueous (meth)acrylic acid
KR101004217B1 (en) Process for the oxidative purification of terephthalic acid
US7074954B2 (en) Process for the oxidative purification of terephthalic acid
US4954621A (en) Process for producing sucrose fatty acid polyester
US2794832A (en) Crystallization and separation of crystals

Legal Events

Date Code Title Description
8110 Request for examination paragraph 44
8125 Change of the main classification

Ipc: C07C233/91

8130 Withdrawal