Triaminocaproic acid triazine
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| Surname | Triaminocaproic acid triazine | ||||||||||||||||||
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| Molecular formula | C 21 H 36 N 6 O 6 | ||||||||||||||||||
| Brief description |
white to pale beige crystalline solid |
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| Molar mass | 468.55 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| density |
1.28 g cm −3 |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
2,4,6-Tri (6-aminocaproic acid) -1,3,5-triazine (TACT) is a tricarboxylic acid that is produced by reacting ε-aminocaproic acid with cyanuric chloride and is used as a corrosion protection agent in aqueous systems and as a trifunctional building block for branched and Star-shaped ( dendrimers ) polyamides are used.
presentation
Looking for new pesticides 1963 Triaminocapronsäuretriazin of ε-aminocaproic acid, was established in caustic soda and cyanuric chloride shown and described for the first time.
An inexpensive source of ε-aminocaproic acid is ε-caprolactam , which is converted into the readily water-soluble sodium 6-aminohexanoate by basic hydrolysis with sodium hydroxide by boiling under reflux for one hour.
Cyanuric chloride has three chlorine atoms with different reactivity towards nucleophiles , which must be taken into account when carrying out the reaction as well as the tendency of cyanuric chloride to hydrolyze in aqueous media, especially in an alkaline environment.
Therefore, the three reaction components are first allowed to react for two hours at 0 to 5 ° C., then kept at 50 ° C. for three hours and then heated to the boil for a further 30 minutes. The TACT formed in 76% yield is precipitated by acidification. Approx. 20% of the so-called ammelidinedihexanoic acid is obtained, the disubstitution product of cyanuric chloride in which the third chlorine atom has been exchanged for a hydroxyl group by hydrolysis in an alkaline environment.
In other patents, cyanuric chloride suspended in water is presented and an aqueous-alkaline solution of the sodium salt of 6-aminohexanoic acid is added.
According to the Degussa process, an alkaline ε-aminocaproic acid solution is added to the cyanuric chloride suspension, which TACT precipitates at 90 ° C. and is filtered off while still hot. The product yield is 97.4% and the residual ammelidinedihexanoic acid content is only 0.5%. The mother liquor containing aminocaproic acid is fed back into the process.
The TACT synthesis from wastewater containing caprolactam is described in detail as a technically feasible route.
properties
2,4,6-Tri (6-aminocaproic acid) -1,3,5-triazine is a white to light beige, odorless crystalline solid which is hardly soluble in water at neutral pH and very readily soluble in alkaline pH. TACT has a low water hazard potential.
use
Triaminocaproic acid triazine is a so-called ash-free and low-foaming inhibitor for the corrosion of iron and iron alloys in aqueous systems and is mostly used as a potassium or triethanolamine salt in concentrations of 0.25 to 1.1% active ingredient content. Compared to triaminoalkanoic acid triazines with shorter alkyl chains, TACT shows the highest anticorrosive activity. The anti-corrosive effect comes about through adsorption of the TACT molecules with their carboxylate functions on the metal surface, with longer alkyl chains leading to thicker and denser protective layers.
Triaminocaproic triazine is a highly effective corrosion inhibitor even in hard water and in multi-metal systems. By adding TACT or its alkali metal or triethanolamine salts, water-containing coolants and antifreezes , hydraulic fluids , metal working fluids and cooling lubricants such as drilling and cutting emulsions (English metal working fluids ), as well as cooling water circuits and aqueous paints can be given an effective anti-corrosive effect.
Triaminocaproic acid triazine was also used as a comonomer, together with ε-aminocaproic acid, with the main monomer ε-caprolactam for the production of branched polyamide fibers which, despite the lack of amino end groups, are characterized by a high affinity for acidic dyes. Despite the branches in the polymer chain, the copolymers can be spun well and the fibers obtained have the same melt viscosity as the starting polymer, which indicates the high thermal stability of the copolyamide.
With TACT as the core, three-armed star-shaped polymers with high thermal stability can also be produced by copolymerization with ε-caprolactam, which show the same properties as a corresponding linear copolyamide even after significantly shorter polymerization times.
Because of the lower hydrodynamic radius typical of star polymers than linear polymers of the same composition and molar mass, the copolyamides obtained have significantly lower melt and solution viscosities, so that - at least theoretically - thinner-walled shapes and structures by z. B. injection molding should be achievable.
Individual evidence
- ↑ a b c Safety Data Sheet, Irgacor® L 190, BASF SE ( page no longer available , search in web archives: online ).
- ↑ Safety Data Sheet, BELCOR 593 , BWA Water Additives US LLC.
- ↑ a b Patent US4402907 : Triazine carboxylic acids as corrosion inhibitors for aqueous systems. Applied on August 3, 1981 , published September 6, 1983 , applicant: Ciba-Geigy Corp., inventor: DR Clark.
- ↑ Patent CN101973949 : 2,4,6- 三 (氨基 己 酸 基) -1,3,5- 三 嗪 的 制备 方法. Registered on November 17, 2010 , published on February 16, 2011 , applicant: 天津 师范大学, inventor: 刘巨艳, 刘海旺, 曹 改 娥, 王广辉, 王敬凤 (English title: Method for preparing 2,4,6-tri (amino caproyl) -1,3,5-triazine ).
- ↑ a b c Patent US6060580 : Star-shaped branched polyamide. Applied on November 3, 1997 , published on May 9, 2000 , applicant: DSM NV, inventors: AJ Nijenhuis, M. Serné, EMM de Brabander-van den Berg, R. Aberson.
- ↑ a b Entry on triazinetriyltriiminotrihexanoic acid in the GESTIS substance database of the IFA , accessed on November 5, 2015 (JavaScript required)
- ↑ a b A. Lübbert, J. Hegmann: Improvement of the wastewater situation in the production of caprolactam disulfide - final report on the funding program "operational environmental technology" of the Ministry for the Environment, Nature Conservation and Transport Baden Württemberg ( Memento from November 20, 2015 in the Internet Archive ). Rhein Chemie Rheinau GmbH, January 2009.
- ↑ Hans Nestler, Hans Fürst : On the representation of N (s-triazinyl) -amino-acid derivatives . In: J. Prakt. Chem. Volume 22 , no. 3-4 , 1963, pp. 173-185 , doi : 10.1002 / prac.19630220306 ( PDF ).
- ↑ a b Patent DE10208591 : Process for the crystallization of 6,6 ', 6' '- melamine trisalkanoic acids. Registered on February 27, 2002 , published on November 20, 2003 , applicant: Degussa AG, inventor: P. Werle, M. Trageser, H.-P. Krimmer.
- ↑ a b Metall-Chemie, product data sheet TC® 50 .
- ↑ S.-H. Yoo, Y.-W. Kim, J. Shin, N.-K. Kim, J.-S. Kim: Effects of the Chain Length of Tris (carboxyalkylamino) triazine on Corrosion Inhibition Properties . In: Bull. Korean Chem. Soc. tape 36 , 2015, p. 346-355 , doi : 10.1002 / bkcs.10090 .
- ↑ Patent US6074749 : Acid dyeable fiber. Applied on December 4, 1998 , published on June 13, 2000 , applicant: DSM NV, inventors: JEF Arnauts, AJ Nijenhuis, C. Versluis, R. Aberson.