3,3′-methylenebis (5-methyloxazolidine)

Structural formula
General
Surname	3,3′-methylenebis (5-methyloxazolidine)
other names	3,3′-methylenebis (5-methyl-1,3-oxazolidine) ( IUPAC ) MBO Reaction product of paraformaldehyde and 2-hydroxypropylamine
Molecular formula	C 9 H 18 N 2 O 2
Brief description	yellowish liquid
External identifiers / databases
CAS number 66204-44-2 EC number 266-235-8 ECHA InfoCard 100.060.195 PubChem 128328 ChemSpider 113764 Wikidata Q27283280
properties
Molar mass	186.25 g mol −1
Physical state	liquid
density	1.049-1.069 g · cm −3 at 20 ° C
Melting point	<−35 ° C
boiling point	approx. 204 ° C
solubility	miscible with water and oil
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302 + 332-311-314-317-318-341-350-373 EUH: 071 P: 260-261-264-270-271-280-301 + 312-301 + 330 + 331-302 + 352-304 + 340-312-321-330-361 + 364-405-501
Toxicological data	630 mg kg −1 ( LD 50 ,  rat ,  oral ) 790 mg kg −1 ( LD 50 ,  rat ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,3'-methylenebis (5-methyloxazolidine) , MBO or "reaction product of paraformaldehyde and 2-hydroxypropylamine (ratio 3: 2)", is a so-called formaldehyde releaser and is used as a biocide for the preservation of liquids, such as. B. of water-based paints and cooling lubricants , and used as a hydrogen sulfide catcher in oil and gas treatment.

Occurrence and representation

The "reaction product of paraformaldehyde and 1-amino-2-propanol in the ratio 3: 2" is a so-called UVCB ( U Nknown or V ariable composition, C omplex reaction products or B iological materials) and formed in the reaction of formaldehyde HCHO or paraformaldehyde (HCHO) _{n in} addition to α, α ′, α ′ ′ - trimethyl-1,3,5-triazine-1,3,5 (2 H , 4 H , 6 H ) -triethanol (HPT), which at a formaldehyde: aminopropanol ratio 1: 1 becomes the main product.

The reaction is exothermic and is kept at 80.degree. After the water formed has been distilled off, the product is purified by vacuum distillation .

properties

3,3′-methylenebis (5-methyloxazolidine) is a yellowish liquid with an amine-like odor, the aqueous solutions of which (1.5 gcm ⁻³ ) are alkaline (pH 10 at 20 ° C). The compound is stable at elevated temperatures (up to 186 ° C) and over a wide pH range. In aqueous solution, MBO slowly breaks down into its starting materials 1-aminopropan-2-ol and formaldehyde (45% of which can be released). MBO has a strong bactericidal and fungicidal effect and inhibits the growth of yeast and algae . It has anti-corrosive properties and removes hydrogen sulfide H ₂ S from process streams.

Applications

3,3'-methylenebis (5-methyloxazolidine) is a broadly effective and long-term active formaldehyde releaser and is used as a biocide for the preservation of water-based paints, cooling lubricant emulsions, oils, and lubricants and fuels, such as. B. Diesel (and biodiesel) are used. MBO is used as a biocide and as a hydrogen sulfide scavenger in oil and gas exploration and processing.

Risk assessment

3,3'-methylenebis (5-methyloxazolidine) (oxazolidine / MBO) [reaction product of paraformaldehyde and 2-hydroxypropylamine (ratio 3: 2)] is because of the release of formaldehyde from MBO and the by-product HPT, according to the expert opinion of the European Chemicals Agency ECHA potential candidate for substitution . The reaction product is currently subject to a comprehensive assessment with regard to its further use in the product types PT 2 (disinfection), PT 6 ( pot preservative ), PT 11 (coolant), PT 12 slime control) and PT 13 (cooling lubricant). In 2015, an assessment was carried out according to the H sentence H 350 (can cause cancer) or Carc. 1B (probably carcinogenic in humans ), which is included in the safety information of some databases, e.g. B. GESTIS is not yet taken into account.

Manufacturer and trade name

3,3'-methylenebis (5-methyloxazolidine) or the reaction product of paraformaldehyde and 2-hydroxypropylamine (ratio 3: 2) is sold by Lubrizol under the brand name Contram ^® MBO, by Vink Chemicals under the name Vinkocide ^® MBO (formerly from Schülke & Mayr as Grotan ^® OX on the market) and from Troy Corp. manufactured and marketed under the Bakzid ^® trademark .

Individual evidence

1. ↑ ^{a b c d e f g} Entry on N, N'-methylenebis (5-methyloxazolidine) in the GESTIS substance database of the IFA , accessed on March 22, 2020 (JavaScript required)
2. ↑ ^{a b c d e f} Registration dossier on 3,3'-methylenebis [5-methyloxazolidine] ( GHS section ) at the European Chemicals Agency (ECHA), accessed on March 22, 2020.
3. ↑ Patent US4166122 : Bis- (5,5-dimethyl-1,3-oxazolidin-3-yl) methane as an antimicrobial agent. Applied on February 21, 1978 , published on August 28, 1979 , applicant: Bayer AG, inventor: W. Paulus, H. Genth. ‌
4. ↑ Patent WO2017102693A1 : Use of compositions having a content of 3,3'-methylenebis (5-methyloxazolidine) in the removal of sulfur compounds from process streams. Registered on December 13, 2016 , published on June 22, 2017 , applicant: Schülke & Mayr GmbH, inventors: W. Bleifuss, R. Gradtke, S. Hahn, J. Knopf, M. Streek, J. Thiede, K. Weber . ‌
5. ↑ A. Turkiewicz, J. Brzeszcz, P. Kapusta: The application of biocides in the oil and gas industry . In: Nafta-Gaz . tape 2 , 2013, p. 103-111 ( PDF ).