66204-44-2

Basic information

• Product Name: 3,3'-methylenebis[5-methyloxazolidine]
• Synonyms: 3,3'-methylenebis[5-methyloxazolidine];Methylen-bis(methyloxazolidin);N,N'-Methylen-bis(5-methyloxazolidin);Oxazolidine, 3,3-methylenebis5-methyl-;grotan OX;METHYLENE-BIS-(METHYLOXAZOLIDINE);GROTANOX(R);3,3′-Methylenbis(5-methyloxazolidin)
• CAS NO: 66204-44-2
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25142
• EINECS: 266-235-8
• Mol File: 66204-44-2.mol

Chemical Properties

• Boiling Point: 247.6°Cat760mmHg
• Flash Point: 70.1°C
• Appearance: /
• Density: 1.062g/cm³
• Vapor Pressure: 1.4Pa at 25℃
• PKA: 5.06±0.40(Predicted)
• CAS DataBase Reference: 3,3'-methylenebis[5-methyloxazolidine](CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-methylenebis[5-methyloxazolidine](66204-44-2)
• EPA Substance Registry System: 3,3'-methylenebis[5-methyloxazolidine](66204-44-2)

Safety Data

• Hazardous Substances Data: 66204-44-2(Hazardous Substances Data)

Usage

Uses

Used in Adhesives:
3,3'-methylenebis[5-methyloxazolidine] is used as a cross-linking agent in adhesives for improving the mechanical strength and chemical resistance of the adhesive bonds, ensuring robust and durable connections between materials.
Used in Coatings:
In the coatings industry, 3,3'-methylenebis[5-methyloxazolidine] serves as a curing agent for epoxy resins, facilitating the formation of a strong and durable polymer network. This enhances the overall performance and longevity of the coatings, providing protection and aesthetic appeal to various surfaces.
Used in Elastomers:
3,3'-methylenebis[5-methyloxazolidine] is utilized as a cross-linking agent in elastomers to improve their mechanical properties, such as tensile strength and elasticity. This makes the elastomers more resistant to wear and tear, extending their service life in various applications.
Used as a Chemical Intermediate:
3,3'-methylenebis[5-methyloxazolidine] also functions as a chemical intermediate in the synthesis of other compounds, contributing to the development of new materials and products across different industries.
It is important to handle 3,3'-methylenebis[5-methyloxazolidine] with care, as it is a skin and respiratory irritant and may pose health risks if not properly managed.

Synthetic route

formaldehyd (50-00-0) + 3-amino-2-propanol (78-96-6, 1674-56-2) → 3,3'-methylenebis-[5-methyloxazoldiine] (66204-44-2) + 6,9-dimethyl-3,8-dioxa-1,6-diazabicyclo[4.4.1]undecane

Conditions	Yield
In tetrahydrofuran at -78℃; for 4h;	A 72% B n/a
In benzene for 6h; Dean-Stark; Reflux; Overall yield = 53 %; Overall yield = 4.9 g;

2-Amino-1-propanol (6168-72-5) + paraformaldehyde → 3,3'-methylenebis-[5-methyloxazoldiine] (66204-44-2)

Conditions	Yield
Stage #1: 2-Amino-1-propanol; paraformaldehyde Cooling with water-bath; 1/3 part of formaldehyde was added; Stage #2: paraformaldehyde at 65℃; Second 1/3 part of formaldehyde was added; Stage #3: paraformaldehyde at 140℃; third part of formaldehyde was added at 65 °ree;C; Heating up to 95 °ree;C until disoslution of formaldehyde; Heating / reflux;

formaldehyd (50-00-0) + 3-amino-2-propanol (78-96-6, 1674-56-2) → 3,3'-methylenebis-[5-methyloxazoldiine] (66204-44-2)

Conditions	Yield
In toluene Dean-Stark; Reflux;

Upstream product

• 50-00-0 formaldehyd 
• 78-96-6 3-amino-2-propanol 
• 6168-72-5 2-Amino-1-propanol 

Relevant articles and documents

COMPOSITIONS OF HETEROCYCLIC COMPOUNDS AND USES AS SULFIDOGENESIS INHIBITORS

The present disclosure generally relates to compositions and uses of sulfidogenesis inhibitor compounds of Formulae 1 and 2 for preventing sulfidogenesis, i.e., the reduction reaction of a sulfur-containing compound by sulfur-utilizing prokaryotes that produce sulfide species such as hydrogen sulfide, during enhanced oil recovery processes. A method for inhibiting or decreasing microbial sulfide production by sulfur-utilizing prokaryotes includes addition of an effective amount of sulfidogenesis inhibitor compounds of Formulae 1 and 2 to the fluid that is injected into a sulfidogenic reservoir system during enhanced oil recovery. For example, the compounds can be used as sulfidogenesis inhibitors in a water injection system for use in a hydrocarbon extraction system or a hydrocarbon production system. Thus, these compositions can be effectively used as inhibitors of biogenic hydrogen sulfide generation in oilfield fluids.

USE OF COMPOSITIONS HAVING A CONTENT OF 3,3'-METHYLENEBIS(5-METHYLOXAZOLIDINE) IN THE REMOVAL OF SULPHUR COMPOUNDS FROM PROCESS STREAMS

The invention relates to the use of a composition comprising a) 3,3′-methylenebis(5-methyl oxazolidine) and b) one or more additives selected from among (i) urea, urea derivatives, amino acids, guanidine and guanidine derivatives and (ii) 1,2-diols in the removal of sulphur compounds from process streams. The composition is preferably used in the removal of hydrogen sulphide from process streams.

Synthesis of 3-(alk-2-yn-1-yl)-1,3-oxazolidines using copper-containing catalysts

A selective method for the synthesis of 3-(alk-2-yn-1-yl)-1,3-oxazolidines has been developed by the reaction of bis(oxazolidin-3-yl)methanes with terminal acetylenes with copper-containing catalysts. The reaction of terminal acetylenes with optically active bis((4R)-4-ethyl-1,3-oxazolidin-yl)methane led to the formation of (4R)-3-(2-alkynyl)-4-ethyl-1,3-oxazolidines.

Equilibrium between bis(1,3-oxazolidin-3-YL])methanes and 3,8-dioxa1,6-diazabicyclo[4.4.1]Undecanes

The equilibrium between bis(1,3-oxazolidin-3-yl])methanes (A) and 3,8-dioxa-1,6-diazabicyclo[4.4.1]undecanes (B) is reported. A and B were prepared from formaldehyde and (±)-1-methylethanolamine (1), 2,2-dimethylethanolamine (2), (1S, 2R)-1-methyl-2-phenylethanolamine (3), ethanolamine (4), (R)-2-carboxyethanolamine methyl ester (5), (S)-2-ethylethanolamine (6), (R)-2phenylethanolamine (7). The equilibrium depends on the substituents. Thermodynamic structures (A) derived from 5 and 7 by slow crystallization are completely transformed into undecanes (B) by an equilibrium asymmetric transformation. Structures were established by 1H, COSY, HETCOR and NOESY NMR experiments. Preferred conformer of the undecane ring was identified.

Method of making reduced water content bisoxazolidine hydrogen sulfide scavengers

A method making sulfhydryl scavenging agents with reduced water content comprising treating the sulfhydryl scavenging agent to remove water. The sulfyhydryl scavenging agent preferably comprises an —N—C—N— moiety produced by condensation of an alkanolamine with an aldehyde. Preferred sulfhydryl scavenging agents are bisoxazolidines.

Bis-(5,5-dimethyl-1,3-oxazolidin-3-yl) methane as an antimicrobial agent

5,5'-DIMETHYL-DI-(1,3-OXAZOLIDIN-3-YL) METHANE, A PROCESS FOR ITS PREPARATION OF REACTING A SOURCE OF FORMALDEHYDE WITH ISOPROPANOLAMINE AT ELEVATED TEMPERATURE FOLLOWED BY WATER REMOVAL, AN ANTI-MICROBIAL COMPOSITION COMPRISING SAID 5,5'-DIMETHYL-DI-(1,3-OXAZOLIDIN-3-YL) METHANE AND A DILUENT AND A PROCESS FOR COMBATTING MICRO-ORGANISMS BY APPLYING 5,5'-DIMETHYL-DI-(1,3-OXAZOLIDIN-3-YL) METHANE TO A MICRO-ORGANISM CONTAINING SAMPLE.

Preserving and disinfecting method employing certain bis-oxazolidines

A method for preventing or retarding the growth of bacteria and fungi in a material which comprises treating the material with N,N'-methylene-bis-(oxazolidines) and -(tetrahydro-1,3-oxazines), and certain novel N,N'-methylenebis-(oxazolidines).