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
• Article Data: 7

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

General Description

3,3'-methylenebis[5-methyloxazolidine] is a chemical compound known for its use as a cross-linking agent in various applications, including adhesives, coatings, and elastomers. It is a cyclic, organic compound containing two oxazolidine rings connected by a methylene bridge. The chemical is often utilized as a curing agent for epoxy resins, where it facilitates the formation of strong and durable cross-links in the polymer network. It is also used as a chemical intermediate in the synthesis of other compounds. Due to its cross-linking properties, 3,3'-methylenebis[5-methyloxazolidine] is valued for its ability to improve the mechanical strength and chemical resistance of materials, making it a versatile and important chemical in various industrial processes. Although it provides numerous benefits, the compound should be handled and used with caution, as it is considered 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

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

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.

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.