Triethylene glycol

Last updated
Triethylene glycol
Triethylene glycol.png
Names
Preferred IUPAC name
2,2′-[Ethane-1,2-diylbis(oxy)]di(ethan-1-ol)
Other names
2-[2-(2-Hydroxyethoxy)ethoxy]ethanol
Triglycol
Identifiers
3D model (JSmol)
AbbreviationsTEG
969357
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.594 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-953-2
260942
PubChem CID
RTECS number
  • YE4550000
UNII
  • InChI=1S/C6H14O4/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2 X mark.svgN
    Key: ZIBGPFATKBEMQZ-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C6H14O4/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2
    Key: ZIBGPFATKBEMQZ-UHFFFAOYAS
  • OCCOCCOCCO
Properties
C6H14O4
Molar mass 150.174 g·mol−1
AppearanceColorless liquid
Density 1.1255 g/mL
Melting point −7 °C (19 °F; 266 K)
Boiling point 285 °C (545 °F; 558 K)
Hazards
NFPA 704 (fire diamond)
1
1
0
Related compounds
Related diols
Ethylene glycol, Diethylene glycol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Triethylene glycol, TEG, or triglycol is a colorless odorless viscous liquid with molecular formula HOCH2CH2OCH2CH2OCH2CH2OH. It is used as a plasticizer for vinyl polymers. It is also used in air sanitizer products, such as "Oust" [1] or "Clean and Pure". When aerosolized it acts as a disinfectant. Glycols are also used as liquid desiccants for natural gas and in air conditioning systems. It is an additive for hydraulic fluids and brake fluids and is used as a base for "smoke machine" fluid in the entertainment industry.

Contents

Properties

Triethylene glycol is a member of a homologous series of dihydroxy alcohols. It is a colorless, odorless and stable liquid with high viscosity and a high boiling point. Apart from its use as a raw material in the manufacture and synthesis of other products, TEG is known for its hygroscopic quality and its ability to dehumidify fluids. This liquid is miscible with water, and at standard atmospheric pressure (101.325 kPa) has a boiling point of 286.5 °C and a freezing point of 7 °C. It is also soluble in ethanol, acetone, acetic acid, glycerine, pyridine, aldehydes; slightly soluble in diethyl ether; and insoluble in oil, fat and most hydrocarbons.

Preparation

TEG is prepared commercially as a co-product of the oxidation of ethylene at high temperature in the presence of silver oxide catalyst, followed by hydration of ethylene oxide to yield mono(one)-, di(two)-, tri(three)- and tetraethylene glycols.

Applications

TEG is used by the oil and gas industry to "dehydrate" natural gas. It may also be used to dehydrate other gases, including CO2, H2S, and other oxygenated gases. [2] It is necessary to dry natural gas to a certain point, as humidity in natural gas can cause pipelines to freeze, and create other problems for end users of the natural gas. Triethylene glycol is placed into contact with natural gas, and strips the water out of the gas. Triethylene glycol is heated to a high temperature and put through a condensing system, which removes the water as waste and reclaims the TEG for continuous reuse within the system. The waste TEG produced by this process has been found to contain enough benzene to be classified as hazardous waste [3] (benzene concentration greater than 0.5 mg/L).

Triethylene glycol is well established as a relatively mild disinfectant toward a variety of bacteria, influenza A viruses and spores of Penicillium notatum fungi. [4] However, its exceptionally low toxicity, broad materials compatibility, and low odor combined with its antimicrobial properties indicates that it approaches the ideal for air disinfection purposes in occupied spaces. [4] Much of the scientific work with triethylene glycol was done in the 1940s and 1950s, however that work has ably demonstrated the antimicrobial activity against airborne, solution suspension, and surface bound microbes. The ability of triethylene glycol to inactivate Streptococcus pneumoniae (original citation: pneumococcus Type I), Streptococcus pyogenes (original citation: Beta hemolytic streptococcus group A) and Influenza A virus in the air was first reported in 1943. [5] Since the first report the following microorganisms have been reported in the literature to be inactivated in the air: Penicillium notatum spores, [6] Chlamydophila psittaci (original citation: meningopneumonitis virus strain Cal 10 and psittacosis virus strain 6BC), [7] Group C streptococcus, [8] type 1 pneumococcus, [8] Staphylococcus albus , [8] Escherichia coli , [9] and Serratia marcescens Bizio (ATCC 274). [10] Solutions of triethylene glycol are known to be antimicrobial toward suspensions of Penicillium notatum spores, [6] Streptococcus pyogenes (original citation: Beta hemolytic streptococcus Group A ), [11] Streptococcus pneumoniae (original citation: pneumococcus Type I), [11] Streptococcus viridans , [11] and Mycobacterium bovis (original citation: tubercle bacilli Ravenel bovine-type). [12] Further, the inactivation of H1N1 influenza A virus on surfaces has been demonstrated. [13] The latter investigation suggests that triethylene glycol may prove to be a potent weapon against future influenza epidemics and pandemics. However, at least some viruses, including Pseudomonas phage phi6 become more infectious when treated with triethylene glycol. [14]

Safety

According to the European Chemicals Agency (ECHA), no hazards have been classified https://echa.europa.eu/es/substance-information/-/substanceinfo/100.003.594

Related Research Articles

<span class="mw-page-title-main">Vapor</span> Substances in the gas phase at a temperature lower than its critical point

In physics, a vapor or vapour is a substance in the gas phase at a temperature lower than its critical temperature, which means that the vapor can be condensed to a liquid by increasing the pressure on it without reducing the temperature of the vapor. A vapor is different from an aerosol. An aerosol is a suspension of tiny particles of liquid, solid, or both within a gas.

<span class="mw-page-title-main">Boiling</span> Rapid phase transition from liquid to gas or vapor

Boiling is the rapid phase transition from liquid to gas or vapor; the reverse of boiling is condensation. Boiling occurs when a liquid is heated to its boiling point, when the temperature at which the vapour pressure of the liquid is equal to the pressure exerted on the liquid by the surrounding atmosphere. Boiling and evaporation are the two main forms of liquid vaporization.

<span class="mw-page-title-main">Ethylene glycol</span> Organic compound ethane-1,2-diol

Ethylene glycol is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. Ethylene glycol has a sweet taste, but it is toxic in high concentrations.

<span class="mw-page-title-main">Disinfectant</span> Antimicrobial agent that inactivates or destroys microbes

A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than sterilization, which is an extreme physical or chemical process that kills all types of life. Disinfectants are generally distinguished from other antimicrobial agents such as antibiotics, which destroy microorganisms within the body, and antiseptics, which destroy microorganisms on living tissue. Disinfectants are also different from biocides—the latter are intended to destroy all forms of life, not just microorganisms. Disinfectants work by destroying the cell wall of microbes or interfering with their metabolism. It is also a form of decontamination, and can be defined as the process whereby physical or chemical methods are used to reduce the amount of pathogenic microorganisms on a surface.

An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals are used against fungi. They can also be classified according to their function. The use of antimicrobial medicines to treat infection is known as antimicrobial chemotherapy, while the use of antimicrobial medicines to prevent infection is known as antimicrobial prophylaxis.

Pneumococcal pneumonia is a type of bacterial pneumonia that is caused by Streptococcus pneumoniae (pneumococcus). It is the most common bacterial pneumonia found in adults, the most common type of community-acquired pneumonia, and one of the common types of pneumococcal infection. The estimated number of Americans with pneumococcal pneumonia is 900,000 annually, with almost 400,000 cases hospitalized and fatalities accounting for 5-7% of these cases.

Infection prevention and control is the discipline concerned with preventing healthcare-associated infections; a practical rather than academic sub-discipline of epidemiology. In Northern Europe, infection prevention and control is expanded from healthcare into a component in public health, known as "infection protection". It is an essential part of the infrastructure of health care. Infection control and hospital epidemiology are akin to public health practice, practiced within the confines of a particular health-care delivery system rather than directed at society as a whole.

<span class="mw-page-title-main">Hand sanitizer</span> Alternative to hand washing

Hand sanitizer is a liquid, gel or foam generally used to kill many viruses/bacteria/microorganisms on the hands. In most settings, hand washing with soap and water is generally preferred. Hand sanitizer is less effective at killing certain kinds of germs, such as norovirus and Clostridium difficile, and unlike hand washing, it cannot physically remove harmful chemicals. People may incorrectly wipe off hand sanitizer before it has dried, and some are less effective because their alcohol concentrations are too low.

Monochloramine, often called chloramine, is the chemical compound with the formula NH2Cl. Together with dichloramine (NHCl2) and nitrogen trichloride (NCl3), it is one of the three chloramines of ammonia. It is a colorless liquid at its melting point of −66 °C (−87 °F), but it is usually handled as a dilute aqueous solution, in which form it is sometimes used as a disinfectant. Chloramine is too unstable to have its boiling point measured.

<span class="mw-page-title-main">Lysol</span> Cleaning products brand name

Lysol is a brand of American cleaning and disinfecting products distributed by Reckitt, which markets the similar Dettol or Sagrotan in other markets. The line includes liquid solutions for hard and soft surfaces, air treatment, and hand washing. The active ingredient in many Lysol products is benzalkonium chloride, but the active ingredient in the Lysol "Power and Free" line is hydrogen peroxide. Lysol has been used since its invention in the late 19th century as a household and industrial cleaning agent, and previously as a medical disinfectant.

An oil production plant is a facility which processes production fluids from oil wells in order to separate out key components and prepare them for export. Typical oil well production fluids are a mixture of oil, gas and produced water. An oil production plant is distinct from an oil depot, which does not have processing facilities.

<span class="mw-page-title-main">Polyaminopropyl biguanide</span> Chemical compound

Polyaminopropyl biguanide (PAPB) is a disinfectant and a preservative used for disinfection on skin and in cleaning solutions for contact lenses. It is also an ingredient in many deodorant bodysprays. It is a polymer or oligomer where biguanide functional groups are connected by propyl hydrocarbon chains. PAPB is specifically bactericidal at very low concentrations (10 mg/L) and is also fungicidal.

A virucide is any physical or chemical agent that deactivates or destroys viruses. The substances are not only virucidal but can be also bactericidal, fungicidal, sporicidal or tuberculocidal.

Vaporized hydrogen peroxide (trademarked VHP, also known as hydrogen peroxide vapor, HPV) is a vapor form of hydrogen peroxide (H2O2) with applications as a low-temperature antimicrobial vapor used to decontaminate enclosed and sealed areas such as laboratory workstations, isolation and pass-through rooms, and even aircraft interiors.

<span class="mw-page-title-main">Airborne transmission</span> Disease transmission by airborne particles

Airborne transmission or aerosol transmission is transmission of an infectious disease through small particles suspended in the air. Infectious diseases capable of airborne transmission include many of considerable importance both in human and veterinary medicine. The relevant infectious agent may be viruses, bacteria, or fungi, and they may be spread through breathing, talking, coughing, sneezing, raising of dust, spraying of liquids, flushing toilets, or any activities which generate aerosol particles or droplets. This is the transmission of diseases via transmission of an infectious agent, and does not include diseases caused by air pollution.

An air sanitizer is a sanitizer that acts on airborne microbiological organisms or microorganisms. In the United States, a sanitizer is a disinfectant that is intended to disinfect or sanitize, reducing or mitigating growth or development of microbiological organisms including bacteria, fungi or viruses on inanimate surfaces in the household, institutional, and/or commercial environment and whose labeled directions for use result in the product being discharged to publicly owned treatment works (POTWS).

Copper and its alloys are natural antimicrobial materials. Ancient civilizations exploited the antimicrobial properties of copper long before the concept of microbes became understood in the nineteenth century. In addition to several copper medicinal preparations, it was also observed centuries ago that water contained in copper vessels or transported in copper conveyance systems was of better quality than water contained or transported in other materials.

An antimicrobial surface is coated by an antimicrobial agent that inhibits the ability of microorganisms to grow on the surface of a material. Such surfaces are becoming more widely investigated for possible use in various settings including clinics, industry, and even the home. The most common and most important use of antimicrobial coatings has been in the healthcare setting for sterilization of medical devices to prevent hospital associated infections, which have accounted for almost 100,000 deaths in the United States. In addition to medical devices, linens and clothing can provide a suitable environment for many bacteria, fungi, and viruses to grow when in contact with the human body which allows for the transmission of infectious disease.

Silane-Quats are a class of antimicrobial developed by Dow Corning and first patented in the United States in February 1971 . Subsequent patents were filed throughout the 1970’s by Dow Corning for utilizing its silane-quat as an effective antimicrobial. In doing so, Dow Corning had invented a durable, non-leaching, persistent, surface bonding antimicrobial effective against a wide range of unicellular microorganisms on a variety of surfaces. 

<span class="mw-page-title-main">Composition of electronic cigarette aerosol</span>

The chemical composition of the electronic cigarette aerosol varies across and within manufacturers. Limited data exists regarding their chemistry. However, researchers at Johns Hopkins University analyzed the vape clouds of popular brands such as Juul and Vuse, and found "nearly 2,000 chemicals, the vast majority of which are unidentified."

References

  1. "OUST Aerosol - Clean Scent Ingredients". S. C. Johnson & Son . 2010. Retrieved 2014-02-24.
  2. QB Johnson Manufacturing Archived 2012-05-13 at the Wayback Machine
  3. 40 CFR 261.24; State of Michigan, Department of Environmental Quality, Waste and Hazardous Materials Division, Hazardous Waste File; Lee 8 Storage Facility, Olivet, MI; March 2009 Inspection and analytical results
  4. 1 2 Robertson OH (1949). "Disinfection of the air with triethylene glycol vapor". The American Journal of Medicine. 7 (3): 293–296. doi:10.1016/0002-9343(49)90429-5. PMID   18139414.
  5. Robertson OH, Puck TT, Lemon HF, Clayton GL (1943). "The lethal effect of triethylene glycol vapor on air-borne bacteria and influenza virus". Science. 97 (2510): 142–144. doi:10.1126/science.97.2510.142. PMID   17788521. S2CID   26198638.
  6. 1 2 Mellody M, Bigg E (1946). "The fungicidal action of triethylene glycol". The Journal of Infectious Diseases. 79 (1): 45–46. doi:10.1093/infdis/79.1.45. JSTOR   30089292. PMID   20996927.
  7. Rosebury T, Meiklejohn G, Kingsland LC, Boldt MH (1947). "Disinfection of Clouds of Meningopneumonitis and Psittacosis Viruses with Triethylene Glycol Vapor". Journal of Experimental Medicine. 85 (1): 65–76. doi:10.1084/jem.85.1.65. PMC   2135670 . PMID   19871600.
  8. 1 2 3 Lester W, Robertson OH, Puck TT, Wise H (1949). "The rate of bactericidal action of triethylene glycol vapor on microorganisms dispersed into the air in small droplets". American Journal of Epidemiology. 50 (2): 175–188. doi:10.1093/oxfordjournals.aje.a119352. PMID   18141117.
  9. Lester W, Dunklin E, Robertson OH (1952). "Bactericidal effects of propylene and triethylene glycol vapors on airborne Escherichia coli". Science. 115 (2988): 37, 379–382. doi:10.1126/Science.115.2988.379. PMID   17770126.
  10. Kethley TW, Fincher EL, Cown WB (1956). "A System for the Evaluation of Aerial Disinfectants". Applied and Environmental Microbiology. 4 (5): 237–243. doi:10.1128/aem.4.5.237-243.1956. PMC   1057210 . PMID   13363384.
  11. 1 2 3 Robertson OH, Appel EM, Puck TT, Lemon HM, Ritter MH (September 1948). "A study of the bactericidal activity in vitro of certain glycols and closely related compounds". The Journal of Infectious Diseases. 83 (2): 124–137. doi:10.1093/infdis/83.2.124. PMID   18888328.
  12. Potter TS (1944). "The possibility of prevention of tuberculosis by non-poisonous chemical air disinfection and by killed vaccines". Science. 99 (2577): 406–407. Bibcode:1944Sci....99..406S. doi:10.1126/science.99.2577.406. PMID   17772135.
  13. Rudnick SN, McDevitt JJ, First MW, Spengler JD (2009). "Inactivating influenza viruses on surfaces using hydrogen peroxide or triethylene glycol at low vapor concentrations". American Journal of Infection Control. 37 (10): 813–819. CiteSeerX   10.1.1.148.5118 . doi:10.1016/j.ajic.2009.06.007. PMC   7115294 . PMID   19822378.
  14. Turgeon N, Michel K, Ha TL, Robine E, Moineau S, Duchaine C (2016). "Resistance of Aerosolized Bacterial Viruses to Four Germicidal Products". PLOS ONE. 11 (12): e0168815. Bibcode:2016PLoSO..1168815T. doi: 10.1371/journal.pone.0168815 . PMC   5193356 . PMID   28030577.