1,2-Dichloroethane
IUPAC name 1,2-Dichloroethane
Other names Ethylene dichloride Ethane dichloride Dutch liquid, Dutch oil Freon 150
Identifiers
CAS number	107-06-2 Y
ChemSpider	10 Y
UNII	55163IJI47 Y
KEGG	C06752 Y
ChEMBL	CHEMBL16370 N
RTECS number	KI0525000
Jmol-3D images	Image 1
SMILES ClCCCl
Properties
Molecular formula	C2H4Cl2
Molar mass	98.96 g mol−1
Appearance	Colorless liquid with characteristic odor
Density	1.253 g/cm³, liquid
Melting point	-35 °C, 238 K, -31 °F
Boiling point	84 °C, 357 K, 183 °F
Solubility in water	0.87 g/100 mL (20 °C)
Viscosity	0.84 mPa·s at 20 °C
Structure
Dipole moment	1.80 D
Hazards
MSDS	External MSDS
R-phrases	R11 R45 R36/37/38
S-phrases	S45 S53
Main hazards	Toxic, flammable
NFPA 704	3 3 0
Flash point	13 °C
Related compounds
Related haloalkanes	Methyl chloride Methylene chloride 1,1,1-Trichloroethane
Related compounds	Ethylene Chlorine Vinyl chloride
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The chemical compound 1,2-dichloroethane, commonly known by its old name of ethylene dichloride (EDC), is a chlorinated hydrocarbon, mainly used to produce vinyl chloride monomer (VCM, chloroethene), the major precursor for PVC production. It is a colourless liquid with a chloroform-like odour. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds and as a solvent. It forms azeotropes with many other solvents, including water (b.p. 70.5 C) and other chlorocarbons.^[1]

History[link]

In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Gezelschap der Hollandsche Scheikundigen (Dutch: Society of Dutch Chemists), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas. Although the Gezelschap in practice did not do much in-depth scientific research, they and their publications were highly regarded. Part of that acknowledgement is that 1,2-dichloroethane has been called "Dutch oil" in old chemistry.

Production[link]

Nearly 20 million tons of 1,2-dichloroethane are produced in the United States, Western Europe, and Japan.^[2] Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethene (ethylene) and chlorine.

H₂C=CH₂ + Cl₂ → ClCH₂-CH₂Cl

1,2-dichloroethane is also generated by the copper(II) chloride-catalysed "oxychlorination" of ethylene:

2 H₂C=CH₂ + 4 HCl + O₂ → 2 ClCH₂-CH₂Cl + 2 H₂O

In principle, it can be prepared by the chlorination of ethane and, less directly, from ethanol.

Uses[link]

Vinyl chloride monomer (VCM) production[link]

With approximately 80% of the world's consumption of 1,2-dichloroethane, the major use of 1,2-dichloroethane is in the production of vinyl chloride monomer (VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride.

Cl-CH₂-CH₂-Cl → H₂C=CH-Cl + HCl

The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above.

Other uses[link]

As a good apolar aprotic solvent, 1,2-dichloroethane is used as degreaser and paint remover. As a useful 'building block' reagent, it is used as an intermediate in the production of various organic compounds such as ethylenediamine. In the laboratory it is occasionally used as a source of chlorine, with elimination of ethene and chloride.

Via several steps, 1,2-dichloroethane is a precursor to 1,1,1-trichloroethane, which is used in dry cleaning. Historically, 1,2-dichloroethane was used as an anti-knock additive in leaded fuels.^[3]

Safety[link]

1,2-Dichloroethane is toxic (especially by inhalation due to its high vapour pressure), highly flammable,^[4] and carcinogenic. Its high solubility and 50-year half-life in anoxic aquifers make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of bioremediation.^[5] While the chemical is banned from use by U.S. manufacturers^[6], a case was reported in 2009 of molded plastic consumer products (toys and holiday decorations) from China that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk.^[7] Substitutes are recommended and will vary according to application. Dioxolane and toluene are possible substitutes as solvents. Dichloroethane is unstable in the presence of aluminium metal and, when moist, with zinc and iron.

References[link]

1. ^ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann “Chlorinated Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. http://dx.doi.org/10.1002/14356007.a06_233.pub2
2. ^ J.A. Field & R. Sierra-Alvarez (2004). "Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds". Rev. Environ. Sci. Biotechnol. 3 (3): 185–254. DOI:10.1007/s11157-004-4733-8. 
3. ^ Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics 22 (25): 5154–5178. DOI:10.1021/om030621b. 
4. ^ "1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>.
5. ^ S. De Wildeman & W. Verstraete (25 Mar., 2003). "The quest for microbial reductive dechlorination of C2 to C4 chloroalkanes is warranted". Appl. Microbiol. Biotechnol. 61 (2): 94–102. DOI:10.1007/s00253-002-1174-6. PMID 12655450. 
6. ^ Toxic Christmas: Plastic Ornaments May Pollute Your Air
7. ^ Doucette, WJ and Hall, AJ and Gorder, KA (Winter, 2010). "Emissions of 1, 2-Dichloroethane from Holiday Decorations as a Source of Indoor Air Contamination". Ground Water Monitoring & Remediation 30 (1): 67–73. DOI:10.1111/j.1745-6592.2009.01267.x. 

External links[link]

• Gezelschap der Hollandsche Scheikundigen
• ChemicalLand compound database
• Environmental Chemistry compound database
• Merck Chemicals database
• National Pollutant Inventory - 1,2 Dichlorethane Fact Sheet
• Locating and estimating air emissions from sources of ethylene dichloride, EPA report EPA-450/4-84-007d, March 1984

Rube Goldberg
Born	Reuben Garrett Lucius Goldberg (1883-07-04)July 4, 1883 San Francisco, California, United States
Died	December 7, 1970(1970-12-07) (aged 87)
Resting place	Mount Pleasant Cemetery in Hawthorne, New York
Occupation	Engineer, Sculptor, News Reporter, Cartoonist
Known for	Rube Goldberg machines

Reuben Lucius Goldberg (July 4, 1883 – December 7, 1970) was an American cartoonist, sculptor, author, engineer and inventor.

He is best known for a series of popular cartoons depicting complex gadgets that perform simple tasks in indirect, convoluted ways. These devices, now known as Rube Goldberg machines, are similar to those drawn by W. Heath Robinson in the UK and Storm P in Denmark^{[citation needed]}. Goldberg received many honors in his lifetime, including a Pulitzer Prize for his political cartooning in 1948 and the Banshees' Silver Lady Award 1959.^[1]

Goldberg was a founding member and the first president of the National Cartoonists Society,^[2] and he is the namesake of the Reuben Award, which the organization awards to the Cartoonist of the Year. He is the inspiration for various international competitions, known as Rube Goldberg Machine Contests, which challenge participants to make a complex machine to perform a simple task.

Life[link]

Goldberg was born July 4, 1883, in San Francisco, California, to Jewish parents Max and Hannah Goldberg. He was the second of four children (older brother Garrett, younger brother Walter, and younger sister Lillian). Rube married Irma Seeman in 1916. They lived at 88 Central Park West in New York City and had two sons named Thomas and George. He started drawing when he was only four years old. Goldberg did not share a surname with his children because of the amount of hatred towards him during World War II from the political nature of his cartoons. He ordered his sons to change their names from Goldberg for safety reasons. Both of his sons chose the last name of George, wanting to keep a sense of family cohesiveness. Thomas and George's children now run a company called RGI (Rube Goldberg Incorporated) to maintain the Goldberg name. John George (Thomas's son) is assisted by his cousin Jennifer George^[3] (George's daughter) and John's son Joshua George to keep the family name alive.^[4] Reuben died in 1970 at the age of 87, while his widow, Irma, died 20 years later on April 26, 1990 at the age of 95.^[5]

Career[link]

Rube Goldberg with family, 1929

Goldberg's father was a San Francisco police and fire commissioner, who encouraged the young Reuben to pursue a career in engineering. Rube graduated from the University of California, Berkeley in 1904 with a College of Mining degree^[1] and was hired by the city of San Francisco as an engineer for the Water and Sewers Department. After six months he resigned his position with the city to join the San Francisco Chronicle where he became a sports cartoonist.^[1] The following year, he took a job with the San Francisco Bulletin, where he remained until he moved to New York City in 1907.

Goldberg drew cartoons for five newspapers, including the New York Journal American|New York Evening Journal and the New York Evening Mail. His work entered syndication in 1915, beginning his nationwide popularity. He was syndicated by the McNaught Syndicate from 1922 until 1934.

A prolific artist, Goldberg produced several cartoon series simultaneously, including Mike and Ike (They Look Alike), Boob McNutt, Foolish Questions, Lala Palooza and The Weekly Meeting of the Tuesday Women's Club. The cartoons that brought him lasting fame involved a character named Professor Lucifer Gorgonzola Butts. In that series, Goldberg drew labeled schematics of the comical "inventions" that would later bear his name.

Cultural legacy[link]

This postcard book, Rube Goldberg's Inventions!, was compiled by Maynard Frank Wolfe from the Rube Goldberg Archives. The cover illustration shows Professor Butts and the Self-Operating Napkin. The "Self-Operating Napkin" is activated when the soup spoon (A) is raised to mouth, pulling string (B) and thereby jerking ladle (C), which throws cracker (D) past parrot (E). Parrot jumps after cracker and perch (F) tilts, upsetting seeds (G) into pail (H). Extra weight in pail pulls cord (I), which opens and lights automatic lighter (J), setting off skyrocket (K), which causes sickle (L) to cut string (M) and allow the pendulum with the attached napkin to swing back and forth, thereby wiping chin.

In 1931 the Merriam-Webster dictionary adopted the word "Rube Goldberg" as an adjective defined as accomplishing something simple through complex means.^[6]

Predating Goldberg, the corresponding term in the U.K. was, and still is, "Heath Robinson", after the English illustrator with an equal devotion to odd machinery (although Heath Robinson's creations did not have the same emphasis on the sequential or chain reaction element).

Goldberg's work was commemorated posthumously in 1995 with the inclusion of Rube Goldberg's Inventions, depicting Professor Butts' "Self-Operating Napkin" in the Comic Strip Classics series of U.S. postage stamps.^[7]

Film and television[link]

Rube Goldberg wrote a feature film featuring his machines and sculptures called Soup to Nuts, which was released in 1930 and starred Ted Healy and The Three Stooges.

In the 1962 John Wayne movie Hatari!, an invention to catch monkeys by character Pockets, played by Red Buttons, is described as a "Rube Goldberg."

In the late 1960s and early 70s, educational shows like Sesame Street and The Electric Company routinely showed bits that involved Rube Goldberg devices, including the Rube Goldberg Alphabet Contraption, and the What Happens Next Machine.^[8][9]

Various other films and cartoons have included highly complex machines that perform simple tasks. Among these are Flåklypa Grand Prix, Looney Tunes, Tom and Jerry, Wallace and Gromit, Pee-wee's Big Adventure, The Way Things Go, Edward Scissorhands, Back to the Future, Honey, I Shrunk the Kids, The Goonies, Gremlins, the Saw film series, Chitty Chitty Bang Bang, The Cat from Outer Space, Malcolm, Family Guy, and Waiting...

Also in the Final Destination film series the characters often die in Rube Goldberg-esque ways. In the film The Great Mouse Detective, the villain Ratigan attempts to kill the film's heroes, Basil of Baker Street and David Q. Dawson, with a Rube Goldberg style device. The classic video in this genre was done by the artist duo Peter Fischli & David Weiss in 1987 with their 30 minute video "Der Lauf der Dinge" or "The Way Things Go".

Honda produced a video in 2003 called "The Cog" using many of the same principles that Fischli and Weiss had done in 1987.

In 2005, the American indie/alternative rock band The Bravery released a video for their debut single, "An Honest Mistake," which features the band performing the song in the middle of a Rube Goldberg machine.

In 1999, an episode of The X-Files was titled "The Goldberg Variation". The episode intertwined characters FBI agents Mulder and Scully, a simple apartment super, Henry Weems (Willie Garson) and an ailing young boy, Ritchie Lupone (Shia LaBeouf) in a real-life Goldberg device.

The 2010 music video "This Too Shall Pass - RGM Version" by the rock band OK Go features a machine that, after four minutes of kinetic activity, shoots the band members in the face with paint. "RGM" presumably stands for Rube Goldberg Machine.^[10]

Games[link]

The popular 1963 board game Mouse Trap, as well as its sequels Crazy Clock (1964), and Fish Bait (1965) are based on Rube Goldberg machines.^{[citation needed]} Some examples of Goldberg-inspired video games are Incredibots, LittleBigPlanet, LittleBigPlanet 2, the 1990s-era series of The Incredible Machine games, and Crazy Machines.^{[citation needed]}

See also[link]

• Chindōgu
• Deathtrap (plot device)
• Domino effect
• Frederick Rowland Emett
• Jean Tinguely, Swiss artist who created Rube Goldberg–like sculptures
• Mickey One
• PythagoraSwitch
• Robert Storm Petersen (Storm P.), a Danish contemporary artist who drew "inventions" similar to Rube Goldberg's
• Steampunk

References[link]

External links[link]

• Great Video of Goldberg-type device made from Legos
• Toonopedia entry
• Smithsonian Archives of American Art: Oral History Interview, 1970
• Annual National Rube Goldberg Machine Contest
• NCS Awards
• Rube Goldberg in 'Creative Contraptions'
• IMDB biography
• Rube Goldberg Honda Commercial, "Cog", at Snopes.com
• Guide to the Rube Goldberg Papers at The Bancroft Library
• 10 Viral Rube Goldberg clips at Salon.com