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Pixel
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This article is about the picture element. For other uses, including for the plural form "pixels", see Pixel (disambiguation).
This example shows an image with a portion greatly enlarged, in which the individual pixels are rendered as small squares and can easily be seen.
A photograph of sub-PIXEL display elements on a laptop's LCD screen
In digital imaging, a pixel, pel,[1] dots, or picture element[2] is a physical point in a raster image, or the smallest addressable element in an all points addressable display device; so it is the smallest controllable element of a picture represented on the screen.
Each pixel is a sample of an original image; more samples typically provide more accurate representations of the original. The intensity of each pixel is variable. In color imaging systems, a color is typically represented by three or four component intensities such as red, green, and blue, or cyan, magenta, yellow, and black.
In some contexts (such as descriptions of camera sensors), pixel refers to a single scalar element of a multi-component representation (more precisely called a photosite in the camera sensor context, although the neologism sensel is sometimes used to describe the elements of a digital camera's sensor),[3] while in yet other contexts it may refer to the set of component intensities for a spatial position. Drawing a distinction between pixels, photosites, and samples may reduce confusion when describing color systems that use chroma subsampling or cameras that use Bayer filter to produce color components via upsampling.
The word pixel is a portmanteau of pix (from "pictures", shortened to "pics") and el (for "element"); similar formations with 'el' include the words voxel[4] and texel.[4]
Contents
[hide]
1 Etymology
2 Technical
2.1 Sampling patterns
2.2 Resolution of computer monitors
2.3 Resolution of telescopes
2.4 Bits per pixel
2.5 Subpixels
3 Megapixel
4 See also
5 References
6 External links
Etymology[edit]
The word "pixel" was first published in 1965 by Frederic C. Billingsley of JPL, to describe the picture elements of video images from space probes to the Moon and Mars.[5] Billingsley had learned the word from Keith E. McFarland, at the Link Division of General Precision in Palo Alto, who in turn said he did not know where it originated. McFarland said simply it was "in use at the time" (circa 1963).[6]
The word is a combination of pix, for picture, and element. The word pix appeared in Variety magazine headlines in 1932, as an abbreviation for the word pictures, in reference to movies.[7] By 1938, "pix" was being used in reference to still pictures by photojournalists.[6]
The concept of a "picture element" dates to the earliest days of television, for example as "Bildpunkt" (the German word for pixel, literally 'picture point') in the 1888 German patent of Paul Nipkow. According to various etymologies, the earliest publication of the term picture element itself was in Wireless World magazine in 1927,[8] though it had been used earlier in various U.S. patents filed as early as 1911.[9]
Some authors explain pixel as picture cell, as early as 1972.[10] In graphics and in image and video processing, pel is often used instead of pixel.[11] For example, IBM used it in their Technical Reference for the original PC.
Pixels, abbreviated as 'px,' are also a unit of measurement commonly used in graphic and web design, equivalent to roughly 1⁄96 inch (0.26 mm). This measurement is used to make sure a given element will display as the same size no matter what screen resolution views it.[12]
Pixilation, spelled with a second i, is an unrelated filmmaking technique that dates to the beginnings of cinema, in which live actors are posed frame by frame and photographed to create stop-motion animation. An archaic British word meaning "possession by spirits (pixies)", the term has been used to describe the animation process since the early 1950s; various animators, including Norman McLaren and Grant Munro, are credited with popularizing it.[13]
Technical[edit]
A pixel does not need to be rendered as a small square. This image shows alternative ways of reconstructing an image from a set of pixel values, using dots, lines, or smooth filtering.
A pixel is generally thought of as the smallest single component of a digital image. However, the definition is highly context-sensitive. For example, there can be "printed pixels" in a page, or pixels carried by electronic signals, or represented by digital values, or pixels on a display device, or pixels in a digital camera (photosensor elements). This list is not exhaustive and, depending on context, synonyms include pel, sample, byte, bit, dot, and spot. Pixels can be used as a unit of measure such as: 2400 pixels per inch, 640 pixels per line, or spaced 10 pixels apart.
The measures dots per inch (dpi) and pixels per inch (ppi) are sometimes used interchangeably, but have distinct meanings, especially for printer devices, where dpi is a measure of the printer's density of dot (e.g. ink droplet) placement.[14] For example, a high-quality photographic image may be printed with 600 ppi on a 1200 dpi inkjet printer.[15] Even higher dpi numbers, such as the 4800 dpi quoted by printer manufacturers since 2002, do not mean much in terms of achievable resolution.[16]
The more pixels used to represent an image, the closer the result can resemble the original. The number of pixels in an image is sometimes called the resolution, though resolution has a more specific definition. Pixel counts can be expressed as a single number, as in a "three-megapixel" digital camera, which has a nominal three million pixels, or as a pair of numbers, as in a "640 by 480 display", which has 640 pixels from side to side and 480 from top to bottom (as in a VGA display), and therefore has a total number of 640×480 = 307,200 pixels or 0.3 megapixels.
The pixels, or color samples, that form a digitized image (such as a JPEG file used on a web page) may or may not be in one-to-one correspondence with screen pixels, depending on how a computer displays an image. In computing, an image composed of pixels is known as a bitmapped image or a raster image. The word raster originates from television scanning patterns, and has been widely used to describe similar halftone printing and storage techniques.
Sampling patterns[edit]
For convenience, pixels are normally arranged in a regular two-dimensional grid. By using this arrangement, many common operations can be implemented by uniformly applying the same operation to each pixel independently. Other arrangements of pixels are possible, with some sampling patterns even changing the shape (or kernel) of each pixel across the image. For this reason, care must be taken when acquiring an image on one device and displaying it on another, or when converting image data from one pixel format to another.
For example:
Text rendered using ClearType
LCD screens typically use a staggered grid, where the red, green, and blue components are sampled at slightly different locations. Subpixel rendering is a technology which takes advantage of these differences to improve the rendering of text on LCD screens.
The vast majority of color digital cameras use a Bayer filter, resulting in a regular grid of pixels where the color of each pixel depends on its position on the grid.
A clipmap uses a hierarchical sampling pattern, where the size of the support of each pixel depends on its location within the hierarchy.
Warped grids are used when the underlying geometry is non-planar, such as images of the earth from space.[17]
The use of non-uniform grids is an active research area, attempting to bypass the traditional Nyquist limit.[18]
Pixels on computer monitors are normally "square" (that is, have equal horizontal and vertical sampling pitch); pixels in other systems are often "rectangular" (that is, have unequal horizontal and vertical sampling pitch – oblong in shape), as are digital video formats with diverse aspect ratios, such as the anamorphic widescreen formats of the Rec. 601 digital video standard.
Resolution of computer monitors[edit]
Computers can use pixels to display an image, often an abstract image that represents a GUI. The resolution of this image is called the display resolution and is determined by the video card of the computer. LCD monitors also use pixels to display an image, and have a native resolution. Each pixel is made up of triads, with the number of these triads determining the native resolution. On some CRT monitors, the beam sweep rate may be fixed, resulting in a fixed native resolution. Most CRT monitors do not have a fixed beam sweep rate, meaning they do not have a native resolution at all - instead they have a set of resolutions that are equally well supported. To produce the sharpest images possible on an LCD, the user must ensure the display resolution of the computer matches the native resolution of the monitor.
Resolution of telescopes[edit]
The pixel scale used in astronomy is the angular distance between two objects on the sky that fall one pixel apart on the detector (CCD or infrared chip). The scale s measured in radians is the ratio of the pixel spacing p and focal length f of the preceding optics, s=p/f. (The focal length is the product of the focal ratio by the diameter of the associated lens or mirror.) Because p is usually expressed in units of arcseconds per pixel, because 1 radian equals 180/π*3600≈206,265 arcseconds, and because diameters are often given in millimeters and pixel sizes in micrometers which yields another factor of 1,000, the formula is often quoted as s=206p/f.
Bits per pixel[edit]
Main article: Color depth
The number of distinct colors that can be represented by a pixel depends on the number of bits per pixel (bpp). A 1 bpp image uses 1-bit for each pixel, so each pixel can be either on or off. Each additional bit doubles the number of colors available, so a 2 bpp image can have 4 colors, and a 3 bpp image can have 8 colors:
1 bpp, 21 = 2 colors (monochrome)
2 bpp, 22 = 4 colors
3 bpp, 23 = 8 colors
...
8 bpp, 28 = 256 colors
16 bpp, 216 = 65,536 colors ("Highcolor" )
24 bpp, 224 = 16,777,216 colors ("Truecolor")
For color depths of 15 or more bits per pixel, the depth is normally the sum of the bits allocated to each of the red, green, and blue components. Highcolor, usually meaning 16 bpp, normally has five bits for red and blue each, and six bits for green, as the human eye is more sensitive to errors in green than in the other two primary colors. For applications involving transparency, the 16 bits may be divided into five bits each of red, green, and blue, with one bit left for transparency. A 24-bit depth allows 8 bits per component. On some systems, 32-bit depth is available: this means that each 24-bit pixel has an extra 8 bits to describe its opacity (for purposes of combining with another image).
Subpixels[edit]
Geometry of color elements of various CRT and LCD displays; phosphor dots in the color display of CRTs (top row) bear no relation to pixels or subpixels.
Many display and image-acquisition systems are, for various reasons, not capable of displaying or sensing the different color channels at the same site. Therefore, the pixel grid is divided into single-color regions that contribute to the displayed or sensed color when viewed at a distance. In some displays, such as LCD, LED, and plasma displays, these single-color regions are separately addressable elements, which have come to be known as subpixels.[19] For example, LCDs typically divide each pixel vertically into three subpixels. When the square pixel is divided into three subpixels, each subpixel is necessarily rectangular. In display industry terminology, subpixels are often referred to as pixels,[by whom?] as they are the basic addressable elements in a viewpoint of hardware, and hence pixel circuits rather than subpixel circuits is used.
Most digital camera image sensors use single-color sensor regions, for example using the Bayer filter pattern, and in the camera industry these are known as pixels just like in the display industry, not subpixels.
For systems with subpixels, two different approaches can be taken:
The subpixels can be ignored, with full-color pixels being treated as the smallest addressable imaging element; or
The subpixels can be included in rendering calculations, which requires more analysis and processing time, but can produce apparently superior images in some cases.
This latter approach, referred to as subpixel rendering, uses knowledge of pixel geometry to manipulate the three colored subpixels separately, producing an increase in the apparent resolution of color displays. While CRT displays use red-green-blue-masked phosphor areas, dictated by a mesh grid called the shadow mask, it would require a difficult calibration step to be aligned with the displayed pixel raster, and so CRTs do not currently use subpixel rendering.
The concept of subpixels is related to samples.
Megapixel[edit]
Diagram of common sensor resolutions of digital cameras including megapixel values
A megapixel (MP) is a million pixels; the term is used not only for the number of pixels in an image, but also to express the number of image sensor elements of digital cameras or the number of display elements of digital displays. For example, a camera that makes a 2048×1536 pixel image (3,145,728 finished image pixels) typically uses a few extra rows and columns of sensor elements and is commonly said to have "3.2 megapixels" or "3.4 megapixels", depending on whether the number reported is the "effective" or the "total" pixel count.[20]
Digital cameras use photosensitive electronics, either charge-coupled device (CCD) or complementary metal–oxide–semiconductor (CMOS) image sensors, consisting of a large number of single sensor elements, each of which records a measured intensity level. In most digital cameras, the sensor array is covered with a patterned color filter mosaic having red, green, and blue regions in the Bayer filter arrangement, so that each sensor element can record the intensity of a single primary color of light. The camera interpolates the color information of neighboring sensor elements, through a process called demosaicing, to create the final image. These sensor elements are often called "pixels", even though they only record 1 channel (only red, or green, or blue) of the final color image. Thus, two of the three color channels for each sensor must be interpolated and a so-called N-megapixel camera that produces an N-megapixel image provides only one-third of the information that an image of the same size could get from a scanner. Thus, certain color contrasts may look fuzzier than others, depending on the allocation of the primary colors (green has twice as many elements as red or blue in the Bayer arrangement).
DxO Labs invented the Perceptual MegaPixel (P-MPix) to measure the sharpness that a camera produces when paired to a particular lens – as opposed to the MP a manufacturer states for a camera product which is based only on the camera's sensor. The new P-MPix claims to be a more accurate and relevant value for photographers to consider when weighing-up camera sharpness.[21] As of mid-2013, the Sigma 35mm f/1.4 DG HSM lens mounted on a Nikon D800 has the highest measured P-MPix. However, with a value of 23 MP, it still wipes-off more than one-third of the D800's 36.3 MP sensor.[22]
One new method to add Megapixels has been introduced in a Micro Four Thirds System camera which only uses 16MP sensor, but can produce 64MP RAW (40MP JPEG) by making two exposures, shifting the sensor by a half pixel between them. Using a tripod to take level multi-shots within an instance, the multiple 16MP images are then generated into a unified 64MP image.[23]
See also[edit]
Computer graphics portal
Computer display standard
Dexel
Gigapixel image
Image resolution
Intrapixel and Interpixel processing
LCD crosstalk
PenTile matrix family
Pixel advertising
Pixel art
Pixel art scaling algorithms
Pixel aspect ratio
Point (typography)
Glossary of video terms
Voxel
References[edit]
Jump up ^ Foley, J. D.; Van Dam, A. (1982). Fundamentals of Interactive Computer Graphics. Reading, MA: Addison-Wesley. ISBN 0201144689.
Jump up ^ Rudolf F. Graf (1999). Modern Dictionary of Electronics. Oxford: Newnes. p. 569. ISBN 0-7506-4331-5.
Jump up ^ Michael Goesele (2004). New Acquisition Techniques for Real Objects and Light Sources in Computer Graphics. Books on Demand. ISBN 3-8334-1489-8. Archived from the original on 2018-01-22.
^ Jump up to: a b Foley, James D.; Andries van Dam; John F. Hughes; Steven K. Feiner (1990). "Spatial-partitioning representations; Surface detail". Computer Graphics: Principles and Practice. The Systems Programming Series. Addison-Wesley. ISBN 0-201-12110-7. These cells are often called voxels (volume elements), in analogy to pixels.
Jump up ^ Fred C. Billingsley, "Processing Ranger and Mariner Photography," in Computerized Imaging Techniques, Proceedings of SPIE, Vol. 0010, pp. XV-1–19, Jan. 1967 (Aug. 1965, San Francisco).
^ Jump up to: a b Lyon, Richard F. (2006). A brief history of 'pixel' Archived 2009-02-19 at the Wayback Machine.. IS&T/SPIE Symposium on Electronic Imaging.
Jump up ^ "Online Etymology Dictionary". Archived from the original on 2010-12-30.
Jump up ^ Safire, William (2 April 1995). "Modem, I'm Odem". On Language. The New York Times. Archived from the original on 9 July 2017. Retrieved 21 December 2017.
Jump up ^ US 1175313, Alf Sinding-Larsen, "Transmission of pictures of moving objects", published 1916-03-14
Jump up ^ Robert L. Lillestrand (1972). "Techniques for Change Detection". IEEE Trans. Comput. C–21 (7).
Jump up ^ Lewis, Peter H. (12 February 1989). "Compaq Sharpens Its Video Option". The Executive Computer. The New York Times. Archived from the original on 20 December 2017. Retrieved 21 December 2017.
Jump up ^ "CSS: em, px, pt, cm, in…". w3.org. 8 November 2017. Archived from the original on 6 November 2017. Retrieved 21 December 2017.
Jump up ^ Tom Gasek (17 January 2013). Frame by Frame Stop Motion: NonTraditional Approaches to Stop Motion Animation. Taylor & Francis. p. 2. ISBN 978-1-136-12933-9. Archived from the original on 22 January 2018.
Jump up ^ Derek Doeffinger (2005). The Magic of Digital Printing. Lark Books. p. 24. ISBN 1-57990-689-3. Archived from the original on 2018-01-22.
Jump up ^ "Experiments with Pixels Per Inch (PPI) on Printed Image Sharpness". ClarkVision.com. July 3, 2005. Archived from the original on December 22, 2008.
Jump up ^ Harald Johnson (2002). Mastering Digital Printing. Thomson Course Technology. p. 40. ISBN 1-929685-65-3.
Jump up ^ "Image registration of blurred satellite images". staff.utia.cas.cz. 28 February 2001. Archived from the original on 20 June 2008. Retrieved 2008-05-09.
Jump up ^ "Image representation by a new optimal non-uniform morphological sampling". Pattern Recognition. 33 (6): 961–977. doi:10.1016/S0031-3203(99)00158-2. Retrieved 2008-05-09.
Jump up ^ "Subpixel in Science". dictionary.com. Archived from the original on 5 July 2015. Retrieved 4 July 2015.
Jump up ^ "Now a megapixel is really a megapixel". Archived from the original on 2013-07-01.
Jump up ^ "Looking for new photo gear? DxOMark's Perceptual Megapixel can help you!". dxomark.com. 17 December 2012. Archived from the original on 8 May 2017.
Jump up ^ DxO. "Lens scoring versus Optical Metrics - DxOMark". Archived from the original on 2013-05-26.
Jump up ^ Damien Demolder (February 14, 2015). "Soon, 40MP without the tripod: A conversation with Setsuya Kataoka from Olympus". Archived from the original on March 11, 2015. Retrieved March 8, 2015.
External links[edit]
A Pixel Is Not A Little Square: Microsoft Memo by computer graphics pioneer Alvy Ray Smith.
Video of Lyon's talk on pixel history at the Computer History Museum
Square and non-Square Pixels: Technical info on pixel aspect ratios of modern video standards (480i, 576i, 1080i, 720p), plus software implications.
120 Megapixel is here now: A lot of information about MegaPixel and Gigapixel.
How a TV Works in Slow Motion - The Slow Mo Guys – YouTube video by The Slow Mo Guys
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text:
Styrene
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Styrene
Names
Preferred IUPAC name
Ethenylbenzene[1]
Other names
Styrene[1]
Vinylbenzene
Phenylethene
Phenylethylene
Cinnamene
Styrol
Diarex HF 77
Styrolene
Styropol
Identifiers
CAS Number
100-42-5 Y
3D model (JSmol)
Interactive image
ChEBI
CHEBI:27452 Y
ChEMBL
ChEMBL285235 Y
ChemSpider
7220 Y
ECHA InfoCard 100.002.592
KEGG
C07083
PubChem CID
7501
RTECS number WL3675000
UNII
44LJ2U959V Y
InChI[show]
InChI=1S/C8H8/c1-2-8-6-4-3-5-7-8/h2-7H,1H2 Y
Key: PPBRXRYQALVLMV-UHFFFAOYSA-N Y
SMILES[show]
c1ccccc1C=C
Properties
Chemical formula
C8H8
Molar mass 104.15 g/mol
Appearance colorless oily liquid
Odor sweet, floral[2]
Density 0.909 g/cm3
Melting point −30 °C (−22 °F; 243 K)
Boiling point 145 °C (293 °F; 418 K)
Solubility in water
0.03% (20°C)[2]
log P 2.70 [3]
Vapor pressure 5 mmHg (20°C)[2]
Magnetic susceptibility (χ)
-68.2·10−6 cm3/mol
Refractive index (nD)
1.5469
Viscosity 0.762 cP at 20 °C
Structure
Dipole moment
0.13 D
Hazards
Main hazards flammable, toxic
Safety data sheet MSDS
R-phrases (outdated) R10 R36
S-phrases (outdated) S38 S20 S23
NFPA 704
3
2
2
Flash point 31 °C (88 °F; 304 K)
Explosive limits 0.9%-6.8%[2]
Lethal dose or concentration (LD, LC):
LC50 (median concentration)
2194 ppm (mouse, 4 hr)
5543 ppm (rat, 4 hr)[4]
LCLo (lowest published)
10,000 ppm (human, 30 min)
2771 ppm (rat, 4 hr)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 100 ppm C 200 ppm 600 ppm (5-minute maximum peak in any 3 hours)[2]
REL (Recommended)
TWA 50 ppm (215 mg/m3) ST 100 ppm (425 mg/m3)[2]
IDLH (Immediate danger)
700 ppm[2]
Related compounds
Related styrenes;
related aromatic compounds
Polystyrene, Stilbene;
Ethylbenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is Y ?)
Infobox references
Styrene, also known as ethenylbenzene, vinylbenzene, and phenylethene, is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid that evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene is the precursor to polystyrene and several copolymers. Approximately 25 million tonnes (55 billion pounds) of styrene were produced in 2010.[5]
Contents
[hide]
1 Occurrence, history, and use
1.1 Natural occurrence
1.2 History
1.3 Industrial production from ethylbenzene
1.4 Other industrial routes
1.4.1 From ethylbenzene hydroperoxide
1.4.2 From toluene and methanol
1.4.3 From benzene and ethane
1.5 Laboratory synthesis
2 Polymerization
3 Health effects
4 References
5 External links
Occurrence, history, and use[edit]
Natural occurrence[edit]
Styrene is named for storax balsam, the resin of Liquidambar trees of the Altingiaceae plant family. Styrene occurs naturally in small quantities in some plants and foods (cinnamon, coffee beans, and peanuts)[6] and is also found in coal tar.
History[edit]
In 1839, the German apothecary Eduard Simon isolated a volatile liquid from the resin (called storax or styrax (Latin)) of the American sweetgum tree (Liquidambar styraciflua). He called the liquid "Styrol" (now: "styrene").[7][8] He also noticed that when Styrol was exposed to air, light, or heat, it gradually transformed into a hard, rubber-like substance, which he called "Styroloxyd" (styrol oxide, now: "polystyrene").[9] By 1845, the German chemist August Hofmann and his student John Blyth (1814–1871) had determined Styrol's empirical formula: C8H8.[10] They had also determined that Simon's "Styroloxyd" — which they renamed "Metastyrol" — had the same empirical formula as Styrol.[11] Furthermore, they could obtain Styrol by dry-distilling Metastyrol.[12] In 1865, the German chemist Emil Erlenmeyer found that Styrol could form a dimer,[13] and in 1866 the French chemist Marcelin Berthelot stated that Metastyrol was a polymer of Styrol.[14] Meanwhile, other chemists had been investigating another component of storax, namely, cinnamic acid. They had found that cinnamic acid could be decarboxylated to form cinnamène (or cinnamol), which appeared to be Styrol. In 1845, French chemist Emil Kopp suggested that the two compounds were identical,[15] and in 1866, Erlenmeyer suggested that both cinnamol and Styrol might be vinyl benzene.[16] However, the Styrol that was obtained from cinnamic acid seemed different from the Styrol that was obtained by distilling storax resin: the latter was optically active.[17] Eventually, in 1876, the Dutch chemist van 't Hoff resolved the ambiguity: the optical activity of the Styrol that was obtained by distilling storax resin was due to a contaminant.[18]
Industrial production from ethylbenzene[edit]
The modern method for production of styrene by dehydrogenation of ethylbenzene was first achieved in the 1930s.[19] The production of styrene increased dramatically during the 1940s, when it was used as a feedstock for synthetic rubber. Because styrene is produced on such a large scale, ethylbenzene is in turn prepared on a prodigious scale (by alkylation of benzene with ethylene).[19] Ethylbenzene is mixed in the gas phase with 10–15 times its volume of high-temperature steam, and passed over a solid catalyst bed. Most ethylbenzene dehydrogenation catalysts are based on iron(III) oxide, promoted by several percent potassium oxide or potassium carbonate.
Steam serves several roles in this reaction. It is the source of heat for powering the endothermic reaction, and it removes coke that tends to form on the iron oxide catalyst through the water gas shift reaction. The potassium promoter enhances this decoking reaction. The steam also dilutes the reactant and products, shifting the position of chemical equilibrium towards products. A typical styrene plant consists of two or three reactors in series, which operate under vacuum to enhance the conversion and selectivity. Typical per-pass conversions are ca. 65% for two reactors and 70-75% for three reactors. Selectivity to styrene is 93-97%. The main byproducts are benzene and toluene. Because styrene and ethylbenzene have similar boiling points (145 and 136 °C, respectively), their separation requires tall distillation towers and high return/reflux ratios. At its distillation temperatures, styrene tends to polymerize. To minimize this problem, early styrene plants added elemental sulfur to inhibit the polymerization. During the 1970s, new free radical inhibitors consisting of nitrated phenol-based retarders were developed. More recently, a number of additives have been developed that exhibit superior inhibition against polymerization. However, the nitrated phenols are still widely used because of their relatively low cost. These reagents are added prior to the distillation.
Improving conversion and so reducing the amount of ethylbenzene that must be separated is the chief impetus for researching alternative routes to styrene. Other than the POSM process, none of these routes such as obtaining styrene from butadiene have been commercially demonstrated.
Other industrial routes[edit]
From ethylbenzene hydroperoxide[edit]
Styrene is also co-produced commercially in a process known as POSM (Lyondell Chemical Company) or SM/PO (Shell) for styrene monomer / propylene oxide. In this process ethylbenzene is treated with oxygen to form the ethylbenzene hydroperoxide. This hydroperoxide is then used to oxidize propylene to propylene oxide. The resulting 1-phenylethanol is dehydrated to give styrene:
From toluene and methanol[edit]
Styrene can be produced from toluene and methanol, which are cheaper raw materials than those in the conventional process. This process has suffered from low selectivity associated with the competing decomposition of methanol.[20] Exelus Inc. claims to have developed this process with commercially viable selectivities, at 400-425 °C and atmospheric pressure, by forcing these components through a proprietary zeolitic catalyst. It is reported[21] that an approximately 9:1 mixture of styrene and ethylbenzene is obtained, with a total styrene yield of over 60%.[22]
From benzene and ethane[edit]
Another route to styrene involves the reaction of benzene and ethane. This process is being developed by Snamprogetti S.p.A. and Dow. Ethane, along with ethylbenzene, is fed to a dehydrogenation reactor with a catalyst capable of simultaneously producing styrene and ethylene. The dehydrogenation effluent is cooled and separated and the ethylene stream is recycled to the alkylation unit. The process attempts to overcome previous shortcomings in earlier attempts to develop production of styrene from ethane and benzene, such as inefficient recovery of aromatics, production of high levels of heavies and tars, and inefficient separation of hydrogen and ethane. Development of the process is ongoing.[23]
Laboratory synthesis[edit]
A laboratory synthesis of styrene entails the decarboxylation of cinnamic acid:[24]
C6H5CH=CHCO2H → :C6H5CH=CH2 + CO2
Styrene was first prepared by this method.[25]
Polymerization[edit]
The presence of the vinyl group allows styrene to polymerize. Commercially significant products include polystyrene, ABS, styrene-butadiene (SBR) rubber, styrene-butadiene latex, SIS (styrene-isoprene-styrene), S-EB-S (styrene-ethylene/butylene-styrene), styrene-divinylbenzene (S-DVB), styrene-acrylonitrile resin (SAN), and unsaturated polyesters used in resins and thermosetting compounds. These materials are used in rubber, plastic, insulation, fiberglass, pipes, automobile and boat parts, food containers, and carpet backing.
Health effects[edit]
Styrene is regarded as a "known carcinogen", especially in case of eye contact, but also in case of skin contact, of ingestion and of inhalation, according to several sources.[19][26][27][28] Styrene is largely metabolized into styrene oxide in humans, resulting from oxidation by cytochrome P450. Styrene oxide is considered toxic, mutagenic, and possibly carcinogenic. Styrene oxide is subsequently hydrolyzed in vivo to styrene glycol by the enzyme epoxide hydrolase.[29] The U.S. Environmental Protection Agency (EPA) has described styrene to be "a suspected toxin to the gastrointestinal tract, kidney, and respiratory system, among others".[30][31] On 10 June 2011, the U.S. National Toxicology Program has described styrene as "reasonably anticipated to be a human carcinogen".[32][33] However, a STATS author describes[34] a review that was done on scientific literature and concluded that "The available epidemiologic evidence does not support a causal relationship between styrene exposure and any type of human cancer".[35] Despite this claim, work has been done by Danish researchers to investigate the relationship between occupational exposure to styrene and cancer. They concluded, "The findings have to be interpreted with caution, due to the company based exposure assessment, but the possible association between exposures in the reinforced plastics industry, mainly styrene, and degenerative disorders of the nervous system and pancreatic cancer, deserves attention".[36] The Danish EPA recently concluded that the styrene data do not support a cancer concern for styrene.[37]
The U.S. EPA does not have a cancer classification for styrene,[38] but it has been the subject of their Integrated Risk Information System (IRIS) program.[39] The U.S. National Toxicology Program of the U.S. Department of Health and Human Services has determined that styrene is "reasonably anticipated to be a human carcinogen". [40]
Various regulatory bodies refer to styrene, in various contexts, as a possible or potential human carcinogen. The International Agency for Research on Cancer considers styrene to be "possibly carcinogenic to humans".[41]
References[edit]
^ Jump up to: a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 4, 55, 379. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Jump up to: a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0571". National Institute for Occupational Safety and Health (NIOSH).
Jump up ^ "Styrene_msds".
^ Jump up to: a b "Styrene". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Jump up ^ New Process for Producing Styrene Cuts Costs, Saves Energy, and Reduces Greenhouse Gas Emissions Archived 21 April 2013 at the Wayback Machine., U.S. Department of Energy.
Jump up ^ MO.), Steele, D.H. (Midwest Research Institute, Kansas City,; M.J., Thornburg,; J.S., Stanley,; R.R., Miller,; R., Brooke,; J.R., Cushman,; G., Cruzan, (1994). "Determination of styrene in selected foods". Journal of Agricultural and Food Chemistry. ISSN 0021-8561. Archived from the original on 14 February 2018.
Jump up ^ Simon, E. (1839) "Ueber den flüssigen Storax (Styrax liquidus)" (On liquid storax (Styrax liquidus), Annalen der Chemie, 31 : 265–277. From p. 268: "Das flüchtige Oel, für welches ich den Namen Styrol vorschlage, … " (The volatile oil, for which I suggest the name "styrol", … )
Jump up ^ For further details of the history of styrene, see: F. W. Semmler, Die ätherischen Öle nach ihren chemischen Bestandteilen unter Berücksichtigung der geschichtlichen Entwicklung [The volatile liquids according to their chemical components with regard to historical development], vol. 4 (Leipzig, Germany, Veit & Co., 1907), § 327. Styrol, pp. 24-28. Archived 1 May 2018 at the Wayback Machine.
Jump up ^ (Simon, 1839), p. 268. From p. 268: "Für den festen Rückstand würde der Name Styroloxyd passen." (For the solid residue, the name "styrol oxide" would fit.)
Jump up ^ See:
Blyth, John; Hofmann, Aug. Wilhelm (1845a). "On styrole, and some of the products of its decomposition". Memoirs and Proceedings of the Chemical Society of London. 2: 334–358. Archived from the original on 1 May 2018. ; see p. 339.
Reprinted in: Blyth, John; Hofmann, Aug. Wilhelm (August 1845b). "On styrole, and some of the products of its decomposition". Philosophical Magazine. 3rd series. 27 (178): 97–121. ; see p. 102.
German translation: Blyth, John; Hofmann, Aug. Wilh. (1845c). "Ueber das Styrol und einige seiner Zersetzungsproducte" [On styrol and some of its decomposition products]. Annalen der Chemie und Pharmacie (in German). 53 (3): 289–329. ; see p. 297.
Note that Blyth and Hofmann state the empirical formula of Styrol as C16H8 because at that time, some chemists used the wrong atomic mass for carbon (6 instead of 12).
Jump up ^ (Blyth and Hofmann, 1845a), p. 348. From p. 348: "Analysis as well as synthesis has equally proved that styrol and the vitreous mass (for which we propose the name of metastyrol) possess the same constitution per cent."
Jump up ^ (Blyth and Hofmann, 1845a), p. 350.
Jump up ^ Erlenmeyer, Emil (1865) "Ueber Distyrol, ein neues Polymere des Styrols" (On distyrol, a new polymer of styrol), Annalen der Chemie, 135 : 122–123.
Jump up ^ Berthelot, M. (1866) "Sur les caractères de la benzine et du styrolène, comparés avec ceux des autres carbures d'hydrogène" (On the characters of benzene and styrene, compared with those of other hydrocarbons), Bulletin de la Société Chimique de Paris, 2nd series, 6 : 289–298. From p. 294: "On sait que le styrolène chauffé en vase scellé à 200°, pendant quelques heures, se change en un polymère résineux (métastyrol), et que ce polymère, distillé brusquement, reproduit le styrolène." (One knows that styrene [when] heated in a sealed vessel at 200°C, for several hours, is changed into a resinous polymer (polystyrene), and that this polymer, [when] distilled abruptly, reproduces styrene.)
Jump up ^ Kopp, E. (1845), "Recherches sur l'acide cinnamique et sur le cinnamène" Archived 8 November 2016 at the Wayback Machine. (Investigations of cinnamic acid and cinnamen), Comptes rendus, 21 : 1376-1380. From p. 1380: "Je pense qu'il faudra désormais remplacer le mot de styrol par celui de cinnamène, et le métastyrol par le métacinnamène." (I think that henceforth one will have to replace the word "styrol" with that of "cinnamène", and "metastyrol" with "metacinnamène".)
Jump up ^ Erlenmeyer, Emil (1866) "Studien über die s.g. aromatischen Säuren" (Studies of the so-called aromatic acids), Annalen der Chemie, 137 : 327–359 ; see p. 353.
Jump up ^ Berthelot, Marcellin (1867) "Sur les états isomériques du styrolène" (On the isomeric states of styrene), Annales de Chimie et de Physique, 4th series, 12 : 159–161. From p. 160: "1° Le carbure des cinnamates est privé de pouvoir rotatoire, tandis que le carbure du styrax dévie de 3 degrés la teinte de passage (l = 100 mm)." (1. The carbon [atom] of cinnamates is bereft of rotary power [i.e., the ability to rotate polarized light], whereas the carbon of styrax deflects by 3 degrees the neutral tint [i.e., the relative orientation of the polarized quartz plates at which the light through the polarimeter appears colorless] (length = 100 mm). [For further details about 19th century polarimeters, see: William Spottiswode, Polarisation of Light, 4th ed. (London, England: Macmillan and Co., 1883), pp. 51-52. Archived 10 September 2010 at the Wayback Machine.)
Jump up ^ van 't Hoff, J. H. (1876) "Die Identität von Styrol und Cinnamol, ein neuer Körper aus Styrax" (The identity of styrol and cinnamol, a new substance from styrax), Berichte der deutschen chemischen Gesellschaft, 9 : 5-6.
^ Jump up to: a b c Denis H. James; William M. Castor (2007), "Styrene", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 1, doi:10.1002/14356007.a25_329.pub2, ISBN 3527306730
Jump up ^ Yashima, Tatsuaki; Sato, Keiichi; Hayasaka, Tomoki; Hara, Nobuyoshi (1972). "Alkylation on synthetic zeolites: III. Alkylation of toluene with methanol and formaldehyde on alkali cation exchanged zeolites". Journal of Catalysis. 26 (3): 303–312. doi:10.1016/0021-9517(72)90088-7.
Jump up ^ "Welcome to ICIS". www.icis.com. Retrieved 1 May 2018.
Jump up ^ Stephen K. Ritter, Chemical & Engineering News, 19 March 2007, p.46.
Jump up ^ "CHEMSYSTEMS.COM" (PDF). www.chemsystems.com. Archived (PDF) from the original on 8 July 2011. Retrieved 1 May 2018.
Jump up ^ Abbott, T. W.; Johnson, J. R. (1941). "Phenylethylene (Styrene)". Organic Syntheses. CS1 maint: Multiple names: authors list (link) ; Collective Volume, 1, p. 440
Jump up ^ R. Fittig und F. Binder "Ueber die Additionsproducte der Zimmtssaure" in "Untersuchungen über die ungesättigten Säuren. I. Weitere Beiträge zur Kenntnifs der Fumarsäure und Maleïnsäure" Rudolph Fittig, Camille Petri, Justus Liebigs Annalen der Chemie 1879, volume 195, p 56-179. doi:10.1002/jlac.18791950103
Jump up ^ MSDS (1 November 2010). "Material Safety Data Sheet Styrene (monomer) MSDS". MSDS. Archived from the original on 7 August 2011. Retrieved 11 June 2011.
Jump up ^ US EPA (December 1994). "OPPT Chemical Fact Sheets (Styrene) Fact Sheet: Support Document (CAS No. 100-42-5)" (PDF). US EPA. Archived (PDF) from the original on 24 December 2010. Retrieved 11 June 2011.
Jump up ^ "Archived copy" (PDF). Archived (PDF) from the original on 2 June 2008. Retrieved 6 April 2008.
Jump up ^ Kenneth C. Liebman (1975). "Metabolism and toxicity of styrene" (PDF). Environmental Health Perspectives. 11: 115–119. doi:10.2307/3428333. JSTOR 3428333.
Jump up ^ "EPA settles case against Phoenix company for toxic chemical reporting violations". U.S. Environmental Protection Agency. Archived from the original on 25 September 2008. Retrieved 11 February 2008.
Jump up ^ "EPA Fines California Hot Tub Manufacturer for Toxic Chemical Release Reporting Violations". U.S. Environmental Protection Agency. Archived from the original on 25 September 2008. Retrieved 11 February 2008.
Jump up ^ Harris, Gardiner (10 June 2011). "Government Says 2 Common Materials Pose Risk of Cancer". New York Times. Archived from the original on 13 June 2011. Retrieved 11 June 2011.
Jump up ^ National Toxicology Program (10 June 2011). "12th Report on Carcinogens". National Toxicology Program. Archived from the original on 12 June 2011. Retrieved 11 June 2011.
Jump up ^ "Archived copy". Archived from the original on 9 June 2012. Retrieved 24 September 2012.
Jump up ^ Boffetta, P., et al., Epidemiologic Studies of Styrene and Cancer: A Review of the Literature Archived 9 October 2012 at the Wayback Machine., J. Occupational and Environmental Medicine, Nov.2009, V.51, N.11.
Jump up ^ Kolstad, HA; Juel K; Olsen J; Lynge E. (May 1995). "Exposure to styrene and chronic health effects: mortality and incidence of solid cancers in the Danish reinforced plastics industry". Occupational and Environmental Medicine. 52 (5): 5. doi:10.1136/oem.52.5.320. PMC 1128224  . PMID 7795754.
Jump up ^ Danish EPA 2011 review "Archived copy" (PDF). Archived (PDF) from the original on 14 July 2014. Retrieved 15 February 2012.
Jump up ^ "Archived copy". Archived from the original on 12 May 2009. Retrieved 18 October 2009. US environmental protection agency. Section I.B.4 relates to neurotoxicology.
Jump up ^ "EPA IRIS track styrene page". epa.gov. Archived from the original on 22 December 2011. Retrieved 1 May 2018.
Jump up ^ "Styrene entry in National Toxicology Program's Thirteenth Report on Carcinogens" (PDF). nih.gov. Archived (PDF) from the original on 22 October 2017. Retrieved 1 May 2018.
Jump up ^ "Some Traditional Herbal Medicines, Some Mycotoxins, Naphthalene, and Styrene - WHO - OMS -". apps.who.int. Archived from the original on 23 September 2011. Retrieved 1 May 2018.
External links[edit]
CDC - Styrene - NIOSH Workplace Safety and Health Topic
Safety and Health Topics | Styrene (OSHA)
OSHA-NIOSH 2018. Preventing Hearing Loss Caused by Chemical (Ototoxicity) and Noise Exposure Safety and Health Information Bulletin (SHIB), Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health. SHIB 03-08-2018. DHHS (NIOSH) Publication No. 2018-124.
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