Editing Petrochemical

{{Short description|Chemical product derived from petroleum}}
[[File:TASNEE 001.jpg|thumb|upright=1.35|Petrochemical plant in [[Saudi Arabia]]]]

'''Petrochemicals''' (sometimes abbreviated as '''petchems'''<ref>Kiesche, Liz, [https://seekingalpha.com/news/3604684-royal-dutch-shell-may-take-50-stake-in-9b-indian-petchem-project-reuters "Royal Dutch Shell may take 50% stake in $9B Indian petchem project"], [[Reuters]] via ''[[Seeking Alpha]]'', August 12, 2020. Retrieved 2020-08-12.</ref>) are the [[product (chemistry)|chemical products]] obtained from [[petroleum]] by refining. Some [[chemical compound]]s made from petroleum are also obtained from other [[fossil fuel]]s, such as [[coal]] or [[natural gas]], or renewable sources such as [[maize]], [[Elaeis|palm fruit]] or [[sugar cane]].

The two most common petrochemical classes are [[alkene|olefins]] (including [[ethylene]] and [[propylene]]) and [[aromaticity|aromatics]] (including [[benzene]], [[toluene]] and [[xylene]] [[isomers]]).

[[Oil refinery|Oil refineries]] produce olefins and aromatics by [[fluid catalytic cracking]] of petroleum fractions. [[Chemical plant]]s produce olefins by [[steam cracking]] of [[natural gas liquids]] like [[ethane]] and [[propane]]. Aromatics are produced by [[catalytic reforming]] of [[Petroleum naphtha|naphtha]]. Olefins and aromatics are the building-blocks for a wide range of materials such as [[solvent]]s, [[detergent]]s, and [[adhesive]]s. Olefins are the basis for [[polymer]]s and [[oligomer]]s used in [[plastic]]s, [[resin]]s, [[fiber]]s, [[elastomer]]s, [[lubricant]]s, and [[gels]].<ref name="Hatch">{{cite book|author=Sami Matar and Lewis F. Hatch|title=Chemistry of Petrochemical Processes|publisher=Gulf Professional Publishing|year=2001|isbn=0-88415-315-0}}</ref><ref name="HP">{{cite journal|author=Staff |date=March 2001|title=Petrochemical Processes 2001 |journal=Hydrocarbon Processing |pages=71–246 |issn=0887-0284}}</ref>

Global ethylene production was 190 million tonnes and propylene was 120 million tonnes in 2019.<ref>{{Cite web|url=https://www.statista.com/statistics/1067372/global-ethylene-production-capacity/#:~:text=The%20production%20capacity%20of%20ubiquitous,to%20283%20million%20metric%20tons.|title = Ethylene production capacity globally 2024}}</ref> Aromatics production is approximately 70 million tonnes. The largest [[petrochemical industries]] are located in the [[United States]] and [[Western Europe]]; however, major growth in new production capacity is in the [[Middle East]] and [[Asia]]. There is substantial inter-regional petrochemical trade.

Primary petrochemicals are divided into three groups depending on their [[chemical structure]]:

* [[Alkene|Olefins]] includes [[Ethylene|ethene]], [[propene]], [[butene]]s and [[1,3-Butadiene|butadiene]]. Ethylene and propylene are important sources of [[industrial chemicals]] and [[plastics]] [[Product (business)|products]]. Butadiene is used in making [[synthetic rubber]].
* [[Aromatics]] includes [[benzene]], [[toluene]] and [[xylene]]s, as a whole referred to as [[BTX (chemistry)|BTX]] and primarily obtained from petroleum refineries by extraction from the reformate produced in [[Catalytic reforming|catalytic reformers]] using [[Petroleum naphtha|naphtha]] obtained from petroleum refineries. Alternatively, BTX can be produced by aromatization of alkanes. Benzene is a raw material for [[dyes]] and synthetic detergents, and benzene and toluene for [[isocyanate]]s [[Methylene diphenyl diisocyanate|MDI]] and [[Toluene diisocyanate|TDI]] used in making [[polyurethanes]]. Manufacturers use [[xylene]]s to produce plastics and synthetic fibers.
* [[Synthesis gas]] is a [[mixture]] of [[carbon monoxide]] and [[hydrogen]] used to produce [[methanol]] and other chemicals. [[Steam cracking|Steam crackers]] are not to be confused with [[steam reforming]] plants used to produce [[hydrogen]] for [[Ammonia production|ammonia]] production. Ammonia is used to make the [[fertilizer]] [[urea]] and methanol is used as a solvent and [[chemical]] intermediate. 
* [[Methane]], [[ethane]], [[propane]] and [[butane]]s obtained primarily from [[Natural gas processing|natural gas processing plants]].
* [[Methanol]] and [[formaldehyde]].

In 2007, the amounts of ethylene and propylene produced in steam crackers were about 115 M[[Tonne|t]] (megatonnes) and 70 Mt, respectively.<ref>{{cite book|title=Proceedings of the 1st Annual Gas Processing Symposium, Volume 1: January, 2009 – Qatar |editor1=Hassan E. Alfadala |editor2=G.V. Rex Reklaitis |editor3=Mahmoud M. El-Halwagi |publisher=Elsevier Science|year=2009|isbn=978-0-444-53292-3|edition=1st|pages=402–414}}</ref> The output ethylene capacity of large steam crackers ranged up to as much as 1.0 – 1.5 Mt per year.<ref>[http://www.technip.com/pdf/brochures/Ethylene.pdf Steam Cracking: Ethylene Production]{{Dead link|date=October 2024 |bot=InternetArchiveBot |fix-attempted=yes }} (PDF page 3 of 12 pages)</ref>

The adjacent diagram schematically depicts the major hydrocarbon sources and processes used in producing petrochemicals.<ref name="Hatch" /><ref name="HP" /><ref name="AMAP">[http://www.tsp2.org/news/Butadiene%20Supply%20AMAP%20Update.pdf SBS Polymer Supply Outlook]</ref><ref>{{cite book|title=Petroleum Refining: Refinery Operation and Management|editor=Jean-Pierre Favennec |publisher=Editions Technip|year=2001|isbn=2-7108-0801-3}}</ref>[[File:Petrochem Feedstocks.png|thumb|right|upright=1.95|Petrochemical feedstock sources]]

Like [[commodity chemicals]], petrochemicals are made on a very large scale. Petrochemical manufacturing units differ from commodity chemical plants in that they often produce a number of related products. Compare this with [[Specialty chemical industry|specialty chemical]] and [[fine chemical]] manufacture where products are made in discrete batch processes.

Petrochemicals are predominantly made in a few manufacturing locations around the world, for example in [[Jubail]] and [[Yanbu]] Industrial Cities in Saudi Arabia, [[Texas]] and [[Louisiana]] in the US, in [[Teesside]] in the [[Northeast of England]] in the [[United Kingdom]], in [[Tarragona]] in [[Catalonia]], in [[Rotterdam]] in the Netherlands, in [[Antwerp]] in [[Belgium]], in [[Jamnagar Refinery|Jamnagar]], [[Dahej]] in [[Gujarat]], [[India]] and in Singapore. Not all of the petrochemical or commodity chemical materials produced by the chemical industry are made in one single location but groups of related materials are often made in adjacent manufacturing plants to induce industrial symbiosis as well as material and utility efficiency and other [[economies of scale]]. This is known in [[chemical engineering]] terminology as integrated manufacturing. Specialty and fine chemical companies are sometimes found in similar manufacturing locations as petrochemicals but, in most cases, they do not need the same level of large-scale infrastructure (e.g., pipelines, storage, ports, and power, etc.) and therefore can be found in multi-sector business parks.

The large-scale petrochemical manufacturing locations have clusters of manufacturing units that share utilities and large-scale infrastructures such as power stations, storage tanks, port facilities, road and rail terminals. In the United Kingdom, for example, there are four main locations for such manufacturing: near the River Mersey in North West England, on the Humber on the East coast of Yorkshire, in Grangemouth near the Firth of Forth in Scotland, and in Teesside as part of the [[Northeast of England Process Industry Cluster]] (NEPIC). To demonstrate the clustering and integration, some 50% of the United Kingdom's petrochemical and commodity chemicals are produced by the NEPIC industry cluster companies in Teesside.

== History ==
In 1835, [[Henri Victor Regnault]], a French chemist left [[vinyl chloride]] in the sun and found white solid at the bottom of the flask which was [[polyvinyl chloride]]. In 1839, [[Eduard Simon]] discovered polystyrene by accident by distilling [[Storax balsam|storax]]. In 1856, [[William Henry Perkin]] discovered the first synthetic dye, [[Mauveine]]. In 1888, [[Friedrich Reinitzer]], an Austrian plant scientist observed [[cholesteryl benzoate]] had two different melting points. In 1909, [[Leo Baekeland|Leo Hendrik Baekeland]] invented [[bakelite]] made from [[phenol]] and [[formaldehyde]]. In 1920, [[Union Carbide]] built in [[West Virginia]] first petrochemical plant in the world.<ref>Alec Ross, '[[The Industries of the Future]], Simon&Schuster, 2016, pp. 7-8</ref> In 1928, [[synthetic fuel]]s were invented using [[Fischer–Tropsch process|Fischer-Tropsch process]]. In 1929, [[Walter Bock]] invented synthetic rubber [[Buna-S]] which is made up of [[styrene]] and [[1,3-Butadiene|butadiene]] and used to make car tires. In 1933, [[Otto Röhm]] polymerized the first acrylic glass [[methyl methacrylate]]. In 1935, [[Michael Perrin]] invented [[polyethylene]]. In 1937, [[Wallace Carothers|Wallace Hume Carothers]] invented [[nylon]]. In 1938, [[Otto Bayer]] invented [[polyurethane]]. In 1941, [[Roy J. Plunkett|Roy Plunkett]] invented [[Teflon]]. In 1946, he invented [[Polyester]]. [[Polyethylene terephthalate]] (PET) bottles are made from [[ethylene]] and [[P-Xylene|paraxylene]]. In 1949, Fritz Stastny turned [[polystyrene]] into foam. After World War II, [[polypropylene]] was discovered in the early 1950s. In 1965, [[Stephanie Kwolek]] invented [[Kevlar]].<ref>{{Cite web|url=https://www.petrochemistry.eu/about-petrochemistry/timeline/|title=Timeline – Petrochemicals Europe|website=www.petrochemistry.eu|language=en-US|access-date=2018-04-07}}</ref>

== Olefins ==

The following is a partial list of major commercial petrochemicals and their derivatives:
[[File:Petrochem1.png|thumb|upright=2.2|Chemicals produced from ethylene]]
* [[ethylene]] – the simplest olefin; used as a chemical feedstock and ripening stimulant
**[[polyethylene]] – [[Polymerization|polymerized]] ethylene; [[Low-density polyethylene|LDPE]], [[High-density polyethylene|HDPE]], [[Linear low-density polyethylene|LLDPE]]
**[[ethanol]] – via ethylene [[Hydration reaction|hydration]] ([[chemical reaction]] adding [[water]]) of ethylene
** [[ethylene oxide]] – via ethylene [[oxidation]]
*** [[ethylene glycol]] – via ethylene oxide hydration
**** [[antifreeze (coolant)|engine coolant]] – ethylene glycol, water and inhibitor mixture
**** [[polyester]]s – any of several polymers with ester linkages in the main chain
*** [[glycol ether]]s – via glycol condescension
*** [[Narrow range ethoxylate|ethoxylates]]
** [[vinyl acetate]]<ref>{{Cite journal|last1=Han|first1=Y. -F.|last2=Wang|first2=J. -H.|last3=Kumar|first3=D.|last4=Yan|first4=Z.|last5=Goodman|first5=D. W.|date=2005-06-10|title=A kinetic study of vinyl acetate synthesis over Pd-based catalysts: kinetics of vinyl acetate synthesis over Pd–Au/SiO2 and Pd/SiO2 catalysts|url=http://www.sciencedirect.com/science/article/pii/S0021951705001405|journal=Journal of Catalysis|language=en|volume=232|issue=2|pages=467–475|doi=10.1016/j.jcat.2005.04.001|issn=0021-9517|url-access=subscription}}</ref>
** [[1,2-Dichloroethane|1,2-dichloroethane]]
*** [[trichloroethylene]]
*** [[tetrachloroethylene]] – also called perchloroethylene; used as a dry cleaning solvent and degreaser
*** [[vinyl chloride]] – monomer for [[polyvinyl chloride]]
**** [[polyvinyl chloride]] (PVC) – a type of plastic used for piping, tubing, other things
[[File:Petrochem3.png|thumb|upright=2|Chemicals produced from propylene]]
* [[propylene]] – used as a monomer and a chemical feedstock
**[[isopropyl alcohol]] – 2-propanol; often used as a solvent or rubbing alcohol
** [[acrylonitrile]] – useful as a monomer in forming [[Orlon]], [[Acrylonitrile butadiene styrene|ABS]]
** [[polypropylene]] – [[Polymerization|polymerized]] propylene
** [[propylene oxide]]<ref>{{Cite journal|last1=Lee|first1=Eo Jin|last2=Lee|first2=Jong Won|last3=Lee|first3=Joongwon|last4=Min|first4=Hyung-Ki|last5=Yi|first5=Jongheop|last6=Song|first6=In Kyu|last7=Kim|first7=Do Heui|date=2018-06-01|title=Ag-(Mo-W)/ZrO2 catalysts for the production of propylene oxide: Effect of pH in the preparation of ZrO2 support|url=http://www.sciencedirect.com/science/article/pii/S1566736718301353|journal=Catalysis Communications|language=en|volume=111|pages=80–83|doi=10.1016/j.catcom.2018.04.005|s2cid=103189174|issn=1566-7367|url-access=subscription}}</ref>
***polyether polyol – used in the production of polyurethanes
***[[propylene glycol]] – used in engine coolant <ref>{{Cite patent|country=HU|number=209546B|title=Anti-freeze solution for internal combustion engines|status=patent|pubdate=1994-07-28|fdate=1990-11-12|invent1=Forstner|invent2=Gal|invent3=Feher|invent4=Berkes|inventor1-first=Janos|inventor2-first=Lajos|inventor3-first=Pal|inventor4-first=Tiborne}}</ref> and aircraft deicer fluid
***[[glycol ether]]s – from the condensation of glycols
** [[acrylic acid]]
***[[acrylic polymer]]s
** [[allyl chloride]]
*** [[epichlorohydrin]] – chloro-oxirane; used in epoxy resin formation
**** [[epoxy resin]]s – a type of polymerizing glue from bisphenol A, epichlorohydrin, and some [[amine]]
*[[butene]]
** [[isomers of butylene]] – useful as monomers or co-monomers
*** [[isobutylene]] – feed for making [[Methyl tert-butyl ether|methyl ''tert''-butyl ether]] (MTBE) or monomer for copolymerization with a low percentage of [[isoprene]] to make [[butyl rubber]]
** [[1,3-butadiene]] (or buta-1,3-diene) – a [[diene]] often used as a monomer or co-monomer for polymerization to [[elastomer]]s such as [[polybutadiene]], [[styrene-butadiene rubber]], or a plastic such as [[acrylonitrile-butadiene-styrene]] (ABS)
*** [[synthetic rubber]]s – synthetic elastomers made of any one or more of several petrochemical (usually) monomers such as 1,3-[[butadiene]], [[styrene]], [[isobutylene]], [[isoprene]], [[chloroprene]]; elastomeric polymers are often made with a high percentage of conjugated diene monomers such as 1,3-butadiene, isoprene, or chloroprene
* higher olefins
**[[polyolefin]]s – such poly-alpha-olefins, which are used as lubricants
** [[alpha-olefin]]s – used as monomers, co-monomers, and other chemical precursors.  For example, a small amount of [[1-hexene]] can be copolymerized with ethylene into a more flexible form of polyethylene.
** other higher olefins
** detergent alcohols

== Aromatics ==
{{Main|BTX (chemistry)}}
[[File:Petrochem2.png|thumb|upright=2.65|Chemicals produced from benzene]]
*[[benzene]] – the simplest aromatic hydrocarbon
**[[ethylbenzene]] – made from benzene and ethylene
*** [[styrene]] – made by dehydrogenation of ethylbenzene; used as a monomer
**** [[polystyrene]]s – polymers with styrene as a monomer
** [[cumene]] – isopropylbenzene; a feedstock in the [[cumene process]]
*** [[phenol]] – hydroxybenzene; often made by the cumene process
*** [[acetone]] – dimethyl ketone; also often made by the cumene process
*** [[bisphenol A]] – a type of "double" phenol used in polymerization in epoxy resins and making a common type of polycarbonate
**** [[epoxy resin]]s – a type of polymerizing glue from bisphenol A, epichlorohydrin, and some [[amine]]
**** [[polycarbonate]] – a plastic polymer made from bisphenol A and [[phosgene]] (carbonyl dichloride)
*** [[solvents]] – liquids used for dissolving materials; examples often made from petrochemicals include ethanol, isopropyl alcohol, acetone, benzene, toluene, xylenes
** [[cyclohexane]] – a 6-carbon aliphatic cyclic hydrocarbon sometimes used as a non-polar solvent
*** [[adipic acid]] – a 6-carbon di[[carboxylic acid]], which can be a precursor used as a co-monomer together with a di[[amine]] to form an alternating copolymer form of nylon.
**** [[nylon]]s – types of [[polyamide]]s, some are alternating copolymers formed from copolymerizing [[dicarboxylic acid]] or derivatives with diamines
*** [[caprolactam]] – a 6-carbon cyclic [[amide]]
**** [[nylon]]s – types of [[polyamide]]s, some are from polymerizing caprolactam
** [[nitrobenzene]] – can be made by single nitration of benzene
*** [[aniline]] – aminobenzene
**** [[methylene diphenyl diisocyanate]] (MDI) – used as a co-monomer with [[diol]]s or polyols to form [[polyurethanes]] or with di- or poly[[amine]]s to form [[polyurea]]s
** [[alkylbenzene]] – a general type of aromatic hydrocarbon, which can be used as a precursor for a [[sulfonate]] [[surfactant]] (detergent)
***[[detergent]]s – often include [[surfactant]]s types such as alkylbenzene sulfonates and nonylphenol ethoxylates
** [[chlorobenzene]]
[[File:Petrochem4.png|thumb|upright=1.6|Chemicals produced from toluene]]
* [[toluene]] – methylbenzene; can be a solvent or precursor for other chemicals
** [[benzene]]
** [[toluene diisocyanate]] (TDI) – used as co-monomers with polyether polyols to form polyurethanes or with di- or poly[[amine]]s to form [[polyurea]]s [[polyurethane]]s
** [[benzoic acid]] – carboxybenzene
*** [[caprolactam]]
[[File:Petrochem5.png|thumb|upright=1.8|Chemicals produced from xylenes]]
* [[xylene|mixed xylenes]] – any of three dimethylbenzene isomers, could be a solvent but more often precursor chemicals
** [[O-Xylene|''ortho''-xylene]] – both [[methyl group]]s can be oxidized to form (''ortho-'')phthalic acid
*** [[phthalic anhydride]]
** [[P-Xylene|''para''-xylene]] – both methyl groups can be oxidized to form terephthalic acid
*** [[dimethyl terephthalate]] – can be copolymerized to form certain polyesters
**** [[polyester]]s – although there can be many types, [[polyethylene terephthalate]] is made from petrochemical products and is very widely used in petrol stations 
*** purified [[terephthalic acid]] – often copolymerized to form [[polyethylene terephthalate]]
**** [[polyester]]s
** [[M-Xylene|''meta''-xylene]]
*** [[isophthalic acid]]
**** [[Alkyd|alkyd resins]]
**** [[Polyamide-imide|polyamide resins]]
**** [[Polyester resin|unsaturated polyesters]]

==List of petrochemicals==

{| class="wikitable" style="width:678pt;" 
|-
! Petrochemicals
! Fibers
! Petroleum
! Chemicals
|-
| style="text-align:center;"|'''Basic Feedstock'''<br>[[Benzene]]<br>[[Butadiene]]<br>[[Ethylene]]<br>[[P-Xylene|''p''-Xylene]]<br>[[Propylene]]
'''Intermediates'''<br>[[2-Ethylhexanol]] (2-EH)<br>[[Acetic acid]]<br>[[Acrylonitrile]] (AN)<br>[[Ammonia]]<br>[[Bis(2-ethylhexyl) phthalate]] (dioctyl phthalate)<br>n-[[Butene]]<br>[[Cyclohexane]]<br>[[Dimethyl terephthalate]] (DMT)<br> [[Dodecylbenzene]]<br>[[Ethanol]]<br>[[Ethanolamine]]<br>Ethoxylate<br>[[1,2-Dichloroethane]] (ethylene dichloride or EDC)<br>[[Ethylene glycol]] (EG)<br>[[Ethylene oxide]] (EO)<br>Formaldehyde Moulding Compound (FMC)<br>n-[[Hexene]]<br>[[Linear alkyl benzene]] (LAB)<br>[[Methanol]]<br>[[Methyl tert-butyl ether]] (MTBE) <br>[[Phenol]]<br>[[Propylene oxide]]<br>Purified [[terephthalic acid]] (PTA)<br>[[Styrene]] [[monomer]] (SM)<br>Thermosetting Resin (Urea/Melamine)<br>[[Vinyl acetate monomer]] (VAM)<br>[[Vinyl chloride monomer]] (VCM)

| style="text-align:center;"| [[Acrylic fiber]]<br>[[Acrylonitrile butadiene styrene]] (ABS)<br>Acrylonitrile styrene (AS)<br>[[Polybutadiene]] (PBR)<br>[[Polyvinyl chloride]] (PVC)<br>[[Polyethylene]] (PE) <br>[[Polyethylene terephthalate]] (PET)<br>[[Polyol]]<br>[[Polypropylene]] (PP)<br>[[Polystyrene]] (PS)<br>[[Styrene]] [[1,3-Butadiene|butadiene]] (SBR)<br>Acrylic-formaldehude (AF)

| style="text-align:center;"|[[Lubricant]]s<br>[[Oil additive|Additives]]<br>[[Catalyst]]s<br> [[ISO 8217|Marine fuel oil]]<br>[[Petroleum refining]]

| style="text-align:center;"|[[Adhesive]]s and [[sealant]]s<br>[[Agrochemical]]s<br>[[Construction]] chemicals<br>[[Corrosion]] control chemicals<br>[[Cosmetics]] raw materials<br>[[Electronics|Electronic]] chemicals and materials<br>[[Flavouring]]s, [[fragrance]]s, [[food additive]]s<br>[[Pharmaceutical drugs]]<br>Specialty and [[Chemical industry|industrial chemicals]]<br>Specialty and [[industrial gas]]es<br>[[Ink]]s, [[dye]]s and [[printing]] supplies<br>[[Packaging]], [[bottle]]s, and containers<br>[[Paint]], [[coating]]s, and [[resin]]s<br> [[Polymer]] additives<br>Specialty and [[life sciences]] chemicals<br>[[Surfactant]]s and [[cleaning agent]]s

|}

==See also==
*{{annotated link|Petroleum}}
*{{annotated link|Petroleum product}}
*{{annotated link|Petrodollar}}
*{{annotated link|Petrostate}}
*{{annotated link|Instrumentation in petrochemical industries}}
*{{annotated link|Organization of the Petroleum Exporting Countries}}
*{{annotated link|Asia Petrochemical Industry Conference}} (APIC)
*{{annotated link|Northeast of England Process Industry Cluster}} (NEPIC)

==References==
{{Reflist|30em}}

==External links==
{{Commons category|Petrochemicals}}{{Branches of chemistry}}{{authority control}}

[[Category:Petrochemicals| ]]
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