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Hydrocarbon chemistry transforms a century, and still going

Natural gas and non-traditional polymer feedstocks are an opportunity for plastics innovation.


Honeywell UOP’s Oleflex process converts isobutane into isobutylene. Courtesy: Honeywell UOPIn March, four Honeywell UOP scientists received the American Institute of Chemical Engineers' (AIChE) 2016 industrial research & development award, fuels and petrochemical division. The award recognized development and commercialization of a methanol-to-olefins (MTO) process the four helped develop as part of a team at Honeywell UOP, a company which-under various guises—has for more than a century played a significant part in the oil & gas industry.

Moreover, the company, for the oil & gas industry, is headquartered in an unlikely location: Des Plaines, Ill., just outside of Chicago. Chicago meat-packer J. Ogden Amour created the National Hydrocarbon Co. in 1914 to commercialize 12 inventions held by Jesse Adams Dubbs, a kind of serial entrepreneur of his day. What was National Hydrocarbon at that time is Honeywell UOP today.

One of Dubb's inventions led to a process to demulsify oil, to yield heavier fuel oil and asphalt. A byproduct was gasoline—at a yield four times greater than conventional refining methods. Until then, gasoline had been used as a solvent. With gasoline finding favor in internal combustion engines, however, it led to commercialization of the first conversion technology for upgrading crude oil. 

Present and future

Honeywell UOP technology still plays a role in refineries and chemical plants around the world. The MTO process recognized by AIChE converts methanol from non-petroleum feedstocks such as coal, methane, petroleum coke, or biomass-instead of petroleum-into polymer-grade ethylene and propylene. It's a big deal because the plastics derived from ethylene and propylene are among the most widely produced synthetic polymers, used the world over in the manufacture of a wide range of packaging and goods.

MTO development began in the 1980s, when Honeywell UOP applied an innovative molecular sieve to its chemistry. It culminated in 1995 with the first MTO demonstration unit, operated by Norsk Hydro, now part of Inovyn.

Not long after, Honeywell UOP and Atofina, now part of Total, developed the olefin-cracking process (OCP) that converts heavier MTO-process olefin byproducts into lighter olefins. Together they make the advanced MTO process, covered by more than 50 patents, and licensed to nine customers.

In February, Jiangsu Sailboat Petrochemical Co., Ltd. started its MTO unit during a 10-day test. The full on-line unit will have an annual production capacity of 833,000 metric tons per year, making it the largest single-train MTO unit in the world (see figure 1).

The Sailboat facility will produce propylene for making acrylonitrile, used to make clothing and fabrics, and high-performance polymers used in automotive parts, hard hats, and other hard-plastic products. The plant also will produce ethylene for ethylene vinyl acetate copolymers, used to make adhesives, foams, medical devices, and photovoltaic cells, as well as C4 olefins for production of butadiene, an ingredient in synthetic rubber. 

Rising market

While the oil & gas industry has been in a two-year slump, low prices for natural gas in the U.S. and for oil internationally has caused a chemical-industry boom. In the U.S. alone, 264 new projects and more than $161 billion in investment projects have been announced since 2010, according to Transporting Growth: delivering a chemical manufacturing renaissance, a March report from PwC on behalf of the American Chemistry Council (ACC).

In the U.S., natural gas is used to make plastic. For plastics industries, low-cost, abundant shale gas is an affordable feedstock and energy source. By contrast, in most other parts of the world, oil is used in making plastics.

This historical anomaly bodes well for North American resins producers who anticipate strong demand here in the U.S. and internationally, according to an April outlook report from ACC on North American resins production and sales in 2016.

In the U.S., with nearly half of the announced investment since 2010 completed or under development, shale gas and increasing supplies of natural-gas liquids secure a competitive advantage for U.S. chemical and polymer resins producers.

As capacity expands, North American net-resin exports have potential to rise dramatically. They already bolster the sector's trade surplus. A stronger U.S. economy and key end-use markets will increase domestic resin consumption. However, continuing market access and global supply chains, rather than contractions or disruptions will be essential to North American resins producers' ability to exploit their competitive advantage, say the ACC report authors. 

Once fully on-line, the MTO unit at Jiangsu Sailboat Petrochemical Co., Ltd. will have an annual production capacity of 833,000 metric tons of propylene per year. Courtesy: Honeywell UOPHere in the U.S.

In February, Houston-based Enterprise Products Operating LLC chose Honeywell UOP's C4 Oleflex technology to produce 425,000 metric tons per year of isobutylene, used to make high-octane fuel and high-performance synthetic rubbers and acrylics (see figure 2).

C4 Oleflex technology uses catalytic dehydrogenation to convert isobutane into isobutylene, with comparatively low production costs and high return on investment. A platinum-alumina-based catalyst system minimizes environmental impact. The process maximizes operating flexibility, on-stream factor, and reliability, Honeywell said.

C3 Oleflex uses catalytic dehydrogenation to convert propane to propylene.

Enterprise Products supplies midstream energy services to producers and consumers of natural gas, natural gas liquids (NGLs), crude oil, petrochemicals, and refined products.

In addition to technology licensing, Honeywell UOP will do the basic engineering design, control systems, catalysts, and adsorbents for the plant located in Mont Belvieu, Texas. It also will supply a modular continuous catalyst regeneration (CCR) unit. Because modular CCR units are factory built, start-up on site is faster and the units easier to operate due to common parts and standardized training, operations, and maintenance.

"High demand from automotive, industrial-machinery, and construction applications are expected to drive growth in lubricant production. At the same time, demand for high-octane fuel is rising based on higher fuel-economy standards," said Mike Millard, a Honeywell vice president and general manager.

In Europe, demand for propylene continues to rise at the same time the supply from refineries and steam crackers is slowing. Honeywell UOP says Oleflex is an on-purpose, reliable route to fill propylene supply gaps and support derivative production in Europe.

Borealis AG selected UOP technology for a proposed plant in Kallo, Belgium, that converts propane into propylene. Borealis proposes to use C3 Oleflex technology to produce a targeted 740,000 metric tons per year of polymer-grade propylene. When completed, it will be UOP's third C3 Oleflex unit-and the largest-in Europe.

As a previous case mentioned, besides licensing, Honeywell UOP is providing the basic engineering design as well as services, equipment, catalysts, and adsorbents.

Borealis is a provider of polyolefins, base chemicals, and fertilizers, with headquarters in Vienna, Austria. A feasibility study for the Kallo plant is under way, with final investment decision expected in the third quarter of 2018 and potential start-up of the plant in the second half of 2021.

In all, Oleflex has been selected for 39 projects by 46 producers globally since 2011, including propane (C3), isobutane (iC4) and mixed C3/iC4 service. Honeywell UOP has commissioned 27 Oleflex units for on-purpose propylene and isobutylene production. Five more units in China and the Middle East are expected to start up later this year.

Clockwise from top left, John Senetar led modeling and design; Paul Barger established catalyst and process criteria; Dan Kauff led the integration of MTO and OCP processes; and John Chen led the team. Courtesy: Honeywell UOPNot just innovative; it's also important

Presenting the American Institute of Chemical Engineers (AIChE) 2016 industrial research & development award, fuels and petrochemical division, to four Honeywell UOP scientists (see figure 3) recognizes a technology that converts methanol from sources such as coal and natural gas into the olefins that are the primary components in the manufacture of plastic resins, films and fibers.

This is especially critical in countries that lack domestic sources of crude oil but are rich in coal or natural gas.

"The development of this technology over many years is a point of great pride within Honeywell UOP, culminating in its commercialization in 2013, with nine customers since that time," said Jim Rekoske, VP and chief technology officer at Honeywell UOP.

While many engineers and scientists contributed to the development of the Advanced MTO process, the AIChE recognized that John Chen led the research team; John Senetar led modeling and process design; Paul Barger established the catalyst and process criteria; and Dan Kauff led the integration of MTO and OCP processes.

Company history includes convolutions

Having been established as the National Hydrocarbon Co. in 1914, UOP in 1919 changed its name to Universal Oil Products and unveiled a new refining method. It licensed the technology to refineries for a royalty fee based on production. Beginning in 1922 it began signing licensees all over the world.

In 1931, a consortium of companies purchased UOP. Members included names of great historical interest to the oil & gas industry, including Shell, Texaco, ARCO, Gulf Oil, and elements of the by-then-broken-up Standard Oil Co. UOP, in effect, became the center of research for the oil & gas industry.

Also in 1931, Vladimir Ipatieff, a world-class chemist, joined UOP, which from then on has had a reputation for attracting top talent.

In 1933, Ipatieff introduced solid phosphoric acid as a catalyst to stimulate higher yields of gasoline.

In 1944, the oil companies that owned UOP placed it in a trust to support the American Chemical Society.

In 1947, the use of platinum as a reforming agent led to a new method of catalysis and became the world's leading process for making gasoline. This and other UOP technologies were key to development of the petrochemicals industry in the 1950s.

UOP was sold to shareholders in a 1959 public offering.

In the 1970s, UOP was involved in the introduction of lead-free gasolines. By 1979, Signal Corp. owned 100% of UOP. Signal merged with Allied Chemical Corp. in 1979, making UOP part AlliedSignal's engineered materials division. Soon the company was co-owned by AlliedSignal and Dow Chemical Corp. In 1999, AlliedSignal bought Honeywell, and Dow bought Union Carbide, which meant UOP was jointly-owned by Honeywell and Dow.

In 2005, Honeywell announced that UOP was a wholly-owned subsidiary. Today, UOP has more than 5,000 employees working in 30 plants and offices in six countries.

Kevin Parker, senior contributing editor, Oil & Gas Engineering, CFE Media, kparker@cfemedia.com.

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