Licensing

CUMENE TECHNOLOGY HIGHLIGHTS
Versalis is in the position to offer on the market one of the best and reliable zeolite-based technology for industrial Cumene production suitable for both grass-root plant and revamping of existing units still based on traditional SKPA technology where an extracapacity up to 80 % in the same reaction section can be easily reached.

Main process features of Versalis Cumene with proprietary catalyst PBE-1 zeolite-based are:

• Cumene product purity higher than 99.9% wt
• no clay treaters for finished Cumene, thanks to a negligible Bromine Index
• high performances in distillation section leading to lower variable costs and lower benzene recycle ratio
• high process efficiency due to unrivalled high selectivities to Cumene in both Alkylation and transalkylation stages, over a wide range of benzene to propylene ratios
• total productivity in excess of 30 MT of Cumene per kg of catalyst at every reaction cycle
• no environmental concerns associated to former SKPA or AlCl3 catalysts; no plant maintenance concerns due to catalyst acid syrups or fine powder production during operation and loading/unloading and no special materials or coatings needed for plant equipments
• long-lasting catalyst fully regenerable through an easy ex-situ regeneration procedure allowing several reaction/regeneration cycles with an unusually high ultimate catalyst lifetime
• PBE-1 zeolite-based proprietary catalyst has been tested with all the possible benzene and propylene feedstock impurities showing a unique, highly proven tolerance.
  Industrial units based on proprietary technology are on-stream in Italy for about 400 kt/y of installed Cumene capacity.

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PHENOL TECHNOLOGY HIGHLIGHTS
Versalis is in the position to offer an advanced technology and know-how suitable for both new phenol plants and revamp of the existing ones based on its wide experience as a primary Phenol producer.
Single plant capacities up to 300 kt/y are fully proven, with overall process efficiency optimized by the use of reactors models for oxidation and cleavage reactions stages and including extractive distillation and tar cracking sections.
Main features of the proprietary Phenol technology are:

• proprietary and intrinsecally safe low-medium pressure oxidation reactor
• proprietary cleavage reactors with very low CHP hold up
• very low raw material consumption
• high Phenol and Acetone purity suitable for BPA - polycarbonate grade applications
• operating experience of more than 40 years as a primary Phenol producer
• relevant synergy with proprietary cumene technology
• industrial units based on proprietary technology are on-stream in Italy and Germany for about 640 kt/y of installed Phenol capacity.

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Over 90% of world's phenol production is currently via cumene hydroperoxide route that produces acetone as a byproduct in a fixed ratio of 0.61 ton of acetone per ton of phenol while market demands for the twos are not in same ratio : new Product Flexibility Solutions are then required. Two technology solutions have been defined:

• Technology solution 1 – Alternate product - Acetone to isopropyl alcohol (IPA)
• Technology solution 2 – Propylene feedstock reduction - Acetone Recycle to cumene

Acetone to IPA process is based on hydrogenation of acetone carried out in a fixed bed catalytic reactor. Reactor effluents are cooled and separated. Hydrogen rich vapor and a portion of raw IPA is recycled to the hydrogenation reactor while the remaining raw IPA enters the first Vacuum Distillation Column where Light Ends, water and Acetone are separated from dry IPA to be further purified. Second Vacuum Distillation Column provides the purified IPA product as column distillate while heavy ends are removed from the column bottoms.
Pilot plant development of both stages of Acetone hydrogenation to produce IPA and Benzene alkylation with IPA to produce cumene have been performed by Versalis while commercial scale process scheme has been developed jointly by Polimeri and Lummus.
Commercial catalyst is used in the hydrogenation reactor. Based on pilot plant results, a 3 years catalyst lifetime is expected.

Over 90% of world's phenol production is currently via cumene hydroperoxide route that produces acetone as a byproduct in a fixed ratio of 0.61 ton of acetone per ton of phenol while market demands for the twos are not in same ratio : new Product Flexibility Solutions are then required. Two technology solutions have been defined:

• Technology solution 1 – Alternate product - Acetone to isopropyl alcohol (IPA)
• Technology solution 2 – Propylene feedstock reduction - Acetone Recycle to cumene

The process is based on benzene alkylation with raw IPA as obtained from acetone hydrogenation stage (see ACETONE HYDROGENATION TECHNOLOGY TO ISOPROPYLALCOHOL avoiding then the purifcation stage to pure IPA. The benzene alkylation with IPA is carried out with a proprietary zeolite based water tolerant catalyst which avoids the separate IPA conversion to propylene step. The water formed during alkylation is then separated from the reactor effluent while the remaining operations are as in the traditional zeolite based process carried out with the propylene as alkylating agent.
Liquid phase alkylation and transalkylation reactors are as in current propylene-based zeolite technology as well as the use of PBE-1 Zeolite-based catalyst. High purity cumene product as in propylene-based zeolite technology. Raw material and utilities consumption comparable to typical propylene-based zeolite technology
Pilot plant development of both stages of Acetone hydrogenation to produce IPA and Benzene alkylation with IPA to produce cumene have been performed by Versalis while commercial scale process scheme has been developed jointly by Polimeri and Lummus.

Versalis, together with Syndial, is in the position to offer the most advanced process and technology to produce cyclohexanone oxime, the key intermediate for the production of Caprolactam and then of Nylon goods.
The process is based on the direct oxidation with ammonia and hydrogen peroxide catalyzed by the proprietary zeolite-based TS-1 catalyst, whose discovery by ENI scientists in the 80's still represents a real breakthrough in the history of heterogeneous catalysis.

The technology is fully proven at industrial scale, with a 75 KTA capacity unit came on stream in 2001, whose produced cyclohexanone oxime has been feeding since then the downstream Caprolactam unit

Main features of the proprietary Ammonoxidation technology based on TS-1 catalyst are:

• Complete avoidance of wastes as well as of salt co-production, still one heavy drawback in the traditional technologies.
• The ammonoxidation reaction is carried out in a watery media and at very mild conditions of temperature and pressure, enabling an unrivalled level of plant safety.
• Unique selectivity to cyclohexanone oxime in the reaction stages, what it keeps easier the purification stages and lower the raw material and utilities variable costs.
• High plant reliability and stability, as well as cyclohexanone oxime quality over time, coupled with the high catalyst lifetime which makes the catalyst cost practically negligible on the total variable costs.

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Versalis non-phosgene production technology route is based on oxidative carbonylation with oxygen, avoiding ammonia processing as well as and unstable intermediates from safety point of view. CO2 by-produced does not represent a Kyoto Protocol infringement as it is totally recycled to CO generation unit, with a consistent feedstock saving.
Main features of Versalis DMC process are:

• environmentally safe process
• high product purity
• low residual content of chlorinated compounds
• integration with CO generation unit allow almost 100% of selectivity to DMC
• unique technology, industrially proven up to 100 kt/y capacity
• technology applied for large capacity policarbonates production
• industrial units based on proprietary technology are on-stream in Japan and Spain for about 100 kt/y of installed DMC capacity.

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Diphenylcarbonate (DPC) is an important intermediate in polycarbonates production which is based on direct or transesterification route. In direct route (interfacial polymerization), the phosgene reacts with bisphenol A (BPA) to yield polycarbonate. The system requires a two phases solvent (water/NaOH and methylene chloride). This route has environmental and corrosion problems; Moreover recovery of chlorine from NaCl is critical.
In transesterification route (melt polymerization) BPA reacts with DPC with formation of polycarbonate and phenol. Compared with the direct route, the transesterification one allows higher productivities, easier polymer processing, and does not need any solvent recovery section.
DPC can be industrially produced according to the following technologies:

• Phosgene route : Phosgene reacts with phenol in presence of NaOH yielding DPC and NaCl. This technology has to manage environmental and coproduction problems of the direct route that can limit plant capacity.
• DMC route : DMC reacts with phenol yielding DPC and methanol. No chlorine is involved in the synthesis and no environmental and corrosion problems have to be faced.

Versalis, owning a high competitive DMC technology, licenses this route. Furthermore the methanol recycle and the possibility of energy integration from DPC to DMC unit create a synergic single one technology.

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Versalis is in the position to offer an up-to-date and flexible Ethylbenzene production technology, based on the proprietary zeolite-based catalysts PBE-1 for alkylation and PBE-2 for transalkylation stages. Technology is reliable and proven at industrial scale with an Ethylbenzene grass root plant of 650 KTA capacity, succesfully started up in 2009 to feed a Styrene downstream plant.
Key features of Versalis technology are :

• High selectivity and excellent stability of PBE-1 and PBE-2 zeolite-based catalysts, along with high design capabilities, always oriented to reliability, safety and great attention to details, based also on Versalis industrial experience as Ethylbenzene and Styrene producer.
• The liquid-phase Versalis Ethylbenzene technology has several advantages over the traditional non-zeolite technologies, expecially over the Aluminium Chloride based technology:
  • low investment and maintenance costs as all equipment in the reaction section are in carbon steel; no need for special alloy or surface lining.
  • Low operating cost due to no need for washing and neutralizing the reactor effluent
  • low environmental impact because no wastewater is generated by the process and spent catalyst, after its long life and several reaction/regeneration cycles is a completely inert material;
  • high selectivity, due to higher performances of the catalyst, resulting in high ethylbenzene purity.

Proprietary Ethylbenzene technology takes advantages from Versalis solid know-how and continuous activities either in process development as well as in zeolite-based catalysis development and production.

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Versalis is in the position to offer a competitive styrene technology which has been developed by taking great advantages of Versalis long experience in both plant design and styrene manufacturing and sales.
As in the present competitive styrene market even small differences in raw materials and utilities specific consumption can heavily influence the profit, the ethylbenzene technology can be furthermore really tailored and customized to site condtions and customer needs.
Styrene technology is reliable and proven at industrial scale, with the first plant come on stream in the early nineties and another plant with a 600 KTA capacity licensed in 2005 and coming on stream within early 2010.

Key features of Proprietary ethylbenzene technology are :

• Low ethylbenzene consumption, high conversion/yield, low energy consumption, long catalyst life, plant reliability, low maintenance cost is really a multi function, with the possibility to reach the best in relation with the particular site conditions and customer's needs.
• High performance Process design – High level of heat recovery coupled with minimisation of hot void volumes and high homogeneity in distribution.
• Mechanical design – High plant reliability comes from plant thermal and mechanical analysis (including FEA) enabling the lowest temperature gradients, and improving stress distribution.
• Hot zone lay out - position of reactors and exchangers are settled in order to minimise residence time at high temperature in interconnecting pipelines, taking care either of pressure drop and piping elasticity.
• Great know-how on testing dehydrogenation catalysts and polymerisation inhibitors/retarders to be used in the EB plant.

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General Purpose PolyStyrene has been producing by the innovative continuous mass process since 70s at the Versalis sites based on a 75 KTA plant unit. During the next decades the GPPS technology has been considerably improved and in 1989 a new GPPS unit based on the updated technology started up the GPPS production with a capacity of 80 KTA.
Further units were licensed first in Hong Kong and then in Brazil, with capacity respectively of 80 and 50 KTA.
Based on such technology Versalis is currently leading the GPPS market, whose requirements in terms of quality and environmental impact have continuously increased in the last decades. Versalis R&D has then continuously updating its technology and product portfolio, by improving the key proprietary equipment and further optimising the process cycle. The EdistirR GPPS class of products is a recognized benchmark within the European market scenario

The key features of Versalis GPPS technology are :
process technology are as follows:

• Special and unique mechanical design of key equipment such as the reactor and devolatilizer;
• Really simple process scheme and easy process control.
• flexible technology allowing tailor-made solutions for specific needs, in terms of plant capacity and products range;
• minimum amounts and number of foreign materials introduced in the process.
  • Very low residual monomer and oligomer content;
• Very low amounts of chemicals consumption for the same property balance;
• fine-tuned macromolecular structure (molecular weights and its distribution).
  • Even the most challenging fields of application like the insulation panels (XPS) and the expanded trays by means of direct gassing are covered by the EdistirR GPPS portfolio

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High Impact PolyStyrene has been producing by the innovative continuous mass process since 70s at the Versalis sites based on a two plants located in Italy and Belgium. During the next decades the HIPS technology has been considerably improved and in 1991/1992 two new units were started up in Italy and Hungary.
Further units were licensed first in Hong Kong and then in Brazil, with capacity respectively of 80 and 70 KTA.

Based on such technology Versalis is currently leading the HIPS market, whose requirements in terms of quality and environmental impact have continuously increased in the last decades. Versalis R&D has then continuously updating its technology and product portfolio, by improving the key proprietary equipment and further optimising the process cycle. The EdistirR HIPS class of products is a recognized benchmark within the European market scenario

The key features of Versalis GPPS technology are :

• Special and unique mechanical design of key equipment such as the reactor and devolatilizer;
• Really simple process scheme and easy process control.
• flexible technology allowing tailor-made solutions for specific needs, in terms of plant capacity and products range;
• minimum amounts and number of foreign materials introduced in the process.
  • Very low residual monomer and oligomer content;
• very high rubber phase efficiency (reduced rubber consumption), minimum rubber cross-linking and
  polymer degradation;
  • The Versalis HIPS technology minimizes the effects of raw materials and chemical impurities on the process and product structural parameters.
• fine-tuned macromolecular structure (molecular weights and its distribution).

Even the most challenging fields of applications like the highly chemical-resistant inner liners for the Refrigeration Industry as well as grades for teletronic industries are covered by the EdistirR HI PS portfolio

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Expandable PolyStyrene has been producing by the innovative continuous mass process since 70s at the Versalis sites based on a 35 KTA plant unit in Italy and a further unit set up in Belgium during 80s with a 35 KTA capacity. During the next decades considerably improvements have been reached such as the introduction of a suspending agent and further EPS unit came on stream in Hungary with a capacity of 40 KTA and a new EPS unit with a 40 KTA capacity has been recently licensed.
Based on such technology Versalis is currently leading the EPS market, whose requirements in terms of quality and environmental impact have continuously increased in the last decades. Versalis R&D has then continuously updating its technology and product portfolio, by improving the key proprietary equipment and further optimising the process cycle. The ExtirR EPS class of products is a recognized benchmark within the European market scenario
The key features of Versalis EPS technology are

• inorganic suspending agent, which brings a unique narrow bead size distribution;
• simple process scheme and easy process control;
• single step technology (the impregnation of the beads with pre-foaming agent is then made during the polymerisation stage);
• very good reactor filling and no need for solvent washing of the reactors;
• easy availability in the world market of the chemicals used in the process;
• flexible and wide product range, developed and fine tuned for any market requirement.

The ExtirR EPS product portfolio is characterized by a very good expandability, by a short cycle times and very good fusion together with a fine-tuned design for specific applications. Within ExtirR product portfolio a customer can find suitable grades for all the current processing technologies such as the moulding, transfer, vacuum or blocks, covering even the most challenging applications such as the fire resistant sheet and blocks for insulation
in the building industry as well as many others;
following main application.

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Acrylonitrile-Butadiene-Styrene plastic has been producing by the traditional emulsion based process since 1963. At the end of the ‘80s, Versalis started the production of ABS based on an innovative continuous mass technology developed meanwhile by its R&D and extensively used in HIPS and GPPS production since the 70's.
In 2005, Versalis decided to concentrate only on the continuous mass technology, stopping any production and sales of emulsion based products.
The main features of Versalis continuous mass ABS process technology are as follows:

• Proprietary, accurate process and mechanical design of key equipment such as reactor and devolatilizer).
• Simple process scheme and easy process control.
• Flexible technology allowing tailor-made solutions for specific needs, in terms of plant capacity and product range.
• Environmentally friend technology compared to emulsion.
• ABS continuous mass product grades show higher thermal stability beside a very low volatiles content..

After a complete switch from emulsion to continuous mass technology, the Versalis SinkralR product portfolio is now a well recognized benchmark within the European scenario

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Versalis has been producing Styrene-Acrylonitrile resin via traditional suspension based process since the ‘60s. In the early ‘90s, Versalis started the production of SAn based on an innovative continuous mass technology developed meanwhile by its R&D and already used in the other styrenic polymers production since the 70's. The development of continuous mass technology for the production of SAn allows Versalis to achieve the following features:

• Proprietary, accurate process and mechanical design of key equipment such as reactor and devolatilizer.
• Simple process scheme and easy process control.
• Flexible technology allowing tailor-made solutions for specific needs, in terms of plant capacity and product range.
• Environmentally friend technology compared to emulsion.
• SAN continuous mass product grades show higher thermal and colour stability beside a very low volatiles content..

Versalis KostilR product portfolio is nowadays a well recognized quality benchmark within the European scenario

Emulsion polymerized styrene-butadiene rubber is one of the most worlwide used polymers, employed in a large variety of applications which significantly contribute to our standards of living as well as in enhancing our quality of life. The wide range of products achievable by the Versalis proprietary technology covers all e-SBR field of application like tires, footwears, light coloured mechanical goods, flooring, adhesives, pharmaceutical and food contact articles, microcellular articles, hoses, conveyor belts, high hardness soles and sheeting, technical goods with high hardness.
High Solids SBR Latices, whose main applications are in moulded foam, gel and non-gel carpet foam and stiffness enhancer Latices, are also leading product based on Versalis proprietary technology.
Main technology highlights are :

• Process design advanced features in polymerization and recovery sections
• Great attention to environmental issues in design of each process stage, according to the
• BAT and to the IISRP suggestions to the E.U. Authorities Wide range of products grades coupled with a real process know-how enables meeting the specific needs of the customer
• High flexibility allowing production, in the same continuous reactors train, of base Latices blendable with batch or semibatch latices to produce a HSR/HSL grades and SBR latices
• Capacity up to 50 kt/y per reaction unit are afforded, based on a single finishing line capacity ranging from 30 to 40 kt/y depending on product mix. Proper arrangement of reaction and finishing lines allows to reach any required plant capacity.

Industrial units based on proprietary technology are on-stream in Italy and UK for about 200 kt/y of global installed capacity

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Solution polymerized styrene-butadiene rubber is the unrivalled raw material for highly specified tyre components used in the fabrication of high performance tyres, where the lowest fuel consumption and the highest durability are required.
The wide product portfolio allowed by the Versalis technology can be then used for fabrication of special tyre threads showing enhanced wet grip performance as well as for fabrication of winter tyres and special mechanical goods.
Depending on desired product and application, batch and continuous Solution technologies are available .
s-SBR proprietary technology has been developed as an alternative to emulsion technology to produce new product grades and also to greatly reduce some environmental impact of the emulsion technology.
First production line was built in Grangemouth (UK) in 1995, based on batch technology with a 30 kt/y capacity,
followed in 1999 by a new reaction section based on continuous technology.
Main technology highlights are .

• Process design advanced features in polymerization and purification sections
• Large production flexibility due to availability of both batch and continuous polymerization technologies, whose selection is driven by the final application of the product
• High and medium vinyl grades as well as Dry and Oil Extended polymers are allowed
• Production of polymers with linear radial or branched different macrostructures
• Capacity up to 60 kt/y per reaction unit are afforded, based on a single finishing line capacity up to 30 kt/y

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SBS copolymers made by styrene and butadiene linked homopolymer blocks belong to the class of thermoplastic elastomers (TPE) whose elastic behaviour – the properties to change and recover the shape when a force is first applied and then removed – and thermoplastic behaviour – the property to become soften, viscous and free-flowing like a liquid when heated and return solid when cooled at room temperature – are joined together in the
same material.
The balance between properties and processability leads SBS based material focusing on unique applications instead of only replacing general-purpose rubber. Uses range from enhancer of bitumen performance in road paving and roofing applications (particularly under extreme weather conditions), through adhesives, sealants, coatings, footwear up to compounds able to enhance grip, feel, and appearance properties in toys, automotive, personal hygiene, and packaging goods market.
Versalis SBS technology is well-known for its high flexibility in tailoring the different product grades required by the SBS market to meet new application requirements. Versalis SBS technology allows then competitive production of the most common SBS grades, as well as of the additional SBS grades for special applications. Main technology highlights are .

• Process design advanced features in polymerization and purification sections
• Cyclopentane, cyclohexane or blend highly compatible with all different polymer compositions, can be used as solvent depending on local climate conditions
• High purity linear and radial triblock polymers, with four arms, are allowed by the proper selection of halosilane structure as coupling agent
• High plant capability as well as easy operability due to both specifically designed feeding system for chemicals and batch automation
• Capacity up to 50 kt/y for single reaction line is afforded by using three batch reactors, with capacity up to 30 kt/y per single finishing line
• Industrial units based on proprietary technology are on-stream in US and in Italy for about 140 kt/y of installed capacity
• Production of Low Cis Butadiene Rubber (LCBR) grades in the same unit

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NBR butadiene-acrylonitrile rubbers are copolymers of butadiene (BD) and acrylonitrile (AN) produced by means of an emulsion polymerisation reaction initiated by redox catalyst systems.
The high resistance to oils over a wide temperature range is certainly one of most important feature of Nitrile Rubber. Furthermore, goods NBR-based are well addressed for their high strength and resistance to abrasion properties. Examples of NBR goods are Hose, Belting and Cable, Gasket, Seals and O-rings, Molded and Extruded Products, Latex applications, Adhesives and sealants
Versalis owns NBR production facilities in its production site in Porto Torres (IT). The plant started first production of NBR polymers in 1973 based on cold radicalic polymerization technology and was then continuously modified and improved based on market requests and feedbacks as well as on increasing safety regulations requirements. Main technology highlights are .

• Polymerization section:
  • High reacting volume per reactor, thus allowing higher plant capacity with same number of reactors;
  • monomers and modifier's ratio and feeding are individually defined per each grade and each rate, increasing the flexibility of the process and the comonomers' distribution in the macromoleculas;
  • NBR technology accepts a wide range of monomer purity.

• Monomers Recovery section:
  • Great reduction of pollutants into the the water drains sent to Waste Water Treatment;
  • Very low quantity of reject material sent to incineration

• Finishing section :
  • Good quality of the residual VOC content (no thermal oxidation is required);
  • Great reduction of COD and Suspended Solid in the waste water stream sent to Waste water treatment
    

High Cis Polibutabiene rubber technology was first developed in the 80s, with the aim to produce rubber grades with specific properties in tyre sector as well as in other industrial applications. Typical High Cis Polibutabiene rubber plant consists of one reaction section, one finishing line and one packaging line.

Main technology features are :

• Polymerization section:
  • The solvent is hexane, in comparison with the conventional processes where aromatic solvent are used. Non aromatic solvent brings several advantages in terms both of economics (steam consumption in the stripping operation is lower due to the lower boiling point of hexane) and of environmental health (the toxicity of hexane is lower than that of aromatics).
  • The polymerization reaction is carried out adiabatically bringing many advantages concerning energy consumption, investment cost and easier operations, . Furthermore the problems of products quality that would arise in case of troubles in removing the polymerization heat are then avoided.
  • Neodymium is not an oxidation catalyst. Then normal antioxidants easily protect HCBR from oxidation during processing and storage because Nd does not catalyze the action of oxygen on HCBR, while some troubles may occur in conventional processes where Cobalt and Nichel are normally used.
  • No purification operations are necessary on the cement to remove catalyst residuals.

• Stripping section
  • Configuration of the stripping section: three stages arrangement optimized in such a way to minimize steam consumption without penalizing emissions of hydrocarbons from finishing line to the atmosphere.
• Finishing
  • Technology allows to collect the most concentrated streams and to feed them to a thermal oxidizer, in order to reduce emissions in the finishing stacks.

PBE-1 catalyst is a high-performance composite material specifically designed for industrial cumene and ethylbenzene synthesis in fixed bed reactors. It is the result of long-term research within Eni associated with direct Versalis (former EniChem) experience in both cumene and ethylbenzene industrial production. PBE-1 is a beta zeolite based catalyst displaying unusual and unrivalled performances in industrial cumene and ethylbenzene synthesis thanks to its unique combination of extrazeolite and zeolite properties.
Main distinguishing marks of PBE-1 catalyst are :

• Zeolite morphology
• Zeolite acid site distribution
• Extrazeolite porosity and binder
• Mechanical strength
• Poisons tolerance

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PBE-2 catalyst is a high-performance composite material specifically designed for transalkylation stage of industrial ethylbenzene synthesis in fixed bed reactors. It is the result of long-term research within Eni associated with direct Versalis (former EniChem) experience in ethylbenzene industrial production. PBE-2 is a Y zeolite based catalyst displaying unusual and unrivalled performances in transalkylation reaction of polyethylbenzenes and benzene thanks to its unique combination of extrazeolite and zeolite properties.
Main distinguishing marks of PBE-1 catalyst are :

• Zeolite morphology
• Zeolite acid site distribution
• Extrazeolite porosity and binder
• Mechanical strength
• Poisons tolerance