RANEY Catalysts - Grace

1 RANEY Catalysts The Standard of Excellence in | 1 RANEY CatalystLeader in HydrogenationRANEY Catalysts from Grace are integral in the processing of petroleum and food products and the production of an extensive array of pharmaceuticals, fibers, fragrances, and personal care. In these fast-paced industries, you need efficiency and speed to adapt to the demands of the ever-changing consumer demands and regulatory standards. Grace is a global Catalysts leader and a major supplier of RANEY hydrogenation and dehydrogenation Catalysts . Our base metal RANEY products provide unmatched performance in the synthesis of organic compounds. When you partner with Grace , you get longer lasting, more efficient, and more reliable RANEY Catalysts are the most efficient class of Catalysts available for many hydrogenation processes.

2 With distinctively high activity, selectivity, and handling characteristics, RANEY Catalysts significantly increase throughput while decreasing the formation of undesirable by-products. Through advances in surface chemistry and by specifically tailoring Catalysts to meet a demanding and unique range of industrial requirements, Grace consistently provides solutions that are both flexible and lasting. Adding promoters can modify the surface characteristics of RANEY catalyst for a variety of applications. Grace has over 60 years of experience innovating with superior RANEY Catalysts . In 1963, Grace acquired the manufacturing site, technology, and registered trademark of RANEY Catalysts from the original inventor. In 1926, Murray RANEY developed RANEY Catalysts for the hydrogenation of vegetable oils.

3 They were found to be 5x more active than the best Catalysts used in the hydrogenation of cottonseed of Partnering with Grace Pioneer of RANEY Catalysts with over 60 years of experienceR&D / technical service to continually improve performanceFlexible assets for scale-up and commercial productionRange of analytical tools for product and process improvement Consistency of quality Global footprint to support local demands Customized Catalysts to meet specific customer requirementsAdvantages of RANEY Catalysts Highly active (high metal surface area) and ready-to-useVersatile for various hydrogenations and dehydrogenationsLow cost compared to precious metal catalystsEase of separation from product (high density and magnetic separation)Efficiency; longer catalyst lifeDurability in wide range of environmentsCustomizable and offers the ability to add promotersFlexibility to customize particle size rangesWith distinctively high activity, selectivity, and handling characteristics, RANEY Catalysts significantly increase throughput while decreasing the formation of undesirable by-products.

4 | 2 RANEY CatalystGrace Catalysts Portfolio Grace Catalysts are used in a wide range of hydrogenation and dehydrogenation applications. HydrogenationFunctional GroupProduct TypeProduct ExampleGrace CatalystBenefitsAromatic NitroAr-NO2 Aromatic AmineAr-NH2 TDA Aniline6800 (Ni)2400 (promoted Ni)4200 (promoted Ni) Higher productivity Good settling properties Less extensive cleanups Less down timeAliphatic NitroR-NO2 Aliphatic AmineR-NH2 Alkylamines Amino alcohols4200 (Ni)2800 (Ni)3201, 3111 (promoted Ni) Long lifetime High activityCarbonyl: Aldehyde RCHOP rimary AlcoholRCH2 OHSorbitolButanolButanediol3111/3110 (promoted Ni)5831 (fixed-bed Mo/Ni) Lower overall cost Better settling times Lower losses Consistent performance superior for different grades of dextroseCarbonyl.

5 Ketone RR C=OSecondary AlcoholRR CH2 OHIsopropanol3111/3110 (promoted Ni) Better settling times Better filterability Resistance of poisonsNitrileRCNA mineRCH2NH2 HMDA and isomersFatty Amines( C4-C6 diamines)2400 (Ni)2724 (promoted /Co)2786 (fixed-bed promoted /Co)2400 (promoted/Ni)2800 (Ni) Improved selectivity Consistent performance Improved settling times Less use of NH3 (2724) Longer life for Co catalystAlkene (Olefin)RCH=CHR (Saturated derivative)SulfolaneRosin-esters5601 (Ni)4200 (Ni) 2400 (promoted Ni)2800 (Ni) Higher performance Consistency Better usage of catalystsAlkyne (Acetylene)RC CR (Saturated derivative)Butanediol4200 (Ni)2800 (Ni)5886 (Ni) Unique fixed-bed catalyst Next generation activated catalyst Catalyst shelf stableReductive AlkylationFunctional GroupProduct TypeProduct ExampleGrace CatalystBenefitsCarbonyl + amine2 , 3 AminesMethyl Propylamine2800 (Ni)4200 (Ni)2724 (Co) Higher selectivity Longer lifeDehydrogenation/OxidationFunctional GroupProduct TypeProduct ExampleGrace CatalystBenefitsAlcohol (1 or 2 )RCH2OH orRR CH2 OHAcid, aldehyde, ketoneRCOOH, RCHO, or RR C=OGlycine Cyclohexanone2800 (Ni)4200 (Ni)2900 (Cu) Higher selectivity Longer lifeAmino AlcoholH2 NRCH2 OHAMINO ACIDH2N-RCOOHG lycine2900 (Cu)

6 Higher selectivity Longer lifeReductive AminationFunctional GroupProduct TypeProduct ExampleGrace CatalystBenefitsCarbonyl + ammoniaRCHO+NH3 Primary AminePropylamine2800 (Ni)4200 (Ni)2724 (Co) Higher selectivityAlcohol + ammoniaRCH2OH+NH3 Primary | 3 RANEY Catalyst RANEY Catalysts Add ValueRANEY superior metal Catalysts offer extremely high activity, excellent selectivity, a high degree of versatility , ease of filtration, and excellent settling characteristics. More importantly, RANEY Catalysts offer genuine savings in both low initial cost and low ultimate cost per pound of end Selectivity Reduces By-Product RANEY catalyst formulations can be fine-tuned to meet the performance requirements of specific applications.

7 RANEY Catalysts provide consistent and reliable performance. They selectively hydrogenate a wide variety of functional organic compounds under mild to severe reaction conditions. The low by-product formation substantially reduces environmental waste disposal costs and increases the effective usage of raw materials providing significant value to the process. High Activity Increases Production RatesGrace works closely with customers to optimize the performance of RANEY Catalysts helping increase throughput in large-scale hydrogenation processes. The RANEY Catalysts have higher activity due to higher active site density as compared to supported base metal Catalysts and, in some cases, supported precious metal Catalysts . In an aromatic nitrile-to-amine application, for example: Yield improved from to , saving the customer over $ million in raw materials.

8 The improved yield also reduced high boilers which reduced waste disposal Life Improves Economics Extremely efficient, RANEY Catalysts last longer in reaction mixtures and thus contribute to reduced net costs. RANEY Catalysts are useful in systems containing many aqueous solutions, especially bases, where other Catalysts are to Poisons Provides Greater Flexibility The high metal content in RANEY Catalysts provides protection against severe catalyst poisoning. This high resistance to catalytic poisons allows for greater flexibility in the selection of raw material. Grace switched a customer from a supported nickel fixed-bed catalyst to a RANEY fixed-bed cobalt catalyst and doubled the lifetime from six months on-stream to over 12 months on-stream.

9 Not only did the customer cut their catalyst consumption in half; they eliminated a second shut-down, saving hundreds of thousands of dollars per Overall Economy Increases Profits RANEY Catalysts offer the lowest initial cost per pound of catalytic metal particularly when compared to precious metal Catalysts . RANEY Catalysts also offer manufacturing flexibility to use many metals, providing overall economics to the Lowers Cost Spent catalyst can be recycled to recover some of the initial metal investment. Metal recycling is a well-established process and there many global companies who have expertise in this segment. Grace can provide regional contacts to help you recycle spent RANEY Nickel Catalyst 5% Platinum on Carbon Catalyst Sticker Price $30/kg$1,600/kgRecovery Value($5/kg)($1,425/kg)Net Cost$25/kg$175/kgAdditional savings are possible in amount of working capital Convenience The active RANEY Catalysts are supplied ready-to-use under water and do not require preactivation.

10 This will reduce batch startup times and labor, facilitating improved of Settling Increases Plant CapacitySettling rates of RANEY Catalysts in slurry form are superior to those of finely divided supported Catalysts . High density RANEY Catalysts helps separate the catalyst quickly from the reaction medium. Shorter processing times result in increased plant capacity and economics. The shorter contact times after the reaction would potentially minimize the side reactions providing enhanced selectivity for desired Added with Grace Catalysts $ $ $ SETTLING LEADS TO GREATER THROUGHPUT$ , $M 12,000 MT/YR Sorbitol Plant RANEY cut total cycle time and increased batches per day from to Plant gained additional 1,000 MT/YR of capacity Added $1M in additional | 4 RANEY CatalystThe RANEY DifferenceRANEY Catalysts start as alloys and maintain their metallic properties through the life cycle of the Catalysts .