Source: HANDBOOK OF PETROLEUM REFINING PROCESSES

CHAPTER 9.4

UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES

Nelson A. Cusher
UOP LLC Des Plaines, Illinois

INTRODUCTION
Light straight-run (LSR) naphtha fractions made in the refinery are predominantly C5s and C6s. Some C7s are also present. They are highly paraffinic and have clear research octane numbers (RONC) usually in the 60s. The nonnormal components have higher octanes than normal paraffins (Table 9.4.1) and are excellent gasoline-blending feedstocks. For the refiner who wants to upgrade the octane of a gasoline pool and has use for a highpurity normal paraffin product, UOP*s IsoSiv* separation technology is a good fit. However, if octane improvement is of primary importance, isomerization technology is the best choice. Paraffin isomerization to upgrade the octane of light-naphtha streams has been known to the refining industry for many years and has gained importance since the onset of the worldwide reduction in the use of lead antiknock compounds. This technology continues to be important in view of current U.S. legislation on reformulated gasoline. The most cost-effective means to upgrade an LSR feedstock in a grassroots situation is UOPs Penex* process, which is discussed further in Chap. 9.3. However, refiners with idle hydroprocessing equipment, such as old catalytic reformers or hydrodesulfurization units, can consider converting this equipment to a UOP Once-Through (O-T) Zeolitic Isomerization process (formerly known as the Shell Hysomer process). The process scheme is similar to that of a simple hydrotreater, as shown in Fig. 9.4.1, and conversions can be accomplished quickly and at low cost. With O-T Zeolitic Isomerization, a 10 to 12 octane-number increase for the C571C (160F) light naphtha can be achieved. For those refiners who need more octane than can be achieved from the once-through operation, an additional 8 to 10 RONC can be gained by adding molecular sieve adsorption to the O-T Zeolitic Isomerization process. Molecular sieve adsorption is used to extract the unreacted normal paraffins so they can be recycled to extinction. This approach
*Trademark and/or service mark of UOP. Trademark and/or service work of Shell Oil.

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES 9.30 TABLE 9.4.1
ISOMERIZATION

Properties of Common Gasoline Components Molecular weight Boiling point,* F 10.9 31.1 49.0 82.2 96.9 120.7 121.5 136.4 140.5 145.9 155.7 161.3 174.6 176.2 176.9 177.3 177.6 186.9 193.6 194.1 197.5 231.1 277.1 306.3 329.2 345.2 Density, * lb/gal 4.69 4.86 4.97 5.20 5.25 6.25 5.54 5.54 5.57 5.44 5.48 6.28 5.64 7.36 5.64 6.53 5.78 5.81 5.83 5.68 5.76 7.26 7.26 7.21 7.35 6.11 RONC 100+ 93.6 116 92.3 61.7 100 91.8 101.7 73.4 74.5 94.8 91.3 92.8 100+ 83.1 83 112 98 88.5 55 65 100+ 100+ 100+ 100+ 53

Isobutane n-butane Neopentane Isopentane n-pentane Cyclopentane 2,2-dimethylbutane 2,3-dimethylbutane 2-methylpentane 3-methylpentane n-hexane Methylcyclopentane 2,2-dimethylpentane Benzene 2,4-dimethylpentane Cyclohexane 2,2,3-trimethylbutane 3,3-dimethylpentane 2,3-dimethylpentane 2,4-dimethylpentane 3-methylhexane Toluene Ethylbenzene Cumene 1-methyl-2-ethylbenzene n-decane

58.1 58.1 72.1 72.1 72.1 70.0 86.2 86.2 86.2 86.2 86.2 84.2 100.2 78.1 100.2 84.2 100.2 100.2 100.2 100.2 100.2 92.1 106.2 120.2 120.2 142.3

*The values for C and kg/m3 can be found in Table 10.5.1.

FIGURE 9.4.1

UOP Once-Through Zeolitic Isomerization process.

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES

UOP TIP AND O-T ZEOLITIC ISOMERIZATION PROCESSES

9.31

of complete isomerization is referred to as UOPs TIP* process. Because O-T Zeolitic Isomerization is an integral part of the TIP process, the ensuing discussion begins with the once-through operation and concludes with a discussion of TIP.

O-T ZEOLITIC ISOMERIZATION PROCESS

Process Chemistry Thermodynamically, low temperatures are preferred for obtaining maximum amounts of branched paraffins in the reaction product. Operation below 150C (302F) for maximum activity requires a catalyst that uses a halide activator. For these catalysts, feed drying is required to eliminate any corrosion or catalyst stability concerns. The catalyst used in the O-T Zeolitic Isomerization process, however, is based on a strongly acidic zeolite with a recoverable noble-metal component. No external acid activators are used and the catalyst does not produce a corrosive environment. Therefore, feed drying is not necessary. The catalyst base behaves as an acid of the Brnsted type because it has a high activity for normal-pentane isomerization in the absence of a metal component. At a relatively low hydrogen partial pressure, the carbonium ion concentration generated by the activated low-sodium zeolite is apparently higher than it would have been if the paraffin-olefin equilibrium had been established. This excessive carbonium ion concentration leads to not only high initial conversion but also unstable operation and low selectivity under preferred operating conditions (Fig. 9.4.2). This figure also shows that incorporation of the metal function stabilizes the conversion and lowers the initial activity. These results are to be ascribed to the lower olefin and carbonium ion concentration in the presence of the dualfunction catalyst as a result of the paraffin-olefin equilibrium. The reaction mechanism on the new catalyst is shown in Fig. 9.4.3. Carbonium ions and isoparaffins are generated from normal paraffins by a combination of hydride-ion abstraction and hydride-ion transfer reactions. In the adsorbed state, skeletal rearrangement reactions occur. This reaction is the horizontal path shown in Fig. 9.4.3. Alternatively, while the normal pentane is in the carbonium ion state (nP+ or iP+), it may surrender a proton to form an olefin, which in turn is hydrogenated to form a paraffin (these two paths are vertical). Even a minute amount of the noble metal stabilizes the conversion to isopentane, provided that the noble metal is well dispersed and distributed throughout the zeolite (Table 9.4.2). However, in commercial applications, more than the minimum amount of noble metal is required. Normally the catalyst contains a few tenths of a percent of precious metal. Proper catalyst preparation methods and start-up procedures are essential for optimal results.

Process Description The O-T Zeolitic Isomerization process is a fixed-bed, vapor-phase process for the catalytic isomerization of low-octane normal pentane or normal hexane or both to high-octane isoparaffins. The isomerization reaction is carried out at 245 to 270C (470 to 520F) and 21 to 35 kg/cm2 (300 to 500 lb/in2 gage) in the presence of hydrogen. Equipment requirements are a reactor vessel, heater, recycle hydrogen compressor, feed-product heat exchanger, product cooler, phase separator drum, and product stabilizer section.
*Trademark and/or service mark of UOP.

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES 9.32

ISOMERIZATION

FIGURE 9.4.2 Effect of noble-metal addition on n-pentane isomerization. (Selectivity for isopentane overcracking is indicated in parentheses.)

FIGURE 9.4.3

Isomerization reaction path.

A comparison of catalytic reforming and O-T Zeolitic Isomerization appears in Table 9.4.3. A brief discussion about the required equipment from the perspective of converting an existing hydrotreater follows. Reactors. With catalytic reformers that were originally designed for a weight hourly space velocity (WHSV) comparable to that of the O-T Zeolitic Isomerization process, no major modifications to the reactors are required except to eliminate interstage

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES

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TABLE 9.4.2 Influence of Metal Load on Zeolite on Hydroisomerization of n-Pentane. mol metal/100 g zeolite 0.000 0.025 0.25 2.00 5.4 First-order rate constant 0.12 1.5 1.6 2.0 2.3

TABLE 9.4.3

Comparison of Catalytic Reforming and O-T Zeolitic Isomerization Catalytic reforming O-T Zeolitic Isomerization C5-C6 8890 2135 (300500) About 260 (500) 13 14 About 70 required Nearly isothermal 0.81.0 (1214) 0.91.1 (1316) Every 2 to 3 years
standard cubic feet per barrel.

Feed composition Feed gravity, API Operating pressure, kg/cm2 (lb/in2 gage) Operating temperature, C (F) Feed, WHSV H2/HC ratio, mol/mol H2, SCFB Heat of reaction Reid vapor pressure, kg/cm2 (lb/in2 gage) Feed Product Catalyst regeneration
Note: WHSV weight hourly space velocity; HC

C7+ 5262 1435 (200500) About 510 (950) 15 510 5001700 produced Highly endothermic 0.050.07 (0.71.0) 0.20.4 (36) Continuous to about 1 year periodic
hydrocarbon; SCFB

heating. Because of the difference in feed densities, the O-T Zeolitic Isomerization catalyst requirement is typically about 20 percent less than the reformer catalyst requirement. If the O-T Zeolitic Isomerization unit is to be designed for a lower WHSV or if recycle of normal paraffins to obtain the maximum octane increase is desired, converting from internal to external insulation can achieve about a 25 to 30 percent increase in reactor volume. This increase is possible because of the relatively low operating temperature for the O-T Zeolitic Isomerization process; however, the material used to construct the reactor shell should be checked for pressure or temperature limitations. Compressors. The recycle-compressor capacity for a reformer is usually more than adequate for the O-T Zeolitic Isomerization process. A 25 kg/cm2 (350 lb/in2 gage) reformer will have about twice the capacity required for the O-T Zeolitic Isomerization process. In plants containing two compressors, each with a 50 percent capacity, one compressor can be shut down. Makeup hydrogen for the O-T Zeolitic Isomerization process can be reformer net gas. If the reformer supplying the hydrogen is a low-pressure unit, a small makeup compressor is required. For a O-T Zeolitic Isomerization unit processing 5000 barrels per day (BPD) of feed, hydrogen makeup is typically about 500,000 standard cubic feet per day (SCF/day).

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES 9.34

ISOMERIZATION

Heaters and Heat Exchangers. Heat exchange equipment and heaters are usually more than adequate. Interstage reheaters between reactors are not required because the isomerization reaction is mildly exothermic. Feed Pump. Because of differences in feed gravity, feed rate, vapor pressure, and possible net positive suction head (NPSH), a new feed pump may be required. Stabilizer System. In the O-T Zeolitic Isomerization process, the amount of light ends produced is substantially less than in the reforming process. In any case, where a reformer has been converted to an O-T Zeolitic Isomerization unit, the stabilizer feed rate is higher even though the stabilizer overhead product is lower than in the reforming operation. The small amount of light ends plus a bottoms product with a higher vapor pressure may dictate an increased reflux rate or a column retray or both.

Commercial Information The need for a high-octane product to replace the octane lost with lead phaseout and benzene reduction in the gasoline pool has placed more emphasis on isomerization. As previously noted, the attractiveness of the O-T Zeolitic Isomerization process is that it can be adapted to an existing idle hydrotreater, catalytic reformer, or other hydroprocessing unit with minimal investment. The actual time to modify a unit ranges from a few days to a few weeks. Commercial Installations. As of early 2002, more than 30 O-T Zeolitic Isomerization units have been commissioned to process 1000 to 13,500 BPD of feed. About half of these are catalytic-reformer or hydrotreater conversions. One unit was assembled from assorted surplus refinery equipment. Of the conversions, one unit is arranged so that it can be operated as either a reformer or a O-T Zeolitic Isomerization unit by switching a few spool pieces. The oldest of the converted units started up in 1970 in La Spezia, Italy. This unit was integrated with a catalytic reformer so that both units have a common recycle-gas compressor system, product-cooling train, and stabilizer section. Combinations of this sort often result in capital savings of 20 to 40 percent compared to stand-alone isomerization and reforming units. In 10 years of operation, the catalyst in the La Spezia unit was regenerated in situ four times. Typical cycle lengths for O-T Zeolitic Isomerization units are 3 to 4 years. Typical Performance. Paraffin isomerization is limited by thermodynamic equilibrium so that a once-through, or single-pass, isomerization reactor provides only partial conversion of the normal paraffins. In the reactor, C 5 -C 6 paraffins are isomerized to a near-equilibrium mixture, and aromatics become saturated to naphthenes, which, in turn, are partially converted into paraffins. Olefins in the feed are saturated, and C7+ paraffins are mostly hydrocracked to C3 to C6 paraffins. Tables 9.4.4 and 9.4.5 provide a summary of typical O-T Zeolitic Isomerization yields, product properties, conversion costs, utility requirements, and overall operating costs. Typical C5+ isomerate yield is 97 to 98 liquid volume percent (LV %) on feed and the octane number is increased by about 10 to 12, resulting in an isomerate quality of 77 to 80 RONC. Usually no new major equipment is required when a reformer is converted to an O-T Zeolitic Isomerization unit of the same feed capacity. Thus, the only costs are for new piping and instrumentation, engineering, and a charge of O-T Zeolitic Isomerization catalyst. For a unit with a feed rate of 5000 BPD, capital costs will total $3.0 to $4.5 million. This

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES

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TABLE 9.4.4 BPD

Typical Estimated Performance, O-T Zeolitic Isomerization Unit, 10,000 Component Fresh feed to reactor 2018 (1710) 0.10 0.58 16.84 29.07 1.69 0.51 1.93 12.08 8.80 19.35 1.95 3.41 1.75 1.94 100.00 0.659 0.8 (10.8) 68.1 88.4 66.4 87.3 Product 333 (283) 180 (152) 292 (248) 2.50 1.41 30.39 16.17 1.24 8.26 3.74 14.43 9.21 8.24 3.35 0.96 0.0 0.97 100.87 0.648 1.0 (14.2) 79.5 95.5 77.6 96.3

Hydrogen consumption, m /h (1000 SCF/day) Light gas yield, m3/h (1000 SCF/day): C1 C2 C3 C4 + streams, LV % on feed: iC4 nC4 iC5 nC5 Cyclo-C5 2,2-dimethylbutane 2,3-dimethylbutane 2-methylpentane 3-methylpentane nC6 Methylcyclopentane Cyclo-C6 Benzene C7 Total C4+ properties: Specific gravity Reid vapor pressure, kg/cm3 (lb/in2) Octane number: RON, clear RON + 3 cm3 TEL/U.S. gal MON, clear MON + 3 cm3 TEL/U.S. gal

Note: BPD barrels per day; SCF standard cubic feet; RON motor octane number; TEL tetraethyl lead; i iso; n normal.

research octane number; MON

amount is only about half of the cost of a grassroots installation. Expected catalyst life is 10 to 15 years.

TIP PROCESS
General Description Some refiners need more octane from the LSR naphtha fraction than is possible from the O-T Zeolitic Isomerization process. As previously noted, the TIP process combines the O-T Zeolitic Isomerization process with UOPs naphtha IsoSiv process to yield an 87 to 90 RONC product, an improvement of approximately 20 numbers. The TIP unit can be built grassroots, or a UOP IsoSiv unit can be added to an existing O-T Zeolitic Isomerization unit to convert it to a TIP unit. In this type of revamp, generally all existing equipment can be used.

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES 9.36 TABLE 9.4.5
ISOMERIZATION

O-T Zeolitic Isomerization Conversion Economics and Performance* 750 0.0006 (0.0025) 0.33 (0.06) 0.05 0.5 (1.1) 2.76.1 (49) 7780 9798 1015

Total capital required, $/BPSD Utilities, per BPSD feed: Fuel consumed (90% efficiency), million kcal/h (million Btu/h) Water at 17C rise, m3/day (gal/min) Power, kWh Steam at 10.5 kg/cm2 (150 lb/in2 gage), saturated, kg/h (lb/h) Hydrogen consumption, m3/day (SCF/h) Typical performance: Isomerate, RONC C5+ isomerate yield, LV % Catalyst expected life, years

*Basis: Battery limits; U.S. Gulf Coast, 2001, 40006000 BPSD, including new stabilizer, new piping and instrumentation, engineering, and catalyst.

The TIP process uses adsorption technology to remove and recycle the unconverted normal paraffins. During the adsorption step, a shape-selective molecular sieve removes all the unconverted normal paraffins from the isomerate to allow the branched-chain isomers to pass through. These adsorbed normals are then desorbed by stripping with recycle hydrogen and passed directly into the isomerization reactor. Because the entire process is carried out in the vapor phase, utility requirements are low. The entire process operates at a constant low pressure. The presence of hydrogen during the desorption step prevents the buildup of coke on the adsorbent. Like the catalyst, the adsorbent can be regenerated in situ if an upset condition causes coking.

Process Description of TIP The TIP process is a constant-pressure vapor-phase process operating at a moderate pressure, 14 to 35 kg/cm2 (200 to 500 lb/in2 gage) range, and moderate temperatures, 245 to 370C (475 to 700F). Hydrogen at a sufficient partial pressure must be present during isomerization to prevent coking and deactivation of the catalyst. A simplified schematic flow sheet is shown in Fig. 9.4.4. Hydrotreated fresh feed is mixed with the hot recycle stream of hydrogen and C5-C6 normal paraffins prior to entering the isomerization reactor. A small stream of makeup hydrogen is also added to the feed of the reactor. The reactor effluent, at near-equilibrium isomerization composition, is cooled and flashed in a separator drum. The liquid product, which contains some unconverted low-octane normal paraffins, is vaporized and passed into a bed of molecular-sieve adsorbent, where the straight-chain normals are adsorbed for recycle back to the isomerization reactor. The branched-chain isomers and cyclic hydrocarbons, which have molecular diameters greater than the diameter of pores in the molecular-sieve adsorbent, cannot be adsorbed and exit from the absorbent bed essentially free of normal paraffins. This isomerate product is stabilized as required to remove any excess hydrogen, 1 to 2 percent cracked products, and any propane or butane introduced with the makeup hydrogen. The hydrogen purge gas from the separator is circulated by means of a recycle compressor through a heater and is then used as a purge gas to strip the normal paraffins previously adsorbed on the molecular-sieve adsorbent bed. The hydrogen plus desorbed normals is then mixed with the fresh feed upstream of the isomerization reactor. The isomerization section and the adsorption section of a TIP unit share a common recycle hydrogen loop. Feedstocks that contain an appreciable amount of heptanes or nonnormal components use an alternative feed point (Fig. 9.4.4). The fresh feed enters the system just upstream of
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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES

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FIGURE 9.4.4

TIP flow scheme.

the adsorbers rather than at the isomerization reactor. This feed-entry point allows the nonnormal components and isoheptanes to pass into the final isomerate product without first passing through the isomerization reactor, where some of the heptanes are hydrocracked to liquefied petroleum gas (LPG). With feedstocks having a low normal-paraffin content, it is also more efficient to have the fresh feed enter the system just upstream of the adsorbers to recover the nonnormal components. Only the adsorbed normal paraffins are then sent to the resulting smaller isomerization reactor. Feeds with high levels of benzene can be processed initially in either the reactor section or the adsorption section. Benzene is saturated completely to cyclohexane in the reactor section, thereby producing a benzene-free isomerate product. For feeds with high levels of benzene, presaturation in a separate reactor at a high space velocity is used to remove the heat of saturation from the TIP reactor. This technology is known as TIPPlus.* Sending the feed to the adsorption section allows the high-octane benzene to pass into the isomerate product. For feeds that are best processed in the adsorber section first but need to minimize benzene in the product, the saturation-section effluent can be sent to the adsorption section of the TIP-Plus process. The refiner needs to evaluate both octane and benzene target levels to determine the proper feed point. The TIP unit is normally designed with the capability for an in situ oxidative regeneration of the catalyst and the adsorbent to minimize downtime in the event of an unexpected upset that might coke the catalyst or the adsorbent. Commercial Information As of early 2002, more than 30 TIP units were in operation worldwide. Tables 9.4.6 and 9.4.7 provide a summary of typical TIP process yields, product properties, capital costs, utility requirements, and overall operating costs. A 0.6 power factor applied to the ratio of fresh-feed rates can be used with the cost given in Table 9.4.7 for a quick estimate of the

*Trademark and/or service mark of UOP.

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES 9.38 TABLE 9.4.6
ISOMERIZATION

Typical Estimated Yields for the TIP Process, 10,000 BPD Fresh feed to reactor 2175 (1844) 10 58 1,684 2,907 169 51 193 1,208 880 1,935 195 341 175 194 10,000 0.659 0.8 (10.8) 68.1 88.4 66.4 87.3 Adsorber feed 190 (161) 81 (69) 311 (264) 337 1,035 5,254 3,188 153 1,052 528 2,042 1,307 1,272 397 113 0 103 16,781 0.642 1.2 (16.7) 79.7 95.6 77.7 96.4 Recycle paraffins 194 1,247 1,446 3,411 33 215 98 368 230 1,301 68 19 0 15 8,645 0.632 1.4 (20.6) 70.7 90.1 69.4 90.4 Isomerate product 288 136 4,523 142 132 910 458 1,771 1,134 22 344 98 0 89 10,047 0.640 1.3 (19.2) 88.3 100.9 85.8 102.5

Component H2 consumption, m3/h (1000 SCF/day) Light gas yield, m3/h (1000 SCF/day): C1 C2 C3 C4+ streams, BPSD: iC4 nC4 iC5 nC5 Cyclo-C5 2,2-dimethylbutane 2,3-dimethylbutane 2-methylpentane 3-methylpentane nC6 Methylcyclopentane Cyclo-C6 Benzene C7 Total C4+ properties: Specific gravity Reid vapor pressure, kg/cm2 (lb/in2) Octane number: RON, clear RON+3 cm3 TEL/U.S. gal MON, clear MON+3 cm3 TEL/U.S. gal

investment costs for different-size TIP units. Utilities and catalyst-adsorbent requirements tend to increase in direct proportion to an increase in fresh feed rate.

Wastes and Emissions No wastes or emissions are created by the O-T Zeolitic Isomerization or TIP processes. Product stabilization, however, does result in small amounts of LPG (C3 + C4, rich in iC4) and in stabilizer vent (H2 + C1 + C2) products. The stabilizer vent products are usually used as fuel. The LPG is a valuable by-product that is blended elsewhere in the refinery.

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UOP TIP AND ONCE-THROUGH ZEOLITIC ISOMERIZATION PROCESSES

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TABLE 9.4.7

TIP Process: Economics and Performance 32004000 240 7.8 (31) 2159 (396) 1455 2.8 (6.2) 17.7 (26)

Economics: Investment,* $/BPSD Catalyst and adsorbent inventory, $/BPSD Utilities: Fuel consumed (90% furnace efficiency), million kcal/h (million Btu/h) Water at 17C rise (31F), m3/day (gal/min) Power, kWh Steam at 10.5 kg/cm2 (150 lb/in2 gage) kg/h (lb/h) Hydrogen consumption (70% hydrogen purity), 1000 m3/day (1000 SCF/h)
*Battery limits, U.S. Gulf Coast, 2001, feed rate 40006000 BPSD.

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