Source: HANDBOOK OF PETROLEUM REFINING PROCESSES

CHAPTER 9.3

UOP PENEX PROCESS

Nelson A. Cusher
UOP LLC Des Plaines, Illinois

INTRODUCTION
A component of refinery gasoline pools that frequently offers the best opportunity for quality improvement is the pentane-hexane fraction, or light straight-run (LSR) naphtha. The LSR is characterized by a low octane number, ordinarily 60 to 70 research octane number (RON), clear. Historically, this fraction, which constitutes approximately 10 percent of a typical gasoline pool in the United States and often a higher percentage in Europe, has been blended directly into gasoline without additional processing except perhaps treating for mercaptan removal. The low octane rating could be increased by approximately 16 to 18 numbers because of its excellent lead susceptibility. The low octane placed the C5-C6 straight run in the position of being that segment of the gasoline pool helped most by the addition of lead and least in need of upgrading by processing. As the petroleum industry moved toward the marketing of motor fuels with reduced or zero lead levels, accommodating the LSR in the gasoline pool became increasingly difficult. The conversion of these C5 and C6 paraffins to the corresponding branched isomers to increase their RON, clear, octane number was recognized as a logical and necessary step. One option that UOP* offers to accomplish this upgrading is the Penex* process, which uses a highly active, low-temperature hydroisomerization catalyst. The reliability of this catalyst has been commercially demonstrated since 1959 in butane isomerization (UOPs Butamer* process) and since 1969 in C5-C6 isomerization. As a result of U.S. reformulated gasoline legislation for benzene reduction during the 1990s, a variation of UOPs Penex process is being used to saturate all the benzene in the LSR cut and boost the octane of this gasoline fraction.

PROCESS DISCUSSION
The UOPs Penex process is specifically designed for the catalytic isomerization of pentane, hexanes, and mixtures thereof. The reactions take place in the presence of hydrogen, over a fixed bed of catalyst, and at operating conditions that promote isomerization and
*Trademark and/or service mark of UOP.

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UOP PENEX PROCESS 9.16

ISOMERIZATION

minimize hydrocracking. Operating conditions are not severe, as reflected by moderate operating pressure, low temperature, and low hydrogen partial pressure requirements. Ideally, this isomerization catalyst would convert all the feed paraffins to the highoctane-number branched structures: normal pentane (nC5) to isopentane (iC5) and normal hexane (nC6) to 2,2- and 2,3-dimethylbutane. The reaction is controlled by a thermodynamic equilibrium that is more favorable at low temperature. Table 9.3.1 shows typical charge and product compositions for a C5-C6 Penex unit. The compositions of both the C5 and C6 fractions correspond to a close approach to equilibrium at the operating temperature. With C5 paraffins, interconversion of normal pentane and isopentane occurs. The C6-paraffin isomerization is somewhat more complex. Because the formation of 2- and 3-methylpentane and 2,3-dimethylbutane is limited by equilibrium, the net reaction involves mainly the conversion of normal hexane to 2,2-dimethylbutane. All the feed benzene is hydrogenated to cyclohexane, and a thermodynamic equilibrium is established between methylcyclopentane and cyclohexane. The octane rating shows an appreciation of some 14 numbers.

PROCESS FLOW
As shown in Fig. 9.3.1, light naphtha feed is charged to one of the two dryer vessels. These vessels are filled with molecular sieves, which remove water and protect the catalyst. After mixing with makeup hydrogen, the feed is heat-exchanged against reactor effluent. It then enters a charge heater before entering the reactors. Two reactors normally operate in series. The reactor effluent is cooled before entering the product stabilizer. In new Penex designs, both the recycle gas compressor and the product separator have been eliminated. Only a slight excess of hydrogen above chemical consumption is used. The makeup hydrogen, which can be of any reasonable purity, is typically provided by a catalytic reformer. The stabilizer overhead vapors are caustic scrubbed for removal of the HCl formed from organic chloride added to the reactor feed to maintain catalyst activity. After scrubbing, the overhead gas then flows to fuel. The stabilized, isomerized liquid product from the bottom of the column then passes to gasoline blending. Alternatively, the stabilizer bottoms can be separated into normal and isoparaffin components by fractionation or molecular-sieve separation or a combination of the two methTABLE 9.3.1 Typical C5-C6 Chargestock and Product Compositions Percent of total C5 paraffins, wt %: Isopentane n-C5 C6 paraffins, wt %: 2,2-dimethylbutane 2,3-dimethylbutane Methylpentanes n-C6 C6 cyclic, wt %: Methylcyclopentane Cyclohexane Benzene Unleaded octane numbers: Research Motor 47.5 42.0 58.0 45.2 0.9 5.0 48.2 45.9 7.3 57.0 17.0 26.0 70.1 66.8 52.0 48.0 0 83.8 81.1 31.6 10.4 46.9 11.1 77.0 23.0 Chargestock Product

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FIGURE 9.3.1

UOP Penex process.

ods to obtain recycle of the normal paraffins and low-octane methylpentanes (MeC5). Product octanes in the range of 87 to 92 RON, clear, can be achieved by selecting one of the various possible schemes. The least capital-intensive recycle flow scheme is achieved by combining the Penex process with a deisohexanizer column. The deisohexanizer column concentrates the lowoctane methylpentanes into the sidecut stream. This sidecut stream combines with the fresh feed before entering the Penex reactor. The deisohexanizer column overhead, which is primarily isopentane, 2,2-dimethylbutane, and 2,3-dimethylbutane, is recovered for gasoline blending. A small bottoms drag stream, consisting of C6 naphthenes and C7s, is also removed from the deisohexanizer column and used for gasoline blending or as reformer feed. An efficient recycle operation is obtained by combining the Penex process with UOPs Molex* process, which uses molecular sieves to separate the stabilized Penex product into a high-octane isoparaffin stream and a low-octane normal paraffin stream. In this system, fresh feed together with the recovered low-octane normal paraffin stream is charged to the Penex unit. The isomerized product is denormalized in the Molex unit and recovered for gasoline blending. Many configurations of separation equipment are possible, as shown in Fig. 9.3.2. The optimum arrangement depends on the specific chargestock composition and the required product octane number. In addition to increasing octane, another benefit of all Penex-based flow schemes is the saturation of all benzene to cyclohexane. This aspect is particularly important to refiners who want to reduce the level of benzene in their gasoline pool. Some feedstocks, such as light reformate, can contain high levels of benzene. The performance of the Penex process can be compromised when processing these feedstocks because benzene hydrogenation is a highly exothermic reaction. The heat generated by the benzene hydrogenation reaction can cause the reactors to operate at conditions that are less favorable for octane upgrading. For these applications, UOP offers the Penex-Plus* process, which includes two reactor sections. The first section is designed to saturate the benzene to cyclohexane. The second section is designed to isomerize the feed for an overall octane increase. Each reactor is operated at conditions that favor the intended reactions for maximum conversion.
*Trademark and/or service mark of UOP.

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UOP PENEX PROCESS 9.18

ISOMERIZATION

FIGURE 9.3.2 Penex standard flow options.

UOP also offers the BenSat* process. This process is similar to the first reactor section of a Penex-Plus unit. Benzene is saturated to cyclohexane with no side reactions. A significant volumetric increase occurs with the BenSat process.

PROCESS APPLICATIONS
As mentioned earlier, the primary purpose of the Penex process is to improve the octane of LSR naphtha. The octane levels for a typical straight-run C5-C6 stock are characteristic of the various operating modes (Table 9.3.2).
*Trademark and/or service mark of UOP.

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If the required octane number can be met by recycle of the methylpentanes, the refiner probably would choose fractionation for capital reasons. Where the cost of utilities is high, the refiner might choose a Molex unit, which would separate both nC5 and nC6 for recycle. The utility cost would be lower for separating both of these in a Molex unit than it would be for separating the methylpentanes by fractionation, and the refiner would achieve a higher RON. Separation and recycle during paraffin isomerization are not new. Such options have been installed on many of the isomerization units in operation since the late 1980s. This change is a response to lead phaseout and benzene reduction in gasoline. The effect of lead elimination on the LSR portion of gasoline can be seen in Table 9.3.3. The octane improvement brought about by modern isomerization techniques can be broken down further. The C6 portion of the straight run is about 55 RON, clear, and this number is increased to 80 and 93 by once-through and recycle isomerization, respectively. The corresponding figures for the C5 fraction are 75, 86, and 93. The important figures, however, are the lead susceptibilities, or the difference between leaded and unleaded octane numbers. As shown in Table 9.3.3, the susceptibility of the entire pool is 7 RONs and that of the C5-C6 fraction is 17 to 18. These figures show the principal reason why no one was interested in C5-C6 isomerization prior to the worldwide movement toward lead elimination. The data show that once-through isomerization almost compensates for lead elimination in the LSR fraction and recycle isomerization more than makes up for it. To look at the figures another way, in a typical gasoline pool containing 10 percent LSR naphtha, isomerization provides a way of increasing the pool RON by 2 or more numbers with essentially no yield loss. Reformulated gasoline legislation in Europe and the United States is limiting aromatics concentrations in gasoline. Similar legislation is being enacted or is under considera-

TABLE 9.3.2

Typical Feed and Product Octane RON, clear

Charge Product Option 1: no recycle Option 2: recycle of 2- and 3-MeC5+nC6 Option 3: recycle of nC5+nC6 Option 4: recycle of nC5+nC6+2- and 3-MeC5
Note: RON research octane number.

69 83 88 89 92

TABLE 9.3.3

Lead Susceptibilities Octane number RON, clear RON + 0.6 g tetraethyl lead/L 96 8687 9697 101103

U.S. gasoline pool Straight-run pentane-hexane: Without isomerization Once-through isomerization Isomerized with maximum recycle

89 6870 8384 9293

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UOP PENEX PROCESS 9.20

ISOMERIZATION

tion in other parts of the world. This limitation on the aromaticity of gasoline further enhances the importance of high-octane aliphatic components such as alkylate and isomerized C5-C6.

THERMODYNAMIC EQUILIBRIUM CONSIDERATIONS, CATALYSTS, AND CHEMISTRY

Paraffin-isomerization catalysts fall mainly into two principal categories: those based on Friedel-Crafts catalysts as classically typified by aluminum chloride and hydrogen chloride and dual-functional hydroisomerization catalysts. The Friedel-Crafts catalysts represented a first-generation system. Although they permitted operation at low temperature, and thus a more favorable isomerization equilibrium, they lost favor because these systems were uneconomical and difficult to operate. High catalyst consumption and a relatively short life resulted in high maintenance costs and a low on-stream efficiency. These problems were solved with the development of second-generation dual-functional hydroisomerization catalysts. These catalysts included a metallic hydrogenation component in the catalyst and operated in a hydrogen environment. However, they had the drawback of requiring a higher operating temperature than the Friedel-Crafts systems. The desire to operate at lower temperatures, at which the thermodynamic equilibrium is more favorable, dictated the development of third-generation catalysts. The advantage of these low-temperature [below 200C (392F)] catalysts contributed to the relative nonuse of the high-temperature versions. Typically, these noble-metal, fixed-bed catalysts contain a component to provide high catalytic activity. They operate in a hydrogen environment and employ a promoter. Because hydrocracking of light gases is slight, liquid yields are high. The first of these catalysts was commercialized in 1959 in the UOP Butamer process for butane isomerization. An improved version of these third-generation catalysts is used in the Penex process. Paraffin isomerization is most effectively catalyzed by a dual-function catalyst containing a noble metal and an acid function. The reaction is believed to proceed through an olefin intermediate that is formed by the dehydrogenation of the paraffin on the metal site. The following reactions use butane for simplicity: CH3 CH2 CH2 CH3 CH3
Pt

CH2

CH

CH2

H2

(9.3.1)

The equilibrium conversion of paraffin is low at paraffin isomerization conditions. However, sufficient olefin must be present to convert a carbonium ion by the strong acid site: CH3 CH2 CH CH2 [H ][A ] CH3 CH2 CH CH3 A (9.3.2)

Through the formation of the carbonium ion, the olefin product is removed, and equilibrium is allowed to proceed. The carbonium ion in the second reaction undergoes skeletal isomerization, probably through a cycloalkyl intermediate: C CH3 H CH3 C C CH3 CH3 C CH3 (9.3.3)

CH3

CH2

CH

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This reaction proceeds with difficulty because it requires the formation of a primary carbonium ion at some point in the reaction. Nevertheless, the strong acidity of the isomerization catalyst provides enough driving force for the reaction to proceed at high rates. The isoparaffinic carbonium ion is then converted to an olefin through loss of a proton to the catalyst site: Ch3 Ch3 C Ch3 A Ch3 Ch3 C Ch2 [H ][A ] (9.3.4)

In the last step, the isoolefin intermediate is hydrogenated rapidly back to the analogous isoparaffin: CH3 Ch3 C Ch2 H2 Ch3 CH3 CH CH3 (9.3.5)

Equilibrium limits the maximum conversion possible at any given set of conditions. This maximum is a strong function of the temperature at which the conversion takes place. A more favorable equilibrium exists at lower temperatures. Figure 9.3.3 shows the equilibrium plot for the pentane system. The maximum isopentane content increases from 64 mol % at 260C to 82 mol % at 120C (248F). Neopentane and cyclopentane have been ignored because they seem to occur only in small quantities and are not formed under isomerization conditions. The hexane equilibrium curve shown in Fig. 9.3.4 is somewhat more complex than that shown in Fig. 9.3.3. The methylpentanes have been combined because they have nearly the same octane rating. The methylpentane content in the C6-paraffin fraction remains nearly constant over the entire temperature range. Similarly, the fraction of 2,3dimethylbutane is almost constant at about 9 mol % of the C6 paraffins. Theoretically, as the temperature is reduced, 2,2-dimethylbutane can be formed at the expense of normal hexane. This reaction is highly desirable because nC6 has a RON of 30. The RON of 2,2dimethylbutane is 93. Of course, the petroleum refiner is more interested in octane ratings than isomer distributions. Figure 9.3.5 shows the unleaded research octane ratings of equilibrium mixtures

FIGURE 9.3.3 C5 paraffin equilibrium plot.

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UOP PENEX PROCESS 9.22

ISOMERIZATION

FIGURE 9.3.4 C6 paraffin equilibrium plot.

FIGURE 9.3.5 Unleaded RON ratings of equilibrium fractions.

plotted against the temperature characteristic of that equilibrium for a typical chargestock. Both the C5 and the C6 paraffins show an increase in octane ratings as the temperature is reduced. Because equilibrium imposes a definite upper limit on the amount of desirable branched isomers that can exist in the reactor product, operating temperatures are thought to provide a simple basis for catalyst comparison or classification. However, temperature is only an approximate comparison that at best can discard a catalyst whose activity is so low that it might be operated at an unfavorably high temperature. Further, two catalysts that operate in the same general low-temperature range may differ in the closeness with which they can approach equilibrium in the presence of reasonable amounts of catalyst.

FEEDSTOCK REQUIREMENTS
To maintain the high activity of the Penex catalyst, the feedstock must be hydrotreated. However, costly prefractionation to sharply limit the levels of C6 cyclic and C7 compounds
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is not required. In fact, the Penex process affords the refiner with remarkably good flexibility in the choice of feedstocks, both at the time of design and even after the unit has been constructed. The latter is important because changes in the overall refinery processing scheme may occur in response to changing market situations. These changes could require that the composition of the isomerization feed be modified to achieve optimal results for the entire refinery. The Penex system can be applied to the processing of feeds containing up to 15 percent C7 with minimal or no effect on design requirements or operating performance. Generally, the best choice is to operate with lower levels of C7+ material because these compounds are better suited for upgrading in a reforming process. Charge containing about 5.0 percent or even higher amounts of benzene is completely acceptable in the Penex chargestock and will not produce carbon on the catalyst. When the feed has extremely high levels of benzene, a Penex-Plus unit is recommended. (The Plus section can be retrofitted to an existing Penex unit should the refiner want to process high-benzene feedstocks in an existing Penex unit.) The low-octane C6 cut recovered from raffinate derived from aromaticextraction operations typically contains a few percent of olefins and is completely acceptable as Penex feed without prehydrogenation. Sulfur is an undesirable constituent of the Penex feed. However, it is easily removed by conventional hydrotreating. Sulfur reduces the rate of isomerization and, therefore, the product octane number. Its effect is only temporary, however, and once it has been removed from the plant, the catalyst regains its normal activity. Water, other oxygen-containing compounds, and nitrogen compounds are the only impurities normally found in the feedstock that will irreversibly poison the Penex catalyst and shorten its life. Fresh feed and makeup hydrogen are dried by a simple, commercially proven desiccant system.

COMMERCIAL EXPERIENCE
Industry acceptance of the UOPs Penex process has been widespread. The first Penex unit was placed on-stream in 1958. By early 2002, more than 120 UOP Penex units had been commissioned, and more than 5 others were in engineering design or construction. A summary of typical commercial Penex unit yields, product properties, capital costs, utility requirements, and overall operating costs is presented in Tables 9.3.4 through 9.3.9.

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UOP PENEX PROCESS 9.24 TABLE 9.3.4

ISOMERIZATION

Typical Estimated Yields for Once-through Processing Reactor feed C4+ streams, BPD Reactor product

iC4 nC4 iC5 nC5 Cyclo-C5 2,2-dimethylbutane 2,3-dimethylbutane 2-methylpentane 3-methylpentane nC6 Methylcyclopentane Cyclo-C6 Benzene C7 Total

10 170 1,700 2,369 172 100 197 1,234 899 2,076 328 278 277 190 10,000 C4+ properties

109 159 3,215 940 121 1,565 473 1,502 761 477 290 279 0 164 10,136

Specific gravity Reid vapor pressure, kg/cm2 (lb/in2) Octane number RON, clear RON+3 cm3 tetraethyl lead/U.S. gal MON, clear MON+3 cm3 tetraethyl lead/U.S. gal Hydrogen consumption, SCF/day Light-gas yields, SCF/day C1 C2 C3

0.662 0.77 (10.9) 69.3 89.1 67.4 87.9

0.651 0.96 (13.7) 83.9 98.1 81.9 99.6 1,953,000 15,000 7,600 156,700

Note: BPD barrels per day; RON research octane number; MON motor octane number; SCF standard cubic feet; i and n indicate iso and normal forms, respectively.

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TABLE 9.3.5

Typical Estimated Yields: Penex with Molex Recycle* Fresh feed to reactor From Molex to reactor Stabilizer bottoms Isomerate product from Molex

Component

C4+ streams, BPD iC4 nC4 iC5 nC5 Cyclo-C5 2,2-dimethylbutane 2,3-dimethylbutane 2-methylpentane 3-methylpentane nC6 Methylcyclopentane Cyclo-C6 Benzene C7 Total 10 170 1,700 2,369 172 100 197 1,234 899 2,076 328 278 277 190 10,000 0 0 102 1,253 3 40 13 43 23 555 7 6 0 4 2,049 C4+ properties Specific gravity Reid vapor pressure, kg/cm2 (lb/in2) Octane number RON, clear RON+3 cm3 tetraethyl lead/U.S. gal MON, clear MON + 3 cm3 tetraethyl lead/U.S. gal Hydrogen consumption, SCF/day Light-gas yields, SCF/day: C1 C2 C3
*Basis: 10,000 BPD.

210 163 4,195 1,319 123 1,653 544 1,776 931 585 268 261 0 176 12,204

210 163 4,093 66 120 1,613 531 1,733 908 30 261 255 0 172 10,155

0.662 0.77 (10.9)

0.643 0.82 (11.7)

0.648 0.98 (13.9)

0.649 1.01 (14.4)

69.3 89.1 67.4 87.9

56.6 81.4 55.8 80.6

83.4 97.8 81.4 99.3

88.8 101.1 86.6 103.1 2,039,000

17,300 8,700 173,400

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TABLE 9.3.6

TABLE 9.3.6

Typical Estimated Yields of Penex with Deisohexanizer Sidecut Recycle

Component C4+ streams, bbl/day 0 0 0 0 0 59 369 1,743 1,282 856 443 285 0 177 5,214 C4+ properties 0.678 0.40 (5.7) 72.5 90.5 71.0 88.7 0.656 0.89 (12.6) 82.6 97.1 81.0 98.7 0.640 1.17 (16.7) 88.5 101.2 87.2 105.1 15,320 9,509 315 94 3,381 1,033 70 2,813 898 2,906 1,506 940 518 501 0 345 315 94 3,381 1,033 70 2,754 527 1,142 190 3 0 0 0 0

Fresh feed to reactor Stabilizer bottoms

From deisohexanizer to reactor

Isomerate product from deisohexanizer

Deisohexanizer drag

iC4 nC4 iC5 nC5 Cyclo-C5 2,2-dimethylbutane 2,3-dimethylbutane 2-methylpentane 3-methylpentane nC6 Methylcyclopentane Cyclo-C6 Benzene C7

2 49 2,433 1,885 100 57 222 1,532 992 1,487 561 179 195 306

0 0 0 0 0 0 2 20 35 82 76 216 0 168 599

UOP PENEX PROCESS

Total

10,000

0.661

0.724 0.25 (3.6) 77.0 90.8 69.9 85.3

0.80 (11.4)

73.2

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Specific gravity Reid vapor pressure, kg/cm2 (lb/in2) Octane number RON, clear RON+3 cm3 tetraethyl lead/U.S. gal MON, clear MON+3 cm3 tetraethyl lead/U.S. gal

91.4 71.1 90.5

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TABLE 9.3.7

Typical Penex Estimated Investment Costs Once-through, million $ U.S. Penex deisohexanizer, million $ U.S. 12.0 4.3 16.3
10,000 BPD.

Penex-Molex, million $ U.S. 18.2 6.3 24.5

Material and labor Design, engineering, and contractors expenses Total estimated erected cost of ISBL unit
Note: ISBL

6.5 2.7 9.2

inside battery limits; basis

TABLE 9.3.8

Typical Penex Estimated Utility Requirements* Options Once-through Penex deisohexanizer 975 12.0 (26.4) 24.2 (53.4) 262 (1153) PenexMolex 830 9.6 (21.2) 13.4 (29.6) 277 (1220)

Electric power, kW Medium-pressure steam usage (to condensate), 1000 kg/h (klb/h) Low-pressure steam usage (to condensate), 1000 kg/h (klb/h) Cooling water, m3/h (gal/min)
*Basis: 10,000 BPD.

375 9.4 (20.8) 136 (600)

TABLE 9.3.9

Typical Penex Estimated Operating Requirements* Oncethrough, million $ U.S. Penexdeisohexanizer, million $ U.S. 4.9 0.7 0.1 0.2 2.5 Penex- Molex, million $ U.S. 5.2 0.7 0.1 0.2 2.5

Initial catalyst, adsorbent, and noble metal inventory Annual catalyst and adsorbent costs Annual chemical cost Catalyst and chemical operating cost, $/bbl Number of operators
*Basis: 10,000 BPD and 2001 prices.

4.5 0.6 0.1 0.2 1.5

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UOP PENEX PROCESS

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