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Cost-Effective, Modular Technologies for Butane, Propane and NGL Treating

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Cost-Effective, Modular Technologies for Butane, Propane and NGL Treating Originally appeared in: Jan/Feb 2020, pgs 17-22. SPECIAL FOCUS: TREATING TECHNOLOGY Used with permission. Cost-effective, modular technologies for butane, propane and NGL treating D. B. ENGEL, S. WILLIAMS, H. BURNS and R. CROWE, Exion Systems, The Woodlands, Texas Hydrocarbon processing plants often Merichem’s Thiolex process utilizes a for example, mercaptans have a particu- encounter challenges with feedstocks con- chemical mechanism similar to the UOP larly foul odor. The change from a more taining high levels of mercaptans, which Merox process, with caustic extraction electronegative atom (oxygen) to sulfur concentrate in hydrocarbon condensates and regeneration via a catalytic oxidation also imparts to mercaptans a more acidic and NGL when the mercaptans are not stage to separate, transform and remove character compared to their alcohol coun- removed upstream by the acid gas removal mercaptans. It also has a liquid waste terparts due to the sulfur atom’s stabiliz- unit (AGRU) or molecular sieve unit. stream (dimethyl disulfide) that must be ing effect. Mercaptans, however, are only While hydrogen sulfide (H2S), as well as disposed of. This process system carries slightly acidic, and this acidity is reduced carbon dioxide (CO2), are removed by high capital expenses, similar to the UOP as the molecular weight of the mercaptan amine treating units, most will remove Merox system. Both systems are also sub- increases. FIG. 1 shows the molecular for- little to no mercaptans. Only when physi- ject to caustic waste disposal, and many mula and structural 3D model for one of cal solvents are used is removal possible.1,2 systems use a bleed and feed of fresh caus- the most common mercaptan contami- When NGL or condensates recovered tic to maintain a high pH. nants, methyl mercaptan (also named in gas processing contain high levels of Due to limited technologies to cost- methylthiol or methanethiol). mercaptans, off-spec fractionated prod- effectively treat hydrocarbon streams Relative to alcohols, mercaptans are ucts can occur, the hydrocarbon can have containing low-tonnage mercaptans and more acidic. Butyl mercaptan has a pKa of a negative odors and the value of the hy- H2S, one company set a goal to develop a 10.5 compared to 15 for butanol. Phenol drocarbon can be decreased, resulting in small and flexible system to address those mercaptan has a pKa of 6 compared to 10 loss of revenue. Additionally, the NGL, needs. As an alternative for large-scale for phenol. Therefore, mercaptanate (or condensate or its fractionated products systems, this company has developed a thiolate) salts can be created by treating often will not meet total sulfur or will fail systemb that is specifically designed to mercaptans with alkali hydroxides, such a quality test, such as a copper strip cor- treat hydrocarbon streams with less than 1 as sodium hydroxide or caustic. In fact, rosion test. tpd of mercaptans. These systems can be caustic is a common removal method for The two most commonly used tech- skid-mounted, are compact and require mercaptans in liquid streams (water and nologies for mercaptans removal are a minimal footprint. The technology has hydrocarbons). The chemical equations UOP’s Merox and Merichem’s Thiolex a chemical injection stage, followed by for the reaction of mercaptans (R-SH) systems. UOP’s Merox process utilizes a a proprietary contacting and separation and alcohols (R-OH) with sodium hy- proprietary catalyst, known simply as the process. The proprietary chemical con- droxide are indicated in Eqs. 1 and 2: Merox catalyst, along with heat and air to verts H2S, carbonyl sulfide (COS) and oxidize mercaptans to a disulfide in the mercaptans into stable, non-hazardous R-SH + NaOH → NaS-R + H2O regeneration stage. and water-soluble compounds. The spent (Forward reaction) (1) The Merox process is a demonstrated chemical is stable and easily disposed of R-OH + NaOH } NaO-R + H2O and proven process for mercaptans re- by any of several methods, depending on (Equilibrium reaction) (2) moval. However, the large capital expense the plant infrastructure. for these systems typically makes them In addition, mercaptans have weaker viable only for large-scale applications. H2S, mercaptans and mercaptans intermolecular forces. They show little as- The Merox process is generally used for removal. Mercaptans, or thiols, are a sociation by hydrogen bonding with water large-scale applications where caustic group of sulfur-based components that regeneration is required to make the op- are found in many hydrocarbon streams, erating economics viable. In addition, as mainly as an impurity. Mercaptans are part of the Merox process, a waste liquid similar to alcohols, but with the oxygen stream (dimethyl disulfide) is formed af- atom replaced by a sulfur atom. This ter caustic regeneration. Therefore, provi- change confers to mercaptan molecules sions must be taken for its proper disposal distinct chemical and physical properties. FIG. 1. Molecular structure (left) and molecular or reprocessing. Organoleptic properties are also affected; model (right) of methyl mercaptan. Gas Processing | JANUARY/FEBRUARY 2020 17 SPECIAL FOCUS: TREATING TECHNOLOGY From health, safety and process perspectives, cases, an odor release occurs. In some cas- es, the spent or rich caustic can be regener- the removal of mercaptans is often necessary. ated using a catalytic process and oxygen. Some mercaptans present strong odors. For this The oxygen regenerates the rich caustic so that it can be reused in the process; how- reason, mercaptans are used as odorizers in ever, it also produces a secondary disulfide consumer and commercial natural gas to alert oil (DSO) byproduct. Disulfides (also called red oil) are water-immiscible mate- to gas leaks. rials that can be a challenge for disposal in a gas plant. The chemical reactions for the molecules or among themselves. Mercap- lead to copper strip test failures under regenerative caustic removal of mercap- tans have lower boiling points and are less certain conditions. Mercaptans can nega- tans are indicated in Eqs. 5 and 6: soluble in water and other polar solvents tively affect catalysis and solid adsorption than alcohols of similar molecular weight. beds, such as silica gel or alumina, by com- 2 R-SH + 2 NaOH → 2 NaS-R + Mercaptans will hence have a higher-equi- peting for access to the same active sites. 2 H2O (Extractor reaction (5) librium vapor pressure and will be more Mercaptans removal is also necessary with excess NaOH) soluble in hydrocarbon phases. for reducing sulfur emissions, as com- 4 NaS-R + O2 + 2 H2O → Some mercaptans are also gaseous at bustion and emissions of mercaptans- 2 R-S-S-R (water immiscible ambient conditions in comparison to their containing compounds will lead to SOx DSO) + 4 Na+ + 4 OH– (6) oxygen analogues, due to their lower boil- formation. Mercaptans removal can be (Regeneration) ing point. One example is methyl mer- accomplished by a number of methods. captan (gas) in comparison to methanol The most common method utilized to- where R = hydrocarbon group. (liquid). The electronic configuration of day is the reaction with caustic (sodium Alternative products were developed mercaptans (namely the presence of d-or- hydroxide), shown earlier. Oxidation by especially for mercaptans removal. The bitals in sulfur atoms) provides them with a strong oxidant reagent (such as sodium concept was to use a nonregenerative highly interactive properties with many hypochlorite, oxygen and hydrogen per- mercaptans removal method where the surfaces (especially metals). This interac- oxide, among others) has also been used. waste or byproduct can be easily treated tion is the basis of some of the common The chemical reactions for mercaptans at low cost. This not only minimizes cap- metal surface friction reducers. Sulfur oxidation are indicated in Eqs. 3 and 4: ital costs but also reduces any post-treat- molecules can also serve in many instances ment costs. The reaction pathway does as metal ion chelants and metal stabilizers. 2 R-SH + ½ O2 → R-S-S-R + H2O not involve the use of caustic and elimi- From health, safety and process per- (Oxidation by oxygen) (3) nates the need for secondary treatments, spectives, the removal of mercaptans is R-SH + 3 H O → R-SO H such as regeneration of spent caustic or often necessary. Some mercaptans present 2 2 3 spent caustic disposal. The chemicalc is a + 3 H2O (Oxidation (4) strong odors and can cause serious disrup- by hydrogen peroxide) specialized polyhydric alcohol molecule, tions to daily life. In fact, humans are high- stabilized by hydroxyl materials, that ly sensitive to mercaptans at very low lev- Other methods for mercaptans remov- enables the removal of H2S, mercaptans els. For this reason, mercaptans are used al from hydrocarbon streams are available, and COS. The general chemical equa- as odorizers in consumer and commercial including oxidation using ozone, biologi- tion for the reaction with mercaptans is natural gas to alert to gas leaks. Some mer- cal removal processes, catalytic decom- shown in Eq. 7: captans can cause corrosion, and often position, adsorption into solid beds (i.e., R-SH + CA → R-S-S-R + functionalized activated carbon) and spe- –2 R-S-SO-R + R-R + SO4 + (7) Treated hydrocarbon stream cialized solvents. However, only the latter H O (Oxidative coupling) two methods are commonly used in the 2 Extractor Caustic and disulfides industry. The use of sodium hydroxide for where R-S-SO-R = sulfoxide species Excess air mercaptans removal is perhaps the most (water soluble and does not affect the common worldwide. process). Disulfides Air The reaction with caustic is effective, The reactions show that water, sulfate Oxidizer –2 Feed but is also a reversible equilibrium. So- (SO4 ) and other oxidized components hydrocarbon dium hydroxide is readily available at low are products of the reaction. The water- stream Disulfide cost.
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