854:
122:
215:
1263:
2124:
977:
769:(ULSD), in turn requires that very deep hydrodesulfurization is needed. In the very early 2000s, the governmental regulatory limits for highway vehicle diesel was within the range of 300 to 500 ppm by weight of total sulfur. As of 2006, the total sulfur limit for highway diesel is in the range of 15 to 30 ppm by weight.
604:
The hot reaction products are partially cooled by flowing through the heat exchanger where the reactor feed was preheated and then flows through a water-cooled heat exchanger before it flows through the pressure controller (PC) and undergoes a pressure reduction down to about 3 to 5 atmospheres. The
849:
crystallites, the molybdenum centre can stabilize a coordinatively unsaturated site (CUS), also known as an anion vacancy. Substrates, such as thiophene, bind to this site and undergo a series of reactions that result in both C-S scission and C=C hydrogenation. Thus, the hydrogen serves multiple
517:
1416:
1258:{\displaystyle {\ce {{\overset {Pyridine}{C5H5N}}+ {\overset {Hydrogen}{5H2}}-> {\overset {Piperdine}{C5H11N}}+ {\overset {Hydrogen}{2H2}}-> {\overset {Amylamine}{C5H11NH2}}+ {\overset {Hydrogen}{H2}}-> {\overset {Pentane}{C5H12}}+ {\overset {Ammonia}{NH3}}}}}
759:
When the HDS process is used to desulfurize a refinery naphtha, it is necessary to remove the total sulfur down to the parts per million range or lower in order to prevent poisoning the noble metal catalysts in the subsequent catalytic reforming of the naphthas.
275:) was commercialized. At the same time, the catalytic hydrodesulfurization of the naphtha feed to such reformers was also commercialized. In the decades that followed, various proprietary catalytic hydrodesulfurization processes, such as the one depicted in the
1560:
1565:
Some hydrogenolysis units within a petroleum refinery or a petrochemical plant may be used solely for the saturation of olefins or they may be used for simultaneously desulfurizing as well as denitrogenating and saturating olefins to some extent.
688:
or heavier components. The residual hydrogen, methane, ethane, and some propane is used as refinery fuel gas. The hydrogen sulfide removed and recovered by the amine gas treating unit is subsequently converted to elemental sulfur in a
588:
The liquid feed (at the bottom left in the diagram) is pumped up to the required elevated pressure and is joined by a stream of hydrogen-rich recycle gas. The resulting liquid-gas mixture is preheated by flowing through a
368:
1826:
Chianelli, R. R.; Berhault, G.; Raybaud, P.; Kasztelan, S.; Hafner, J. and
Toulhoat, H., "Periodic trends in hydrodesulfurization: in support of the Sabatier principle", Applied Catalysis, A, 2002, volume 227, pages
1274:
708:. If the feed does contain olefins (for example, the feed is a naphtha derived from a refinery fluid catalytic cracker (FCC) unit), then the overhead gas from the HDS stripper may also contain some
1953:
922:
that is catalytically active. The interaction between the support and the catalyst is an area of intense interest, since the support is often not fully inert but participates in the catalysis.
222:
Although some reactions involving catalytic hydrogenation of organic substances were already known, the property of finely divided nickel to catalyze the fixation of hydrogen on hydrocarbon (
1945:
1979:
1450:
199:). In fact, the vast majority of the 64,000,000 metric tons of sulfur produced worldwide in 2005 was byproduct sulfur from refineries and other hydrocarbon processing plants.
581:
601:
and heated to the required elevated temperature before entering the reactor and flowing through a fixed-bed of catalyst where the hydrodesulfurization reaction takes place.
971:), a nitrogen compound present in some petroleum fractionation products, as an example, the hydrodenitrogenation reaction has been postulated as occurring in three steps:
752:, and many others. These organic sulfur compounds are products of the degradation of sulfur containing biological components, present during the natural formation of the
574:(called NiMo) is used, in addition to the CoMo catalyst, for specific difficult-to-treat feed stocks, such as those containing a high level of chemically bound nitrogen.
264:
in the liquid phase into saturated ones. He was awarded a patent in
Germany in 1902 and in Britain in 1903, which was the beginning of what is now a worldwide industry.
821:) together with smaller amounts of other metals. The nature of the sites of catalytic activity remains an active area of investigation, but it is generally assumed
336:(O) atom. The net result of a hydrogenolysis reaction is the formation of C-H and H-X chemical bonds. Thus, hydrodesulfurization is a hydrogenolysis reaction. Using
763:
When the process is used for desulfurizing diesel oils, the latest environmental regulations in the United States and Europe, requiring what is referred to as
797:
is considered the most challenging substrates. Benzothiophenes are midway between the simple thiophenes and dibenzothiophenes in their susceptibility to HDS.
2070:
724:, or heavier components. The amine solution to and from the recycle gas contactor comes from and is returned to the refinery's main amine gas treating unit.
2065:
680:
and heavier components. That sour gas is sent to the refinery's central gas processing plant for removal of the hydrogen sulfide in the refinery's main
1817:
Daage, M.; Chianelli, R. R., "Structure-Function
Relations in Molybdenum Sulfide Catalysts - the Rim-Edge Model", J. of Catalysis, 1994, 149, 414-427.
512:{\displaystyle {\ce {{\overset {Ethanethiol}{C2H5SH}}+{\overset {Hydrogen}{H2}}->{\overset {Ethane}{C2H6}}+{\overset {Hydrogen\ sulfide}{H2S}}}}}
1959:
1839:"Recent developments in alumina supported hydrodesulfurization catalysts for the production of sulfur-free refinery products: A technical review"
1607:"Recent developments in alumina supported hydrodesulfurization catalysts for the production of sulfur-free refinery products: A technical review"
1411:{\displaystyle {\ce {{\overset {Pyridine}{C5H5N}}+ {\overset {Hydrogen}{5H2}}-> {\overset {Pentane}{C5H12}}+ {\overset {Ammonia}{NH3}}}}}
1986:
1421:
Many HDS units for desulfurizing naphthas within petroleum refineries are actually simultaneously denitrogenating to some extent as well.
850:
roles—generation of anion vacancy by removal of sulfide, hydrogenation, and hydrogenolysis. A simplified diagram for the cycle is shown:
1676:
1933:
642:-free hydrogen-rich gas is then recycled back for reuse in the reactor section. Any excess gas from the gas separator vessel joins the
362:), a sulfur compound present in some petroleum products, as an example, the hydrodesulfurization reaction can be simply expressed as
534:
In an industrial hydrodesulfurization unit, such as in a refinery, the hydrodesulfurization reaction takes place in a fixed-bed
1879:
Kinetics and
Interactions of the Simultaneous Catalytic Hydrodenitrogenation of Pyridine and Hydrodesulfurization of Thiophene
2040:
1659:
279:
below, have been commercialized. Currently, virtually all of the petroleum refineries worldwide have one or more HDS units.
1808:
Topsøe, H.; Clausen, B. S.; Massoth, F. E., Hydrotreating
Catalysis, Science and Technology, Springer-Verlag: Berlin, 1996.
938:
The hydrogenolysis reaction is also used to reduce the nitrogen content of a petroleum stream in a process referred to as
2128:
1430:
910:. The support allows the more expensive catalyst to be more widely distributed, giving rise to a larger fraction of the
777:
A family of substrates that are particularly common in petroleum are the aromatic sulfur-containing heterocycles called
2045:
577:
The image below is a schematic depiction of the equipment and the process flow streams in a typical refinery HDS unit.
657:
tower. The bottoms product from the stripper is the final desulfurized liquid product from hydrodesulfurization unit.
1585:
1777:
1939:
2159:
1894:(Satterfield, C.N., Modell, M. and Wilkens, J.A., Ind. Eng. Chem. Process Des. Dev., 1980 Vol. 19, pages 154-160
1703:
1917:
853:
1555:{\displaystyle {\ce {{\overset {Pentene}{C5H10}}+ {\overset {Hydrogen}{H2}}-> {\overset {Pentane}{C5H12}}}}}
249:
by using hydrogen and a catalytic metal, laying the foundation of the modern catalytic hydrogenation process.
164:
The industrial hydrodesulfurization processes include facilities for the capture and removal of the resulting
781:. Many kinds of thiophenes occur in petroleum ranging from thiophene itself to more condensed derivatives,
794:
1699:
2154:
1972:
1754:
890:
are also used, depending on the nature of the feed. For example, Ni-W catalysts are more effective for
837:
structure are not relevant to catalysis, rather the edges or rims of these sheet. At the edges of the
612:
Most of the hydrogen-rich gas from the gas separator vessel is recycle gas, which is routed through an
732:
The refinery HDS feedstocks (naphtha, kerosene, diesel oil, and heavier oils) contain a wide range of
2080:
1950:
by E.S. Jang, M.Y. Jung, D.B. Min, Comprehensive
Reviews in Food Science and Food Safety, Vol.1, 2005
1743:
694:
111:
793:
itself and its alkyl derivatives are easier to hydrogenolyse, whereas dibenzothiophene, especially
242:
20:
765:
654:
238:
80:
2011:
1877:
1765:
246:
1837:
Shafiq, Iqrash; Shafique, Sumeer; Akhter, Parveen; Yang, Wenshu; Hussain, Murid (2020-06-23).
1605:
Shafiq, Iqrash; Shafique, Sumeer; Akhter, Parveen; Yang, Wenshu; Hussain, Murid (2020-06-23).
297:. By 2007, this had been integrated into an operating 5 kW fuel cell generation system.
2149:
2075:
1892:
Simultaneous
Catalytic Hydrodenitrogenation of Pyridine and Hydrodesulfurization of Thiophene
1683:
2090:
939:
891:
806:
276:
8:
2055:
871:
272:
154:
930:
The basic hydrogenolysis reaction has a number of uses other than hydrodesulfurization.
522:
For the mechanistic aspects of, and the catalysts used in this reaction see the section
2105:
2050:
1995:
1794:
1714:
1651:
681:
613:
594:
309:
138:
134:
584:
Schematic diagram of a typical hydrodesulfurization (HDS) unit in a petroleum refinery
1860:
1655:
1628:
684:
unit and through a series of distillation towers for recovery of propane, butane and
547:
294:
130:
1895:
1850:
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903:
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733:
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165:
1855:
1838:
1623:
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2164:
2060:
1921:
698:
606:
253:
48:
1799:
published online by the
National Petrochemical & Refiners Association (NPRA)
1444:
As an example, the saturation of the olefin pentene can be simply expressed as:
878:
and molybdenum are also highly active. Aside from the basic cobalt-modified MoS
1580:
782:
590:
317:
84:
906:
on materials with high surface areas. A typical support for HDS catalyst is γ-
202:
An HDS unit in the petroleum refining industry is also often referred to as a
2143:
2085:
1864:
1632:
1575:
690:
321:
305:
185:
158:
1942:(Engineering design and construction of large-scale, industrial HDS plants)
704:
Note that the above description assumes that the HDS unit feed contains no
539:
283:
177:
56:
874:
appears to be the single most active catalyst, but binary combinations of
256:, found that catalytic hydrogenation could be used to convert unsaturated
180:, the hydrogen sulfide gas is then subsequently converted into byproduct,
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1781:
822:
753:
337:
268:
257:
231:
142:
103:
72:
52:
1899:
2100:
778:
749:
741:
571:
563:
261:
115:
16:
Chemical process used to remove sulfur in natural gas and oil refining
2006:
1964:
790:
598:
543:
291:
44:
1914:
79:. The purpose of removing the sulfur, and creating products such as
2035:
946:
887:
745:
721:
650:
643:
551:
329:
313:
223:
146:
99:
95:
76:
68:
64:
60:
566:(usually called a CoMo catalyst). Occasionally, a combination of
320:
is a type of hydrogenation and results in the cleavage of the C-X
1438:
1434:
907:
717:
713:
705:
685:
673:
661:
609:
at about 35 °C and 3 to 5 atmospheres of absolute pressure.
555:
235:
227:
150:
1778:"Fuel cells help make noisy, hot generators a thing of the past"
883:
875:
866:
Most metals catalyse HDS, but it is those at the middle of the
737:
709:
677:
665:
567:
559:
333:
325:
181:
114:, residential and industrial furnaces, and other forms of fuel
727:
214:
121:
942:(HDN). The process flow is the same as that for an HDS unit.
649:
The liquid from the gas separator vessel is routed through a
605:
resulting mixture of liquid and gas enters the gas separator
107:
94:) emissions that result from using those fuels in automotive
1947:
Hydrogenation for Low Trans and High
Conjugated Fatty Acids
660:
The overhead sour gas from the stripper contains hydrogen,
580:
287:
1542:
1529:
1505:
1481:
1468:
1399:
1375:
1362:
1337:
1305:
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1246:
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1135:
1110:
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1008:
995:
488:
463:
450:
426:
399:
386:
1927:
1836:
1645:
1604:
1780:. Pacific Northwest National Laboratory. Archived from
1682:. Mexico City: Trans Energy Associates. Archived from
870:
series that are most active. Although not practical,
137:
is that sulfur, even in extremely low concentrations,
129:
Another important reason for removing sulfur from the
1453:
1277:
1268:
and the overall reaction may be simply expressed as:
980:
550:
of absolute pressure, typically in the presence of a
371:
1744:
DE Patent DE141029 (Espacenet, record not available)
1441:. The process used is the same as for an HDS unit.
646:from the stripping of the reaction product liquid.
1554:
1410:
1257:
511:
2141:
1429:The hydrogenolysis reaction may also be used to
157:units that are subsequently used to upgrade the
1674:
857:Simplified diagram of a HDS cycle for thiophene
252:Soon after Sabatier's work, a German chemist,
1980:
1956:(Engineered and constructed by Aker Kvaerner)
1755:UK Patent GB190301515 GB190301515 (Espacenet)
1677:"Hydrodesulfurization Technologies and Costs"
542:ranging from 300 to 400 °C and elevated
523:
286:HDS units had been implemented for treating
1648:Petroleum Refining Technology and Economics
800:
728:Sulfur compounds in refinery HDS feedstocks
312:in which the net result is the addition of
290:jet fuel to produce clean feed stock for a
245:in the vapor phase could be converted into
241:in 1897. Through this work, he found that
1987:
1973:
593:. The preheated feed then flows through a
218:Hydrodesulfurization, hydrodenitrogenation
1960:Catalysts and technology for Oxo-Alcohols
1854:
1622:
1326:
1099:
1029:
1715:Discussion of recovered byproduct sulfur
1424:
852:
579:
213:
120:
933:
125:Hydrodesulfurization unit in a refinery
2142:
1994:
529:
2024:
1968:
2123:
805:The main HDS catalysts are based on
616:for removal of the reaction product
300:
1924:(Hydroprocessing Catalyst Supplier)
1882:(John Wilkins, PhD Thesis, ], 1977)
1646:Gary, J.H.; Handwerk, G.E. (1984).
1639:
13:
1936:(Petrochemical catalysts supplier)
597:where the feed mixture is totally
14:
2176:
1908:
1586:Timeline of hydrogen technologies
271:catalytic reforming process (the
2122:
1675:Nancy Yamaguchi (May 29, 2003).
47:chemical process widely used to
1885:
1871:
1830:
1820:
1811:
1802:
1788:
1770:
1759:
1704:United States Geological Survey
1748:
1737:
1728:
1719:
1708:
1693:
1668:
1598:
1513:
1346:
1193:
1119:
1049:
693:unit or to sulfuric acid in a
434:
1:
2025:
1856:10.1080/01614940.2020.1780824
1766:Microchannel HDS (March 2006)
1624:10.1080/01614940.2020.1780824
1591:
925:
772:
234:was discovered by the French
1734:C.R.Acad.Sci. 1901, 132, 210
1725:C.R.Acad.Sci. 1897, 132, 210
861:
795:4,6-dimethyldibenzothiophene
736:sulfur compounds, including
328:atom and X is a sulfur (S),
267:In the mid-1950s, the first
7:
1569:
897:
10:
2181:
1934:Albemarle Catalyst Company
1930:(Catalyzing Your Business)
209:
57:refined petroleum products
18:
2118:
2031:
2020:
2002:
695:wet sulfuric acid process
2041:Atmospheric distillation
1700:Sulfur production report
801:Catalysts and mechanisms
524:catalysts and mechanisms
243:unsaturated hydrocarbons
161:of the naphtha streams.
21:Flue-gas desulfurization
19:Not to be confused with
766:ultra-low-sulfur diesel
756:, petroleum crude oil.
697:or in the conventional
546:ranging from 30 to 130
81:ultra-low-sulfur diesel
2160:Natural gas technology
2012:List of oil refineries
1556:
1412:
1259:
858:
629:that it contains. The
585:
558:base impregnated with
513:
247:saturated hydrocarbons
219:
126:
2076:Hydrodesulphurisation
1557:
1425:Saturation of olefins
1413:
1260:
856:
676:, and, perhaps, some
583:
514:
217:
124:
110:, gas or oil burning
2091:Solvent deasphalting
1784:on 15 December 2007.
1689:on October 13, 2006.
1451:
1275:
978:
940:hydrodenitrogenation
934:Hydrodenitrogenation
892:hydrodenitrogenation
807:molybdenum disulfide
369:
178:petroleum refineries
29:Hydrodesulfurization
2056:Catalytic reforming
2046:Vacuum distillation
1915:Criterion Catalysts
1900:10.1021/i260073a027
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902:Metal sulfides are
872:ruthenium disulfide
530:Process description
490:
465:
452:
428:
401:
388:
282:By 2006, miniature
155:catalytic reforming
83:, is to reduce the
2155:Chemical processes
2106:Amine gas treating
2051:Catalytic cracking
1996:Petroleum refining
1920:2018-12-07 at the
1652:Marcel Dekker, Inc
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273:Platformer process
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61:gasoline or petrol
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1843:Catalysis Reviews
1661:978-0-8247-7150-8
1611:Catalysis Reviews
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787:dibenzothiophenes
554:consisting of an
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1954:Oxo Alcohols
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1891:
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595:fired heater
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540:temperatures
538:at elevated
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284:microfluidic
281:
277:flow diagram
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232:double bonds
221:
204:hydrotreater
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112:power plants
40:
36:
32:
28:
27:
25:
2096:Visbreaking
1849:(1): 1–86.
1617:(1): 1–86.
1433:or convert
754:fossil fuel
548:atmospheres
407:Ethanethiol
338:ethanethiol
269:noble metal
258:fatty acids
145:catalysts (
143:noble metal
104:locomotives
102:, railroad
73:diesel fuel
53:natural gas
2144:Categories
2081:Sweetening
2061:Alkylation
1592:References
926:Other uses
882:catalyst,
779:thiophenes
773:Thiophenes
750:disulfides
744:, organic
742:thiophenes
572:molybdenum
564:molybdenum
262:glycerides
176:) gas. In
116:combustion
59:, such as
2036:Desalting
2026:Processes
2007:Petroleum
1865:0161-4940
1633:0161-4940
1514:⟶
1347:⟶
1194:⟶
1166:Amylamine
1120:⟶
1086:Piperdine
1050:⟶
904:supported
862:Catalysts
791:Thiophene
653:stripper
599:vaporized
544:pressures
435:⟶
292:fuel cell
153:) in the
77:fuel oils
55:and from
51:(S) from
45:catalytic
1918:Archived
1570:See also
1509:Hydrogen
1431:saturate
1342:Hydrogen
1313:Pyridine
1189:Hydrogen
1115:Hydrogen
1045:Hydrogen
1016:Pyridine
947:pyridine
898:Supports
888:tungsten
746:sulfides
722:pentenes
651:reboiled
644:sour gas
552:catalyst
497:Hydrogen
430:Hydrogen
330:nitrogen
314:hydrogen
224:ethylene
147:platinum
100:aircraft
96:vehicles
69:kerosene
65:jet fuel
2129:Commons
1702:by the
1547:Pentane
1486:Pentene
1439:alkanes
1435:alkenes
1403:Ammonia
1380:Pentane
1250:Ammonia
1227:Pentane
908:alumina
825:of the
734:organic
718:butenes
714:propene
706:olefins
686:pentane
674:propane
662:methane
556:alumina
536:reactor
503:sulfide
332:(N) or
236:chemist
228:benzene
210:History
184:(S) or
151:rhenium
139:poisons
131:naphtha
43:, is a
2165:Sulfur
2127:
2101:Coking
1863:
1827:83-96.
1658:
1631:
945:Using
884:nickel
876:cobalt
738:thiols
710:ethene
678:butane
666:ethane
568:nickel
560:cobalt
500:
468:Ethane
334:oxygen
326:carbon
182:sulfur
75:, and
1687:(PDF)
1680:(PDF)
1437:into
316:(H).
108:ships
1861:ISSN
1656:ISBN
1629:ISSN
886:and
785:and
748:and
720:and
570:and
562:and
288:JP-8
149:and
141:the
1896:doi
1851:doi
1619:doi
912:MoS
839:MoS
827:MoS
811:MoS
260:or
39:or
33:HDS
2146::
1859:.
1847:64
1845:.
1841:.
1654:.
1627:.
1615:64
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1609:.
1538:12
1477:10
1391:NH
1371:12
1238:NH
1218:12
1153:NH
1144:11
1074:11
894:.
789:.
740:,
716:,
712:,
701:.
672:,
668:,
664:,
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403:SH
360:SH
230:)
226:,
206:.
194:SO
118:.
106:,
98:,
89:SO
71:,
67:,
63:,
1988:e
1981:t
1974:v
1898::
1867:.
1853::
1664:.
1635:.
1621::
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1525:5
1521:C
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1497:H
1491:+
1473:H
1464:5
1460:C
1395:3
1385:+
1367:H
1358:5
1354:C
1333:2
1329:H
1324:5
1318:+
1309:N
1301:5
1297:H
1288:5
1284:C
1242:3
1232:+
1214:H
1205:5
1201:C
1181:2
1177:H
1171:+
1157:2
1140:H
1131:5
1127:C
1106:2
1102:H
1097:2
1091:+
1082:N
1070:H
1061:5
1057:C
1036:2
1032:H
1027:5
1021:+
1012:N
1004:5
1000:H
991:5
987:C
969:N
965:5
960:H
956:5
951:C
949:(
917:2
880:2
844:2
832:2
816:2
809:(
640:S
636:2
631:H
627:S
623:2
618:H
492:S
484:2
480:H
473:+
459:6
455:H
446:2
442:C
422:2
418:H
412:+
395:5
391:H
382:2
378:C
356:5
351:H
347:2
342:C
340:(
196:4
192:2
190:H
188:(
174:S
172:2
170:H
168:(
91:2
87:(
31:(
23:.
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