CA1122553A - Process for the separation of aromatic compounds from hydrocarbon mixtures - Google Patents

Process for the separation of aromatic compounds from hydrocarbon mixtures

Info

Publication number: CA1122553A
Authority: CA; Canada
Prior art keywords: adsorbent; aromatic compounds; hydro; organic solvent; mixture
Prior art date: 1977-10-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA311,125A

Other languages

English (en)

French (fr)

Inventor

Guy Barre

Roland Quillet

Emmanuel Neel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-10-07

Filing date

1978-09-12

Publication date

1982-04-27

1978-09-12 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1982-04-27 Application granted granted Critical

1982-04-27 Publication of CA1122553A publication Critical patent/CA1122553A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 37
239000000203 mixture Substances 0.000 title claims abstract description 31
229930195733 hydrocarbon Natural products 0.000 title claims abstract description 29
150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 29
239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 28
150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 28
238000000926 separation method Methods 0.000 title claims abstract description 8
239000007791 liquid phase Substances 0.000 claims abstract description 6
229940100890 silver compound Drugs 0.000 claims abstract description 5
150000003379 silver compounds Chemical class 0.000 claims abstract description 5
239000007787 solid Substances 0.000 claims abstract description 4
239000003463 adsorbent Substances 0.000 claims description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
238000004517 catalytic hydrocracking Methods 0.000 claims description 13
229910052709 silver Inorganic materials 0.000 claims description 10
239000004332 silver Substances 0.000 claims description 10
239000003208 petroleum Substances 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
239000000377 silicon dioxide Substances 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
239000012188 paraffin wax Substances 0.000 claims 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
125000004185 ester group Chemical group 0.000 claims 1
125000001033 ether group Chemical group 0.000 claims 1
125000000468 ketone group Chemical group 0.000 claims 1
239000003921 oil Substances 0.000 abstract description 29
230000002745 absorbent Effects 0.000 abstract 2
239000002250 absorbent Substances 0.000 abstract 2
230000008929 regeneration Effects 0.000 description 12
238000011069 regeneration method Methods 0.000 description 12
238000009835 boiling Methods 0.000 description 10
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
238000001179 sorption measurement Methods 0.000 description 9
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000000047 product Substances 0.000 description 8
239000010687 lubricating oil Substances 0.000 description 7
239000011148 porous material Substances 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229910001961 silver nitrate Inorganic materials 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
-1 aromatic compounds Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000001117 sulphuric acid Substances 0.000 description 4
235000011149 sulphuric acid Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000001354 calcination Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000012263 liquid product Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
206010042496 Sunburn Diseases 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052755 nonmetal Inorganic materials 0.000 description 1
150000002843 nonmetals Chemical class 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000005325 percolation Methods 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002987 phenanthrenes Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003220 pyrenes Chemical class 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
150000003378 silver Chemical class 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical class [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000011275 tar sand Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/06—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including a sorption process as the refining step in the absence of hydrogen
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/003—Specific sorbent material, not covered by C10G25/02 or C10G25/03
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/12—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including cracking steps and other hydrotreatment steps

Landscapes

Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CA311,125A 1977-10-07 1978-09-12 Process for the separation of aromatic compounds from hydrocarbon mixtures Expired CA1122553A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7730263		1977-10-07
FR7730263A FR2405290A1 (fr)	1977-10-07	1977-10-07	Procede pour la separation d'hydrocarbures aromatiques de melanges d'hydrocarbures contenant des aromatiques

Publications (1)

Publication Number	Publication Date
CA1122553A true CA1122553A (en)	1982-04-27

Family

ID=9196253

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA311,125A Expired CA1122553A (en)	1977-10-07	1978-09-12	Process for the separation of aromatic compounds from hydrocarbon mixtures

Country Status (8)

Country	Link
JP (1)	JPS5461127A (it)
BE (1)	BE870877A (it)
CA (1)	CA1122553A (it)
DE (1)	DE2843536A1 (it)
FR (1)	FR2405290A1 (it)
GB (1)	GB2005299B (it)
IT (1)	IT1099766B (it)
NL (1)	NL7810049A (it)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2918867C2 (de) *	1979-05-10	1987-03-19	Robert Bosch Gmbh, 7000 Stuttgart	Kraftstoffeinspritzpumpe für Brennkraftmaschinen mit einer Steuereinrichtung für die Änderung des Förderbeginns
JPS5689058A (en) *	1979-12-21	1981-07-20	Toyo Soda Mfg Co Ltd	Method for analyzing hydrocarbon compound
US4447315A (en) *	1983-04-22	1984-05-08	Uop Inc.	Hydrocracking process
US4808300A (en) *	1987-02-13	1989-02-28	Exxon Research And Engineering Company	Simultaneous removal of aromatics and wax from lube distillate by an adsorption process
JP2636090B2 (ja) *	1991-04-18	1997-07-30	出光興産株式会社	硝酸銀含浸シリカゲルの製造方法
US5282960A (en) *	1991-10-02	1994-02-01	Exxon Research And Engineering Company	Method for improving the demulsibility of base oils
IT1277680B1 (it) *	1995-12-21	1997-11-11	Enichem Spa	Procedimento per l'alchilazione di composti aromatici
US7053256B2 (en)	2001-09-04	2006-05-30	The Regents Of The University Of Michigan	Selective sorbents for purification of hydrocarbons
US7094333B2 (en)	2001-09-04	2006-08-22	The Regents Of The University Of Michigan	Selective sorbents for purification of hydrocarbons
US7029574B2 (en)	2002-09-04	2006-04-18	The Regents Of The University Of Michigan	Selective sorbents for purification of hydrocarbons
US7148389B2 (en)	2001-09-04	2006-12-12	The Regents Of The University Of Michigan	Selective sorbents for purification of hydrocartons
US7594991B2 (en)	2007-12-28	2009-09-29	Exxonmobil Research And Engineering Company	All catalytic medicinal white oil production
JP6131443B2 (ja) *	2012-10-17	2017-05-24	株式会社島津製作所	分離媒体、その分離媒体を用いたカラム、そのカラムを備えた液体クロマトグラフ、及びその分離媒体の製造方法
CA2968897A1 (en) *	2014-12-30	2016-07-07	Exxonmobil Research And Engineering Company	Catalytic and solvent processing for base oil production
CN114832786B (zh) *	2022-05-09	2024-05-03	中海油天津化工研究设计院有限公司	一种用于馏分油吸附精馏耦合脱芳工艺的吸附剂及制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3150079A (en) *	1960-07-13	1964-09-22	Exxon Research Engineering Co	Separation by selective desorption of silica gel
US3895080A (en) *	1972-06-06	1975-07-15	Sun Research Development	Separation of cyclic compounds by adsorption on partially sorbed metallic zeolites
DE2364333C3 (de) *	1973-12-22	1979-10-11	Deutsche Texaco Ag, 2000 Hamburg	Verfahren zur Abtrennung von aromatischen Kohlenwasserstoffen aus n-Paraffingemischen durch Behandlung mit einem wasserfreien makroporösen Kationenaustauscherharz

1977
- 1977-10-07 FR FR7730263A patent/FR2405290A1/fr active Granted
1978
- 1978-09-12 CA CA311,125A patent/CA1122553A/en not_active Expired
- 1978-09-29 BE BE1009079A patent/BE870877A/xx not_active IP Right Cessation
- 1978-10-05 JP JP12210278A patent/JPS5461127A/ja active Granted
- 1978-10-05 DE DE19782843536 patent/DE2843536A1/de active Granted
- 1978-10-05 NL NL7810049A patent/NL7810049A/xx not_active Application Discontinuation
- 1978-10-05 GB GB7839431A patent/GB2005299B/en not_active Expired
- 1978-10-05 IT IT28461/78A patent/IT1099766B/it active

Also Published As

Publication number	Publication date
DE2843536C2 (it)	1989-01-26
DE2843536A1 (de)	1979-04-19
JPS5461127A (en)	1979-05-17
JPS6210278B2 (it)	1987-03-05
FR2405290B1 (it)	1980-05-16
GB2005299B (en)	1982-02-17
IT7828461A0 (it)	1978-10-05
FR2405290A1 (fr)	1979-05-04
BE870877A (nl)	1979-03-29
IT1099766B (it)	1985-09-28
GB2005299A (en)	1979-04-19
NL7810049A (nl)	1979-04-10

Legal Events

Date	Code	Title	Description
1999-04-27	MKEX	Expiry

Publication	Publication Date	Title
US5378351A (en)	1995-01-03	Process for the preparation of lubricating base oils
CA1122553A (en)	1982-04-27	Process for the separation of aromatic compounds from hydrocarbon mixtures
US4594172A (en)	1986-06-10	Process for the preparation of hydrocarbons
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US3239451A (en)	1966-03-08	Hydrocracking process with a crystalline zeolite catalyst composite activated with hydrogen sulfide