CA1083609A - Hydroalkylation of benzene and analogs - Google Patents

Hydroalkylation of benzene and analogs

Info

Publication number: CA1083609A
Authority: CA; Canada
Prior art keywords: catalyst; promoter; benzene; mono; rare earth
Prior art date: 1976-12-20
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

CA293,319A

Other languages

English (en)

French (fr)

Inventor

Serge R. Dolhyj

Louis J. Velenyi

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.)

Individual

Original Assignee

Individual

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.)

1976-12-20

Filing date

1977-12-19

Publication date

1980-08-12

1977-12-19 Application filed by Individual filed Critical Individual

1980-08-12 Application granted granted Critical

1980-08-12 Publication of CA1083609A publication Critical patent/CA1083609A/en

Status Expired legal-status Critical Current

Links

UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 77
239000003054 catalyst Substances 0.000 claims abstract description 71
239000010457 zeolite Substances 0.000 claims abstract description 37
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 33
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 29
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 23
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 20
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000010948 rhodium Substances 0.000 claims abstract description 13
229910052741 iridium Inorganic materials 0.000 claims abstract description 12
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052763 palladium Inorganic materials 0.000 claims abstract description 12
229910052703 rhodium Inorganic materials 0.000 claims abstract description 12
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims description 51
230000008569 process Effects 0.000 claims description 46
238000001354 calcination Methods 0.000 claims description 21
229910052751 metal Inorganic materials 0.000 claims description 15
239000002184 metal Substances 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 13
150000001555 benzenes Chemical group 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000002131 composite material Substances 0.000 claims description 4
229910001882 dioxygen Inorganic materials 0.000 claims description 4
150000001491 aromatic compounds Chemical class 0.000 claims 3
238000010544 hydroalkylation process reaction Methods 0.000 abstract description 9
-1 benzene and analogs Chemical class 0.000 abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
239000001301 oxygen Substances 0.000 abstract description 2
229910052760 oxygen Inorganic materials 0.000 abstract description 2
230000000875 corresponding effect Effects 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 21
230000000052 comparative effect Effects 0.000 description 12
239000000843 powder Substances 0.000 description 10
239000000047 product Substances 0.000 description 8
239000000376 reactant Substances 0.000 description 8
239000000243 solution Substances 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
229910052761 rare earth metal Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
150000002910 rare earth metals Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OQXMLPWEDVZNPA-UHFFFAOYSA-N 1,2-dicyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1C1CCCCC1 OQXMLPWEDVZNPA-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000012159 carrier gas Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910021120 PdC12 Inorganic materials 0.000 description 1
229910002666 PdCl2 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
150000003841 chloride salts Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
238000000151 deposition Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
229910052905 tridymite Inorganic materials 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
239000011998 white catalyst Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
- B01J29/12—Noble metals
- B01J29/123—X-type faujasite
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/74—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition with simultaneous hydrogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- C07C2529/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
- C07C2529/12—Noble metals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA293,319A 1976-12-20 1977-12-19 Hydroalkylation of benzene and analogs Expired CA1083609A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US75203876A	1976-12-20	1976-12-20
US752,038		1976-12-20

Publications (1)

Publication Number	Publication Date
CA1083609A true CA1083609A (en)	1980-08-12

Family

ID=25024586

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,319A Expired CA1083609A (en)	1976-12-20	1977-12-19	Hydroalkylation of benzene and analogs

Country Status (14)

Country	Link
JP (1)	JPS53101332A (de)
AT (1)	AT356087B (de)
AU (1)	AU509407B2 (de)
BE (1)	BE862016A (de)
BR (1)	BR7708432A (de)
CA (1)	CA1083609A (de)
DE (1)	DE2756628A1 (de)
DK (1)	DK562377A (de)
ES (1)	ES465774A1 (de)
FR (1)	FR2374282A1 (de)
GB (1)	GB1572550A (de)
LU (1)	LU78719A1 (de)
NL (1)	NL7714147A (de)
SE (1)	SE7714457L (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1986001743A1 (en) *	1984-09-12	1986-03-27	Commonwealth Scientific And Industrial Research Or	Composite catalyst of ruthenium on zeolite and a group vi and/or group viii metal on refractory
JP2649484B2 (ja) *	1994-02-28	1997-09-03	新治鎌田	揚綱機の支持装置
JP5192546B2 (ja) *	2007-09-21	2013-05-08	エクソンモービルケミカルパテンツインコーポレイテッド	シクロヘキシルベンゼンの製造プロセス
CN110479355A (zh) *	2019-09-03	2019-11-22	中触媒新材料股份有限公司	一种用于合成环己基苯的催化剂的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1184022A (en) *	1968-02-27	1970-03-11	British Petroleum Co	Process for the Preparation of Cyclo-Alkyl Aromatics
US3839477A (en) *	1972-12-06	1974-10-01	Texaco Inc	Hydroalkylation process

1977
- 1977-12-14 AU AU31538/77A patent/AU509407B2/en not_active Expired
- 1977-12-16 DK DK562377A patent/DK562377A/da not_active Application Discontinuation
- 1977-12-19 FR FR7738280A patent/FR2374282A1/fr not_active Withdrawn
- 1977-12-19 SE SE7714457A patent/SE7714457L/ not_active Application Discontinuation
- 1977-12-19 LU LU78719A patent/LU78719A1/xx unknown
- 1977-12-19 BE BE183591A patent/BE862016A/xx unknown
- 1977-12-19 DE DE19772756628 patent/DE2756628A1/de not_active Withdrawn
- 1977-12-19 BR BR7708432A patent/BR7708432A/pt unknown
- 1977-12-19 CA CA293,319A patent/CA1083609A/en not_active Expired
- 1977-12-20 NL NL7714147A patent/NL7714147A/xx not_active Application Discontinuation
- 1977-12-20 GB GB52963/77A patent/GB1572550A/en not_active Expired
- 1977-12-20 AT AT913977A patent/AT356087B/de not_active IP Right Cessation
- 1977-12-20 JP JP15348177A patent/JPS53101332A/ja active Pending
1978
- 1978-01-04 ES ES465774A patent/ES465774A1/es not_active Expired

Also Published As

Publication number	Publication date
NL7714147A (nl)	1978-06-22
ATA913977A (de)	1979-09-15
JPS53101332A (en)	1978-09-04
BR7708432A (pt)	1978-08-15
ES465774A1 (es)	1979-01-01
LU78719A1 (fr)	1979-07-20
BE862016A (fr)	1978-04-14
GB1572550A (en)	1980-07-30
FR2374282A1 (fr)	1978-07-13
AU509407B2 (en)	1980-05-08
DK562377A (da)	1978-06-21
SE7714457L (sv)	1978-06-21
AT356087B (de)	1980-04-10
DE2756628A1 (de)	1978-06-22
AU3153877A (en)	1979-06-21

Legal Events

Date	Code	Title	Description
1997-08-12	MKEX	Expiry

Publication	Publication Date	Title
US4219687A (en)	1980-08-26	Hydroalkylation of benzene and analogs
US4766265A (en)	1988-08-23	Catalysts for the conversion of ethane to liquid aromatic hydrocarbons
US6426442B1 (en)	2002-07-30	Catalyst for the conversion of low carbon number aliphatic hydrocarbons to higher carbon number hydrocarbons, process for preparing the catalyst and process using the catalyst
EP0099715B1 (de)	1986-02-26	Katalysatorzusammensetzung und Verfahren zu ihrer Herstellung sowie ihre Verwendung in der Herstellung von Kohlenwasserstoffen aus Synthesegas
IT8922412A1 (it)	1991-05-16	Processo per l'alchilazione di composti aromatici.
EP0452084B1 (de)	1994-06-15	Verfahren für die Umwandlung von Propan und Butan
US4891467A (en)	1990-01-02	Selective synthesis of pseudocumene and durene
US3760019A (en)	1973-09-18	Hydroalkylation catalyst and process
EP0393895B1 (de)	1994-07-20	Silikometallatmolekularsiebe und deren Anwendung als Katalysatoren bei der Oxydierung von Alkanen
US4380683A (en)	1983-04-19	Hydroalkylation of benzene and analogs
EP0040015B1 (de)	1986-06-11	Verfahren zur Herstellung von Olefinen
CA1169840A (en)	1984-06-26	Transition metal carbonyl complexes intercalated with lamellar materials and use of the intercalated complexes in the catalysis of organic reactions
EP0068542B1 (de)	1985-05-08	Verfahren zur Alkylierung von Benzol oder C1 bis C5-substituierten Benzolen
US4218572A (en)	1980-08-19	Process for the production of polyphenyls
EP0234679B1 (de)	1990-04-18	Verfahren zur Umwandlung von Kohlenwasserstoffen mit kristallinen Borsilikatkatalysatoren für die Erholung von Pseudokumeen
US4912280A (en)	1990-03-27	Olefin dimerization method
EP0370054B1 (de)	1992-01-15	Katalysator und selektives dehydrierungsverfahren
US5059724A (en)	1991-10-22	Preparation of methyl isobutyl ketone
GB1572550A (en)	1980-07-30	Hydroalkylation of benzene and analogues
EP0390058B1 (de)	1993-05-26	Katalysatorzusammensetzung, Verfahren zum Kracken von Nichtaromaten und Verfahren zum Isomerisieren von C8-aromatischen Kohlenwasserstoffen
US4665252A (en)	1987-05-12	Preparation of alkylbenzenes
EP0105591B1 (de)	1986-07-16	Verfahren zur katalytischen Umsetzung von Methanol zu leichten Olefinen
GB2151603A (en)	1985-07-24	Modified clay
US4982032A (en)	1991-01-01	Process for converting a wet acetylene-containing stream to aromatics using a zinc-promoted, crystalline, borosilicate molecular sieve catalyst composition
US4115463A (en)	1978-09-19	Production of cycloalkylaromatics