CA1117549A - High temperature vapor phase catalytic dimerization of acrylonitrile - Google Patents

High temperature vapor phase catalytic dimerization of acrylonitrile

Info

Publication number: CA1117549A
Authority: CA; Canada
Prior art keywords: catalyst; metal; acrylonitrile; metalloid; sulfide
Prior art date: 1976-11-26
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

CA000291804A

Other languages

English (en)

French (fr)

Inventor

James L. Callahan

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.)

1976-11-26

Filing date

1977-11-25

Publication date

1982-02-02

1977-11-25 Application filed by Individual filed Critical Individual

1982-02-02 Application granted granted Critical

1982-02-02 Publication of CA1117549A publication Critical patent/CA1117549A/en

Status Expired legal-status Critical Current

Links

NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims abstract description 52
239000012808 vapor phase Substances 0.000 title claims abstract description 11
238000006471 dimerization reaction Methods 0.000 title abstract description 18
230000003197 catalytic effect Effects 0.000 title abstract description 15
239000003054 catalyst Substances 0.000 claims abstract description 69
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 56
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 34
229910052945 inorganic sulfide Inorganic materials 0.000 claims abstract description 12
229910052751 metal Inorganic materials 0.000 claims description 44
239000002184 metal Substances 0.000 claims description 44
238000000034 method Methods 0.000 claims description 41
150000002738 metalloids Chemical class 0.000 claims description 36
229910052752 metalloid Inorganic materials 0.000 claims description 35
230000008569 process Effects 0.000 claims description 35
239000000463 material Substances 0.000 claims description 18
239000002131 composite material Substances 0.000 claims description 15
150000002739 metals Chemical class 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
239000010949 copper Substances 0.000 claims description 5
125000001741 organic sulfur group Chemical group 0.000 claims description 5
-1 paladium Chemical compound 0.000 claims description 5
229910052709 silver Inorganic materials 0.000 claims description 5
239000004332 silver Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052712 strontium Inorganic materials 0.000 claims description 5
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
238000000151 deposition Methods 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
229910052788 barium Inorganic materials 0.000 claims description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
229910052792 caesium Inorganic materials 0.000 claims description 3
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
229910052735 hafnium Inorganic materials 0.000 claims description 3
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
229910052750 molybdenum Inorganic materials 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052761 rare earth metal Inorganic materials 0.000 claims description 3
150000002910 rare earth metals Chemical class 0.000 claims description 3
229910052701 rubidium Inorganic materials 0.000 claims description 3
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 3
229910052706 scandium Inorganic materials 0.000 claims description 3
SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
239000011651 chromium Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
239000011733 molybdenum Substances 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
229910052714 tellurium Inorganic materials 0.000 claims description 2
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
229910052684 Cerium Inorganic materials 0.000 claims 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
230000000447 dimerizing effect Effects 0.000 claims 1
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract description 20
ZQOHAQBXINVHHC-UHFFFAOYSA-N hex-2-enedinitrile Chemical class N#CCCC=CC#N ZQOHAQBXINVHHC-UHFFFAOYSA-N 0.000 abstract description 8
238000006243 chemical reaction Methods 0.000 description 23
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 18
229910000037 hydrogen sulfide Inorganic materials 0.000 description 16
239000002245 particle Substances 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
239000007789 gas Substances 0.000 description 10
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
239000007795 chemical reaction product Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
BSVZXPLUMFUWHW-OWOJBTEDSA-N (e)-hex-3-enedinitrile Chemical compound N#CC\C=C\CC#N BSVZXPLUMFUWHW-OWOJBTEDSA-N 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
239000012159 carrier gas Substances 0.000 description 7
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
238000002474 experimental method Methods 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
239000011593 sulfur Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
COOGPNLGKIHLSK-UHFFFAOYSA-N aluminium sulfide Chemical compound [Al+3].[Al+3].[S-2].[S-2].[S-2] COOGPNLGKIHLSK-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000001354 calcination Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000009467 reduction Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
239000000571 coke Substances 0.000 description 2
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Inorganic materials [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 2
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
JKBPBRLDGFKIIA-UHFFFAOYSA-N 2-propylidenepropanedinitrile Chemical class CCC=C(C#N)C#N JKBPBRLDGFKIIA-UHFFFAOYSA-N 0.000 description 1
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000428352 Amma Species 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
244000118350 Andrographis paniculata Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229920002302 Nylon 6,6 Polymers 0.000 description 1
101150044960 PSPN gene Proteins 0.000 description 1
229910021120 PdC12 Inorganic materials 0.000 description 1
241001237728 Precis Species 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000007792 addition Methods 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
235000019994 cava Nutrition 0.000 description 1
229910052729 chemical element Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000000539 dimer Substances 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
238000010408 sweeping Methods 0.000 description 1
238000007704 wet chemistry method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

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

CA000291804A 1976-11-26 1977-11-25 High temperature vapor phase catalytic dimerization of acrylonitrile Expired CA1117549A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US74502476A	1976-11-26	1976-11-26
US745,024		1976-11-26

Publications (1)

Publication Number	Publication Date
CA1117549A true CA1117549A (en)	1982-02-02

Family

ID=24994924

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000291804A Expired CA1117549A (en)	1976-11-26	1977-11-25	High temperature vapor phase catalytic dimerization of acrylonitrile

Country Status (11)

Country	Link
JP (1)	JPS5368724A (de)
AT (1)	AT360502B (de)
AU (2)	AU517491B2 (de)
BE (1)	BE861222A (de)
CA (1)	CA1117549A (de)
DE (1)	DE2752168A1 (de)
DK (1)	DK527577A (de)
FR (1)	FR2372149A1 (de)
GB (1)	GB1573281A (de)
SE (1)	SE7713392L (de)
ZA (1)	ZA776690B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2542754A1 (fr) *	1983-03-15	1984-09-21	Raffinage Cie Francaise	Procede d'hydrodemetallisation de charges d'hydrocarbures et catalyseur pour la mise en oeuvre de ce procede
FR2780304B1 (fr) *	1998-06-25	2000-07-28	Inst Francais Du Petrole	Catalyseur sulfure et son utilisation
CN114471665B (zh) *	2020-10-27	2023-10-20	中国石油化工股份有限公司	一种制备己二腈的催化剂及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1478618A (en) *	1973-10-01	1977-07-06	Ici Ltd	Dimerisation process and catalyst

1977
- 1977-11-09 ZA ZA00776690A patent/ZA776690B/xx unknown
- 1977-11-23 AU AU30898/77A patent/AU517491B2/en not_active Expired
- 1977-11-23 DE DE19772752168 patent/DE2752168A1/de not_active Withdrawn
- 1977-11-23 AU AU30898/77A patent/AU3089877A/en active Pending
- 1977-11-25 BE BE182944A patent/BE861222A/xx unknown
- 1977-11-25 SE SE7713392A patent/SE7713392L/xx not_active Application Discontinuation
- 1977-11-25 CA CA000291804A patent/CA1117549A/en not_active Expired
- 1977-11-25 GB GB49132/77A patent/GB1573281A/en not_active Expired
- 1977-11-26 JP JP14211677A patent/JPS5368724A/ja active Pending
- 1977-11-28 DK DK527577A patent/DK527577A/da not_active Application Discontinuation
- 1977-11-28 FR FR7735713A patent/FR2372149A1/fr not_active Withdrawn
- 1977-11-28 AT AT851877A patent/AT360502B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK527577A (da)	1978-05-27
AU3089877A (en)	1979-07-05
DE2752168A1 (de)	1978-06-01
AU517491B2 (en)	1981-08-06
ATA851877A (de)	1980-06-15
BE861222A (fr)	1978-03-16
ZA776690B (en)	1978-08-30
JPS5368724A (en)	1978-06-19
AT360502B (de)	1981-01-12
FR2372149A1 (fr)	1978-06-23
SE7713392L (sv)	1978-05-27
GB1573281A (en)	1980-08-20

Legal Events

Date	Code	Title	Description
1999-02-02	MKEX	Expiry

Publication	Publication Date	Title
CA1069873A (en)	1980-01-15	Process for modifying the pore volume distribution of alumina base catalyst supports
CA1310335C (en)	1992-11-17	Gas-phase fluorination process
DE68902509T2 (de)	1993-02-11	Hydrierungsverfahren von chlorfluoroalkenen.
WO1995032150A1 (en)	1995-11-30	Preparation of metal carbide catalyst supported on carbon
CA2128434A1 (en)	1993-09-02	Fluorination of catalyst and process
DE68902022T2 (de)	1993-02-11	Verfahren zur hydrogenierung von 1,1,2-trichloro-1,2,2-trifluoroethan.
CA1117549A (en)	1982-02-02	High temperature vapor phase catalytic dimerization of acrylonitrile
US5523271A (en)	1996-06-04	Catalyst for the simultaneous selective hydrogenation of diolefins and nitriles and method of making same
JP3497202B2 (ja)	2004-02-16	不飽和化合物の選択的水素化のための触媒および方法並びに該触媒の製造法
JP2594463B2 (ja)	1997-03-26	脱水素反応用触媒及びその製法
CA1106393A (en)	1981-08-04	Process for the production of methyl acrylate
JP4110241B2 (ja)	2008-07-02	一酸化炭素転化触媒および該触媒を用いる一酸化炭素転化方法
EP0801641B1 (de)	2003-03-05	Verfahren zur herstellung von aliphatischen alpha,omega-aminonitrilen in der gasphase
JPH0529504B2 (de)	1993-04-30
US3898179A (en)	1975-08-05	Cobalt-and sulfur-containing olefin isomerization process catalyst
DE69414714T2 (de)	1999-07-22	Katalytisches verfahren zum austausch von halogen in halogenkohlenwasserstoffen
US3952069A (en)	1976-04-20	Hydrogenation of aromatics
JPH0529506B2 (de)	1993-04-30
US3350323A (en)	1967-10-31	Catalyst production
US4523016A (en)	1985-06-11	Process for the catalytic dehydrogenation of piperidine
CA1204723A (en)	1986-05-20	Molded iron catalyst and its preparation
EP0886632B1 (de)	2000-05-10	Herstellung von 2,6 - Dimethylnaphthalin
DE2211863C3 (de)	1976-05-26	Verfahren zur Herstellung eines Katalysators und dessen Verwendung
DE2406024B2 (de)	1976-03-18	Katalysator, verfahren zu dessen herstellung und dessen verwendung
EP0191083A1 (de)	1986-08-20	Fischer-tropsch-katalysator