DE1140569B - Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-Diolefinen - Google Patents
Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-DiolefinenInfo
- Publication number
- DE1140569B DE1140569B DEST15930A DEST015930A DE1140569B DE 1140569 B DE1140569 B DE 1140569B DE ST15930 A DEST15930 A DE ST15930A DE ST015930 A DEST015930 A DE ST015930A DE 1140569 B DE1140569 B DE 1140569B
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- butadiene
- cyclic
- metal
- nickel
- Prior art date
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 16
- 230000003197 catalytic effect Effects 0.000 title claims description 4
- 238000006471 dimerization reaction Methods 0.000 title claims description 3
- 238000005829 trimerization reaction Methods 0.000 title claims description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 107
- 239000003054 catalyst Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 24
- -1 cyclic tertiary amines Chemical class 0.000 claims description 21
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052987 metal hydride Inorganic materials 0.000 claims description 8
- 150000004681 metal hydrides Chemical class 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- MUVALSXEYCDMFJ-UHFFFAOYSA-N 1,2-dimethylcycloocta-1,3-diene Chemical compound CC1=C(C)C=CCCCC1 MUVALSXEYCDMFJ-UHFFFAOYSA-N 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000002879 Lewis base Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001923 cyclic compounds Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical class O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007527 lewis bases Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000005595 acetylacetonate group Chemical group 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 17
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 14
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 13
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 11
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- AFVDZBIIBXWASR-UHFFFAOYSA-N (e)-1,3,5-hexatriene Chemical compound C=CC=CC=C AFVDZBIIBXWASR-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000007306 turnover Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- CWNKMHIETKEBCA-UHFFFAOYSA-N alpha-Ethylaminohexanophenone Chemical compound CCCCC(NCC)C(=O)C1=CC=CC=C1 CWNKMHIETKEBCA-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- 150000005671 trienes Chemical class 0.000 description 3
- 208000005156 Dehydration Diseases 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VWARDJVPFDTYFV-UHFFFAOYSA-N buta-1,3-diene but-1-ene Chemical compound CCC=C.C=CC=C VWARDJVPFDTYFV-UHFFFAOYSA-N 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NQLVCAVEDIGMMW-UHFFFAOYSA-N cyclopenta-1,3-diene;cyclopentane;nickel Chemical compound [Ni].C=1C=C[CH-]C=1.[CH-]1[CH-][CH-][CH-][CH-]1 NQLVCAVEDIGMMW-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000003574 free electron Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 150000002816 nickel compounds Chemical class 0.000 description 2
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- HKFWOZCGNIQGPI-PEJKQWNRSA-N (1Z,3Z,5Z)-1,2,3-trimethylcyclododeca-1,3,5-triene Chemical compound C\C1=C(/C)\C(\C)=C/C=C\CCCCCC1 HKFWOZCGNIQGPI-PEJKQWNRSA-N 0.000 description 1
- XRLIZCVYAYNXIF-PDADCAGHSA-N (1z,3e,5e)-cyclododeca-1,3,5-triene Chemical compound C1CCC\C=C/C=C/C=C/CC1 XRLIZCVYAYNXIF-PDADCAGHSA-N 0.000 description 1
- LQDSIZNFFVRKJA-XORISBCWSA-N (1z,3z)-1-methylcycloocta-1,3-diene Chemical compound C\C1=C\C=C/CCCC1 LQDSIZNFFVRKJA-XORISBCWSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- XXWWKQQAJNKGFY-UHFFFAOYSA-N 2,6-dimethylcycloocta-1,3-diene Chemical compound CC1CCC=C(C)C=CC1 XXWWKQQAJNKGFY-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- HBOBXPNYRYGOCI-UHFFFAOYSA-N 5-methylhepta-1,3,5-triene Chemical compound CC=C(C)C=CC=C HBOBXPNYRYGOCI-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- XRLIZCVYAYNXIF-CRQXNEITSA-N C1CCC\C=C\C=C\C=C\CC1 Chemical compound C1CCC\C=C\C=C\C=C\CC1 XRLIZCVYAYNXIF-CRQXNEITSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XRLIZCVYAYNXIF-UHFFFAOYSA-N cyclododeca-1,3,5-triene Chemical class C1CCCC=CC=CC=CCC1 XRLIZCVYAYNXIF-UHFFFAOYSA-N 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- NIXOIRLDFIPNLJ-UHFFFAOYSA-M magnesium;benzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=[C-]C=C1 NIXOIRLDFIPNLJ-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- UNMGLSGVXHBBPH-BVHINDLDSA-L nickel(2+) (NE)-N-[(3E)-3-oxidoiminobutan-2-ylidene]hydroxylamine Chemical compound [Ni++].C\C(=N/O)\C(\C)=N\[O-].C\C(=N/O)\C(\C)=N\[O-] UNMGLSGVXHBBPH-BVHINDLDSA-L 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- GEQBPMNDDHGGPJ-UHFFFAOYSA-N tri(piperidin-1-yl)phosphane Chemical compound C1CCCCN1P(N1CCCCC1)N1CCCCC1 GEQBPMNDDHGGPJ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- CYABZYIVQJYRDT-UHFFFAOYSA-N trimorpholin-4-ylphosphane Chemical compound C1COCCN1P(N1CCOCC1)N1CCOCC1 CYABZYIVQJYRDT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/21—Alkatrienes; Alkatetraenes; Other alkapolyenes
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
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- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/38—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
- C07C2/40—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes of conjugated dienes
- C07C2/403—Catalytic processes
- C07C2/406—Catalytic processes with hydrides or organic compounds
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
- C07C2/44—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion of conjugated dienes only
- C07C2/46—Catalytic processes
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- C07C2/50—Diels-Alder conversion
- C07C2/52—Catalytic processes
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- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
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- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
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- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL259358D NL259358A (fr) | 1959-12-22 | ||
DEST15930A DE1140569B (de) | 1959-12-22 | 1959-12-22 | Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-Diolefinen |
GB42919/60A GB917103A (en) | 1959-12-22 | 1960-12-13 | Process for the dimerisation or trimerisation of 1,3-diolefines |
SE12365/60A SE302452B (fr) | 1959-12-22 | 1960-12-21 | |
NL60259358A NL153511B (nl) | 1959-12-22 | 1960-12-22 | Werkwijze voor het katalytisch omzetten van 1,3-alkadienen in grotermoleculige koolwaterstoffen. |
DEST23133A DE1283836B (de) | 1959-12-22 | 1961-02-01 | Verfahren zur Herstellung von hauptsaechlich Cyclododekatrien-(1,5,9) enthaltenden Produkten durch Cyclooligomerisation von 1, 3-Diolefinen |
DE19611643071 DE1643071B1 (de) | 1959-12-22 | 1961-06-30 | Verfahren zur Cyclodimerisation von 1,3-Diolefinen |
CH560163A CH498061A (de) | 1959-12-22 | 1963-05-03 | Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-Diolefinen |
US867394A US3641175A (en) | 1959-12-22 | 1969-10-17 | Process for the production of dimers and trimers of conjugated dienes |
US00373525A US3848015A (en) | 1959-12-22 | 1973-06-25 | Process for the production of dimers and trimers of conjugated dienes |
US05/798,199 US4120882A (en) | 1959-12-22 | 1977-05-18 | Metal complexes |
NL7708079A NL7708079A (nl) | 1959-12-22 | 1977-07-20 | Werkwijze voor het katalytisch omzetten van 1,3-alka- dienen in groter-moleculige koolwaterstoffen. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEST15930A DE1140569B (de) | 1959-12-22 | 1959-12-22 | Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-Diolefinen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1140569B true DE1140569B (de) | 1962-12-06 |
Family
ID=7456876
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEST15930A Pending DE1140569B (de) | 1959-12-22 | 1959-12-22 | Verfahren zur katalytischen Di- bzw. Trimerisation von 1,3-Diolefinen |
Country Status (5)
Country | Link |
---|---|
CH (1) | CH498061A (fr) |
DE (1) | DE1140569B (fr) |
GB (1) | GB917103A (fr) |
NL (3) | NL153511B (fr) |
SE (1) | SE302452B (fr) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3277099A (en) * | 1962-07-28 | 1966-10-04 | Basf Ag | Production of open-chain oligomers of 1, 3-dienes |
US3284520A (en) * | 1963-06-24 | 1966-11-08 | Phillips Petroleum Co | Oligomerization |
US3352931A (en) * | 1965-08-16 | 1967-11-14 | Phillips Petroleum Co | Catalytic oligomerization of butadiene |
US3359337A (en) * | 1965-06-11 | 1967-12-19 | Union Carbide Corp | Diene oligomerization |
US3439054A (en) * | 1966-12-08 | 1969-04-15 | Exxon Research Engineering Co | Metal carbonyl catalyst and hydrogenation process therefor |
US3480685A (en) * | 1963-03-20 | 1969-11-25 | Nat Distillers Chem Corp | Octatriene process |
US3538172A (en) * | 1968-10-19 | 1970-11-03 | Huels Chemische Werke Ag | Continuous process for the production of cyclooctadiene |
DE1643063B1 (de) * | 1967-04-08 | 1972-03-16 | Studiengesellschaft Kohle Mbh | Verfahren zur Cyclodimerisation von 1,3-Diolefinen mittels Nickel enthaltender Katalysatoren |
DE2461524A1 (de) * | 1973-12-27 | 1975-08-21 | Takasago Perfumery Co Ltd | 1,2,6-trimethyltricyclo eckige klammer auf 5,3,2,0 hoch 2,7 eckige klammer zu dodeca-5-en und verfahren zu seiner herstellung |
DE2638430A1 (de) | 1976-08-26 | 1978-03-02 | Studiengesellschaft Kohle Mbh | Verfahren zur steuerung der katalytischen mischoligomerisation von 1,3-dienen mit schiffschen basen |
WO2006051011A1 (fr) * | 2004-11-11 | 2006-05-18 | Degussa Gmbh | Procede de production de trimethylcyclododecatriene |
DE4395195B4 (de) * | 1992-10-16 | 2007-01-04 | Mitsubishi Chemical Corp. | Verfahren zur Dimerisierung von Butenen, dimere Zusammensetzung von Butenen und Verfahren zur Herstellung von Alkoholen mittels dieser |
EP1860086A1 (fr) * | 2006-05-10 | 2007-11-28 | Evonik Degussa GmbH | Procédé destiné à la fabrication de cyclododecatriènes |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3249641A (en) * | 1962-06-14 | 1966-05-03 | Columbian Carbon | Catalyst and cycloolefin production |
US3250817A (en) * | 1963-06-17 | 1966-05-10 | Chevron Res | 1, 5-cyclooctadiene |
US3392207A (en) * | 1964-03-16 | 1968-07-09 | Union Carbide Corp | Process for making octatriene and polyunsaturated polymers |
US3414629A (en) * | 1965-05-13 | 1968-12-03 | Eastman Kodak Co | Cyclooligomerization |
US4189403A (en) | 1977-01-19 | 1980-02-19 | Shell Oil Company | Catalyst for cyclodimerization of isoprene |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1086226B (de) * | 1959-03-10 | 1960-08-04 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Cyclododecatrien-(1, 5, 9) |
-
0
- NL NL259358D patent/NL259358A/xx unknown
-
1959
- 1959-12-22 DE DEST15930A patent/DE1140569B/de active Pending
-
1960
- 1960-12-13 GB GB42919/60A patent/GB917103A/en not_active Expired
- 1960-12-21 SE SE12365/60A patent/SE302452B/xx unknown
- 1960-12-22 NL NL60259358A patent/NL153511B/xx not_active IP Right Cessation
-
1963
- 1963-05-03 CH CH560163A patent/CH498061A/de not_active IP Right Cessation
-
1977
- 1977-07-20 NL NL7708079A patent/NL7708079A/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1086226B (de) * | 1959-03-10 | 1960-08-04 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Cyclododecatrien-(1, 5, 9) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3277099A (en) * | 1962-07-28 | 1966-10-04 | Basf Ag | Production of open-chain oligomers of 1, 3-dienes |
US3480685A (en) * | 1963-03-20 | 1969-11-25 | Nat Distillers Chem Corp | Octatriene process |
US3284520A (en) * | 1963-06-24 | 1966-11-08 | Phillips Petroleum Co | Oligomerization |
US3359337A (en) * | 1965-06-11 | 1967-12-19 | Union Carbide Corp | Diene oligomerization |
US3352931A (en) * | 1965-08-16 | 1967-11-14 | Phillips Petroleum Co | Catalytic oligomerization of butadiene |
US3439054A (en) * | 1966-12-08 | 1969-04-15 | Exxon Research Engineering Co | Metal carbonyl catalyst and hydrogenation process therefor |
DE1643063B1 (de) * | 1967-04-08 | 1972-03-16 | Studiengesellschaft Kohle Mbh | Verfahren zur Cyclodimerisation von 1,3-Diolefinen mittels Nickel enthaltender Katalysatoren |
US3538172A (en) * | 1968-10-19 | 1970-11-03 | Huels Chemische Werke Ag | Continuous process for the production of cyclooctadiene |
DE2461524A1 (de) * | 1973-12-27 | 1975-08-21 | Takasago Perfumery Co Ltd | 1,2,6-trimethyltricyclo eckige klammer auf 5,3,2,0 hoch 2,7 eckige klammer zu dodeca-5-en und verfahren zu seiner herstellung |
DE2638430A1 (de) | 1976-08-26 | 1978-03-02 | Studiengesellschaft Kohle Mbh | Verfahren zur steuerung der katalytischen mischoligomerisation von 1,3-dienen mit schiffschen basen |
US4163024A (en) | 1976-08-26 | 1979-07-31 | Studiengesellschaft Kohle Mbh. | Process for controlling the catalytic co-oligomerization of 1,3-dienes with Schiff's bases |
DE4395195B4 (de) * | 1992-10-16 | 2007-01-04 | Mitsubishi Chemical Corp. | Verfahren zur Dimerisierung von Butenen, dimere Zusammensetzung von Butenen und Verfahren zur Herstellung von Alkoholen mittels dieser |
WO2006051011A1 (fr) * | 2004-11-11 | 2006-05-18 | Degussa Gmbh | Procede de production de trimethylcyclododecatriene |
US8759280B2 (en) | 2004-11-11 | 2014-06-24 | Evonik Degussa Gmbh | Method for producing trimethylcyclododecatriene |
EP1860086A1 (fr) * | 2006-05-10 | 2007-11-28 | Evonik Degussa GmbH | Procédé destiné à la fabrication de cyclododecatriènes |
US8168841B2 (en) | 2006-05-10 | 2012-05-01 | Evonik Degussa Gmbh | Process for preparing cyclododecatriene |
Also Published As
Publication number | Publication date |
---|---|
NL259358A (fr) | |
GB917103A (en) | 1963-01-30 |
SE302452B (fr) | 1968-07-22 |
NL7708079A (nl) | 1977-10-31 |
NL153511B (nl) | 1977-06-15 |
CH498061A (de) | 1970-10-31 |
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