CA1072979A - Preparation of monocarboxylated cyclododecatriene derivatives - Google Patents
Preparation of monocarboxylated cyclododecatriene derivativesInfo
- Publication number
- CA1072979A CA1072979A CA223,780A CA223780A CA1072979A CA 1072979 A CA1072979 A CA 1072979A CA 223780 A CA223780 A CA 223780A CA 1072979 A CA1072979 A CA 1072979A
- Authority
- CA
- Canada
- Prior art keywords
- monoalkyl
- pressurized
- cyclododecatriene
- snc12
- psig
- 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.)
- Expired
Links
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical class C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 13
- 150000005309 metal halides Chemical class 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012298 atmosphere Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- -1 cyclododecadienecarboxylate ester Chemical class 0.000 claims description 29
- 230000021523 carboxylation Effects 0.000 claims description 24
- 238000006473 carboxylation reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229910008066 SnC12 Inorganic materials 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000012442 inert solvent Substances 0.000 claims description 17
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 229910021120 PdC12 Inorganic materials 0.000 claims description 15
- 150000005671 trienes Chemical class 0.000 claims description 15
- JLCPAYASQBAXEO-UHFFFAOYSA-N cyclododeca-1,3-diene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CCCCCCCCC1 JLCPAYASQBAXEO-UHFFFAOYSA-N 0.000 claims description 13
- 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 12
- 150000002148 esters Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- JWIPDQOXAJMVHL-UHFFFAOYSA-N cyclododecanecarboxylic acid Chemical class OC(=O)C1CCCCCCCCCCC1 JWIPDQOXAJMVHL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 229910008046 SnC14 Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 34
- 229910052763 palladium Inorganic materials 0.000 abstract description 17
- 150000007942 carboxylates Chemical class 0.000 abstract description 9
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- 229940105305 carbon monoxide Drugs 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920000299 Nylon 12 Polymers 0.000 description 6
- CXLOYJRGOCQTGN-UHFFFAOYSA-N methyl cyclododeca-1,3-diene-1-carboxylate Chemical compound COC(=O)C1=CC=CCCCCCCCC1 CXLOYJRGOCQTGN-UHFFFAOYSA-N 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229960005419 nitrogen Drugs 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- OKHUNLPPODPLIZ-UHFFFAOYSA-N ethyl cyclododeca-1,3-diene-1-carboxylate Chemical compound CCOC(=O)C1=CC=CCCCCCCCC1 OKHUNLPPODPLIZ-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910002666 PdCl2 Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SXIFNAOBIAIYJO-SXVCMZJPSA-N (1E,3E,7E)-cyclododeca-1,3,7-triene Chemical compound C/1=C\CCCC\C=C\C=C\CC\1 SXIFNAOBIAIYJO-SXVCMZJPSA-N 0.000 description 1
- 101100387782 Mus musculus Dnajb3 gene Proteins 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- MTBVFPAWEZQGHW-UHFFFAOYSA-N ethyl cyclododecanecarboxylate Chemical compound CCOC(=O)C1CCCCCCCCCCC1 MTBVFPAWEZQGHW-UHFFFAOYSA-N 0.000 description 1
- UPPHEOBTADEYHQ-UHFFFAOYSA-N ethyl cyclododecene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCCCCCCCC1 UPPHEOBTADEYHQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 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
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- GNQJGSLILWBFNR-UHFFFAOYSA-N methyl cyclododecanecarboxylate Chemical compound COC(=O)C1CCCCCCCCCCC1 GNQJGSLILWBFNR-UHFFFAOYSA-N 0.000 description 1
- ZSYLKSNNCISMDE-UHFFFAOYSA-N methyl cyclododecene-1-carboxylate Chemical compound COC(=O)C1=CCCCCCCCCCC1 ZSYLKSNNCISMDE-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/462,832 US3932484A (en) | 1974-04-22 | 1974-04-22 | Preparation of monocarboxylated cyclododeca derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072979A true CA1072979A (en) | 1980-03-04 |
Family
ID=23837937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA223,780A Expired CA1072979A (en) | 1974-04-22 | 1975-04-03 | Preparation of monocarboxylated cyclododecatriene derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3932484A (ref) |
| JP (1) | JPS50137958A (ref) |
| BE (1) | BE827701A (ref) |
| CA (1) | CA1072979A (ref) |
| DE (1) | DE2511197A1 (ref) |
| FR (1) | FR2268007A1 (ref) |
| GB (1) | GB1500047A (ref) |
| IT (1) | IT1037453B (ref) |
| NL (1) | NL7503818A (ref) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3906514A1 (de) * | 1989-03-01 | 1990-09-06 | Consortium Elektrochem Ind | Cycloolefinkomplexe des platins, verfahren zu deren herstellung sowie deren verwendung als katalysator |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2675390A (en) * | 1950-05-19 | 1954-04-13 | Edgar F Rosenblatt | Hydrogenation of cyclic-compounds |
| GB1051627A (ref) * | 1961-12-29 | |||
| NL291646A (ref) * | 1962-04-18 | |||
| FR2085113A5 (en) * | 1970-03-25 | 1971-12-17 | Ici Ltd | Palladium/iron complex olefin carboxylation catalyst |
| US3700706A (en) * | 1970-08-17 | 1972-10-24 | Mobil Oil Corp | Selective carbonylation of olefinically unsaturated hydrocarbons using palladium-phosphine catalysts promoted with tin salts |
-
1974
- 1974-04-22 US US05/462,832 patent/US3932484A/en not_active Expired - Lifetime
-
1975
- 1975-02-10 JP JP50016384A patent/JPS50137958A/ja active Pending
- 1975-03-14 GB GB10662/75A patent/GB1500047A/en not_active Expired
- 1975-03-14 DE DE19752511197 patent/DE2511197A1/de active Pending
- 1975-04-01 NL NL7503818A patent/NL7503818A/xx not_active Application Discontinuation
- 1975-04-03 CA CA223,780A patent/CA1072979A/en not_active Expired
- 1975-04-04 FR FR7510560A patent/FR2268007A1/fr not_active Withdrawn
- 1975-04-08 BE BE155205A patent/BE827701A/xx unknown
- 1975-04-18 IT IT22530/75A patent/IT1037453B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7503818A (nl) | 1975-10-24 |
| IT1037453B (it) | 1979-11-10 |
| FR2268007A1 (ref) | 1975-11-14 |
| DE2511197A1 (de) | 1975-11-06 |
| BE827701A (fr) | 1975-10-08 |
| US3932484A (en) | 1976-01-13 |
| JPS50137958A (ref) | 1975-11-01 |
| GB1500047A (en) | 1978-02-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |