GB1011835A - Improved base-solvent or alkali metal-solvent catalyst system - Google Patents
Improved base-solvent or alkali metal-solvent catalyst systemInfo
- Publication number
- GB1011835A GB1011835A GB17649/62A GB1764962A GB1011835A GB 1011835 A GB1011835 A GB 1011835A GB 17649/62 A GB17649/62 A GB 17649/62A GB 1764962 A GB1764962 A GB 1764962A GB 1011835 A GB1011835 A GB 1011835A
- Authority
- GB
- United Kingdom
- Prior art keywords
- olefins
- phosphoramide
- alkali metal
- dimethyl
- radical
- 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
- 239000003054 catalyst Substances 0.000 title abstract 4
- 239000002904 solvent Substances 0.000 title 2
- 239000003513 alkali Substances 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 15
- 238000006243 chemical reaction Methods 0.000 abstract 14
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 11
- 239000007788 liquid Substances 0.000 abstract 11
- 150000001336 alkenes Chemical class 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 229910052783 alkali metal Inorganic materials 0.000 abstract 9
- 150000001340 alkali metals Chemical class 0.000 abstract 9
- 150000003254 radicals Chemical class 0.000 abstract 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 8
- 150000004820 halides Chemical class 0.000 abstract 7
- -1 tetramethyl sulphonamide Chemical compound 0.000 abstract 6
- 238000007792 addition Methods 0.000 abstract 5
- 229910052751 metal Inorganic materials 0.000 abstract 5
- 239000002184 metal Substances 0.000 abstract 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 5
- 230000003647 oxidation Effects 0.000 abstract 5
- 238000007254 oxidation reaction Methods 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 4
- 239000005977 Ethylene Substances 0.000 abstract 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 4
- 230000015572 biosynthetic process Effects 0.000 abstract 4
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 abstract 4
- 150000001993 dienes Chemical class 0.000 abstract 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 abstract 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 abstract 3
- ZQGWBPQBZHMUFG-UHFFFAOYSA-N 1,1-dimethylthiourea Chemical compound CN(C)C(N)=S ZQGWBPQBZHMUFG-UHFFFAOYSA-N 0.000 abstract 3
- WFJXYIUAMJAURQ-UHFFFAOYSA-N 2-propan-2-ylsulfinylpropane Chemical compound CC(C)S(=O)C(C)C WFJXYIUAMJAURQ-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 3
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 abstract 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 3
- 150000004703 alkoxides Chemical class 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- LDMSZRWIHYAPSV-UHFFFAOYSA-N bis(methylsulfanyl)phosphorylsulfanylmethane Chemical compound CSP(=O)(SC)SC LDMSZRWIHYAPSV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 3
- 150000004678 hydrides Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- WFIPYARNKIWELZ-UHFFFAOYSA-N n-[bis(methylamino)phosphoryl]methanamine Chemical compound CNP(=O)(NC)NC WFIPYARNKIWELZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 3
- 229940124530 sulfonamide Drugs 0.000 abstract 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 abstract 2
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 2
- 229940073608 benzyl chloride Drugs 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- 229940113088 dimethylacetamide Drugs 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 150000004795 grignard reagents Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 2
- WPHGSKGZRAQSGP-UHFFFAOYSA-N norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- KBGJIKKXNIQHQH-UHFFFAOYSA-N potassium;methanidylbenzene Chemical compound [K+].[CH2-]C1=CC=CC=C1 KBGJIKKXNIQHQH-UHFFFAOYSA-N 0.000 abstract 2
- 150000004763 sulfides Chemical class 0.000 abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006845 Michael addition reaction Methods 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001345 alkine derivatives Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 230000006315 carbonylation Effects 0.000 abstract 1
- 238000005810 carbonylation reaction Methods 0.000 abstract 1
- 230000021523 carboxylation Effects 0.000 abstract 1
- 238000006473 carboxylation reaction Methods 0.000 abstract 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006197 hydroboration reaction Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229960003424 phenylacetic acid Drugs 0.000 abstract 1
- 239000003279 phenylacetic acid Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
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- C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
- B01J31/0258—Phosphoric acid mono-, di- or triesters ((RO)(R'O)2P=O), i.e. R= C, R'= C, H
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- 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
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- 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
- B01J2231/325—Cyclopropanations
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
- C07C2523/04—Alkali metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US111173A US3270084A (en) | 1961-05-19 | 1961-05-19 | Method of isomerizing olefins |
| US111172A US3213155A (en) | 1961-05-19 | 1961-05-19 | Monoolefin isomerization process |
| US115302A US3217050A (en) | 1961-06-07 | 1961-06-07 | Alkali metal catalyzed conversion of organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1011835A true GB1011835A (en) | 1965-12-01 |
Family
ID=27380954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17649/62A Expired GB1011835A (en) | 1961-05-19 | 1962-05-08 | Improved base-solvent or alkali metal-solvent catalyst system |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH419061A (enrdf_load_stackoverflow) |
| DE (1) | DE1262274B (enrdf_load_stackoverflow) |
| GB (1) | GB1011835A (enrdf_load_stackoverflow) |
| NL (1) | NL278556A (enrdf_load_stackoverflow) |
| SE (1) | SE317674B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008727A1 (de) * | 1978-08-24 | 1980-03-19 | Hoechst Aktiengesellschaft | Verfahren zur Hydrierung organischer Verbindungen |
| US4556754A (en) * | 1982-02-19 | 1985-12-03 | Chemische Werke Huels Aktiengesellschaft | Process for the isomerization of isolated double bonds to conjugated double bonds in low-molecular weight homo- and/or copolymers of 1,3-dienes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105675557B (zh) * | 2016-01-07 | 2019-01-25 | 济南大学 | 基于苯炔荧光试剂检测硫脲含量的新方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB785760A (en) * | 1953-09-23 | 1957-11-06 | Union Carbide Corp | Process for the production of cyclopentadiene compounds of transition elements |
| NL99130C (enrdf_load_stackoverflow) * | 1956-12-10 | |||
| BE598068A (enrdf_load_stackoverflow) * | 1957-08-12 | |||
| AT219056B (de) * | 1957-12-03 | 1962-01-10 | Consortium Elektrochem Ind | Verfahren zur Polymerisation von ungesättigten Verbindungen |
| FR1225915A (fr) * | 1958-05-28 | 1960-07-06 | Purdue Research Foundation | Procédé pour l'isomérisation des oléfines internes en oléfines terminales |
| GB870949A (en) * | 1958-12-17 | 1961-06-21 | Ici Ltd | Process of manufacture of ferrocene derivatives |
-
0
- NL NL278556D patent/NL278556A/xx unknown
-
1962
- 1962-05-08 GB GB17649/62A patent/GB1011835A/en not_active Expired
- 1962-05-16 DE DEE22890A patent/DE1262274B/de active Pending
- 1962-05-17 SE SE5553/62A patent/SE317674B/xx unknown
- 1962-05-18 CH CH602562A patent/CH419061A/de unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008727A1 (de) * | 1978-08-24 | 1980-03-19 | Hoechst Aktiengesellschaft | Verfahren zur Hydrierung organischer Verbindungen |
| US4556754A (en) * | 1982-02-19 | 1985-12-03 | Chemische Werke Huels Aktiengesellschaft | Process for the isomerization of isolated double bonds to conjugated double bonds in low-molecular weight homo- and/or copolymers of 1,3-dienes |
Also Published As
| Publication number | Publication date |
|---|---|
| SE317674B (enrdf_load_stackoverflow) | 1969-11-24 |
| DE1262274B (de) | 1968-03-07 |
| NL278556A (enrdf_load_stackoverflow) | |
| CH419061A (de) | 1966-08-31 |
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