GB889993A - Cyclization of substituted acetylenes to produce aromatic compounds - Google Patents
Cyclization of substituted acetylenes to produce aromatic compoundsInfo
- Publication number
- GB889993A GB889993A GB1781858A GB1781858A GB889993A GB 889993 A GB889993 A GB 889993A GB 1781858 A GB1781858 A GB 1781858A GB 1781858 A GB1781858 A GB 1781858A GB 889993 A GB889993 A GB 889993A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dioxane
- benzene
- cyclization
- tetraphenylbenzene
- mixture
- 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
- 150000001491 aromatic compounds Chemical class 0.000 title abstract 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 title abstract 2
- 238000007363 ring formation reaction Methods 0.000 title abstract 2
- OIQOECYRLBNNBQ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical compound [Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] OIQOECYRLBNNBQ-UHFFFAOYSA-N 0.000 abstract 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 4
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 abstract 3
- QBHWPVJPWQGYDS-UHFFFAOYSA-N hexaphenylbenzene Chemical compound C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(C=1C=CC=CC=1)=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 QBHWPVJPWQGYDS-UHFFFAOYSA-N 0.000 abstract 3
- 239000000411 inducer Substances 0.000 abstract 3
- JKXRLGXEIIOXBU-UHFFFAOYSA-N 1,2,3,4,5,6-hexakis(4-chlorophenyl)benzene Chemical compound C1=CC(Cl)=CC=C1C(C(=C(C=1C=CC(Cl)=CC=1)C(C=1C=CC(Cl)=CC=1)=C1C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 JKXRLGXEIIOXBU-UHFFFAOYSA-N 0.000 abstract 2
- SKTCWUHHHPSBCJ-UHFFFAOYSA-N 1,2,3,5-tetraphenylbenzene Chemical compound C1=CC=CC=C1C(C=C1C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 SKTCWUHHHPSBCJ-UHFFFAOYSA-N 0.000 abstract 2
- KEFTXZXMQLWFND-UHFFFAOYSA-N 1,2-diethyl-3,4,5,6-tetraphenylbenzene Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(CC)=C(CC)C=1C1=CC=CC=C1 KEFTXZXMQLWFND-UHFFFAOYSA-N 0.000 abstract 2
- DQQNMIPXXNPGCV-UHFFFAOYSA-N 3-hexyne Chemical group CCC#CCC DQQNMIPXXNPGCV-UHFFFAOYSA-N 0.000 abstract 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- JKLYQGQCMNPZSJ-UHFFFAOYSA-N dimethyl 3,4,5,6-tetraphenylbenzene-1,2-dicarboxylate Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C(=O)OC)=C(C(=O)OC)C=1C1=CC=CC=C1 JKLYQGQCMNPZSJ-UHFFFAOYSA-N 0.000 abstract 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- BRKIUDNMOJKLLG-UHFFFAOYSA-N tetramethyl 5,6-diphenylbenzene-1,2,3,4-tetracarboxylate Chemical compound C=1C=CC=CC=1C1=C(C(=O)OC)C(C(=O)OC)=C(C(=O)OC)C(C(=O)OC)=C1C1=CC=CC=C1 BRKIUDNMOJKLLG-UHFFFAOYSA-N 0.000 abstract 2
- HQXHFQCVNCQKDZ-UHFFFAOYSA-N trimethyl 3,5,6-triphenylbenzene-1,2,4-tricarboxylate Chemical compound C=1C=CC=CC=1C=1C(C(=O)OC)=C(C=2C=CC=CC=2)C(C(=O)OC)=C(C(=O)OC)C=1C1=CC=CC=C1 HQXHFQCVNCQKDZ-UHFFFAOYSA-N 0.000 abstract 2
- LXSMILGNHYBUCG-UHFFFAOYSA-N 1,2,3,4,5,6-hexaethylbenzene Chemical compound CCC1=C(CC)C(CC)=C(CC)C(CC)=C1CC LXSMILGNHYBUCG-UHFFFAOYSA-N 0.000 abstract 1
- JULFJTZPJNNMQK-UHFFFAOYSA-N 1,2,3,4,5-pentakis-phenylbenzene Chemical compound C1=CC=CC=C1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JULFJTZPJNNMQK-UHFFFAOYSA-N 0.000 abstract 1
- OXDYLTLXDMUGJC-UHFFFAOYSA-N 1,2,3,4-tetraethyl-5,6-diphenylbenzene Chemical compound C(C)C1=C(C(=C(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC)CC)CC OXDYLTLXDMUGJC-UHFFFAOYSA-N 0.000 abstract 1
- QTRGHMZEHIPWHY-UHFFFAOYSA-N 1,2,3-trimethyl-4,5,6-triphenylbenzene Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C)C(C)=C(C)C=1C1=CC=CC=C1 QTRGHMZEHIPWHY-UHFFFAOYSA-N 0.000 abstract 1
- JHWLVAFSWDRHIV-UHFFFAOYSA-N 1,2,4-trimethyl-3,5,6-triphenylbenzene Chemical group C=1C=CC=CC=1C=1C(C)=C(C=2C=CC=CC=2)C(C)=C(C)C=1C1=CC=CC=C1 JHWLVAFSWDRHIV-UHFFFAOYSA-N 0.000 abstract 1
- XXCVBOQRPQKVKY-UHFFFAOYSA-N 1,2,4-triphenylbenzene Chemical compound C1=CC=CC=C1C(C=C1C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 XXCVBOQRPQKVKY-UHFFFAOYSA-N 0.000 abstract 1
- STBWOSJBYDETAQ-UHFFFAOYSA-N 1,2,4-tris(4-bromophenyl)benzene Chemical compound C1=CC(Br)=CC=C1C(C=C1C=2C=CC(Br)=CC=2)=CC=C1C1=CC=C(Br)C=C1 STBWOSJBYDETAQ-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 1
- -1 platinum metals Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- GHUURDQYRGVEHX-UHFFFAOYSA-N prop-1-ynylbenzene Chemical group CC#CC1=CC=CC=C1 GHUURDQYRGVEHX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 abstract 1
- 230000008022 sublimation Effects 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/14—Polycyclic non-condensed hydrocarbons all phenyl groups being directly linked
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
- C07C17/281—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons of only one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—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
- C07C2/48—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 only hydrocarbons containing a carbon-to-carbon triple bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/20—Carbonyls
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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE567744D BE567744A (enrdf_load_stackoverflow) | 1957-05-16 | ||
| GB1781858A GB889993A (en) | 1957-05-16 | 1957-05-16 | Cyclization of substituted acetylenes to produce aromatic compounds |
| FR1206787D FR1206787A (fr) | 1957-05-16 | 1958-05-16 | Procédé de préparation de composés benzéniques substitués et produits ainsi obtenus |
| DEE15878A DE1142867B (de) | 1957-05-16 | 1958-05-16 | Verfahren zur Herstellung von Benzolderivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1781858A GB889993A (en) | 1957-05-16 | 1957-05-16 | Cyclization of substituted acetylenes to produce aromatic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB889993A true GB889993A (en) | 1962-02-21 |
Family
ID=10101760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1781858A Expired GB889993A (en) | 1957-05-16 | 1957-05-16 | Cyclization of substituted acetylenes to produce aromatic compounds |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE567744A (enrdf_load_stackoverflow) |
| DE (1) | DE1142867B (enrdf_load_stackoverflow) |
| FR (1) | FR1206787A (enrdf_load_stackoverflow) |
| GB (1) | GB889993A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2329245C2 (ru) * | 2006-05-10 | 2008-07-20 | ГОУ ВПО Иркутский государственный университет | Способ получения 1,2,4-трифенилбензола |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1246699B (de) * | 1960-05-17 | 1967-08-10 | Ciba Geigy | Verfahren zur Herstellung von Benzolkohlenwasserstoffen durch Cyclisierung von Acetylenkohlenwasserstoffen mittels Halogenide und/oder Oxyhalogenide des Tantals und/oderNiobs enthaltender Katalysatoren |
| DE1234700B (de) * | 1960-10-28 | 1967-02-23 | Ciba Geigy | Verfahren zur Herstellung von Benzolkohlenwasserstoffen durch Cyclisierung von Acctylenkohlenwasserstoffen mit Wolframhalogenide enthaltenden Katalysatoren |
| DE1280869C2 (de) * | 1963-05-21 | 1969-06-26 | Phillips Petroleum Co | Verfahren zur Disproportionierung, Cyclisierung, Addition oder Polymerisation acyclischer, einfach ungesaettigter Olefinkohlenwasserstoffe |
| US5659069A (en) * | 1996-03-20 | 1997-08-19 | Nexstar Pharmaceuticals, Inc. | Method for the cyclotrimerization of alkynes in aqueous solutions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE859464C (de) * | 1940-12-31 | 1952-12-15 | Basf Ag | Verfahren zur Herstellung von cyclischen Polyolefinen |
-
0
- BE BE567744D patent/BE567744A/xx unknown
-
1957
- 1957-05-16 GB GB1781858A patent/GB889993A/en not_active Expired
-
1958
- 1958-05-16 DE DEE15878A patent/DE1142867B/de active Pending
- 1958-05-16 FR FR1206787D patent/FR1206787A/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2329245C2 (ru) * | 2006-05-10 | 2008-07-20 | ГОУ ВПО Иркутский государственный университет | Способ получения 1,2,4-трифенилбензола |
Also Published As
| Publication number | Publication date |
|---|---|
| BE567744A (enrdf_load_stackoverflow) | |
| FR1206787A (fr) | 1960-02-11 |
| DE1142867B (de) | 1963-01-31 |
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