NO121894B - - Google Patents
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- Publication number
- NO121894B NO121894B NO4111/69A NO411169A NO121894B NO 121894 B NO121894 B NO 121894B NO 4111/69 A NO4111/69 A NO 4111/69A NO 411169 A NO411169 A NO 411169A NO 121894 B NO121894 B NO 121894B
- Authority
- NO
- Norway
- Prior art keywords
- oha
- ohp
- tetralin
- reaction
- tpb
- Prior art date
Links
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 225
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 239000007788 liquid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- YSZLFGZFQTTZIQ-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octahydrophenanthrene Chemical compound C1CCCC2=C1C=CC1=C2CCCC1 YSZLFGZFQTTZIQ-UHFFFAOYSA-N 0.000 claims description 7
- LFAYMJXHGYUQNV-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octahydroanthracene Chemical compound C1CCCC2=C1C=C1CCCCC1=C2 LFAYMJXHGYUQNV-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 description 28
- 230000035484 reaction time Effects 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002002 slurry Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- PJDWNSYGMXODTB-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6-octahydrophenanthrene Chemical compound C1=CCCC2C(CCCC3)C3=CC=C21 PJDWNSYGMXODTB-UHFFFAOYSA-N 0.000 description 1
- VTIBBOHXBURHMD-UHFFFAOYSA-N 1,2,3,4,4a,5,10,10a-octahydroanthracene Chemical compound C1=CCC2CC(CCCC3)C3=CC2=C1 VTIBBOHXBURHMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000640099 Moloha Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- -1 methanol Chemical compound 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
- C07C13/58—Completely or partially hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/553—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with an indacene or hydrogenated indacene ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
-
- 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
- C07C2/04—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/271—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with inorganic acids; with salts or anhydrides of acids
- C07C5/2718—Acids of halogen; Salts thereof; complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/10—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond in hydrocarbons containing no six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/123—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of only one hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/10—Chlorides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1206—Hydrogen fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34768564A | 1964-02-27 | 1964-02-27 | |
| US38869364A | 1964-08-10 | 1964-08-10 | |
| US534428A US3336407A (en) | 1964-02-27 | 1966-03-15 | Catalytic conversion of 1, 2, 3, 4-tetrahydronaphthalene, indan, and other materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121894B true NO121894B (US07922777-20110412-C00004.png) | 1971-04-26 |
Family
ID=27407791
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO156854A NO121779B (US07922777-20110412-C00004.png) | 1964-02-27 | 1965-02-19 | |
| NO4111/69A NO121894B (US07922777-20110412-C00004.png) | 1964-02-27 | 1969-10-15 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO156854A NO121779B (US07922777-20110412-C00004.png) | 1964-02-27 | 1965-02-19 |
Country Status (11)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1116052A (en) * | 1966-04-21 | 1968-06-06 | British Iron Steel Research | Improvements in and relating to the analysis of molten materials |
| US3412166A (en) * | 1966-09-20 | 1968-11-19 | Sun Oil Co | Conversion of hydrocarbons containing the nucleus of 1, 2, 3, 4-tetrahydronaphthalene to hydrocarbons containing the nucleus of indene |
| US3453342A (en) * | 1967-12-14 | 1969-07-01 | Sun Oil Co | Method of making 9-methyloctahydroanthracene and 9-methyloctahydro phenanthrene |
| US3534114A (en) * | 1968-03-26 | 1970-10-13 | Sun Oil Co | Combination of gd alumino-silicate catalyst and hydrogenation catalyst |
| US4458047A (en) * | 1982-06-07 | 1984-07-03 | Sun Tech, Inc. | Process for making naphthalene hydrodimer mixtures, product mixtures made thereby and their use as a plasticizer |
| JPS601354B2 (ja) * | 1982-10-14 | 1985-01-14 | 出光興産株式会社 | トラクシヨンドライブ用流体 |
| US5087785A (en) * | 1990-12-03 | 1992-02-11 | Union Camp Corporation | Processes for preparing alkylated indanes and tetrahydronaphthalenes |
| CA2109541A1 (en) * | 1992-12-04 | 1994-06-05 | Thomas J. Ford | Aromatic oil and process for manufacture |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE503246A (US07922777-20110412-C00004.png) * | 1950-05-15 | |||
| US2884469A (en) * | 1956-03-26 | 1959-04-28 | Standard Oil Co | Upgrading fused benzenoid ring hydrocarbons |
| US3197518A (en) * | 1962-04-04 | 1965-07-27 | Ashland Oil Inc | Interconversion of hydrocarbon ring compounds |
| US3244758A (en) * | 1963-03-20 | 1966-04-05 | Sun Oil Co | Reaction of aromatic hydrocarbons with diolefins |
-
0
- BE BE660353D patent/BE660353A/xx unknown
-
1965
- 1965-02-02 GB GB4517/63A patent/GB1024500A/en not_active Expired
- 1965-02-16 FI FI0370/65A patent/FI42827B/fi active
- 1965-02-19 NO NO156854A patent/NO121779B/no unknown
- 1965-02-23 SE SE02338/65A patent/SE350250B/xx unknown
- 1965-02-25 CH CH264665A patent/CH477381A/de not_active IP Right Cessation
- 1965-02-25 CH CH949069A patent/CH499476A/de not_active IP Right Cessation
- 1965-02-26 NL NL656502502A patent/NL144256B/xx unknown
- 1965-02-26 DE DE19651793813 patent/DE1793813A1/de active Pending
- 1965-02-27 DK DK103665AA patent/DK120590B/da unknown
-
1966
- 1966-03-15 US US534428A patent/US3336407A/en not_active Expired - Lifetime
- 1966-09-12 DK DK469866AA patent/DK112445B/da unknown
-
1967
- 1967-02-21 NL NL6702589A patent/NL6702589A/xx unknown
- 1967-03-08 CH CH340867A patent/CH519449A/de not_active IP Right Cessation
- 1967-03-15 GB GB02144/67A patent/GB1178735A/en not_active Expired
- 1967-03-15 DE DE19671618864 patent/DE1618864A1/de active Pending
- 1967-03-15 FR FR98842A patent/FR92718E/fr not_active Expired
- 1967-03-15 BE BE695546D patent/BE695546A/xx unknown
-
1969
- 1969-09-17 FI FI2659/69A patent/FI42829B/fi active
- 1969-10-15 NO NO4111/69A patent/NO121894B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL144256B (nl) | 1974-12-16 |
| BE695546A (US07922777-20110412-C00004.png) | 1967-09-15 |
| CH499476A (de) | 1970-11-30 |
| US3336407A (en) | 1967-08-15 |
| FI42827B (US07922777-20110412-C00004.png) | 1970-08-03 |
| DK112445B (da) | 1968-12-16 |
| DE1493030A1 (de) | 1969-01-30 |
| FI42829B (US07922777-20110412-C00004.png) | 1970-08-03 |
| DK120590B (da) | 1971-06-21 |
| NL6702589A (US07922777-20110412-C00004.png) | 1967-09-18 |
| GB1178735A (en) | 1970-01-21 |
| FR92718E (fr) | 1968-11-12 |
| DE1618864A1 (de) | 1971-08-12 |
| NO121779B (US07922777-20110412-C00004.png) | 1971-04-13 |
| DE1793813A1 (de) | 1976-07-01 |
| DE1493030B2 (de) | 1975-07-24 |
| SE350250B (US07922777-20110412-C00004.png) | 1972-10-23 |
| NL6502502A (US07922777-20110412-C00004.png) | 1965-08-30 |
| GB1024500A (en) | 1966-03-30 |
| CH477381A (de) | 1969-08-31 |
| CH519449A (de) | 1972-02-29 |
| BE660353A (US07922777-20110412-C00004.png) |
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