DE2217532C3 - Verfahren zur Herstellung von DilithiokohJenwasserstoffen - Google Patents
Verfahren zur Herstellung von DilithiokohJenwasserstoffenInfo
- Publication number
- DE2217532C3 DE2217532C3 DE2217532A DE2217532A DE2217532C3 DE 2217532 C3 DE2217532 C3 DE 2217532C3 DE 2217532 A DE2217532 A DE 2217532A DE 2217532 A DE2217532 A DE 2217532A DE 2217532 C3 DE2217532 C3 DE 2217532C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrocarbons
- compounds
- dilithio
- hydrocarbon
- lithium
- 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
- 229930195733 hydrocarbon Natural products 0.000 title claims description 29
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000010438 heat treatment Methods 0.000 claims description 14
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical class [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000746 allylic group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003999 initiator Substances 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- -1 trans-stilbene Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- VIHUHUGDEZCPDK-GQCTYLIASA-N (e)-5-methylhept-2-ene Chemical compound CCC(C)C\C=C\C VIHUHUGDEZCPDK-GQCTYLIASA-N 0.000 description 1
- WNEYWVBECXCQRT-UHFFFAOYSA-N 5-methylhept-1-ene Chemical compound CCC(C)CCC=C WNEYWVBECXCQRT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000006255 dilithiation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- HDSLTIHESBGENB-UHFFFAOYSA-N lithium;propane Chemical compound [Li]C(C)C HDSLTIHESBGENB-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- VATDYQWILMGLEW-UHFFFAOYSA-N sec-butyllithium Chemical compound [Li]C(C)CC VATDYQWILMGLEW-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BKDLGMUIXWPYGD-UHFFFAOYSA-N tert-butyllithium Chemical compound [Li]C(C)(C)C BKDLGMUIXWPYGD-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F1/02—Lithium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13405971A | 1971-04-14 | 1971-04-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2217532A1 DE2217532A1 (de) | 1973-01-18 |
| DE2217532B2 DE2217532B2 (de) | 1979-06-07 |
| DE2217532C3 true DE2217532C3 (de) | 1980-02-14 |
Family
ID=22461587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2217532A Expired DE2217532C3 (de) | 1971-04-14 | 1972-04-12 | Verfahren zur Herstellung von DilithiokohJenwasserstoffen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3718702A (ref) |
| JP (1) | JPS5824439B1 (ref) |
| AU (1) | AU456970B2 (ref) |
| BR (1) | BR7202208D0 (ref) |
| CA (1) | CA978990A (ref) |
| DE (1) | DE2217532C3 (ref) |
| FR (1) | FR2133678B1 (ref) |
| GB (1) | GB1350875A (ref) |
| ZA (1) | ZA722236B (ref) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4196182A (en) * | 1978-12-07 | 1980-04-01 | Ford Motor Company | Molding articles which can be converted to porous carbon bodies |
| US4686698A (en) * | 1985-04-08 | 1987-08-11 | Datapoint Corporation | Workstation for interfacing with a video conferencing network |
| US5487848A (en) * | 1994-07-25 | 1996-01-30 | Xerox Corporation | Preparation of difunctional initiators for anionic polymerization |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734091A (en) * | 1956-02-07 | Chi chi | ||
| US3085120A (en) * | 1959-08-10 | 1963-04-09 | Ethyl Corp | Preparation of allylic metal compounds |
-
1971
- 1971-04-14 US US00134059A patent/US3718702A/en not_active Expired - Lifetime
-
1972
- 1972-04-04 GB GB1554272A patent/GB1350875A/en not_active Expired
- 1972-04-04 ZA ZA722236A patent/ZA722236B/xx unknown
- 1972-04-05 CA CA138,990A patent/CA978990A/en not_active Expired
- 1972-04-12 DE DE2217532A patent/DE2217532C3/de not_active Expired
- 1972-04-13 AU AU41097/72A patent/AU456970B2/en not_active Expired
- 1972-04-13 FR FR7212953A patent/FR2133678B1/fr not_active Expired
- 1972-04-14 JP JP47036982A patent/JPS5824439B1/ja active Granted
- 1972-04-14 BR BR722208A patent/BR7202208D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA978990A (en) | 1975-12-02 |
| FR2133678B1 (ref) | 1976-07-09 |
| ZA722236B (en) | 1972-12-27 |
| JPS5824439B1 (ref) | 1983-05-20 |
| BR7202208D0 (pt) | 1973-05-24 |
| FR2133678A1 (ref) | 1972-12-01 |
| DE2217532A1 (de) | 1973-01-18 |
| AU4109772A (en) | 1973-10-18 |
| US3718702A (en) | 1973-02-27 |
| GB1350875A (en) | 1974-04-24 |
| AU456970B2 (en) | 1974-12-17 |
| DE2217532B2 (de) | 1979-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |