GB923350A - Alkali metal addition compounds of alpha-methyl styrene and method of making - Google Patents
Alkali metal addition compounds of alpha-methyl styrene and method of makingInfo
- Publication number
- GB923350A GB923350A GB1111761A GB1111761A GB923350A GB 923350 A GB923350 A GB 923350A GB 1111761 A GB1111761 A GB 1111761A GB 1111761 A GB1111761 A GB 1111761A GB 923350 A GB923350 A GB 923350A
- Authority
- GB
- United Kingdom
- Prior art keywords
- styrene
- alpha
- potassium
- methyl styrene
- sodium
- 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
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 title abstract 5
- 229910052783 alkali metal Inorganic materials 0.000 title 1
- 150000001340 alkali metals Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000011591 potassium Substances 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- -1 methylethyl Chemical group 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 2
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- 229910000799 K alloy Inorganic materials 0.000 abstract 2
- 229910000528 Na alloy Inorganic materials 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 abstract 2
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 229910001868 water Inorganic materials 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000003570 air Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229910052734 helium Inorganic materials 0.000 abstract 1
- 239000001307 helium Substances 0.000 abstract 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/042—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a polyfunctional initiator
-
- 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
-
- 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
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
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)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Dialkali metal adducts of trito hexa-alpha methyl styrene are prepared by adding sodium, potassium or mixtures and/or alloys of sodium and potassium to an ether solution of alphamethyl styrene in an inert atmosphere, the addition being carried out at a temperature above the ceiling temperature for high polymer formation as defined in the Specification (see Group IV(b)). The product may be reacted with water to give the polymerized hydrocarbon. The ether solution of the adducts may be used as a catalyst in the polymerization of butadiene, isoprene, dimethylbutadiene, styrene, vinyltoluene, isopropylstyrene, tert. butyl styrene or alphamethyl styrene.ALSO:Sodium, potassium or mixtures and/or alloys of sodium and potassium are added to an ether solution of alpha-methyl styrene in an inert atmosphere to give dialkali metal adducts of trito hexa-alpha-methyl styrene, the addition being carried out at a temperature above the ceiling temperature for high polymer formation as defined in the Specification. Ethers specified are cyclic ethers such at tetrahydrofuran or 1.4-dioxane, or an aliphatic ether containing a methyl group such as dimethyl, methylethyl, methylisopropyl, methylbutyl, or methylpropyl ether or the dimethyl ether of ethylene glycol or mixtures thereof. The reaction is carried out at temperatures between -15 DEG and about 50 DEG C. and at a temperature at least 10 degrees above the ceiling temperature as defined. Air, oxygen, water and carbon dioxide should not be allowed to come into contact with the reactants, which should be carefully purified and reacted in an inert atmosphere, e.g helium or nitrogen. The product may be used as a catalyst in the polymerization of butadiene, isoprene, dimethylbutadiene, styrene, vinyltoluene, isopropylstyrene, tert. butyl styrene or alpha methyl styrene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1111761A GB923350A (en) | 1961-03-27 | 1961-03-27 | Alkali metal addition compounds of alpha-methyl styrene and method of making |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1111761A GB923350A (en) | 1961-03-27 | 1961-03-27 | Alkali metal addition compounds of alpha-methyl styrene and method of making |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB923350A true GB923350A (en) | 1963-04-10 |
Family
ID=9980352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1111761A Expired GB923350A (en) | 1961-03-27 | 1961-03-27 | Alkali metal addition compounds of alpha-methyl styrene and method of making |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB923350A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2275464A1 (en) * | 2005-06-15 | 2011-01-19 | Nippon Soda Co., Ltd. | Method for producing a polymer |
| US11591420B2 (en) | 2016-04-20 | 2023-02-28 | Albemarle Corporation | Process and catalyst for hydrogen mediated saline hydride initiated anionic chain transfer polymerization |
-
1961
- 1961-03-27 GB GB1111761A patent/GB923350A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2275464A1 (en) * | 2005-06-15 | 2011-01-19 | Nippon Soda Co., Ltd. | Method for producing a polymer |
| US8067515B2 (en) | 2005-06-15 | 2011-11-29 | Nippon Soda Co., Ltd. | Method of producing an acrylic acid-based polymer |
| US11591420B2 (en) | 2016-04-20 | 2023-02-28 | Albemarle Corporation | Process and catalyst for hydrogen mediated saline hydride initiated anionic chain transfer polymerization |
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