DE1227657B - Verfahren zur Herstellung von elastromeren Butadien-Isobutylen-Mischpolymeren - Google Patents
Verfahren zur Herstellung von elastromeren Butadien-Isobutylen-MischpolymerenInfo
- Publication number
- DE1227657B DE1227657B DET23280A DET0023280A DE1227657B DE 1227657 B DE1227657 B DE 1227657B DE T23280 A DET23280 A DE T23280A DE T0023280 A DET0023280 A DE T0023280A DE 1227657 B DE1227657 B DE 1227657B
- Authority
- DE
- Germany
- Prior art keywords
- butadiene
- isobutylene
- catalyst
- titanium
- reaction
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 100
- 239000003054 catalyst Substances 0.000 claims description 37
- 229910052719 titanium Inorganic materials 0.000 claims description 25
- 239000010936 titanium Substances 0.000 claims description 25
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 24
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000007818 Grignard reagent Substances 0.000 claims description 9
- 150000004795 grignard reagents Chemical class 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 15
- 239000002002 slurry Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 7
- 239000005062 Polybutadiene Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- -1 naphthyl magnesium bromide Chemical compound 0.000 description 5
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- MBHQEXPGNCWWBP-UHFFFAOYSA-M magnesium;dodecane;bromide Chemical compound [Mg+2].[Br-].CCCCCCCCCCC[CH2-] MBHQEXPGNCWWBP-UHFFFAOYSA-M 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- PBGDIBQPASXECU-UHFFFAOYSA-N Br.Br.I.I Chemical compound Br.Br.I.I PBGDIBQPASXECU-UHFFFAOYSA-N 0.000 description 1
- MNVJLJILXBISNA-UHFFFAOYSA-M CCCCCCCCCCCCCCCCCC[Mg]I Chemical compound CCCCCCCCCCCCCCCCCC[Mg]I MNVJLJILXBISNA-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- PZIIGUMPOSVMSD-UHFFFAOYSA-M [Br-].C1=CC=C2C([Mg+])=CC=CC2=C1 Chemical compound [Br-].C1=CC=C2C([Mg+])=CC=CC2=C1 PZIIGUMPOSVMSD-UHFFFAOYSA-M 0.000 description 1
- MSAQSJXMDMTPBO-UHFFFAOYSA-M [Br-].CCCCCCCCCCCCCC[Mg+] Chemical compound [Br-].CCCCCCCCCCCCCC[Mg+] MSAQSJXMDMTPBO-UHFFFAOYSA-M 0.000 description 1
- VWXUBKNVYJBGPO-UHFFFAOYSA-M [Br-].[Mg+]CC#C Chemical compound [Br-].[Mg+]CC#C VWXUBKNVYJBGPO-UHFFFAOYSA-M 0.000 description 1
- MLQXWOJUAIIHLH-UHFFFAOYSA-M [F-].C(CCCCCCCC)[Mg+] Chemical compound [F-].C(CCCCCCCC)[Mg+] MLQXWOJUAIIHLH-UHFFFAOYSA-M 0.000 description 1
- RIWOQUPRLSKCGE-UHFFFAOYSA-M [F-].C(CCCCCCCCCCCCCCC)[Mg+] Chemical compound [F-].C(CCCCCCCCCCCCCCC)[Mg+] RIWOQUPRLSKCGE-UHFFFAOYSA-M 0.000 description 1
- TUWXWQHYZVBUPC-UHFFFAOYSA-M [I-].C(CCCCCCCC)[Mg+] Chemical compound [I-].C(CCCCCCCC)[Mg+] TUWXWQHYZVBUPC-UHFFFAOYSA-M 0.000 description 1
- CLGLRNZWNSOYFG-UHFFFAOYSA-M [I-].C(CCCCCCCCC)[Mg+] Chemical compound [I-].C(CCCCCCCCC)[Mg+] CLGLRNZWNSOYFG-UHFFFAOYSA-M 0.000 description 1
- NKFMCPGCTSYGGB-UHFFFAOYSA-M [I-].CC(C)(C)C1=CC=C(C[Mg+])C=C1 Chemical compound [I-].CC(C)(C)C1=CC=C(C[Mg+])C=C1 NKFMCPGCTSYGGB-UHFFFAOYSA-M 0.000 description 1
- KZRBNZDKAHWUJJ-UHFFFAOYSA-M [I-].CCCCCCCCCCCC[Mg+] Chemical compound [I-].CCCCCCCCCCCC[Mg+] KZRBNZDKAHWUJJ-UHFFFAOYSA-M 0.000 description 1
- FEAXVNMZZBOUNO-UHFFFAOYSA-M [I-].CCCCCC[Mg+] Chemical compound [I-].CCCCCC[Mg+] FEAXVNMZZBOUNO-UHFFFAOYSA-M 0.000 description 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 description 1
- GABKMLCWGNISMM-UHFFFAOYSA-J [Ti+4].[Br-].[I-].[I-].[I-] Chemical compound [Ti+4].[Br-].[I-].[I-].[I-] GABKMLCWGNISMM-UHFFFAOYSA-J 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KRDKZEKEJDGZNK-UHFFFAOYSA-N benzene;2-methylprop-1-ene Chemical group CC(C)=C.C1=CC=CC=C1 KRDKZEKEJDGZNK-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- ONDPARUELBWSEN-UHFFFAOYSA-J dichloro(diiodo)titanium Chemical compound [Cl-].[Cl-].[Ti+4].[I-].[I-] ONDPARUELBWSEN-UHFFFAOYSA-J 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 210000000003 hoof Anatomy 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- CFPKVQBKKLRQHZ-UHFFFAOYSA-M magnesium;3-methanidylheptane;bromide Chemical compound [Mg+2].[Br-].CCCCC([CH2-])CC CFPKVQBKKLRQHZ-UHFFFAOYSA-M 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—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
- C08F236/04—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
- C08F236/06—Butadiene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16385562A | 1962-01-02 | 1962-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1227657B true DE1227657B (de) | 1966-10-27 |
Family
ID=22591867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET23280A Pending DE1227657B (de) | 1962-01-02 | 1962-12-29 | Verfahren zur Herstellung von elastromeren Butadien-Isobutylen-Mischpolymeren |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE1227657B (enrdf_load_stackoverflow) |
| GB (1) | GB1004942A (enrdf_load_stackoverflow) |
| LU (1) | LU42953A1 (enrdf_load_stackoverflow) |
| NL (2) | NL287325A (enrdf_load_stackoverflow) |
| SE (1) | SE316614B (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543292A (enrdf_load_stackoverflow) * | 1954-12-02 | |||
| GB776326A (en) * | 1954-08-16 | 1957-06-05 | Du Pont | Improvements in or relating to the polymerisation of dienes having terminal ethylenic unsaturation |
-
0
- NL NL123757D patent/NL123757C/xx active
- NL NL287325D patent/NL287325A/xx unknown
-
1962
- 1962-12-27 SE SE1398462A patent/SE316614B/xx unknown
- 1962-12-29 DE DET23280A patent/DE1227657B/de active Pending
- 1962-12-29 LU LU42953D patent/LU42953A1/xx unknown
-
1963
- 1963-01-07 GB GB68463A patent/GB1004942A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB776326A (en) * | 1954-08-16 | 1957-06-05 | Du Pont | Improvements in or relating to the polymerisation of dienes having terminal ethylenic unsaturation |
| BE543292A (enrdf_load_stackoverflow) * | 1954-12-02 |
Also Published As
| Publication number | Publication date |
|---|---|
| SE316614B (enrdf_load_stackoverflow) | 1969-10-27 |
| LU42953A1 (enrdf_load_stackoverflow) | 1963-12-29 |
| NL123757C (enrdf_load_stackoverflow) | |
| GB1004942A (en) | 1965-09-22 |
| NL287325A (enrdf_load_stackoverflow) |
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