DD158785A1 - Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen - Google Patents

Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen Download PDF

Info

Publication number: DD158785A1
Authority: DD; German Democratic Republic
Prior art keywords: butadiene; polymerization; methyl; fractions; selective
Prior art date: 1980-08-29

Application number

DD22358480A

Other languages

German (de)

English (en)

Inventor

Elisabeth Anton

Miloslav Sufcak

Alexander Pleska

Otakar Seycek

Jiri Germak

Volker Griehl

Dieter Stubenrauch

Lothar Weber

Hans-Otto Froehlich

Winfried Mueller

Peter Scholz

Guenther Heublein

Original Assignee

Elisabeth Anton

Miloslav Sufcak

Alexander Pleska

Otakar Seycek

Jiri Germak

Volker Griehl

Dieter Stubenrauch

Lothar Weber

Froehlich Hans Otto

Winfried Mueller

Peter Scholz

Guenther Heublein

Priority date (The priority date 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 date listed.)

1980-08-29

Filing date

1980-08-29

Publication date

1983-02-02

1980-08-29 Application filed by Elisabeth Anton, Miloslav Sufcak, Alexander Pleska, Otakar Seycek, Jiri Germak, Volker Griehl, Dieter Stubenrauch, Lothar Weber, Froehlich Hans Otto, Winfried Mueller, Peter Scholz, Guenther Heublein filed Critical Elisabeth Anton

1980-08-29 Priority to DD22358480A priority Critical patent/DD158785A1/de

1981-07-22 Priority to CS560081A priority patent/CS228218B1/cs

1983-02-02 Publication of DD158785A1 publication Critical patent/DD158785A1/de

Links

238000006116 polymerization reaction Methods 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims abstract description 16
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 55
239000003999 initiator Substances 0.000 claims abstract description 11
229920001577 copolymer Polymers 0.000 claims abstract description 10
150000001993 dienes Chemical class 0.000 claims abstract description 7
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052744 lithium Inorganic materials 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 3
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
239000000178 monomer Substances 0.000 claims description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
229920001519 homopolymer Polymers 0.000 claims 1
239000007791 liquid phase Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 15
229920002857 polybutadiene Polymers 0.000 abstract description 10
239000000203 mixture Substances 0.000 abstract description 5
230000001588 bifunctional effect Effects 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 2
239000003208 petroleum Substances 0.000 abstract description 2
239000004215 Carbon black (E152) Substances 0.000 abstract 1
238000010348 incorporation Methods 0.000 abstract 1
238000000197 pyrolysis Methods 0.000 abstract 1
238000000926 separation method Methods 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009826 distribution Methods 0.000 description 3
-1 lithium organo compound Chemical class 0.000 description 3
239000012454 non-polar solvent Substances 0.000 description 3
239000003505 polymerization initiator Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
229920006250 telechelic polymer Polymers 0.000 description 3
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
239000005062 Polybutadiene Substances 0.000 description 2
238000010539 anionic addition polymerization reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000005661 deetherification reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000002900 organolithium compounds Chemical class 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
102000029797 Prion Human genes 0.000 description 1
108091000054 Prion Proteins 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
239000001273 butane Substances 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

DD22358480A 1980-08-29 1980-08-29 Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen DD158785A1 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD22358480A DD158785A1 (de)	1980-08-29	1980-08-29	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen
CS560081A CS228218B1 (de)	1980-08-29	1981-07-22	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD22358480A DD158785A1 (de)	1980-08-29	1980-08-29	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen

Publications (1)

Publication Number	Publication Date
DD158785A1 true DD158785A1 (de)	1983-02-02

Family

ID=5526046

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD22358480A DD158785A1 (de)	1980-08-29	1980-08-29	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen

Country Status (2)

Country	Link
CS (1)	CS228218B1 (cs)
DD (1)	DD158785A1 (cs)

1980
- 1980-08-29 DD DD22358480A patent/DD158785A1/de unknown
1981
- 1981-07-22 CS CS560081A patent/CS228218B1/cs unknown

Also Published As

Publication number	Publication date
CS228218B1 (de)	1984-05-14

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