DD158779A1 - 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: DD158779A1
Authority: DD; German Democratic Republic
Prior art keywords: polymerization; butadiene; bis; polymers; copolymers
Prior art date: 1980-03-05

Application number

DD21945280A

Other languages

German (de)

English (en)

Inventor

Guenther Heublein

Hans-Otto Froehlich

Stephan Keiser

Christa Haroske

Elisabeth Anton

Peter Scholz

Original Assignee

Guenther Heublein

Froehlich Hans Otto

Stephan Keiser

Christa Haroske

Elisabeth Anton

Peter Scholz

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.)

1980-03-05

Filing date

1980-03-05

Publication date

1983-02-02

1980-03-05 Application filed by Guenther Heublein, Froehlich Hans Otto, Stephan Keiser, Christa Haroske, Elisabeth Anton, Peter Scholz filed Critical Guenther Heublein

1980-03-05 Priority to DD21945280A priority Critical patent/DD158779A1/de

1980-12-09 Priority to CS862280A priority patent/CS224501B1/cs

1983-02-02 Publication of DD158779A1 publication Critical patent/DD158779A1/de

Links

238000006116 polymerization reaction Methods 0.000 title claims abstract description 26
238000000034 method Methods 0.000 title claims abstract description 21
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 78
229920000642 polymer Polymers 0.000 claims abstract description 30
239000000178 monomer Substances 0.000 claims abstract description 11
229920001577 copolymer Polymers 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 6
239000003999 initiator Substances 0.000 claims description 31
229910052744 lithium Inorganic materials 0.000 claims description 10
-1 oC-methylstyrene Chemical compound 0.000 claims description 10
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
239000001273 butane Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 5
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 4
239000012071 phase Substances 0.000 claims description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
239000007791 liquid phase Substances 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
150000002596 lactones Chemical class 0.000 claims 1
229920005604 random copolymer Polymers 0.000 claims 1
229920002857 polybutadiene Polymers 0.000 abstract description 10
230000001588 bifunctional effect Effects 0.000 abstract description 6
238000000926 separation method Methods 0.000 abstract description 4
238000010348 incorporation Methods 0.000 abstract 1
239000004615 ingredient Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 9
239000005062 Polybutadiene Substances 0.000 description 8
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
UKNCZDKRZFIVQR-UHFFFAOYSA-N [Li]C1=CC=C(OC(C(C)OC2=CC=C(C=C2)[Li])C)C=C1 Chemical compound [Li]C1=CC=C(OC(C(C)OC2=CC=C(C=C2)[Li])C)C=C1 UKNCZDKRZFIVQR-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000012454 non-polar solvent Substances 0.000 description 4
239000003505 polymerization initiator Substances 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
238000010539 anionic addition polymerization reaction Methods 0.000 description 3
229930188620 butyrolactone Natural products 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
DCIIYQZOWPDBFM-UHFFFAOYSA-N [Li]C1=C(OC(C)C(C)OC2=C(C=CC=C2)[Li])C=CC=C1 Chemical compound [Li]C1=C(OC(C)C(C)OC2=C(C=CC=C2)[Li])C=CC=C1 DCIIYQZOWPDBFM-UHFFFAOYSA-N 0.000 description 2
PHKFIVPXQYKLMC-UHFFFAOYSA-N [Li]C1=C(OC(C)OC2=C(C=CC=C2)[Li])C=CC=C1 Chemical compound [Li]C1=C(OC(C)OC2=C(C=CC=C2)[Li])C=CC=C1 PHKFIVPXQYKLMC-UHFFFAOYSA-N 0.000 description 2
150000000475 acetylene derivatives Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
238000006263 metalation reaction Methods 0.000 description 2
125000001979 organolithium group Chemical group 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000000197 pyrolysis Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229920005603 alternating copolymer Polymers 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical class CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
150000004985 diamines Chemical group 0.000 description 1
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
RXGDGBFPBCUIMS-UHFFFAOYSA-N dilithium;butane Chemical compound [Li+].[Li+].[CH2-]CC[CH2-] RXGDGBFPBCUIMS-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
229920001002 functional polymer Polymers 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
TURVPWZPNVDDMU-UHFFFAOYSA-N lithium;phenol Chemical compound [Li].[Li].OC1=CC=CC=C1.OC1=CC=CC=C1 TURVPWZPNVDDMU-UHFFFAOYSA-N 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000000463 material Substances 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920006216 polyvinyl aromatic Polymers 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920006250 telechelic polymer Polymers 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000000214 vapour pressure osmometry Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

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

DD21945280A 1980-03-05 1980-03-05 Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen DD158779A1 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD21945280A DD158779A1 (de)	1980-03-05	1980-03-05	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen
CS862280A CS224501B1 (en)	1980-03-05	1980-12-09	Process for selective polymerization of butadien from c4 fraction

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD21945280A DD158779A1 (de)	1980-03-05	1980-03-05	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen

Publications (1)

Publication Number	Publication Date
DD158779A1 true DD158779A1 (de)	1983-02-02

Family

ID=5522989

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD21945280A DD158779A1 (de)	1980-03-05	1980-03-05	Verfahren zur selektiven butadien-polymerisation aus c tief 4-fraktionen

Country Status (2)

Country	Link
CS (1)	CS224501B1 (cs)
DD (1)	DD158779A1 (cs)

1980
- 1980-03-05 DD DD21945280A patent/DD158779A1/de unknown
- 1980-12-09 CS CS862280A patent/CS224501B1/cs unknown

Also Published As

Publication number	Publication date
CS224501B1 (en)	1984-01-16

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