CS240557B1 - 1,3 butadiene selective polymerization method from c4 fractions - Google Patents

1,3 butadiene selective polymerization method from c4 fractions Download PDF

Info

Publication number: CS240557B1
Authority: CS; Czechoslovakia
Prior art keywords: polymerization; initiators; butadiene; molecular weight; polymers
Prior art date: 1982-11-17

Application number

CS838277A

Other languages

Czech (cs)

English (en)

Other versions

CS827783A1 (en

Inventor

Volker Griehl

Elisabeth Anton

Dieter Stubenrauch

Original Assignee

Volker Griehl

Elisabeth Anton

Dieter Stubenrauch

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.)

1982-11-17

Filing date

1983-11-10

Publication date

1986-02-13

1983-11-10 Application filed by Volker Griehl, Elisabeth Anton, Dieter Stubenrauch filed Critical Volker Griehl

1985-07-16 Publication of CS827783A1 publication Critical patent/CS827783A1/cs

1986-02-13 Publication of CS240557B1 publication Critical patent/CS240557B1/cs

Links

238000006116 polymerization reaction Methods 0.000 title claims description 20
238000000034 method Methods 0.000 title claims description 15
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title description 15
239000003999 initiator Substances 0.000 claims description 21
229920000642 polymer Polymers 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 10
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
239000001569 carbon dioxide Substances 0.000 claims description 4
229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
238000007306 functionalization reaction Methods 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 claims description 3
WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
229920002857 polybutadiene Polymers 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 5
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
230000001588 bifunctional effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003505 polymerization initiator Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
238000010539 anionic addition polymerization reaction Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
-1 monolithium compound Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
150000002900 organolithium compounds Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
229920006250 telechelic polymer Polymers 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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
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
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002642 lithium compounds Chemical class 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
239000012454 non-polar solvent Substances 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920006216 polyvinyl aromatic Polymers 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920013730 reactive polymer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
- 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)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerization Catalysts (AREA)

CS838277A 1982-11-17 1983-11-10 1,3 butadiene selective polymerization method from c4 fractions CS240557B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD24494682A DD237667A1 (de)	1982-11-17	1982-11-17	Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen

Publications (2)

Publication Number	Publication Date
CS827783A1 CS827783A1 (en)	1985-07-16
CS240557B1 true CS240557B1 (en)	1986-02-13

Family

ID=5542504

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS838277A CS240557B1 (en)	1982-11-17	1983-11-10	1,3 butadiene selective polymerization method from c4 fractions

Country Status (2)

Country	Link
CS (1)	CS240557B1 (de)
DD (1)	DD237667A1 (de)

1982
- 1982-11-17 DD DD24494682A patent/DD237667A1/de not_active IP Right Cessation
1983
- 1983-11-10 CS CS838277A patent/CS240557B1/cs unknown

Also Published As

Publication number	Publication date
CS827783A1 (en)	1985-07-16
DD237667A1 (de)	1986-07-23

Publication	Publication Date	Title
EP0002864A1 (de)	1979-07-11	Verfahren zur Herstellung von linearen und/oder radialen Polymerisaten
CN113831469B (zh)	2023-07-25	超支化丁基橡胶的制备方法
EP0501957B1 (de)	1996-07-17	Elastomere pfropfcopolymere und ihre verwendung als kompatibilisierungsmittel
KR100204815B1 (ko)	1999-06-15	수소화된 중합체 용액으로부터 제8족 금속을 함유한 수소화 촉매의 제거방법
EP0711789A2 (de)	1996-05-15	Kernfuntionalisierte Sternblockcopolymere
CS240557B1 (en)	1986-02-13	1,3 butadiene selective polymerization method from c4 fractions
EP0856532B1 (de)	2001-09-26	Anionische Copolymerisation von konjugierten Dienen und Vinylarenen in Gegenwart von Alkylether von Tetrahydropyranylmethanol
US5281696A (en)	1994-01-25	Removal of hydrogenation catalyst from polymer solutions by trialkyl aluminum precipitation
JP3157033B2 (ja)	2001-04-16	末端変性共役ジエン系重合体の製造方法
GB2124228A (en)	1984-02-15	Organo-lithium polymerization initiator
CN113831473A (zh)	2021-12-24	一种超宽分子量分布、超支化丁基橡胶的制备方法
JPH0363963B2 (de)	1991-10-03
CN108028405B (zh)	2020-05-12	含胺的多链烯基偶联剂和由其制备的聚合物
CS240558B1 (cs)	1986-02-13	: Zpuscbselektivní polymerace butadienU’l,3z Cýfrakcí
US6384164B2 (en)	2002-05-07	Process for the preparation of a branched diene elastomer via an anionic route
CN113831466A (zh)	2021-12-24	超支化、超宽分子量分布丁基橡胶的制备方法
Jou et al.	1997	Efficiency of n-butyllithium/m-diisopropenylbenzene diadduct as a dicarbanion initiator in the making of α, ω-hydroxyl terminated polybutadiene using oxetane as the capping agent
CS240556B1 (cs)	1986-02-13	Způsob selektivní polymeracfi butadiénii-1,3 z Ci frakcí
CS252655B1 (en)	1987-09-17	Method of 1,3-butadiene's selective polymerization from c4-fractions
CS217319B1 (en)	1982-12-31	Method of selective polymeration of the butadien z c 4 fraction
RU2082720C1 (ru)	1997-06-27	Способ получения низкомолекулярного полибутадиена
CS237590B1 (en)	1985-09-17	Method of homopolymers and copolymers of 1,3-dienes preparation with terminal functional groups
CS237290B1 (en)	1985-07-16	Processing of polymere diene with ending functional groups
CS237591B1 (en)	1985-09-17	Method of butadiene selective polymerization from c4 fractions into star homopolymers and copolymers
SU979367A1 (ru)	1982-12-07	Способ селективной полимеризации бутадиена из с @ -фракции