DD237669A1 - Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen - Google Patents

Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen Download PDF

Info

Publication number: DD237669A1
Authority: DD; German Democratic Republic
Prior art keywords: butadiene; polymers; polymerization; divinylbenzene; mixtures
Prior art date: 1982-11-29

Application number

DD24528382A

Other languages

German (de)

English (en)

Inventor

Volker Griehl

Elisabeth Anton

Dieter Stubenrauch

Original Assignee

Buna Chem Werke Veb

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.)

1982-11-29

Filing date

1982-11-29

Publication date

1986-07-23

1982-11-29 Application filed by Buna Chem Werke Veb filed Critical Buna Chem Werke Veb

1982-11-29 Priority to DD24528382A priority Critical patent/DD237669A1/de

1983-11-10 Priority to CS828083A priority patent/CS252655B1/cs

1986-07-23 Publication of DD237669A1 publication Critical patent/DD237669A1/de

Links

KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 50
238000000034 method Methods 0.000 title claims abstract description 17
238000006116 polymerization reaction Methods 0.000 title claims abstract description 17
229920000642 polymer Polymers 0.000 claims abstract description 36
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 23
239000003999 initiator Substances 0.000 claims abstract description 16
239000000203 mixture Substances 0.000 claims abstract description 15
239000007795 chemical reaction product Substances 0.000 claims abstract description 3
239000003153 chemical reaction reagent Substances 0.000 claims abstract 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
-1 alkyl monolithium Chemical compound 0.000 claims description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims description 3
229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000001569 carbon dioxide Substances 0.000 claims description 2
238000007306 functionalization reaction Methods 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
229920002857 polybutadiene Polymers 0.000 abstract description 11
229920001002 functional polymer Polymers 0.000 abstract description 2
238000000926 separation method Methods 0.000 abstract description 2
239000000470 constituent Substances 0.000 abstract 1
238000010348 incorporation Methods 0.000 abstract 1
150000002894 organic compounds Chemical class 0.000 abstract 1
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 4
PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000003505 polymerization initiator 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
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
239000005062 Polybutadiene Substances 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
230000001588 bifunctional effect Effects 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 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
WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-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
239000004215 Carbon black (E152) Substances 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
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
239000001273 butane Substances 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000008878 coupling Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005336 cracking Methods 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
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012535 impurity 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
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
229920006216 polyvinyl aromatic Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229920013730 reactive polymer Polymers 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229920002554 vinyl polymer Polymers 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

Landscapes

Chemical & Material Sciences (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerization Catalysts (AREA)

DD24528382A 1982-11-29 1982-11-29 Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen DD237669A1 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD24528382A DD237669A1 (de)	1982-11-29	1982-11-29	Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen
CS828083A CS252655B1 (en)	1982-11-29	1983-11-10	Method of 1,3-butadiene's selective polymerization from c4-fractions

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD24528382A DD237669A1 (de)	1982-11-29	1982-11-29	Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen

Publications (1)

Publication Number	Publication Date
DD237669A1 true DD237669A1 (de)	1986-07-23

Family

ID=5542766

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD24528382A DD237669A1 (de)	1982-11-29	1982-11-29	Verfahren zur selektivpolymerisation von butadien aus c tief 4 fraktionen

Country Status (2)

Country	Link
CS (1)	CS252655B1 (cs)
DD (1)	DD237669A1 (cs)

1982
- 1982-11-29 DD DD24528382A patent/DD237669A1/de not_active IP Right Cessation
1983
- 1983-11-10 CS CS828083A patent/CS252655B1/cs unknown

Also Published As

Publication number	Publication date
CS252655B1 (en)	1987-09-17

Legal Events

Date	Code	Title	Description
1994-03-17	ENJ	Ceased due to non-payment of renewal fee

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