CA1160206A - Process for the copolymerisation of ethylene with polyunsaturated hydrocarbons - Google Patents
Process for the copolymerisation of ethylene with polyunsaturated hydrocarbonsInfo
- Publication number
- CA1160206A CA1160206A CA000346920A CA346920A CA1160206A CA 1160206 A CA1160206 A CA 1160206A CA 000346920 A CA000346920 A CA 000346920A CA 346920 A CA346920 A CA 346920A CA 1160206 A CA1160206 A CA 1160206A
- Authority
- CA
- Canada
- Prior art keywords
- metal
- ethylene
- halogen donor
- compound
- catalyst
- 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.)
- Expired
Links
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 239000005977 Ethylene Substances 0.000 title claims abstract description 46
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 42
- 230000008569 process Effects 0.000 title claims description 37
- 150000002430 hydrocarbons Chemical class 0.000 title abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
- 150000002367 halogens Chemical class 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 claims abstract description 29
- 239000002184 metal Substances 0.000 claims abstract description 29
- 230000003197 catalytic effect Effects 0.000 claims abstract description 26
- 230000000737 periodic effect Effects 0.000 claims abstract description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 34
- 239000010936 titanium Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 23
- 150000003609 titanium compounds Chemical class 0.000 claims description 23
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 20
- -1 alicyclic hydrocarbons Chemical class 0.000 claims description 19
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 17
- 229910052719 titanium Inorganic materials 0.000 claims description 17
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 16
- 229920000098 polyolefin Polymers 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 4
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000001500 aryl chlorides Chemical class 0.000 claims description 4
- 229910008046 SnC14 Inorganic materials 0.000 claims description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 4
- 230000005494 condensation Effects 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 150000002899 organoaluminium compounds Chemical class 0.000 claims 3
- 229910006113 GeCl4 Inorganic materials 0.000 claims 2
- 229910019213 POCl3 Inorganic materials 0.000 claims 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 2
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 claims 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 abstract description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000011572 manganese Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 101000798109 Homo sapiens Melanotransferrin Proteins 0.000 description 5
- 102100032239 Melanotransferrin Human genes 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229910052748 manganese Inorganic materials 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 229910010066 TiC14 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000010210 aluminium Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical class CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000006353 environmental stress Effects 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000005376 secondary alkyl halides Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000005377 tertiary alkyl halides Chemical class 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20799/79A IT1115152B (it) | 1979-03-07 | 1979-03-07 | Processo per la copolimerizzazione dell'etilene con idrocarburi pluriinsaturi |
| IT20799A/79 | 1979-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160206A true CA1160206A (en) | 1984-01-10 |
Family
ID=11172228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000346920A Expired CA1160206A (en) | 1979-03-07 | 1980-03-04 | Process for the copolymerisation of ethylene with polyunsaturated hydrocarbons |
Country Status (12)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1137631B (it) * | 1981-07-29 | 1986-09-10 | Anic Spa | Procedimento per la polimerizzazione e copolimerizzazione in alta resa di composti olefinicamente insaturi e mezzi adatti allo socpo |
| US4650778A (en) * | 1985-01-18 | 1987-03-17 | E. I. Du Pont De Nemours And Company | Metal halide vaporization into diluents |
| US4740570A (en) * | 1985-01-18 | 1988-04-26 | E. I. Du Pont De Nemours And Company | Metal halide vaporization into diluents |
| IN172494B (enrdf_load_stackoverflow) * | 1986-12-19 | 1993-09-04 | Exxon Chemical Patents Inc | |
| JP5961483B2 (ja) * | 2012-08-20 | 2016-08-02 | 株式会社ブリヂストン | 共重合体の製造方法 |
-
1979
- 1979-03-07 IT IT20799/79A patent/IT1115152B/it active
-
1980
- 1980-02-28 GB GB8006838A patent/GB2045779B/en not_active Expired
- 1980-03-04 CA CA000346920A patent/CA1160206A/en not_active Expired
- 1980-03-05 SE SE8001726A patent/SE449616B/sv not_active IP Right Cessation
- 1980-03-05 ZA ZA00801281A patent/ZA801281B/xx unknown
- 1980-03-06 CH CH1784/80A patent/CH647535A5/it not_active IP Right Cessation
- 1980-03-06 LU LU82229A patent/LU82229A1/fr unknown
- 1980-03-06 FR FR8005072A patent/FR2450846B1/fr not_active Expired
- 1980-03-07 BE BE0/199719A patent/BE882134A/fr not_active IP Right Cessation
- 1980-03-07 NL NL8001389A patent/NL8001389A/nl not_active Application Discontinuation
- 1980-03-07 DE DE19803008833 patent/DE3008833A1/de not_active Ceased
- 1980-03-07 JP JP2820080A patent/JPS55144008A/ja active Granted
- 1980-09-04 FR FR8019144A patent/FR2465755A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2450846B1 (fr) | 1986-05-23 |
| SE8001726L (sv) | 1980-09-08 |
| CH647535A5 (it) | 1985-01-31 |
| BE882134A (fr) | 1980-09-08 |
| FR2450846A1 (fr) | 1980-10-03 |
| GB2045779A (en) | 1980-11-05 |
| FR2465755A1 (fr) | 1981-03-27 |
| FR2465755B1 (enrdf_load_stackoverflow) | 1983-07-18 |
| SE449616B (sv) | 1987-05-11 |
| IT7920799A0 (it) | 1979-03-07 |
| LU82229A1 (fr) | 1980-09-24 |
| IT1115152B (it) | 1986-02-03 |
| JPH0118084B2 (enrdf_load_stackoverflow) | 1989-04-04 |
| JPS55144008A (en) | 1980-11-10 |
| DE3008833A1 (de) | 1980-09-25 |
| ZA801281B (en) | 1981-03-25 |
| NL8001389A (nl) | 1980-09-09 |
| GB2045779B (en) | 1983-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |