CA1115447A - Procede d'obtention de polymeres ou de copolymeres d'olefines - Google Patents

Procede d'obtention de polymeres ou de copolymeres d'olefines

Info

Publication number: CA1115447A
Authority: CA; Canada
Prior art keywords: titanium; compound; reaction; magnesium; carbon atoms
Prior art date: 1976-08-27
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

Application number

CA285,572A

Other languages

English (en)

Inventor

Syuji Minami

Akinori Toyota

Norio Kashiwa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsui Chemicals Inc

Original Assignee

Mitsui Petrochemical Industries Ltd

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.)

1976-08-27

Filing date

1977-08-26

Publication date

1981-12-29

1977-08-26 Application filed by Mitsui Petrochemical Industries Ltd filed Critical Mitsui Petrochemical Industries Ltd

1981-12-29 Application granted granted Critical

1981-12-29 Publication of CA1115447A publication Critical patent/CA1115447A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
229920000098 polyolefin Polymers 0.000 title claims description 4
229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 3
238000000034 method Methods 0.000 claims abstract description 65
239000010936 titanium Substances 0.000 claims abstract description 64
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 63
229910052719 titanium Inorganic materials 0.000 claims abstract description 63
239000007787 solid Substances 0.000 claims abstract description 47
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 33
229910052749 magnesium Inorganic materials 0.000 claims abstract description 33
239000011777 magnesium Substances 0.000 claims abstract description 32
239000003054 catalyst Substances 0.000 claims abstract description 20
229910052751 metal Inorganic materials 0.000 claims abstract description 17
239000002184 metal Substances 0.000 claims abstract description 17
150000002902 organometallic compounds Chemical class 0.000 claims abstract description 16
150000001336 alkenes Chemical class 0.000 claims abstract description 11
230000000737 periodic effect Effects 0.000 claims abstract description 7
230000000379 polymerizing effect Effects 0.000 claims abstract description 3
-1 organic acid esters Chemical class 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 37
235000001055 magnesium Nutrition 0.000 claims description 29
238000006116 polymerization reaction Methods 0.000 claims description 29
229940091250 magnesium supplement Drugs 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 14
150000008065 acid anhydrides Chemical class 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 8
150000002170 ethers Chemical class 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
239000007791 liquid phase Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
239000012808 vapor phase Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 2
239000007810 chemical reaction solvent Substances 0.000 claims 2
150000007524 organic acids Chemical class 0.000 abstract description 4
229920001577 copolymer Polymers 0.000 abstract description 3
239000000306 component Substances 0.000 description 38
150000002681 magnesium compounds Chemical class 0.000 description 31
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
150000003609 titanium compounds Chemical class 0.000 description 29
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 24
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
235000010210 aluminium Nutrition 0.000 description 16
229920000642 polymer Polymers 0.000 description 15
229910052782 aluminium Inorganic materials 0.000 description 13
239000007788 liquid Substances 0.000 description 13
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 13
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 13
239000007795 chemical reaction product Substances 0.000 description 12
239000003350 kerosene Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
229910052710 silicon Inorganic materials 0.000 description 12
239000010703 silicon Substances 0.000 description 12
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
229910052718 tin Inorganic materials 0.000 description 10
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 10
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
239000000843 powder Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000004743 Polypropylene Substances 0.000 description 8
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
238000007334 copolymerization reaction Methods 0.000 description 8
125000005234 alkyl aluminium group Chemical group 0.000 description 7
238000009835 boiling Methods 0.000 description 7
238000000605 extraction Methods 0.000 description 7
239000000155 melt Substances 0.000 description 7
229920001155 polypropylene Polymers 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
229910001220 stainless steel Inorganic materials 0.000 description 6
239000010935 stainless steel Substances 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
150000003377 silicon compounds Chemical class 0.000 description 5
150000003606 tin compounds Chemical class 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052732 germanium Inorganic materials 0.000 description 4
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000010298 pulverizing process Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
229920000576 tactic polymer Polymers 0.000 description 3
235000016804 zinc Nutrition 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
MRFOXZHVXHEJIU-UHFFFAOYSA-N 3-butyl-4-methylideneoxolane-2,5-dione Chemical compound CCCCC1C(=O)OC(=O)C1=C MRFOXZHVXHEJIU-UHFFFAOYSA-N 0.000 description 2
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000002083 X-ray spectrum Methods 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229920006125 amorphous polymer Polymers 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000010908 decantation Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
229940093470 ethylene Drugs 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
125000000962 organic group Chemical group 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000012265 solid product Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 1
NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
HXFIRQHMXJBTRV-UHFFFAOYSA-N 3,4-dimethyloxolane-2,5-dione Chemical compound CC1C(C)C(=O)OC1=O HXFIRQHMXJBTRV-UHFFFAOYSA-N 0.000 description 1
NSJAWXMCLJVBPM-UHFFFAOYSA-N 3-butyloxolane-2,5-dione Chemical compound CCCCC1CC(=O)OC1=O NSJAWXMCLJVBPM-UHFFFAOYSA-N 0.000 description 1
YRTGWRSQRUHPKX-UHFFFAOYSA-N 3-ethyloxolane-2,5-dione Chemical compound CCC1CC(=O)OC1=O YRTGWRSQRUHPKX-UHFFFAOYSA-N 0.000 description 1
AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
YQLVIOYSGHEJDA-UHFFFAOYSA-N 3-methyloxane-2,6-dione Chemical compound CC1CCC(=O)OC1=O YQLVIOYSGHEJDA-UHFFFAOYSA-N 0.000 description 1
DFATXMYLKPCSCX-UHFFFAOYSA-N 3-methylsuccinic anhydride Chemical compound CC1CC(=O)OC1=O DFATXMYLKPCSCX-UHFFFAOYSA-N 0.000 description 1
ZJFCVUTYZHUNSW-UHFFFAOYSA-N 3-octadecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC1CC(=O)OC1=O ZJFCVUTYZHUNSW-UHFFFAOYSA-N 0.000 description 1
OAJCSERLBQROJC-UHFFFAOYSA-N 3-octyloxolane-2,5-dione Chemical compound CCCCCCCCC1CC(=O)OC1=O OAJCSERLBQROJC-UHFFFAOYSA-N 0.000 description 1
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 1
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 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
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229910010066 TiC14 Inorganic materials 0.000 description 1
229910010386 TiI4 Inorganic materials 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910052925 anhydrite Inorganic materials 0.000 description 1
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
238000012661 block copolymerization Methods 0.000 description 1
JKFJJYOIWGFQGI-UHFFFAOYSA-M bromo-bis(2-methylpropyl)alumane Chemical compound [Br-].CC(C)C[Al+]CC(C)C JKFJJYOIWGFQGI-UHFFFAOYSA-M 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
SHOVVTSKTTYFGP-UHFFFAOYSA-L butylaluminum(2+);dichloride Chemical compound CCCC[Al](Cl)Cl SHOVVTSKTTYFGP-UHFFFAOYSA-L 0.000 description 1
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
KBLZFQBDODEHJH-UHFFFAOYSA-N dibutylalumane Chemical compound C(CCC)[AlH]CCCC KBLZFQBDODEHJH-UHFFFAOYSA-N 0.000 description 1
HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
IWYBVQLPTCMVFO-UHFFFAOYSA-N ethyl 2,2-dichloroacetate Chemical compound CCOC(=O)C(Cl)Cl IWYBVQLPTCMVFO-UHFFFAOYSA-N 0.000 description 1
OUZCDRGUTZLAGO-UHFFFAOYSA-N ethyl 2-ethoxybenzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCC OUZCDRGUTZLAGO-UHFFFAOYSA-N 0.000 description 1
XSXVXSCMWUJXOS-UHFFFAOYSA-N ethyl 2-ethylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1CC XSXVXSCMWUJXOS-UHFFFAOYSA-N 0.000 description 1
NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 description 1
JJOYCHKVKWDMEA-UHFFFAOYSA-N ethyl cyclohexanecarboxylate Chemical compound CCOC(=O)C1CCCCC1 JJOYCHKVKWDMEA-UHFFFAOYSA-N 0.000 description 1
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical group 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
229910001635 magnesium fluoride Inorganic materials 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 1
OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
VECVSKFWRQYTAL-UHFFFAOYSA-N octyl benzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1 VECVSKFWRQYTAL-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 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
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-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
KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
235000014786 phosphorus Nutrition 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000000725 suspension Substances 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
229910000083 tin tetrahydride Inorganic materials 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003739 xylenols Chemical class 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/02—Carriers therefor
- C08F4/022—Magnesium halide as support anhydrous or hydrated or complexed by means of a Lewis base for Ziegler-type catalysts

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

CA285,572A 1976-08-27 1977-08-26 Procede d'obtention de polymeres ou de copolymeres d'olefines Expired CA1115447A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP51101565A JPS5812888B2 (ja)	1976-08-27	1976-08-27	ポリオレフインの製造方法
JP101565/76		1976-08-27

Publications (1)

Publication Number	Publication Date
CA1115447A true CA1115447A (fr)	1981-12-29

Family

ID=14303921

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA285,572A Expired CA1115447A (fr)	1976-08-27	1977-08-26	Procede d'obtention de polymeres ou de copolymeres d'olefines

Country Status (17)

Country	Link
JP (1)	JPS5812888B2 (fr)
AT (1)	AT350258B (fr)
AU (1)	AU510626B2 (fr)
BE (1)	BE858156A (fr)
BR (1)	BR7705674A (fr)
CA (1)	CA1115447A (fr)
DE (1)	DE2738627A1 (fr)
ES (1)	ES462114A1 (fr)
FR (1)	FR2362868A1 (fr)
GB (1)	GB1564460A (fr)
IT (1)	IT1084731B (fr)
NL (1)	NL177831C (fr)
NO (1)	NO152753C (fr)
PH (1)	PH15738A (fr)
PT (1)	PT66956B (fr)
SE (1)	SE438862B (fr)
ZA (1)	ZA775067B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6025441B2 (ja) *	1976-09-30	1985-06-18	三井化学株式会社	固体触媒成分及びオレフィン重合用触媒
ZA801724B (en) *	1979-04-01	1981-03-25	Stamicarbon	Catalytic titanium compound,process for the manufacture thereof,and process for the polymerization of lakenes-1 with application of such a titanium component
JPS55135105A (en) *	1979-04-10	1980-10-21	Mitsui Petrochem Ind Ltd	Titanium catalyst component for olefin polymerization
EP0029623B1 (fr)	1979-11-20	1984-06-13	Shell Internationale Researchmaatschappij B.V.	Préparation de composants de catalyseur et polymérisation d'oléfines à l'aide de ces composants de catalyseur
JPS56166205A (en) *	1980-05-23	1981-12-21	Idemitsu Kosan Co Ltd	Stereoregular polymerization of alpha-olefin
JPS5721403A (en) *	1980-07-11	1982-02-04	Mitsui Toatsu Chem Inc	Polymerization of alpha-olefin
JPS5770105A (en) *	1980-10-17	1982-04-30	Toa Nenryo Kogyo Kk	Catalytic component for alpha-olefin polymerization and its use
US4680350A (en) *	1981-09-10	1987-07-14	Stauffer Chemical Company	Purified catalyst support
US4419269A (en)	1982-12-06	1983-12-06	The Dow Chemical Company	Transition metal containing catalyst
EP0146544A4 (fr) *	1983-06-06	1985-12-11	Dow Chemical Co	PROCEDE DE POLYMERISATION D'OLEFINES UTILISANT UN CATALYSEUR PREPARE A PARTIR D'UN COMPOSE D'ORGANO-MAGNESIUM; COMPOSE CONTENANT DE l'OXYGENE OU DE L'AZOTE; SOURCE D'HALOGENURE; COMPOSE DE METAL DE TRANSITION ET AGENT REDUCTEUR.
EP0246599B1 (fr) *	1986-05-21	1991-01-30	Mitsubishi Kasei Corporation	Procédé de production d'un polymère d'oléfine
US5608018A (en) *	1993-12-08	1997-03-04	Sumitomo Chemical Company, Limited	α-olefin polymerization catalyst system and process for producing α-olefin catalyst
EP2454293B1 (fr) *	2009-07-14	2013-08-21	Basell Poliolefine Italia S.r.l.	Procédé pour la préparation d'un polymère de 1-butène
CN111234073B (zh) *	2018-11-29	2021-12-31	中国石油化工股份有限公司	用于烯烃聚合的催化剂组分、催化剂体系和预聚合催化剂及其应用以及烯烃聚合方法
CN111234070B (zh) *	2018-11-29	2022-03-01	中国石油化工股份有限公司	用于烯烃聚合的催化剂组分、催化剂体系和预聚合催化剂及其应用以及烯烃聚合方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3402113A (en) *	1965-04-27	1968-09-17	Lummus Co	Process for the electrolysis of alkali metal halide brines
NL160286C (fr) *	1971-06-25
IT967867B (it) *	1972-09-26	1974-03-11	Montedison Spa	Procedimento per la polimerizzazio ne stereospecifica delle alfa ole fine
GB1492618A (en) *	1974-02-01	1977-11-23	Mitsui Petrochemical Ind	Process for preparing highly stereoregular polyolefins and catalyst used therefor
IT1005486B (it) *	1974-02-15	1976-08-20	Montedison Spa	Gomme termoplastiche e processo per la loro preparazione
JPS5128189A (ja) *	1974-09-03	1976-03-09	Mitsui Petrochemical Ind	Koketsushoseihoriorefuin no kokatsuseijugohoho
JPS565404B2 (fr) *	1975-02-14	1981-02-04
DE2553104A1 (de) *	1975-11-26	1977-06-08	Mitsui Petrochemical Ind	Verfahren zur herstellung einer auf einen traeger mit hoher leistungsfaehigkeit aufgebrachten katalysatorkomponente

1976
- 1976-08-27 JP JP51101565A patent/JPS5812888B2/ja not_active Expired
1977
- 1977-08-19 NO NO772897A patent/NO152753C/no unknown
- 1977-08-22 ZA ZA00775067A patent/ZA775067B/xx unknown
- 1977-08-23 GB GB35312/77A patent/GB1564460A/en not_active Expired
- 1977-08-24 AT AT613677A patent/AT350258B/de not_active IP Right Cessation
- 1977-08-25 BR BR7705674A patent/BR7705674A/pt unknown
- 1977-08-25 PT PT66956A patent/PT66956B/pt unknown
- 1977-08-25 AU AU28223/77A patent/AU510626B2/en not_active Expired
- 1977-08-25 NL NLAANVRAGE7709399,A patent/NL177831C/xx not_active IP Right Cessation
- 1977-08-26 PH PH20170A patent/PH15738A/en unknown
- 1977-08-26 FR FR7726082A patent/FR2362868A1/fr active Granted
- 1977-08-26 BE BE180469A patent/BE858156A/fr not_active IP Right Cessation
- 1977-08-26 CA CA285,572A patent/CA1115447A/fr not_active Expired
- 1977-08-26 DE DE19772738627 patent/DE2738627A1/de active Granted
- 1977-08-26 SE SE7709631A patent/SE438862B/xx not_active IP Right Cessation
- 1977-08-26 ES ES462114A patent/ES462114A1/es not_active Expired
- 1977-08-26 IT IT27002/77A patent/IT1084731B/it active

Also Published As

Publication number	Publication date
NO152753B (no)	1985-08-05
AT350258B (de)	1979-05-25
PH15738A (en)	1983-03-18
DE2738627C2 (fr)	1989-02-02
IT1084731B (it)	1985-05-28
NO152753C (no)	1985-11-13
JPS5327677A (en)	1978-03-15
NL177831C (nl)	1985-12-02
BR7705674A (pt)	1978-05-30
ZA775067B (en)	1978-07-26
ES462114A1 (es)	1978-12-01
JPS5812888B2 (ja)	1983-03-10
PT66956A (en)	1977-09-01
FR2362868A1 (fr)	1978-03-24
NO772897L (no)	1978-02-28
ATA613677A (de)	1978-10-15
PT66956B (en)	1979-02-08
SE7709631L (sv)	1978-02-28
FR2362868B1 (fr)	1980-10-17
NL7709399A (nl)	1978-03-01
AU510626B2 (en)	1980-07-03
DE2738627A1 (de)	1978-03-02
AU2822377A (en)	1979-03-01
SE438862B (sv)	1985-05-13
GB1564460A (en)	1980-04-10
BE858156A (fr)	1978-02-27

Legal Events

Date	Code	Title	Description
1998-12-29	MKEX	Expiry

Publication	Publication Date	Title
CA1085996A (fr)	1980-09-16	PROCEDE D'OBTENTION DE COPOLYMERES OU DE POLYMERES D'.alpha.-OLEFINES
EP0027386B1 (fr)	1984-03-07	Procédé de préparation d'une composition de résine de propylène et articles moulés à partir de cette composition
CA1280736C (fr)	1991-02-26	Polymerisation des olefines
US4168361A (en)	1979-09-18	Random copolymer of propylene and 1-butene and process for its production
CA1115447A (fr)	1981-12-29	Procede d'obtention de polymeres ou de copolymeres d'olefines
CA1089600A (fr)	1980-11-11	Obtention de polymeres ou de copolymeres d'olefines contenant au moins trois atomes de carbone
US4981930A (en)	1991-01-01	Method of production of polyolefins
CA1221954A (fr)	1987-05-19	Polymerisation d'olefines
NO153609B (no)	1986-01-13	Polymerisasjonskatalysator.
US4404342A (en)	1983-09-13	Process for preparing a copolymer
CA1255830A (fr)	1989-06-13	Preparation de copolymeres a sequence de propylene
CA1278290C (fr)	1990-12-27	Production d'un adjuvant de catalyse pour la polymerisation des olefines
CA1243657A (fr)	1988-10-25	Constituant catalytique pour la polymerisation des olefines
CA1201425A (fr)	1986-03-04	Methode et agent de catalyse pour la production d'un polymere au copolymere d'orefine
US4798866A (en)	1989-01-17	Branched alpha-olefin polymer composition and process for its production
CA1140523A (fr)	1983-02-01	ELEMENT DE CATALYSEUR DE LA POLYMERISATION DES .alpha.-OLEFINES
CA1168400A (fr)	1984-05-29	Methode de production de polyolefines
GB1576642A (en)	1980-10-15	Process and catalyst for polymerisation of alpha-olefins
GB2133020A (en)	1984-07-18	Polymerising olefins with an improved Ziegler catalyst
EP0565173B1 (fr)	1997-06-04	Procédé de préparation de polyoléfines à large distribution de poids moléculaire
CA1248694A (fr)	1989-01-10	Methode de preparation de poly(butene-1)
CA1199317A (fr)	1986-01-14	Methode de preparation d'un constituant catalytique a base de titane; polymerisation de 1-alcenes a l'aide de ce constituant
EP0294767A1 (fr)	1988-12-14	Procédé de production de polybutène-1
JP2514974B2 (ja)	1996-07-10	分枝α―オレフィン系重合体の製造方法
KR820001309B1 (ko)	1982-07-21	올레핀 중합체 또는 공중합체의 제조방법