FI106117B - Menetelmä syklisten monomeerien valmistamiseksi - Google Patents

Menetelmä syklisten monomeerien valmistamiseksi Download PDF

Info

Publication number: FI106117B
Authority: FI; Finland
Prior art keywords: polymer; catalyst; process according; terpene; chloride
Prior art date: 1998-02-06

Application number

FI980268A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI980268A0 (fi

FI980268L (fi

Inventor

Christer Bergstroem

Juhana Ruotoistenmaeki

Arto Moelsae

Original Assignee

Optatech Oy

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.)

1998-02-06

Filing date

1998-02-06

Publication date

2000-11-30

1998-02-06 Application filed by Optatech Oy filed Critical Optatech Oy

1998-02-06 Publication of FI980268A0 publication Critical patent/FI980268A0/fi

1998-02-06 Priority to FI980268A priority Critical patent/FI106117B/fi

1999-02-05 Priority to AU22817/99A priority patent/AU2281799A/en

1999-02-05 Priority to KR1020007008483A priority patent/KR20010040614A/ko

1999-02-05 Priority to JP2000530482A priority patent/JP2002502888A/ja

1999-02-05 Priority to EP99902573A priority patent/EP1051375A1/fr

1999-02-05 Priority to CN99802738A priority patent/CN1290242A/zh

1999-02-05 Priority to US09/601,647 priority patent/US6566570B1/en

1999-02-05 Priority to PCT/FI1999/000084 priority patent/WO1999040050A1/fr

1999-08-07 Publication of FI980268L publication Critical patent/FI980268L/fi

2000-11-30 Application granted granted Critical

2000-11-30 Publication of FI106117B publication Critical patent/FI106117B/fi

Links

238000000034 method Methods 0.000 title claims description 20
230000008569 process Effects 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 4
239000000178 monomer Substances 0.000 title description 18
125000004122 cyclic group Chemical group 0.000 title description 11
229920000642 polymer Polymers 0.000 claims description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 20
-1 cyclic olefin Chemical class 0.000 claims description 16
XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 13
238000003379 elimination reaction Methods 0.000 claims description 13
150000003505 terpenes Chemical class 0.000 claims description 13
CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
230000009477 glass transition Effects 0.000 claims description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 10
235000007586 terpenes Nutrition 0.000 claims description 10
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
239000005977 Ethylene Substances 0.000 claims description 9
241000779819 Syncarpia glomulifera Species 0.000 claims description 8
239000001739 pinus spp. Substances 0.000 claims description 8
229940036248 turpentine Drugs 0.000 claims description 8
WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims description 7
WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims description 7
238000005698 Diels-Alder reaction Methods 0.000 claims description 7
WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims description 7
229930006722 beta-pinene Natural products 0.000 claims description 7
230000008030 elimination Effects 0.000 claims description 7
LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 claims description 6
229930006739 camphene Natural products 0.000 claims description 6
ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 claims description 6
229920001577 copolymer Polymers 0.000 claims description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
150000001923 cyclic compounds Chemical class 0.000 claims description 3
238000000465 moulding Methods 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
239000011954 Ziegler–Natta catalyst Substances 0.000 claims description 2
238000012644 addition polymerization Methods 0.000 claims description 2
238000000071 blow moulding Methods 0.000 claims description 2
238000007033 dehydrochlorination reaction Methods 0.000 claims description 2
238000001125 extrusion Methods 0.000 claims description 2
238000001746 injection moulding Methods 0.000 claims description 2
239000012968 metallocene catalyst Substances 0.000 claims description 2
238000005649 metathesis reaction Methods 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
238000007151 ring opening polymerisation reaction Methods 0.000 claims description 2
238000003856 thermoforming Methods 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229920001169 thermoplastic Polymers 0.000 claims 1
239000004416 thermosoftening plastic Substances 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 13
238000007792 addition Methods 0.000 description 12
239000007795 chemical reaction product Substances 0.000 description 12
GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 10
238000007334 copolymerization reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000000605 extraction Methods 0.000 description 7
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
230000008901 benefit Effects 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
239000004713 Cyclic olefin copolymer Substances 0.000 description 5
MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 5
GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 5
239000002994 raw material Substances 0.000 description 5
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
229920001971 elastomer Polymers 0.000 description 4
229920000636 poly(norbornene) polymer Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
238000004618 QSPR study Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000000302 molecular modelling Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
101150059062 apln gene Proteins 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
229930006737 car-3-ene Natural products 0.000 description 1
BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000012967 coordination catalyst Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000007038 hydrochlorination reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
235000001510 limonene Nutrition 0.000 description 1
229940087305 limonene Drugs 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000010128 melt processing Methods 0.000 description 1
238000012900 molecular simulation Methods 0.000 description 1
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920003245 polyoctenamer Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
- C07C13/68—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings with a bridged ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
- C07C13/42—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure
- 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
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI980268A 1998-02-06 1998-02-06 Menetelmä syklisten monomeerien valmistamiseksi FI106117B (fi)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
FI980268A FI106117B (fi)	1998-02-06	1998-02-06	Menetelmä syklisten monomeerien valmistamiseksi
EP99902573A EP1051375A1 (fr)	1998-02-06	1999-02-05	Procede de preparation de monomeres cycliques
KR1020007008483A KR20010040614A (ko)	1998-02-06	1999-02-05	고리형 단량체를 제조하는 방법
JP2000530482A JP2002502888A (ja)	1998-02-06	1999-02-05	環状モノマーの製造方法
AU22817/99A AU2281799A (en)	1998-02-06	1999-02-05	Process for preparing cyclic monomers
CN99802738A CN1290242A (zh)	1998-02-06	1999-02-05	制备环状单体的方法
US09/601,647 US6566570B1 (en)	1998-02-06	1999-02-05	Process for preparing cyclic monomers
PCT/FI1999/000084 WO1999040050A1 (fr)	1998-02-06	1999-02-05	Procede de preparation de monomeres cycliques

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI980268A FI106117B (fi)	1998-02-06	1998-02-06	Menetelmä syklisten monomeerien valmistamiseksi
FI980268		1998-02-06

Publications (3)

Publication Number	Publication Date
FI980268A0 FI980268A0 (fi)	1998-02-06
FI980268L FI980268L (fi)	1999-08-07
FI106117B true FI106117B (fi)	2000-11-30

Family

ID=8550733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI980268A FI106117B (fi)	1998-02-06	1998-02-06	Menetelmä syklisten monomeerien valmistamiseksi

Country Status (8)

Country	Link
US (1)	US6566570B1 (fr)
EP (1)	EP1051375A1 (fr)
JP (1)	JP2002502888A (fr)
KR (1)	KR20010040614A (fr)
CN (1)	CN1290242A (fr)
AU (1)	AU2281799A (fr)
FI (1)	FI106117B (fr)
WO (1)	WO1999040050A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100784484B1 (ko) *	2005-11-30	2007-12-11	주식회사 엘지화학	고리형 올레핀 화합물의 증류 잔류물을 이용한 고리형올레핀 화합물의 제조 방법
US8227651B1 (en) *	2009-08-31	2012-07-24	The United States Of America As Represented By The Secretary Of The Navy	High density renewable fuels based on the selective dimerization of pinenes
US8975463B1 (en)	2009-08-31	2015-03-10	The United States Of America As Represented By The Secretary Of The Navy	Efficient conversion of pure and mixed terpene feedstocks to high density fuels
CN101870635A (zh) *	2010-07-07	2010-10-27	南京林业大学	一种冰片二烯的制备方法
WO2013162566A1 (fr) *	2012-04-26	2013-10-31	The Government Of The United States Of America As Represented By The Secretary Of The Navy	Carburants renouvelables de densité élevée, basés sur la dimérisation sélective de pinènes
EP3741790A1 (fr) *	2019-05-20	2020-11-25	Evonik Operations GmbH	Polyamide à sous-structures de terpénoïdes cycliques

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2966527A (en) *	1956-10-09	1960-12-27	Universal Oil Prod Co	Preparation of bicycloalkadienes
GB1268973A (en) *	1969-09-03	1972-03-29	Ici Ltd	Polycyclic compounds and copolymers derived therefrom
US4136247A (en) *	1977-12-05	1979-01-23	The B. F. Goodrich Company	Ring-opened iso-propylnorbornene copolymers
CA1270950A (fr) *	1986-01-28	1990-06-26	Mitsui Chemicals, Incorporated	Structure de disque optique a couche d'air en sandwich

1998
- 1998-02-06 FI FI980268A patent/FI106117B/fi active
1999
- 1999-02-05 KR KR1020007008483A patent/KR20010040614A/ko not_active Withdrawn
- 1999-02-05 WO PCT/FI1999/000084 patent/WO1999040050A1/fr not_active Ceased
- 1999-02-05 US US09/601,647 patent/US6566570B1/en not_active Expired - Fee Related
- 1999-02-05 EP EP99902573A patent/EP1051375A1/fr not_active Ceased
- 1999-02-05 AU AU22817/99A patent/AU2281799A/en not_active Abandoned
- 1999-02-05 JP JP2000530482A patent/JP2002502888A/ja active Pending
- 1999-02-05 CN CN99802738A patent/CN1290242A/zh active Pending

Also Published As

Publication number	Publication date
FI980268A0 (fi)	1998-02-06
FI980268L (fi)	1999-08-07
AU2281799A (en)	1999-08-23
JP2002502888A (ja)	2002-01-29
CN1290242A (zh)	2001-04-04
EP1051375A1 (fr)	2000-11-15
KR20010040614A (ko)	2001-05-15
WO1999040050A1 (fr)	1999-08-12
US6566570B1 (en)	2003-05-20

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US3865797A (en)	1975-02-11	Process for the production of petroleum resins of varying softening points
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US3403139A (en)	1968-09-24	Unsaturated linear copolymers consisting of copolymerized units of an acyclic 1-olefin and a cycloolefin having five carbon atoms in the ring
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Mathers et al.	2011	Monoterpenes as polymerization solvents and monomers in polymer chemistry