FI71925B - Foerfarande foer omvandling av terpener - Google Patents
Foerfarande foer omvandling av terpener Download PDFInfo
- Publication number
- FI71925B FI71925B FI830963A FI830963A FI71925B FI 71925 B FI71925 B FI 71925B FI 830963 A FI830963 A FI 830963A FI 830963 A FI830963 A FI 830963A FI 71925 B FI71925 B FI 71925B
- Authority
- FI
- Finland
- Prior art keywords
- terpenes
- terpene
- catalyst
- mono
- alkali metal
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 claims description 50
- 235000007586 terpenes Nutrition 0.000 claims description 45
- 150000003505 terpenes Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 37
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 5
- 150000002932 p-cymene derivatives Chemical class 0.000 claims description 5
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical class CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229930007927 cymene Natural products 0.000 claims description 4
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- 235000001510 limonene Nutrition 0.000 claims description 3
- 229940087305 limonene Drugs 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229930004008 p-menthane Natural products 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 229930006978 terpinene Natural products 0.000 claims description 2
- 150000003507 terpinene derivatives Chemical class 0.000 claims description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 1
- CZUZGUCIXCUKSC-UHFFFAOYSA-N 1-methyl-2-prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1C CZUZGUCIXCUKSC-UHFFFAOYSA-N 0.000 claims 1
- 239000004408 titanium dioxide Substances 0.000 claims 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 18
- 239000001739 pinus spp. Substances 0.000 description 18
- 229940036248 turpentine Drugs 0.000 description 18
- 239000013256 coordination polymer Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 241000894007 species Species 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- WWRCMNKATXZARA-UHFFFAOYSA-N 1-Isopropyl-2-methylbenzene Chemical compound CC(C)C1=CC=CC=C1C WWRCMNKATXZARA-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical class CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 101100279436 Caenorhabditis elegans egg-2 gene Proteins 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000218631 Coniferophyta Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
- XCYJPXQACVEIOS-UHFFFAOYSA-N 1-isopropyl-3-methylbenzene Chemical compound CC(C)C1=CC=CC(C)=C1 XCYJPXQACVEIOS-UHFFFAOYSA-N 0.000 description 1
- VEOUJEMZPSSLID-UHFFFAOYSA-N 1-methyl-2-propan-2-ylbenzene 1-methyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C)C=C1.CC(C)C1=CC=CC=C1C VEOUJEMZPSSLID-UHFFFAOYSA-N 0.000 description 1
- XFEGRFIENDJTCK-UHFFFAOYSA-N 2-phenyl-2,3-dihydroindene-1,1-dicarboxylic acid Chemical class C1C2=CC=CC=C2C(C(=O)O)(C(O)=O)C1C1=CC=CC=C1 XFEGRFIENDJTCK-UHFFFAOYSA-N 0.000 description 1
- 101001124623 Burkholderia pyrrocinia Non-heme chloroperoxidase Proteins 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000021559 Dicerandra Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 101000715514 Lactiplantibacillus plantarum (strain ATCC BAA-793 / NCIMB 8826 / WCFS1) Carbamoyl-phosphate synthase pyrimidine-specific small chain Proteins 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 1
- RTYZCUMXOXNVSI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOO RTYZCUMXOXNVSI-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-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
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 101001009851 Rattus norvegicus Guanylate cyclase 2G Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical compound [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 125000000567 diterpene group Chemical group 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002937 p-menthane derivatives Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- -1 terpene hydrocarbons Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/367—Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (10)
1. Förfarande för omvandling av terpener tili - metylmetylstyrener, kännetecknat därav, att 5 ätminstone en terpen, som är en mono- eller bicyklisk,omät-tad kolväte med formeln bringas i beröring med en alkalimetallhydroxidkatalysator pä ett underlag vid en tem-peratur av 300-500°C.
2. Förfarande enligt patentkravet 1, k ä n n e -10 tecknat därav, att terpenen är ^ -pinen, |?) - pinen, limonen, p-mentan (cis- eller trans-isomer), terpinolen, terpinen, mentadien eller Δ-3-karen.
3. Förfarande enligt patentkravet 1 för omvandling av terpener tili -metylmetylstyrener, känneteck-15 n a t därav, att ätminstone en terpen, som är en mono- eller bicyklisk, omättad kolväte med formeln bringas i beröring med en alkalimetallhydroxidkatalysator pä ett un-derlag som har en ytarea av ätminstone 10 m /g, vid en tem-peratur av 300-475°C. 20
4. Förfarande enligt patentkravet 3, känne tecknat därav, att alkalimetallhydroxiden är NaOH, LiOH eller KOH.
5. Förfarande enligt patentkravet 3, kännetecknat därav, att alkalimetallhydroxidkatalysatorn 25 uppbärs pä ett underlag, som är kiseldioxid, aluminiumoxid, magnesiumoxid, koi eller titandioxid.
6. Förfarande enligt patentkravet 1 för omvandling av terpener tili oO -metylmetylstyrener, kännetecknat därav, att ätminstone en terpen, som är en mono-30 eller bicyklisk, omättad kolväte med formeln ciqH16' bringas i beröring med en alkalimetallhydroxidkatalysator pä ett underlag, vid en temperatur av 300-500°C, varvid förhällandet mellan den genom katalysatorn per timme strömmande vätske-volymen och katalysatorns totala volym (liquid hour space 35 velocity, LHSV) är 0,20-20.
7. Förfarande enligt patentkravet 1 för omvandling av terpener till oO -metylmetylstyrener, känneteck-
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36569582 | 1982-04-05 | ||
| US06/365,695 US4375572A (en) | 1982-04-05 | 1982-04-05 | Process for the conversion of terpenes |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI830963A0 FI830963A0 (fi) | 1983-03-22 |
| FI830963L FI830963L (fi) | 1983-10-06 |
| FI71925B true FI71925B (fi) | 1986-11-28 |
| FI71925C FI71925C (sv) | 1987-03-09 |
Family
ID=23439943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI830963A FI71925C (sv) | 1982-04-05 | 1983-03-22 | Förfarande för omvandling av terpener. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4375572A (sv) |
| EP (1) | EP0094333B1 (sv) |
| JP (1) | JPS58185529A (sv) |
| CA (1) | CA1199339A (sv) |
| DE (1) | DE3361533D1 (sv) |
| DK (1) | DK148883A (sv) |
| FI (1) | FI71925C (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0522839A3 (en) * | 1991-07-11 | 1993-08-04 | Union Camp Corporation | Catalytic dehydrogenation of cyclic dienes |
| FI20095767L (sv) | 2009-07-07 | 2011-01-08 | Upm Kymmene Corp | Förfarande och anordning för konvertering av terpentin till bensinkomponenter |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE625994C (de) * | 1931-11-17 | 1936-02-19 | Hilding Olof Vidar Bergstroem | Verfahren zur Herstellung von Cymol und gegebenenfalls Toluol aus Terpenen oder terpenhaltigen Stoffen |
| US2376308A (en) * | 1943-01-09 | 1945-05-15 | American Cyanamid Co | p-cymene from monocyclic terpenes |
| US2376310A (en) * | 1943-06-23 | 1945-05-15 | American Cyanamid Co | Dimethyl styrene from monocyclic terpenes |
| US2387836A (en) * | 1943-06-23 | 1945-10-30 | American Cyanamid Co | 4-methyl-alpha-methyl styrene from bicyclic terpenes |
| US2745887A (en) * | 1953-06-15 | 1956-05-15 | Universal Oil Prod Co | Dehydrogenation of non-aromatic cyclic compounds |
| SU759498A1 (ru) * | 1977-07-08 | 1980-08-30 | Sergej A Polyakov | Способ получения стирола или его алкилпроизводных .1 |
| US4151071A (en) * | 1977-07-26 | 1979-04-24 | Phillips Petroleum Company | Dehydrocyclization process |
| US4367358A (en) * | 1981-12-14 | 1983-01-04 | The Goodyear Tire & Rubber Company | Method for the production of ethylbenzene |
-
1982
- 1982-04-05 US US06/365,695 patent/US4375572A/en not_active Expired - Lifetime
-
1983
- 1983-03-22 CA CA000424140A patent/CA1199339A/en not_active Expired
- 1983-03-22 FI FI830963A patent/FI71925C/sv not_active IP Right Cessation
- 1983-03-30 DK DK148883A patent/DK148883A/da not_active IP Right Cessation
- 1983-04-05 JP JP58059877A patent/JPS58185529A/ja active Pending
- 1983-04-05 EP EP83630054A patent/EP0094333B1/en not_active Expired
- 1983-04-05 DE DE8383630054T patent/DE3361533D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0094333A1 (en) | 1983-11-16 |
| DK148883A (da) | 1983-10-06 |
| DE3361533D1 (en) | 1986-01-30 |
| FI830963L (fi) | 1983-10-06 |
| FI71925C (sv) | 1987-03-09 |
| FI830963A0 (fi) | 1983-03-22 |
| DK148883D0 (da) | 1983-03-30 |
| US4375572A (en) | 1983-03-01 |
| CA1199339A (en) | 1986-01-14 |
| EP0094333B1 (en) | 1985-12-18 |
| JPS58185529A (ja) | 1983-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: THE GOODYEAR TIRE & RUBBER COMPANY |