IL93146A - Process for the preparation of 1,1,3,4,4,6-millet-1,2,3,4-tetrahydronaphthalene - Google Patents

Process for the preparation of 1,1,3,4,4,6-millet-1,2,3,4-tetrahydronaphthalene

Info

Publication number: IL93146A
Authority: IL; Israel
Prior art keywords: aluminum; butene; dimethyl; hmt; halide
Prior art date: 1989-01-27

Application number

IL9314690A

Other languages

English (en)

Hebrew (he)

Other versions

IL93146A0 (en

Original Assignee

Union Camp Corp

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.)

1989-01-27

Filing date

1990-01-23

Publication date

1994-06-24

1990-01-23 Application filed by Union Camp Corp filed Critical Union Camp Corp

1990-11-05 Publication of IL93146A0 publication Critical patent/IL93146A0/xx

1994-06-24 Publication of IL93146A publication Critical patent/IL93146A/en

Links

238000004519 manufacturing process Methods 0.000 title description 13
JIVANURAWUCQIG-UHFFFAOYSA-N 1,1,2,4,4,7-hexamethyl-2,3-dihydronaphthalene Chemical compound C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 JIVANURAWUCQIG-UHFFFAOYSA-N 0.000 title description 3
238000000034 method Methods 0.000 claims description 47
-1 aluminum halide Chemical class 0.000 claims description 39
239000002904 solvent Substances 0.000 claims description 31
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 26
PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 25
229910052782 aluminium Inorganic materials 0.000 claims description 21
OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 14
239000003153 chemical reaction reagent Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 6
150000001336 alkenes Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 claims description 3
OLVFZFJWXJHZMG-UHFFFAOYSA-K bromo(dichloro)alumane Chemical compound Cl[Al](Cl)Br OLVFZFJWXJHZMG-UHFFFAOYSA-K 0.000 claims description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
JNGNDYHADNWZFG-UHFFFAOYSA-K aluminum;dichloride;fluoride Chemical compound F[Al](Cl)Cl JNGNDYHADNWZFG-UHFFFAOYSA-K 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
OCBVBXBTFDQWLA-UHFFFAOYSA-K dichloro(iodo)alumane Chemical compound Cl[Al](Cl)I OCBVBXBTFDQWLA-UHFFFAOYSA-K 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000402754 Erythranthe moschata Species 0.000 description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 4
125000002723 alicyclic group Chemical group 0.000 description 4
239000003205 fragrance Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002468 indanes Chemical class 0.000 description 3
239000002304 perfume Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000005377 tertiary alkyl halides Chemical class 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
150000001717 carbocyclic compounds Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
IFQJNSKRPGNJJB-UHFFFAOYSA-K dibromo(fluoro)alumane Chemical compound F[Al](Br)Br IFQJNSKRPGNJJB-UHFFFAOYSA-K 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
238000010791 quenching Methods 0.000 description 2
230000000171 quenching effect Effects 0.000 description 2
238000010189 synthetic method Methods 0.000 description 2
UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
PMJHCUHTUTVMDB-UHFFFAOYSA-N 1,1,2,3,3,5-hexamethyl-2h-indene Chemical compound C1=C(C)C=C2C(C)(C)C(C)C(C)(C)C2=C1 PMJHCUHTUTVMDB-UHFFFAOYSA-N 0.000 description 1
NNXHDILUOAXSPU-UHFFFAOYSA-N 1,1,3,3,5-pentamethyl-2h-indene Chemical compound CC1=CC=C2C(C)(C)CC(C)(C)C2=C1 NNXHDILUOAXSPU-UHFFFAOYSA-N 0.000 description 1
LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
RCAHBLROJAUMKX-UHFFFAOYSA-N 1,3,3,6,6-pentamethyl-2,7-dihydro-1h-indene Chemical compound C1C(C)(C)C=CC2=C1C(C)CC2(C)C RCAHBLROJAUMKX-UHFFFAOYSA-N 0.000 description 1
SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 1
QEHNNAQSHBJMTJ-UHFFFAOYSA-N 2,2,3,3,4,4-hexamethyl-1h-naphthalene Chemical class C1=CC=C2C(C)(C)C(C)(C)C(C)(C)CC2=C1 QEHNNAQSHBJMTJ-UHFFFAOYSA-N 0.000 description 1
NPNLTHPVLNUJEV-UHFFFAOYSA-N 2,2,4,4-tetramethylpentan-3-ylbenzene Chemical compound CC(C)(C)C(C(C)(C)C)C1=CC=CC=C1 NPNLTHPVLNUJEV-UHFFFAOYSA-N 0.000 description 1
LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 description 1
JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010813 internal standard method Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000010327 methods by industry Methods 0.000 description 1
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000003578 releasing effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000005376 secondary alkyl halides Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/72—Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL9314690A 1989-01-27 1990-01-23 Process for the preparation of 1,1,3,4,4,6-millet-1,2,3,4-tetrahydronaphthalene IL93146A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/303,356 US4877912A (en)	1989-01-27	1989-01-27	Process for preparing 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene

Publications (2)

Publication Number	Publication Date
IL93146A0 IL93146A0 (en)	1990-11-05
IL93146A true IL93146A (en)	1994-06-24

Family

ID=23171715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9314690A IL93146A (en)	1989-01-27	1990-01-23	Process for the preparation of 1,1,3,4,4,6-millet-1,2,3,4-tetrahydronaphthalene

Country Status (8)

Country	Link
US (1)	US4877912A (ja)
EP (1)	EP0380288B1 (ja)
JP (1)	JPH02247131A (ja)
CA (1)	CA2008366A1 (ja)
DE (1)	DE69007637T2 (ja)
DK (1)	DK0380288T3 (ja)
ES (1)	ES2062323T3 (ja)
IL (1)	IL93146A (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1989
- 1989-01-27 US US07/303,356 patent/US4877912A/en not_active Expired - Fee Related
1990
- 1990-01-23 DE DE69007637T patent/DE69007637T2/de not_active Expired - Fee Related
- 1990-01-23 CA CA002008366A patent/CA2008366A1/en not_active Abandoned
- 1990-01-23 IL IL9314690A patent/IL93146A/en not_active IP Right Cessation
- 1990-01-23 ES ES90300679T patent/ES2062323T3/es not_active Expired - Lifetime
- 1990-01-23 DK DK90300679.9T patent/DK0380288T3/da active
- 1990-01-23 EP EP90300679A patent/EP0380288B1/en not_active Expired - Lifetime
- 1990-01-29 JP JP2016293A patent/JPH02247131A/ja active Pending

Also Published As

Publication number	Publication date
JPH02247131A (ja)	1990-10-02
ES2062323T3 (es)	1994-12-16
EP0380288A1 (en)	1990-08-01
EP0380288B1 (en)	1994-03-30
DE69007637D1 (de)	1994-05-05
US4877912A (en)	1989-10-31
CA2008366A1 (en)	1990-07-27
DE69007637T2 (de)	1994-07-14
DK0380288T3 (da)	1994-08-08
IL93146A0 (en)	1990-11-05

Legal Events

Date	Code	Title	Description
1996-10-31	RH	Patent void

Publication	Publication Date	Title
US4551573A (en)	1985-11-05	Alkylation of aromatic compounds
US3856875A (en)	1974-12-24	Process for producing 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronapthalene (hmt)
US4284818A (en)	1981-08-18	Process for preparing hexamethyltetrahydronaphthalenes
US3246044A (en)	1966-04-12	Process for making 1, 1, 3, 4, 4, 6-hexamethyl-1, 2, 3, 4-tetrahydronaphthalene
US4877912A (en)	1989-10-31	Process for preparing 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene
US4877915A (en)	1989-10-31	Process for preparing polyalkyl tetrahydronaphthalenes
US4877910A (en)	1989-10-31	Process for preparing polyalkyl tetrahydronaphthalenes
US4877911A (en)	1989-10-31	Process for preparing polyalkyl tetrahydronaphthalenes
US4877916A (en)	1989-10-31	Process for preparing polyalkyl tetrahydronaphthalenes
EP0554942B1 (en)	1996-05-22	Process for the preparation of linear alkylbenzenes
US4877913A (en)	1989-10-31	Process for preparing polyalkyl tetrahydronaphthalenes
EP0487319B1 (en)	1995-03-22	Novel heptamethyl indane compound
US3649698A (en)	1972-03-14	Preparation of haloabkanes
US4877914A (en)	1989-10-31	Process for preparing polyalkyl tetrahydronaphthalenes
EP0393742B1 (en)	1994-11-30	Process for the preparation of alkyl substituted tetralins and indanes
EP0594225B1 (en)	1997-09-17	Process for preparing polyalkyl tetrahydronaphtalenes
EP0381353B1 (en)	1994-12-07	Process for preparing polyalkyl tetrahydronaphthalenes
US2759030A (en)	1956-08-14	Preparation of mono-alkylated aromatic compounds
US2901517A (en)	1959-08-25	Preparation of substituted ortho-polymethylene aromatic hydrocarbons
Schmerling et al.	1958	Condensation of Benzene with Unsaturated Chlorides1
US2487986A (en)	1949-11-15	Reaction of bicyclo-olefins with alkyl halides
US4668835A (en)	1987-05-26	Novel tetracyclic trienes
JP2569155B2 (ja)	1997-01-08	アルキルアダマンタンの製造方法
US2436058A (en)	1948-02-17	Production of alkyl cycloalkyl halides
US3394196A (en)	1968-07-23	Aromatic hydrocarbon alkylation process