DE2420474C3 - - Google Patents
Info
- Publication number
- DE2420474C3 DE2420474C3 DE19742420474 DE2420474A DE2420474C3 DE 2420474 C3 DE2420474 C3 DE 2420474C3 DE 19742420474 DE19742420474 DE 19742420474 DE 2420474 A DE2420474 A DE 2420474A DE 2420474 C3 DE2420474 C3 DE 2420474C3
- Authority
- DE
- Germany
- Prior art keywords
- benzoin
- mol
- reaction
- ether
- thionyl chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 240000008975 Styrax benzoin Species 0.000 claims description 65
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 65
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 65
- 235000019382 gum benzoic Nutrition 0.000 claims description 65
- 229960002130 Benzoin Drugs 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 12
- -1 benzoin ethers Chemical class 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 62
- ISAOCJYIOMOJEB-UHFFFAOYSA-N Benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- WURBFLDFSFBTLW-UHFFFAOYSA-N Benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atoms Chemical group C* 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N cdcl3 Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000000875 corresponding Effects 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 3
- PYTHIEVNGSYRFO-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-phenylethanone Chemical compound ClC1=CC=CC=C1C(=O)CC1=CC=CC=C1 PYTHIEVNGSYRFO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N 1-Nonanol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-Butanol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-Chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- DBBSWURSQHDBEQ-UHFFFAOYSA-N 2-butan-2-yloxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC(C)CC)C(=O)C1=CC=CC=C1 DBBSWURSQHDBEQ-UHFFFAOYSA-N 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
- QCPOKPFKMYZWBC-UHFFFAOYSA-N 2-octoxy-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(OCCCCCCCC)C(=O)C1=CC=CC=C1 QCPOKPFKMYZWBC-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- KQWUSKTUKWCNJG-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)OC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCCCCCCCC)OC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1 KQWUSKTUKWCNJG-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 230000035683 MEAN RESIDENCE TIME Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 1
- CQDMETPQGYKYJG-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC(C)(C)C)C(=O)C1=CC=CC=C1 CQDMETPQGYKYJG-UHFFFAOYSA-N 0.000 description 1
- CIMHWOQDOOMOEV-UHFFFAOYSA-N 2-cyclohexyloxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1CCCCC1 CIMHWOQDOOMOEV-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- OGLUUQQUORMJHW-UHFFFAOYSA-N 2-nonoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCCCCCCC)C(=O)C1=CC=CC=C1 OGLUUQQUORMJHW-UHFFFAOYSA-N 0.000 description 1
- NUANGSLQWFBVEH-UHFFFAOYSA-N 4-butylcyclohexan-1-ol Chemical compound CCCCC1CCC(O)CC1 NUANGSLQWFBVEH-UHFFFAOYSA-N 0.000 description 1
- WCTKUENARPWTAY-UHFFFAOYSA-N AC1L9MSS Chemical class OS(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-N 0.000 description 1
- TXJRKODLUJOXQW-UHFFFAOYSA-N ClC(C)(C)OC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1 Chemical compound ClC(C)(C)OC(C(C1=CC=CC=C1)=O)C1=CC=CC=C1 TXJRKODLUJOXQW-UHFFFAOYSA-N 0.000 description 1
- 241000544061 Cuculus canorus Species 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- 210000000003 Hoof Anatomy 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N Methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N Tert-Butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 102100015844 UBXN11 Human genes 0.000 description 1
- 101710027909 UBXN11 Proteins 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742420474 DE2420474B2 (de) | 1974-04-27 | 1974-04-27 | Verfahren zur herstellung von benzoinaethern |
| GB1633975A GB1499006A (en) | 1974-04-27 | 1975-04-21 | Process for the production of benzoin ether |
| DK179975A DK179975A (da) | 1974-04-27 | 1975-04-24 | Benzoinethere samt deres fremstilling og anvendelse |
| SE7504772A SE7504772L (sv) | 1974-04-27 | 1975-04-24 | Sett att framstella bensoinetrar. |
| IT4928875A IT1035460B (it) | 1974-04-27 | 1975-04-24 | Procedimento per produrre eteri benzoinici |
| NL7504866A NL7504866A (nl) | 1974-04-27 | 1975-04-24 | Werkwijze voor het bereiden van benzoineethers. |
| CH533575A CH613180A5 (en) | 1974-04-27 | 1975-04-25 | Process for the preparation of benzoin ethers |
| JP4983075A JPS5835171B2 (ja) | 1974-04-27 | 1975-04-25 | ベンゾインエ−テルノセイゾウホウ |
| BE155766A BE828384A (fr) | 1974-04-27 | 1975-04-25 | Procede de preparation d'ethers de benzoines |
| FR7513111A FR2268780B1 (nl) | 1974-04-27 | 1975-04-25 | |
| DD18570575A DD119780A5 (nl) | 1974-04-27 | 1975-04-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742420474 DE2420474B2 (de) | 1974-04-27 | 1974-04-27 | Verfahren zur herstellung von benzoinaethern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2420474A1 DE2420474A1 (de) | 1975-10-30 |
| DE2420474B2 DE2420474B2 (de) | 1976-02-26 |
| DE2420474C3 true DE2420474C3 (nl) | 1976-10-07 |
Family
ID=5914141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742420474 Granted DE2420474B2 (de) | 1974-04-27 | 1974-04-27 | Verfahren zur herstellung von benzoinaethern |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5835171B2 (nl) |
| BE (1) | BE828384A (nl) |
| CH (1) | CH613180A5 (nl) |
| DD (1) | DD119780A5 (nl) |
| DE (1) | DE2420474B2 (nl) |
| DK (1) | DK179975A (nl) |
| FR (1) | FR2268780B1 (nl) |
| GB (1) | GB1499006A (nl) |
| IT (1) | IT1035460B (nl) |
| NL (1) | NL7504866A (nl) |
| SE (1) | SE7504772L (nl) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2514680A1 (de) * | 1975-04-04 | 1976-10-14 | Bayer Ag | Benzoin-tert.-butylaether |
| JPS549252A (en) * | 1977-06-17 | 1979-01-24 | Yoshitomi Pharmaceut Ind Ltd | Preparation of benzoin ethers |
| JPS5414949A (en) * | 1977-07-01 | 1979-02-03 | Yoshitomi Pharmaceut Ind Ltd | Preparation of benzoin ether |
| JPS5424860A (en) * | 1977-07-28 | 1979-02-24 | Yoshitomi Pharmaceut Ind Ltd | Preparation of benzoin ether |
| DE102014226196A1 (de) * | 2014-12-17 | 2016-06-23 | Henkel Ag & Co. Kgaa | Photolabile Duftstoffvorläuferverbindung |
| JP6319415B1 (ja) | 2016-12-19 | 2018-05-09 | 横浜ゴム株式会社 | ランフラットタイヤ |
| EP3865315B1 (en) | 2018-11-16 | 2023-10-04 | The Yokohama Rubber Co., Ltd. | Run-flat tire |
| JP7151627B2 (ja) | 2019-05-27 | 2022-10-12 | 横浜ゴム株式会社 | 空気入りタイヤ |
-
1974
- 1974-04-27 DE DE19742420474 patent/DE2420474B2/de active Granted
-
1975
- 1975-04-21 GB GB1633975A patent/GB1499006A/en not_active Expired
- 1975-04-24 NL NL7504866A patent/NL7504866A/nl not_active Application Discontinuation
- 1975-04-24 DK DK179975A patent/DK179975A/da unknown
- 1975-04-24 SE SE7504772A patent/SE7504772L/xx not_active Application Discontinuation
- 1975-04-24 IT IT4928875A patent/IT1035460B/it active
- 1975-04-25 JP JP4983075A patent/JPS5835171B2/ja not_active Expired
- 1975-04-25 CH CH533575A patent/CH613180A5/xx not_active IP Right Cessation
- 1975-04-25 DD DD18570575A patent/DD119780A5/xx unknown
- 1975-04-25 FR FR7513111A patent/FR2268780B1/fr not_active Expired
- 1975-04-25 BE BE155766A patent/BE828384A/xx not_active IP Right Cessation
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