JPS6134344B2 - - Google Patents
Info
- Publication number
- JPS6134344B2 JPS6134344B2 JP53073330A JP7333078A JPS6134344B2 JP S6134344 B2 JPS6134344 B2 JP S6134344B2 JP 53073330 A JP53073330 A JP 53073330A JP 7333078 A JP7333078 A JP 7333078A JP S6134344 B2 JPS6134344 B2 JP S6134344B2
- Authority
- JP
- Japan
- Prior art keywords
- acetate
- cyclohex
- ethane
- propionate
- butyrate
- 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
- -1 3-cyclohexenylmethylisobutyrate Chemical compound 0.000 claims description 74
- 235000019645 odor Nutrition 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000443 aerosol Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- UYBXBOOBIVAIJM-UHFFFAOYSA-N cyclohex-3-en-1-ylmethyl acetate Chemical compound CC(=O)OCC1CCC=CC1 UYBXBOOBIVAIJM-UHFFFAOYSA-N 0.000 claims description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 2
- QEAUORCZKIOKQZ-UHFFFAOYSA-N 3-(cyclohexen-1-yl)propanoic acid Chemical compound OC(=O)CCC1=CCCCC1 QEAUORCZKIOKQZ-UHFFFAOYSA-N 0.000 claims 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 1
- 229940090181 propyl acetate Drugs 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 239000003205 fragrance Substances 0.000 description 15
- 229940022663 acetate Drugs 0.000 description 13
- 238000009835 boiling Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 210000000056 organ Anatomy 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007818 Grignard reagent Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- VEIYJWQZNGASMA-UHFFFAOYSA-N cyclohex-3-en-1-ylmethanol Chemical compound OCC1CCC=CC1 VEIYJWQZNGASMA-UHFFFAOYSA-N 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000007959 natural flavoring substance Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- FXFRNQWBJLNJHC-UHFFFAOYSA-N 4-(cyclohexen-1-yl)butanoic acid Chemical compound OC(=O)CCCC1=CCCCC1 FXFRNQWBJLNJHC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- IIOLXIVFODJEDX-UHFFFAOYSA-N cyclohex-3-en-1-yl acetate Chemical compound CC(=O)OC1CCC=CC1 IIOLXIVFODJEDX-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- FTIUTTJEFHWCSA-UHFFFAOYSA-N (2,6,6-trimethylcyclohexen-1-yl)methyl acetate Chemical compound CC(=O)OCC1=C(C)CCCC1(C)C FTIUTTJEFHWCSA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 208000035985 Body Odor Diseases 0.000 description 2
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 235000001053 badasse Nutrition 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 235000017803 cinnamon Nutrition 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 2
- 244000056931 lavandin Species 0.000 description 2
- 235000009606 lavandin Nutrition 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 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
- 239000011368 organic material Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 238000010419 pet care Methods 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000008786 sensory perception of smell Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000009988 textile finishing Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- XEQWCJMGFRGWNX-UHFFFAOYSA-N (4-methylcyclohex-3-en-1-yl)methyl acetate Chemical compound CC(=O)OCC1CCC(C)=CC1 XEQWCJMGFRGWNX-UHFFFAOYSA-N 0.000 description 1
- SVRPFYLINXECNP-UHFFFAOYSA-N (4-propan-2-ylcyclohexen-1-yl)methyl acetate Chemical compound C(C)(=O)OCC1=CCC(CC1)C(C)C SVRPFYLINXECNP-UHFFFAOYSA-N 0.000 description 1
- MRIXAGHIOGSYJY-UHFFFAOYSA-N (6-methylcyclohex-3-en-1-yl)methyl acetate Chemical compound CC1CC=CCC1COC(C)=O MRIXAGHIOGSYJY-UHFFFAOYSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical class C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MVDPTWHTUYDLTL-UHFFFAOYSA-N 4-Methylphenyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC1=CC=C(C)C=C1 MVDPTWHTUYDLTL-UHFFFAOYSA-N 0.000 description 1
- OAFJAALOFJVHMK-UHFFFAOYSA-N 4-cyclohexyl-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)C1CCCCC1 OAFJAALOFJVHMK-UHFFFAOYSA-N 0.000 description 1
- CQDXMEWDEWRRIS-UHFFFAOYSA-N 4-prop-1-en-2-ylcyclohexene Chemical compound CC(=C)C1CCC=CC1 CQDXMEWDEWRRIS-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 1
- 244000165082 Lavanda vera Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000005135 Micromeria juliana Nutrition 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 240000002114 Satureja hortensis Species 0.000 description 1
- 235000007315 Satureja hortensis Nutrition 0.000 description 1
- 206010040904 Skin odour abnormal Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical group C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
- FWZUNOYOVVKUNF-UHFFFAOYSA-N allyl acetate Chemical compound CC(=O)OCC=C FWZUNOYOVVKUNF-UHFFFAOYSA-N 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940062909 amyl salicylate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- ZICOSWDVLGBUAZ-UHFFFAOYSA-N cyclohex-3-en-1-ylmethyl formate Chemical compound O=COCC1CCC=CC1 ZICOSWDVLGBUAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- NYNCZOLNVTXTTP-UHFFFAOYSA-N ethyl 2-(1,3-dioxoisoindol-2-yl)acetate Chemical compound C1=CC=C2C(=O)N(CC(=O)OCC)C(=O)C2=C1 NYNCZOLNVTXTTP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 229940095045 isopulegol Drugs 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
- XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical compound CC1=C(N(=O)=O)C(C)=C(N(=O)=O)C(C(C)(C)C)=C1N(=O)=O XMWRWTSZNLOZFN-UHFFFAOYSA-N 0.000 description 1
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MSOPZDSMYQRTCD-UHFFFAOYSA-N pent-3-enyl acetate Chemical compound CC=CCCOC(C)=O MSOPZDSMYQRTCD-UHFFFAOYSA-N 0.000 description 1
- KSGCXWBGCPXVPV-UHFFFAOYSA-N pent-3-enyl butanoate Chemical compound CCCC(=O)OCCC=CC KSGCXWBGCPXVPV-UHFFFAOYSA-N 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229940074386 skatole Drugs 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80820777A | 1977-06-20 | 1977-06-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS548726A JPS548726A (en) | 1979-01-23 |
| JPS6134344B2 true JPS6134344B2 (enrdf_load_stackoverflow) | 1986-08-07 |
Family
ID=25198171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7333078A Granted JPS548726A (en) | 1977-06-20 | 1978-06-19 | Deodorizing agent |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS548726A (enrdf_load_stackoverflow) |
| AU (1) | AU519459B2 (enrdf_load_stackoverflow) |
| BR (1) | BR7803884A (enrdf_load_stackoverflow) |
| CA (1) | CA1107201A (enrdf_load_stackoverflow) |
| DE (1) | DE2826841A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2395033A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2000967B (enrdf_load_stackoverflow) |
| IT (1) | IT1099558B (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287100A (en) | 1978-03-14 | 1981-09-01 | Fritzsche Dodge & Olcott Inc. | 1,2,3,6-Tetrahydrobenzyl alcohol esters and compositions containing the same |
| JPS6074896U (ja) * | 1983-10-31 | 1985-05-25 | トヨタ自動車株式会社 | 横パンチ付粉末成形装置 |
| DE3517106A1 (de) * | 1985-05-11 | 1986-11-13 | Basf Ag, 6700 Ludwigshafen | Cyclohexanderivate |
| US8012554B2 (en) | 2007-09-12 | 2011-09-06 | Pactiv Corporation | Bags having odor management capabilities |
| KR20190057446A (ko) | 2015-09-14 | 2019-05-28 | 에센릭스 코프. | 증기 응축액 특히 입김 응축액을 수집 및 분석하기 위한 장치 및 시스템 그리고 이 장치 및 시스템을 사용하는 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH616645A5 (enrdf_load_stackoverflow) * | 1975-11-17 | 1980-04-15 | Roure Bertrand Dupont Sa |
-
1978
- 1978-06-19 BR BR787803884A patent/BR7803884A/pt unknown
- 1978-06-19 GB GB7827329A patent/GB2000967B/en not_active Expired
- 1978-06-19 AU AU37239/78A patent/AU519459B2/en not_active Expired
- 1978-06-19 JP JP7333078A patent/JPS548726A/ja active Granted
- 1978-06-19 CA CA305,753A patent/CA1107201A/en not_active Expired
- 1978-06-19 IT IT24699/78A patent/IT1099558B/it active
- 1978-06-19 DE DE19782826841 patent/DE2826841A1/de not_active Ceased
- 1978-06-19 FR FR7818299A patent/FR2395033A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1099558B (it) | 1985-09-18 |
| DE2826841A1 (de) | 1978-12-21 |
| AU3723978A (en) | 1980-01-03 |
| FR2395033B1 (enrdf_load_stackoverflow) | 1984-10-26 |
| IT7824699A0 (it) | 1978-06-19 |
| GB2000967A (en) | 1979-01-24 |
| GB2000967B (en) | 1982-03-17 |
| FR2395033A1 (fr) | 1979-01-19 |
| CA1107201A (en) | 1981-08-18 |
| JPS548726A (en) | 1979-01-23 |
| BR7803884A (pt) | 1979-02-20 |
| AU519459B2 (en) | 1981-12-03 |
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