US3709929A - 4-methyl-2-pentanol crotonate - Google Patents
4-methyl-2-pentanol crotonate Download PDFInfo
- Publication number
- US3709929A US3709929A US00074228A US3709929DA US3709929A US 3709929 A US3709929 A US 3709929A US 00074228 A US00074228 A US 00074228A US 3709929D A US3709929D A US 3709929DA US 3709929 A US3709929 A US 3709929A
- Authority
- US
- United States
- Prior art keywords
- methyl
- pentanol
- crotonate
- odor
- perfume
- 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 - Lifetime
Links
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 title abstract description 19
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 title abstract description 17
- 239000000203 mixture Substances 0.000 abstract description 22
- 239000003205 fragrance Substances 0.000 abstract description 13
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- 239000002304 perfume Substances 0.000 description 15
- 235000019645 odor Nutrition 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- -1 crotonic acid ester Chemical class 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 235000018219 lavender Nutrition 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- ZGPPERKMXSGYRK-UHFFFAOYSA-N Citronellyl isobutyrate Chemical compound CC(C)=CCCC(C)CCOC(=O)C(C)C ZGPPERKMXSGYRK-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 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
- 241000220225 Malus Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 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
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 239000001469 lavandula hydrida abrial herb oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
Definitions
- Subject of the invention is 4-methyl-2-pentanol crotonate, a process for its production whereby 4-methyl-2- pentanol is esterified with crotonic acid and the use of the crotonate for perfume compositions and as an odorant.
- This invention relates to the crotonic acid ester of 4-methyl-2-pentanol, to its preparation and to its application.
- the compound according to this invention can be obtained by esterification methods known per se, preferably by the direct esterification of crotonic acid with 4-methyl- 2-pentanol, the water of reaction formed preferably being removed azeotropically, in the presence of an acid catalyst, for example concentrated sulphuric acid or p-toluene sulphonic acid, and a hydrocarbon boiling at 80 to 150 C., preferably toluene or xylene, as entraining agents.
- an acid catalyst for example concentrated sulphuric acid or p-toluene sulphonic acid
- a hydrocarbon boiling at 80 to 150 C. preferably toluene or xylene
- the ester according to the invention is distinguished by desirable odoriferous properties and adds a valuable odorant to the perfume materials hitherto available for synthesizing fruit-like notes.
- odorants preferably used for the synthesis of fruitlike notes, such as iso-amyl acetate, hexyl acetate, ethyl acetate and other esters of lower fatty acids, readily bring to mind undesirable notions of bonbons or solvents or commercial products. For this reason they are not easy to handle in the composition of perfumes and have to be harmonically rounded off in terms of odor by skillfully combining several of these substances in order to restrict the occurrence of aesthetically unpleasant notes.
- 4-methyl-2-pentanol crotonate does not have any of these disadvantages. It has a very pleasant, pure fruit-like note reminiscent in particular of plum and apple preserves. It differs from conventional fruit-like odorants not only in its type of odor but also in the fact that it can be used more easily and more widely. Although distinct effects in the perfume composition can be obtained even with small quantities of the odorant, it can also be used in a high concentration in the composition or even without any other odorants for perfuming preparations by virtue of its aesthetically pleasing odor, without the aforementioned negative side etfects encountered in conventional fruity odorants.
- the compound according to the invention can be used for a very wide variety of applications. It is suitable for use in perfume compositions for numerous end products of the cosmetics, fine-perfumery, detergent and chemical specialities industries.
- compositions are further enriched by using 4-methyl-2-pentanol crotonate insofar as novel extremely harmonic odor accords can be obtained with this odorant, especially by combining it with flower and green odorants.
- EXAMPLE 1 The following formulation is given as an example of the preparation of a perfume with a plum-like odor which is a suitable fragrance for dishwashing detergents:
- a dishwashing detergent scented with this formulation can have the following composition for example:
- a skin cream perfumed with this composition can be prepared as follows for example:
- Phase A 50 g. of oleic acid decyl ester, 125 g. of glycerine monostearate (self-emulsifying), 50 g. of paraffinum per liquidum, 20 g. of cetaceum DAB 7, 1 g. of p-hydroxybenzoic acid propyl ester.
- Phase B 720 g. of distilled water, 1 g. of p-hydroxybenzoic acid methyl ester, 30 g. of sorbitol, 3 g. of perfume oil.
- Phase A and phase B are heated to 75 C., after which phase B is stirred into phase A, cooled with stirring to 40 C. and perfumed.
- EXAMPLE 3 The following formulation is given as an example of the preparation of a perfume with a lemon odor which is suitable for perfuming an insect spray:
- the fruit component is enhanced by the 4-methyl-2-pentanol crotonate, the odor is fuller and more pleasant.
- An insect spray. perfumed with this composition can be prepared as follows, for example:
- EXAMPLE 4 The following formulation is given as an example of the preparation of a lavender composition which is suitable for perfuming tissues:
- Difluorodichloromethane 12 The herb-like, lavandin oil note is sweetened by the 4-methyl-2-pentanol crotonate and displaced more towards the lavender type.
- Tissues perfumed with this composition can be produced by impregnating paper webbing with a solution which can have the following composition for example:
- reaction mixture is washed first with 2 litres of 10% soda solution to remove the acids and then with water until the reaction mixture reacts neutrally.
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)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
SUBJECTED OF THE INVENTION IS 4-METHYL-2-PENTANOL CROTONATE, A PROCESS FOR ITS PRODUCTION WHEREBY 4-METHYL-2PENTANOL IS ESTERIFIED WITH CROTONIC ACID AND THE USE OF THE CROTONATE FOR PERFUME COMPOSITIONS AND AS AN ODORANT.
Description
3,709,929 4-METHYL-2-PENTANOL CROTONATE Fritz Exner and Theodor Leidig, Holzminden, Germany, assignors to Haarmann & Reimer Gesellschaft mit beschrankter Haftung, Holzminden, Germany No Drawing. Filed Sept. 21, 1970, Ser. No. 74,228 Claims priority, application Germany, Apr. 10, 1970, P 20 17 208.1 Int. Cl. C07c 6'9/56 US. Cl. 260486 R 1 Claim ABSTRACT OF THE DISCLOSURE Subject of the invention is 4-methyl-2-pentanol crotonate, a process for its production whereby 4-methyl-2- pentanol is esterified with crotonic acid and the use of the crotonate for perfume compositions and as an odorant.
This invention relates to the crotonic acid ester of 4-methyl-2-pentanol, to its preparation and to its application.
The compound according to this invention can be obtained by esterification methods known per se, preferably by the direct esterification of crotonic acid with 4-methyl- 2-pentanol, the water of reaction formed preferably being removed azeotropically, in the presence of an acid catalyst, for example concentrated sulphuric acid or p-toluene sulphonic acid, and a hydrocarbon boiling at 80 to 150 C., preferably toluene or xylene, as entraining agents.
The ester according to the invention is distinguished by desirable odoriferous properties and adds a valuable odorant to the perfume materials hitherto available for synthesizing fruit-like notes.
For some years now, the fruit-like note, partly dominating, partly as a nuance of an odor complex, has been acquiring increasing significance in the manufacture of perfumes for general use and in the synthesis of certain types of odor in fine erfumery. This may be attributable to the fact that an awareness of culinary odors is associated more or less unconsciously with a feeling of Wellbeing.
The odorants preferably used for the synthesis of fruitlike notes, such as iso-amyl acetate, hexyl acetate, ethyl acetate and other esters of lower fatty acids, readily bring to mind undesirable notions of bonbons or solvents or commercial products. For this reason they are not easy to handle in the composition of perfumes and have to be harmonically rounded off in terms of odor by skillfully combining several of these substances in order to restrict the occurrence of aesthetically unpleasant notes.
4-methyl-2-pentanol crotonate does not have any of these disadvantages. It has a very pleasant, pure fruit-like note reminiscent in particular of plum and apple preserves. It differs from conventional fruit-like odorants not only in its type of odor but also in the fact that it can be used more easily and more widely. Although distinct effects in the perfume composition can be obtained even with small quantities of the odorant, it can also be used in a high concentration in the composition or even without any other odorants for perfuming preparations by virtue of its aesthetically pleasing odor, without the aforementioned negative side etfects encountered in conventional fruity odorants.
By virtue of its type of odor and its service properties, the compound according to the invention can be used for a very wide variety of applications. It is suitable for use in perfume compositions for numerous end products of the cosmetics, fine-perfumery, detergent and chemical specialities industries.
In high concentrations it is preferably used for plum United States Patent 3,709,929 Patented Jan. 9, 1973 notes, in average concentrations as the main carrier of the fruit-like character in conjunction with other suitable odorants for the production of other fruit-like notes such as apple, pear, peach and grape. In low concentrations, 4-methy1-2-pentanol crotonate is advantageously also used in compositions where the dominating odor note cannot be regarded as fruit. In this way, a natural character can be imparted to some of these compositions.
The possibilities of composition are further enriched by using 4-methyl-2-pentanol crotonate insofar as novel extremely harmonic odor accords can be obtained with this odorant, especially by combining it with flower and green odorants.
EXAMPLE 1 The following formulation is given as an example of the preparation of a perfume with a plum-like odor which is a suitable fragrance for dishwashing detergents:
fi -hexanol isobutyrate, 10% 5 Bergramot oil, Reggio 1O Geraniol Geranyl acetate Citronellyl acetate 40 Citronellyl isobutyrate a 50 Citronellol 50 Phenylmethyl glycidic acid ethyl ester, 1% 5 Terpineol 20 Phenylethyl isobutyrate 50 4-methyl-2-pentanol crotonate 500 4-methyl-2-pentanol crotonate produces a pleasant fullfruit plum note without being found to be overdosed in this concentration as is often the case with conventional plum odorants.
A dishwashing detergent scented with this formulation can have the following composition for example:
Sodium alkyl sulphonate or sodium alkyl benzosulphonate 200 Fatty alcohol ether sulphate 70 Coconut fatty acid diethanolamide 30 Sodium chloride 20 Water, coloring and skin preservative 677 Perfume oil 3 EXAMPLE 2 The following formulation is given as an example of the preparation of a flower bouquet with a freshening fruit nuance which is suitable for perfuming creams:
The somewhat flat, harmless, phantasy bouquet is distinctly freshened and aesthetically improved by the small addition of 4-methyl-2-pentanol crotonate. The fruit nuance introduced gives the perfume more freshness and a natural character.
A skin cream perfumed with this composition can be prepared as follows for example:
Phase A: 50 g. of oleic acid decyl ester, 125 g. of glycerine monostearate (self-emulsifying), 50 g. of paraffinum per liquidum, 20 g. of cetaceum DAB 7, 1 g. of p-hydroxybenzoic acid propyl ester.
Phase B: 720 g. of distilled water, 1 g. of p-hydroxybenzoic acid methyl ester, 30 g. of sorbitol, 3 g. of perfume oil.
Phase A and phase B are heated to 75 C., after which phase B is stirred into phase A, cooled with stirring to 40 C. and perfumed.
EXAMPLE 3 The following formulation is given as an example of the preparation of a perfume with a lemon odor which is suitable for perfuming an insect spray:
In the lemon odor of the perfume, the fruit component is enhanced by the 4-methyl-2-pentanol crotonate, the odor is fuller and more pleasant.
An insect spray. perfumed with this composition can be prepared as follows, for example:
2,2-dichlorovinyl dimethyl phosphate 5 Epichlorohydrin 2 Isopropyl alcohol 40 Odorless kerosene 100 Perfume oil 3 Monofluorotrichloromethane 11 425 2,2-dichl0rovinyl dimethyl phosphate and epichlorohydrin are dissolved in isopropyl alcohol, odorless kerosene and perfume oil are added, the can is closed with a valve and, after pressure-filling, is filled with the propellent gas mixture 11/ 12 50:50.
EXAMPLE 4 The following formulation is given as an example of the preparation of a lavender composition which is suitable for perfuming tissues:
Difluorodichloromethane 12 The herb-like, lavandin oil note is sweetened by the 4-methyl-2-pentanol crotonate and displaced more towards the lavender type.
Tissues perfumed with this composition can be produced by impregnating paper webbing with a solution which can have the following composition for example:
Percent Alcohol Perfume oil 3 Distilled Water 17 EXAMPLE 5 A mixture of 6 mols=516 g. of crotonic acid, 5 mols =S60 g. of 4-methyl-2-pentanol, 20 g. of p-toluene sulphonic acid and 2 liters of xylene is heated under reflux in an apparatus provided with a water separator until no more water is separated (theoretical 90 g.).
In general this is achieved after 4 hours when cc. of the Water have been separated off.
The reaction mixture is washed first with 2 litres of 10% soda solution to remove the acids and then with water until the reaction mixture reacts neutrally.
After the xylene has been distilled off, the product is distilled in vacuo, giving at B.P. 80-85 C. 780 g. or 91.7% of the theoretical of crude crotonic acid 4-methyl- 2-pentanol ester.
The crude ester is re-washed with soda solution and water and then re-distilled. Yield 764 g.=89.5% of the theoretical.
B.P. 86-88 C.; D 0.875; 11 1.4324.
We claim: 1. 4-methyl-2-pentanol crotonate.
References Cited Kulka, K., Chemical Abstracts, vol. 58, 778111, 1963.
LORRAINE A. WEINB'ERGER, Primary Examiner P. J. KILLOS, Assistant Examiner U.S. Cl. X.R. 252522
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017208 DE2017208A1 (en) | 1970-04-10 | 1970-04-10 | 4-methyl pentanoI-2-crotonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3709929A true US3709929A (en) | 1973-01-09 |
Family
ID=5767702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00074228A Expired - Lifetime US3709929A (en) | 1970-04-10 | 1970-09-21 | 4-methyl-2-pentanol crotonate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3709929A (en) |
| CH (1) | CH550133A (en) |
| DE (1) | DE2017208A1 (en) |
| FR (1) | FR2089509A5 (en) |
| GB (1) | GB1279080A (en) |
| NL (1) | NL7014250A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5096532A (en) * | 1974-01-07 | 1975-07-31 | ||
| US4498996A (en) * | 1982-07-08 | 1985-02-12 | International Flavors & Fragrances Inc. | Use in augmenting or enhancing aroma of perfumed article with acyloxy alkanols and esters thereof |
| US8772533B1 (en) * | 2013-02-25 | 2014-07-08 | International Flavors & Fragrances Inc. | Organoleptic compound |
| US8785677B1 (en) * | 2013-02-25 | 2014-07-22 | International Flavors & Fragrances Inc. | Organoleptic compound |
| US10072233B2 (en) | 2015-01-23 | 2018-09-11 | P2 Science, Inc. | Fragrance and flavor compositions comprising neopentyl glycol diacetate |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2414332A1 (en) * | 1978-01-13 | 1979-08-10 | Unilever Nv | DEODORIZING ITEMS TO DISCARD AFTER USE |
| GB0313173D0 (en) | 2003-06-07 | 2003-07-16 | Givaudan Sa | Improvements in or related to organic compounds |
-
1970
- 1970-04-10 DE DE19702017208 patent/DE2017208A1/en active Pending
- 1970-09-21 US US00074228A patent/US3709929A/en not_active Expired - Lifetime
- 1970-09-28 NL NL7014250A patent/NL7014250A/xx unknown
-
1971
- 1971-03-26 CH CH446971A patent/CH550133A/en not_active IP Right Cessation
- 1971-04-09 FR FR7112797A patent/FR2089509A5/fr not_active Expired
- 1971-04-19 GB GB26162/71A patent/GB1279080A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5096532A (en) * | 1974-01-07 | 1975-07-31 | ||
| US4498996A (en) * | 1982-07-08 | 1985-02-12 | International Flavors & Fragrances Inc. | Use in augmenting or enhancing aroma of perfumed article with acyloxy alkanols and esters thereof |
| US8772533B1 (en) * | 2013-02-25 | 2014-07-08 | International Flavors & Fragrances Inc. | Organoleptic compound |
| US8785677B1 (en) * | 2013-02-25 | 2014-07-22 | International Flavors & Fragrances Inc. | Organoleptic compound |
| US10072233B2 (en) | 2015-01-23 | 2018-09-11 | P2 Science, Inc. | Fragrance and flavor compositions comprising neopentyl glycol diacetate |
Also Published As
| Publication number | Publication date |
|---|---|
| CH550133A (en) | 1974-06-14 |
| GB1279080A (en) | 1972-06-21 |
| FR2089509A5 (en) | 1972-01-07 |
| DE2017208A1 (en) | 1971-10-21 |
| NL7014250A (en) | 1971-10-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106715375A (en) | Use of novel cyclic carbaldeydes as an aromatic substance | |
| US3637533A (en) | Perfume-containing compositions containing certain oximes as olfactory agents | |
| EP0040894B1 (en) | Perfume compositions and perfumed articles containing esters of substituted bicyclo (2.2.1)heptane- and heptene-carboxylic acids as perfume base | |
| EP2177598A1 (en) | Isomers of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, ethyl ester and their use in perfume compositions | |
| AU667322B2 (en) | Process for the preparation of phenylaldehydes | |
| US3709929A (en) | 4-methyl-2-pentanol crotonate | |
| DE69512717T2 (en) | Cyclic diester and use thereof as a fragrance | |
| JPS5818056B2 (en) | Aromatic and/or flavor composition | |
| US3647847A (en) | Isolongifolene esters | |
| JP2022532827A (en) | (3aS, 4aR, 5S, 7aS, 9R, 9aR) -2,2,5,8,8,9a-Hexamethyloctahydro-4H-4a, 9-methanoazureno [5,6-d] [1,3] Dioxol | |
| EP2070512B1 (en) | Methyl cyclohexane carboxylates and their use in perfume compositons | |
| US4252728A (en) | Norbornane and norbornene derivatives | |
| JPH068432B2 (en) | Fragrance composition | |
| US4267075A (en) | Perfume compositions containing esters of 3,5,5-trimethylhexanoic acid | |
| US4519944A (en) | Spirolactones as odorants | |
| JP2023520023A (en) | (S,Z)-3,7-dimethylnon-6-en-1-ol and its use as a fragrance | |
| EP0581052A1 (en) | Use of tetrahydro-4-methyl-2-phenyl-2h-pyran as perfuming ingredient | |
| US4545930A (en) | Terpene derivatives and perfume compositions containing them | |
| US4144200A (en) | 3-Phenyl-cyclopent-2-en-1-one in perfume compositions | |
| EP1186590B1 (en) | Allyl ether and its use as a fragrance ingredient | |
| US5057239A (en) | Use of a spiranic lactone as fragrance ingredient | |
| US20080064624A1 (en) | Organoleptic Compounds and Their Use in Perfume Compositions | |
| US4661286A (en) | Oxaspirododecane derivatives and perfume compositions containing them | |
| US7838488B2 (en) | Propanol and related compounds and their use in perfume compositions | |
| SU1304817A1 (en) | Deodorant |