US3655735A - Production of 3-methylbut-2-en-1-ol or 3-methylbut-2-en-1-yl acetate - Google Patents
Production of 3-methylbut-2-en-1-ol or 3-methylbut-2-en-1-yl acetate Download PDFInfo
- Publication number
- US3655735A US3655735A US782420A US3655735DA US3655735A US 3655735 A US3655735 A US 3655735A US 782420 A US782420 A US 782420A US 3655735D A US3655735D A US 3655735DA US 3655735 A US3655735 A US 3655735A
- Authority
- US
- United States
- Prior art keywords
- methylbut
- acetate
- compounds
- production
- mixture
- 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
- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 title abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 title description 15
- OCUAPVNNQFAQSM-UHFFFAOYSA-N 3-Methyl-3-butenyl acetate Chemical compound CC(=C)CCOC(C)=O OCUAPVNNQFAQSM-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001728 carbonyl compounds Chemical class 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 230000000737 periodic effect Effects 0.000 abstract description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052742 iron Inorganic materials 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 7
- 238000006317 isomerization reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 150000007514 bases Chemical class 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- -1 3- methylbut-Z-en-l-yl acetate Chemical compound 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QVDTXNVYSHVCGW-ARJAWSKDSA-N (z)-3-methylbut-1-en-1-ol Chemical compound CC(C)\C=C/O QVDTXNVYSHVCGW-ARJAWSKDSA-N 0.000 description 1
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- JCXLZXJCZPKTBW-UHFFFAOYSA-N diiron nonacarbonyl Chemical group [Fe].[Fe].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] JCXLZXJCZPKTBW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000002266 vitamin A derivatives Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Definitions
- 3-methylbut-2-en-1-ol or 3- methylbut-Z-en-l-yl acetate can be obtained in a simple way and in high yields by treating 3-methylbut-3-en-1-ol or 3-methylbut-3-en-1-yl acetate with a catalytic amount of a carbonyl compound of a metal of subgroups 6 to 8 of the Periodic System.
- the starting compounds are known and obtainable particularly advantageously by reaction of isobutene with formaldehyde followed if necessary by acetylation.
- Suitable compounds which act as isomerization catalysts are particularly those of zerovalent metals in accordance with the definition, more particularly, complexes having one or two central atoms such as chromium hexacarbonyl, iron pentacarbonyl, diiron nonacarbonyl, and nickel tetracarbonyl.
- complexes having one or two central atoms such as chromium hexacarbonyl, iron pentacarbonyl, diiron nonacarbonyl, and nickel tetracarbonyl.
- Compounds in which some of the carbonyl groups have been replaced by other ligands, as in dihydrogen iron tetracarbonyl or hydrogen cobalt tetracarbonyl are also suitable.
- Suitable ligands in such compounds are those which bear basic nitrogen or phosphorus atoms.
- Examples of such carbonyl compounds are bistriphenylphosphine iron tricarbonyl and tripyridine diiron tetracarbonyl.
- Iron pentacarbonyl is particularly preferred as the catalyst.
- the amount of carbonyl compound required for the isomerization is from 0.01 to 20% by weight, preferably from 1 to by weight, with reference to the amount of starting material to be isomerized. It is possible however to use larger or smaller amounts of these catalysts, the isomerization merely being accelerated or retarded thereby.
- the reaction may be carried out at temperatures of from about 100 to 300 C., preferably from 150 to 200 C. at atmospheric pressure or at superatmospheric pressure up to about 50 atmospheres with or without a solvent and batchwise or continuously.
- Suitable basic compounds include, in addition to inorganic bases such as sodium hydroxide, barium hydroxide or ammonia and in addition to the salts of strong bases and weak acids such as sodium carbonate or ammonium carbonate, particularly nitrogenous basic compounds such as alkylamines or arylamines and also compounds which are capable of splitting ofl bases, such as piperidine acetate or acid amides such as acetamide or urea.
- Hexamethylenetetramine (urotropine) is preferred as the basic compound.
- the basic compound is generally used in an amount of from 0.01 to 20%, preferably from 1 to 10%, by weight with reference to the compound to be isomerized.
- Hydrocarbons which are liquid under the reaction conditions concerned, as for example hexane, heptane, ligroin, benzene, toluene or xylene, are especially suitable as solvents.
- high boiling point ether' such as diphenyl ether, 2,2'-dimethoxydiethyl ether and 2,2'-diet.hoxydiethyl ether are also suitable.
- reaction mixture When the isomerization is over, the reaction mixture may be worked up by conventional methods, preferably by distillation.
- the products of the process are valuable intermediates for organic synthesis, particularly for the production of compounds of the carotenoid and vitamin A series and of perfumes.
- EXAMPLE 1 A mixture of 50 g. of 3-methylbut-3-en-l-yl acetate and 3.5 g. of iron pentacarbonyl is heated for fifteen hours at 150 C. and the desired product (3-methylbut-2-en-1-yl, B.P. to 112 C. at 200 mm.) is isolated from the mixture in the usual way by fractional distillation. The yield of pure products is 86% at a conversion of 42%.
- EXAMPLE 3 A mixture of 1000 g. of 3-methylbut-3-en-1-ol, 10 g. of iron pentacarbonyl and 50 g. of urotropine is heated for ninety minutes at 200 C. and the desired product is isolated from this mixture in the usual way by fractional distillation.
- EXAMPLE 4 A mixture of g. of 3-methylbut-3-en-1-ol, 22 g. of iron pentacarbonyl and 9 g. of urotropine is heated for thirty minutes at 200 C. and B-methylbut-Z-en-l-ol is isolated in the usual way by fractional distillation. The yield of pure product is 89% at a conversion of 31%.
- EXAMPLE 5 A mixture of 1000 g. of 3-methylbut-3-en-1-ol, 15 g. of iron pentacarbonyl and 60 ml. of liquid ammonia is heated at 175 C. in an autoclave for two hours and the 3-methylbut-2-en-1-ol is then isolated by fractional distillation. The yield of pure product is 73% at a conversion of 40%.
- EXAMPLE 6 An isomerizing process for the production of 3-methylbut-Z-en-l-ol or 3-methylbut-2-en-1-y1 acetate which comprises treating 3-methylbut-3-en-1-ol or 3-methyl-3-enl-yl acetate at a temperature of about 100 C. to 300 C. with a catalytic amount of iron pentacarbonyl and in the presence of a catalytic amount of a basic reacting compound selected from the class consisting of sodium hydroxide, barium hydroxide, ammonia, sodium carbonate, ammonium carbonate, piperidine acetate, acetamide, urea, alkyl and aryl amines and phosphines.
- a basic reacting compound selected from the class consisting of sodium hydroxide, barium hydroxide, ammonia, sodium carbonate, ammonium carbonate, piperidine acetate, acetamide, urea, alkyl and aryl amines and phosphines.
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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0095759 | 1967-12-08 | ||
| DE19681768023 DE1768023C3 (de) | 1967-12-08 | 1968-03-22 | Verfahren zur Herstellung von 3-Methyl-2-buten-1-ol oder 3-Methyl-2-buten-1-ylacetat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3655735A true US3655735A (en) | 1972-04-11 |
Family
ID=25755486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US782420A Expired - Lifetime US3655735A (en) | 1967-12-08 | 1968-12-09 | Production of 3-methylbut-2-en-1-ol or 3-methylbut-2-en-1-yl acetate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3655735A (enrdf_load_stackoverflow) |
| BE (1) | BE725088A (enrdf_load_stackoverflow) |
| CH (1) | CH525173A (enrdf_load_stackoverflow) |
| DE (2) | DE1643709B1 (enrdf_load_stackoverflow) |
| FR (1) | FR1594968A (enrdf_load_stackoverflow) |
| GB (1) | GB1239434A (enrdf_load_stackoverflow) |
| NL (1) | NL167408C (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117016A (en) * | 1977-05-27 | 1978-09-26 | Phillips Petroleum Company | Process for structural modification of unsaturated alcohols |
| US4122291A (en) * | 1976-06-08 | 1978-10-24 | Kuraray Co., Ltd. | Method for the production of alken-2-ol-1 or of alken-2-ol-1 and alkanol-1 |
| US4387047A (en) * | 1980-02-13 | 1983-06-07 | Firmenich Sa | Esters of 1,3-dimethyl-but-3-en-1-yl, their utilization as perfuming and flavoring ingredients and compositions containing same |
| CN102701910A (zh) * | 2012-05-24 | 2012-10-03 | 南开大学 | 一种通过异构化3-甲基-3-丁烯-1-醇制备异戊烯醇的方法 |
| CN104994949A (zh) * | 2013-01-23 | 2015-10-21 | 弗门尼舍有限公司 | 制备4-甲基戊-3-烯-1-醇衍生物的方法 |
| CN107141197A (zh) * | 2017-06-23 | 2017-09-08 | 万华化学集团股份有限公司 | 一种制备3‑甲基‑2‑丁烯醇的方法 |
| US10974225B1 (en) * | 2020-01-17 | 2021-04-13 | Zhejiang Nhu Company Ltd. | Metal oxide coated ceramic corrugated plate catalyst, preparation and application in preparation of key intermediates of citral |
-
1967
- 1967-12-08 DE DE19671643709 patent/DE1643709B1/de not_active Withdrawn - After Issue
-
1968
- 1968-03-22 DE DE19681768023 patent/DE1768023C3/de not_active Expired
- 1968-12-06 GB GB1239434D patent/GB1239434A/en not_active Expired
- 1968-12-06 BE BE725088D patent/BE725088A/xx not_active IP Right Cessation
- 1968-12-06 NL NL6817562.A patent/NL167408C/xx not_active IP Right Cessation
- 1968-12-09 CH CH1835968A patent/CH525173A/de not_active IP Right Cessation
- 1968-12-09 FR FR1594968D patent/FR1594968A/fr not_active Expired
- 1968-12-09 US US782420A patent/US3655735A/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122291A (en) * | 1976-06-08 | 1978-10-24 | Kuraray Co., Ltd. | Method for the production of alken-2-ol-1 or of alken-2-ol-1 and alkanol-1 |
| US4117016A (en) * | 1977-05-27 | 1978-09-26 | Phillips Petroleum Company | Process for structural modification of unsaturated alcohols |
| US4387047A (en) * | 1980-02-13 | 1983-06-07 | Firmenich Sa | Esters of 1,3-dimethyl-but-3-en-1-yl, their utilization as perfuming and flavoring ingredients and compositions containing same |
| CN102701910A (zh) * | 2012-05-24 | 2012-10-03 | 南开大学 | 一种通过异构化3-甲基-3-丁烯-1-醇制备异戊烯醇的方法 |
| CN104994949A (zh) * | 2013-01-23 | 2015-10-21 | 弗门尼舍有限公司 | 制备4-甲基戊-3-烯-1-醇衍生物的方法 |
| CN104994949B (zh) * | 2013-01-23 | 2018-02-23 | 弗门尼舍有限公司 | 制备4‑甲基戊‑3‑烯‑1‑醇衍生物的方法 |
| CN107141197A (zh) * | 2017-06-23 | 2017-09-08 | 万华化学集团股份有限公司 | 一种制备3‑甲基‑2‑丁烯醇的方法 |
| CN107141197B (zh) * | 2017-06-23 | 2020-08-28 | 万华化学集团股份有限公司 | 一种制备3-甲基-2-丁烯醇的方法 |
| US10974225B1 (en) * | 2020-01-17 | 2021-04-13 | Zhejiang Nhu Company Ltd. | Metal oxide coated ceramic corrugated plate catalyst, preparation and application in preparation of key intermediates of citral |
Also Published As
| Publication number | Publication date |
|---|---|
| BE725088A (enrdf_load_stackoverflow) | 1969-06-06 |
| GB1239434A (enrdf_load_stackoverflow) | 1971-07-14 |
| DE1768023A1 (de) | 1972-01-13 |
| DE1768023B2 (de) | 1972-11-30 |
| CH525173A (de) | 1972-07-15 |
| NL6817562A (enrdf_load_stackoverflow) | 1969-06-10 |
| DE1643709B1 (de) | 1971-07-08 |
| NL167408C (nl) | 1981-12-16 |
| FR1594968A (enrdf_load_stackoverflow) | 1970-06-08 |
| NL167408B (nl) | 1981-07-16 |
| DE1768023C3 (de) | 1973-06-28 |
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