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1. (WO2017098050) PROCESS FOR THE MANUFACTURE OF 6,10,14-TRIMETHYLPENTADECAN-2-ONE, ISOPHYTOL AND ALPHA-TOCOPHEROL
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/2017/098050 International Application No.: PCT/EP2016/080664
Publication Date: 15.06.2017 International Filing Date: 12.12.2016
IPC:
C07C 45/62 (2006.01) ,C07C 49/04 (2006.01) ,C07C 45/72 (2006.01) ,C07C 49/203 (2006.01) ,C07C 29/17 (2006.01) ,C07C 29/38 (2006.01) ,C07C 45/29 (2006.01) ,C07C 45/38 (2006.01) ,C07C 33/02 (2006.01) ,C07C 33/042 (2006.01) ,C07C 47/21 (2006.01) ,C07D 311/72 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
45
Preparation of compounds having CO groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61
by reactions not involving the formation of CO groups
62
by hydrogenation of carbon-to-carbon double or triple bonds
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
49
Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
04
Saturated compounds containing keto groups bound to acyclic carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
45
Preparation of compounds having CO groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61
by reactions not involving the formation of CO groups
67
by isomerisation; by change of size of the carbon skeleton
68
by increase in the number of carbon atoms
72
by reaction of compounds containing CO groups with the same or other compounds containing CO groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
49
Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
20
Unsaturated compounds containing keto groups bound to acyclic carbon atoms
203
with only carbon-to-carbon double bonds as unsaturation
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
29
Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
17
by hydrogenation of carbon-to-carbon double or triple bonds
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
29
Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
36
increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy groups, e.g. O-metal
38
by reaction with aldehydes or ketones
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
45
Preparation of compounds having CO groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
27
by oxidation
29
of hydroxy groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
45
Preparation of compounds having CO groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
27
by oxidation
32
with molecular oxygen
37
of C-O- functional groups to CO groups
38
being a primary hydroxy group
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
33
Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
02
Acyclic alcohols with carbon-to-carbon double bonds
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
33
Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
04
Acyclic alcohols with carbon-to-carbon triple bonds
042
with only one triple bond
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
47
Compounds having -CHO groups
20
Unsaturated compounds having -CHO groups bound to acyclic carbon atoms
21
with only carbon-to-carbon double bonds as unsaturation
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
311
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
02
ortho- or peri-condensed with carbocyclic rings or ring systems
04
Benzo [b] pyrans, not hydrogenated in the carbocyclic ring
58
other than with oxygen or sulfur atoms in position 2 or 4
70
with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
72
3, 4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Applicants:
DSM IP ASSETS B.V. [NL/NL]; Het Overloon 1 6411 Te Heerlen, NL
Inventors:
BONRATH, Werner; CH
MEDLOCK, Jonathan Alan; CH
RIEBEL, Peter Hans; CH
STEMMLER, Rene Tobias; CH
Agent:
STECK, Melanie; CH
Priority Data:
EP15199585.911.12.2015EP
Title (EN) PROCESS FOR THE MANUFACTURE OF 6,10,14-TRIMETHYLPENTADECAN-2-ONE, ISOPHYTOL AND ALPHA-TOCOPHEROL
(FR) PROCÉDÉ DE PRODUCTION DU 6,10,14-TRIMÉTHYLPENTADÉCAN-2-ONE, ISOPHYTOL ET ALPHA-TOCOPHÉROL
Abstract:
(EN) The present invention is directed to a process for the manufacture of 6,10,14-trimethylpentadecan-2-one ("C18-ketone") comprising the step of hydrogenating a mixture of (3E,5E,9E)-3,4-dehydrofarnesylacetone and (3Z,5E,9E)-3,4-dehydrofarnesylacetone with hydrogen in the presence of a catalyst, whereby the catalyst is capable of preferentially hydrogenating carbon-carbon double bonds over carbon-oxygen double bonds. Preferably the catalyst comprises a metal selected from the group consisting of palladium, platinum, rhodium, iridium and nickel and mixtures thereof. A process for the preparation of (2E,6E)-farnesal by selective oxidation of (2E,6E)-farnesol and a process for the manufacture of a mixture of (3E,5E,9E)-3,4-dehydrofarnesylacetone and (3Z,5E,9E)-3,4-dehydrofarnesylacetone from (2E,6E)-farnesal is also disclosed.
(FR) La présente invention concerne un procédé de production du 6,10,14-triméthylpentadécan-2-one ("cétone en C18") comprenant l'étape consistant à hydrogéner un mélange de (3E,5E,9E)-3,4-déshydrofarnésylacétone et de (3Z,5E,9E)-3,4-déshydrofarnésylacétone avec de l'hydrogène en présence d'un catalyseur, le catalyseur pouvant hydrogéner de préférence les liaisons doubles carbone-carbone par rapport aux liaisons doubles carbone-oxygène. Le catalyseur comprend de préférence un métal choisi dans le groupe constitué par le palladium, le platine, le rhodium, l'iridium et le nickel, et des mélanges de ceux-ci. L'invention concerne également un procédé de préparation du (2E,6E)-farnésal par oxydation sélective du (2E,6E)-farnésol et un procédé de fabrication d'un mélange de (3E,5E,9E)-3,4-déshydrofarnésylacétone et de (3Z,5E,9E)-3,4-déshydrofarnésylacétone à partir du (2E,6E)-farnésal.
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Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)