EP2231576A1 - Verfahren zur gewinnung von alkohol aus einem aldehyd - Google Patents

Verfahren zur gewinnung von alkohol aus einem aldehyd

Info

Publication number: EP2231576A1
Authority: EP; European Patent Office
Prior art keywords: aldehyde; weight; acidic; bar; solid compound
Prior art date: 2007-12-14
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP08862544A

Other languages

English (en)

French (fr)

Inventor

Danilo Zim

Philippe Marion

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rhodia Poliamida e Especialidades Ltda

Original Assignee

Rhodia Poliamida e Especialidades Ltda

Priority date (The priority date 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 date listed.)

2007-12-14

Filing date

2008-12-10

Publication date

2010-09-29

2008-12-10 Application filed by Rhodia Poliamida e Especialidades Ltda filed Critical Rhodia Poliamida e Especialidades Ltda

2010-09-29 Publication of EP2231576A1 publication Critical patent/EP2231576A1/de

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 5
239000003054 catalyst Substances 0.000 claims abstract description 15
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 15
150000001299 aldehydes Chemical class 0.000 claims description 25
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 18
239000007787 solid Substances 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 13
230000002378 acidificating effect Effects 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
150000002736 metal compounds Chemical class 0.000 claims description 10
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
238000005882 aldol condensation reaction Methods 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
239000011347 resin Substances 0.000 claims description 8
229920005989 resin Polymers 0.000 claims description 8
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 6
229910052763 palladium Inorganic materials 0.000 claims description 6
229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
229910052741 iridium Inorganic materials 0.000 claims description 4
239000011707 mineral Substances 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
229910052697 platinum Inorganic materials 0.000 claims description 4
229910052703 rhodium Inorganic materials 0.000 claims description 4
239000010457 zeolite Substances 0.000 claims description 4
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
229910052804 chromium Inorganic materials 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
239000007791 liquid phase Substances 0.000 claims description 3
229910019142 PO4 Inorganic materials 0.000 claims description 2
229910021536 Zeolite Inorganic materials 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
239000000919 ceramic Substances 0.000 claims description 2
239000004927 clay Substances 0.000 claims description 2
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
239000007792 gaseous phase Substances 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052901 montmorillonite Inorganic materials 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
-1 H-ZSM5 Chemical class 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
150000001412 amines Chemical group 0.000 claims 1
229910052746 lanthanum Inorganic materials 0.000 claims 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 1
229910044991 metal oxide Inorganic materials 0.000 claims 1
150000004706 metal oxides Chemical class 0.000 claims 1
235000021317 phosphate Nutrition 0.000 claims 1
150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
238000009833 condensation Methods 0.000 abstract description 6
230000005494 condensation Effects 0.000 abstract description 6
230000001588 bifunctional effect Effects 0.000 abstract description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
239000011949 solid catalyst Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000007037 hydroformylation reaction Methods 0.000 description 2
MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum oxide Inorganic materials [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
239000002028 Biomass Substances 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000135 prohibitive effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration

Definitions

Amberlyst® CH28 catalysts from Rohm & Haas can be mentioned.
the reaction of the first step can be carried out in a reactor of any type, in particular in a vertically mounted reaction tube. Many reactors implementing the method of the first step can be put in series.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

EP08862544A 2007-12-14 2008-12-10 Verfahren zur gewinnung von alkohol aus einem aldehyd Withdrawn EP2231576A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0708723A FR2925046A1 (fr)	2007-12-14	2007-12-14	Procede d'obtention d'alcool a partir d'un aldehyde
PCT/IB2008/003407 WO2009077831A1 (fr)	2007-12-14	2008-12-10	Procede d'obtention d'alcool a partir d'un aldehyde

Publications (1)

Publication Number	Publication Date
EP2231576A1 true EP2231576A1 (de)	2010-09-29

Family

ID=39645585

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP08862544A Withdrawn EP2231576A1 (de)	2007-12-14	2008-12-10	Verfahren zur gewinnung von alkohol aus einem aldehyd

Country Status (8)

Country	Link
US (1)	US20110021845A1 (de)
EP (1)	EP2231576A1 (de)
JP (1)	JP2011517656A (de)
CN (1)	CN101925569A (de)
BR (1)	BRPI0819373A2 (de)
FR (1)	FR2925046A1 (de)
WO (1)	WO2009077831A1 (de)
ZA (1)	ZA201004638B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1885676A2 (de)	2005-05-20	2008-02-13	Solvay SA	Verfahren zur umwandlung mehrfach hydroxylierter aliphatischer kohlenwasserstoffe in chlorhydrine
ES2469829T3 (es) *	2009-11-26	2014-06-20	Sandoz Ag	Reacción de compuestos orgánicos con bajas cantidades de hidrógeno
CN102093180B (zh) *	2009-12-15	2013-09-11	上海焦化有限公司	一种连续生产不饱和醛化合物的方法
CN102093179A (zh) *	2009-12-15	2011-06-15	上海焦化有限公司	一种酸性沸石催化醛缩合的方法
US8742177B2 (en)	2011-12-28	2014-06-03	Rohm And Haas Company	Catalyst and process to produce branched unsaturated aldehydes
US8809594B2 (en)	2012-09-21	2014-08-19	Eastman Chemical Company	Dual catalyst system for the self-condensation of alcohols
EP3048090B1 (de) *	2013-09-17	2022-03-30	LG Chem, Ltd.	Verfahren zur herstellung von alkanol
DK3160927T3 (da) *	2014-06-30	2022-06-13	Haldor Topsoe As	Fremgangsmåde til fremstilling af ethylenglycol ud fra sukker
AU2017205691B2 (en)	2016-01-07	2021-06-17	Haldor Topsøe A/S	Process for the preparation of ethylene glycol from sugars
KR102737311B1 (ko)	2016-01-07	2024-12-03	토프쉐 에이/에스	당으로부터 에틸렌글리콜의 제조를 위한 과정
US9834501B2 (en)	2016-01-28	2017-12-05	Eastman Chemical Company	Efficient synthesis of methacroelin and other alpha, beta—unsaturated aldehydes from methanol and an aldehyde
US9828322B2 (en)	2016-01-28	2017-11-28	Eastman Chemical Company	Efficient synthesis of methacroelin and other alpha, beta-unsaturated aldehydes over a regenerable anatase titania catalyst
CN106111184A (zh) *	2016-06-27	2016-11-16	山东成泰化工有限公司	一种异癸醇制备用催化剂及其制备方法
CN110871085B (zh) *	2018-08-30	2022-11-29	淄博张店东方化学股份有限公司	一种糠醛催化加氢制备糠醇的负载型催化剂及其制备方法与应用
CN114685257B (zh) *	2020-12-31	2024-04-09	中国石油化工股份有限公司	一种合成甲基异戊基酮的方法

Family Cites Families (3)

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US5004845A (en) *	1981-08-20	1991-04-02	Davy Mckee (London) Limited	Hydrogenation of aldehydes
US4701562A (en) *	1986-06-25	1987-10-20	Union Carbide Corporation	Process for the condensation of aldehydes
DE69908777T2 (de) *	1999-10-20	2004-03-04	Saudi Basic Industries Corp.	Flüssigphase katalytisches Hydrierungsverfahren zur Umwandlung von Aldehyden in die entsprechenden Alkohole

2007
- 2007-12-14 FR FR0708723A patent/FR2925046A1/fr active Pending
2008
- 2008-12-10 EP EP08862544A patent/EP2231576A1/de not_active Withdrawn
- 2008-12-10 WO PCT/IB2008/003407 patent/WO2009077831A1/fr not_active Ceased
- 2008-12-10 US US12/747,647 patent/US20110021845A1/en not_active Abandoned
- 2008-12-10 JP JP2010537532A patent/JP2011517656A/ja not_active Abandoned
- 2008-12-10 CN CN200880125414XA patent/CN101925569A/zh active Pending
- 2008-12-10 BR BRPI0819373 patent/BRPI0819373A2/pt not_active IP Right Cessation
2010
- 2010-07-01 ZA ZA2010/04638A patent/ZA201004638B/en unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009077831A1 *

Also Published As

Publication number	Publication date
ZA201004638B (en)	2011-03-30
JP2011517656A (ja)	2011-06-16
US20110021845A1 (en)	2011-01-27
WO2009077831A1 (fr)	2009-06-25
BRPI0819373A2 (pt)	2015-04-22
CN101925569A (zh)	2010-12-22
FR2925046A1 (fr)	2009-06-19

Legal Events

Date	Code	Title	Description
2010-08-27	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
2010-09-29	17P	Request for examination filed	Effective date: 20100604
2010-09-29	AK	Designated contracting states	Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR
2010-09-29	AX	Request for extension of the european patent	Extension state: AL BA MK RS
2011-03-23	DAX	Request for extension of the european patent (deleted)
2012-07-03	GRAP	Despatch of communication of intention to grant a patent	Free format text: ORIGINAL CODE: EPIDOSNIGR1
2013-04-05	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN
2013-05-08	18D	Application deemed to be withdrawn	Effective date: 20121114

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