EP0000478A1 - Procédé de préparation d'acyloines - Google Patents

Procédé de préparation d'acyloines Download PDF

Info

Publication number: EP0000478A1
Authority: EP; European Patent Office
Prior art keywords: carbon atoms; chain; catalysts; mol; hydroxyethyl
Prior art date: 1977-07-20
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.): Granted

Application number

EP78100262A

Other languages

German (de)

English (en)

Other versions

EP0000478B1 (fr

Inventor

Horst-Jürgen Dr. Krause

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.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

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.)

1977-07-20

Filing date

1978-06-28

Publication date

1979-02-07

1978-06-28 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1979-02-07 Publication of EP0000478A1 publication Critical patent/EP0000478A1/fr

1981-11-25 Application granted granted Critical

1981-11-25 Publication of EP0000478B1 publication Critical patent/EP0000478B1/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
239000003054 catalyst Substances 0.000 claims abstract description 8
238000009833 condensation Methods 0.000 claims abstract description 3
230000005494 condensation Effects 0.000 claims abstract description 3
239000004793 Polystyrene Substances 0.000 claims abstract 2
239000007795 chemical reaction product Substances 0.000 claims abstract 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract 2
229920002223 polystyrene Polymers 0.000 claims abstract 2
150000003557 thiazoles Chemical class 0.000 claims abstract 2
239000011347 resin Substances 0.000 claims description 8
229920005989 resin Polymers 0.000 claims description 8
BKAWJIRCKVUVED-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methylthiazole Chemical compound CC=1N=CSC=1CCO BKAWJIRCKVUVED-UHFFFAOYSA-N 0.000 claims description 6
MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 claims description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
239000000376 reactant Substances 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 abstract description 5
238000004519 manufacturing process Methods 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
-1 alkyl radical Chemical class 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
GUPGZURVZDIQPM-UHFFFAOYSA-N 2-oxoethyl acetate Chemical compound CC(=O)OCC=O GUPGZURVZDIQPM-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups

Definitions

the invention relates to a process for the preparation of acyloin by condensing aldehydes in the presence of thiazolium salts.
R 3 represents a straight-chain or branched alkyl radical having 1 to 18 carbon atoms, a cycloalkyl radical having 3 to 18 carbon atoms, an arylalkyl radical having 7 to 18 carbon atoms or the group in which n is an integer from 2 to 4.
aldehydes which can be used as starting material in the process according to the invention are: acetaldehyde, acetoxy-acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, pivalinaldehyde, valeraldehyde, iso-valereldehyde, capronaldehyde, enanthaldehyde, 2- Ethyl hexanal capryl aldehyde,
the resin containing 5- (2'-hydroxyethyl) -4-methyl-1,3-thiazoliving group contained 8.61% by weight of ionic chloride; the total log content was 9.33% by weight.
the resin catalyst obtained in this way removes 7.17% by weight of ionic chlorine; the total chlorine content was 7.68% by weight.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

EP78100262A 1977-07-20 1978-06-28 Procédé de préparation d'acyloines Expired EP0000478B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2732714A DE2732714C2 (de)	1977-07-20	1977-07-20	Verfahren zur Herstellung von Acyloinen
DE2732714		1977-07-20

Publications (2)

Publication Number	Publication Date
EP0000478A1 true EP0000478A1 (fr)	1979-02-07
EP0000478B1 EP0000478B1 (fr)	1981-11-25

Family

ID=6014352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP78100262A Expired EP0000478B1 (fr)	1977-07-20	1978-06-28	Procédé de préparation d'acyloines

Country Status (3)

Country	Link
EP (1)	EP0000478B1 (fr)
JP (1)	JPS5422310A (fr)
DE (1)	DE2732714C2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6329466B1 (en)	1996-09-04	2001-12-11	The Dow Chemical Company	Blends of α-olefin/vinylidene aromatic monomer or hindered aliphatic vinylidene interpolymers with polyolefins

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008222596A (ja) *	2007-03-09	2008-09-25	Asahi Kasei Chemicals Corp	シス二重結合含有ジカルボン酸誘導体の製造方法
CN104744615B (zh) *	2013-12-25	2017-05-24	浙江衢州万能达科技有限公司	一种全氟季铵型强碱性阴离子交换树脂的制备方法
CN106397151B (zh) *	2016-08-31	2019-06-11	濮阳天源生物科技有限公司	一种偶姻类化合物的制备方法

1977
- 1977-07-20 DE DE2732714A patent/DE2732714C2/de not_active Expired
1978
- 1978-06-28 EP EP78100262A patent/EP0000478B1/fr not_active Expired
- 1978-07-19 JP JP8722778A patent/JPS5422310A/ja active Granted

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J.CHEM.SOC.CHEM.COMM., 891(1973) (In der Anmeldung angef}hrt), " Acyloin condensation cf Aldehydes catalysed by N-Laurylthiazolium Bromide"; linke Spalte, Abschnitt 1, Mitte, Fussnote 2. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6329466B1 (en)	1996-09-04	2001-12-11	The Dow Chemical Company	Blends of α-olefin/vinylidene aromatic monomer or hindered aliphatic vinylidene interpolymers with polyolefins

Also Published As

Publication number	Publication date
DE2732714C2 (de)	1985-08-14
EP0000478B1 (fr)	1981-11-25
JPS5422310A (en)	1979-02-20
JPS6223733B2 (fr)	1987-05-25
DE2732714A1 (de)	1979-02-08

Legal Events

Date	Code	Title	Description
1978-12-13	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
1979-02-07	AK	Designated contracting states	Designated state(s): BE CH FR GB NL
1980-04-16	17P	Request for examination filed
1981-09-26	GRAA	(expected) grant	Free format text: ORIGINAL CODE: 0009210
1981-11-25	AK	Designated contracting states	Designated state(s): BE CH FR GB NL
1984-03-28	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: FR Payment date: 19840328 Year of fee payment: 7
1984-05-21	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: CH Payment date: 19840521 Year of fee payment: 7
1984-09-30	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: BE Payment date: 19840930 Year of fee payment: 7
1987-06-30	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: NL Payment date: 19870630 Year of fee payment: 10
1988-06-28	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: GB Effective date: 19880628
1988-06-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: CH Effective date: 19880630
1988-12-31	BERE	Be: lapsed	Owner name: HENKEL K.G.A.A. Effective date: 19880630
1989-01-01	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: NL Effective date: 19890101
1989-02-16	NLV4	Nl: lapsed or anulled due to non-payment of the annual fee
1989-02-22	GBPC	Gb: european patent ceased through non-payment of renewal fee
1989-02-28	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19890228
1989-02-28	REG	Reference to a national code	Ref country code: CH Ref legal event code: PL
1989-04-21	REG	Reference to a national code	Ref country code: FR Ref legal event code: ST
1989-06-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: BE Effective date: 19890630
2016-09-14	PLBE	No opposition filed within time limit	Free format text: ORIGINAL CODE: 0009261
2016-09-14	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

Publication	Publication Date	Title
DE69206745T2 (de)	1996-05-23	Herstellung von neopentylglycol
JP2895633B2 (ja)	1999-05-24	アルキルイミダゾリドン（メタ）アクリレートの製造方法
DE2523838A1 (de)	1976-02-19	Verfahren zur herstellung von gemischen aus butandiol-(1,4) und 2-methylpropandiol-(1,3)
DE4437667A1 (de)	1996-04-25	Verfahren zur Herstellung von N,N'-disubstituierten p-Chinondiiminen, deren Verwendung und Methacryloxy- oder Acryloxy-Gruppen enthaltende Organosilane, Verfahren zu deren Stabilisierung und deren Herstellung
EP0000478A1 (fr)	1979-02-07	Procédé de préparation d'acyloines
US2593267A (en)	1952-04-15	Organotin compounds and compositions containing the same
DE2418387A1 (de)	1974-11-07	Siliciumhaltige nitrophenylaether
US3236900A (en)	1966-02-22	Diallyl ethers
DE2706842C2 (de)	1985-10-24	Verfahren zur Herstellung von 2,3,5-Trimethylhydrochinon
DE947475C (de)	1956-08-16	Verfahren zur Herstellung von neuen Hexaorganoaethinyldisilanen
US5166453A (en)	1992-11-24	Method for purification of ethylene compounds having fluorine-containing organic group
DE3050815C2 (de)	1985-06-20	Polymere, gegebenenfalls über Silicium-, Titan- oder Aluminium-Brückenatome vernetzte Organosiloxanphosphine
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US2195382A (en)	1940-03-26	Unsaturated furoate
DE2759994C2 (de)	1984-09-20	Ketale von 4-(1-Hydroxy-1-methylethyl)-3-cyclohexen-1-on und Verfahren zu ihrer Herstellung
US3509182A (en)	1970-04-28	Production of acetals and mercaptals
DE1154477B (de)	1963-09-19	Verfahren zur Herstellung von Nitro- oder Nitritogruppen enthaltenden Silanen
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EP0123123A2 (fr)	1984-10-31	Procédé de préparation de 2-isopropényloxazolines
DE69405524T2 (de)	1998-04-23	Depolymerisation von cyclischen Trimeren von chlorierten Aldehyden
EP0065356B1 (fr)	1985-08-07	Procédé de purification de cyclopenténolones
DE3508641C1 (de)	1986-09-18	Verfahren zur Herstellung von Cyclohexen-3-ylidenmethyl-benzylether
US3084193A (en)	1963-04-02	Preparation of tropolones from
US2991233A (en)	1961-07-04	Purification of alpha, beta-unsaturated aliphatic aldehydes

EP0000478A1 - Procédé de préparation d'acyloines - Google Patents

Info

Links

Classifications

Definitions

Landscapes

Applications Claiming Priority (2)

Publications (2)

Family

ID=6014352

Family Applications (1)

Country Status (3)

Cited By (1)

Families Citing this family (3)

Non-Patent Citations (1)

Cited By (1)

Also Published As

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Legal Events