DD146283A5 - Verfahren zur herstellung von 2-propyl-pent-4-en-1-al - Google Patents

Verfahren zur herstellung von 2-propyl-pent-4-en-1-al Download PDF

Info

Publication number: DD146283A5
Authority: DD; German Democratic Republic
Prior art keywords: pent; propyl; acetal; preparation; ether
Prior art date: 1978-10-13

Application number

DD79216030A

Other languages

German (de)

English (en)

Inventor

Juergen Weber

Wolfgang Bernhagen

Helmut Springer

Original Assignee

Ruhrchemie Ag

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.)

1978-10-13

Filing date

1979-10-04

Publication date

1981-02-04

1979-10-04 Application filed by Ruhrchemie Ag filed Critical Ruhrchemie Ag

1981-02-04 Publication of DD146283A5 publication Critical patent/DD146283A5/de

Links

KCZBNTGSHQURPY-UHFFFAOYSA-N 2-propylpent-4-enal Chemical compound CCCC(C=O)CC=C KCZBNTGSHQURPY-UHFFFAOYSA-N 0.000 title claims abstract description 13
238000004519 manufacturing process Methods 0.000 title description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 8
150000002170 ethers Chemical class 0.000 claims abstract description 5
-1 valeraldehyde diallyl acetal Chemical class 0.000 claims abstract description 5
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
238000000034 method Methods 0.000 claims description 3
239000003205 fragrance Substances 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 abstract description 3
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 10
150000001241 acetals Chemical class 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 7
QUMSUJWRUHPEEJ-UHFFFAOYSA-N 4-Pentenal Chemical compound C=CCCC=O QUMSUJWRUHPEEJ-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
DTCCTIQRPGSLPT-UHFFFAOYSA-N 2-pentenal Chemical class CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 description 1
BAUHZKXBGXCLBO-UHFFFAOYSA-N 2-propylpentanal Chemical compound CCCC(C=O)CCC BAUHZKXBGXCLBO-UHFFFAOYSA-N 0.000 description 1
IQXKGRKRIRMQCQ-UHFFFAOYSA-N 4-methylheptan-4-ol Chemical compound CCCC(C)(O)CCC IQXKGRKRIRMQCQ-UHFFFAOYSA-N 0.000 description 1
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
WDLUEZJSSHTKAP-UHFFFAOYSA-N acetaldehyde;1,1-diethoxyethane Chemical compound CC=O.CCOC(C)OCC WDLUEZJSSHTKAP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cosmetics (AREA)
Fats And Perfumes (AREA)

DD79216030A 1978-10-13 1979-10-04 Verfahren zur herstellung von 2-propyl-pent-4-en-1-al DD146283A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2844635A DE2844635C2 (de)	1978-10-13	1978-10-13	2-Propyl-pent-4-en-l-al und Verfahren zu seiner Herstellung

Publications (1)

Publication Number	Publication Date
DD146283A5 true DD146283A5 (de)	1981-02-04

Family

ID=6052101

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79216030A DD146283A5 (de)	1978-10-13	1979-10-04	Verfahren zur herstellung von 2-propyl-pent-4-en-1-al

Country Status (10)

Country	Link
US (2)	US4270008A (pt)
EP (1)	EP0010235B1 (pt)
JP (1)	JPS5912092B2 (pt)
AT (1)	AT370405B (pt)
BR (1)	BR7906592A (pt)
CA (1)	CA1105945A (pt)
DD (1)	DD146283A5 (pt)
DE (1)	DE2844635C2 (pt)
DK (1)	DK429179A (pt)
NL (1)	NL173051C (pt)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3421809A1 (de) *	1984-06-12	1985-12-12	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von 2-methyl-2-alkenalen
US5079266A (en) *	1988-01-04	1992-01-07	Betz Laboratories, Inc.	Method of generating acrolein
US4851583A (en) *	1988-01-04	1989-07-25	Betz Laboratories, Inc.	Method of generating acrolein
US5053556A (en) *	1989-01-31	1991-10-01	Chisso Corporation	Process for producing alkenyl ethers
FR2661408B1 (fr) *	1990-04-27	1993-09-17	Rhone Poulenc Nutrition Animal	Procede de preparation de citral.
US5731476A (en) *	1995-01-13	1998-03-24	Arco Chemical Technology, L.P.	Poly ether preparation
US5476971A (en) *	1995-01-13	1995-12-19	Arco Chemical Technology, L.P.	Glycerine ditertiary butyl ether preparation
JPWO2006075596A1 (ja) *	2005-01-13	2008-06-12	株式会社クラレ	２−アリルカルボン酸化合物の製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3359324A (en) *	1961-02-01	1967-12-19	Union Carbide Corp	Method of preparing 2, 3-dimethyl-4-pentenal
US4107217A (en) *	1973-07-30	1978-08-15	International Flavors & Fragrances Inc.	Acetals of conjugated alkenals
DE2517447C2 (de) *	1975-04-19	1977-03-03	Basf Ag	Verfahren zur herstellung von pent-4-en-1-al

1978
- 1978-10-13 DE DE2844635A patent/DE2844635C2/de not_active Expired
- 1978-11-17 NL NLAANVRAGE7811368,A patent/NL173051C/xx not_active IP Right Cessation
1979
- 1979-10-04 DD DD79216030A patent/DD146283A5/de unknown
- 1979-10-04 AT AT0647579A patent/AT370405B/de not_active IP Right Cessation
- 1979-10-05 EP EP79103814A patent/EP0010235B1/de not_active Expired
- 1979-10-08 JP JP54128963A patent/JPS5912092B2/ja not_active Expired
- 1979-10-11 BR BR7906592A patent/BR7906592A/pt unknown
- 1979-10-11 US US06/083,893 patent/US4270008A/en not_active Expired - Lifetime
- 1979-10-11 DK DK429179A patent/DK429179A/da not_active Application Discontinuation
- 1979-10-12 CA CA337,437A patent/CA1105945A/en not_active Expired
1980
- 1980-07-30 US US06/173,792 patent/US4307252A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US4307252A (en)	1981-12-22
JPS5553231A (en)	1980-04-18
DE2844635B1 (de)	1980-03-13
ATA647579A (de)	1982-08-15
EP0010235B1 (de)	1981-12-23
DE2844635C2 (de)	1980-11-06
BR7906592A (pt)	1980-07-15
AT370405B (de)	1983-03-25
CA1105945A (en)	1981-07-28
US4270008A (en)	1981-05-26
NL7811368A (nl)	1980-04-15
DK429179A (da)	1980-04-14
JPS5912092B2 (ja)	1984-03-21
EP0010235A1 (de)	1980-04-30
NL173051B (nl)	1983-07-01
NL173051C (nl)	1983-12-01

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DD146283A5 (de)	1981-02-04	Verfahren zur herstellung von 2-propyl-pent-4-en-1-al
US4088681A (en)	1978-05-09	Substituted 1-alkenynyl-cyclohexanols and -cyclohexenes and processes for their preparation
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DE2513996C3 (de)	1979-12-20	Cyc lopentenderivate
DE2141309A1 (pt)	1972-03-02
EP0043507B1 (de)	1984-08-22	2,4-Dioxa-7,10-methano-spiro(5,5)undecane, deren Herstellung sowie diese enthaltende Riechstoffkompositionen
DE434989C (de)	1926-10-06	Verfahren zur Herstellung zyklischer Acetale ungesaettigter aliphatischer Aldehyde
DE69309390T2 (de)	1997-11-06	Enolether und sie enthaltende Riechstoffkompositionen
DE2914109A1 (de)	1979-10-18	1,3-dioxane und sie enthaltende parfuemzubereitung
DE2313017C3 (de)	1980-03-20	Cyclopentene und Verfahren zu deren Herstellung
US3361820A (en)	1968-01-02	Pinene derivative
DE2510861A1 (de)	1975-09-18	Neue riechstoffe
CH627429A5 (de)	1982-01-15	Verfahren zur herstellung von aldehyden.
DE2900975C2 (de)	1981-02-19	2-Ethyl-3-methyl-pent-4-en-l-al
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CH628868A5 (en)	1982-03-31	Process for the preparation of acyclic monoterpene alcohols
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