NL8004128A - Werkwijze voor het vervaardigen van difunctionele alifatisch organische verbindingen. - Google Patents

Werkwijze voor het vervaardigen van difunctionele alifatisch organische verbindingen. Download PDF

Info

Publication number: NL8004128A
Authority: NL; Netherlands
Prior art keywords: formula; process according; acid; compound; catalyst
Prior art date: 1979-07-17

Application number

NL8004128A

Other languages

English (en)

Dutch (nl)

Original Assignee

Brichima Spa

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.)

1979-07-17

Filing date

1980-07-17

Publication date

1981-01-20

1980-07-17 Application filed by Brichima Spa filed Critical Brichima Spa

1981-01-20 Publication of NL8004128A publication Critical patent/NL8004128A/nl

Links

238000000034 method Methods 0.000 title claims description 27
238000004519 manufacturing process Methods 0.000 title 1
150000002894 organic compounds Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 15
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
-1 aliphatic organic compounds Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
229910002651 NO3 Inorganic materials 0.000 claims 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
238000009835 boiling Methods 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 27
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
XYBSWJNOXTVINF-UHFFFAOYSA-N cyclohexanone;propanenitrile Chemical compound CCC#N.O=C1CCCCC1 XYBSWJNOXTVINF-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
239000000243 solution Substances 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229910000359 iron(II) sulfate Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229940076286 cupric acetate Drugs 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VWPQCOZMXULHDM-UHFFFAOYSA-N 9-aminononanoic acid Chemical compound NCCCCCCCCC(O)=O VWPQCOZMXULHDM-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
FGFJYALWOJLWQR-UHFFFAOYSA-N cyclohexanone;propanoic acid Chemical compound CCC(O)=O.O=C1CCCCC1 FGFJYALWOJLWQR-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007858 starting material Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/40—Peroxy compounds containing nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/20—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms
- C07C409/22—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms having two —O—O— groups bound to the carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8004128A 1979-07-17 1980-07-17 Werkwijze voor het vervaardigen van difunctionele alifatisch organische verbindingen. NL8004128A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT24421/79A IT1122203B (it)	1979-07-17	1979-07-17	Processo per la produzione di composti organici alifatici,difunzionali
IT2442179		1979-07-17

Publications (1)

Publication Number	Publication Date
NL8004128A true NL8004128A (nl)	1981-01-20

Family

ID=11213455

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004128A NL8004128A (nl)	1979-07-17	1980-07-17	Werkwijze voor het vervaardigen van difunctionele alifatisch organische verbindingen.

Country Status (5)

Country	Link
DE (1)	DE3027111A1 (it)
FR (1)	FR2461696A1 (it)
GB (1)	GB2056442B (it)
IT (1)	IT1122203B (it)
NL (1)	NL8004128A (it)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2298405A (en) *	1939-09-07	1942-10-13	Research Corp	Cycloalkanyl peroxide and process of producing the same
US2870200A (en) *	1954-05-24	1959-01-20	Shell Dev	Production of unsaturated polycarboxylic acids and esters
FR1276989A (fr) *	1960-12-29	1961-11-24	Montedison Spa	Procédé de préparation de dérivés d'acides carboxyliques aliphatiques
FR2199531B1 (it) *	1972-09-18	1975-03-14	Rhone Poulenc Ind

1979
- 1979-07-17 IT IT24421/79A patent/IT1122203B/it active
1980
- 1980-07-17 DE DE19803027111 patent/DE3027111A1/de not_active Withdrawn
- 1980-07-17 FR FR8015828A patent/FR2461696A1/fr active Granted
- 1980-07-17 NL NL8004128A patent/NL8004128A/nl not_active Application Discontinuation
- 1980-07-18 GB GB8023573A patent/GB2056442B/en not_active Expired

Also Published As

Publication number	Publication date
DE3027111A1 (de)	1981-02-19
GB2056442A (en)	1981-03-18
FR2461696B1 (it)	1983-07-22
FR2461696A1 (fr)	1981-02-06
GB2056442B (en)	1983-06-29
IT7924421A0 (it)	1979-07-17
IT1122203B (it)	1986-04-23

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1986-03-03	BV	The patent application has lapsed

Publication	Publication Date	Title
Boese Jr	1940	Diketene A New Industrial Chemical
Johnson	2004	The P erkin Reaction and Related Reactions
DE2504924B2 (de)	1979-06-07	Verfahren zur Herstellung von Azinen und/oder Hydrazonen
EP0566468A2 (fr)	1993-10-20	Procédé de préparation d'un dérivé de biphényl
JP4039693B2 (ja)	2008-01-30	農薬中間体を調製する新しいプロセス
JPS6042337A (ja)	1985-03-06	モノメチル−置換されたメチレン化合物類の製造方法
NL8004128A (nl)	1981-01-20	Werkwijze voor het vervaardigen van difunctionele alifatisch organische verbindingen.
US2525794A (en)	1950-10-17	Preparation of beta-amino carboxylic acids by the reaction of ammonia with beta-lactones
Rosenthal et al.	1963	Carboxylation of propargyl alcohol
Feuer et al.	1962	The Chemistry of Cyclic Hydrazides. 1 VII. The Course of the Michael-Type Addition with Cyclic Hydrazides2
Verzele et al.	1949	On the constitution of the β hops acid
US4322547A (en)	1982-03-30	Process for producing difunctional aliphatic organic compounds
US5274171A (en)	1993-12-28	Process for the palladium catalyzed coupling of a diazonium salt with an olefinic bond
US4132728A (en)	1979-01-02	Preparation of nitriles
Aburel et al.	2000	Rhodium (II)-carbenoid C–H insertion reactions in the synthesis of β-oxospirane systems
US4180520A (en)	1979-12-25	Preparation of nitriles
CH627727A5 (en)	1982-01-29	Process for the preparation of phenylalkylcarboxylic acids
GB1577070A (en)	1980-10-15	Process for the preparation of condensation products of substituted acetic acid esters with aldehydes
US3355483A (en)	1967-11-28	Alkyl substituted difunctional hexanes
JPH06507154A (ja)	1994-08-11	シアノ酢酸の生産方法
DE2938689A1 (de)	1981-04-09	Aliphatische methoxy- und hydroxynitrile, deren herstellung und deren verwendung als riechstoff
CA2257825C (en)	2006-08-22	New processes for preparing pesticidal intermediates
EP0649831B1 (de)	1998-10-14	Verfahren zur Herstellung von 3-(p-Fluorphenyl)-2-methylpropionsäure und 3-(p-Fluorphenyl)-2-methylpropionsäurederivaten
US3484438A (en)	1969-12-16	Phenthiazine derivatives
US2551566A (en)	1951-05-01	Production of alpha-amino, alphacyano glutaric acid compounds and certain alkyl derivatives