WO1994029257B1 - Process for producing an omega-functionalized aliphatic carboxylic acid and intermediate products of said process - Google Patents
Process for producing an omega-functionalized aliphatic carboxylic acid and intermediate products of said processInfo
- Publication number
- WO1994029257B1 WO1994029257B1 PCT/EP1994/001865 EP9401865W WO9429257B1 WO 1994029257 B1 WO1994029257 B1 WO 1994029257B1 EP 9401865 W EP9401865 W EP 9401865W WO 9429257 B1 WO9429257 B1 WO 9429257B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chr
- formula
- ooc
- omega
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 7
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000004711 α-olefin Substances 0.000 abstract 1
Abstract
A process for producing an omega-functionalized aliphatic carboxylic acid starting from cyclohexanone and omega-functionalized α-olefins. The process comprises an addition step, an oxidation step, an isomerization step, one or more hydrogenation steps and hydrolysis (I). The process allows to use raw materials that are available at low cost and to achieve high selectivity and high yield with industrially simple steps. The process includes the production of new intermediate products.
Claims
AMENDED CLAIMS
[received by the International Bureau on 16 December 1994 (16.12.94); original claims 14-22 replaced by amended claims 14-19; original claims 1-13 unchanged (2 pages)]
(iii) is performed at a temperature between 20 and 200°C, preferably at a temperature between 30 and 130°C, more preferably at a temperature between 40 and 70°C, and at a pressure between 1 and 200 bar (0.1 and 20 MPa), preferably at a pressure between 2 and 130 bar (0.2 and 13 MPa) and comprises basic saponification and acidification to obtain a dicarboxylic acid.
13. Process according to at least one of the preceding claims, wherein R7 is CHOH-CH2, said step (iii) comprising dehydration or dehydrohalogenation or deal oxylation of the compound with formula (5) .
14. Compound with formula (5)
R1OOC-CHR2-CHR3-CHR -CH2-R7-CH2-R5 (5)
where each one of R1, R2, R3, and R4 is: hydrogen, alkyl, alkyl aryl, halogen or hydroxyl; R5 is Y or a group that can be transformed into Y with known methods; Y is -COOH, - CN, -CONH2 or COOR ; R6 is an optionally substituted alkyl or aryl radical; R7 is CH=CH or CHR8-CH2; R8 is OH, OCOCH3, OCH3, OEt or halogen.
15. Compound according to claim 14, with formula (8)
R1OOC-CHR2-CHR3-CHR4-CH2-CH=CH-CH2-R5 (8)
where R-*—R7 have the same meaning.
16. Compound according to claim 14, with formula (9)
R1OOC-CHR2-CHR3-CHR4-CH2-R7-CH2-R5 (9)
where R-"--R have the same meaning; R is CHOH-CH2, CHOCOCH3-CH2 , CHOCH3-CH2, CHOEt-CH2, CHhalogen-CH2.
17. Compound according to claim 15, with formula (11)
HOOC- ( CH2 ) 5-CH=CH-CN (11)
18. Compound according to claim 16, with formula (12)
R1OOC-CHR2-CHR3-CHR4-CH2-CHOH- ( CH2 ) 2~R5 ( 12 )
where R-"--R5 have the same meaning.
19. Compound with formula (13)
R1OOC-CHR2-CHR3-CHR4-(CH2)Z~CN (13) where each one of R1, R2, R3 and R4 is: alkyl, alkyl aryl, halogen, or hydroxyl; and z is 3 or 4.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/556,991 US5872267A (en) | 1993-06-15 | 1994-06-08 | Process for producing an omega-functionalized aliphatic carboxylic acid and intermediate products of said process |
| EP94920913A EP0703891B1 (en) | 1993-06-15 | 1994-06-08 | Process for producing an omega-functionalized aliphatic carboxylic acid |
| DE69414251T DE69414251T2 (en) | 1993-06-15 | 1994-06-08 | METHOD FOR PRODUCING AN OMEGA-FUNCTIONALIZED ALIPHATIC CARBONIC ACID |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93MI001273A IT1264609B1 (en) | 1993-06-15 | 1993-06-15 | PROCEDURE FOR THE PRODUCTION OF AN ALIPHATIC CARBOXYLIC ACID - FUNCTIONALIZED AND INTERMEDIATE OF THIS PROCEDURE |
| ITMI93A001273 | 1993-06-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1994029257A1 WO1994029257A1 (en) | 1994-12-22 |
| WO1994029257B1 true WO1994029257B1 (en) | 1995-02-02 |
Family
ID=11366395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1994/001865 WO1994029257A1 (en) | 1993-06-15 | 1994-06-08 | Process for producing an omega-functionalized aliphatic carboxylic acid and intermediate products of said process |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5872267A (en) |
| EP (1) | EP0703891B1 (en) |
| DE (1) | DE69414251T2 (en) |
| IT (1) | IT1264609B1 (en) |
| WO (1) | WO1994029257A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6153783A (en) * | 2000-01-06 | 2000-11-28 | Cognis Corporation | Method for preparing a difunctional aliphatic organic compound |
| FR2912741B1 (en) * | 2007-02-15 | 2012-09-21 | Arkema France | PROCESS FOR THE SYNTHESIS OF OMEGA-AMINO-ALKANOIC ACIDS |
| WO2022207923A1 (en) | 2021-04-02 | 2022-10-06 | Sce France | Substituted lactones, polymers thereof, and processes for preparing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322547A (en) * | 1980-07-21 | 1982-03-30 | Brichima S.P.A. | Process for producing difunctional aliphatic organic compounds |
-
1993
- 1993-06-15 IT IT93MI001273A patent/IT1264609B1/en active IP Right Grant
-
1994
- 1994-06-08 DE DE69414251T patent/DE69414251T2/en not_active Expired - Fee Related
- 1994-06-08 US US08/556,991 patent/US5872267A/en not_active Expired - Fee Related
- 1994-06-08 WO PCT/EP1994/001865 patent/WO1994029257A1/en active IP Right Grant
- 1994-06-08 EP EP94920913A patent/EP0703891B1/en not_active Expired - Lifetime
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