FI63961C - Foerfarande foer framstaellning av fettsyranitriler och glycerol genom anvaendning av glycerider speciellt naturliga fetter och oljor som utgaongsmaterial - Google Patents
Foerfarande foer framstaellning av fettsyranitriler och glycerol genom anvaendning av glycerider speciellt naturliga fetter och oljor som utgaongsmaterial Download PDFInfo
- Publication number
- FI63961C FI63961C FI782516A FI782516A FI63961C FI 63961 C FI63961 C FI 63961C FI 782516 A FI782516 A FI 782516A FI 782516 A FI782516 A FI 782516A FI 63961 C FI63961 C FI 63961C
- Authority
- FI
- Finland
- Prior art keywords
- reaction
- fatty acid
- glycerol
- ammonia
- temperature
- Prior art date
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 178
- 238000005057 refrigeration Methods 0.000 title description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 86
- 239000000194 fatty acid Substances 0.000 claims description 86
- 229930195729 fatty acid Natural products 0.000 claims description 86
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 77
- 238000006243 chemical reaction Methods 0.000 claims description 76
- -1 fatty acid nitriles Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 45
- 239000003054 catalyst Substances 0.000 claims description 39
- 150000004665 fatty acids Chemical class 0.000 claims description 38
- 229910021529 ammonia Inorganic materials 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000005456 glyceride group Chemical group 0.000 claims description 23
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- 150000007513 acids Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 229910052793 cadmium Inorganic materials 0.000 claims description 5
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
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- 239000010941 cobalt Substances 0.000 claims description 4
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
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- 238000000926 separation method Methods 0.000 claims description 2
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- 235000011187 glycerol Nutrition 0.000 description 55
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- 239000007789 gas Substances 0.000 description 11
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- AQQPJNOXVZFTGE-UHFFFAOYSA-N 2-octadecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O AQQPJNOXVZFTGE-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 229910001570 bauxite Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
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- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
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- YRJSLCBKZMMEPB-UHFFFAOYSA-N 2-(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CC(C)C)=CC=C21 YRJSLCBKZMMEPB-UHFFFAOYSA-N 0.000 description 1
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- QWHHBVWZZLQUIH-UHFFFAOYSA-N 2-octylbenzenesulfonic acid Chemical compound CCCCCCCCC1=CC=CC=C1S(O)(=O)=O QWHHBVWZZLQUIH-UHFFFAOYSA-N 0.000 description 1
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- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 239000000606 toothpaste Substances 0.000 description 1
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- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- JLVUSDMLNQQPCD-UHFFFAOYSA-L zinc;phenylmethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)CC1=CC=CC=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 JLVUSDMLNQQPCD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
- C07C31/225—Glycerol
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- 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)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772737607 DE2737607A1 (de) | 1977-08-20 | 1977-08-20 | Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen |
| DE2737607 | 1977-08-20 | ||
| DE2813204 | 1978-03-25 | ||
| DE19782813204 DE2813204A1 (de) | 1978-03-25 | 1978-03-25 | Verfahren zur herstellung von fettsaeurennitrilen und glycerin aus glyceriden, insbesondere aus natuerlichen fetten und oelen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782516A7 FI782516A7 (fi) | 1979-02-21 |
| FI63961B FI63961B (fi) | 1983-05-31 |
| FI63961C true FI63961C (fi) | 1983-09-12 |
Family
ID=25772581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782516A FI63961C (fi) | 1977-08-20 | 1978-08-17 | Foerfarande foer framstaellning av fettsyranitriler och glycerol genom anvaendning av glycerider speciellt naturliga fetter och oljor som utgaongsmaterial |
Country Status (36)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3131968A1 (de) * | 1981-08-13 | 1983-02-24 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von aliphatischen nitrilen |
| EP0224706A1 (de) * | 1985-11-01 | 1987-06-10 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung eines Oxazols |
| DE3639857A1 (de) * | 1986-11-21 | 1988-06-01 | Hoechst Ag | Verfahren zur herstellung von fettsaeurenitrilen und glycerin aus glyceriden |
| US6063369A (en) * | 1998-03-16 | 2000-05-16 | Alterna, Inc. | Quaternized hemp seed oil |
| MX2008011217A (es) | 2006-03-08 | 2008-09-11 | Kao Corp | Proceso para producir nitrilos alifaticos. |
| JP4972387B2 (ja) * | 2006-03-08 | 2012-07-11 | 花王株式会社 | 脂肪族ニトリルの製造方法 |
| FR2907781B1 (fr) * | 2006-10-27 | 2010-01-08 | Ceca Sa | Procede de synthese de diamines et/ou de triamines primaires de haute purete a partir d'acides dimeres ou trimeres |
| FR2916445B1 (fr) * | 2007-05-24 | 2009-07-10 | Arkema France | Procede de co-production de carbonates cycliques et de nitriles et/ou d'amines gras |
| GT200700043A (es) * | 2007-05-25 | 2008-03-03 | Biocompuestos de funcion nitrilo | |
| EP2536777B1 (de) | 2010-02-18 | 2016-04-20 | Basf Se | Polymerdispersion, die ein hochverzweigtes polycarbonat mit ungesättigten fettsäuregruppen enthält |
| EP3297431A1 (en) | 2015-05-22 | 2018-03-28 | Akzo Nobel Chemicals International B.V. | Fatty nitrile solvents for agricultural formulations |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2037389A (en) * | 1932-02-03 | 1936-04-14 | Ig Farbenindustrie Ag | Nitriles of higher unsaturated fatty acids and a process of preparing them |
| GB416631A (en) * | 1934-02-01 | 1934-09-18 | Ig Farbenindustrie Ag | Manufacture of nitriles of unsaturated fatty acids |
| GB451594A (en) * | 1935-02-05 | 1936-08-05 | Ig Farbenindustrie Ag | Improvements relating to the production of nitriles |
| GB477463A (en) * | 1935-12-09 | 1937-12-30 | Armour & Co | Improvements in process of preparing nitriles |
| FR864571A (fr) * | 1939-06-02 | 1941-04-30 | Rhone Poulenc Sa | Procédé de préparation de l'adiponitrile |
| DK78377C (da) * | 1940-10-05 | 1954-11-08 | Armour & Co | Fremgangsmåde til fremstilling af nitriler af mættede eller umættede fedtsyrer. |
| US2524831A (en) * | 1945-10-17 | 1950-10-10 | Armour & Co | Manufacture of nitriles |
| US2493637A (en) * | 1948-05-01 | 1950-01-03 | Rohm & Haas | Process for the preparation of aliphatic nitriles |
| US2589232A (en) * | 1950-03-14 | 1952-03-18 | Hercules Powder Co Ltd | Method of preparing stabilized fatty acid nitriles |
| US2794043A (en) * | 1955-01-13 | 1957-05-28 | Goodrich Co B F | Preparation of aliphatic nitriles |
| US2808426A (en) * | 1956-01-26 | 1957-10-01 | Armour & Co | Preparation of nitriles |
| US2993926A (en) * | 1957-10-30 | 1961-07-25 | Archer Daniels Midland Co | Method of preparing nitriles |
| CH494210A (de) * | 1968-03-27 | 1970-07-31 | Sandoz Ag | Verfahren zur Herstellung von Nitrilen |
| US3850974A (en) * | 1973-05-23 | 1974-11-26 | Akzona Inc | Production of nitriles |
-
1978
- 1978-08-14 IN IN889/CAL/78A patent/IN150312B/en unknown
- 1978-08-14 ES ES472553A patent/ES472553A1/es not_active Expired
- 1978-08-15 RO RO197894982A patent/RO77028A/ro unknown
- 1978-08-15 BG BG040672A patent/BG33734A3/xx unknown
- 1978-08-16 EG EG511/78A patent/EG13422A/xx active
- 1978-08-16 EP EP78100666A patent/EP0000916B1/de not_active Expired
- 1978-08-16 DD DD78207321A patent/DD138311A5/xx not_active IP Right Cessation
- 1978-08-16 DE DE7878100666T patent/DE2860715D1/de not_active Expired
- 1978-08-17 FI FI782516A patent/FI63961C/fi not_active IP Right Cessation
- 1978-08-17 YU YU01977/78A patent/YU197778A/xx unknown
- 1978-08-17 JP JP9957878A patent/JPS5441806A/ja active Granted
- 1978-08-18 AU AU39076/78A patent/AU519437B2/en not_active Expired
- 1978-08-18 CA CA000309619A patent/CA1135722A/en not_active Expired
- 1978-08-18 AT AT600778A patent/AT359991B/de not_active IP Right Cessation
- 1978-08-18 PT PT68440A patent/PT68440A/pt unknown
- 1978-08-18 AR AR273352A patent/AR218080A1/es active
- 1978-08-18 MX MX174574A patent/MX147995A/es unknown
- 1978-08-18 PH PH21508A patent/PH16609A/en unknown
- 1978-08-18 IL IL55385A patent/IL55385A/xx unknown
- 1978-08-18 IT IT26849/78A patent/IT1099021B/it active
- 1978-08-18 HU HU78HO2097A patent/HU180472B/hu unknown
- 1978-08-18 NZ NZ188179A patent/NZ188179A/xx unknown
- 1978-08-18 BR BR7805331A patent/BR7805331A/pt unknown
- 1978-08-18 SU SU782650552A patent/SU971092A3/ru active
- 1978-08-18 CS CS785425A patent/CS202509B2/cs unknown
- 1978-08-18 OA OA56581A patent/OA06038A/xx unknown
- 1978-08-18 NO NO782821A patent/NO147271C/no unknown
- 1978-08-18 IE IE1677/78A patent/IE47316B1/en unknown
- 1978-08-18 GR GR57029A patent/GR73064B/el unknown
- 1978-08-18 DK DK367978A patent/DK159064C/da not_active IP Right Cessation
- 1978-08-19 PL PL1978209133A patent/PL119196B1/pl unknown
-
1979
- 1979-04-24 US US06/032,753 patent/US4234509A/en not_active Expired - Lifetime
-
1980
- 1980-05-23 TR TR20021A patent/TR20021A/xx unknown
-
1983
- 1983-06-30 SG SG378/83A patent/SG37883G/en unknown
-
1984
- 1984-02-01 HK HK81/84A patent/HK8184A/xx unknown
-
1985
- 1985-12-30 MY MY553/85A patent/MY8500553A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: HOECHST AKTIENGESELLSCHAFT |