DE1944114A1 - Verfahren zur Herstellung organischer Saeuren - Google Patents
Verfahren zur Herstellung organischer SaeurenInfo
- Publication number
- DE1944114A1 DE1944114A1 DE19691944114 DE1944114A DE1944114A1 DE 1944114 A1 DE1944114 A1 DE 1944114A1 DE 19691944114 DE19691944114 DE 19691944114 DE 1944114 A DE1944114 A DE 1944114A DE 1944114 A1 DE1944114 A1 DE 1944114A1
- Authority
- DE
- Germany
- Prior art keywords
- esters
- carboxylic acids
- hydrocarbons
- lipid extract
- solvent
- Prior art date
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000007524 organic acids Chemical class 0.000 title description 3
- 235000005985 organic acids Nutrition 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- 150000002632 lipids Chemical class 0.000 claims description 49
- 239000000284 extract Substances 0.000 claims description 33
- 229930195733 hydrocarbon Natural products 0.000 claims description 32
- 150000002430 hydrocarbons Chemical class 0.000 claims description 32
- 150000001735 carboxylic acids Chemical class 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 238000000605 extraction Methods 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000000638 solvent extraction Methods 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- 239000001963 growth medium Substances 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 54
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
- 150000007513 acids Chemical class 0.000 description 22
- 235000014113 dietary fatty acids Nutrition 0.000 description 20
- 239000000194 fatty acid Substances 0.000 description 20
- 229930195729 fatty acid Natural products 0.000 description 20
- 150000004665 fatty acids Chemical class 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 16
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 244000005700 microbiome Species 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006386 neutralization reaction Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000006136 alcoholysis reaction Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000589220 Acetobacter Species 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000235646 Cyberlindnera jadinii Species 0.000 description 2
- 241000228143 Penicillium Species 0.000 description 2
- 241000235015 Yarrowia lipolytica Species 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002195 soluble material Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 241001147825 Actinomyces sp. Species 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000186073 Arthrobacter sp. Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- 241001112695 Clostridiales Species 0.000 description 1
- 241000193171 Clostridium butyricum Species 0.000 description 1
- 241000186249 Corynebacterium sp. Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 244000285963 Kluyveromyces fragilis Species 0.000 description 1
- 235000014663 Kluyveromyces fragilis Nutrition 0.000 description 1
- 241001123676 Metschnikowia pulcherrima Species 0.000 description 1
- 241000192017 Micrococcaceae Species 0.000 description 1
- 241000191936 Micrococcus sp. Species 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000269435 Rana <genus> Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000006364 Torula Species 0.000 description 1
- 241000607365 Vibrio natriegens Species 0.000 description 1
- 241001517672 Xanthomonas axonopodis pv. begoniae Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- -1 n-heptane Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
- C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4153968 | 1968-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1944114A1 true DE1944114A1 (de) | 1970-10-22 |
Family
ID=10420165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691944114 Pending DE1944114A1 (de) | 1968-08-30 | 1969-08-30 | Verfahren zur Herstellung organischer Saeuren |
Country Status (12)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179457A (en) * | 1978-12-29 | 1979-12-18 | Eastman Kodak Company | Conversion of fatty acid esters to fatty acids |
| US9101942B2 (en) | 2009-06-16 | 2015-08-11 | Aurora Algae, Inc. | Clarification of suspensions |
| US9266973B2 (en) | 2013-03-15 | 2016-02-23 | Aurora Algae, Inc. | Systems and methods for utilizing and recovering chitosan to process biological material |
| US20140275483A1 (en) * | 2013-03-15 | 2014-09-18 | Aurora Algae, Inc. | Algal oil compositions |
-
1968
- 1968-08-30 GB GB41539/69A patent/GB1271516A/en not_active Expired
-
1969
- 1969-08-01 IE IE1082/69A patent/IE33927B1/xx unknown
- 1969-08-06 US US847942A patent/US3642844A/en not_active Expired - Lifetime
- 1969-08-27 FR FR6929352A patent/FR2019386A1/fr not_active Withdrawn
- 1969-08-27 NL NL6913071A patent/NL6913071A/xx unknown
- 1969-08-28 IT IT39684/69A patent/IT941526B/it active
- 1969-08-28 NO NO3444/69A patent/NO132937C/no unknown
- 1969-08-28 CH CH1305069A patent/CH551359A/xx not_active IP Right Cessation
- 1969-08-29 BE BE738175D patent/BE738175A/xx unknown
- 1969-08-29 AT AT827469A patent/AT289010B/de not_active IP Right Cessation
- 1969-08-29 SE SE11975/69A patent/SE369711B/xx unknown
- 1969-08-30 DE DE19691944114 patent/DE1944114A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IE33927L (en) | 1970-02-28 |
| NO132937C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-02-04 |
| GB1271516A (en) | 1972-04-19 |
| BE738175A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-03-02 |
| CH551359A (de) | 1974-07-15 |
| IE33927B1 (en) | 1974-12-11 |
| US3642844A (en) | 1972-02-15 |
| NL6913071A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-03-03 |
| SE369711B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-16 |
| AT289010B (de) | 1971-03-25 |
| IT941526B (it) | 1973-03-10 |
| FR2019386A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-07-03 |
| NO132937B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-27 |
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