US2776323A - Higher fatty alcohols - Google Patents
Higher fatty alcohols Download PDFInfo
- Publication number
- US2776323A US2776323A US2776323DA US2776323A US 2776323 A US2776323 A US 2776323A US 2776323D A US2776323D A US 2776323DA US 2776323 A US2776323 A US 2776323A
- Authority
- US
- United States
- Prior art keywords
- higher fatty
- hydrogenation
- ester
- catalyst
- fat
- 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.)
- Expired - Lifetime
Links
- 150000002191 fatty alcohols Chemical class 0.000 title claims description 19
- 238000005984 hydrogenation reaction Methods 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 description 15
- 239000003760 tallow Substances 0.000 description 12
- -1 ALCOHOL HYDROGEN Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 101000870345 Vasconcellea cundinamarcensis Cysteine proteinase 1 Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/04—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by reduction of oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- 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
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
Definitions
- Patent 1,839,974 such metals as cadmium, silver, tin and their oxides, as well as the oxides of zinc, chromium, magnesium and manganese; and the ruthenium-containing hydrogenation catalysts as described in U. S. Patent 2,607,807.
- Hydrogenation can be effected at a temperature within about the range of 400 to 700 F. and pressures within about the range of 500 to 5000 pounds, for a period of time varying from a few minutes and longer, e. g., 60 minutes, with about /2% to of catalyst based on the ester, the catalyst being suspended in the ester or employed in fixed bed over which the ester is passed.
- the fat e. g., tallow containing the ester interchange catalyst, e. g., litharge
- the higher fatty alcohol e. g., tallow alcohol produced in a subsequent step of the process, hereinafter to be shown, near the bottom.
- the ester interchange reaction occurs with the tallow alcohol distilling up the column forming glycerine and the tallow acid-tallow alcohol ester.
- reaction temperature e' g., 400 F.
- glycerine, and excess tallow alcohol are distilled into a separator where two easily separable phases of tallow alcohol and glycerine are formed, hydrogen gas being circulated through the reactor to maintain the partial pressure necessary to distill the alcohol and glycerine at the reaction temperature.
- the tallow acid-tallow alcohol ester collects at the base I interchange zone, and the ester passed into the hydrogenation zone.
- Catalyst e. g., copper chromite
- Catalyst is contacted with incoming ester and hydrogen introduced near the bottom of the hydrogenation zone, and the tallow acid-tallow alcohol ester hydrogenated under the conditions hereinabove given.
- catalyst is removed from the hydrogenation products and returned to the hydrogenation zone with any catalyst makeup.
- the hydrogenation products containing higher fatty alcohol are conducted to the ester interchange zone for use in the ester interchange reaction earlier described.
- Process for the production of higher fatty alcohols which comprises contacting a fat with a higher fatty alcohol under transesterifying conditions in a distillation zone, withdrawing an overhead fraction comprising fatty alcohol and glycerine and a bottoms fraction comprising a higher fatty alcohol ester of a fatty acid from the distillation zone, contacting the bottoms fraction with hydrogen in the presence of a hydrogenation catalyst under hydrogenating conditions in a hydrogenation zone and passing the hydrogenation reaction product into the distillation zone together with further quantities of fat.
- Process for the production of higher fatty alcohols which comprises heating a fat with a stoichiometric excess of a higher fatty alcohol in a distillation zone at a temperature between about 300 and 600 F. under reduced pressure in the presence of an ester interchange catalyst, withdrawing an overhead fraction comprising fatty alcohol and glycerine and a bottoms fraction comprising a higher fatty alcohol ester of a fatty acid from the distillation zone, contacting the bottoms fraction with a hydrogenation catalyst at elevated temperatures and pressures to produce a hydrogenation product containing the higher fatty alcohols, and passing said hydrogenation product into the distillation zone together with further quantities of fat.
- Process for the production of higher fatty alcohols which comprises contacting a fat with a higher fatty alcohol under transesterifying conditions, fractionally distilling the transesterification reaction product to separate glycerine and fatty alcohol overhead and to produce a bottoms fraction rich in fatty alcohol ester of fatty acid, contacting the bottoms fraction with hydrogen in the presence of a hydrogenation catalyst under hydrogenating conditions and then contacting at least a major proportion of the hydrogenation reaction product with further quantities of fat under transesterifying conditions.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Jan. 1, 1957 w. e. TOLAND ET AL 2,776,323
HIGHER FATTY ALCOHOLS Filed July 5, 1955 ALCOHOL HYDROGEN SEPARATOR FAT w 3 z I. CC I CATALYST 3 5 ESTER 0 INTERCHANGE J SEPARATOR U D Q g CATALYST RECYCLE Z 0 p CATALYST Z U O O (I 2 CATALYST z: HYDROGENATION HYDROGEN ,5 SEPARATOR i INVENTORS WILL/AM G. TOLAND IRVING E. LEV/NE ATTORNEYS for example in U. S. Patent 1,839,974; such metals as cadmium, silver, tin and their oxides, as well as the oxides of zinc, chromium, magnesium and manganese; and the ruthenium-containing hydrogenation catalysts as described in U. S. Patent 2,607,807.
Hydrogenation can be effected at a temperature within about the range of 400 to 700 F. and pressures within about the range of 500 to 5000 pounds, for a period of time varying from a few minutes and longer, e. g., 60 minutes, with about /2% to of catalyst based on the ester, the catalyst being suspended in the ester or employed in fixed bed over which the ester is passed.
In order to illustrate the practice of the invention reference is made to the accompanying drawing which is a schematic block diagram showing the zones of ester interchange, hydrogenation, separation and recycle of hydrogenation products and catalyst.
Referring now to the drawing, the fat, e. g., tallow containing the ester interchange catalyst, e. g., litharge, is fed to the top of the ester interchange zone, and the higher fatty alcohol, e. g., tallow alcohol produced in a subsequent step of the process, hereinafter to be shown, near the bottom. As the fat travels down the ester interchange zone, under interchange conditions hereinabove described, the ester interchange reaction occurs with the tallow alcohol distilling up the column forming glycerine and the tallow acid-tallow alcohol ester. At the reaction temperature, e' g., 400 F., glycerine, and excess tallow alcohol are distilled into a separator where two easily separable phases of tallow alcohol and glycerine are formed, hydrogen gas being circulated through the reactor to maintain the partial pressure necessary to distill the alcohol and glycerine at the reaction temperature.
The tallow acid-tallow alcohol ester collects at the base I interchange zone, and the ester passed into the hydrogenation zone. Catalyst, e. g., copper chromite, is contacted with incoming ester and hydrogen introduced near the bottom of the hydrogenation zone, and the tallow acid-tallow alcohol ester hydrogenated under the conditions hereinabove given. Following hydrogenation, catalyst is removed from the hydrogenation products and returned to the hydrogenation zone with any catalyst makeup. The hydrogenation products containing higher fatty alcohol are conducted to the ester interchange zone for use in the ester interchange reaction earlier described.
Obviously many modifications and variations of the invention, as hereinbefore set forth, may be made without departing from the spirit and scope thereof and, therefore, only such limitations should be imposed as are indicated in the appended claims.
We claim:
1. Process for the production of higher fatty alcohols which comprises contacting a fat with a higher fatty alcohol under transesterifying conditions in a distillation zone, withdrawing an overhead fraction comprising fatty alcohol and glycerine and a bottoms fraction comprising a higher fatty alcohol ester of a fatty acid from the distillation zone, contacting the bottoms fraction with hydrogen in the presence of a hydrogenation catalyst under hydrogenating conditions in a hydrogenation zone and passing the hydrogenation reaction product into the distillation zone together with further quantities of fat.
2. Process according to claim 1 wherein the hydrogenation catalyst is a copper chromite.
3. Process for the production of higher fatty alcohols which comprises heating a fat with a stoichiometric excess of a higher fatty alcohol in a distillation zone at a temperature between about 300 and 600 F. under reduced pressure in the presence of an ester interchange catalyst, withdrawing an overhead fraction comprising fatty alcohol and glycerine and a bottoms fraction comprising a higher fatty alcohol ester of a fatty acid from the distillation zone, contacting the bottoms fraction with a hydrogenation catalyst at elevated temperatures and pressures to produce a hydrogenation product containing the higher fatty alcohols, and passing said hydrogenation product into the distillation zone together with further quantities of fat.
4. Process according to claim 3 wherein the bottoms fraction is contacted with a hydrogenation catalyst at a temperature within the range of 400 F. to 700 F. and at pressure within about the range of 500 to 5000 pounds.
5. Process according to claim 4 wherein the ester interchange catalyst is litharge.
6. Process according to claim 3 wherein the hydrogenation catalyst is a copper chromite.
7. Process according to claim 6 wherein the fat is tallow.
8. Process according to claim 7 wherein the fatty alcohol and fat is introduced into the interchange zone in a mole ratio of from greater than 3 to 1 up to 7 to l.
9. Process for the production of higher fatty alcohols which comprises contacting a fat with a higher fatty alcohol under transesterifying conditions, fractionally distilling the transesterification reaction product to separate glycerine and fatty alcohol overhead and to produce a bottoms fraction rich in fatty alcohol ester of fatty acid, contacting the bottoms fraction with hydrogen in the presence of a hydrogenation catalyst under hydrogenating conditions and then contacting at least a major proportion of the hydrogenation reaction product with further quantities of fat under transesterifying conditions.
No references cited.
Claims (1)
1. PROCESS FOR THE PRODUCTION OF HIGHER FATTY ALCOHOLS WHICH COMPRISES CONTACTING A FAT WITH A HIGHER FATTY ALCOHOL UNDER TRANSESTERIFYING CONDITIONS IN A DISTILLATION ZONE, WITHDRAWING AN OVERHEAD FRACTION COMPRISING FATTY ALCOHOL AND GLYCERINE AND A BOTTOMS FRACTION COMPRISING A HIGHER FATTY ALCOHOL ESTER OF A FATTY ACID FROM THE DISTILLATION ZONE, CONTACATING THE BOTTOMS FRACTION WITH HYDROGEN IN THE PRESENCE OF A HYDROGENATION CATALYST UNDER HYDROGENATING CONDITIONS IS A HYDROGERNATION ZONE AND PASSING THE HYDROGENATION REACTAION PRODUCT INTO THE DISTILLATION ZONE TOGETHER WITH FURTHER QUANTITIES OF FAT.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2776323A true US2776323A (en) | 1957-01-01 |
Family
ID=3446261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2776323D Expired - Lifetime US2776323A (en) | Higher fatty alcohols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2776323A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3180881A (en) * | 1959-09-11 | 1965-04-27 | Ziegler Karl | Transalkylation of aluminum and boron alkyl compounds |
| US3859368A (en) * | 1971-09-08 | 1975-01-07 | Halcon International Inc | Method of producing polyhydric compounds such as ethylene glycol by disproportionation of its monoacetate |
| US3949007A (en) * | 1969-08-01 | 1976-04-06 | Bayer Aktiengesellschaft | Process for the production of primary alkenols |
| US3968175A (en) * | 1971-09-08 | 1976-07-06 | Halcon International, Inc. | Method of producing polyhydric compounds |
| US3968174A (en) * | 1971-09-08 | 1976-07-06 | Halcon International, Inc. | Method of producing polyhydric compounds |
| US5266716A (en) * | 1991-12-19 | 1993-11-30 | Bayer Aktiengesellschaft | Process for the splitting of polycarbonates |
-
0
- US US2776323D patent/US2776323A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3180881A (en) * | 1959-09-11 | 1965-04-27 | Ziegler Karl | Transalkylation of aluminum and boron alkyl compounds |
| US3949007A (en) * | 1969-08-01 | 1976-04-06 | Bayer Aktiengesellschaft | Process for the production of primary alkenols |
| US3859368A (en) * | 1971-09-08 | 1975-01-07 | Halcon International Inc | Method of producing polyhydric compounds such as ethylene glycol by disproportionation of its monoacetate |
| US3968175A (en) * | 1971-09-08 | 1976-07-06 | Halcon International, Inc. | Method of producing polyhydric compounds |
| US3968174A (en) * | 1971-09-08 | 1976-07-06 | Halcon International, Inc. | Method of producing polyhydric compounds |
| US5266716A (en) * | 1991-12-19 | 1993-11-30 | Bayer Aktiengesellschaft | Process for the splitting of polycarbonates |
| EP0547479A3 (en) * | 1991-12-19 | 1994-10-19 | Bayer Ag | Process for cracking polycarbonates |
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