WO2014021707A1 - A process to produce hydrazide derivatives - Google Patents
A process to produce hydrazide derivatives Download PDFInfo
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- WO2014021707A1 WO2014021707A1 PCT/MY2013/000142 MY2013000142W WO2014021707A1 WO 2014021707 A1 WO2014021707 A1 WO 2014021707A1 MY 2013000142 W MY2013000142 W MY 2013000142W WO 2014021707 A1 WO2014021707 A1 WO 2014021707A1
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- WO
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- Prior art keywords
- oil
- hydrazide
- mixture
- conducted
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000002244 precipitate Substances 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 14
- 239000000376 reactant Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical class NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 19
- 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 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001266 acyl halides Chemical class 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 claims description 4
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 239000000828 canola oil Substances 0.000 claims description 2
- 235000019519 canola oil Nutrition 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000021323 fish oil Nutrition 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- 239000002383 tung oil Substances 0.000 claims description 2
- 125000003651 hexanedioyl group Chemical group C(CCCCC(=O)*)(=O)* 0.000 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 11
- 239000008158 vegetable oil Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229940023462 paste product Drugs 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 108010048733 Lipozyme Proteins 0.000 description 2
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000935 solvent evaporation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000000854 inhibitional effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- UMSPFLJZBBTPKA-SUJAAXHWSA-N methyl (1s,2r,4as,8ar)-2-[(2r)-2-hydroxybutyl]-3-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Chemical compound C1CCC[C@@H]2C=C(C)[C@H](C[C@H](O)CC)[C@@H](C(=O)OC)[C@@H]21 UMSPFLJZBBTPKA-SUJAAXHWSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a process to produce hydrazide derivatives wherein the process includes steps of dissolving hydrazide in a solvent to form a mixture, stirring the mixture, adding a reactant, allowing reaction in the mixture to form hydrazide derivatives, allowing formation of solid precipitate and separating the solid precipitate from the mixture.
Description
A PROCESS TO PRODUCE HYDRAZIDE DERIVATIVES
FIELD OF INVENTION
The present invention relates to a process to produce hydrazide derivatives.
BACKGROUND OF INVENTION
In recent years, emphasis on a variety of hyrazide derivatives has increased due to diverse applications in pharmaceutical products, detergent as well as in oil and gas industries. Toliwal et al. in 2009 reported that triazole derivatives obtainable from hydrazide exhibit corrosion inhibition, antibacterial and insecticidal activities. Most of corrosion inhibitors are generally toxic and generate health hazards. In 2008, Shanbhag and co-workers found that hydrazide derivatives with heterocyclic compounds are nontoxic as corrosion inhibitor. Various ways have been employed in the past to synthesize hydrazide derivatives. US Patent No.5300688 and US Patent No.4985461 taught methods to produce hydrazide derivatives using volatile chemical compounds as starting sources. However, these methods disclosed a drawback which is not conducive for the environment. Efforts for a better and more eco-friendly way of producing hydrazide derivatives are being amplified, for example, using a source from vegetable oils.
Accordingly, a need still exists for a process to produce hydrazide derivatives from reaction of hydrazides of vegetable oils with acyl halides for a use as corrosion inhibitors and anti-friction.
SUMMARY OF INVENTION
The present invention relates to a process to produce hydrazide derivatives from reaction of hydrazides of vegetable oils with acyl halides, particularly for a use as corrosion inhibitors and anti-friction.
The present invention provides a process to produce hydrazide derivatives wherein the process includes steps of:
i) dissolving hydrazide in a solvent to form a mixture;
ii) stirring the mixture;
iii) adding a reactant into the mixture;
iv) allowing reaction in the mixture to form hydrazide derivatives;
v) allowing formation of solid precipitate containing hydrazide
derivatives; and
vi) separating the solid precipitate from the mixture.
These and other objects of the present invention will become more readily apparent from the detailed description given hereafter. However, it should be understood that while embodiments and examples of the present invention have been illustrated and described, it is not intended that these embodiments and examples illustrate and describe all possible forms of the present invention. Rather, words used in the specification are words of description rather than limitation and various changes may be made without departing from the scope of the invention.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
It should be noted that the following detailed description is directed to a process for producing hydrazide derivatives. More particularly, an object of the present invention is to provide a process for producing hydrazide derivatives, for example, adipoyi di-fatty hydrazide, from reaction of hydrazides of vegetable oil and acyl halides in organic solvent.
Firstly hydrazide was dissolved in organic solvent medium. The organic solvent can be polar or non polar. Preferably, the organic solvent used in invention is chloroform in a ratio of 1 :150 (w/v). Next, the mixture of hydrazide in the organic solvent is stirred at a temperature ranging from 20°C to 27°C and for a period from 1 hour to 3 hours. Then, following step was adding a reactant into the mixture to allow reaction forming hydrazide derivatives. The mixture is then stirred at a temperature ranging from 20 "C to 27 °C and for a period from 5 to 30 minutes to allow formation of solid precipitate containing hydrazide derivatives. Lastly, filtration was conducted to separate the solid precipitate from the mixture.
Hydrazides made from oil or fat can be employed in the disclosed process for producing the hydrazide derivatives. For example, hydrazide made from palm oil, palm olein, palm stearin, soybean oil, coconut oil, groundnut oil, safflower oil, linseed oil, corn oil, sunflower oil, olive oil, canola oil, cottonseed oil, rapeseed oil, tung oil, fish oil, lard, tallow and any derivatives thereof such as fatty acid methyl ester. Preferably, hydrazides were synthesized from refined, bleached and deodorized (RBD) palm olein and hydrazine monohydrate at pH 12 by way of enzymatic route as taught in the Malaysian patent application PI 201 1005479.
In another embodiment, hydrazide used in the invention was produced by reacting refined bleached and deodorized palm olein with hydrazine monohydrate at pH 12 using an enzymatic route. Alternatively, hydrazide can be obtained from the market commercially.
The reactant used in the invention is preferably, but not limiting to, acid chloride or acid dichloride. Typically, the acid chloride or acid dichloride used in this invention includes adipoyi dichloride, terephthaloyl dichloride, hexanoyl chloride and octanoyl chloride. Reaction is carried out at room temperature and mole ratio of hydrazide of vegetable oil to acid chloride is preferably 1 :1 or hydrazide of vegetable oil to acid dichloride is 1 :0.5.
The following examples further illustrate but by no means limit the scope of present invention:
Example 1: RBD palm olein
100 g of RBD palm olein was discharged into 2-L jacketed glass reactor (equipped with a circulating water bath to control temperature, a chiller and condenser to prevent solvent evaporation and a thermocouple to monitor temperature of the reaction) containing 400 mL of n-hexane. Accordingly, 122.5 g of hydrazine monohydrate at pH 12 was added into the reactor. The temperature of the mixture was set at 40°C. Once the temperature of the mixture reached the set temperature, the desired amount of enzyme (Lipozyme RMIM) was added into the reaction mixture. The stirring speed was set at 400 rpm and the reaction was run for 20 hours. After 20 hours of reaction, a white milky paste was discharged from the reactor. A 1 -L beaker containing the discharged product was heated at 60 to 80°C in the presence of ethanol to separate the product from the enzyme. A hot liquid mixture was left to cool for at least three hours at ambient temperature at 28°C for crystallization process. Finally, a white paste product was formed. Before drying under vacuum, about 300 to 400 mL of ethanol was added into the white paste product to ease filtration process. After drying, a white-solid hydrazide is obtained. The conversion of fatty acid to fatty hydrazide is 99%.
Example 2: Soya bean oil 100 g of soya bean oil was discharged into 2-L jacketed glass reactor (equipped with a circulating water bath to control temperature, a chiller and condenser to prevent solvent evaporation and a thermocouple to monitor temperature of the reaction) containing 400 mL of n-hexane. Accordingly, 1 12.3 g of hydrazine monohydrate was added into the reactor. The temperature of the mixture was set at 40°C. Once the temperature of the mixture reached the set temperature, the desired amount of enzyme (Lipozyme RMIM) was added into the reaction mixture. The stirring speed was set at 400 rpm and the reaction was run for 20 hours. After 20 hours of reaction, a white milky paste was discharged from the reactor. A 1 -L beaker containing the discharged product was heated at 60 to 80°C in the presence of ethanol to separate the product from the enzyme. A hot liquid mixture was left to cool for at least three hours at ambient temperature (28°C) for crystallization process. Finally, a white paste product was formed. Before drying under
vacuum, about 300 to 400 mL of ethanol was added into the white paste product to ease filtration process. After drying, a white-solid hydrazide is obtained. The conversion of fatty acid to fatty hydrazide is 97%.
Example 3: Adipoyl dichloride
Hydrazide of RBD palm olein (0.56 g, 2.0 mmol) was charged into 250 ml reaction vessel and chloroform (84 ml) was charged into the same vessel. The hydrazide of vegetable oil was dissolved in chloroform or hexane, and the mixture was stirred throughout the reaction. The reaction temperature was kept at room temperature (25°C). Adipoyl dichloride (0.15 ml, 1 .0 mmol) was added into the reaction mixture. The reaction mixture was stirred for 30 minutes at room temperature. After 30 minutes, some precipitates formed were filtered off. The collected weight of the precipitates was 0.72 g and percentage of yield was 63%. The product was an off-white solid at room temperature.
Example 4: Terephthaloyl dichloride Hydrazide of RBD palm olein (0.56 g, 2.0 mmol) was charged into 250 ml reaction vessel and chloroform (84 ml) was charged into the same vessel. The hydrazide of vegetable oil was dissolved in chloroform or hexane, and the mixture was stirred throughout the reaction. The reaction temperature was kept at room temperature (25°C). Terephthaloyl dichloride (0.20 g, 1 .0 mmol) was added into the reaction mixture. The reaction mixture was stirred for 30 minutes at room temperature. After 30 minutes, some precipitates formed were filtered off. The collected weight of the precipitates was 0.70 g and percentage of yield was 53%. The product was an off-white solid at room temperature.
Example 5: Hexanoyl chloride
Hydrazide of RBD palm olein (0.56 g, 2.0 mmol) was charged into 250 ml reaction vessel and chloroform (84 ml) was charged into the same vessel. The hydrazide of vegetable oil was dissolved in chloroform or hexane, and the mixture was stirred throughout the reaction. The reaction temperature was kept at room temperature (25°C). Hexanoyl chloride (0.28 ml, 2.0 mmol) was added into the reaction mixture. The reaction mixture
was stirred for 30 minutes at room temperature. After 30 minutes, some precipitates formed were filtered off. The collected weight of the precipitates was 0.49 g and percentage of yield was 36%. The product was an off-white solid at room temperature.
Example 6: Octanoyl chloride
Hydrazide of vegetable oil RBD palm olein (0.56 g, 2.0 mmol) was charged into 250 ml reaction vessel and chloroform (84 ml) was charged into the same vessel. The hydrazide of vegetable oil was dissolved in chloroform or hexane, and the mixture was stirred throughout the reaction. The reaction temperature was kept at room temperature (25°C). Octanoyl chloride (0.35 ml, 2.0 mmol) was added into the reaction mixture. The reaction mixture was stirred for 30 minutes at room temperature. After 30 minutes, some precipitates formed were filtered off. The collected weight of the precipitates was 0.58 g and percentage of yield was 65%. The product was an off-white solid at room temperature.
While embodiments and examples of the present invention have been illustrated and described, it is not intended that these embodiments and examples illustrate and describe all possible forms of the present invention. Rather, words used in the specification are words of description rather than limitation and various changes may be made without departing from the scope of the invention.
Claims
1. A process to produce hydrazide derivatives wherein the process includes steps of: i) dissolving hydrazide in a solvent to form a mixture;
ii) stirring the mixture;
iii) adding a reactant into the mixture;
iv) allowing reaction in the mixture to form hydrazide derivatives;
v) allowing formation of solid precipitate containing hydrazide derivatives; and vi) separating the solid precipitate from the mixture.
2. A process as claimed in claim 1 wherein the hydrazide in step (i) is obtained from palm oil, palm olein, palm stearin, soybean oil, coconut oil, groundnut oil, safflower oil, linseed oil, corn oil, sunflower oil, olive oil, canola oil, cottonseed oil, rapeseed oil, tung oil, fish oil, lard, tallow, or any of the combination thereof.
3. A process as claimed in claim 1 wherein the solvent in step (i) is an organic solvent.
A process as claimed in claim 3 wherein the organic solvent includes chloroform or hexane.
A process as claimed in claim 1 wherein step (i) is conducted at a ratio of 1 :150 (w/v).
A process as claimed in claim 1 wherein step (ii) is conducted at a temperature ranging from 20 °C to 27 °C and for a period from 1 hour to 3 hours.
A process as claimed in claim 1 wherein the reactant in step (iii) is an acyl halide.
A process as claimed in claim 7 wherein the acyl halide includes acid chloride acid dichloride.
9. A process as claimed in claim 8 wherein the acid chloride or acid dichioride includes adipoyl dichioride, terephthaloyl dichioride, hexanoyl chloride or octanoyl chloride.
10. A process as claimed in claim 1 wherein step (iii) is conducted at a mole ratio of 1 :1 of hydrazide and acid chloride or at a mole ratio of 1 :0.5 of hydrazide and acid dichioride.
11. A process as claimed in claim 1 wherein step (v) is conducted at a temperature ranging from 20 °C to 27Ό and for a period from 5 to 30 minutes.
12. A process as claimed in claim 1 wherein step (vi) is conducted using filtration.
13. A hydrazide derivative product as claimed in claims 1-12.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MYPI2012003471 | 2012-07-31 | ||
| MYPI2012003471 | 2012-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2014021707A1 true WO2014021707A1 (en) | 2014-02-06 |
Family
ID=50028292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/MY2013/000142 WO2014021707A1 (en) | 2012-07-31 | 2013-07-31 | A process to produce hydrazide derivatives |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2014021707A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4229463A (en) * | 1978-02-27 | 1980-10-21 | Sandoz, Inc. | Unsaturated fatty acid hydrazides |
-
2013
- 2013-07-31 WO PCT/MY2013/000142 patent/WO2014021707A1/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4229463A (en) * | 1978-02-27 | 1980-10-21 | Sandoz, Inc. | Unsaturated fatty acid hydrazides |
Non-Patent Citations (3)
| Title |
|---|
| EMAD A. JAFFAR AL-MULLA ET AL.: "Synthesis, Characterization and Optimum Reaction Conditions of Fatty Hydrazide from Triacylglycerides", RES. J. APPLIED SCI., vol. 3, no. 8, 2008, pages 545 - 549 * |
| MOHAMAD, S. ET AL.: "Enzymatic synthesis of fatty hydrazides from palm oils", J. OLEO. SCI., vol. 57, no. 5, 2008, pages 263 - 267 * |
| SONNTAG, NORMAN 0. V.: "Reactions of fatty acid chlorides: II. Synthesis of monohydrazides or dihydrazides by acylation of hydrazine hydrate with saturated fatty acid chlorides", THE JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 45, 1968, pages 571 - 574 * |
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