SU405868A1 - METHOD OF OBTAINING N-ACYLATED AMINO ACIDS - Google Patents
METHOD OF OBTAINING N-ACYLATED AMINO ACIDSInfo
- Publication number
- SU405868A1 SU405868A1 SU1373812A SU1373812A SU405868A1 SU 405868 A1 SU405868 A1 SU 405868A1 SU 1373812 A SU1373812 A SU 1373812A SU 1373812 A SU1373812 A SU 1373812A SU 405868 A1 SU405868 A1 SU 405868A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- amino acids
- obtaining
- acylated amino
- fatty acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- 150000001413 amino acids Chemical class 0.000 title description 4
- 239000002253 acid Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 238000005188 flotation Methods 0.000 description 5
- 239000003784 tall oil Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- -1 monochloroxy Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1one
Р1зобретение относитс к способу получени Ы-ад.илирова-нных аминокислот общей формулыThe invention relates to a method for producing N-ad. Or amino acids of the general formula
.0.0
CC
N-(CH)-COOH НN- (CH) -COOH H
где R - остатО)К кислот Сю-Gigwhere R is the residue O) to acids Xyu-Gig
п , используе.мых при флотации песульфидныхp used in flotation of pesulfide
рудИзвестен способ получени поверхностноактивного вещества «медиалан - продукта конденсации хлорангидрида- жлрных кислот с саркозином, вл ющегос эффективным флотореагентом . Однако указанные соединеий мало доступны, так как дл их синтеза примен ют дорогое и дефицитное сырье (олеинова кислота, кокосовое масло, саркози«), а тех.нологи производства сложна и многостадийна .The known method for the preparation of the surfactant substance "medialan - a product of condensation of acid chloride-acid acids with sarcosine, which is an effective flotation reagent. However, these compounds are scarcely available, since expensive and scarce raw materials (oleic acid, coconut oil, sarkozy) are used to synthesize them, and technical technologies of production are complex and multistage.
Предлагаемый опсх;об получени N-ацилированных аминокислот состоит IB конденсации вьющих жи рмьих кислот с «атр,певой солью ами оуксусной кислоты с последующим гидролизом и выделением целевого продукта известным способом. Реакци протекает по схеме: :. The proposed procedure for the preparation of N-acylated amino acids consists of IB condensation of essential oils of acid with apr, ammonium salt of acetic acid, followed by hydrolysis and isolation of the target product in a known manner. The reaction proceeds according to the scheme::.
КСООН -ХН СН СОО а-KCONHCH-zCOONO + H.OUNCS-XH CH COO a-KCONHCH-zCOONO + H.O
Натриевую соль аминоуксусной кислоты -получают при обработке монохлоруксуспой кислоты аммиаком с последующей нейтрализацией едким натром.Amino acetic acid sodium salt is obtained by treating monochloroxy acid with ammonia, followed by neutralization with caustic soda.
В качестве жирных кислот может быть использована жирнокис.ютна фракци таллоаого ;масла, легкое масло (нобочныи продукт переработки таллового масла) и синтетические жирные 1КИСЛОТЫ.As fatty acids, fatty acid can be used: a fraction of tall oil, light oil (butyl oil from the processing of tall oil), and synthetic fatty acids of 1 ACID.
Использованна дл синтеза жирнок-ислотла фракци таллового масла содержит 90.5% жирных кислот (кислотное число фракции 177,4).The fatty acid fraction of tall oil used for the synthesis contains 90.5% fatty acids (the acid number of the fraction is 177.4).
К нагретым до 120° С жирным кислотам таллового масла прибавл ют при перемещиБании гор чий насыщенный Водный раствор натриевой соли аминоуксусной кислоты, вз той с 20%-ным избытком (на 10 г КИслот 1,1 г аминоадетата натри ), нагревают до 195° С и выдерживают п,р,и этой температуре 3,5 час. После охлаждени получают твердый продукт ( 14 г), хорощо растворимый в воде.Fatty acids of tall oil heated to 120 ° C are added while mixing hot saturated aqueous solution of the sodium salt of aminoacetic acid taken with a 20% excess (per 10 g of acid, 1.1 g of sodium aminoadetate) is heated to 195 ° C and maintain p, p, and this temperature is 3.5 hours. After cooling, a solid (14 g), well soluble in water, is obtained.
Полученцый реагент содержит в качествеThe resulting reagent contains as
|нр.и,месей небольщое количество свободных| nr.i, mesyay a small amount of free
жирных кислот и их мыл, неактивгтые вещества , содержащиес в исходной жирнокислотной фракции, аминоацетат, хлористый натрий И продукты разложени , образовавшиес в ходе реакции. .fatty acids and their soaps, inactive substances contained in the original fatty acid fraction, amino acetate, sodium chloride AND decomposition products formed during the reaction. .
Полученный продукт получил «азвание «талацет. Содерл ание основного веидества в различных парти х талацета 45-55%.The resulting product received a "name" talacet. The content of the main story in various parties of talaceta is 45-55%.
ripiH флотации вольфрамсодержащего минерала гюбнерита из шламов, выделенных з процессе гравитац-иоаного обогащепи руды, с применением в качестве собирател талацета извлеченле трехокиси вольфрама в концентрат на 5% выше, чем при иснользоваеии олеата натри . При это качество концентрата также несколько .выше, а расход талацетата на 25% меньше, чем олеата натри .ripiH flotation of a hubnerite tungsten-containing mineral from sludge extracted from the process of gravity-ore ore dressing, using talaceta as a collector, recovered tungsten trioxide in concentrate is 5% higher than with sodium oleate. At that, the quality of the concentrate is also somewhat higher, and the consumption of talacetate is 25% less than that of sodium oleate.
При флотации хвостов магнитного обогащени л елезной руды в присутствии талацета получают концентрат того же качества, что и при иснользовании таллового масла, но коэффициент извлечени выше.During flotation of tailings of magnetic enrichment of iron ore in the presence of talaceth, concentrate of the same quality is obtained as when using tall oil, but the recovery factor is higher.
Таким образом, предлагаемый способ прост в осуществлении, основан на использовании сравнительно недорогого и доступиого сырь , получаемый реагент очень эффективен при флотации, используемый аминоадетат натри можно примен ть без очист; ,-и от при.месей хлористого натри .Thus, the proposed method is simple to implement, is based on the use of relatively inexpensive and available raw materials, the resulting reagent is very effective in flotation, the sodium aminoadetate used can be used without purification; , -and from primes of sodium chloride.
Предмет изобретен и The subject is invented and
Способ получени N-ацилированных аминокислот общей формулыThe method of obtaining N-acylated amino acids of the general formula
.«. "
CC
K-ICH J-COOH нK-ICH J-COOH n
где R - остаток жирных кислот Сю-Cig;where R is the residue of fatty acids Sue-Cig;
п 1-б, отличающийс тем, что высшие жирные кислоты конденсируют с натриевой солью а:МИноуксусной кислоты с последующим гидролизом и выделением целевого продукта известным способо.м.P1-b, characterized in that the higher fatty acids are condensed with the sodium salt of a: Minoacetic acid, followed by hydrolysis and the isolation of the target product by a known method m.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1373812A SU405868A1 (en) | 1969-10-06 | 1969-10-06 | METHOD OF OBTAINING N-ACYLATED AMINO ACIDS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1373812A SU405868A1 (en) | 1969-10-06 | 1969-10-06 | METHOD OF OBTAINING N-ACYLATED AMINO ACIDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU405868A1 true SU405868A1 (en) | 1973-11-05 |
Family
ID=20448018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1373812A SU405868A1 (en) | 1969-10-06 | 1969-10-06 | METHOD OF OBTAINING N-ACYLATED AMINO ACIDS |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU405868A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2675641C1 (en) * | 2015-03-30 | 2018-12-21 | Клариант Интернэшнл Лтд | Composition of fatty acids and n-acyl derivatives of sarcosine for improved flotation of non-sulphide minerals |
-
1969
- 1969-10-06 SU SU1373812A patent/SU405868A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2675641C1 (en) * | 2015-03-30 | 2018-12-21 | Клариант Интернэшнл Лтд | Composition of fatty acids and n-acyl derivatives of sarcosine for improved flotation of non-sulphide minerals |
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