SU690010A1 - Method of preparing disodium salt of 1-carboxy-8-heptadecen-11-ylsulfuric acid - Google Patents
Method of preparing disodium salt of 1-carboxy-8-heptadecen-11-ylsulfuric acidInfo
- Publication number
- SU690010A1 SU690010A1 SU782569955A SU2569955A SU690010A1 SU 690010 A1 SU690010 A1 SU 690010A1 SU 782569955 A SU782569955 A SU 782569955A SU 2569955 A SU2569955 A SU 2569955A SU 690010 A1 SU690010 A1 SU 690010A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- sulfuric acid
- thionyl chloride
- sulfation
- reaction
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 title description 5
- CYKFQSXTIVGYDT-UHFFFAOYSA-N 12-sulfooxyoctadec-9-enoic acid Chemical compound CCCCCCC(OS(O)(=O)=O)CC=CCCCCCCCC(O)=O CYKFQSXTIVGYDT-UHFFFAOYSA-N 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 18
- 229960003656 ricinoleic acid Drugs 0.000 claims description 5
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- 238000005670 sulfation reaction Methods 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000012024 dehydrating agents Substances 0.000 claims 3
- 230000019635 sulfation Effects 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004359 castor oil Substances 0.000 claims 2
- 235000019438 castor oil Nutrition 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 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 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 238000013021 overheating Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000012047 saturated solution Substances 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 210000004885 white matter Anatomy 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1one
Изобретени.е .относитс к усовершенствованному способу получени динатриевой соли 1-карбокси-о-гептадецен-11 -илсерной кислоты, котора находит применение в качестве поверхностно-активного вещества.The invention relates to an improved process for the preparation of the disodium salt of 1-carboxy-o-heptadecene-11 -yl sulfuric acid, which is used as a surfactant.
Известны различные способы получени динатриевой соли 1-карбокси-8-гептадецен-11-илсерной кислоты, например путем сульфатировани рицинолевой кислоты или ее триглицерйда серным ангидридом 1, олеумом 2 или комплексом серного ангидрида с пиридином t3.Various methods are known for the preparation of the disodium salt of 1-carboxy-8-heptadecen-11-yl-sulfuric acid, for example, by sulfating ricinoleic acid or its triglyceride with sulfuric anhydride 1, oleum 2, or a complex of sulfuric anhydride with pyridine t3.
К предлагаемому способу наиболее близок способ получени динатриевой соли 1-карбокси-8-гептадецен-11-илсерной кислоты, заключающийс в том, что рицинолевую кислоту или ее триглицерид подвергают взаимодействию с концентрированной серной кислотой в присутствии уксусного ангидрида в качестве водоотнимающего средства при температуре от О до 5°С с последующей нейтрализацией щелочью 4.The method of obtaining the disodium salt of 1-carboxy-8-heptadecene-11-yl-sulfuric acid is the closest to the proposed method, in which ricinoleic acid or its triglyceride is reacted with concentrated sulfuric acid in the presence of acetic anhydride as a water removing agent at a temperature from 0 to 5 ° C, followed by neutralization with alkali 4.
Недостатком этого способа вл етс относительно невысокое качество целевого продукта; обусловленное присутствием в нем продуктов осмолени и ацетата натри .The disadvantage of this method is the relatively low quality of the target product; due to the presence of the products of tar and sodium acetate.
Цель изобретени - повышение степени чистоты целевого продукта.The purpose of the invention is to increase the purity of the target product.
Цель достигаетс описываемым способом получени динатриевой соли 1-к .арбокси-8-гептадецен-11 -илсерной кислоты, заключающимс в том, что рицинолевую кислоту или ее триглицерид .подвергают взаимодействию с концентрированной серной кислотой в присутствии хлористого тионила в качестве водоотнимающего средства при температуре от О до 5°С с последующей нейтрализацией щелочью.The goal is achieved by the described method for preparing 1-k disodium salt of arboxy-8-heptadecene-11-sulfuric acid, which means that ricinoleic acid or its triglyceride is reacted with concentrated sulfuric acid in the presence of thionyl chloride as a draining agent at a temperature from About to 5 ° C, followed by neutralization with alkali.
Отличительным признаком способа вл етс использование в качестве водоотнимающего средства хлористого тионила.A distinctive feature of the method is the use of thionyl chloride as a dewatering agent.
Процесс предпочтительно провод т при эквимол рном соотношении серной кислоты и хлористого тионила и соотношении объемных скоростей сернойкислоты и хлористого тионила 1:1,5.The process is preferably carried out at an equimolar ratio of sulfuric acid and thionyl chloride and a ratio of volume rates of sulfuric acid and thionyl chloride to 1: 1.5.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782569955A SU690010A1 (en) | 1978-01-18 | 1978-01-18 | Method of preparing disodium salt of 1-carboxy-8-heptadecen-11-ylsulfuric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782569955A SU690010A1 (en) | 1978-01-18 | 1978-01-18 | Method of preparing disodium salt of 1-carboxy-8-heptadecen-11-ylsulfuric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU690010A1 true SU690010A1 (en) | 1979-10-05 |
Family
ID=20744619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782569955A SU690010A1 (en) | 1978-01-18 | 1978-01-18 | Method of preparing disodium salt of 1-carboxy-8-heptadecen-11-ylsulfuric acid |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU690010A1 (en) |
-
1978
- 1978-01-18 SU SU782569955A patent/SU690010A1/en active
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