SU971090A3 - Способ получени производных пирогаллола - Google Patents

Способ получени производных пирогаллола Download PDF

Info

Publication number: SU971090A3
Authority: SU; USSR - Soviet Union
Prior art keywords: sodium; pyrogallol; mixture; yield; ether
Prior art date: 1975-11-29

Application number

SU762423802A

Other languages

English (en)

Russian (ru)

Inventor

Фредерик Харрис Джон

Джеймс Магилл Барри

Джон Нидхэм Брайан

Миллер Джон

Original Assignee

Физонз Лимитед(Фирма)

Priority date (The priority date 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 date listed.)

1975-11-29

Filing date

1976-11-29

Publication date

1982-10-30

1975-11-29 Priority claimed from GB4914275A external-priority patent/GB1574413A/en

1976-11-29 Application filed by Физонз Лимитед(Фирма) filed Critical Физонз Лимитед(Фирма)

1982-10-30 Application granted granted Critical

1982-10-30 Publication of SU971090A3 publication Critical patent/SU971090A3/ru

Links

238000000034 method Methods 0.000 title claims description 15
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 56
229940079877 pyrogallol Drugs 0.000 claims description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 25
239000000047 product Substances 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 4
229920005989 resin Polymers 0.000 claims description 4
239000011347 resin Substances 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003232 pyrogallols Chemical class 0.000 claims description 3
239000000463 material Substances 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 36
239000000243 solution Substances 0.000 claims 17
239000011541 reaction mixture Substances 0.000 claims 13
238000010992 reflux Methods 0.000 claims 12
239000003054 catalyst Substances 0.000 claims 11
238000006243 chemical reaction Methods 0.000 claims 11
239000000284 extract Substances 0.000 claims 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 9
QCAHVKJGHYVLIS-UHFFFAOYSA-N 2,2,6,6-tetrachlorocyclohexan-1-one Chemical compound ClC1(Cl)CCCC(Cl)(Cl)C1=O QCAHVKJGHYVLIS-UHFFFAOYSA-N 0.000 claims 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 7
150000001450 anions Chemical class 0.000 claims 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 6
239000002253 acid Substances 0.000 claims 6
229910052938 sodium sulfate Inorganic materials 0.000 claims 6
235000011152 sodium sulphate Nutrition 0.000 claims 6
238000001816 cooling Methods 0.000 claims 5
239000012153 distilled water Substances 0.000 claims 5
239000011734 sodium Substances 0.000 claims 5
229910052708 sodium Inorganic materials 0.000 claims 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 4
229960000583 acetic acid Drugs 0.000 claims 4
239000012043 crude product Substances 0.000 claims 4
235000014113 dietary fatty acids Nutrition 0.000 claims 4
239000000194 fatty acid Substances 0.000 claims 4
229930195729 fatty acid Natural products 0.000 claims 4
229910052943 magnesium sulfate Inorganic materials 0.000 claims 4
235000019341 magnesium sulphate Nutrition 0.000 claims 4
239000012299 nitrogen atmosphere Substances 0.000 claims 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 4
239000001632 sodium acetate Substances 0.000 claims 4
235000017281 sodium acetate Nutrition 0.000 claims 4
-1 sodium citrate Chloroacetate Chemical compound 0.000 claims 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
239000007864 aqueous solution Substances 0.000 claims 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
230000007423 decrease Effects 0.000 claims 3
238000001035 drying Methods 0.000 claims 3
239000012259 ether extract Substances 0.000 claims 3
150000004665 fatty acids Chemical class 0.000 claims 3
238000001914 filtration Methods 0.000 claims 3
239000007787 solid Substances 0.000 claims 3
238000003756 stirring Methods 0.000 claims 3
239000000725 suspension Substances 0.000 claims 3
DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 claims 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
230000002378 acidificating effect Effects 0.000 claims 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
238000004458 analytical method Methods 0.000 claims 2
229960002303 citric acid monohydrate Drugs 0.000 claims 2
238000001030 gas--liquid chromatography Methods 0.000 claims 2
239000012362 glacial acetic acid Substances 0.000 claims 2
238000010438 heat treatment Methods 0.000 claims 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
ZMUXLMHSPAYBRG-UHFFFAOYSA-N 2,2,3,3-tetrachlorocyclohexan-1-one Chemical compound ClC1(Cl)CCCC(=O)C1(Cl)Cl ZMUXLMHSPAYBRG-UHFFFAOYSA-N 0.000 claims 1
MUPSHJFYQZOECB-UHFFFAOYSA-N 2,2,6,6-tetrachloro-4-methylcyclohexan-1-one Chemical compound CC1CC(Cl)(Cl)C(=O)C(Cl)(Cl)C1 MUPSHJFYQZOECB-UHFFFAOYSA-N 0.000 claims 1
MUAWWROODCFBEM-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;morpholine Chemical compound C1COCCN1.OC(=O)CC(O)(C(O)=O)CC(O)=O MUAWWROODCFBEM-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 1
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229910000831 Steel Inorganic materials 0.000 claims 1
QCGGXGCODUUTLZ-UHFFFAOYSA-N [Na].[Na].[Na].[Na] Chemical compound [Na].[Na].[Na].[Na] QCGGXGCODUUTLZ-UHFFFAOYSA-N 0.000 claims 1
230000021736 acetylation Effects 0.000 claims 1
238000006640 acetylation reaction Methods 0.000 claims 1
239000001361 adipic acid Substances 0.000 claims 1
235000011037 adipic acid Nutrition 0.000 claims 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
CHCFOMQHQIQBLZ-UHFFFAOYSA-N azane;phthalic acid Chemical compound N.N.OC(=O)C1=CC=CC=C1C(O)=O CHCFOMQHQIQBLZ-UHFFFAOYSA-N 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229960004106 citric acid Drugs 0.000 claims 1
GOMCKELMLXHYHH-UHFFFAOYSA-L dipotassium;phthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=CC=C1C([O-])=O GOMCKELMLXHYHH-UHFFFAOYSA-L 0.000 claims 1
MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 claims 1
HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 claims 1
238000004821 distillation Methods 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
238000002474 experimental method Methods 0.000 claims 1
238000000605 extraction Methods 0.000 claims 1
239000003456 ion exchange resin Substances 0.000 claims 1
229920003303 ion-exchange polymer Polymers 0.000 claims 1
239000001630 malic acid Substances 0.000 claims 1
235000011090 malic acid Nutrition 0.000 claims 1
229910000403 monosodium phosphate Inorganic materials 0.000 claims 1
235000019799 monosodium phosphate Nutrition 0.000 claims 1
ASHGTUMKRVIOLH-UHFFFAOYSA-L potassium;sodium;hydrogen phosphate Chemical compound [Na+].[K+].OP([O-])([O-])=O ASHGTUMKRVIOLH-UHFFFAOYSA-L 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
238000005070 sampling Methods 0.000 claims 1
KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 claims 1
239000001601 sodium adipate Substances 0.000 claims 1
235000011049 sodium adipate Nutrition 0.000 claims 1
235000017557 sodium bicarbonate Nutrition 0.000 claims 1
229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
239000001509 sodium citrate Substances 0.000 claims 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims 1
239000001488 sodium phosphate Substances 0.000 claims 1
229910000162 sodium phosphate Inorganic materials 0.000 claims 1
235000011008 sodium phosphates Nutrition 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
229940074404 sodium succinate Drugs 0.000 claims 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims 1
MSXHSNHNTORCAW-GGLLEASOSA-M sodium;(2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].O[C@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O MSXHSNHNTORCAW-GGLLEASOSA-M 0.000 claims 1
OESFSXYRSCBAQJ-UHFFFAOYSA-M sodium;3-carboxy-3,5-dihydroxy-5-oxopentanoate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O OESFSXYRSCBAQJ-UHFFFAOYSA-M 0.000 claims 1
QDWYPRSFEZRKDK-UHFFFAOYSA-M sodium;sulfamate Chemical compound [Na+].NS([O-])(=O)=O QDWYPRSFEZRKDK-UHFFFAOYSA-M 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
239000010959 steel Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 1
229940038773 trisodium citrate Drugs 0.000 claims 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 1
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229940074391 gallic acid Drugs 0.000 description 2
235000004515 gallic acid Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 1
CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
239000001648 tannin Substances 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU762423802A 1975-11-29 1976-11-29 Способ получени производных пирогаллола SU971090A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4914275A GB1574413A (en)	1975-11-29	1975-11-29	Preparation of pyrogallol compound
GB3200776		1976-07-31

Publications (1)

Publication Number	Publication Date
SU971090A3 true SU971090A3 (ru)	1982-10-30

Family

ID=26261176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU762423802A SU971090A3 (ru)	1975-11-29	1976-11-29	Способ получени производных пирогаллола

Country Status (2)

Country	Link
AT (1)	AT348504B (de)
SU (1)	SU971090A3 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2568121C1 (ru) *	2014-10-27	2015-11-10	Федеральное государственное казенное военное образовательное учреждение высшего профессионального образования "Военный учебно-научный центр Военно-воздушных сил "Военно-воздушная академия имени профессора Н.Е. Жуковского и Ю.А. Гагарина" (г. Воронеж) Министерства обороны Российской Федерации	Способ концентрирования пирогаллола из водных растворов

1976
- 1976-11-26 AT AT877276A patent/AT348504B/de not_active IP Right Cessation
- 1976-11-29 SU SU762423802A patent/SU971090A3/ru active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2568121C1 (ru) *	2014-10-27	2015-11-10	Федеральное государственное казенное военное образовательное учреждение высшего профессионального образования "Военный учебно-научный центр Военно-воздушных сил "Военно-воздушная академия имени профессора Н.Е. Жуковского и Ю.А. Гагарина" (г. Воронеж) Министерства обороны Российской Федерации	Способ концентрирования пирогаллола из водных растворов

Also Published As

Publication number	Publication date
AT348504B (de)	1979-02-26
ATA877276A (de)	1978-07-15

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SU971090A3 - Способ получени производных пирогаллола - Google Patents

Info

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Applications Claiming Priority (2)

Publications (1)

Family

ID=26261176

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

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