SU1348334A1 - Способ получени коричной кислоты - Google Patents
Способ получени коричной кислоты Download PDFInfo
- Publication number
- SU1348334A1 SU1348334A1 SU857773897A SU7773897A SU1348334A1 SU 1348334 A1 SU1348334 A1 SU 1348334A1 SU 857773897 A SU857773897 A SU 857773897A SU 7773897 A SU7773897 A SU 7773897A SU 1348334 A1 SU1348334 A1 SU 1348334A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- tetrachloro
- mixture
- phenylpropane
- formic
- Prior art date
Links
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title claims abstract description 38
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 title claims abstract description 38
- 229930016911 cinnamic acid Natural products 0.000 title claims abstract description 38
- 235000013985 cinnamic acid Nutrition 0.000 title claims abstract description 38
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 69
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 19
- JJRCOEWDFJHOFK-UHFFFAOYSA-N 1,3,3,3-tetrachloropropylbenzene Chemical compound ClC(Cl)(Cl)CC(Cl)C1=CC=CC=C1 JJRCOEWDFJHOFK-UHFFFAOYSA-N 0.000 claims abstract description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000019253 formic acid Nutrition 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 229960000583 acetic acid Drugs 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000005341 cation exchange Methods 0.000 claims 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 239000001294 propane Substances 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 abstract description 8
- 239000003729 cation exchange resin Substances 0.000 abstract description 8
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000003684 Perkin reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 cinnamic acid (3-phenylphenol) Chemical compound 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YMASWACISOOZGG-UHFFFAOYSA-N dimethyl benzene-1,4-dicarboxylate;ethane-1,2-diol Chemical compound OCCO.COC(=O)C1=CC=C(C(=O)OC)C=C1 YMASWACISOOZGG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical class [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS845410A CS241246B1 (en) | 1984-07-12 | 1984-07-12 | Method of cinnamic acid production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1348334A1 true SU1348334A1 (ru) | 1987-10-30 |
Family
ID=5398949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU857773897A SU1348334A1 (ru) | 1984-07-12 | 1985-07-03 | Способ получени коричной кислоты |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100341835C (zh) * | 2005-10-12 | 2007-10-10 | 浙江大学 | 肉桂酸的制备方法 |
| US8608970B2 (en) | 2010-07-23 | 2013-12-17 | Red Shield Acquisition, LLC | System and method for conditioning a hardwood pulp liquid hydrolysate |
| US9228243B2 (en) | 2011-08-24 | 2016-01-05 | Red Shield Acquistion, LLC | System and method for conditioning a hardwood pulp liquid hydrolysate |
| CN102584564B (zh) * | 2012-01-11 | 2015-05-27 | 巨化集团公司 | 一种肉桂酸的制备方法 |
| CN109824490A (zh) * | 2019-02-13 | 2019-05-31 | 上海拜乐新材料科技有限公司 | 一种肉桂醛及其衍生物的制备方法 |
-
1984
- 1984-07-12 CS CS845410A patent/CS241246B1/cs unknown
-
1985
- 1985-06-25 DD DD85277695A patent/DD255046A3/de not_active IP Right Cessation
- 1985-06-25 BG BG70838A patent/BG46525A1/xx unknown
- 1985-07-03 SU SU857773897A patent/SU1348334A1/ru active
- 1985-07-04 CH CH2883/85A patent/CH665630A5/de not_active IP Right Cessation
- 1985-07-08 NL NL8501954A patent/NL8501954A/nl not_active Application Discontinuation
- 1985-07-09 DE DE19853524475 patent/DE3524475A1/de active Granted
- 1985-07-11 IT IT21530/85A patent/IT1186755B/it active
- 1985-07-12 JP JP60152568A patent/JPS6169741A/ja active Pending
-
1987
- 1987-06-04 US US07/058,610 patent/US4806681A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3524475A1 (de) | 1986-01-23 |
| CH665630A5 (de) | 1988-05-31 |
| US4806681A (en) | 1989-02-21 |
| DE3524475C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-08-23 |
| CS241246B1 (en) | 1986-03-13 |
| BG46525A1 (en) | 1990-01-15 |
| IT1186755B (it) | 1987-12-16 |
| JPS6169741A (ja) | 1986-04-10 |
| DD255046A3 (de) | 1988-03-23 |
| CS541084A1 (en) | 1985-07-16 |
| NL8501954A (nl) | 1986-02-03 |
| IT8521530A0 (it) | 1985-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1348334A1 (ru) | Способ получени коричной кислоты | |
| EP0432910B1 (en) | Process for producing highly pure 2, 6 naphthalene dicarboxylic acid | |
| JP3538439B2 (ja) | テトラフルオロフタル酸および／またはテトラフルオロフタル酸無水物の製造方法 | |
| JPS5925779B2 (ja) | 立体異性脂環ジアミンの異性化法 | |
| CN109293631B (zh) | 3-氨基-n-(2，6-二氧代-3-哌啶基)-邻苯二甲酰亚胺化合物的制备方法 | |
| US4797497A (en) | Trimellitic anhydride purification process | |
| JP4074356B2 (ja) | ハロゲン化芳香族カルボン酸の脱カルボキシル化法 | |
| NZ204976A (en) | Preparation of n-formyl-l-aspartic acid anhydride | |
| JP3220508B2 (ja) | ２，３，４，５−テトラフルオロ安息香酸の製造方法 | |
| JPS59116285A (ja) | １５−ハロ−ｅ−ホモエブルナン誘導体およびその製造方法 | |
| US5233085A (en) | Preparation of 2,4,5-trifluorobenzoic acid by decarboxylation of 3,4,6-trifluorophthalic acid | |
| SU1728228A1 (ru) | Способ получени 9,9-бис/4-аминофенил/-флуорена | |
| KR100235373B1 (ko) | 이소인돌리논 유도체의 광학 이성질체 제조 방법 | |
| GB1561464A (en) | Oxidation of alkaryl compounds | |
| US1953231A (en) | Production of monocarboxylic acids and their derivatives | |
| SU282310A1 (ru) | Способ получения арол^атических три- или тетракарбоновых кислот | |
| US2878281A (en) | Preparation of amino benzoic acids | |
| JPS6238346B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH10273475A (ja) | ３−ヒドロキシ−２−メチル安息香酸及び３−アセトキシ−２−メチル安息香酸の製造方法 | |
| JPH09151160A (ja) | 単環芳香族カルボン酸の精製方法 | |
| JPS6112644A (ja) | 随時核に置換基をもつケイ皮酸類の合成法 | |
| DE19624604A1 (de) | Verfahren zur Herstellung chiraler, nicht racemischer (4-Aryl-2,5-dioxoimidazolidin-1-yl)essigsäuren | |
| JPS59128350A (ja) | １，２，３，４−ブタンテトラカルボン酸の精製法 | |
| EP0465974A1 (en) | Preparation of D-histidine and derivatives thereof from L-histidine | |
| SU810665A1 (ru) | Способ получени изо- и терефта-лЕВОй КиСлОТ |