CN109574825A - A kind of synthetic method of phenylacetic acid - Google Patents
A kind of synthetic method of phenylacetic acid Download PDFInfo
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- CN109574825A CN109574825A CN201811610433.3A CN201811610433A CN109574825A CN 109574825 A CN109574825 A CN 109574825A CN 201811610433 A CN201811610433 A CN 201811610433A CN 109574825 A CN109574825 A CN 109574825A
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- Prior art keywords
- acid
- reaction
- phenylacetic acid
- benzene
- added
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 167
- 229960003424 phenylacetic acid Drugs 0.000 title claims abstract description 83
- 239000003279 phenylacetic acid Substances 0.000 title claims abstract description 82
- 238000010189 synthetic method Methods 0.000 title claims abstract description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 231
- 238000006243 chemical reaction Methods 0.000 claims abstract description 95
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000010791 quenching Methods 0.000 claims abstract description 29
- 230000000171 quenching effect Effects 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 21
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 11
- 239000002841 Lewis acid Substances 0.000 claims abstract description 9
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 9
- 230000020477 pH reduction Effects 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000004519 grease Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 238000007171 acid catalysis Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 13
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 4
- 231100000614 poison Toxicity 0.000 abstract description 3
- 230000007096 poisonous effect Effects 0.000 abstract description 3
- 239000012043 crude product Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 23
- 238000004064 recycling Methods 0.000 description 18
- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 239000002826 coolant Substances 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- 230000001376 precipitating effect Effects 0.000 description 16
- 238000013517 stratification Methods 0.000 description 16
- 238000005292 vacuum distillation Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000010813 municipal solid waste Substances 0.000 description 12
- 238000002390 rotary evaporation Methods 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 2
- 231100000004 severe toxicity Toxicity 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- AWDSCPCHQFTJQT-UHFFFAOYSA-N 3-oxo-2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C=O)C1=CC=CC=C1 AWDSCPCHQFTJQT-UHFFFAOYSA-N 0.000 description 1
- SBQPDLGIWJRKBS-UHFFFAOYSA-N 4-methyl-1,3-dihydroimidazole-2-thione Chemical class CC1=CNC(S)=N1 SBQPDLGIWJRKBS-UHFFFAOYSA-N 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241001284615 Frangula californica Species 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 235000004433 Simmondsia californica Nutrition 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- MYDAKBBSKFKUKP-UHFFFAOYSA-N acetonitrile;phenol Chemical compound CC#N.OC1=CC=CC=C1 MYDAKBBSKFKUKP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- YXKTVDFXDRQTKV-HNNXBMFYSA-N benzphetamine Chemical compound C([C@H](C)N(C)CC=1C=CC=CC=1)C1=CC=CC=C1 YXKTVDFXDRQTKV-HNNXBMFYSA-N 0.000 description 1
- 229960002837 benzphetamine Drugs 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229940105305 carbon monoxide Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- QMMTZDCUCDXHEW-UHFFFAOYSA-N chloromethylbenzene;formic acid Chemical compound OC=O.ClCC1=CC=CC=C1 QMMTZDCUCDXHEW-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- XHOJAWVAWFHGHL-UHFFFAOYSA-N lorcainide Chemical compound C1CN(C(C)C)CCC1N(C=1C=CC(Cl)=CC=1)C(=O)CC1=CC=CC=C1 XHOJAWVAWFHGHL-UHFFFAOYSA-N 0.000 description 1
- 229960001074 lorcainide Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 1
- 229960004719 nandrolone Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect 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
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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)
Abstract
The invention discloses a kind of synthetic methods of phenylacetic acid: be (25 ~ 5) by mass ratio: 1 benzene and glycolide or oligoglycolic acid is under 1.0 ~ 1.3 times of amount of oxygen acetyl group substance of Lewis acid catalysis; react the h of 1 h ~ 24 at 35 DEG C ~ 80 DEG C of temperature, through with water quenching reaction, inorganic acid acidification is added, grease is mutually layered, solvent is evaporated off and is dry after phenylacetic acid product.The severe poisonous chemicals such as hydrogen cyanide and carbon monoxide are neither selected in the present invention, to eliminate Product Safety doubt caused by micro or trace raw material remnants；Do not use high reaction pressure condition without using high pressure reactor again, to improve the safety of production process；The raw materials used in the present invention biological degradability is good and green safe simultaneously, and synthetic reaction Atom economy is high, good economy performance.
Description
Technical field
The present invention relates to a kind of synthetic methods of phenylacetic acid, the i.e. selective Fu Ke alkane of benzene and glycolide or oligoglycolic acid
Glycosylation reaction synthesizes phenylacetic acid, belongs to organic compound synthesis technical field.
Background technique
Phenylacetic acid is synthesis somnifacient luminal, anticonvulsive drug U.S. plain woods, cardiovascular drug methyl mercapto imidazoles, antirheumatic drug first
Base amphetamine, anorectic benzphetamine, anti-rhythm of the heart medicine Lorcainide, hypolipidemic atorvastatin, anticholinergic agent atropine medicine
The important intermediate and fermentation method of object and hormone cortisol phenylacetic acid nandrolone produce the important substrate of penicillin, and close
At the important intermediate of insecticide phenthoate dimephenthoate cidial, fungicide M 9834 and herbicide chlorfenac.Natural phenylacetic acid is with its first
The form of ester is present in cocoa, coffee and strawberry, shows slightly sweetish weak honey and musk odor.However natural benzene
Acetic acid is only present in above-mentioned fruit with flavor substance, and content is little, extracts and be enriched with the need for being not easy and being far unsatisfactory for market
It asks.The phenylacetic acid for being used as raw material or intermediate in medicine and pesticide industry is all from organic synthesis, can high yield synthesis benzene second
The route of acid has as many as more than ten, such as reacting, in high temperature and pressure and carbonylation synthesis in the benzyl chloride of precious metal catalyst and formic acid
Benzyl chloride or benzylalcohol and carbon monoxide reacts, using the chlorination of phase transfer catalytic technology and electrochemical method under catalyst action
The reacting of benzyl and carbon dioxide, the selective oxidation reaction of phenylacetaldehyde or benzyl carbinol, benzene acetonitrile catalytic hydrolysis reaction, mandelic acid or
The catalyzing hydrolysis for being catalyzed decarboxylation reaction, the catalytic reduction reaction of carbonyl phenylacetic acid, phenyl acetamide of the hydroxyacetic acid of meso
Reaction, the catalysis of the catalytic thermal decarboxylic reaction of phenylmalonic acid, the dehydroxylation of hydroxyl benzene acetonitrile and hydrolysis, chlorophenyl acetic acid
Reduction reaction, the hydrolysis of phenylacetate, Penicillinamide enzyme catalyzed hydrolysis and microbe fermentation method etc..Synthesis is examined
Consider the factors such as raw material sources, the reliability of synthetic technology and production cost, the method master of the common synthesis phenylacetic acid of industrialization at present
There is the catalytic thermal decarboxylic reaction of the hydrolysis of benzene acetonitrile, the catalysis of carbonyl synthetic reaction of benzyl chloride and phenylmalonic acid, this
The advantage of three synthetic methods is that raw material is easy to get, the yield of the conversion ratio of reactant and product is high and production cost is opposite
It is lower, it is possible remaining in the product to be disadvantageous in that first route uses hypertoxic hydrogen cyanide to deposit for Material synthesis benzene acetonitrile
The doubt of hydrogen cyanide, Article 2 route in addition to use cause hemoglobin lose oxygen carrying capacity hypertoxic carbon monoxide for raw material other than
Condition of high voltage in reaction process not less than 5 MPa also increases operational risk simultaneously, synthesis of phenyl the third two in Article 3 route
The condition harshness and yield of acid be high and the atom utilization of subsequent decarboxylic reaction is low.
Phenylacetic acid is important the intermediate of medicine and pesticide, but the existing synthesis phenylacetic acid with industrial value
In synthetic method or selects the raw material of severe toxicity and cause the doubt that may remain severe poisonous chemicals or select high reaction
Pressure condition and the conjunction for increasing the insecurity factor or selection that increase production process to the high voltage bearing demand of equipment and simultaneously
Low at atom utilization in method, therefore exploitation one new green safe production phenylacetic acid synthetic method becomes in medicine
One important research direction of mesosome and pesticide intermediate.
Summary of the invention
In view of the shortcomings of the prior art, the present invention provides it is a kind of using biological degradability is good and green safe glycolide or
Oligoglycolic acid reacts the new synthesis of synthesis phenylacetic acid with large chemical industry benzene feedstock under normal pressure and Lewis acid catalysed conditions
Method.
To achieve the above object, The technical solution adopted by the invention is as follows: the benzene and glycolide that are 25 ~ 5:1 by mass ratio
Or oligoglycolic acid reacts at 35 DEG C ~ 80 DEG C of temperature under 1.0 ~ 1.3 times of amount of oxygen acetyl group substance of Lewis acid catalysis
1h ~ for 24 hours, through with water quenching reaction, inorganic acid acidification is added, grease is mutually layered, solvent is evaporated off and is dry after phenylacetic acid is thick
Product, phenylacetic acid crude product is further evaporated under reduced pressure or vacuum fractionation obtains the phenylacetic acid product that content is not less than 99.5wt%.
Preferably, the Lewis acid is aluminium chloride, zinc chloride, ferric trichloride or boron trifluoride.
Preferably, it is gaseous vapor, the water that states of matter is liquid that the water in water quenching reaction, which is states of matter,
Or states of matter is solid ice.
Preferably, the inorganic acid is sulfuric acid or hydrochloric acid or nitric acid or hydrobromic acid.
Further, the technical solution adopted by the present invention specifically: stir the benzene of the quality proportioning and glycolide mixed
Lewis acid is added portionwise after closing uniformly, 1h ~ for 24 hours is then reacted at 35 DEG C ~ 80 DEG C of temperature, through with water quenching reaction, nothing is added
Machine strong acid is acidified, grease is mutually layered, solvent is evaporated off and obtains phenylacetic acid crude product after dry, and phenylacetic acid crude product is further depressurized
Distillation or vacuum fractionation obtain the phenylacetic acid product that content is not less than 99.5wt%；
Alternatively, glycolide or oligoglycolic acid is added portionwise in the benzene of the quality proportioning and Lewis acid after mixing, then
1h ~ for 24 hours is reacted at 35 DEG C ~ 80 DEG C of temperature, through with water quenching reaction, inorganic acid acidification is added, grease is mutually layered, it is molten to be evaporated off
Phenylacetic acid crude product is obtained after agent and drying, phenylacetic acid crude product is further evaporated under reduced pressure or vacuum fractionation obtains content and is not less than
The phenylacetic acid product of 99.5wt%.
Preferably, it is described with water quench reaction and be added inorganic acid acidification be first be added water quenching reaction, then
It is all dissolved with mineral acid acidified to solid；Or it is described with water quench reaction and be added inorganic acid acidification be by ice with
Quenching reaction and acidification in reaction system are then added to after mixed in hydrochloric acid.
The severe poisonous chemicals such as hydrogen cyanide and carbon monoxide are neither selected in synthetic method of the invention, thus eliminate it is micro or
Product Safety doubt caused by trace raw material is remaining, and do not use high reaction pressure condition without using reaction under high pressure to set
Standby, to improve the safety of production process, while the raw materials used in the present invention biological degradability is good and green safe, synthesis is anti-
Answer Atom economy height.Compared with synthesizing phenylacetic acid synthetic method with other of industrial value, the present invention has following aobvious
Write the utility model has the advantages that
(1) it is Material synthesis phenylacetic acid that the present invention, which does not select the hydrogen cyanide of severe toxicity, and possible hypertoxic raw material is eliminated from source
Residual causes the doubt of Product Safety；
(2) present invention does not select high reaction pressure condition to synthesize phenylacetic acid, avoids the equipment pressure resistance of condition of high voltage bring
It is required that the problems such as high low with operational safety；
(3) present invention selects biological degradability good and environmentally friendly good glycolide or oligoglycolic acid are raw material, enhances
The environment friendly of fully synthetic route；
(4) glycolide or oligoglycolic acid high yield conversion are phenylacetic acid in the present invention, and the source of glycolide and oligoglycolic acid
From utilization rate up to 100%, excessive benzene is reusable through being distilled to recover in raw material, therefore reaction process environment friendly is good；
(5) present invention selects inexpensive benzene and the glycolide being easy to get or oligoglycolic acid is raw material, and glycolide or oligomeric second
The atom utilization of the high conversion rate for being converted into phenylacetic acid of alkyd, glycolide or oligoglycolic acid is high, after excessive benzene recycling
Still can reuse, therefore the good economy performance of the synthetic method route.
Specific embodiment
Below with reference to specific embodiment, the invention will be further described, but is not limited in any way the present invention
System, based on present invention teach that it is made it is any transform or replace, all belong to the scope of protection of the present invention.
Embodiment 1
Benzene and 116 g glycolides by 1740g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control dress
It is uniformly mixed in the reaction kettle set, then divides more batches 290g aluminum trichloride (anhydrous) to be added in system and is dispersed with stirring
It is even；System temperature is increased to 80 DEG C, the reaction was continued under constant stirring 3 h；It is broken that 300g is added in system after reaction
Newly-generated precipitating is reacted and is dissolved in the mixture quenching of the concentrated hydrochloric acid of ice and 208g36.5%；Benzene layer is rotated after stratification
Benzene is recycled in evaporation, and the product after recycling benzene is vacuum dried to obtain 271g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50
DEG C warm water be under the vacuum distillation of cooling medium purity be 99.8% phenylacetic acid 261.4g.
Embodiment 2
Benzene and 116 g glycolides by 2430g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control dress
It is uniformly mixed in the reaction kettle set, then divides more batches 310g aluminum trichloride (anhydrous) to be added in system and is dispersed with stirring
It is even；System temperature is increased to 70 DEG C, the reaction was continued under constant stirring 4 h；It is broken that 200g is added in system after reaction
Ice quenching reaction, the concentrated hydrochloric acid that 821g10% is then added dropwise dissolve newly-generated precipitating；By benzene layer rotary evaporation after stratification
Benzene is recycled, the product after recycling benzene is vacuum dried to obtain 274g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50 DEG C of temperature
Water be under the vacuum distillation of cooling medium purity be 99.7% phenylacetic acid 263.8g.
Embodiment 3
By 2550g moisture content lower than 0.05% benzene and 318g aluminum trichloride (anhydrous) be added to heating, condensation, stirring and
It is uniformly mixed in the reaction kettle of temperature control device, then divides more batches 116 g glycolides are added in system and are dispersed with stirring
Uniformly；System temperature is increased to 45 DEG C, the reaction was continued under constant stirring 16 h；200g is added in system after reaction
Trash ice quenching reaction, the concentrated hydrochloric acid that 410g20% is then added dropwise dissolve newly-generated precipitating；Benzene layer is rotated after stratification and is steamed
Receipts benzene is sent back to, is dried in vacuo to obtain 272g phenylacetic acid crude product after recycling benzene；Phenylacetic acid crude product is with 50 DEG C of warm water at 2 mmHg
Under the vacuum distillation of cooling medium purity be 99.5% phenylacetic acid 261.0g.
Embodiment 4
Benzene and 116.0g glycolide by 2080g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control
It is uniformly mixed in the reaction kettle of device, then divides more batches 283g aluminum trichloride (anhydrous) is added in system and is dispersed with stirring
Uniformly；System temperature is increased to 65 DEG C, the reaction was continued under constant stirring 19 h；200g is added in system after reaction
Trash ice quenching reaction, the sulfuric acid that 153g70% is then added dropwise dissolve newly-generated precipitating；By benzene layer rotary evaporation after stratification
Benzene is recycled, the product after recycling benzene is vacuum dried to obtain 272 g phenylacetic acid crude products；Phenylacetic acid crude product is at 2 mmHg with 50 DEG C of temperature
Water be under the vacuum distillation of cooling medium purity be 99.8% phenylacetic acid 261.0g.
Embodiment 5
Benzene and 116.0 g glycolides by 1400g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control
It is uniformly mixed in the reaction kettle of device, then divides more batches 320.0g aluminum trichloride (anhydrous) is added in system and is stirred and divide
It dissipates uniform；System temperature is increased to 55 DEG C, the reaction was continued under constant stirring 6 h；It is added in system after reaction
The quenching reaction of 200g trash ice, the sulfuric acid that 1040 g10% are then added dropwise dissolve newly-generated precipitating；Benzene layer is revolved after stratification
Turn evaporation recycling benzene, the product after recycling benzene is vacuum dried to obtain 271g phenylacetic acid crude product；Phenylacetic acid crude product at 2 mmHg with
50 DEG C of warm water be under the vacuum distillation of cooling medium purity be 99.9% phenylacetic acid 260.0g.
Embodiment 6
Benzene and 116 g glycolides by 696g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control dress
It is uniformly mixed in the reaction kettle set, then divides more batches 275g aluminum trichloride (anhydrous) to be added in system and is dispersed with stirring
It is even；System temperature is increased to 60 DEG C, the reaction was continued under constant stirring 7 h；It is broken that 200g is added in system after reaction
Ice quenching reaction, the sulfuric acid that 340g30% is then added dropwise dissolve newly-generated precipitating；Benzene layer rotary evaporation is returned after stratification
Benzene is received, the product after recycling benzene is vacuum dried to obtain 270.9g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50 DEG C of temperature
Water be under the vacuum distillation of cooling medium purity be 99.7% phenylacetic acid 260.3g.
Embodiment 7
Benzene and 116.0 g glycolides by 2900g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control
It is uniformly mixed in the reaction kettle of device, then divides more batches 280g aluminum trichloride (anhydrous) is added in system and is dispersed with stirring
Uniformly；System temperature is increased to 60 DEG C, the reaction was continued under constant stirring 4 h；200g is added in system after reaction
Trash ice quenching reaction, the nitric acid that 924g15% is then added dropwise dissolve newly-generated precipitating；By benzene layer rotary evaporation after stratification
Benzene is recycled, the product after recycling benzene is vacuum dried to obtain 271g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50 DEG C of temperature
Water be under the vacuum distillation of cooling medium purity be 99.8% phenylacetic acid 260.8g.
Embodiment 8
Benzene and 116 g glycolides by 812g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control dress
It is uniformly mixed in the reaction kettle set, then divides more batches 330g anhydrous ferric trichloride to be added in system and is dispersed with stirring
It is even；System temperature is increased to 60 DEG C, the reaction was continued under constant stirring 19 h；It is broken that 200g is added in system after reaction
Ice quenching reaction, the nitric acid that 277g50 % is then added dropwise dissolve newly-generated precipitating；By benzene layer rotary evaporation after stratification
Benzene is recycled, the product after recycling benzene is vacuum dried to obtain 275g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50 DEG C of temperature
Water be under the vacuum distillation of cooling medium purity be 99.8% phenylacetic acid 264.0g.
Embodiment 9
Benzene and 116 g glycolides by 2700g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control dress
It is uniformly mixed in the reaction kettle set, then divides more batches 307g zinc chloride to be added in system and is dispersed with stirring uniformly；It will
System temperature is increased to 60 DEG C, the reaction was continued under constant stirring 18 h；It is sudden that 200g trash ice is added in system after reaction
It goes out reaction, the hydrobromic acid that 441 g40% are then added dropwise dissolves newly-generated precipitating；Benzene layer rotary evaporation is returned after stratification
Benzene is received, the product after recycling benzene is vacuum dried to obtain 270g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50 DEG C of warm water
For under the vacuum distillation of cooling medium purity be 99.9% phenylacetic acid 259.9g.
Embodiment 10
By 2900g moisture content lower than 0.05% benzene and 280g aluminum trichloride (anhydrous) be added to heating, condensation, stirring and
It is uniformly mixed in the reaction kettle of temperature control device, then divides more batches 116 g glycolides are added in system and are dispersed with stirring
Uniformly；System temperature is increased to 45 DEG C, the reaction was continued under constant stirring 15 h；200g is added in system after reaction
Trash ice quenching reaction, the concentrated hydrochloric acid that 208g36.5% is then added dropwise dissolve newly-generated precipitating；Benzene layer is rotated after stratification
Benzene is recycled in evaporation, and the product after recycling benzene is vacuum dried to obtain 272g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg with 50
DEG C warm water be under the vacuum distillation of cooling medium purity be 99.9% phenylacetic acid 261.0g.
Embodiment 11
Benzene and 116 g glycolides by 1500g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature control dress
It is uniformly mixed in the reaction kettle set, then divides more batches to be added to 300g50% boron trifluoride etherate in system simultaneously
It is dispersed with stirring uniformly；System temperature is increased to 35 DEG C, the reaction was continued under constant stirring 6 h；After reaction in system
The quenching reaction of 400g trash ice is added, the concentrated hydrochloric acid that 218g36.5% is then added dropwise dissolves newly-generated precipitating；It will after stratification
Benzene layer rotary evaporation recycles benzene, and the product after recycling benzene is vacuum dried to obtain 270g phenylacetic acid crude product；Phenylacetic acid crude product is 2
Under mmHg using 50 DEG C of warm water as under the vacuum distillation of cooling medium purity be 99.8% phenylacetic acid 259.9g.
Embodiment 12
By 1980g moisture content lower than 0.05% benzene and 116.8 g oligoglycolic acids be added to heating, condensation, stirring and
It is uniformly mixed in the reaction kettle of temperature control device, then divides more batches 300g aluminum trichloride (anhydrous) is added in system and is stirred
It is uniformly dispersed；System temperature is increased to 45 DEG C, the reaction was continued under constant stirring 8 h；It is added in system after reaction
The quenching reaction of 200g trash ice, the concentrated hydrochloric acid that 228g36.5% is then added dropwise dissolve newly-generated precipitating；By benzene layer after stratification
Rotary evaporation recycles benzene, and the product after recycling benzene is vacuum dried to obtain 273.1g phenylacetic acid crude product；Phenylacetic acid crude product is in 2 mmHg
Under using 50 DEG C of warm water as under the vacuum distillation of cooling medium purity be 99.6% phenylacetic acid 262.3g.
Embodiment 13
Benzene and 116 g oligoglycolic acids by 813g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature
It controls and is uniformly mixed in the reaction kettle of device, then divide more batches 293g aluminum trichloride (anhydrous) is added in system and is stirred and divide
It dissipates uniform；System temperature is increased to 35 DEG C, the reaction was continued under constant stirring 18 h；It is added in system after reaction
The quenching reaction of 200g trash ice, the concentrated hydrochloric acid that 226g36.5% is then added dropwise dissolve newly-generated precipitating；By benzene layer after stratification
Rotary evaporation recycles benzene, and the product after recycling benzene is vacuum dried to obtain 274g phenylacetic acid crude product；Phenylacetic acid crude product is at 2 mmHg
Using 50 DEG C of warm water as under the vacuum distillation of cooling medium purity be 99.7% phenylacetic acid 263.3g.
Embodiment 14
Benzene and 116 g oligoglycolic acids by 1980g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature
It controls and is uniformly mixed in the reaction kettle of device, then divide more batches 308g aluminum trichloride (anhydrous) is added in system and is stirred and divide
It dissipates uniform；System temperature is increased to 55 DEG C, the reaction was continued under constant stirring 23 h；It is added in system after reaction
The quenching reaction of 200g trash ice, the concentrated hydrochloric acid that 225g36.5% is then added dropwise dissolve newly-generated precipitating；By benzene layer after stratification
Rotary evaporation recycles benzene, and the product after recycling benzene is vacuum dried to obtain 271.8g phenylacetic acid crude product；Phenylacetic acid crude product is in 2 mmHg
Under using 50 DEG C of warm water as under the vacuum distillation of cooling medium purity be 99.6% phenylacetic acid 261.0g.
Embodiment 15
Benzene and 298g aluminum trichloride (anhydrous) by 590g moisture content lower than 0.05% are added to heating, condensation, stirring and temperature
It controls and is uniformly mixed in the reaction kettle of device, then divide more batches 118 g oligoglycolic acids are added in system and are stirred and divide
It dissipates uniform；System temperature is increased to 65 DEG C, the reaction was continued under constant stirring 8 h；It is added in system after reaction
The quenching reaction of 200g trash ice, the concentrated hydrochloric acid that 228g36.5% is then added dropwise dissolve newly-generated precipitating；By benzene layer after stratification
Rotary evaporation recycles benzene, and the product after recycling benzene is vacuum dried to obtain 278.1g phenylacetic acid crude product；Phenylacetic acid crude product is in 2 mmHg
Under using 50 DEG C of warm water as under the vacuum distillation of cooling medium purity be 99.7% phenylacetic acid 267.2g.
Embodiment 16
By 2440g moisture content lower than 0.05% benzene and 116.2 g oligoglycolic acids be added to heating, condensation, stirring and
It is uniformly mixed in the reaction kettle of temperature control device, then divides more batches 280g aluminum trichloride (anhydrous) is added in system and is stirred
It is uniformly dispersed；System temperature is increased to 45 DEG C, the reaction was continued under constant stirring 15 h；It is added in system after reaction
The quenching reaction of 200g trash ice, the concentrated hydrochloric acid that 222g36.5% is then added dropwise dissolve newly-generated precipitating；By benzene layer after stratification
Rotary evaporation recycles benzene, and the product after recycling benzene is vacuum dried to obtain 270.3g phenylacetic acid crude product；Phenylacetic acid crude product is in 2 mmHg
Under using 50 DEG C of warm water as under the vacuum distillation of cooling medium purity be 99.8% phenylacetic acid 259.7g.
Claims (8)
1. a kind of synthetic method of phenylacetic acid, it is characterised in that: by mass ratio be (25 ~ 5): 1 benzene and glycolide or oligomeric second
Alkyd reacts the h of 1 h ~ 24 at 35 DEG C ~ 80 DEG C of temperature under 1.0 ~ 1.3 times of amount of oxygen acetyl group substance of Lewis acid catalysis,
Through with water quenching reaction, inorganic acid acidification is added, grease is mutually layered, solvent is evaporated off and is dry after phenylacetic acid product.
2. a kind of synthetic method of phenylacetic acid described in claim 1, it is characterised in that: stir the benzene and glycolide mixed
Lewis acid is added portionwise after closing uniformly.
3. a kind of synthetic method of phenylacetic acid described in claim 1, it is characterised in that: close the benzene and Lewis acid-mixed
Glycolide or oligoglycolic acid is added portionwise after uniformly.
4. a kind of synthetic method of phenylacetic acid described in claim 1, it is characterised in that: described to quench reaction with water and add
Entering inorganic acid acidification is water quenching reaction to be first added, then be acidified to solid with inorganic acid and all dissolve.
5. a kind of synthetic method of phenylacetic acid described in claim 1, it is characterised in that: described to quench reaction with water and add
Entering inorganic acid acidification is to be then added to quenching in reaction system after mixing water with inorganic acid to react and be acidified.
6. a kind of described in any item synthetic methods of phenylacetic acid of claim 1-3, it is characterised in that: the Lewis acid is
Aluminium chloride, zinc chloride, ferric trichloride or boron trifluoride.
7. a kind of synthetic method of phenylacetic acid described in any one of claim 1,4,5, it is characterised in that: described is inorganic strong
Acid is sulfuric acid or hydrochloric acid or nitric acid or hydrobromic acid.
8. a kind of synthetic method of phenylacetic acid described in any one of claim 1,4,5, it is characterised in that: described is sudden with water
It is gaseous vapor, the water that states of matter is liquid or states of matter is solid ice that the water to go out in reaction, which is states of matter,.
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| US20120253042A1 (en) * | 2007-10-30 | 2012-10-04 | Yeda Research And Development Co. Ltd. | Use of ruthenium complexes for formation and/or hydrogenation of amides and related carboxylic acid derivatives |
| CN102816076A (en) * | 2012-08-28 | 2012-12-12 | 山东汉兴医药科技有限公司 | Synthetic method of p-hydroxyphenylglycine |
| WO2013019635A1 (en) * | 2011-07-29 | 2013-02-07 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| CN103641704A (en) * | 2013-12-18 | 2014-03-19 | 福建省永安市智源生化有限公司 | Method for preparing phenylacetic acid derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120253042A1 (en) * | 2007-10-30 | 2012-10-04 | Yeda Research And Development Co. Ltd. | Use of ruthenium complexes for formation and/or hydrogenation of amides and related carboxylic acid derivatives |
| WO2013019635A1 (en) * | 2011-07-29 | 2013-02-07 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| CN102816076A (en) * | 2012-08-28 | 2012-12-12 | 山东汉兴医药科技有限公司 | Synthetic method of p-hydroxyphenylglycine |
| CN103641704A (en) * | 2013-12-18 | 2014-03-19 | 福建省永安市智源生化有限公司 | Method for preparing phenylacetic acid derivative |
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| CN111393282A (en) * | 2020-05-21 | 2020-07-10 | 湖南复瑞生物医药技术有限责任公司 | Preparation method of 2,4, 5-trifluorophenylacetic acid |
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