Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide

Ralph, John; Karlen, Steven; Mobley, Justin

Title: Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide

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Abstract

Disclosed is a method to make N-acetyl-p-aminophenol. The method includes steps for converting biomass-derived p-hydroxybenzoates to p-hydroxybenzamide, then to p-aminophenol; and then N-acetylating the p-aminophenol.

Inventors:: Ralph, John; Karlen, Steven; Mobley, Justin

Issue Date:: 2019-05-14

Research Org.:: Wisconsin Alumni Research Foundation, Madison, WI (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1568317

Patent Number(s):: 10286504

Application Number:: 15/914,597

Assignee:: Wisconsin Alumni Research Foundation (Madison, WI)

Patent Classifications (CPCs):: H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60K - ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES

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H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
H01M8/10 - Fuel cells with solid electrolytes

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60K - ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES
B60K2015/03026 - {comprising a valve}

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
H01M16/006 - {of fuel cells with rechargeable batteries}

B - PERFORMING OPERATIONS B23 - MACHINE TOOLS B23P - OTHER WORKING OF METAL
B23P19/04 - for assembling or disassembling parts

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY
C07B2200/09 - Geometrical isomers

G - PHYSICS G05 - CONTROLLING G05D - SYSTEMS FOR CONTROLLING OR REGULATING NON-ELECTRIC VARIABLES
G05D23/1904 - {variable in time}

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
H01M2220/20 - Batteries in motive systems, e.g. vehicle, ship, plane
H01M8/04925 - {Power, energy, capacity or load}

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60K - ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES
B60K3/02 - of piston type

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02P - CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
Y02P70/50 - Manufacturing or production processes characterised by the final manufactured product

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02T - CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
Y02T10/70 - Energy storage for electromobility

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60K - ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES
B60K2015/03019 - {Filling of gas tanks}

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60L - PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES
B60L58/30 - for monitoring or controlling fuel cells

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02T - CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
Y02T90/12 - Electric charging stations

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02B - CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
Y02B90/10 - Applications of fuel cells in buildings

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
H01M2250/20 - Fuel cells in motive systems, e.g. vehicle, ship, plane

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60L - PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES
B60L53/35 - Means for automatic or assisted adjustment of the relative position of charging devices and vehicles
B60L53/14 - Conductive energy transfer

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
H01M8/04298 - Processes for controlling fuel cells or fuel cell systems

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E60/10 - Energy storage

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60L - PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES
B60L53/66 - Data transfer between charging stations and vehicles

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C213/02 - by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02T - CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
Y02T90/16 - Information or communication technologies improving the operation of electric vehicles

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E60/32 - Hydrogen storage

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02T - CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
Y02T90/40 - Application of hydrogen technology to transportation
Y02T90/14 - Plug-in electric vehicles

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60L - PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES
B60L58/10 - for monitoring or controlling batteries
B60L53/60 - Monitoring or controlling charging stations

F - MECHANICAL ENGINEERING F17 - STORING OR DISTRIBUTING GASES OR LIQUIDS F17C - VESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES
F17C2265/061 - for supply of supplying vehicles

B - PERFORMING OPERATIONS B60 - VEHICLES IN GENERAL B60K - ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES
B60K15/03006 - {Gas tanks

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E60/50 - Fuel cells

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02T - CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
Y02T10/7072 - Electromobility specific charging systems or methods for batteries, ultracapacitors, supercapacitors or double-layer capacitors

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C231/10 - from compounds not provided for in groups C07C231/02 - C07C231/08

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DOE Contract Number:: FC02-07ER64494

Resource Type:: Patent

Resource Relation:: Patent File Date: 03/07/2018

Country of Publication:: United States

Language:: English

Citation Formats


                    Ralph, John, Karlen, Steven, and Mobley, Justin. Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide.  United States: N. p., 2019. 
        Web.

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                    Ralph, John, Karlen, Steven, & Mobley, Justin. Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide.  United States.

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                    Ralph, John, Karlen, Steven, and Mobley, Justin. Tue .  
        "Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide".  United States.  https://www.osti.gov/servlets/purl/1568317.

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@article{osti_1568317,

  title        = {Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide},

  author       = {Ralph, John and Karlen, Steven and Mobley, Justin},

  abstractNote = {Disclosed is a method to make N-acetyl-p-aminophenol. The method includes steps for converting biomass-derived p-hydroxybenzoates to p-hydroxybenzamide, then to p-aminophenol; and then N-acetylating the p-aminophenol.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2019},

  month        = {5}

}

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