US3369043A - Process for the preparation of unsaturated carboxylic acids - Google Patents

Process for the preparation of unsaturated carboxylic acids Download PDF

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Publication number
US3369043A
US3369043A US634774A US63477467A US3369043A US 3369043 A US3369043 A US 3369043A US 634774 A US634774 A US 634774A US 63477467 A US63477467 A US 63477467A US 3369043 A US3369043 A US 3369043A
Authority
US
United States
Prior art keywords
acid
acrolein
range
methacrolein
hydroperoxide
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
US634774A
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English (en)
Inventor
Schlossman Irwin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Halcon Research and Development Corp
Original Assignee
Halcon International Inc
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.)
Filing date
Publication date
Priority to BE645825D priority Critical patent/BE645825A/xx
Priority to LU45783D priority patent/LU45783A1/xx
Priority to NL6403597A priority patent/NL6403597A/xx
Priority to GB14482/64A priority patent/GB1060777A/en
Priority to FR970444A priority patent/FR1395951A/fr
Priority to CH458864A priority patent/CH431497A/fr
Priority to DE19641468028 priority patent/DE1468028A1/de
Application filed by Halcon International Inc filed Critical Halcon International Inc
Priority to US634774A priority patent/US3369043A/en
Application granted granted Critical
Publication of US3369043A publication Critical patent/US3369043A/en
Assigned to HALCON RESEARCH AND DEVELOPMENT CORPORATION reassignment HALCON RESEARCH AND DEVELOPMENT CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HALCON INTERNATIONAL, INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/02—Formic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein

Definitions

  • the monomeric acrylic acid is separated by distillation, avoiding local overheating, and bubbling gaseous nitrogen through the mixture in order to inhibit polymerization.
  • Example 3 The procedure of Example 2 is repeated using a mixture of methacrolein (10.5 grams), t-butanol (35 grams), chromic acid (1 gram), and cumene hydroperoxide (34 grams), at room temperature for 24 hours.
  • the reaction mixture contains 2.7% methacrylic acid, the methacrolein conversion is 77% and the methacrylic acid selectivity based on reacted methacrolein is 21%.
  • Example 8 The procedure of Example 3 is repeated with alphaamylacrolein as the aldehyde, for producing alpha-amylacrylic acid, and similar results are obtained.
  • Example 9 The procedure of Example 3 is repeated using cyclohexanone peroxide as the hydroperoxide and similar good results are obtained.

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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US634774A 1963-04-12 1967-04-28 Process for the preparation of unsaturated carboxylic acids Expired - Lifetime US3369043A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE645825D BE645825A (enExample) 1963-04-12 1964-03-27
LU45783D LU45783A1 (enExample) 1963-04-12 1964-03-31
NL6403597A NL6403597A (enExample) 1963-04-12 1964-04-03
GB14482/64A GB1060777A (en) 1963-04-12 1964-04-08 Production of acrylic acid and substituted derivatives thereof
FR970444A FR1395951A (fr) 1963-04-12 1964-04-10 Procédé chimique pour la préparation d'acide acrylique
CH458864A CH431497A (fr) 1963-04-12 1964-04-10 Procédé de préparation d'un acide carboxylique non saturé
DE19641468028 DE1468028A1 (de) 1963-04-12 1964-04-13 Verfahren zur Herstellung von Acrylsaeure
US634774A US3369043A (en) 1963-04-12 1967-04-28 Process for the preparation of unsaturated carboxylic acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US27253663A 1963-04-12 1963-04-12
US634774A US3369043A (en) 1963-04-12 1967-04-28 Process for the preparation of unsaturated carboxylic acids

Publications (1)

Publication Number Publication Date
US3369043A true US3369043A (en) 1968-02-13

Family

ID=26955586

Family Applications (1)

Application Number Title Priority Date Filing Date
US634774A Expired - Lifetime US3369043A (en) 1963-04-12 1967-04-28 Process for the preparation of unsaturated carboxylic acids

Country Status (7)

Country Link
US (1) US3369043A (enExample)
BE (1) BE645825A (enExample)
CH (1) CH431497A (enExample)
DE (1) DE1468028A1 (enExample)
GB (1) GB1060777A (enExample)
LU (1) LU45783A1 (enExample)
NL (1) NL6403597A (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4324331A (en) * 1980-08-08 1982-04-13 Zimmer, Inc. Packaging for surgical implements

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2744928A (en) * 1952-11-28 1956-05-08 Shell Dev Oxidation of unsaturated aldehydes to acids

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2744928A (en) * 1952-11-28 1956-05-08 Shell Dev Oxidation of unsaturated aldehydes to acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4324331A (en) * 1980-08-08 1982-04-13 Zimmer, Inc. Packaging for surgical implements

Also Published As

Publication number Publication date
GB1060777A (en) 1967-03-08
NL6403597A (enExample) 1964-10-13
LU45783A1 (enExample) 1965-10-01
CH431497A (fr) 1967-03-15
DE1468028A1 (de) 1969-01-23
BE645825A (enExample) 1964-09-28

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Legal Events

Date Code Title Description
AS Assignment

Owner name: ATLANTIC RICHFIELD COMPANY, 1500 MARKET STREET, PH

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:HALCON RESEARCH AND DEVELOPMENT CORPORATION, A CORP. OF DE;REEL/FRAME:003845/0048

Effective date: 19810304