Method for producing polyalkylene glycol derivative with narrow molecular weight distribution, and acetal group-containing alcohol compound for use therein and alkali metal salt thereof

A method for producing a narrow molecular weight distribution polyalkylene glycol derivative having an amino group at an end represented by a general formula (7) comprising the following steps of:

• 1) a step of reacting a compound represented by the following general formula (2) with ethylene oxide in an organic solvent to obtain a compound represented by the following general formula (3):
• wherein R1 each independently represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 10 carbon atoms;
• R2 represents a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms;
• m each independently represents an integer of 1 to 5;
• and
• M represents sodium or potassium;
• wherein R1, R2, m, and M are the same as defined in the general formula (2);
• n represents an integer of 1 to 450;
• and
• k represents an integer of 0 to 5;
• 2) a step of reacting a compound represented by the following general formula (3) with a compound represented by the following general formula (8) to obtain a compound represented by the following general formula (4):
• R3(OCH2CH2)kX (8)
• wherein k is the same as defined in the general formula (3);
• R3 represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms;
• and
• X represents a halogen atom or a leaving group;
• wherein R1, R2, m, and n, are the same as defined in the general formula (3);
• and
• R3 is the same as defined in the general formula (8);
• 3) a step of reacting a compound represented by the general formula (4) with water in the presence of an acid catalyst to obtain a compound represented by the following general formula (5):
• wherein R2, R3, and n are the same as defined in the general formula (4);
• 4) a step of reacting a compound represented by the general formula (5) with ammonia or hydroxylamine to obtain a compound represented by the following general formula (6):
• wherein R2, R3, and n are the same as defined in the general formula (5);
• and
• R4 represents a hydrogen atom or a hydroxyl group;
• and
• 5) a step of producing a compound represented by the following general formula (7) by a reduction reaction of a compound represented by the general formula (6):
• H2N—CH2—R2—(OCH2CH2)n—OR3 (7)
• wherein R2, R3, and n are the same as defined in the general formula (6).

An acetal group-containing alcohol compound represented by the following general formula (1):

• wherein R1 each independently represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 10 carbon atoms;
• R2 represents a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms;
• and
• m each independently represents an integer of 1 to 5.

A metal salt of an acetal group-containing alcohol compound represented by the following general formula (2):

• wherein R1 each independently represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 10 carbon atoms;
• R2 represents a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms;
• m each independently represents an integer of 1 to 5;
• and
• M represents sodium or potassium.